Chapter 1 – Sir Michael Winston’s Offer

 

It was about six months ago that our life changed drastically, shortly after Papa had been killed tragically in the terrible accident at the textile plant that was owned by Sir Michael Winston. Our mother had departed from us 17 years ago after the birth of my younger twin sister Jamie. So we are now legally orphans. My sister Jamie and I, still in our teens, were privileged to be attending the Collinsworth Finishing Academy, but with Papa gone now, our future was uncertain. The Academy has a wonderful reputation for turning out refined young ladies at a perfect marrying age. We had just finished our spring semester finals when we got the word that our Papa had been killed. We were both looking forward to coming home for the summer to be with Papa, but now we both just cried, realizing that we were truly alone. My name is Julie, and I feel solely responsible for the future well being of both my younger sister and myself.

 

It was then that Sir Michael Winston sent for us to come to his estate to make plans for Papa’s funeral and to stay with him for the summer. His estate was located just outside of Sussex, and about an hour carriage ride from The Academy. With grieving hearts, we accepted his invitation to return and to visit and were waiting at school for his butler to pick us up in his carriage. We talked about Sir Michael and how nice it was of him to send for us. We had met him many times before, and as a rich young bachelor in his early-thirties, we both thought he was very handsome and attractive. We both were wondering what our futures would hold in store for us, when we saw Sir Michael’s bright red carriage came into view.

 

His butler, Carlton, greeted us cordially, and helped to put our luggage into the back of the carriage. Then after our hour ride to the estate, we finally arrived and were escorted into Sir Michael’s study. He not only owned the textile plant, but was a knowledgeable and skilled lawyer.

 

As we entered, he said, “Hello Ladies. It’s nice to see the both of you again, but I wish it were under more pleasant circumstances. Please be seated, and realize that I am dreadfully sorry about your father’s accident. He was a wonderful man. I need you to help me plan out your father’s funeral, so that we might give him one befitting a man as wonderful as he was. Your father appointed me as his legal “man of affairs”, a few years ago, and it is good that he made such plans.”

 

We sobbed through most of the day, but helped Sir Michael to make the necessary funeral plans. We told him about Papa’s favorite songs and the memories that we both shared of our happy days with Papa. The funeral took place two days later.

 

On the day after the funeral, we both were awakened in our adjacent rooms to the chirping of birds outside, and a pretty little brunette maid, named Collette, bringing us pancakes and sausages for breakfast in our bedrooms. We had never been treated so royally. After we had eaten, bathed, and gotten dressed, the maid came back and politely summoned both of us to report to Sir Michael’s study. We wondered what he could want, now.

 

As we knocked and entered, he asked us to sit down and then said, “Your father made arrangements with me for his affairs, but he didn’t think to make any arrangements for your welfare. However, since I know and like both of you girls very much, I am prepared to offer you an opportunity, instead of being forced to choose one of the other terrible options. “

 

Jamie and I looked at each other in disbelief, and then said, “Terrible options, Sir?”

 

“Yes girls, terrible options. You see, your father was in debt to me for a considerable amount of money, including the tuition for your schooling. I am recovering part of his debt by reclaiming and selling his house and his land. But for the remaining debt and your tuition debt, you could both be sold as servants, or as laborers to work your debt off, or worse, go to the Bridewell debtor’s prison.  However, I am willing to offer you both an opportunity to stay with me, and to enjoy the comforts that life with me could provide two beautiful girls like yourself.”

 

Jamie and I both blushed at hearing him say that we were both beautiful girls. Now I had always thought that I was pretty; standing 5’6” tall, light curly blonde hair, blue eyes, and having an almost perfect slim figure. But to be admired by a man of Sir Michael’s standing was indeed an honor. Jamie was cute too, standing 5’5”, with honey blond hair and almost a carbon copy of me.

 

We both perked up and said, “OOhhh Thank You, Sir! May we hear about this opportunity that you are willing to offer both of us.” He rose and smiled as he moved over by us. “Girls, I have a fondness for both of you. Your father was a dedicated worker for me, and I am willing to keep the two of you here with me under my guardianship as my “wards”, under two conditions. I am a very busy man, and I have need of two faithful assistants such as yourselves, who would be at my beck and call and willing to be of service at all times. Would the both of you be interested?”

 

Jamie and I both light up and say, “OOOhhh, yes, Sir!” We were both very excited about his offer, and I raised my hand and asked, “Sir, what are the two conditions that you mentioned earlier?”

 

Sir Michael smiled and said, “Julie, you are not only pretty, but very intelligent, too. Thank you for asking that question, young lady. First, I’d want both of you to be totally devoted and honest with me in all matters. Then second, I’d want both of you to do whatever I ask of you at all times, without questioning. Any disobedience will result in harsh physical discipline being administered to you as a consequence. Can I count on both of you to be honestly devoted, and obedient to both of my rules?”

 

Jamie and I looked at each other, and then quickly nodded.  Speaking for both of us, I say, “Yes Sir! We are grateful to you for all you have done for our Papa and for us. It is most kind of you to offer us this opportunity to live with you under your guardianship, as your “wards”. Thank you, Sir! We will do our best to please you and make you proud of us, Sir Michael.”

 

“I hope so!” he said. Then he smiled and told both of us to stand up. He opened his briefcase and showed us each a document that he asked us to sign. It gave him full custody and legal right to be our legal guardian until we both reached the age of twenty-one. We gladly signed it, and then he gave both of us a welcoming hug. He then kissed our cheeks and told us that he would start our training immediately. We were thrilled, and He said that he was happy that we had accepted his invitation. He also said that he was quite concerned about our health, due to all the stress that we had been through. He told us that he would make an appointment with Dr. Brown to come over to the estate to give us a thorough physical examination this afternoon. All of his household staff had yearly examinations, and we would be no different.

 

Never having had an examination before, we were frightened and started to protest. But he raised his finger and said, “AAhh, AAhh, Girls, Rule number 2. Remember, you promised to do whatever I said, without question. After all, it is in your best interest and for your health that I request this. ”

 

We suddenly quieted and then reluctantly accepted his request. Little did we realize what lay in store for us, or what he had in mind when he said our training would begin immediately.

 

Chapter 2 – The Examination

 

We had just eaten a light lunch, when the good Doctor arrived. He was young, probably late-twenties, and very handsome. He and Sir Michael escorted us up to our respective rooms. They left Jamie in her room and then the Doctor and Sir Michael came into my room, closed the door, and told me to undress completely. I began to protest and say, “But Sir, it would be lewd and indecent for me to disrobe in front of both of you!”

 

Sir Michael walked over to a chest in my room and produced a riding crop from one of the drawers. Then he looked at me sternly in my face and said, “Julie, it is neither lewd or indecent for you to do as I ask. Remember rule number 2, Julie, without question?” Suddenly he smacked my bottom with the crop, and shivers coursed through me as I realized that other than for the spankings from Papa, and the Headmaster at school, no one else had ever spanked me or made me undressed for them. I shivered and blushed profusely, as I slowly began to unbutton my blouse. I felt like a naughty schoolgirl again, about to be spanked, and yet, I hadn’t done anything wrong. I didn’t want to end up in a sweatshop, or worse, a prison. I would have to comply with his wishes. Blushing beet red, I slowly slipped my blouse off, baring most of my budding breasts to their gaze. Then I unzipped my skirt and it dropped away from my hips, leaving me standing in my low cut chemise and drawers. I hesitated, and quickly Sir Michael smacked my bottom again with the crop, and the Doctor said, “Everything, Julie, we don’t have all day you know!”

 

Blushing profusely, I unbuttoned my chemise and it opened so they could see my twin budding titties. I blushed in shame even more as I knew I had no choice, and then I started to sob. Sir Michael reached for me and gently held me in his arms. “SSShhhh Julie, now quit it, or I will give you something to cry about for disobedience”. I remembered how Papa used to spank me until my bum was cherry red, and I didn’t want anything similar to that to happen here. My bum would hurt for days.  I finally gained my composure, and Sir Michael then helped me out of my chemise and then grasped my hands behind my back, as he let me sit down on my bed. Not having finished undressing, I sat on the bed, facing them, with my titties in full view.

 

The Doctor began to examine my breasts and rolled my nipples between his fingers. Never having been examined by a real Doctor before, so I had no idea what to expect. This all felt so incredibly strange. I didn’t know whether he should or shouldn’t do what he was doing. After playing with my nipples and titties for a few minutes and measuring them, Sir Michael released my arms and the Doctor asked me to stand up and to remove my drawers.

 

I was mortified and pleaded, “OOhhh Sir, please don’t ask me to be naked in front of both of you!” Suddenly, I felt an arm grab me as Sir Michael’s stern voice said, “Get up and drop those drawers immediately, Julie, or I will give you a spanking for disobedience that will leave your bottom red for days. You know the price for disobedience, and the good Doctor and I haven’t got all day. Now obey, or any more of this nonsense will be dealt with very harshly.”

 

Realizing that I had no choice, I stood up and slipped my thumbs into the waistband of my white lacey drawers. With trembling fingers, I slowly peeled the last bit of modesty and clothing away from my body. I stood before them naked, with my head down, and tears in my eyes.

 

Next, they made me lie down on the bed on my back. Then while Doctor Brown held my wrists over my head, Sir Michael brought a cup of shaving cream and dabbed it all over my soft golden fuzz guarding the entrance to my pussy. “I want your female area clean and bare down here. It saves you from infections, makes it easier for you to dress, and pleases me to see you bare down there.” He said. “I will shave you today, Julie, but from now on, I’ll expect you to keep it shaved and clean for health reasons, and for me.” Then with the Doctor’s help, they held me motionless as Sir Michael gently shaved my soft blonde pubic fuzz away. I whimpered as they were lathering me up and fingered my pussy. I knew that I would be absolutely bare and naked down there. They even shaved between my legs and removed all of those golden curls. I knew I would look like a naked little schoolgirl, bare of the fuzz of a woman. My female sex would be totally bare and I would be completely exposed down there. Finally he finished the job, and he wiped my bare pussy clean with a towel. Sir Michael lifted me up and made me stand before them. I literally died with shame, as his fingers began stroking and wiggling around on me down there. “Julie, you are so pretty and so lovely.” He said with a smile. I don’t know why, but I closed my eyes as his touch sent thrills through my naked body and I knew he felt my wetness betraying me.

 

The Doctor then turned me around, and made me kneel on the bed again, but this time with my bum up and elevated. I knew my inner most private regions and my bottomhole were totally on display for both of them to see. I was horrified and could feel my virgin pussy getting wetter by the second, and I was sure my pink anal dimple was winking at them as they spread my cheeks and started to stroke and examine me. I just buried my face in the sheets and endured what happened next.

 

I felt their hands on my bottom, spreading my cheeks wide and tickling my nether ring. I could feel my anal dimple spasm uncontrollably at their touch, as they gently massaged and rimmed my tight little hole with their fingers. They laughed and said how pink and puckered it was, and said it looked like an anal rose. Then the Doctor wetted his finger first with saliva and then quickly slipped it into my tight little anus. I squealed in dismay at this intrusions into my tight bottomhole. I’d never had anything inside me back there before, and never expected to be touched in so intimate a place. Then, after just a brief moment of debauchery, he stopped playing with my puckered little hole. “She is very tight!” Dr. Brown said. “We will have to stretch and exercise her!”  What did he mean by “stretch and exercise me?” I wondered?

 

With a man on each side of me, they spread my legs farther apart. Suddenly the Doctor’s hand began to finger my dripping virginal love purse. I gasped in alarming fright at their fondling, fearing the tearing of my virginal seal. Then as my body betrayed me, I unconsciously began to wiggle my bottom. My only thoughts were now on my tingling pussy, which I knew was absolutely dripping wet. “OOOhhh, Sir, OOOOhhhh,” I gasped, “Please spare me this indignity!” I pleaded, as he played with my love purse.

 

“It appears Sir Michael, that your pretty little ward is certifiably a little virgin, but it is obvious from her wetness that she is enjoying this examination more than she wants to let us know. Feel how wet she is here.”

 

I gasped into the sheets at his words. “How dare he say that I was enjoy what they were doing to me? They were forcing me to endure this! But OOOOhhhh, my God, did it feel excitingly tingly and so unbelievably stimulating.” I suddenly realized that despite this examination, I was totally under their control.

 

Sir Michael’s fingers then danced over my wet pussy lips and touched my sensitive little swollen clitoris. I trembled and squealed, as they held me there and he continued to tickle and rub over my tender swollen nib. “So let’s frig it to test her, and see if she responds!” Sir Michael said.

 

Suddenly, they both moved on either side of me and held me firmly. I jerked and wiggled my bottom, squealing uncontrollably as my body literally melted with a warm uncontrollable emotion as his fingers wiggled over my tender love bud. “OOOhhh, my God! OOOOhhhhh, Sir!” I squealed. I loved what he was doing to me, but I hated it, too! “OOOhhhh, my God, OOOhhhh,” I squealed again, as I felt my body quiver inside. Finally, I shuttered and trembled, squealing out uncontrollably again as I felt my body lose control and I flushed with sexual fever. He had induced some kind of a powerful wave-like feeling that made me shake and tremble like never before. This overwhelming feeling rolled through my private regions and made we weak. I tried to pull my legs together, but held as I was by them on each side of me, I was completely in their control and at their mercy. I had touched myself there before, because it felt good, but never had I felt anything like what had just happening to me right now. It was incredible and I never knew that a man could make me feel so hot and excited!

 

Sir Michael continued relentlessly to frig my tender bud, causing me to wiggle wantonly for him, and squeal out even more. I was so sensitive down there that I didn’t know what was happening to me, but I liked the feeling. Quickly the sensitivity gave way to another tidal wave orgasm rolling through me. It made me totally collapse on the bed with his hand still cupping my bare throbbing clit and womanhood. I hoped he didn’t plan to take my virginity, as I wanted to save that for the man whom I would one day marry. But never had I felt such powerful wonderful feelings, and if he wanted me, I was willing to totally surrender myself to his power and his will for me at that moment. At that moment, I couldn’t have stopped anything that was happening to me even if I had wanted to. After all I reasoned, he was my legal guardian now and I had consented to obey him regardless of what he asked.

 

Finally, my examination was over, and the Doctor left me to go into my sister Jamie’s room. Sir Michael sat on the bed next to me and rolled me onto my side to face him, saying, “You were a good girl Julie, but only after I had threatened to spank you.”

 

“I’m sorry, Sir! I’m really sorry if I behaved badly!” I replied.  Then he asked, “Tell me the truth, Julie, did you enjoy the experience that I just made you have?”  I blushed, rubbing my face as I softly whispered, “Yes, Sir, I did. It was so intense and overwhelming!” I admitted. I was afraid to say anything more about my virginity, but I was sure he wasn’t going to take me now.

 

Sir Michael smiled and lifted me up to give me a kiss on my cheek. Then he said, “I’m glad you liked it, Julie. It’s called an orgasm, and I needed to test to make sure that your body reacts properly, as a young woman should. You will be given lessons like this by me every day, Julie, to make sure that you remain in good health. It will be a pleasurable part of your daily training around here. I’m sure you will find life will be much more exciting for you, as time goes by around here. Now sit on the edge of the bed, Julie, and let me show you something.”

 

I sat down, and he moved right up next to my face. I noticed the big bulge in his trousers and suddenly he unzipped them and released his big throbbing manhood. I was both very surprised and quite in awe of his impressive member. It was massive, measuring almost 8 inches long, with a thick helmet head and a bright red color. I had never actually seen a male organ up close like this before. I’d only seen Papa’s through his underwear and heard talk from other girls about them. But this was the real thing, and it was throbbing in front of me. He bobbed it in front of my face, and said, “Julie, you have just learned how to orgasm for me, and now I want you to learn another lesson. I want you to learn how to give me pleasure, too. You do want to learn how to please me, don’t you, Julie?”

 

I was stunned and trembling and yet I knew that he wanted me to affirm to him that I was worthy of his affection. I quickly nodded and mumbled, “Yes, Sir. I do want to please you.” He reached down to stroke my pretty face and breathed, “You are a beautiful young lady, Julie, and as my ward, I want you to learn how to give pleasure as well as to receive it. Now touch my stiff manhood with your hand, and gently stroke the head up and down.”

 

I reached out and carefully touched his throbbing manhood. It pulsed in my grasp, as I slowly moved my fingers up and down on him. I was fascinated at its size and the massive helmet looking head. It literally jerked and throbbed under my touch. I felt him respond and moan under my caresses, and I knew he liked what I was doing for him. Then he gently touched my face and said, “What you are doing feels very good, but I want you to learn how to pleasure me with your mouth, Julie. I want you to open your sweet lips, and suck it into your mouth, and use your sweet lips to stroke on it, just as your fingers have been doing.”

 

I protested, “But Sir, I have never done anything like this before, and don’t know if I can!” He stroked my face with his big hand and slipped his thumb between my lips, saying, “Suck on this!” Not daring to disobey his command, my lips quickly wrapped around his thumb and I began to suck on it like a baby. Then after a few minutes, he pulled his thumb out and said, ”Now Julie, you have just showed me that you can suck on my finger. I want you to gently and carefully suck on the tip of my manhood, just as you did on my thumb. And Julie, don’t let me feel your teeth or I will spank your bottom for sure.”

 

Knowing that I had little chance of escaping my sentence, I opened my mouth and accepted his massive weapon between my lips. It felt strange, but I gently began to suck on his massive weapon, as I had on his thumb, only a few minutes ago. I must have been doing a good job, because Sir Michael started moaning and groaning with delight. “OOOhhh, yes, Julie, just like that!” He said.

 

I continued to suck and stroke him, allowing my saliva to lubricate and wet his manhood. Suddenly, I felt him grab my hair as he shoved his stiffness deep into my throat. I opened my mouth as wide as I could, desperately choking to accommodate him.  Then suddenly, he grabbed his cock and pulled back to the edge of my mouth as he sprayed a white gooey substance from his pulsing manhood all over my mouth and lips. I felt much of his warm essence dripping out of my mouth and running down my face, and I just sat there with his cumm dripping out of my open lips. After he was done squirting onto my waiting mouth, he took his finger and wiped most of it back into my open mouth. “Swallow it, Julie!”, He commanded. I had never tasted a man’s cumm before, but I was forced to do so now. It had a warm salty flavor that was strangely unique, and I swallowed most of it. After he had been totally drained of his essence, he said,  “Good Girl, Julie! You did well! From now on, whenever I ask you to suck me, I will require you to suck me to completion and swallow all of my juices. My orgasm and juices will be your reward for pleasing me, and you will learn to desire that reward as much as you desire to please me. Now go wash your face and get dressed, and wait for me down in my study. I need to go check on how the good Doctor is doing with your sister, sweet little Jamie.”

 

As my body calmed down from my multiple orgasms, and from just swallowing his spunk, I thought about how things had changed.  I thought about how sexy he made me feel and how good his touch had felt on me. I thought about how much I had thrilled in giving him pleasure with my lips and mouth, and how much he appreciated my efforts. He truly was a sensual man and it seemed like he wanted me to become sensual, too. I touched my sensitive little love button, reliving the thrilling orgasm that Sir Michael had given to me. I quickly realized that touching myself didn’t have anywhere near the same effect on me that Sir Michael’s hand had, especially when he wiggled my clitoris like he had, making me cumm for him. I had truly enjoyed touching his manhood, and even though I was forced to swallow most of his cumm, I enjoyed the feeling of satisfaction I had in pleasing him. I knew I was fast becoming a sensual woman who would delight in pleasing her man!

 

Then as I was finishing getting dressed, I heard noises from the other room. I listened closely and heard Jamie’s squeals and protests, and finally a few hard slaps. They were the same kind of gasps and squeals that I had been given only a few minutes before. I knew that my little sister was being shaved, tested and probably taught the same lesson by the Doctor and Sir Michael that as I had been taught earlier.

 

Chapter 3 – A Naughty Girl

 

I slowly got dressed and after arranging my hair so I looked good for him, I made my way to his study. It wasn’t very long before Sir Michael arrived and asked me to be seated next to him.

 

He opened up his briefcase and pulled out his riding crop. I began to tremble as he said, “Julie, four times this afternoon you questioned my authority and did not obey my requests immediately. I will not tolerate such blatant disrespect for my authority. You promised that you and Jamie would comply with my requests, and so you are going to be punished for your protests of disobedience. Now being the good little submissive girl that I know you are, bend over my desk and grasp the other side, so that you may receive your punishment for disobeying me.”

 

My stomach began to knot up. I knew he was right and I knew I had this spanking coming, even though I thought he was going to let my protests earlier slide by. I guess I was wrong. He stretched me over his desk and made me grasp the far side of it with my fingers and hold on tight. Then I felt my skirt and chemise being lifted. Suddenly as the air blew on my bottom, I remember my tragic mistake. I had been so wet down there after being frigged by him, that I neglected to put my drawers back on. When he flipped my skirt up and saw my bare cheeks, he slapped them hard and said. “OOhhh Miss Julie, you are a naughty girl. Did you leave your drawers off on purpose to seduce me, or are you being a naughty little girl who wants me to take your virginity?”

 

Immediately I squealed out, “Oohh NO, Sir! PLEASE, I forgot! Really I did! I’m sorry! You know I am a virgin and would like to remain as one until I am married. I beg your forgiveness Sir, and humbly accept whatever punishment you give me, only please spare my maidenhead!”

 

Suddenly, SMACKKK….SMACKKK….SMACKKKK…SMACKKK…, He stung my tender bottom cheeks with four stinging blows from his crop. I quivered over his desk, as he gave me another round of four SMACKKKS… Sir Michael continued to spank my bottom in rounds of four, until squealing, sobbing, and crying, I pleaded for “No more, PLEASE, Sir! I’m really sorry! MERCY! PLEASE, Sir!”

 

SMACKKK…SMACKKK….SMACKKK….SMACKKK…., He gave me one last round of four SMACKKKS, and then stopped. My bum was burning hot, like Papa used to make it. I felt a strange almost erotic feeling inside of me, and then I felt my own wetness dripping down my inner thigh. My bottom felt like it was glowing bright red and I knew my pussy was even wetter. What’s even worse, is that Sir Michael had enjoyed making me that way. Even though my bottom stung, I  was captivated by this man and secretly hoped that he would make me cumm for him again.

 

Chapter 4 – The First Step

 

He walked around to the front of his desk, and pulled out a cloth that he laid in front of me. I opened my eyes in fear and wonder as he unwrapped the linen cloth. “Julie, you are about to take your first step toward becoming my well trained assistant. I will respect your maidenhood virginity, but I will train you in all of the other ways that a woman can please a man. You will become my “cherry slave girl” and will do exactly everything that I ask of you. You will be trained and tested so that you will learn to please me in all ways.”

 

I thought about running away, since I now realized he wanted Jamie and me to be his “little sexual playthings”, and I didn’t know if my sister or I could endure that. To do what Sir Michael was planning to do to me would be so humiliating and strip me of all of my dignity. It would also require all of my willpower to perform for him, as he would expect me to. But he had excited me so much with his fingers earlier, being forced to perform for him and made to cumm under his masterful fingers. I knew I had no choice but to conform to his wishes and desires for me. He had said that this was the first step to becoming his slave, the first step of my truly submissive life with him. This would be a life for me that was so different then what I was used to, a life of sexual slavery.  At 18, my sexual experiences were very limited, almost non-existent, and now I was on the verge of a life of total sexual submission to a man who held me in the palm of his hand. I was in awe of his power over me, and knew that he would make me conform to his desires.

 

“Are you willing to accept your place here and have me begin your training. Julie?” he asked, “Or do I have to spank you into submission?”

I considered my options, and realized that I really didn’t want to end up on the streets or in prison, so Jamie and I had little choice. I softly answered, "If that is what you require of me, Sir, then that is what I will do. But please don’t hurt me."

”That's my good girl,” He laughed, “I wouldn't hurt you, Julie. In fact, I have every intention of helping you to enjoy your learning lessons as I enjoy your whimpers while you give me pleasure. That is what makes my cock hard, Julie girl, your whimpers of pleasure for me."

I trembled at his words and I watched him as he began to take out a selection of items from the drawer and place them in a nice, neat line on the white linen cloth. Some I recognized, others I did not. There were tubes of lubricant, a long probe with rubber beads, a series of large plugs, appear shaped thing, a double balloon thing with an inflating bulb and hoses coming out from it, and a medical speculum, all laid out in a nice neat row. I feared what he was going to do to me with those instruments, but I feared being abandoned to the harsh cruel authorities in town even more. I had never had any of these things in my body before, and I was overwhelmingly frightened. He moved behind me and said, "You have a lovely body, Julie. Now don’t move sweetie. You need to learn to accept my touches."

 

His hands began stroking my crimson red buttocks. I clung to the desk, as his hands moved all over her bottom. “I’ll bet you are already enjoying this, aren’t you Julie? I’ll bet your pussy is almost dripping wet." His hand reached down between my legs, and his thick fingers curling up under my butt cheeks touched my dripping slit. “AAHHHhhhh yes, my dear girl. I can tell this is exciting you.”

 

"Spread your legs open wide, Julie!  Hurry up, girl. I want to feel just how excited you really are." As my face turned red, his hand cupped all of my sex easily, and then a thumb popped inside of my anus. I squealed at the intrusion into my tight little bottom. “What is my thumb penetrating right now, Julie?, He demanded. I hesitated for a moment, until he rammed his thumb deeper and demanded, “Say it, Julie. Tell me all the words you know for this sweet little puckered opening that is mine.” His hand clenched and unclenched on my sex and moved into my anus, goosing my body, and making my hips wiggle seductively to try to escape his ravaging hand. SMACKKK. His hand shot out and hit my ass cheek hard. "I said, tell me." I stumbled for words, as he returned to goosing me between the legs, my hips involuntarily thrusting forward into his hand as he fondled my hot sex and clit, and probed my tight anal ring. “Aahhh, my anus, my asshole, my bottomhole, and my rosebud, Sir.”

"Very nice, Julie. You have such a beautiful ass, my dear, and I am going to enjoy training it so much. Have you ever had anything inside of your anus, before your examination today?”

 

“No, Sir!” I whispered. “Well get used to it, Julie, because you and I are going to become very intimate. I am going to let you remain a virgin, but I am going to make use of your other two orifices so that you may pleasure me whenever I desire. You have already learned a lesson on how to suck me with your mouth, and now we are going to work on your tight little anal rose.” I trembled at his words, and suddenly I realized what he was going to do. He wanted to stretch open my tight little asshole. That’s what he meant before about exercising and stretching my little hole. I was sure it would hurt, but I knew that I didn’t have much choice and must submit.
 
I turned red in embarrassment, as his hands moved over my bum and tickled me between my cheeks. Just like a little girl, with my ass revealed as if I was going to be punished with a spanking or something by my Daddy.

"You are such a good girl, Julie, and I like that." His hands continued to stroke my hot ass cheeks, feeling the taut flesh.  I clenched my ass cheeks tightly in fear. I was hoping to stop him from playing with me, or at least detour his other intentions.

His hands continued to grab my young ass flesh, rubbing my cheeks, still allowing me to tighten them whenever he got close to my tight anal ring. "Don't you like my touches there, Julie? I didn’t know what to say, but finally breathed out, “I’m afraid, Sir!”

 

He grinned and said, ”Yes my dear girl, I’m sure you are a little fearful, but you know that I desire you, and that you have promised to abide by my wishes. I promised to take care of you and you in turn are going to yield to me your tightest little hole, aren't you Julie? You know that I am doing all this to help prepare you for me, later. In fact you are going to help me to exercise your tight little nether hole. I am going to use many things inside your tiny asshole, and I will have to stretch it much wider for you to be able to take my manhood, later. You saw all these lovely little instruments, some of them are very small and some are very big. All of them will be used to stretch and “exercise” your tight little anus, until you are ready for me. When you are ready to yield your tight anal virginity to me, then I will accept your gift of your anal virginity, and take you with a lover’s passion. Until then, I will keep you as my protected ward, and make sure that your hands and mouth will get plenty of use as you relieve my pent up stress." I shivered at his words, while his hands continued to play with my bare flesh, massaging and rubbing my ass cheeks.

 

I quivered in fear as I realized that my tight little bottomhole was going to be someday plundered and penetrated by his big cock. I had never ever really considered that a man would want to penetrate a girl’s tight little bottomhole, but Sir Michael was determined to stretch mine with his toys and then his thick manhood. I considered all my alternate possibilities, and then trembling, I said, "I will do whatever you want, Sir Michael. I want to please you, Sir. You have been very kind to my sister and myself, and we do owe you some gratitude for that. Just please, Sir Michael, don't hurt me too much. Please be gentle with me and even though I know it will probably hurt and I probably won’t like it, I’ll do whatever you desire for me.  I will yield myself to you, Sir, but I beg you to please be gentle with me. It just felts so strange to have something in me back there."

"Shush, my little girl,” Sir Michael said. “I will take good care of you. I will lubricate your tight little asshole real good with my finger, real deep inside, so you are very wet and slippery. You want me to lubricate you, don't you Julie? You don't want me to do it to you dry? Tell me what you want me to do, Julie."

I began to sob, while his hands were still pawing all over my flesh like he owned me. "Yes," I replied.

"Yes what, Julie. Do you want me to penetrate you dry? Is that what you want?"

"No,” I squealed loudly, “I want you to lubricate me…., I mean lubricate my anus with your finger, Sir." I replied, humiliated at what he required me to say.

"OK Julie, I’ll do that for you, but first, I'm going to feel your pussy, Julie. I know you like that! I am going to put my fingers into your smooth little pussy and see how wet you already are. While I do that, I want you to loosen up your ass cheeks. I can't feel your anus if you keep your cheeks so tightly clenched. OK, Julie? Can you spread your legs and your cheeks a little wider for me, just a little wider so I have better access." His voice was so commanding, as he ordered me to perform for him.

Then I felt his cold fingers slip around into my pussy, tickling my pink folds. His other hand slipped between my cheeks, and his finger encircled my tight anal ring. I shuddered as he touched me there, while his other hand slipped around between the lips of her pussy. They were already dripping wet with my juices and from the weird excitement that I felt as a result of his intense desire for me. He was such a powerful man, and I knew he wanted me. I bowed out my legs, giving him greater freedom to my pussy, but also leaving my tiny anus unprotected from his fat finger that he soon pushed between my spread cheeks.

"Your pussy is so sweet and so wet. Someday you will make a great fuck for some lucky man.," he said. Then his fingers slipped deeper between her pussy lips, seeking out the barrier in my vagina. His other finger, the one circling my rear hole, tickled my anus and made it wiggle and wink. Wiggle your ass for me, Julie. I want you to show me that you are enjoying having me touch your virgin pussy and your tiny asshole. You want me to do this, don't you Julie? You want me to tickle your asshole, and massage your pussy like this, don't you?" he asked, teasing me. I shivered and felt so funny as he touched me and circled my tight little ring. I actually was enjoying his attentions, and so I said, “Yes, Sir! I do!”

He chuckled for a second, and then Michael stopped his fondling of me and moved behind me. He bent down so he would have an unobstructed view when I exposed my asshole to him.

 

"Now be a good girl, Julie, and reach back with both hands and spread your cheeks apart." Hesitantly I grabbed my youthful globes in my two small hands and with my fingers only inches from my asshole, I began to peel back the fleshy globes. "A little farther, Julie!” he asked.  “Spread them real wide for me, Julie.  Can you feel your tiny little rosebud puckering as it awaits my touch. It’s so cute! Imagine how much I will enjoy sliding my thick manhood between those pretty cheeks, and how big it will have to stretch to take my thick 8” cock."

 

He watched my expression of shame as I exposed my most intimate opening to his gaze. He blew on it, making me shiver in fear. Then he took his finger and tickled the rim of my anal ring. I wiggled my ass as he tickled me. He slapped my ass and he laughed as he continued to stimulate my tight little rosebud. Then he commanded to me, "Stretch yourself back over my desk, Julie, and hold on."

 

As soon as I had stretched myself out, gripping the edge of the other side, He pushed down on my back, forcing me down onto the surface.  "Push your ass up now! Good girl, Julie! Then he stepped in front of me and wrapped a wrist cuff around each wrist, and secured then around the front legs on his desk. I was stretched over his desk, and held in place for him to do with me as he willed. He looked into the eyes, and said, “I'm going to lubricate your asshole, first, Julie. Then you will be given an enema to clean you out. After you are totally clean, I will begin probing it with various instruments. All of them will all measure the elasticity of the sphincter in your asshole and help to prepare you for me."

I lay secured across his desk, my head resting on the hard surface, totally exposed to him. I saw him take a container from the table, and heard him unscrewing the metal cap. I knew that it was some form of lubricating jelly. I just waited for the touch of Sir Michael's hands rubbing between my ass cheeks and the lubrication he had promised to me. I was secured and helpless as Sir Michael took liberties with me that I never would of dreamed of letting anyone do to me. His hands continued rubbed and massaging my cheeks and tickling my anal rosebud.

 

Then he said, "Now relax, Julie, this is going to feel cold and strange." He placed his fingers on both sides of my asshole, stretching the little bud apart. His finger and the cold jelly on it touched my shriveled little rosebud. My body jerked in response as I knew my moment of anal training was about to begin. "Relax Julie,” He said,  “It’s only a little cool lubricant. Take a deep breath and relax your asshole. Now push your little anal rose out for me," He ordered.

He felt the tiny mouth push out and he took that opportunity to push in with his finger. His finger slid in effortlessly, helped by the slick jelly, while my asshole stretched tight around his knuckle. He heard me suck in a breath and gasp, as he began fingering my tight asshole. He twisted his finger inside of me, feeling me deeply, while his knuckle stretched my anus inward and outward to accommodate his plunging finger.

 

"Another deep breath, Julie," He said, as his finger pushed in harder. I felt every centimeter of his finger sliding along my anal tract on the slick jelly until his knuckles banged against the inner linings of my stretched asshole.

I felt violated and very exposed, while my sphincter tried to relax on the plunging finger inside of me. I felt my sphincter spasming, gripping his fat finger, hugging it tightly. Then I heard him open the top of the lubricant jar again.

"I’m going to rub it around inside this time, Julie. So relax your asshole again." His finger began moving out, then back in again, corkscrewing around inside of me. I knew he was lubricating me for bigger things, namely his 8” cock. He pulled his finger out and I heard him push it inside the jar again, a sloshing sound as he coated it again. "Now two fingers, Julie. Are you doing all right?"

"Is it going to hurt?" I whimpered. I braced myself, and then a sudden plunge back inside of me. His fingers were stretching my little hole wider and wider. It hurt as they turned and twisted around inside of me, not stopping until they were embedded deep, past his knuckles.

 

"OOOH," I cried out as Michael spread his fingers inside of me, stretching my anal tract to accommodate them.

He pulled his fingers from my asshole, watching as my little rosebud closed and winked at him, with the lubricating jelly making my tiny hole glisten. Then he walked in front of me and took the pear shaped double balloon shaped plug with the hand pump and hoses attached. I had never seen anything like this before, and didn’t realize what a wicked little device it really was. I had no idea what I was in for. He moved behind me and spread my cheeks wide, and said. “This is called a double balloon butt plug, Julie. And it is used to administer an enema to you.”

 

Suddenly I felt something nosing itself into my rectal opening and felt the cool rubber tip slide inside of me. Sir Michael slowly inched all of the balloon into my anus, and then began to pump it up. My anus expanded, as one balloon inside and one balloon outside of my rectum expanded my tight little hole. I soon felt strangely full back there. He then went over to the sink and brought back a large red bag filled with some kind of fluid. He attached the bag to one of the hoses, and suddenly I felt a rush of warm fluids fill the insides of my bottomhole. Plugged as I was and securely fastened over his desk, I had no other option than to suffer the indignities of having an enema. I knew what it was, because Papa had given me a few of them, but he didn’t use a double balloon plug, or secure me down. The fluid quickly filled my rectal cavity to bursting, and the cramps soon arrived. Plugged and restrained as I was, I could only whimper and plead for Sir Michael’s mercy.

 

As I sobbed and whimpered in pain for him, he reminded me, “Julie, you may squeal and cry all you want, but this is required for your own good and to clean out your colon. If I didn’t do this first, you couldn’t stand the training methods. Now just relax and hold it a bit more, and then I’ll let you void it.

 

I tried to be strong and tried to be brave, but it hurt so much! Finally, as I sobbed from the cramps and water pressure inside of my colon, I felt his hand on my bottom as he released some of the pressure inside of the balloon. He moved a basin behind me and gently pulled the plug out. My bowels gushed out their contents and soon I felt relief. Sir Michael gave me one more quick enema to rinse me, and then he gently cleaned and prepared me for my anal stretching exercises.

 

After he had cleansed my bottom, he picked up a long anal rubber probe. The device had to be over 14 inches long, with a pull ring on the end. The probe tip was skinny, barely the size of my little finger, but every two inches was a bead, about the size of a plum. The probe was used to test depths, the beads only purpose was to expand my anal tract as it moved in. He showed it to me, and said, "I'm going to see how deep this will go, Julie. It is going to feel very strange the deeper it goes. It will probably cause some cramping inside you, Julie, but you will be fine. I want you to lie still while I do it. Can you do that, Julie?" I nodded and said, “Yes, Sir, I’ll try!”

It looked so long and menacing. How was he ever going to get something that long inside me. I began breathing rapidly as I waited, unable to do anything but tremble in fear. Then I felt the probe at my anus and it slowly began to slide inside of me. I felt the pressure as it moved deeper inside of me, the first bead stretching my anus open before popping inside of me. Sir Michael continued to press the probe forward so the second bead now passing through my anus. My tight little rectum clamping down on the beads as they passed through. Two beads were now inside of me, stretching my anus open and then hugging them as they passed.

Michael watched carefully as over ten inches of the probe was pushed inside of my tight little asshole. Then the next bead stretched my asshole wider to accept it. He allowed it to enter before he began to move it, watching me as I moved my feet and danced as the probe was very uncomfortable by now. He began to pull it out, slowing down as the third bead was pulled loose. I gasped loudly as my asshole convulsed and had to shift to allow its passage. He pulled another bead from my asshole with a slight pop sound that could be heard throughout the room.

 

My body just shivered and trembled as I endured a trial the likes of which I had never previously known.  It felt like my guts were being pulled from me. Finally he pulled the last bead out and my anus began spasming wildly. My asshole felt hot and then empty as the last bead was pulled out. The little rubbery ring of my anus closed after the last bead in me popped free. He asked me, “Now that wasn’t so bad, was it, Julie?”

 

I let out a sigh of relief. "OOhhh Sir, it hurt terribly, and it gave me cramps when it was in so deep. I'm glad it's over," I said.

Sir Michael dipped the probe back in the jelly, "It's not over yet, Julie! I need to do it one more time, only this time deeper. I need to see how much your asshole can accept. After all, I am a very well endowed man, and I don’t want to hurt you when I plunge to your depths as I take your anal virginity. Now take a deep breath and relax again, like a good girl," Suddenly, I felt the probe push against my asshole. This time he didn’t wait for my response. Sir Michael pushed it all in with one continuous push. Restrained as I was, I screamed wildly and kicked out, as it hurt so much more, the deeper it went. I panted and gasped, in between sobs, as he pushed the anal balls in deeper.

It felt like a huge snake, as it continued to go inside of me, banging painfully against my anal tract as the balls expanded my rectal walls. I bowed my legs out, hoping to relieve some of the pain and cramping, but Sir Michael continued to press in even deeper. I could feel the beads go inside of me, now over 12 inches of thick rubber pressing upward into my previously unpenetrated colon. "AAAgghhhhh, PLEASE! OOOwwww, Sir, please hurry and get it over with," I cried out, “It really hurts!” as the probe continuing the deeper exploration of my anal tract.

Finally Sir Michael hit the limit of the probe. Any farther and I was sure he would cause serious damage to my anal tract for me. "You have it all, Julie, all fourteen inches of it. How does it feel?"

"OOOhhhh, GOD! PLEASE, take it out quick,” I squealed in panic, “The cramps are terrible."

 

I was dancing around on my toes, spreading my legs to try to stop the spasming cramps. Sir Michael took his time, pulling it out, then pushing it back in again, fucking my ass with the plunging probe.

"OOOhhh, Hurry," I begged. I finally felt it being reluctantly dragged from my plundered asshole. I slumped down on the table, glad to have it over with.

"We’re not done yet, Julie! Now I'm going to inspect inside your asshole." I groaned in dispair, as he pulled out a rectal speculum. It was over 6 ½ inches long, with three long prongs. It was built to spread an anal opening over three inches wide. The three prongs allowed maximum stretching and had a scissor like locking mechanism, allowing it to lock open at various widths.

My body went tense again when I saw the device. I knew it would hurt me when I was spread that wide. I heard the jar opening again, knowing what was coming. I watched as Sir Michael liberally put the jelly on the three prongs. "Must you do that, Sir? I beg you, please don't!" I sobbed, with tears running down my face and falling onto the table.

Sir Michael stroked my ass cheeks, and said, "Now, now Julie, I must inspect you properly. This makes it very easier for me to hold you open.  Now just relax your asshole, or it will hurt worse if you fight it. Trust me, Julie! I’ve opened a number of young girls bottoms to the pleasures of anal sex. In fact, my cousin, Doctor Brown and I have published a book on “Anal Sex Training” and have done this numerous times to young girls in our employment. This is for your own good, believe me!" He said.

 

I paused for a moment, “The Doctor is your cousin?”

 

Before I got an answer, I felt the cold metal instrument touch my asshole. I tensed up and felt the three probes running over my exposed anus before they finally started to enter me. It did not hurt very much as it went in, for which I was very thankful. Then Sir Michael twisted it a little bit to move the arms deeper into my rectum. I felt a little stretched, but the spread between them was only about an inch wide. Then HE reached for the tube of lubricant.

 

“Julie, I need to examine how your inner rectal tract responds to this ointment. I will probably use some of it to help lubricate your bottomhole when I take you. You would like me to lubricate you, wouldn’t you? Knowing I had no choice, I said, “YES, Sir! Please lubricate me good!”.

 

“I know you can stand a little more stretching, and it will give you an idea of how wide your anus will stretch to accommodate me." HE began to squeeze the scissors grip, watching as the three prongs began to expand my little hole. HE pulled the prongs a bit out until the outer flange locked on the lips of my anus. HE then slowly squeezed it again, satisfied that the prongs were secure, watching as my anus gaped widely before him.

"Stop PLEASE!," I screamed, as I felt my rubbery anal ring stretching wide open. The stretching of my sphincter muscles burned like fire and I feared that HE would tear my tight little bottomhole. It felt terrible, my asshole opening up wider than ever before. Then I felt the cool air of the room entering my opening that was so widely expanded. "No more PLEASE!" I begged, “It REALLY HURTS!” I screamed.  I was deathly afraid that HE would tear my anus and that I would bleed to death.

Sir Michael continued as my anus now was spread almost two inches wide, exposing a large pink gaping hole. HE ran HIS finger around the inside of my sphincter ring, letting me feel how open I was for HIM.

 

"A little more, Julie," HE announced as HE spread my anus a little more. Another squeeze and it was over two inches, with my inner tract exposed to HIS gaze. HE could actually see deep inside of my anal opening.

My tears were flowing freely from my eyes as my anus burned from the stretching. I felt his fingers encircle the rim of my stretched anus. Suddenly a sharp pain erupted from inside of my asshole, and I cried, as my rectum began to spasm. I heard his voice, telling me that it was almost open two and a half inches wide. The burning pain from my asshole radiated throughout my whole body, and I just sobbed, wanting the pain to stop. I jerked in pain as Sir Michael locked the speculum open, a sudden pain shooting out from my painfully spread anus. "OOOOWWWW, PLEASSSSSE" I cried, as I could really feel the pain from my terribly dilated anus.

I looked back through my tears, and Sir Michael had a look of awe about him as if he had never seen an asshole so spread as mine. It left me open wide for HIS pleasure, with very little interference from the speculum. Then HE took a little dab of the ointment and placed a little bit around the rim of my anus. Playfully HE ran his finger around the outside of my anal pucker, continually feeling me squirm as my tender anal ring suddenly began burning from the ointment.

"OOOWWWW, MY GOD, Sir.  What is that stuff? It burns so much!," I cried.

 

Sir Michael showed me a tube of Ben-Gay liniment and said, "I warmed up your anus with a little bit of this warming ointment, Julie. Now lay still, my sweet girl, while I rub a little bit of crème around inside of your asshole."

 

"No please, NOT that," I cried, as I had already felt the pain from the heat of the Ben-Gay on my anal rim, and now he wanted to rub it on the inside of my anal tract. This would be much worse on the inside of my tender anal tract, and I couldn’t believe that he was doing this terrible thing to me. I know I had been naughty before, but this was just painfully cruel. I cried loudly, but despite my pleas, he applied the crème around the mouth of my anus and then rubbed some down inside. At first it felt cool, but then suddenly I jerked and squealed out loudly, "AAAGGGhhhhh GOD! OOOhhhhhh, PLEASE, SIR! OOhhh, it burns terribly. OOOhhhh, PLEASE wipe it off."  Cuffed as I was, I could do nothing but wiggle and move my ass around, as the Ben-Gay burned on my sensitive exposed and tender inner flesh. It felt like fire in my hole, and I was sure that it would permanently harm me.

Sir Michael laughed, and then released the speculum, watching as my asshole slowly decreased in size and spasmed from the heat of the Ben-Gay. After a few minutes it was still open over a half an inch, refusing to shrink back to its tiny former self, while the Ben-Gay still burned on my sensitive anal rosebud and inner tissues. I felt my anus gaping open and knew that little rosebud would never be the same again. I also knew that soon it would be stretched to my limit, as it would be wrapped around Sir Michael’s massive 8” cock.  I shivered with fear as a burning ache lingered from the Ben-Gay on my tender anus opening.

 

Sir Michael walked around the desk and lifted my face and kissed me on the lips. I felt a rush of passion inside of me for this man. I knew he was hurting me, but yet I wanted him to love me. I was willing to suffer a little for him, but I needed to know why he wanted to hurt me. “Why?” I asked.

 

He lifted my pretty face and kissed me again, and said, “You know why, Julie. I am training you to accept anything that I desire from you. I desired to see you whimper and wiggle for me with the Ben-Gay burning your anus. It causes no permanent harm, but trains you to be accepting of my desires. Now relax, Julie, and feel the warmth that I have for you. You please me very much and you did a wonderful job of passing the first step, and I’m proud of you!”

Chapter 5 -Sphincter Training

"You've been a very good girl, Julie, and we are almost done for the day. I know it hurt you when I stretched your tiny asshole and put Ben-Gay on it, but you must endure it so I won’t hurt you when I sodomize you. I know that you want to please me, Julie. You do want to please me, don't you?"

My tear stained face looked up at him. I had already endured so much. How much more could he want from me? "Yes Sir, I want to please you. I will endure whatever you do to make me ready to satisfy and please you, Sir, but please be gentle with me!" He released me from my bindings, but left my cuffs on and gave me another kiss on my cheek.

 

He smiled at me and then walked over to a soft leather couch that was on the side of his study as I just lay exhausted across his desk.

"Come over here, Julie," He ordered. He watched me rise and slowly make my way over to him. He pointed to the couch, and told me, "Julie, I want you to lie down on your stomach over the end of this couch, but first I want you to remove all of your clothes. We have one more training session to go through.

 

I slowly unbuttoned my skirt and then my blouse. Next I unlaced my chemise and pulled it over my head. I stood in only my socks and was about to remove them also, when he said, “Good girl, those are OK to leave on.  Now lie down for me." The couch wasn’t really long enough to fully lie out flat on, so I knelt over the end of it, pushing my ass out at him. He used little chains to refasten my cuffs to the floor on either side of the couch. I knew this was going to hurt me again, or he wouldn’t have fastened me down again.

 

I also knew that in this posture, my red and swollen asshole was peaking out at him, and my hairless pussy was still dripping with my moist dew. He helped me to lie over the rolled end, and then adjusted my legs, spreading them wide, so my pussy and asshole were gaping open again for his gaze.

"Flat on your stomach, with your bottom up, Julie, That's good," He said, patting my ass cheeks. Now I am going to start your next lesson in a minute. You're going to be good for me, aren't you, Julie? Otherwise I will have to spank you again, and I’m sure you don't want me to do that, do you!

"What are you going to do to me?" I sniffling, tears in my eyes again.

" I told you that I enjoy sodomizing a young girl’s ass like yours, Julie, but you have to be able to please me with your asshole, as well. I don't want to just fuck my cock in and out. No, I want you to pleasure my cock. You want to please and pleasure me, don't you, Julie?"

"Yes, Sir." I sniffling again, "How do I do that?

"That is what I am going to train you to do now. I am going to help you to know how to pleasure my cock. You'd like to learn that, wouldn't you, Julie?" He watched me as I nodded. Then he said, "You are going to have a “sphincter training” lesson. I will teach you how to grab my cock with your sphincter muscles and milk it until I cumm.. It will be very pleasurable for me and will give you pleasure also, knowing that you are making me happy.” He stroked my hair tenderly from my face, and even wiped a tear from my cheek.

 

"You look very beautiful, Julie, but I need you to open your legs a little more. You are going to have to spread them wide for me. I know you can do that, Julie. Can you open up wide and show me that cute pink asshole?"

 

I opened my legs and pushed out my ass, but he requested, "More, Julie, spread them real wide. Spread your legs all the way to the edge of the couch.  Yeah, Julie, that's so much better. Real nice, Julie, now I have such a nice view of your cute puckered asshole and dripping pussy." He walked around me and his hands began caressing over my upturned ass cheeks. He grabbed a small pillow, tapping lightly on my side, and said, "Lift up and put this pillow under you. Yes, way down. I want you to raise your ass up, just a little tiny bit.”

 

I felt him lifting my ass up higher then the rest of my body, with the pillow keeping my rear elevated up.

"Such a pretty face. Turn it so that you are looking back at me.’ He said, stroking my cheek. “I want to see your face, Julie, as I train your sphincter." He walked over to the table, and returning with a big pink butt plug. It was medium length, about six inches long, with a skinny tip and a pear shaped body that gradually got bigger until it narrowed at the base. It looked like a fat pink pear with a narrow base and had a bulb hanging down from it.

 

"This is your new butt plug.” He said, “The tapered end goes into your asshole to help stretch it out, and you already know how that feels. It gets bigger and then begins to shrink down in size until your asshole closes around it. The large end prevents you from pushing it out, so it seals itself with no escape. I can inflate the out part of the plug so that no matter how hard you try, you cannot push it out."

He lubricated the butt plug and placed it against my exposed asshole, making sure that he played with me before he pushed it in.  I gasped a breath, holding it, gritting my teeth as my asshole slowly stretched wide to willingly accommodate the tip. Wider and wider, the butt plug stretched me as he pushed it in, slowly expanding my asshole in an effort to help me accept the big plug. "PPHHooff," a whoosh of air escaping from my asshole as suddenly my sphincter ring grabbed onto the base of the plug, and sucked it in, trapping it tightly inside of me. I felt stuffed, with my little asshole now stretched to the max to accommodate the big pink plug. Slowly he began to pump the inner lining so that I would be truly full.

 

When he finished, he asked, "Now that wasn’t so bad, was it, Julie?” "Well, No, Sir, but my sphincter has a little burning sensation yet." I answered, moving my feet a little, while my sphincter spasmed due to a slow burning sensation as it adjusted to the stretching.

"Let me tell you about this butt plug.” He said.  “I want you to squeeze your butt cheeks tightly so your sphincter grips onto it.  Now try it, Julie, and show me how well you can do it."

I tightened my asshole, trying to grip the unyielding plug inside of me.

"Again, do it again for me." He said.

I did it again. “That's not so bad. I can do this.” I thought. A little snug for my asshole, but he had already done worse things to me then this.

"Now what I want you to do is grab the butt plug for five seconds, let go of it, grab it again for five seconds then let it go. Can you do that, Julie?”

 

“I’ll try, Sir Michael”, I whispered. He watched my expression, seeing me grind my face as I squeezed it and then let it go and then repeated the exercise again.

"Very good, Julie," He said, sitting down near my face again. "Now the hard part, Julie. I want you to do that every twenty seconds. Squeeze for five seconds, release and then squeeze for five seconds again. Wait twenty seconds and start all over again. Can you do that?"

"How long do I have to do this?" I questioned.

"You have to exercise and train your asshole for an hour!"

"NO,” I protested,  “I can't do that, not for an hour. How about just for a couple of minutes." I whined. He smacked my bottom, and said, "In order to train your sphincter, Julie, you have to do this for an hour. You're a big girl now and I know you can do it."

"OK, Sir, I’ll try," I answered. "Begin now, Julie, and don't forget, every 20 seconds, clench for five seconds, release and clench again for 5 seconds, wait 20 seconds and start again." He reminded me.

He watched as I began, seeing my ass cheeks clenching, unclenching and then clenching again. He must have known that I would slow down, because everything was fine for about five minutes, before I yelped in pain.

"OOWW, What was that for??" I shouted. I felt a sharp pain on my ass, as he spanked me hard. "OOWWWW," I yelled again. "Please stop."

"Julie, I told you that you would have to grip the butt plug for five seconds, release it, grip again for five seconds and then wait for 20 seconds before starting again." HE laughed out loud, "You were cheating, and the effectiveness of the butt plug depends on you upholding your part of the training. Now do it like I told you to!"

"OOOOW,” I squealed, as he spanked me again. Now pay attention, Julie," He said, slapping my ass hard, making me jump.

I gritted my teeth and gripped the butt plug tightly with my sphincter, counting to myself for the five seconds. Then I released it, and did it again. When the five seconds were up again, I counted the twenty seconds. It seemed like only a few seconds before I had to grip the butt plug again. I began to grunt as I gripped the butt plug, my sphincter grabbing tightly onto it. “How am I going to do this for an hour?” I thought.

 

I counted out the twenty seconds again, with my face contoured in pain as I struggled with all of my energy gripping the unyielding plug expanding my tight asshole.

Sir Michael looked at me, watching the expressions on my face as I continued to tighten my sphincter on the hard rubber plug. I hoped that all these efforts would be worth it and that I could satisfy HIM as I attempted to please HIM.

Suddenly my anus spasmed and my bottom filled with a sharp pain. "NNNOOO, now what, it burns?" I screamed as I felt a burning sensation in my asshole, spreading from the butt plug and slowly radiating all around my tight anal tract. “It is just the loosening up of your tensing anal muscles.” He said. “They spasm around the plug, kind of like a cramp from over exertion in your arms or calf muscle. Just relax a moment, and they will soon go away.” 

Slowly it began to subside, and I gripped the plug as tightly as I could and then released it, beginning my training again. I could feel my anal muscles tighten around the plug, and knew that if it were Sir Michael’s cock, I could squeeze his juices from him with no trouble at all. He watched me tighten and release, but my timing must have been off. He smacked my bottom and said,

"You must pay attention, Julie. You have to both grip it tight and also release it at the right interval." Sir Michael sat down on the couch beside me, making sure that I was gripping and counting properly. "There, there, you can do it Julie," He said, as his hand began stroking my ass cheeks. He could feel my butt muscles tighten, knowing that I was gripping the butt plug as I was supposed to.

I felt his fingers running up and down my ass crack, and felt them bump up against the butt plug buried deep inside of my rectum.

Sir Michael traced his fingers around my swollen and enlarged anal opening, which was stretched wide to accommodate the massive butt plug trapped inside of me. "Tighter, Julie, grip it tighter," He said, feeling my ass muscles clenching and unclenching. "Yes, that's a good girl, I know you can do this. It just takes a little while for your stretched anal ring to get used to this activity. You are gong to get lots of practice doing this on me, so I want you to be prepared properly. I know you can do it, and I know you want to please me with your sweet little bottom, don’t you, Julie?" I nodded in submission, and said softly, “Yes, Sir, I do!

He stroked my face and said, "You're doing well, Julie, I can see you are trying hard, and doing well. I am really going to enjoy opening you up to the joys of sodomy, my dear Julie. I’m going to enjoy it immensely!"

 Sir Michael's hands ran up and down my flanks, feeling drops of sweat beginning to form from all of my exertion. It had only been thirty minutes, and I had so much more time to go. Sir Michael placed his hands on my hips and began helping me with the rhythm. He watched my ass clench, with a slight pulling up, and then I relaxed and arched my back. It must have looked almost like I was fucking the butt plug inside of me.

I felt him get up and move back behind me. I knew how exposed I must look to him, with my legs spread wide and my pussy open. I could feel the wetness between my legs. I began to pump my hips up and down, as it seemed to relieve some of the cramping of the large butt plug inside of me and the burning had subsided, too. I knew how it must look, but I knew that soon he would be doing this to my spread anus, for real. I imagined that it was Sir Michael inside of me, making me fuck his big cock. I imagined myself being forced to squeeze and pump his powerful tool with my newly trained sphincter muscles.

 

I jumped when I heard a knock on the door, knowing that anyone at the study door could see my totally naked body. "Don't answer the door, please.” I begged. Sir Michael was already at the door, opening it, with the outside light shining brightly into the room, my naked body was in the direct view of the door. I noticed that it was Doctor Brown.  I tried to get up, but I was restrained and wiggling was useless as I was totally on display and only looked more wanton and lustful.

 

"AAAAAHHH, the butt plug sphincter treatment in her rectum,” Dr. Brown snickered. I struggled, but to no avail. Suddenly Sir Michael spanked me with his crop. "What do you think you are doing," He said, slapping me hard on my ass, and pushing me back down. "You're not finished yet. Anyway, the good Doctor has seen your pretty ass before."


"Now Julie, calm down and continue your training, or you're going to scare the good Doctor into thinking you are sick or something. Why he might even have to give you a series of enemas, to help you if you continue to act up." He said, as he stroked my face after pushing me back down onto my stomach. He could hear my groans, knowing that I was struggling to grip the butt plug.

 

"Now pay attention, Julie." Dr. Brown whispering into my ear, "Get back to squeezing and releasing the butt plug with your sphincter muscles so that you will be able to accept Sir Michael’s manhood into your bottom." He saw the muscles in my ass contracting, knowing that I had begun to grip the plug again. "Good girl, now continue to practice like that, until your time is over."

Sir Michael stroked my ass cheeks and then dipped into my soaking pussy lips, as I continued to practice my sphincter lessons. Then he pulled his fingers out and pushed them in front of my face, rubbing them over my lips. "Lick them clean for me. Taste how sweet you are, Julie. " He watched as my tongue darted out tentatively, licking the salty cream from his fingers until he finally pushed his fingers into my mouth. My lips then wrapped around his big fingers tightly as I sucked them, just like I had done to his big cock.

 

Chapter 6 – A Price To Pay

 

Suddenly, I heard another knock on his study door. Sir Michael told Dr. Brown to open it, and I stayed put this time, having learned my lesson from the last time. As the door opened, I blushed in shame as I saw my little sister Jamie enter the doorway. She hesitantly walked with the Doctor over by me, and said, “Julie, you’re naked and what is that thing sticking out of your bottom?” I buried my head in shame, and couldn’t answer. Finally Sir Michael turned to Jamie, and said, “Julie is being ‘sized’. It is necessary for her to be trained and exercised in her bottom so that she will be able to please me with her tight little bottomhole, and you will soon also have this done to your sweet little bottomhole, Jamie! I’m sure the good Doctor explained to you about retaining your sweet maidenhead, but then proceeded to educate you in how to pleasure a man orally while he was in your room, didn’t he?”

 

Jamie was stunned and submissively hung her head and weakly said, “Yes Sir, he did.”  He looked Jamie in her pretty blue eyes, and asked, “Did he make you swallow his essence, too?” Jamie blushed brightly and shivered as she thought about swallowing the Doctors cumm. Then she softly whispering, “Yes Sir, he did, and I choked on it, too!”

 

“Then I guess the Doctor and I will have to give both of you more practice, so that you both get used to swallowing a man’s juice without choking on it. As for you, Jamie, we will begin your anal training in my study tomorrow!” Jamie shivered and trembled in fear as she thought about exposing her tight bottomhole for the same training that I was undergoing now.

 

I turned to him and imploringly begged him, “Please Sir Michael, let me be your “anal servant”, but spare my little sister.” He slapped my bottom, and said, “No Julie, you both have a ‘Price To Pay’ and both of you are going to be trained to pleasure me with your tight little bottoms as well as your mouths.”

 

Suddenly, I looked at the clock and realized that my hour of sphincter training was over. My bottom ached from the squeezing and from the repeated smacks. Sir Michael began rubbing and massaging my cheeks, making me feel loved and wanted. I breathed out, “UUUmmmmmm”, as his hands stroked and massaged me. I no longer cared about other people watching. I only cared about his hands and what they were doing to me. I loved his touch. After several minutes of having Sir Michael massage me, the Doctor stepped forward to inspect my bottom and anus, and after tickling my anal ring briefly, he quickly pronounced me in fine physical shape.

 

Sir Michael then helped me up, and told me to leave the butt plug inside of my anus for the rest of the day. He said that it was necessary to stretch me and to continue my preparation for sodomy. He called it “sizing me” and then he told me that I was going to spend the night with him in his room. I trembled and quivered as I thought about what he was going to do to me. Then he handed me my clothes and ordered both Jamie and myself to go to our rooms, wash up and prepare ourselves in dresses, for dinner with Doctor Brown and himself at 5 pm.

 

Chapter 7 – Dinner with Master

 

After getting dressed, Jamie and I walked to our rooms, I found it rather difficult to walk ladylike with that big butt plug stuck up in my bum. Jamie followed me to my room, and asked me if she could look at my bum and the butt plug again. I agreed, and bent over the bed as she lifted my skirt. She gasped in dismay, as she stared at how dilated and stretched my little bottomhole is.

 

“Julie,” she asked, “Does it hurt much to be prepared for him like this?” I stood up and turned around to face her. “Jamie, we are in Sir Michael’s debt and owe him a lot for rescuing us. He has willingly offered to take us in as his “wards”, and feed us and clothe us and care for us. Personally, I think we are more like his private little sex slaves, but I have willingly accepted our fate for the next few years with Sir Michael. I have allowed him to do things to me, like touch me, and finger me, and spank me, that I never thought I could or would allow anyone but my husband to do to me. And yes, Jamie, it did hurt to be prepared like this. However, we have a dept to repay, a beautiful home to live in, and a man who cares about us very much and someone with money to look after us. I was willing to submit to him, and Jamie, you will be willing to submit too. You willingly are going to bend over and allow him to spread your sweet cheeks to do the same things to you. We are his property until we turn twenty one, and there is little that we can do, but accept it. I am glad that he has respected us enough to save our frontal virginities, even if he has violated us both orally and plans to take our bottoms. Anyway, he and his cousin, the Doctor, are very handsome men who I really don’t mind getting a little sexual education lesson from. Things could be a lot worse for us. So get used to the fact that we are going to be his little playmates, Jamie, until we are ready to leave here.”

 

Jamie looked at me puzzled, and said, “I understand the playmate thing, Julie, but did you say that the Doctor is his cousin?” “Well, that is what he told me in the study, so I assume it is true.” I responded. We got talking so much about them, that we lost track of time, and suddenly we looked at the clock, and realized that it was just a few minutes before dinner time. We needed to wash up, so we hurried to the bathroom to get prepared. Then after washing, fixing our hair, and perfuming our bodies, we quickly dressed in two of our best dresses. We wanted to look very nice for both of them tonight. After helping each other get laced up, we both slipped on our shoes, and hurried down the stairs to dinner.

 

Sir Michael and Doctor Brown were waiting for us, and I could tell that we were in trouble. “Both of you are late!”, Sir Michael scolded us. “We will deal with that issue after dinner. As for now, Jamie, you sit next to Doctor Brown, and Julie, you come over and sit next to me.

 

Jamie and I quickly moved to our appointed locations next to the two men. Carlton and Collette served us a full four course meal, with soup and appetizers, fresh vegetables and fruit, the main course was leg of lamb with a baked potato, and finally dessert. It was far more than either my sister or I could eat, but it was wonderful to be treated like such honored guests. We were treated to a glass of fine Chardonnay, and we both felt like little “princesses”. After dinner, Carlton and Collette cleared the table and then Carlton asked if there was anything else that their services would be required for.

 

Sir Michael said, “Yes Carlton, I’d like you to go to my study and bring back two sets of wrist cuffs for our two naughty girls who were late to dinner.” Suddenly our fairytale dinner was turning into a disciplinary session, and both of us were afraid. Carlton left, and within a minute, he had with him two sets of fleece lined leather cuffs. Doc Brown and Sir Michael quickly wrapped them around our wrists, and laid two long cushions across the table. They then bent us over the table, and Sir Michael moved a lever under the table, which opened the table up and produced two sets of wrist-sized stock like apparatus. They opened them up, and placed our cuffed wrists inside. Then the bar was lowered across our wrists, and we were positioned, stretched and restrained, all at one time. Next, our dresses were lifted, and our frilly drawers were displayed for their viewing pleasure.

 

Doc Brown and Sir Michael discussed our chastisement, and finally decided on two smacks for each minute that we were late and a good frigging afterward for each of us. Since we were ten minutes late, that meant twenty smacks with whatever instrument they chose. Jamie and I watched, as Sir Michael walked to the corner of the dining room, and removed two long whippy birch twigs that had been peeled and prepared in advance. It was as if they had this disciplinary session planned long before we arrived late.

 

I don’t think that Jamie knew what we were in for, since she hadn’t been spanked very much in her younger days. I however had received the birch once from Papa and once at school, and I knew that it stung like fire. Papa had only given me three cuts, but the time at school, I had gotten six strokes, and it left me crying like a baby. How on earth could we endure twenty such lashes from these men?

 

They moved behind us, and then Sir Michael said, “Ladies, you have both been naughty, and were late to supper this evening. This lesson is not intended to harm you, but rather as a discipline to help both of you to remember that I like punctuality and that you had best be on time in the future.” Suddenly, our skirts were undone and dropped to the floor, as we were left standing in just our drawers. They stroked our bottoms and fondled us to their pleasing. They rubbed our cheeks and teased our pussies, and then stepped back. Suddenly, SWOOSHH… SWOOSHH…, both Jamie and I got a cut from the birch across our panty covered cheeks. It took a second for the burning sensation to hit us, but then Jamie and I both screamed out “AAAAAGGHhhhh”, as the burning sting registered on our bottoms. SWOOOSHH… SWOOOSH.., we each got another cut. We both screamed and echoed each other’s voices. This scene continued for twenty times, as our panty covered bottoms were literally lashed with lines of fire. Even though they offered little protection, I was glad I hadn’t forgotten to wear my drawers this evening. Our bums had been lashed severely, and they burned like nothing that either of us had ever encountered. Restrained as we were, we could do nothing but dance for our esteemed gentlemen, as they birched and disciplined our exposed buttocks. After the twenty strokes had been administered, we both just lay crying in our restrains across our pads that covered the table. The burning sensation was terrible, as if my bottom had been scorched with fire. Suddenly, I felt my panties being bunched up in my crack, and then slit with a knife as Sir Michael tore open my panties. His hand quickly slipped inside of my torn material, and he cupped my dripping slit. His fingers played with my pussy for a moment, and then he pinched my clit. I jerked wildly! I didn’t realize how wet I was until his fingers started playing with me. “You’re soaked, Julie! It’s obvious that a good spanking stimulates you sexually as well as mentally.”

 

It was very obvious that the spanking had literally made me soak myself. I felt so ashamed, as he fingered and rolled my stiff little love bud, driving me wild with lust and desire to cumm for him.

 

Doc Brown was doing the same thing to my sister, and through her sobs, I heard her gasps, as he too found her clitoris. His fingers were teasing and rolling her tender little love pearl, too, as she jerked and gasped at every touch. As Sir Michael frigged my clit, I listened to my sister, as her gasps and panting increased just as mine did. Suddenly, I felt myself stiffen up and a heat wave rolled through my body as through the pain, I was forced to cumm for Sir Michael. My body spasmed and jerked as wave after powerful wave rolled through me. Gently, he continued to wiggle my clit, until I had fully cumm for him, and my tender love bud could hardly stand anymore touching. Almost immediately after I had finished cumming for Sir Michael, Jamie squealed out in bliss, as Doc Brown frigged her love pearl, and brought her to an orgasm, too. After both of us had climaxed and had been made to cumm for our gentlemen, we heard the unzipping of trousers, and fear overtook both of us. Restrained as we were, we had no protection, and we both thought this was the moment that we had feared would soon happen.

 

Suddenly, sliding under my bottomcheeks and wiggling under my quim, I felt Sir Michael’s cock. It stroked back and forth across my pussy lips, making me shiver and making me wetter, as my juices rubbed onto his moving cock. Doc Brown had done the same to Jamie, and when she gasped, “AAAhhh!”, I thought she had been penetrated. “”OOOhhhh, Sirs!”, I protected. “ I thought you had said….!” SMACKKK…. SMACKKKK…. I never finished my sentence, and both men gave each of us a few SMACKKSS on our stinging bottoms. “BE QUIET, Julie! Both of you both belong to me, and I will do with you as I see fit! I am more than your Guardian, girls, I am your MASTER!”

 

It was the first time he had ever said “Master” to us, and I knew he meant it. We truly were his lust slaves, and we were required to do as he wished. He placed the tip of his cock against my anus, and wiggled it. I gasped in fear as I thought I was going to have my cheeks split right then and there. “Tonight Sweetie, you are mine!” He said. Just as I had resigned myself to be taken, both men removed their swollen cocks from between our legs, and walked around to release our wrists from the cuffs.

 

As Jamie and I still lay across the table, the men went over to the sofa and sat down. They motioned for us to come over to them. With our bottoms still stinging, Jamie and I walked over to our Master’s and stood in front of them. “Girls, I wish to hear your apologies for being late to dinner, and then both of you are going to show your repentance and submission to us by kneeling between our legs, and servicing our swollen lances. Jamie and I both hung our heads, and then I said, “I’m sorry Sir Michael and Doctor Brown for being late to dinner and for making both of you wait for us. Please forgive me!” Jamie quickly repeated my apology, and then we both knelt between the spread legs of our men.

 

I softly grasped Sir Michael’s cock with my hand and fed it into my mouth. Jamie did the same for Doctor Brown. After only a few minutes, I had Sir Michael gasping and groaning with pleasure. Suddenly, Sir Michael grabbed my hair and thrust deep down my throat, as he began pumping his salty load down my throat. This time I was a little better prepared for his juices, and I did a very admirable job of sucking and swallowing all of his warm essence. Within seconds of milking Sir Michael dry, Doctor Brown grabbed Jamie’s pretty blonde hair and began pumping his seed down her throat. She sucked and gulped, and gagged, as Doctor Brown flooded her throat with his cumm. After we had finished, I almost felt rewarded, and said, “Thank you, Sir, for allowing me to ask for your forgiveness, and to allow me to service you was my pleasure.” Jamie picked up on my cue, and repeated similar words of appreciation to Doctor Brown.

 

They both smiled at us and Sir Michael said, “Doc, look how quickly they learn their appropriate place in my household. I think that they are going to be excellent assets around her. OOOhhh, and Jamie, Doctor Brown is going to spend the night with us, and you are going to be his bedroom guest for this evening. Be nice to him and behave, doing everything he asks of you, or your bottom with feel the birch again. Julie, you are going to be with me tonight, so when we are done here, go to my room.”

 

Chapter 8 – First Night with my Master

 

Jamie gave me a scared little schoolgirl look as we touched hands and said goodnight, not sure what lay ahead for us. Doctor Brown handed Jamie her skirt and escorted her to his guest room, while Sir Michael asked me to stay a moment, before I go to his room. After they had left, he walked over to me and after stroking my face and running his hand through my golden hair, he held my arm and said, “Julie, I want you naked and kneeling on my bed with your head down and your ass raised in submission to me when I arrive in a few minutes. The only thing I should see is your adorable ass with the butt plug still in place when I arrive. Be sure you wash up and are waiting in the correct pose of submission on top of my bed, or your bottom will feel my wrath, again. Now go get ready, young lady!”

 

Although I was terribly fearful of what was going to happen, I knew I had no choice, and needed to obey his instructions. Having him call me a “young lady” sparked an appreciative moment for me. I grabbed my skirt and hurried off to his room. It was so big, and never having been in it before, I was greatly surprised by his choice of décor. It was a beautiful forest green room with accents of a soft cranberry or wine colored draperies and accents. Candles were already burning in there, as if I had been expected. Maybe Carlton or Collette had prepared the candles while we were being disciplined and sucking cock downstairs. I don’t know?

 

In the corner of his room stood a leather padded spanking horse. Fear gripped me, as I suddenly remembered his words, and quickly stripped out of my torn drawers, and went to the bathroom to wash up. After freshening up, I returned to the room and looked at the stripes that the wicked birch had left on my reddened cheeks. The pain had subsided, but my cheeks radiated a glowing heat. They were very tender, and not wishing to receive any more, I quickly climbed up on his bed. I positioned myself so that as he walked into the room, he would see my ass and the butt plug which was still inside of me. I had my head up by the pillows, and my ass pointed toward the door. Then I waited for his!

 

Click..click..click, I heard his footsteps coming down the hall and knew that my asshole would be sacrificed to him, before the night was over. I had resigned myself to him, and was ready, willing, and able to offer my asshole to him, or to let him take it by force. I was his “Cherry Slave”, and I knew it! He opened the bedroom door and walked over to me. His hands softly massaged my buttocks as he said, “Julie, I am going to have to give you a couple of enemas tonight. They will clean out your back passage, and prepare you for me back there. Now just relax while I remove your butt plug, and then I will begin with your cleansing.”

 

I felt his fingers on either side of my anus as he gripped the big plug and slowly removed it from my rectum. I could feel how exposed I was and knew that my asshole must be gaping wide open for him. He left for a few minutes, and then returned with a large red rubber water bottle with a thin hose connected to it. He had a stand that he hung the water bottle on, and then he moved to my side.

 

While still kneeling, I felt some smooth oil or lubricant being reapplied to my anus. Then suddenly, I felt a cold hard metal nozzle as it nuzzled into my bumhole. It spread my sphincter muscles again, and easily slid right in. The hose was somehow attached to this nozzle and I didn’t know why, until he opened a valve on the nozzle. Suddenly warm soapy water was squirted into my anal cavity. I gasped loudly at the intrusion into my little bottomhole, because it startled me and began to hurt me slightly as it filled me with water. Now I knew what an enema was, and knew why he was giving it to me. He emptied the bag into my bottom, all the while massaging my cheeks and even tickling my quim. It actually felt strangely good and erotic, until the cramping began.

 

“PLEASE, SIR!” I begged, “May I go to the bathroom? It really hurts!” With my bottom still plugged, he made me wait for a few minutes, and then excused me to go pull the plug and vacate my bowels. He told me to wash things off, and to return to him for a second cleansing. When I returned to him, I had washed the plug off, and placed it into his hand. Before he started again, he massaged some cool soothing lotion onto my buttocks, which felt very good and took away most of the remnants of soreness from my birching.

 

He positioned me again, and filled my rear passage with another bag of warm water. He made me hold it for a while, and then allowed me to go. When I had been thoroughly cleansed, I returned to him and he looked into my big blue eyes, and asked, “Well Julie, are you ready to offer me your tight little bottomhole for my pleasure?” I hung my head and softly said, “Yes, Sir! I am yours to love, however you want me!”

 

I think it must have been what I said, and how sincere I was in my surrender to him, because he took me into his arms and held me close. Then he whispered in my ear, “I’m glad you have decided to surrender yourself to me, Julie. I do “love” you and your sister, and know that you both will be better off doing things my way.” After he had hugged me, he rolled back the covers, and bent me over the side of the bed with my bottom toward him.

 

He took a tube of lubricant and generously anointed my puckering little hole. He squirted some of it up inside of my anus, too, and then he said, “Julie, having trained your tight little puckered ring, I expect that you will be able to milk me and squeeze my cumm straight out of my balls and into your receptive ass. Now reach back and spread your pretty cheeks, and show me that asshole that you want me to take.”

 

I knew my time had come to surrender my bottom to him, so I reached back, spread my buttocks, and offering him a perfect view of the tight little tunnel that he so desperately wanted. Then he said, “Julie, it’s beautiful, and you’re beautiful, but I want you to ask me to take the maidenhead of your ass.”

 

His words made me freeze. I thought he was going to force me, to take my anal virginity by force. Instead, this man wanted me to beg him to violate and take the maidenhead of my bottom. I guess I knew it was inevitable, so without wasting any more time, I softly asked, “Sir Michael, would you please put your manhood into my ass.”

 

“LOUDER!”, He commanded.

 

“SIR MICHAEL, WOULD YOU PLEASE FUCK my ASS?” I begged loudly. I said it so loud that I was afraid that the others in the house might have heard me. He chuckled and crouched behind me, as he placed the helmet head of his thick cock to the small aperture of my glistening anus. He rubbed the slippery cock over my asshole, nosing just his tip into the little opening. "Can you feel that, Julie? Can you feel how thick my cock is, and feel how big it is?"

 

Suddenly, I felt his tip slide into my sphincter ring. Then he pushed down with his cock, while he pulled my asshole open with his hands. I gasped out, “AAAAhhh,,,AAAhhhhh..” as he watched my asshole, slippery and tight,  slowly forced to spread wider as the crown of his cock began to stretch it open. “AAAhhh… AAAhhhh…”, I squealed, as the size of his cock stretched my little hole to unnatural dimensions. I gripped the covers with my hands and bit them with my teeth, to be able to endure my painful anal surrender.

 

"Push back with your asshole, Julie, like when you underwent your sphincter training earlier. You are going to have to allow it to stretch you open very wide. MY cock is bigger than the fingers and probes that you had inside of you earlier today, and it is going to go very deep inside you." He hunched forward, jerking his hips as he slowly allowed the head of his cock to stretch my tiny asshole.

 

Gripping the sheets tighter, I cried “OOOOhhh, Sir, AAAhhhhh… PLEASE!”
"OOOWWW,"I moaned again, as my asshole was stretched wider to accept his raging manhood. "PLEASE, it hurts," I begged, as I tried pushing back with my sphincter, hoping to relieve some of the pain. "AAAGGHH," the cock head now pushed my asshole open wider and wider. I lay over the bed, unable to stop the ravishment of my tiny virgin anus. "OOOOWWW," I screamed again, as Sir Michael's cock begin the painful entry into the depths of my asshole. He slapped my ass cheeks hard, and said, “You know you want me to do this to you, Julie, so don’t fight it. I know you want to please and pleasure me, and your tight ass feels so good. Now just relax, and open up, so I can fill you up.”

"OOOOOOWWww," I squealed, as the pain from his plunge was shooting up my spine as my asshole was strained and stretched to accommodate his big swollen member. My ass cheeks stung from the spanking he had given me, and the momentary stinging sensation allowed him the time he needed to force his cock deeper into my resisting asshole. I felt my sphincter clench and unclench on the head of his cock, attempting to practice my sphincter training on his swollen cock. "OOOwww, OOOwww, AGGGHH," I groaned, as his hands moved my hips from side to side, forcing my sphincter to massage his cock head as it pulled and nudged deeper into my stretched asshole.

"Yes, that’s a good girl, Julie! Your asshole tugs at my cock head so nicely. Move around on my cock, and nip it with your sphincter muscles." He said, as his hands forced my hips to sway back and forth. His eyes watched as my asshole gripped his cock, squeezing it to his great delight. I tried to let him feel my sphincter muscles clench on his cock head, as I had been trained. I knew he would enjoy me practicing milking him. He slapped my ass cheeks again, with the sound reverberating through the room. I clenched my ass cheeks in response, trapping his hard cock inside of my asshole and squeezing it so tightly. "Such a sweet tight asshole you have, Julie," He praised, as he slapped my ass cheeks again, making me tighten on his cock again.

I felt Sir Michael begin to pull out, but then he pushed forward with his cock again, plunging his thick love muscle deeper into my little hole. My asshole squeezed inside as he begin to push further into the depths of my asshole. "NOOO, DON’T GO SO DEEP,” I screamed. “IT HURTS!" Sir Michael’s strong hands and weight pinned me to the edge of the bed, as he slowly skewered me with his thick big cock. My asshole was stretched wide open, and spasmed around his cock head, as the walls of my rectum expanded outward to accept his bulbous tip. MY sphincter grabbed his shaft as it pushed in and out, gripping it tightly as if it were a rubber sleeve stretched around it.

 

"AAAGGGhhhhh, please, don't do this any more! Please, cumm in my mouth, Sir, but just don't put it in any deeper!" Suddenly, I felt Sir Michael quickly push another inch of hard cock into me, making me scream again as he hit the top of my rectum, but then he stopped. I felt him slowly pulling his big cock from my asshole, as a giant suction formed behind it pulling my insides out with it. "OOOhhhh, Yes, thank you, Sir! Please, take it out," I cried out in relief. I arched my back out, spreading my legs wider, anything to relieve the pain in my asshole as the hard cock pulled out. I felt my sphincter grabbing the head again, clenching onto it in a reaction to its exit. I slumped on the bed, waiting for it to pop out of my ravaged asshole.

 

Suddenly, he gripped my buttocks and thrust himself deep into my bowels. I gasped and went breathless, as he buried his big cock to the balls. My screams echoed in the room, “AAAAhhhh… NOOooot so deep! PLEASE! AAAAhhhh…,”  as he began pumping in and out of me. It hurt so fucking much! “You have it all, Julie! I’m very proud of you!” He proclaimed. Finally he stopped pumping, and bent over my back and said, “Julie, you have done well for your first anal experience. Your tight bottom will loosen in time and with practice, and you will cumm to enjoy pleasuring me. Now grip my shaft with your sphincter muscles, and milk me of my cumm with your asshole, as you have been trained.”

 

Fighting through the subsiding pain, I knew he must be close to cumming. I wanted to pleasure him and I wanted him to cumm inside of me, so I squeezed and relaxed my anus muscles over and over on his thick shaft. I was really working and getting all hot from my efforts, using my sphincter muscles, just as I had been trained to do with the plug. Suddenly he grabbed my hips tightly, groaning and thrusting his shaft deep inside of my ass again. His deep thrusts weren’t nearly as painful as before, as he breathed “AAAhhhhhh, yes, Julie! You are wonderful! “MILK ME”, girl!” He slumped over my back, as I felt his hot cumm squirt deep inside of my newly sodomized asshole. I could feel his essence flooding my bowels, as I continued to squeeze his cock with my pulsing anus. I was thrilled in the knowledge that I had actually accomplished the pleasuring of Sir Michael, my “MASTER”, just as he had wanted me to. My bottomhole was sore and ravished, but I totally milked his essence from his throbbing cock. After he was fully drained, he grabbed the butt plug and wiggled it back into my red sodomized bottomhole, trapping his copious fluids inside of my bottom. Then he turned me around and made me suck and lick his cock clean.

 

I tasted his cumm and our passion, and I could feel my anus spasming aroud the butt plug as it sealed my bottomhole, holding his cumm inside of me. I realized that he wanted me to retain his fluids inside of me as I was sucking and cleaning him off. He was happy, and I was happy that I had pleased him.

 

When I was done with him, he lifted me up and gave me a kiss and a hug. He looked into my eyes and said, “Julie, normally you will suck and swallow and drink my essence every day, starting with the rising of the sun, and ending whenever I last cumm in you for the evening. Tonight however, on your very first night of learning to be my anal servant, I want you to retain it inside of you until morning. You have done well, MY “little rosebud”, and you shall be rewarded for your efforts. I want you to know that I was delighted with your efforts, and plan to use your tight little hole frequently. Now go wash up and then return to me.”

 

I smiled up at Sir Michael, proud of my accomplishments, and then went to wash up in the bathroom. I soon returned, and crawled into bed next to him. He kissed my cheek and said “Goodnight, Julie. You were wonderful!”, as he wrapped me in his arms and held me close. I felt loved and wanted, and happy to be in my Master’s arms. His breathing got heavier, and soon he was fast asleep.

 

I lay next to him, my Master, feeling my anus still throbbing from my “anal awakening” by him and still filled with his sperm and the big butt plug.  As exhausted as I was, my thoughts still drifted and I wondered what Doctor Brown was doing in his bedroom with my little sister. Soon fatigue overtook me, and I too fell asleep next to Sir Michael.

 

Chapter 9 – The Morning After

 

The birds chirping outside awakened me in the morning, and I looked over at Sir Michael as he still slept next to me. He really was a handsome man, and I was glad that I was his. He moved a little bit, and then he opened his eyes and touched me. “Good morning, my “little darling”, how are you feeling this morning?” I smiled at him and softly said, “I’m fine, Sir, just a little sore from my efforts last night. I hope I pleased you!” He grinned and pulled me close to his chest. His hands squeezed my bottom and patted the plug that I still wore for him. “You were exactly as I wanted you to be, Julie, tight and terrific. From this morning on, I have a new duty for you to perform as soon as you awaken every morning that you are with me, Julie. I want you to crawl between my legs, and awaken me with your sweet warm lips wrapped around my cock. I want you to lick and suck me, and to make me cumm every morning, unless I tell you otherwise. Do you understand?”

 

I nodded and moved under the covers to my desired place between his legs. Then with my soft hands I grasped his morning erection, and wrapped my lips around it. I licked and I sucked on him for a long time, and he groaned and smiled every second of it. Finally, his fingers grasped my blonde hair and held my mouth in place as his essence pulsed out of his squirting member into my mouth. I sucked and swallowed every drop of his love juice, and he was pleased. Now I had his juice in both my mouth and my bottom, and I was full of his essence and pleased that I had satisfied him.

 

After I had sucked him dry, he had me prepare a bath for him. He made me bend over the commode, and he pulled the butt plug from my ass.  I quickly sat down and vacated what was left of his juices from my bowels. Then he climbed into the tub and he invited me into the tub with him to wash and cleanse him. He returned the favor to me, and we both had some fun doing it. I gladly accepted my new role as his personal assistant, and looked for ways to make him happy with me. I even helped him get dressed, something that Carlton used to do for him.

 

After we had bathed, he allowed me some time to put on my make-up and get ready for breakfast. Carlton had eggs, bacon, and muffins waiting for us as we walked to the dining area. I hadn’t seen Jamie yet, and wondered how she and Doctor Brown had gotten along last night. Finally as we were finishing, both of them came into the dining area. Jamie looked fine, and smiled at me as she sat down. I was afraid to ask her right then in front of the gentlemen, so I waited until we were excused to go prepare Jamie for her training session. In her room, I asked her about last night.

 

“So little sister, tell me what happened between the two of you last night? What did he do to you?” She smiled, and confessed, “Really nothing new happened last night! He fondled me and frigged with my clit until I squealed in orgasmic bliss for him again, but I liked that. Otherwise, he just held me and told me how pretty I was. He did tell me a little about my training scheduled for today, and said that he can’t wait until I have been prepared. He also fingered me back there while he was frigging me, and I must confess, it made me cumm twice as hard for him. How about you, Julie? Did he …..you know….take you back there last night?”

 

I looked at my sister, and remembering that her “anal training” was going to take place later this morning, I said, “Yes, he did, and he said that I pleased him very much!”

 

“So did it hurt, or what was it like?” She would find out soon enough how it felt, so I just said, “I made it my goal to pleasure Sir Michael to the best of my ability, and he loved and appreciated all my efforts.” That was enough to satisfy her, and so for the next hour, I helped her to get bathed and prepared to go meet with Sir Michael for her “anal opening and training.”

 

Chapter 10 – Jamie’s Opening and Training

 

Shortly before 10 am, Collette knocked on Jamie’s door, and told her that she was to go down to meet with Sir Michael and Doctor Brown in his study. Jamie was trembling, and said to me, “I know this is going to hurt, Julie, but I know I must endure it just as you did. Tell me that I’ll be fine!” she begged.

 

I looked at my cute little sister and knowing that she was about to undergo the same torturous stretching of her anus as I had endured yesterday, I held her hand, and said, “You will do fine. In fact, he might even like you more than me, because you are cuter!” She smiled and giggled at my last statement, as Collette led her down to Sir Michael. She was more like a sheep being led to the slaughter. I reached back, lifted my dress, and touched my swollen anus. It had hurt being sodomized last night, and I knew I was going to be used that way a lot by Sir Michael. It was an easy consession to make, considering that Sir Michael was letting me remain a legal virgin.

 

I remained in my room and started to read a book, as I waited and listened for the screaming of Jamie to begin as those big instruments were used inside of her tiny little brown hole. It didn’t take very long for the two men to get my little sister restrained and begin her anal opening with stretching and probing of her anus.

 

For over an hour and a half, Jamie’s cries and squeals could be heard throughout the house, as Sir Michael and Doctor Brown probed, lubricated, and stretched my sister’s bottomhole. I knew exactly what it felt like to be “opened”, and my heart went out to her. I knew however that once this training was accomplished, she would be required to have her tight anus stretched around a hard cock, just as I had last night. But, we had no choice and had to accept our place of servitude to Sir Michael. Finally around noon, they had finished and Jamie was sent to her room to rest for a few hours. I heard her enter her room, and I laid down my book and walked over to her room to comfort her.

 

As I entered her room, she was on her stomach, and under the covers, just sobbing. I knew that they had given her a butt plug to stretch her back there, and I wanted to see it. “Hi Jamie, I know you are hurting a little back there, but the hurt will go away, and it really isn’t so bad. I actually am proud of the fact that you and I can pleasure Sir Michael, and I’m sure you will be too.” I gently pulled the sheets back, and looked at her cute ass. They had spanked her some, as her bottom was hot and red. I opened the covers a little more, and saw a big black butt plug in her anus, similar to the one I had to wear. “OOOOhhhh, Sweetie, I know it burns and hurts now, but it will widen you back there so it doesn’t hurt so much when he sodomizes you later.

 

Jamie looked up at me and said, “Oohhh Sis, they really hurt me during the training, and then they said that they would both take my anal virginity this afternoon at 3 pm. I’m scared Julie, because I know it is going to hurt a lot worse that the training this morning. What am I going to do?” She lay sobbing into the pillow, as I sat on the bed next to her and whispered, “I’ll see if I can join you this afternoon and maybe spare you one of those lances, by taking it into my backside instead.” Jamie looked up at me and smiled, saying, “OOOhhh would you, Julie? I know if you survived, so can I, but two times on my first attempt is more than I think I can bear!”

 

I leaned over and hugged her, and assured her that I would ask Sir Michael if I could attend. She hugged me, and held me for comfort. I knew I had to let her rest, so after a few moments, I excused myself from her room.

 

I slipped back to my room and put on one of my fancy dresses. I knew I better look good if I was going to win Sir Michael’s favor when I presented him with my request about filling in for Jamie. After fixing my hair and making sure that I looked ravishing, I strolled down the steps to Sir Michael’s study. I knocked on the door, and waited for him to invite me in.

 

“Come in, please!” He requested. I quickly opened the door and walked in to see him. “Good Afternoon, Sir! I have come down here to make a request of you on behalf of my little sister.” He looked puzzled, and said, “Well, what is your request, Julie?”

 

“Well Sir, I know you are going to complete Jamie’s “anal awakening” this afternoon, and she had told me that both you and Doctor Brown were planning on taking her back there. What I was wondering was if I could persuade one of you to take me and spare my sister a double ravishing.” WOW, I thought. I actually got it all out. Sir Michael looked at me and said. “Julie, that is very noble of you to offer yourself in her place so soon after your own awakening. I like that about you. I would be delighted to have you attend your sisters anal deflowering this afternoon, Julie. After I have opened Jamie up, I will gladly concede her to Doctor Brown, and then reintroduce myself inside of your delightful rear passage. That is a marvelous idea, young lady! I also have some special lingerie that I would like both you and Jamie to wear this afternoon. It is a gift to both of you to show my pleasure and delight in having you both here with me. I picked it up a few days ago when I was in town. The pieces are in those two wrapped packages over there by the window.”

 

Doctor Brown picked up the boxes and handed them to me. “Make sure that both of you are wearing these outfits, and nothing else, when you report back here at 3 PM.” Sir Michael demanded. “Until then, you may go to your room and read, or rest, whichever you prefer.” 

 

I accepted the two boxes and thanked Sir Michael for being so generous and so understanding. Then I went up to my room and proceeded to open the box which was labeled for me. After tearing off the wrapping, I looked inside of the box, and there was the skimpiest looking set of lace corset, panties, garter belt, and stockings, all in fire engine red. I knew that dressed like this, Jamie and I would for sure get our tight rear rosebuds stretched and swollen before the afternoon was over. I looked at the lingerie for a moment and admired how pretty and sensual it really was. Sir Michael had impeccable taste, and was willing to share his wealth with us, by giving us this present. I was beginning to feel like a real woman, and was proud of my looks and desirability to Sir Michael. His sexual training of us was not something I would have asked for, but some unpleasantries, he excited me.

 

I removed my clothes, and slipped on the panties. Then I slid the corset over my head and moved it down in place. Since I couldn’t reach the ties in back, I’d have to ask Jamie to help me with that part. I next slipped on my red stockings, and admired myself in the mirror. I did look sexy! Finally, I stepped into the garter belt, and moved it to my hips. It took me a moment to figure out how the clips fastened to my stocking, but I quickly solved the problem. I walked over to the mirror, and took a long look at how pretty this lingerie looked on me. I wondered if this was the way that the Parisian courtesans dressed to entice their men. Then I lay down on the bed to rest for a few minutes, before I needed to get Jamie ready for Sir Michael.

 

I started thinking about Sir Michael and Doctor Brown, and wondered why both of them wanted to sodomize little Jamie. After all, Sir Michael had been alonr with me last night, and he could have Jamie alone with him tonight. But to want to do it this afternoon must mean that Doctor Brown must have a thing for my little sister, and so he wanted to do it to her, first. I looked at the wall clock and since it was only 1:15pm, I had a good hour that I could relax before he wanted us downstairs. I closed my eyes, and wondered what was going to happen this afternoon. My thoughts quickly drifted, as I recalled how things in our life had changed. Only a week ago, both Jamie and I had been pure untouched little virgins. Now both of us were Sir Michael’s “anal submissives”, and were quickly developing a fondness for cumming and sexual play. I don’t remember much after that, because I must have dozed off.

 

At 2:40pm, Jamie walked into my room and shook me. “Julie, get up! We need to get ready!” Not knowing what time it was, I threw the covers off and jumped from the bed. Jamie saw my new lingerie and with a jealous tone she said. “It’s 2:40, and where did you get those?”

 

I paused for a moment, and then stammered, “Sir Michael gave us each a new set of lingerie. Yours is still in the box. We have to hurry Jamie, if we want to avoid getting another spanking. Here, let me help you change.” She quickly agreed, and I helped her out of her clothes and into her new lingerie. I laced up her corset, and then she laced up mine. We touched up our hair, and then raced down the stairs to his study. We knocked on his door and were bidden to “Enter”, only moments before the big clock in the foyer sounded the three o’clock toll.

 

Both men smiled at us as they looked at us in our new outfits. Our breasts were flowing over the top of the corsets with our nipples prominently on display, and our pussies were already dripping wet. We knew we were his sexual servants, and we were willing to accept our roles. He led us over to opposite ends of the loveseat, and positioned us so that our bottom stuck out over the ends. He positioned us and told us to hold hands in the middle.

 

He then walked next to Jamie, and asked, “Jamie, tell me why have you come to my study this afternoon?” Jamie looked at me and they shyly said, “Because you have requested me to be here, Sir!” His big hand smacked her bottom, and she winced as he said, “Wrong answer, Jamie!” HE smacked her buttocks again and asked the same question. “Jamie, why have you come to my study this afternoon?” This time Jamie quickly responded with, “So you and Dr. Brown can take my anal virginity, Sir!” His big hand stroked her tender bottom and he smiled and said, “That’s right, Jamie! And we intend to open you up properly so that from this day forth you will be able to offer to me, or Dr. Brown, or any MAN, pleasure with your tight little bottom. We also have arranged both of you so that you can hold hands and comfort each other during this training. If for any reason, either one of you break your hands from each other, you both will be severely spanked and your sodomy will continue while you are bound over the table. We are going to give both of you a ginger suppository to help clean you out, and it may take a few minutes to work inside of you. While it is working, we expect both of you to hold hands as we prepare both of you. Do I make myself clear, girls?”

 

“Yes, Sir!” we answered, as we looked into each other’s eyes and knew that our anal openings were going to get a workout. Dr. Brown walked behind me, and Sir Michael walked behind Jamie. I watched as her panties were lowered and a ginger suppository was inserted into her anus. Then I felt Dr. Brown lower my panties and he slide a little ginger flavored white bullet into my anus, too. I’d heard of ginger suppositories before, but had never received one. At first I didn’t feel a thing, but then a burning feeling slowly radiated from my anus. The burning got hotter and stronger as Jamie and I suffered in preparation together. Both men massaged our bottoms and tickled our clits as the suppositories melted inside of our bottoms. It was like being caught between heaven and hell. The frigging of our clits was wonderful, but the burning in our bottoms was awful. For almost half an hour the two men tormented our clits and burned our bottoms. Finally the urge to go to the bathroom was quite powerful and I asked, “Sir, may I go to the bathroom?”

 

Sir Michael knew that the little suppositories had taken effect and then dismissed us to the privies. After going and then washing and flushing our bottoms properly with a bulb squirt, we both returned to the two men. We were repositioned over the loveseat and then our anal openings were anointed with a jelly-like oil. I watched as both of them worked on Jamie, stretching her anus and squirting warm oil inside of her bottom. She “OOOOhhhhh’d” and “AAAAhhhhhh’d” all the while they were playing with her bottomhole, working to stretch her little bumhole. While Sir Michael stretched Jamie’s anus, Dr. Brown frigged her clit to get her excited. Then Sir Michael made her suck on his cock to get it wet before he inserted it. She gladly sucked and wet it until he stopped her and asked, “Jamie, are you ready to surrender your anal cherry to me?” Jamie knew she had no other choice, and she remembered what I had told her she was willingly going to do for him. She stuttered a little as she said, “Yes, Sir, I am willingly yours!” He softly said, “Jamie, ask me to take your anal virginity!” She thought that he was just going to force himself into her bottom, but instead he wanted her to beg him to fuck her bottom, as he had done with me. After a hard swallow, she took courage and begged, “Please Sir Michael, Take my little bottomhole and fill it with your manhood!”

 

He was pleased in her offering as he touched the tip of his big cock to the quivering rose-like dimple of Jamie’s anus. He slowly wiggled it around and then slowly pushed inward as I held her wrists and hands tightly, making sure that she stayed put so that he wouldn’t thrash our asses again with those nasty birch rods.

 

Her eyes rolled in the back of her head and her mouth gasped as her tiny ass hole stretched to accommodate Sir Michael’s cock. After the initial burning shock of pain, her mouth opened wide and she squealed out loudly as the big helmet head squeezed into her tight little rosebud. “AAAAhhhhh, GAWD! NOOOOhhhhh, TOO BIGGGG, SIR. Slowly he eased his cock past her spasming clenching sphincter muscle and deeper into her ass hole. Sir Michael then slowly began to work the thick swollen cock in and out, plunging deeper with each penetration, as her squeals and cries rang out, OOOhhhhhh, NOOOoooo.AAAAhhhhhh. SLOWER, PLEASE! IT BURNS, SIR!”.

 

I held her wrists tightly, and looked into her pretty blue tear filled eyes. She knew her duty, but her expressions were mixed with the pain of being sodomized and stretched so widely and her desire to please him. Inch after inch entered her tight little ass hole as I continued to hold fast to her wrists. She was shaking with fear and sexual passion, as Sir Michael began to increase his fucking rhythm. Her cries, “AAAAAhhhh, NO MORE, SIR!” and breathless gasps seemed to only spur the smiling Sir Michael on to fuck her faster and harder. He grasped her hips and began to sodomize her in a fast paced rhythm, as she squealed for him to stop. “OOOHHHhhh SIR, PLEASE!” His only reply was to say, “MY dear Jamie, you will learn to love this union between us, once you get used to it with much more practice and exercise! Now Hush and accept my love!” After about ten minutes of sodomizing Jamie, she quieted down and accepted her plight. Only passionate gasps escaped her lips now, as he drove in and out of her gripping tight bottomhole. Finally, he slowed down and slipped his raging cock from my sister’s pink anal opening. He must have decide that it was my time to be sodomized. Still slick with the oils from my sister’s bottom, he walked behind me and slowly inserted his raging hard-on straight up my bottomhole. I gasped and moaned just like Jamie had as he filled my bottom with all 8” of his big hard cock. My sphincter burned as I wasn’t well prepared and I had to keep telling myself that I was doing this for my sister’s welfare. Dr. Brown had been playing with his cock while Sir Michael was sodomizing Jamie, and now he stepped forward to fill her bottomhole, too. She moaned and squealed again as he slipped his hefty manhood into her defenseless little bottomhole. He grabbed her hips and slowly began to stroke in and out of her stretched anal ring. Both men were panting in lust and commented on how tight we both were back there. It was obvious that they were enjoying themselves however, as we suffered the pillaging of our anal openings for their pleasure. Finally I heard Sir Michael groan loudly as he sodomized me hard and fast, and I soon felt his hot spunk shooting deep into my anal cavern. Within seconds, Dr. Brown groaned out his ecstasy of discharge too, as he shot his seed deep into my little sister’s plundered anus.

 

Dr. Brown lay over Jamie and Sir Michael lay on top of me, squeezing my nipples and fondling my breasts as his spend cock shriveled inside of my ass. Both men had cumm hard, and our assholes were sore from the friction of their plunging huge cocks. After a few minutes of fondling us and pinching our exposed nipples while we squealed and twisted beneath them, they both pulled out and smacked us on our bottoms. “Congratulations girls, you both have learned how to milk and pleasure a man with your tight little bottoms. It is a lesson that will serve both of you well and will be requested of both of you often. Now turn around and cleanse our cocks of all of your juices.”

 

Jamie and I slowly got off the arms of the loveseat and knelt before our Masters. I opened my mouth and began to suck on Sir Michael’s cock to cleanse his semi-limp manhood of my essence. My sister humbly did the same for Dr. Brown. I know they really liked our efforts, as they moaned and quivered while we gently bathed them with our tongues. After we had finished, they dismissed us to our rooms to clean up and to get ready for dinner. They handed each of us another package and told us to wear our new outfits for dinner, as we would be helping Collette serve.

 

Jamie and I thanked both men, and slowly wiggled our way upstairs to our room. After being sodomized like we were, our bottomholes were not only sore and pink from the friction, but were dripping our Master’s spunk as we walked.

 

Chapter 11 – Household Maids

 

As we got to my room, I invited Jamie in and asked her to bend over the bed. I spread her cheeks to look at her red puckered anal rose. It was swollen and bright red from being sodomized due to her first anal awakening lesson by both men. I took some lotion and gently massaged it into her puckered rose. It was soothing and cool and she greatly appreciated my efforts. After I had finished, she returned the favor for me, and anointed my anus with some lotion too. After washing up and slipping on new lace panties, we both opened our packages to find skimpy little maids outfits that we were supposed to wear to dinner. I looked at Jamie and then at the clock, and it was almost 5 PM. With our bottoms still a little sore, we quickly made our way down the stairs to the dining room to do our next duty. We helped Collette serve dinner and with our skimpy little outfits, both men couldn’t keep their hands off our bottoms. Later, they invited us to sit down next to them and eat, after they had finished. Sir Michael discussed our future tasks in his household as his “Cherry Slave Girls.” I was assigned to maintain and clean certain areas of the household, and Jamie was assigned to other areas. We were then given lists of things to do starting tomorrow. We were told that if we failed to complete our tasks by 3 PM each day, we would receive a spanking. Finally we were told that I would spend every even numbered evening with Sir Michael as his guest, and Jamie would spend the odd numbered evenings. If Dr. Brown stayed over, both of our services would be required. After all the arrangements had been stated for us, Dr. Brown left, and we were dismissed to our rooms but not before Jamie was reminded to report to Sir Michael’s bedroom chamber promptly at 9 PM.

 

A little before 9PM, I heard Jamie’s door open and listened as she walked down the hall to Sir Michael’s bedroom. That evening as I lay in my bed, I wondered what he would require my sister to do for him. The next morning after breakfast, as we were starting our tasks, I asked Jamie what he required of her.

 

She smiled and said, “OOOhhh Julie, he did things to me that I never knew could happen before. HE first checked and fondled my anus while he made me suck on his cock. Then he tickled my clit until I gushed furiously for him. Then he restrained my arms and ankles with soft leather restraints and dabbed some hot stinging stuff into my asshole. While my ass burned with fire, he made me cumm over and over again for him until I was exhausted.

Then in the morning, he made me suck him until he squirted into my mouth and made me swallow his passion. He must have been pleased with me because after I had sucked and swallowed him, he went between my legs and sucked my hairless pussy and clit until I exploded for him. It was demanding and wonderful, Julie, and I enjoyed every minute. I enjoyed my Master last night, as much as he enjoyed me.”

 

I started to feel a little jealous of her, as he hadn’t done all those things to me when I was with him. Then I came back to consciousness and told her that we had better get working, or we would be spanked for not completing our tasks.

 

True to my prophecy, when 3 PM came around, neither of us had our tasks completed. We both received 20 hard hand spanks and a thorough frigging from Sir Michael and were then sent to our rooms to get ready for dinner. He told us to wear a nice dress to dinner, as we would be entertaining guests this evening. We wondered who it could be that we would be entertaining tonight. A little before 5 PM, we both got dressed in one of our nice dresses and then made our way down the stairs to the dining room.

 

 

Chapter 12 – Dinner With Sir Michael’s Friends

 

As we entered the dining room, I noticed Dr. Brown on one side and a man and a woman sitting next to Sir Michael. I had never seen either of them before, but they looked very influential. We graciously walked over to Sir Michael and greeted him with a kiss and he said, “Jamie and Julie, this is Mr. And Mrs. Cromwell, and they are going to be joining us for dinner this evening. Please be seated across from them, as Collette and Carlton will be serving this evening.” Sir Michael was at the head of the table, the Cromwells were on one side and we were on the other, with Dr. Brown next to us. No sooner had we sat down and Sir Michael started telling our guests about the unfortunate accident which happened to our Papa and how he was now our legal guardian and we were his wards. They both smiled, obviously knowing Sir Michael’s taste for lovely young girls. Then Mr. Cromwell looked at me and asked, “So Julie, tell me, has Sir Michael broken you girls in yet?” His wife Mary giggled, and we both blushed as she said, “Harry, you’re so blunt and forward!”

 

Still crimson faced and not knowing what to say, Sir Michael quickly blurted out, “Harry, both girls are still virgins and will remain that way, if that is what you are asking.” Both Jamie and I smiled politely as Sir Michael came to our rescue and answered the question for us. Harry winked at us and said, “OK, but I’ll bet he’s given both of you girls a thorough exam, checked your bottoms out, and made you cumm for him many times though, hasn’t he?”

 

At this question, we both flushed crimson red again, and I wondered how he knew the answer to his question, before we could speak up. Then I softly say, “Yes Sir! Sir Michael is seeing to our well being, education, and training with Dr. Brown’s accompaniment.” Harry and his wife both smiled at Sir Michael, and said, “After dinner, we would love to have you give us a demonstration of your training lessons to show us how you chastise these two beautiful young girls with a spanking and then make them cumm for us.”

 

I was shocked and appalled that someone would think of us as entertainment for their pleasure. Suddenly, my thoughts were cut short by Sir Michael, who replied, “I’m certain that something can be arranged after dinner, Harry!” He smiled and nodded, as our appetizers and salads were brought to us to eat. Suddenly I wasn’t very hungry any more, as I couldn’t eat very much of either my salad or of the appetizers. Jamie wasn’t as bothered by the offer as I was, or maybe she didn’t realize that our bottoms were going to be spanked and plundered after we ate dinner.

 

Our dinner guest thoroughly enjoyed the feast that Sir Michael had served them. Carlton was quite a good cook, and Collette did all of the serving. After everyone had finished, the table was cleared and Jamie and I were told to bend over the table. Sir Michael moved that lever under the table, and it opened the table up, producing the two sets of wrist-sized stocks that we had seen on a previous occasion. Dr. Brown opened them up, and placed our wrists inside of them as we stretched across the table. Then the bar was lowered across our wrists, and we were bent, stretched and restrained, all at one time. Next, our dresses were lifted, and our drawers pulled down and discarded by Sir Michael. We both blushed shamefully as our pussies and pink swollen bottomholes were prominently displayed to Harry and Mary. Both of them laughed as they saw how swollen and red our recently used anal passages were. Harry chuckled and commented, “Sir Michael, you always did like to give a tight little teenage ass a good buggering, didn’t you!” Next, Sir Michael had Carlton bring some kind of spreading bar with cuffs, which he used to spread both of our legs wide open.

 

After having fur lined cuffs fastened around my ankles and having my legs spread, I felt fingers tickling my swollen anus and then move to my pussy and clit. They quickly squeezed my clit and made me jerk and quiver as I was totally on display for the pleasure of his invited guests. Jamie was jerking and squealing too, as Mary frigged her little love button real hard. Suddenly the hands were gone, and then a sudden strong THWACKKK. I jumped as Sir Michael sent his crop into my right bottom cheek. He explained to Harry how he had made an offer to us in exchange for our servitude to him. He explained his little maid idea and said, “I give them tasks to do for each day, but they don’t seem to finish. That’s why their bottoms are still pink from their spankings this afternoon.”

 

For the first time I thought I understood the workings of the male mind. He actually enjoyed making us squeal and cry for him while spanking us. He purposely gave us tasks that we couldn’t finish so that he could spank us with some justifiable reason. He also greatly enjoyed making us cumm for him, because after he and Harry had spanked our round red bottoms, Sir Michael and Harry frigged us again until our pussies gushed with excitement. He told us that it was good for a young girl to cumm regularly, and he was going to see to it that we did. Neither Jamie nor I minded cumming for him though, as we were getting used to it and enjoyed having our clits tickled.

 

After our little show for his guests, Sir Michael dismissed me to retire to my room, but told Jamie that she was to wash up quickly and be waiting on his bed in her white silk nightgown with the slit in the rear. Everyone knew that she was going to have her tight little rosebud lubed and stretched again, and before she went to sleep she would have Sir Michael’s sperm swimming in her bottomhole.

 

In the morning, Jamie was required to milk Sir Michael’s cock again with her mouth. She swallowed and thanked him afterwards and told me that she too was beginning to enjoy her newly found life of intense sexuality with our Guardian and Master.

 

Our lives continued as Sir Michael’s little maids and daily we received our afternoon spankings and got frigged. Occasionally he would take us into town to go shopping for personal items, or lingerie or a dress. After a few weeks of being his personal maids and assistants, he also taught us some simple business skills and showed us how to balance his record books for the textile plant. It was like he was our Master, our Guardian, and our Tutor. He loved it when we sat on his lap so he could play with us as he was instructing us. Jamie and I took turns cuddling up to him. On my night with him, I got to sit on his lap, and likewise it was for Jamie. It seemed to raise his manhood and make him very passionate toward whomever he was going to sodomize for the evening.

 

Dr. Brown would occasionally stop around during our spanking and frigging time to examine each of us, and then stay for dinner. He usually made one of us suck him off after our spanking and frigging. Occasionally Sir Michael would ask the good doctor to stay the night, and take his choice of us. He had a special liking for Jamie, and usually picked her to do the honors for him.

 

Chapter 13 – Summer Party

 

Near the end of the summer, Sir Michael threw a huge summer bash for about forty of his friends and business acquaintances. Jamie and I, along with Collette and Carlton served and waited on everyone. Sir Michael announced to his friends that we were there to serve the needs of everyone, but that we were virgins and he intended for us to stay that way. His announcement only encouraged fingers and hands to continually poke and grope our bodies as we walked around. As the day wore on, the guests got a more inebriated and things got a little wilder. I saw one older gentleman grab Jamie by her underwear tearing them off, and then begin to frig her as she tried to pour some wine for him. She just stood there and accepted her fate. With a weak smile on her face, soon she trembled and orgasmed for him. She thanked him and then continued on with her work minus her panties. Soon I too had my panties torn off and was getting frigged by a handsome and horny young man who was some cousin or something to Sir Michael. His fingers threaded back and forth between pinching and frigging my clit and finger fucking my asshole. As soon as I came for him, he jumped up and bent me over his chair. His fingers probed my bottom deeply and when I protested, he spanked my bare ass, ten times hard. Then he had me kneel in front of him and suck his essence from him until I had milked him dry. He held my hair and forced me to take his cock deep into my throat as he squirted his essence for me to gulp and swallow. By the time the party was over, our clits ached and throbbed as we had cumm countless times. Our assholes had been plundered repeatedly and were very sore and cherry red. We had sucked cocks and pussies and were covered in cumm stains. We were totally exhausted, as we literally had to do whatever was asked of us or we would be punished or spanked right then and there. I’d never seen Collette get fucked or sodomized before this night, but she too was used and abused in all of her holes before the night was done.

 

Finally, all the guests left about midnight, and we were told to clean everything up before we went to bed. Sir Michael gave both Jamie and me the night off from our bedside duties with him as we had to help Collette clean up the mess. Collette told us that a pretty little thirteen year old auburn haired teenage girl named Alexandria, who was the daughter of one of his tenants, had accompanied him to his bedchamber. Collette told us that her folks were way behind on their rent, and that little Lexi was given to him as half of the debt payment. We both knew that she would undoubtedly become another one of Sir Michael’s little sex slaves to satisfy the insatiable appetite of our Master’s big cock. Before we both went to sleep, we could hear little Lexi squealing and protesting before getting a spanking in Sir Michael’s room. After a while her crying and whimpering stopped as I’m sure he gave her a powerful lecture about what he expected of her and what her duties with him were to be. She undoubtedly got a thorough examination that evening, after being shaved smooth, and then got frigged. We could all hear her little teeny girl voice squeal loudly, as she climaxed for him before they went to sleep. She certainly was in for a new change of lifestyle with Sir Michael.

 

Chapter 14 – Lexi’s New Family

 

Sir Michael allowed Jamie and me to sleep in until 7 AM, before Collette brought us breakfast in bed. I thanked her for her efforts and then she handed me my list of duties for the day. After I had showered and got dressed, I ran over to Jamie’s room to talk to her. She asked me if I’d heard little Lexi squealing and crying in Sir Michael’s room last night. I told her that I had heard her and had listened at my door for a while until she stopped crying. “I’ll bet he spanked her good for not obeying him!” Jamie giggled. “But she’ll learn to obey The Master, just as we have. I think he made her cumm for him, too, as she squealed loudly just before we went to sleep.”

 

After breakfast, Jamie and I started doing our chores. As we swept and cleaned the upstairs, little Lexi and Sir Michael finally emerged from his bedroom about 9:30 AM. He had his bathrobe wrapped around him and she wore only a t-shirt and her panties, and blushed as she walked past us. Her mouth glistened with the wetness of the Masters cumm, and we surmised that he had recruited another cute little cocksucker into his household. She showered in the bathroom next to our rooms, while Sir Michael went downstairs for some breakfast. After she had finished, I greeted her and said, “You’ll be fine, Sweetie. Sir Michael is really a very nice man once you get to know him and obey him.” She faked a smile and asked us if we had been forced into his bed, too. Jamie and I both giggled and I said, “Yes Lexi, and we squealed while he examined us, and then got spanked just like you did last night!” She blushed again and asked, “You heard me? Did he shave you and play with your ………, AAhh, you know, down there?” she asked, pointing to her pussy. “Yes, Lexi, and he made both of us cumm for him, too, just like you did last night.” She blushed in amazement that we too knew the pleasure from Sir Michael’s skilled fingers. “He also made us both suck his big manhood, as I’m sure you had to do for him this morning.” She opened her mouth and with a gasp, said, “OOOhh, I know. He is SOOO big, and I nearly choked on his salty fluids, which he made me swallow when he came in my mouth.”

 

We all giggled and then I said to her, “Welcome to our family, Little Lexi. Jamie and I both know what it is like to swallow his massive load of juice. But Lexi, you do get used to his beautiful cumm spitting “love muscle” as you practice your lessons with him day after day. “Love muscle, Julie? What do you mean?”

 

I smiled at little Lexi and stroked her soft cheek, saying, “You’ll find out soon enough what else he uses his manhood for, Sweetie. Just be sure you obey him, or your little ass will glow red hot from his punishment.  You also should know that since Sir Michael is now your new legal guardian, as he is ours, that we are all like sisters together here. Or should I say, that we are all more like Sir Michael’s “Cherry Slave Girls.”