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The Making of a Sissy

Part 4

Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bellas phone, Ellen tapped in the number to her own phone, and also took down someone elses number. Ellen smiled wickedly.

“I have a very sweet idea, but Ill need a week to arrange it; I have to put a proposal to that aunt of hers first.  Ill need your assistance at some point.” Sandy was willing to help out in any way, and the two chatted and giggled as they too went back upstairs to shower and prepare for the evening.  Roberts worked swiftly to get the videos and pictures on to computer, whilst Carl ogled at the results on screen.  Roberts also uploaded several select images to a covert site he was a member to.  Within minutes there were rave comments about the beautiful sissy who was performing with the well- known and well received Ellen; Roberts was very smug, but knew he would have to afford Bella a great deal more respect now, especially as she had hit it off so well with the mature redhead; he could ill afford to lose her friendship in the business.  Roberts printed off many pictures and handed them to Carl to slide into an album, whilst he burned a few videos to disc.  They too then prepared for a relaxing evening with the girls.

As darkness fell the night air retained its sticky humidity and the party sat down, comfortably attired and all members very relaxed and happy with the days events.  Bella sat between Ellen and sandy who both petted her admiringly as they sipped at the alcohol.  Bella had never felt so relaxed or fulfilled in all her life and her eyes glistened softly as they wandered around the illuminated pool and grounds; the soft scent of the other girls and the warm chatter of the two males adding to the atmosphere and her contentment.  Ellen gave her a soft cuddle.

“Tell me about your Adam; what is he doing at the moment?”  Bella blushed a little despite her relaxed mood.

“Oh hes working his way through the later stages of college at the moment; hes not too sure what he wants to do permanently but he does a lot of bar work at the moment.  Hes always saying how hed like to mix a few cocktails for me.” She sighed wistfully.

“Id love to take him up on that, but I can never be out without my sisters, and Aunt Jane wont here of us hanging out in bars.” Ellen took a long sip of her drink as she listened, then smiled at Bella.

“You never know, things can change rapidly; youre a very pretty girl and your aunt cant hold onto you forever.”  Ellen and Sandy smiled at each other as though maybe they just knew something the sissy didnt, but Bella soon forgot about it as her phone buzzed.  She exchanged a few sweet nothings to her sweetheart and the others were touched at the soft sincere way she gripped the arm of her chair and spoke to the young man as though he were the last person on earth. As she blushingly whispered I love you down the phone, Sandy asked if she could speak to Adam too; Bella was only too happy to oblige the friend who had given her the freedom of that phone.  Sandy spoke to Adam about a website, and whispered to Roberts who gave her a password which she passed on to Adam.  Sandy giggled as she ended the call and passed the phone back to the sissy.

“Oh Adam is going to be so excited when he sees his little sissy next time; you wont stand a chance!”

The friends drank long into the warm night, at one point watching various recordings of the earlier work on a huge screen by the pool; Bella gasped as she saw herself, perhaps realising for the first time just how beautiful she was. The more they saw, the more pleased both Roberts and Ellen were with Bella.  In the early hours, after many conversations and many more drinks, they all went to bed; Bella cuddling up to her soft pillow, thinking of her experience earlier, and yearning for Adam.

Adam finished his bar job, went home and hurriedly entered his room, fire dup his computer and entered Sandys directions.  A broad smile erupted across his face as he saw Bella with the delicious redhead; the swell of his cock as instantaneous as his grin, which now turned to gasp of sheer wonder and excitement at the beauty of the sissy he cherished; he picked up the phone.

Bella was lying face down in her soft warm haven, her sissy cock rigid as she thought of the bonds of earlier, and her Adam.  As if by magic, the buzz of the phone brought her back to reality, and she picked it from the table.  A warm deep voice made her little cock stiffen all the more.

“Im just looking at some pictures of you; I so want to be with you now. You look so vulnerable; I just wish I could have been there to comfort you afterwards; were you scared?” The sissy giggled softly as she rubbed herself at his welcome voice.

“Only a little, I was thinking of you all the time and that helped me relax and enjoy what was happening to me; please dont be ashamed of me; thats what scares me most.”  Adam stroked his erect cock as his listened to his sweet sissy and looked at the beautifully erotic pictures.

“Oh! You gorgeous thing! Im just jealous that I wasnt there; Im going to come in your honour right now, to make up for it; I want you so much.” Bella listened intently as Adam softly moaned with pleasure; she would help him.

“Are there any pictures of the dildo there?” Adam moaned louder as he neared orgasm, and clicked further into the series of pictures.

“Ahh! Yes, if only Id been there, I need your sweet little pussy so much.”  Bella completed her sweet tease with what was the honest truth.

“I imagined it was you, my Adam, inside me for the first time; I came so sweetly Adam, I will save myself just for you!” Bella closed her eyes and sighed as she heard Adam virtually roar down the phone as he experienced the most luxurious orgasm hed had since Bella obliged him in the sea.

“Bellaaaa!!!  I want you so much.” His cock spurted generous loops of cream as he viewed his sweet sissys pussy being violated by a woman whose face he did not see; Roberts had been careful to give out coordinates for a freebie section of the site which did not show Ellens identity.  Adam was not concerned with this, he had eyes for his sissy only, and he spent gratefully again and again.  The two whispered their sweet nothings and Bella cuddled her pillows and slept soundly after the call; she had pleased her love, which gave her more pleasure than anything.  She could not know that the next weekend was to be even more exciting than this one.


Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Janes.  She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was.  Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.

“Well, youve certainly impressed Mr Roberts, and its nice to see you with your clothes on again.  We are quite the little harlot now arent we?  Well soon have you back down to earth; Ive lots of chores for you!”  Now it was sandy who was downhearted as she drove away from the house and saw poor Bella disappear meekly indoors.

By Friday, Bellas strict and humdrum regime made her doubt that the last weekend had really happened, and the next one seemed so far away; besides, she had spoken with sandy several times but she had not mentioned the following weekend at all.  Tears welled in the sissys eyes as she began to despair; Adam was very sweet on the phone, but his voice only made her yearn for him all the more.  She watched her step-sisters come and go as they pleased; they were now avoiding taking her anywhere as they knew she must have had a good time at the weekend and wanted to punish her.  They smiled as they headed out to the beach; Tara was particularly nasty and teasing.

“If I see Adam Ill tell him youre busy entertaining some old man; then maybe Ill take him into the dunes and have him entertain me. Dont forget to wash my dirty panties; youre free to give them a good sniff if you like.”  Bella was now really despondent; she knew Adam wasnt interested in Tara, or anything she said to him about her, but the thought that he might be down at the beach while she were here was too much to bear.  Tears ran down her cheeks as she emptied the wash baskets and bagged the dirty objects to take down to the washing machine.  As she descended the stairs she noticed a car in the drive and heard her aunt talking with someone in the front room, but didnt give it another thought; Jane often had visitors.  She loaded the washing machine and began the tedious vacuuming as usual.  After about 15 minutes something caught her eye through the window, and she saw a smartly dressed woman, red hair in a bun, put the keys in to the car door. As the woman did so, she turned to look face on at Bella who gazed through the window. Bellas jaw dropped as a very business-like Ellen smiled back at her.  Bella froze as the front room door opened suddenly and Aunt Jane made a command.

“In here now sissy, I have some news for you.”  Bellas mind was pulled in a thousand different directions and the butterflies in her stomach were more violent than usual as she wondered what was to be said.  She stood before her Aunt Jane.

“Pack your things; I am to be rid of you at last it seems.  I had my mind set on passing you on to some lecherous male, but I see you might enjoy that now.  Fortune has smiled on us both.  Now that your schooling has finished, you are to train as a maid. That Lady who was just here, lives in a large house and is a friend of Mr Roberts.  She likes to be strict with her charges and trains girls and sissies to be French maids; apparently she saw you when you were at Mr Roberts and thought what an obedient maid youd make; she will pay me weekly for your services and will work you hard.  You will benefit from your training as this will earn you your keep at her house. She will no doubt hire you out to some of her gentleman friends like Mr Roberts; no doubt you may receive small tips from them if you perform well.  Pack your bags; you are to go within the hour, she is to return for you.” Bella tried to look scared at the proposition.

“But…I …” Aunt Jane looked sternly at her.

“Upstairs now this instant and pack your things.  I shall cane you if you make one more sound.” Bella walked from the room and tried to walk as slowly up the stairs as possible; it was all she could do to stop herself from screaming deliriously with happiness as she quickly packed her meagre sets of clothes and belongings into a large carpet bag she used when at boarding school.  The minutes ticked by and Bella was so anxious. Then her phone buzzed; she answered softly hello; Adam? Sandy? A voice she recognised from the weekend laughed into the phone.

“I hope youre ready sissy; Im coming to get you!” That was all that was said; moments later, the bell rang and Ellen was at the door.  Bella was ordered downstairs and Aunt Jane looked very pleased with herself as the strict and governess-like redhead wrote an advance cheque for her. Jane smiled.

“You be sure to cane her for slightest misdemeanour; the sissy knows her place amongst women but performs so much better if disciplined regularly.”  The redhead looked down at the submissive sissy.

“Oh you can guarantee she will be kept on a tight leash at all times, and will feel the warmth of my hand if she is disobedient.”  Bella kept a downbeat face as her little cock swelled with sheer excitement.  She could not believe what was happening.  Before she knew it she was sat in the front seat of Ellens car.  Ellen exchanged a few niceties with Jane and confirmed how payment would be made before entering the car herself.  Jane watched intently with a satisfied smile as she saw the sissy sitting bolt upright, looking fixedly ahead with tears streaming down her cheeks.  As the car drew away she could see the redhead speak to the sissy with a stern look; she thought of how maybe a caning was promised. Ellen had such a haughty look as her stern jawline mouthed at the sissy.

“Just wait till we get round the corner, out of sight of that dragon; I cannot believe how easily paid off she was! I am going to give you such a cuddle!” True to her word, Ellen pulled the car up by the side of the road and gave the sissy such a hug it took her breath away; the tears of joy flooded from Bella as Ellen told her how she was going to live with her now.  She would be taught to be a French Maid, but only because Ellen wanted her to be seen like that to her house visitors; she was going to get paid more than the salary she had paid Jane too, and though she would want help with the housework, Bella would be allowed to do just as she pleased.

Bella could not wait to phone Adam to tell him, and looked at Ellen wide-eyed as she asked if she could see him. Adam was thrilled, but had to do bar work Friday till the early hours and had to attend a private function on Saturday from mid-day onwards; he had been approached by  a couple at the bar he worked in, they were impressed with his cocktail mixing and had made him an offer he could not refuse. He was desperate to see her and would have put the couple off if he could give more notice, but he could not do it on the Friday. He would call her Sunday first thing.  Bella had a bittersweet look on her face; she wanted Adam right now, she was so happy.  Ellen gave her the most curious of smiles when the sissy finished her call.

“You poor thing; if only we could get you to see him sooner! Never mind I expect the time will flash by and youll be with him before you know it. I have a few friends visiting my house on Saturday and I would love to introduce you to them, so you wont be lonely.”  Bella leaned her head against Ellen as they drove across town; she was safe and secure at last. Ellen lived in a house that was as impressive as Roberts; a huge detached place in an Italianate style.  Bella gasped as she looked at the magnificent residence. Ellen smiled.

“You see, you can be very successful as a t-girl; you just need a little confidence and to stay pretty. I intend to help you that way.   I cant wait to see you dressed as a French maid; despite our little joke with Aunt Jane, I think youd look so sweet.”  Ellen showed Bella her room, all done out neatly in pink with a huge double bed.  She took her bag from her and helped her unpack.

“Not a great deal here; well go clothes shopping tomorrow; then well kit you out as a maid and you can help me with the preparations for the party, but tonight, I think you deserve a drink.” Ellen took her hand and led her downstairs, through a huge kitchen and then through huge patio doors to a pool half as big again as Mr Roberts.  Sat in a chair next to it was Sandy; she greeted her with a broad grin. Bella ran and embraced her.

“Oh you cow! You knew all along, and I was so miserable.” Sandy kissed her.

“Of course I did, but I bet youre glad now I didnt let on! Oh, and we are all going to have such a great time with everyone tomorrow!”  The three sat together relaxing all evening, Bella couldnt help but notice how the other two seemed so thrilled about the event tomorrow; they just told Bella that her situation had lifted them, and that was why. The two took Bella to her new bedroom when the time came, tucking her in like a child and admiring what a nice job had been done in preparing the room for her.  They kissed her and she soon drifted off to sleep; thinking of a certain bar tender, hard at work.

The next day, Ellen took her shopping and they visited many boutiques; Bella shyly accepting the outfits purchased for her. Finally they went to a specialist where Bella tried several French maids outfits; the one they chose hugged her slim waistline, showed the length of her legs and accentuated her sweet breasts perfectly; Bellas cock stiffened instantly as she viewed herself in the mirror. Of all the pretty and sexy things shed been bought, she could not wait to wear this and serve in her submissive way. Ellen knew it would be this way and rubbed the sissys little bottom.

“You are going to have such a day later! You just remember to wear your panties over the top of your stocking garter belt; that way you can take them off and have a real tease.” Bellas little cock stiffened as she felt the silky material and the lacy frills; though Ellens talk with Aunt Jane earlier had been a sham, she relished the erotic thought of being enslaved in such a way; helping out whilst dressed like this would make her so horny!  Reluctantly, Bella took the outfit off and the two went home.

Across town Adam carter was wishing it were tomorrow; on the one hand he could not believe he would be able to see his sweetheart whenever he wanted, but on the other he was so frustrated- it was so bittersweet- he wanted her now!  He tried to keep his mind on driving to the destination; his cock permanently semi erect as he thought of caressing sweet Bella.  He arrived at the house and was directed to an area where a bar and disco were being set up; he was to be allowed to set up the various bottles to make ready for cocktail preparation.  The man who took him to the bar area introduced him to no less than three other barmen, who smiled at him in a friendly manner; they all seemed to know each other and were overly keen to ensure Adam did not have too much to do.  He looked at the man who had introduced them.

“Think were going to be a little overstaffed arent we? Not that Im complaining!”  The man fiddled with one of many cameras he was holding as he replied.

“Oh dont you worry about that, we just like immediate service, and there will be good reason for a few drinks tonight, believe me.”  Adam looked at the bottle collection and noted there was no Vodka. The man told him it was in a room upstairs.  He passed Adam to the hostess who gave him a very warm smile and asked him to follow her. Adams cock swelled as he watched the shapely arse ascend the stairs; he put down his more horny than usual attitude to the fact that he would see his Bella tomorrow, but something made him urgently want to spend that very day! He tried not to look at the mature womans bottom; she had red hair too, he always liked that.  The woman stood by the door and whispered.

“Just ask the maid for the vodka. Oh, you neednt hurry back.”  Adam was now totally bemused by the situation. She opened the door to a bright pink room.  Adams cock would not behave itself as he looked at the rear of a pair of beautiful legs in a French Maids outfit; they looked strangely familiar; the maid turned from what she was doing on hearing the door.

Adam and Bella stood looking at each other, frozen in a strange disbelief at the apparent apparitions they were both encountering.  A warm smile broke out over Adams face; Tears ran down Bellas face.  Adam found the strength to walk over to her, though his legs seemed to turn to jelly.  He stared into her soft blue eyes.

“Bella, Bella…” was all he could manage to say. He squeezed the sissy as though to never let her go, and they kissed long and hard, dribbling with excitement.  Bella forgot her tears and her ladylike demeanour as she quickly removed her panties, releasing her stiff little sissy cock.  Adam rubbed her tight little scrotum and then wrestled out of his clothes.  He kissed her sweet neck as he helped her out of the maids uniform, and she stood there naked but for her black stockings.  The two stood caressing for a good three minutes, just with the pure wonderment of being alone together at last; Adam holding the beautiful sissys sweet bottom tightly, Bellas little cock rubbing sweetly against her lovers; their bellies tight against each other in a loving and sensual embrace.  Bella broke first and took her mans hand; he would not leave without taking her virginity with him.  She led him to the bed and pulled him onto the soft inviting duvet. She wrapped her legs about him and whimpered as he licked her soft feminine breasts and gently probed her willing anus with a finger.

“Oh Adam, now, please now!”  The sissy un-wrapped her legs and gently turned, to face the bed and on her knees, raising her delicious soft white bottom submissively.  Adams cock was rock hard as he viewed the sweet angel he so desired, there just for him after all these years of waiting; he put his hand gently under her belly and pulled himself forward over the top of his darling Bella.  He nibbled the back of her neck as his hard cock rubbed at the top of the sweet cleft of her buttocks. He gently moved down a little, the warmth of her inviting pussy exciting his tightly expanded bell-end as he firmly probed, making his sissy whimper softly.  She was his now and he wanted to have her so urgently, yet wanted to make it last forever.  Adam softly grasped Bellas little cock which yearned to come as did his; at the ecstatic moment of his first tight entry into her sweet hot haven, he squeezed and stroked the sissys cock.  Bella moaned at the pleasurable sensations; she could not have dreamed it would be so deliciously erotic.  Adam moaned too as he slipped his cock into the tight and unbelievably pleasurable grip of his sissys beautiful anus.  Bella gasped at the gorgeous mixture of pain and pleasure; Adam was not huge, but she was a virgin and she knew now that Ellen had only given her a tease to ready her; she was now being well and truly fucked and this was absolute heaven.  Adam stroked right up to the hilt as his sweet sissy surrendered completely; his thighs now slapping her soft cheeks as he drove his cock home again and again.  Bella felt him master her and moaned in submissive indulgence as he fondled her cock also, albeit erratically as he was in a state of near ecstasy.  Bella moaned in ecstasy also as her prostate was pulsed again and again along with Adams rough strokes of her little cock.  Her anus gripped his cock all the tighter as she squealed on reaching that delectable zenith; she was his and her little cock squirted magnificently as an incredibly intense orgasm wracked her soft body.  Adam almost roared as he too released his hot seed deep in his beautiful Bellas pussy.  She was no longer a t-girl, she was simply the feminine beauty he loved; he writhed in pure ecstasy as he shot spurt after spurt of his hot gift deep into Bella. 

The two embraced and Bella cried yet again.  Adam simply smiled and kissed her again and again.  She was his and he was hers; there would be nothing to keep them apart now.  The two almost fell asleep and would have been glad to do so, but for the scheming that had brought them together; they must thank those who had made it possible.  Bella sat proudly as Adam buttoned her into her maids outfit once more; his kissed her again and again as he did so, he was so ecstatic himself that she was finally his.  They stood and smiled at each other, then both looked at the inviting pink bed in unison; yes they would both look forward to being wrapped in each-others arms there later.  Adam took his Bellas hand and led her down the stairs.

The two lovers could hear the pulsing music and dim lights as they moved through the kitchen, but this stopped abruptly as the moved out onto the poolside arm in arm; the entire crowd, led By Ellen and Sandy applauded as the two approached; Bella blushed pink, not for the first time in her sweet sissy life.

Review This Story || Author: Midsummerman
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