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Review This Story || Author: Midsummerman

The Making of a Sissy

Part 3

As Sandy pulled into the drive of Aunt Jane s house, Tara turned from the front passenger seat and eyed the forlorn looking sissy seated centrally between her two sisters with some satisfaction.

“Its a good thing your friend can stay with you tonight to console you; of course Id have done the same if she were not staying.”  She and the sisters who sandwiched Bella, all sniggered sarcastically at the sheer comedy of the thought.  Bella maintained a look of hopeless nonchalance as she gazed aimlessly through the window as Sandy applied the handbrake.  The sisters alighted from the vehicle with barely a gesture of thanks to their driver, and strutted round to the front door.  Bella and sandy smiled at each other with relief and followed on after Bella had retrieved the sisters beach gear, as was one of the duties expected of her.   Sandy was treated to a coffee and a chat with Jane, while Bella loaded the washing machine with everyones swimwear; she was allowed to eat with the others and then given permission to disappear to her room with Sandy.

The two embraced and giggled as soon as the door was closed behind them.  Bella then retrieved the phone from its hiding place and set it on the wooden bedside table, so that its buzz would be audible if anyone called.  The two stripped off and squeezed into the shower together; their salty bodies in need of refreshing.  This was a thrill in itself for Bella, as she had not seen another t-girl in the flesh; she had managed to find a few on the sisters computer on the odd occasion she had found herself alone with it for a moment or two, but having a like person near her filled her with a sense of belonging for the first time; she now had living proof she was not unique, and Sandy was full of self-confidence; proud to be just the way she was.  Sandy smiled as she noticed Bella gazing down her cock whilst she shampooed.

“Mines bigger than yours!” She joked, making Bella blush at the realisation that she had been staring rudely.

“Thats ok kid, Ive been looking at you too; you are so pretty, a real catch for that Adam. Youll see my Carl tomorrow; Im going to have to keep him on a leash, his eyes will be all over you.”  Sandy giggled once more as she held the shower head over Bella and washed the lather from her soft white body, but stopped giggling and then stroked her bottom softly, biting her lip as she viewed the still visible evidence of the caning.

“Thats ok.” Bella said softly.

“I actually enjoyed it in the end; I cant help but be submissive, I cant stop thinking about how Adam will be with me; he seems so soft and caring, but I often fantasise about being tied and gagged by him, Im so mixed up.”  Sandy squeezed her as she turned off the shower and patted her down with a soft fluffy towel.

“Youve no need to worry; hes nice and physical, if he could see you now it would bring out the animal in him.  When youve got to know him, just tell him what you like; hes sure to accommodate you. Besides, I promised him copies of some of the more risqué pictures that Roberts takes of you tomorrow.”  Bellas jaw dropped and her face was enveloped in a gaping smile; she snatched the towel from Sandy and held over her crotch to hide her excitement at the thought.  Sandy laughed.

“Hes so obviously in love with you, but theres definitely a horny animal inside him too.  I want you to relax and really let yourself free in front of the camera tomorrow; you just think of giving yourself to Adam and Roberts will be delighted with the results, Im sure.”  As soon as they had dried off, the phone started to buzz and creep across the table.  Bella froze at first; Sandy pushed her toward the table. Bella shivered as she sat on the soft bed and looked bewildered as she said hello? Sandy smiled as Bellas face softened immediately she heard the one voice she really longed to hear.  Sandy sat at the dressing table and tended her hair to allow Bella as much privacy as she could, taking a peep in the mirror now and again, to view the starry-eyed contentment of Bella as she cooed sweet nothings to Adam.  When they eventually ended the call, Sandy came over and dabbed the tears of joy from the sweet sissys cheeks. She looked up at Sandy.

“Oh how Im looking forward to some more vodka tomorrow! Im so happy!”  Sandy sat by her and cuddled her.  They packed Bellas favourite, raunchier things, ready for the weekend then slipped into bed together, giggling like ten year olds as they talked about the weekend; within 20 minutes they were both sound asleep.

Across town in his large residence, Roberts prepared his equipment under the poolside lights in the warm evening air.  He checked his photographic gear and props; his cock rising as he sorted the silky cords, gags and handcuffs, thinking of which would suit best that pretty sissy. He was just as excited as the girls, as he imagined that sweet little bottom, raised in the air submissively.

Bella kept everything crossed as she went downstairs with Sandy on Saturday morning; she could not believe that her Aunt Jane would really let her go, she expected her to smile wickedly at her and tell her it was all just a tease.  Her stomach churned as she attempted to eat some toast; this just to appease her aunt who would not have her go without eating anything; she was very strict with her, and would ensure she did not become anorexic and unattractive to possible suitors.  Bella was in a cold sweat as Jane watched her finish and then turned to Sandy who was happily on her fourth slice with honey.

“I trust you to be my eyes with Mr Roberts; I know you have no influence over him, but he will not risk anything improper while you are around.  Please have Bella back here by 8pm Sunday.”  And with that she strolled out to the garden and sat reading a book.  Bella nearly choked in her efforts to swallow her last corner of toast; Sandy smiled, licked her fingers clean of the honey and rinsed her hands.

“Lets go then kid, what are you waiting for?” The two picked up their bags, Bella almost falling over hers in an effort to get through the door.  They put the bags in the back and got into the car; Bella staring into the rear view mirror, her heart racing as Sandy turned out of the drive with her aunts house disappearing behind them.  As the car drove out onto the open road Bella yelled with sheer excitement. Sandy nearly ran over a cyclist, she was laughing so much.

Bellas little cock stiffened involuntarily and her balls tingled as the car swept up a palm lined avenue and a huge white Art Deco house with green tiled roof loomed up before them.  As they drew up, a smiling Roberts appeared and helped them with their bags; he took them through a plush marbled hallway and up a curving staircase with wrought iron work typical of the early thirties.  Both he and Sandy showed her the room shed stay in; with Sandy of course.

“You two slip into something comfortable then come down to the pool for a drink; I expect youll want a swim later, its going to be a warm one.”  He watched the sissy bend and put her bag down as he closed the door; his cock bulged as he descended the stairs; she was within his grasp now, If only he could find a way.

The two came downstairs. Both wearing saris of a fine sheer material over their naked bodies; they giggled as they sat next to Roberts, who poured them generous drinks.  Bellas nipples were prominent from her sweet round breasts, partly because the morning air was still a little cool, partly because of sheer excitement; this was to be an eventful day in the sissys life…


The girls sat cross legged sipping orange juice as the day warmed up around them. Roberts house had extensive lush lawns beyond the pool which shimmered in the hot sun; the pool looked very inviting to Bella and Roberts looked at the pretty sissy, his mouth watering as his cock pulsed.

“Just go in whenever you want; its nice to see you free from your usual routine, I know how strict your Aunt Jane is with you; swim naked if you wish, no need for a bikini here.  Sandy and the others never bother with swimsuits when theyre here.”  Bella was a little shy at first, but Roberts had seen her virtually naked anyhow, and he was a photographer after all.  Sandy cancelled out any inhibitions she might have had, by taking the initiative and stripping her sari off to reveal her naturally feminine body. Roberts smiled as her cute bottom wiggled to the edge of the pool; he snapped away with one of his many cameras as the slender form dived into the blue pool.  Bella giggled and blushed sweetly as she too, stood and un-wrapped her sari.  Roberts gulped involuntarily and his cock stiffened immediately as he witnessed the sweet perfection of Bellas naked form for the first time. He almost forgot to take pictures as the soft white body of the completely feminine sissy padded graciously to the edge of the pool.  Roberts wanted her to remain there forever as he snapped away at the deliciously curvaceous and slender body.  Her soft short and downy brown hair contrasting sweetly with her pretty pale complexion and red lips, her slender shoulders and well- formed round breasts; nipples sweetly erect, betraying her excitement. Her perfectly girly arms leading down to that soft bottom which still had a few rosy marks; Roberts cock pulsed as this reminded him of the caning,  his eye wandered down to her beautifully shaped thighs and to the front, her dear little sissy cock, which had spent so sweetly under the cane hed brandished.  The nymph-like Bella completed the vision by tip-toeing as she prepared to dive; the beauty of her feminine legs and sweet bottom accentuated by the posture.  Roberts gasped as he snapped away; his cock now rigid.  God! How he wanted to fuck that sissy!

The girls were splashing and frolicking in the pool; Roberts taking the odd snap and video as they relaxed, when he suddenly turned to greet a stunning redheaded woman of about 45 who had just walked in.  The two girls smiled and said hello to the tight skirted mature beauty, who kissed Roberts fondly on the cheek.  The woman was a picture of elegance in her tall stilettos.  She looked down at the girls.

“I cant wait to get in; I love this pool!”  Roberts smiled knowingly at the two girls; Sandy winked back at him.  As the beauty undressed she faced away from the pool; Bella looked enviously at the mature womans buxom form, she was certainly in her prime; her long elegant legs flicked her skirt to one side, and her beautiful red hair waved and shimmered halfway down her back, which was pure white with the exception of pretty freckles around her shoulders.  Bella gasped as she turned; the woman smiled broadly as she revealed that between her luxuriant thighs a cute hairless cock confirmed she was transgender.  Roberts smiled as he saw the little sissys reaction, and thought of how sweet some of the photo shoots would be with the two beauties together.

“Girls, Id like you to meet Ellen; shes going to help with the shoots later, you should look good together.” Bella clung to the side of the pool staring fixedly at the beautiful mature t-girl who swam toward her; she was everything Bella aspired to be, but to Ellen, Bella was everything she wished she still was petit, youthful and irresistibly attractive; Bella had been led such a tortured and sheltered life, she was still unaware how beautiful she really was, her wicked guardians constantly reminding her of being a freak.  She felt very warm inside with her new friend, and this woman was a revelation.  Bella was glad to be in the water as she now had a full erection; she had noticed the handcuffs etc. which played on her mind and excited her, and now this mature woman was to partner her, she was very excited.  Ellen brushed up against the two, exchanged a kiss with Sandy, whom she already knew, and then turned to Bella who was starry-eyed.  Ellen gently squeezed the pretty sissy and giggled softly as their torsos touched; butterflies flooded Bellas stomach as she felt the redheads cock against her; as erect and excited as hers.

“You are a pretty little thing! I shall enjoy tying and dominating you later, even if it is only role-play; why, youre that sweet I could eat you!”  Bella blushed a little; her words as to what was to happen later did not help quell her erection; her little cock throbbed rigidly and Ellen softly stoked Bellas little scrotum, making her yearn to come. Ellen gave her a soft kiss on the lips as she continued to fondle the sissys balls.

“I cant wait to see you in ecstasy later; youll look amazing in the photos Im sure; you mustnt worry about a thing, were all going to have some great fun this evening.”  She smiled and gave Bellas stiff little cock a squeeze, then guided Bellas free hand to her cock.

“There sweetie; thats to remind you that youre in good company.” She smiled warmly as Bella blushed pink as her little hand clasped a healthy sized cock, which pulsed as Ellen tensed her middle at the pleasurable feeling exuded by the delicate hand.

“You are so special! Ill bet there are lots of boys on your tail; do you have anyone to call your own?” Bella was a little mesmerised by the whole thing but managed to reply.

“Theres one Id like to be, and he wants me too, but this is the first time Ive been allowed anywhere without my sisters or my aunt watching over me; Im so grateful for having Sandy as a friend, I didnt even have my own phone till she gave me one; now I can speak to Adam whenever I want.  I just wish I could see him.”  Ellen was amazed as Bella went on to pour her heart out about her strict upbringing, which contrasted sharply with the circumstances by which she had met Sandy.  She told of her history with Adam from the Mall, to her meeting in the sea yesterday.  Ellen was particularly touched by the young mans restraint when he could have penetrated the delectable sissy as the opportunity was there; she was charmed by his wanting things to be right.  Ellen resolved to assist Bella in any way she could; her aunt could not rule her forever, and she was of adult age now.

“Lets go and have a drink now; Mr Roberts will be anxious to start taking some posed pictures soon, and I cant wait to see you pose.”  Ellen watched the pretty bottom ascend to pool steps, followed her, and took great delight in padding the sissy dry with a fluffy towel; both Bella and Ellen had semi-erections as the two contrasting beauties felt the warmth of each-others excitement, which was much to the delight of Roberts as he snapped away; his own cock rigid as he viewed the pair…


As they sat sipping drinks and discussing what shots would be done indoors or out; Bellas little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things.  Sandy stood up suddenly and ran across the patio when she saw a tall figure emerge from the house into the sunlight; this was her Carl.  Bella looked on enviously as the two squeezed and kissed at length. She could only dream of being that way with Adam, and so yearned for such a moment with him. Sandy tugged Carl over to the others; he waved acknowledgement at Roberts and Ellen whom hed met many times before, and then looked down at Bella.  He whistled as he stared at her admiringly.

“Phew!  Sandy wasnt kidding when she said you were beautiful you are stunning!”  He pulled up a chair and sat cheekily close to the sissy, making her blush pink; Ellen and Roberts laughed as Sandy dragged him off the chair.

“I think someone needs a little something to quell his excitement!”  With that she whisked her sari off and stood naked, wagged a follow me gesture with her finger and disappeared inside, Carl needed no further coaxing and followed her.  Ellen smiled and looked at Bellas soft little face which was full of wonder and excitement at Sandys freedom and the confidence that went with it.

“Id love it for things to be that way with you too; I know weve only just met, but I think we are going to be very good friends. I am going to see if I can assist with a little more freedom for you.”

As noon passed, sandy and Carl re-emerged to join the others in the shade for the first alcoholic drinks of the day, Roberts set up a screen and backdrop on the lawn close to the pool and fidgeted impatiently as Ellen stoked Bellas hair while she sipped a Vodka with cherryade; the bright red staining her lips, making them all the more feminine and desirable.  When shed finished, Ellen smiled warmly at her, took her hand and led her meekly to the screen.  Both stripped naked and Ellen had Bella kneel down on the silky platform.  She put her hand under Bellas chin and had her look up at her; the sissys natural submissiveness seemed to flow as she looked up at the imposing and somewhat dominant redhead.  Roberts snapped away and had two videos rolling constantly; his cock ached for relief; even without props, the contrasting beauty of the two shemales was magnificent.  Bella was truly enjoying this new experience and was willing to do anything for the mature redhead whose natural command ensured she was in complete charge of her.  As Ellen gave her a sneering look for the benefit of the cameras, and produced a collar and leash, Bellas sissy cock rose with excitement.  The redheads cock did likewise and poked close to the sissys nose as the mature woman gently fastened the collar around Bellas sweet little neck.  She looked up at the masterful woman with soft submissive eyes as the leash was applied and pulled tight. Bellas bottom tingled with excitement as she was pulled this way and that as the photogenic shemale struck various poses for the camera.  The redheads erection was now full, as she too relished the experience of being with such a pretty sissy.  She whispered softly to Bella.

“I want you to think of your Adam now, but try not to keep your eyes closed all the time.” Ellen drew the kneeling sissy forward on the leash and poked her erect cock at the cherry-red lips; Bellas little cock stiffened and bobbed with sheer excitement as she looked softly up at the sneering redhead and softly enveloped her bulbous bell-end with her soft little mouth.  It took all Ellens willpower to avoid coming in the sissys mouth whilst Roberts snapped away.  Sandy sat naked on Carls lap; impaled smartly on his erection, Carl returning the favour by sweetly stoking Sandys cock as she squirmed and whimpered whilst watching the show.  After about half an hour, wherein various props were used, they broke for drinks once more.  Ellen was so pleased with her understudy, and so was Roberts. Ellen cuddled Bella warmly.

“Well done! You are such a natural! I cant wait to do the bedroom scenes later; we are going to tease you until we are good and ready, then you shall have some relief.” She squeezed Bellas soft little bottom then continued.

“And I am looking forward to some relief too.” Bella was thoroughly enjoying her work and loved the idea of seeing her again after the weekend; she hoped they could remain friends somehow.  Sandy and Carl quickly made themselves decent as the group settled down for drinks.  Bellas phone buzzed and she grabbed the phone, wandering across the lawn and giggling girlishly as she spoke with the one person she really desired.  Ellen smiled and looked to Sandy.

“I want to have that young mans number; Im also going to pay her Aunt Jane a visit too.” She glanced over at Roberts who was busy taking props and cameras inside.

“We need to keep our eyes on the wolves that are homing in on her too.”  Carl laughed;

“You two keep your eyes on him and Ill look after Bella.”  His remark was greeted by a generous helping of iced water down the back of his neck, courtesy of Sandy.  Bella strolled back kissing the phone; her starry-eyed look having returned.  Ellen looked at her warmly.

“Lets go and do the bedroom scenes while you are in the perfect mood; you keep someone close in mind, and you wont disappoint Mr Roberts when we perform.” The party moved indoors and up the stairs…


Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helpless. Her cock stiffened sweetly at the thought; perhaps she would taste the cane again, she would love that. Ellen took Bellas little hand and squeezed it tightly; though she had only just met this supreme example of a shemale, she knew instinctively she could trust her completely.  The redhead smiled knowingly at Bella; her cock was in a similar state of excitement, she could not wait to see her new charge trussed and helpless, and hear her whimper sweetly when she was finally milked.  She squeezed her soft little bottom as they reached the top of the stairs.

“You and I are going to have a few drinks together when were done; Im really warming to you and I want to see you with that starry look in your eyes more often.” Sandy smiled at Ellen then gave the sissy a wet kiss on the side of her face and giggled as Roberts beckoned them into a huge bedroom at the end of the hall.  She and Carl settled into a dark corner on a huge leather sofa out of the glare of Roberts lighting, where they could watch and be intimate, unseen. The two as aroused as the performers as they watched the pair strip and the sweet sissy led like a lamb to the waiting bed by the elegant buxom redhead.  As they faced each-other by the bed, the little sissy was already fully erect with sheer excitement; her eyes glazed with wonder as the mature beauty pulled her close, for a soft kiss before ordering her onto the bed.

Now Ellens cock rose as she had the sissy kneel on the bed; her soft white skin contrasting with the black silk cover. Ellen softly caressed the cleft of Bellas buttocks with her finger; the reaction of the contact with her anus making Bellas cock bob sweetly; the sissy looking up at her firm controlling mistress with wide eyes.  Ellen licked her finger before choosing a silky cord and tying Bellas hands behind her back. She then stood and had Bella lick her cock for the first time; as Bella willing sucked on Ellens cock from the edge of the bed, the mature redhead smiled as she reached down to meet the sissys own yearning erection; the tips of her fingers revealing Bells glistening little bell-end, slick with sweet lubrication from pre-cum already.  Sensing the sissys urgent excitement, Ellen withdrew her cock and had the sissy lay face down on the bed; now she bound Bella at the knees and ankles.  Bella was in ecstasy and rubbed her stiff little cock against the silk; enjoying thoroughly the full eroticism of her submissiveness, oh how she wanted to be punished and abused now.  Roberts looked from behind suitable screening, not wishing to distract either t-girl as he worked the various cameras; his cock ached for relief too, and the next episode would mean he could not deny his urge to indulge himself.

Ellen sat on the soft black silk; her elegant feminine limbs with pale skin and freckles also contrasting sweetly.  She rubbed the soft white bottom of the bound sissy, which arched up gratefully to meet the probing fingers of the mature shemale who could do as she pleased with her.  Bella was already very close to coming and dreamed of being whipped or caned severely; her little cock wanted to stroke the silken sheets, and the redheaded mistress took great pleasure in teasing the sissy, making her arch her bottom all the more, which brought her stiff little cock away from the ecstatic comfort of the sheets. Ellen laughed audibly as she sensed the sweet enjoyment Bella got from the tease; she was so submissive.  She poked a finger deep into her tight virginal anus.

“Well sissy, I think its time you had something more than a finger in there; Im going to have you submit completely to me.” Bellas stomach fluttered and her little cock pulsed with excitement; what was to happen to her, was she to be fucked at last? She squirmed uncontrollably against the tight bonds, feeling them bite into her wrists, knees and ankles as she flexed her feeble muscles in an attempt to incur a little pain. Bella had not known such erotic pleasure and was close to coming when Ellen put her arm under her sweet little belly, lifting her bottom to ensure she was not allowed to come. Not just yet.  Bella writhed and whimpered expectantly as Ellen produced a wicked but slender dildo; she wanted the sissy to know pleasure in captivity, but would not use anything on her which would spoil the pleasure of her first cock.  Ellen put on a triumphant look for the cameras as she continued the tease, showing the phallus to Bella and pressing it to her lips.

“Now sissy, you give this a good sucking so its nice and lubricated; we both know where its going next, dont we?”  Bella sucked and sucked on the dildo like a baby with a comforter she stared wildly at the dominant redhead; oh how she wanted to be violated. When Ellen was good and ready, she withdrew the warmed and lubricated dildo and lifted the sissy up on her knees, face in the silk, making sure her sweet little anus was pointing toward at least one of the video cameras.  Bella gasped as the redhead licked her tangy little bottom, probing deep with her tongue, enjoying the sweet taste of the submissive sissy.  Then she eased the dildo into her tight little bottom for the first time. Bella squealed with a mixture of pleasure, discomfort and sheer erotic excitement as Ellen smiled wickedly and eased four or five inches into the sissys virginal bottom.

Behind the screen, Roberts shot wad after wad of hot cream from his rigid cock; he could not resist any longer.  Distant murmurings were also heard from the direction of the sofa, as Carls genuine phallus entertained Sandy.

Bellas little cock throbbed as the bonds held her tightly and the dildo was slipped teasingly in and out her bottom. Ellen was ready to deliver her sissy now.

“Youll come for me now sissy; I want to see a good show on that black silk.” With that she smiled sweetly and clasped Bellas little sissy cock with her free hand, and then stroked it mercilessly, making sure to tease the little bell-end with her thumb.  Bella bathed in a sea of submissive ecstasy as the redhead sneered and teased, probed her sweet anus and manipulated her captured cock. Bella moaned long and hard as she tensed to enjoy her bondage and the complete control she was under, as the pleasure of a luscious orgasm washed through her.  Ellen watched with satisfaction as the sissys little balls tensed tightly and her delirious moan of utter surrender was greeted with generous jets of hot milky cream which Bella spent gratefully on the black silk.  Still bound and helpless, Bella was then to perform her duty in relieving Ellen who know knelt before her and lifted the sissys head.  Bella sucked lovingly on the redheads aching cock, and as Ellen too, reached that sweet Shangri-La, Bella willingly swallowed her mistresss gift with gusto.

Roberts was more than pleased with the nights work and Ellen cuddled Bella with some affection as did Sandy.  Ellen was now more determined than ever to ensure Bella received an even greater reward…

Review This Story || Author: Midsummerman
Previous Chapter Back to Content & Review of this story Next Chapter Display the whole story in new window (text only) Previous Story Back to List of Newest Stories Next Story Back to BDSM Library Home