The Making Of A Sissy - Part One free porn video

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She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father. Jane's strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy's mind. Jane's girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places, dressed in pink frilly skirts, where he learned to be humiliated. He was shown to the packs of small boys who knew the girls; they made it quite obvious to them that their petit and fluffy short haired sister was a boy. Sometimes the girls would take an audience of boys behind the mall and make their sissy lift his pink skirt and drop his panties; they would all have a good laugh at his tiny cock as he blushed as pink as his pretty dress. Though a little hurt, he secretly enjoyed the humiliation, and loved the fact that other more masculine boys enjoyed seeing his little cock; when puberty came he would enjoy it all the more. As he grew up he was treated to an extreme regime of spankings and canings by Jane and a circle of ladies she associated with. He was sent to a special private school where he and other sissies were outnumbered by girls by one to ten; everyone was dressed in girl's clothes and the sissies were made to know their place by frequently being spanked and caned before a class of grinning girls. All the teaching staff were female; the sissies were immersed in an ocean of femininity on a daily basis, they were made to parade their femininity each morning before the entire school at assembly; those who had committed some misdemeanour were made to stand on stage, panties down, their little cocks on show to the teasing girls. There was no playing in the dirt and climbing trees with other boys; the fate of the sissy had been sealed on their showing their feminine side, the womenfolk would ensure the sweet surrender of their masculinity completely. One event which stuck in the mind of Bella was her progression to puberty; Jane's girls were encouraged to tease the sissy's little genitals at every opportunity as they dressed her. One morning whilst with silky pink panties hallway up her milky thighs, Bella's cock was being rubbed as she admired the developing breasts of the young girls as they displayed their puberty proudly whilst humiliating their sissy; a strange tingling feeling came over her, and she was bathed in a delicious warm feeling as her little cock spent its milky cream for the first time. One of the girls ran grinning to get her mother. "Momma! Bella has made an awful mess on the carpet!" Her strict aunt appeared as the sissy's limp little dick hung forlorn and dribbling; Jane's face beaming with satisfaction. "You bad little sissy! You shall have a special caning to go in hand with your special treatment which will start this very day." Bella did not know it, but she was about to embark on a strict regime of hormone treatment. The girls were all taken downstairs with Bella; they sat in a row, grinning with satisfaction as Bella was laid face down on the leather couch as usual; her pretty dress pulled up, her panties around her knees, her soft white bottom a perfect target. Bella eyed the smiling girls and the dominant form of Aunt Jane, in tight dress and blouse with wickedly flexible cane at the ready. Bell smiled to herself as the cane wooshed down for the first time; beneath her, a stiff little cock rubbed the leather sweetly as the sissy enjoyed a caning as never before, the sting of the cane made her cry real tears, but the feeling she now experienced in her little cock outweighed any pain delivered by her cruel aunt. Bella squirmed in ecstasy as the girls laughed at her tears. Jane handed Bella a tissue to clean the dribbles from the black leather and then dabbed away the tears. The girls gathered round as Bella was led into the kitchen where a top cupboard was opened revealing many bottles of pills and potions. Jane took one of them and several of the pills were given to Bella; Jane rubbed Bella's nipples on her flat little chest. "You have some catching up to do with your sisters; we'll soon have a little bra on you, now that you are ready to grow up." The other girls giggled with delight, and unseen, Bella's little cock stood rigidly, in full enjoyment of being a sissy. The trips to the mall got more exciting now; Bella could not wait to be dressed when she knew a viewing by the boys would happen. Tara, the oldest of the girls, now had full breasts and played with herself every night; she would select certain boys at the mall who would pay her what little money they had for 'special' viewings. Round the back in the shelter of the stores dumpsters, the chosen boys would be allowed to rub Tara's pussy and sniff their fingers, but the main attraction was the novelty of Bella; her pretty developing feminine shape with its little extra, had the boy's curiosity. They were all allowed one minute to rub her stiff little hairless cock; Bella stood panties down in glorious humiliation as she was pleasured by the boys; she would hold back until one of the regular boys whom she favoured had his turn. She would smile sweetly at him, and he at her, as she shuddered in sweet ecstasy and shot her mess just for him. The others would all laugh hysterically as she spent. His treat for making her show was to have Bella return the favour; Adam, as he was called, grimaced as he sniffed at Bella's hair and looked her in the eyes as he gratefully spurted his cream. Bella smiled sweetly as he came; her little bottom tingling with a strange new feeling, which she was sure Adam felt too. Bella yearned for Adam at night and masturbated as she squeezed her soft little breasts, which were developing nicely. Across town, a boy called Adam tried to masturbate over pictures of naked women in a magazine he had under his bed, but found whenever he closed his eyes he thought of sweet Bella; his sweetest orgasms were courtesy of the sissy he had seen over the years, taunted and pleasured, he wrestled with his feelings but it was hopeless; he desired Bella like nothing else on earth. He could not wait to see her again... 2 As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the girls were especially pleased on those occasions when Bella was held naked before the mirror as they stroked and admired her sweet white thighs and bottom, cupped her deliciously formed breasts; the smiling girls actions making Bella's sissy hairless cock rise with excitement. This gave Tara licence to administer a spanking in front of the other two girls; Jane having given the older girl this authority over Bella; the sissy well and truly knew her place. Jane smiled with satisfaction on viewing her arrogant elder daughter bring tears from Bella as her hand brought a rosy warmth to the exquisitely formed feminine shape which lay submissively across the haughty girl's lap; the hormone treatment was working better than she or any of her feminist friends could have imagined. Bella was of an acceptable age now; Jane would soon be inviting some prominent middle-aged males to the circle; Bella would be shortly be used to entertain them, she intended selling her to the highest bidder when the time came. Now Bella had come of age she was no longer simply dressed in pink frilly dresses; though she was still paraded on a Sunday in such attire the girls, with Jane's full approval, would often show off Bella's feminine beauty with more slutty outfits. Her hair had grown long and soft and was oft tied in a pony-tail now; she was adorned with black stockings and stilettos, a tight short skirt which accentuated her now perfect round bottom, tight thick patent leather belt which squeezed her slim waist, and a tight white silk blouse, her sweet little cleavage peeping through the top enticingly. Though the girls still taunted her and made her feel inferior at every chance, Bella was so proud to be a sissy, and the girls taunts only pandered to her submissive nature, ensuring her cock poked sweetly erect in her soft panties; the elasticated waist-band rubbing her excited little bell-end, and keeping it tight against her soft belly as she wiggled on her heels, chaperoned by her female betters. She was still taken to the mall, but the trips to the dumpsters behind the stores were no longer viable; the girls were much too noticeable now; their march through adolescence to ripe womanhood now complete. This of course was much to the chagrin of the boys of old who were now young men; whilst they would jostle for places in the caf? next to Tara and her two sisters, Dominique and Victoria, Bella was still an attraction to most if not all of the boys. Their attitude was different however; no longer did they taunt in the manner of old, they stood near to the sweet smelling sissy, the bulges in their jeans showing their excitement as they stroked the blushing beauty's soft hair, some of them begging Tara to be allowed to take her off somewhere, just for five minutes as they used to. They showed less interest in Tara, attractive as she was, a whiff of pussy was now easily obtained elsewhere and Tara was a very dominant girl; the boys might secretly masturbate over being caned by her, but outwardly the soft and vulnerable sissy gave them a deep novel desire. Bella could not even walk to the toilets without being followed by a troop of males, watching the sweet bottom wiggle and pinching and stroking it playfully at every opportunity. Tara grew tired of this as each trip followed a similar pattern but with growing intensity. Bella bathed in the erotic atmosphere of being an object of desire; her panties would have to be changed immediately she got home; sometimes she would actually ejaculate at the thought of these boys taking her away somewhere, stripping and humiliating her, being made to pleasure them en masse. If only poor Bella knew what awaited her so soon at home. Then there was the one boy who was now a handsome young man, who looked at Bella so differently before and now again when their eyes met. Adam yearned more than any other of the boys for a return to the dumpsters, not just for gratification, but simply to be able to hold Bella with affection. Bella did her best to show what little assertion a sissy could muster, in order to remove whoever sat next to her and allow Adam the chance to sit and feel her special warmth for him; this was impossible on most occasions due to the crowd of boys who would all jostle for contention. Ready for this on one occasion, Bella managed to meet with Adam as she left the haven of the Ladies toilet. Unseen she deftly passed a bag to Adam which he clenched as though it were his very lifeblood, and quickly secreted it down his jacket; he opened it later to reveal a pair of Bella's sweetly scented panties and a little daintily written letter, pouring out her yearning for him. The affection that was there was not unnoticed by Tara, who had designs on Adam herself. She had a plan and intended having Adam on his knees before her; her pussy tingled, she would break him. When the girls returned home that evening, there were other people in the lounge. Jane hastily ushered the girls upstairs. Bella was made to undress. The girls giggled and Jane smile contentedly as the ripe and now very desirable sissy was made to wear nothing but a white smock top, which barely covered her hips; the lower part of her sweet bottom remained on show, as did her little sissy cock which dangled at the front, her little round breasts puffing the smock out, somehow emphasising her virginal status. "You girls stay here; Bella, you'll come with me. You are going to be a good little sissy for me tonight. I have some friends who want to see you." Bella was frightened, but the situation made her erect and her bottom tingled; what was to happen to her? The girls were most despondent at not being allowed to witness what the sissy was to face. They waited till she was led quivering away by their mother, then crept downstairs to peep through the lounge keyhole. There were many stern faced women there, and sever middle-aged suited males. They all eyed Bella with wicked smiles and applauded Jane, who looked very satisfied. She smiled at one of the males who nodded back and now approached Bella who had been made to kneel on the floor. The man smiled as he undid his trousers to reveal a stiff and excited cock. Bella's little cock dribbled pee, she was that scared. The man put his hand under her chin. "Don't worry, I shan't hurt you, you'll learn to enjoy being a sweet little sissy after tonight." The audience murmured their approval and watched intently as he flexed his large hairy cock before Bella's nose. The girls gasped as they jostled to get a peep through the keyhole. Across town, Adam was blissfully unaware of Bella's situation, and was stroking his cock for the umpteenth time, the crotch of Bella's panties across his nose as he spurted as best he could from his spent balls at the sweet scent of the sissy he desired... 3 Before the audience at Aunt Jane's house, Bella cowered before the man, who gently put his hand behind her head and pressed against her soft hair as he coaxed the sweet pale complexion of her pretty face and pink lips toward his stiff and excited member. The man so wanted to slap Bella's face and see the sissy cry as she were made to indulge him, but he knew he was under the watchful eye of Jane and did not want to spoil any future chance he would have of having his way completely with this delicious effeminate beauty; his cock had risen like never before when he viewed the sweet little bottom as Bella entered, his mind ran riot as he thought of releasing his seed deep within that soft haven, and of hearing the sissy cry out as his rigid cock punished the tight little aperture, probing long and hard with exquisite satisfaction. Poor Bella smelt the dull ammonia tinged whiff of a mature erect penis for the first time as the slimy purplish bell-end touched her reluctant lips; the warmth of both equally feverish. She knew she would have to comply as the hand pressed urgently behind her head; tears began to well up and the man involuntarily groaned with satisfaction as his cock slipped into Bella's hot little mouth. Though scared by this new situation, her bottom tingled as she felt all eyes upon her, and began to suck instinctively on the rigid pulsing cock which threatened to choke her. The watching men and women sighed and softly giggled a s Bella's tingling bottom was now accompanied by the growing erection of her little hairless cock; the reaction being more to do with fear than any pleasure she had from indulging the man, though poor Bella's submissive nature was overwhelmed by the eroticism of being totally humiliated and owned. The men in the audience now sneered audibly as Bella gagged and spluttered as the 'Uncle' increased his rhythm and urgency; the women smiled with contentment, Bella was how they would like to see most males developed, and oh, how they would like to cane that sissy to tears. The man looked down to see Bella's little pink bell-end poking up beyond the frill of the white smock, and felt his balls spasm; he pulled down on Bella's hair as he stroked his cock in and out. "Look at me sissy, I want to see your eyes." Bella looked up at the man as tears rolled down her cheeks, and saliva and pre-cum dribbled down her chin; he smiled with satisfaction as he saw the fear in the sissy's eyes; he owned her for the moment and that moment was pure ecstasy for him as he unloaded his hot seed. Bella gagged and could not help but swallow the salty cum; she had no alternative, as the man grimaced with carnal pleasure. The audience softly applauded and his hips jerked several times as he spent liberally at the expense of the debutant sissy. Bella cried openly as he withdrew his sticky cock. Jane and another woman immediately took Bella to one side, wiping her face and chin. The man wiped his cock with a tissue, secreted it back within his flies, and sat down smiling with other males who waited for a favour of their own. Jane stroked Bella's hair and smiled at her with some satisfaction, wiping her soft distressed face with a baby wipe and squeezing her as though she had become an affectionate mother all of a sudden. "Good girl Bella! See how you've pleased all these people; they are all so glad to see you and you did very well. You mustn't fret, I won't let any of the men hurt you, and I saw how you started to enjoy yourself, though I know you would never admit it. I know how you like boys, and you will soon learn to like our men friends; see how some of the other sissies are pleased to be here." Bella now noticed for the first time that some of the females across the smoky and dimly lit room were receiving more attention than others. One of them winked playfully at her as their eyes met; the male on whose lap the girl sat, had a far-away look of concentration on his face as the attractive sissy squirmed in his lap; as she looked down Bella noticed the sissy's panties were round her ankles. Bella was still scared but felt her little cock stiffen at the sight. She had found pleasure in inserting things into her bottom; a pleasure which was enhanced when she fantasised about Adam, and how she wished she could be with him rather than the weathered looking males who continued to ogle her. Jane noted her sissy's excitement and knew she'd cooperate a little easier if her nerves were calmed a little; she gestured to one of the sissies across the room that was dressed as a French maid and was pouring vodka and cokes. "Well Bella, I think now you are old enough you should have a little drink to celebrate, and then we'll introduce you to a few more of my friends." The shapely maid looked at Bella with some admiration as she poured her a generous measure of vodka in a tall glass which she topped up with coke; she then did the same for herself and sat with Bella as Jane was distracted by a bullish male who was no doubt impatient to make Bella's acquaintance. The maid smiled in a sweet friendly way, making Bella feel at ease; she choked a little on her first gulp of the strong drink as the maid put her hand on Bella's knee. "You are so pretty and I thought you did very well out there. New sissies are always thrown in at the deep-end; the circle has found this to be the best way as it stops them from becoming discouraged, so you must not feel too badly about the man who was lucky enough to be chosen for your first act. I know it's hard for you, but you'll be well looked after; I'd love to be friends with you, would you like my phone number?" Bella was overwhelmed at the pretty maid's offer and was eager to be in contact with anyone outside the strict regime of her adopted family. "I'd love to, but I'm not allowed a phone; my sisters have them but I'm only allowed to use theirs when I have to arrange appointments for them. You are so nice." The maid was a little shocked at Bella's revelation, but was aware that some Mistresses and Masters had conditioning lifestyles in which their sissies were raised, but the maid reasoned that if Bella were now old enough to drink, she was old enough to have a phone. "Bella, my name is Sandy and I want to be your friend; I have a phone you can have. I noticed a large vase by the door as I came in, I'm going to leave it in there with a few notes about how it's used and the numbers you can reach me on; it'll be our little secret, don't get caught with it!" Sandy gave Bella a soft peck on the cheek; poured her another drink and then gestured to the people she was with that she needed the toilet, and the door usher allowed her from the room. Sandy caught a glimpse of several pairs of feminine legs disappearing up the stairs as she left the room and guessed these were Bella's sisters; she knew she would have to be careful. She wrote out a few notes and numbers as she sat on the toilet and wrapped the phone in them. As she descended the stairs she was careful to check she was unseen and put her slender arm into the vase and left her gift. As she went back into the room she could see Bella was being lined up for another suitor by Jane. Bella was oblivious to this, due to a mixture of the alcohol which had had immediate effect, and more so the warm excitement of having made a friend. Her eyes met with Sandy's as she re-entered and Bella mimed 'thank you so much' just as Jane took her arm and had her sit with another portly male. The man had Bella lay across him as he undid his flies. He unbuttoned his shirt and had her stroke the thick carpet of hair on his chest; Bella was unsure if she liked this or not, she had never encountered a mature man, though something inside her tingled at the thought that this may have been how she was meant to be, but she was so glad she was effeminate and she could not help becoming erect at the thought of being owned by such an animal. The alcohol had calmed her significantly and Sandy's friendship had put her at ease too; the alcohol also seemed to fuel her submissiveness and the male had simply to point to his stiff and bulging member and Bella knew what she must do; it was futile for her to even think of refusing to oblige, she knew she would receive a severe caning from Jane if she were upset in any way. Bella whimpered a little as she took a rigid and sticky cock into her sweet mouth for the second time that evening. Outside, the girls who had now regained their keyhole position, oblivious to Sandy's mission, toyed with their moist pussies as they viewed the sissy's ordeal with great satisfaction. Bella took solace in the effects of the vodka and dreamed of her Adam as she sucked almost lovingly on the grateful males pulsing member; her own little erect cock rubbed on his leg under her as she rocked back and forth in her submissive servitude. The male was suitably impressed with her efforts and as he looked at her sweet white bottom poking invitingly up, he further indulged himself by reaching across, putting his fingers in the soft cleft of her buttocks. Bella's little cock pulsed rigidly as she felt the man's finger slip into her sweet little anus, probing as deep as he dare, enjoying the tight warmth. He imagined how just how tight her virginal sissy pussy would be, on the first lucky cock to force it's way in there; he looked at the sweet little face engorged on his cock and thought how the tears would flow as she was truly owned fir the first time. Bella had her own sweet imaginative thoughts as the finger probed and excited her tight hot rectum. A small crowd, including the watchful Jane, had gathered round to leer at the beautiful sissy being put to god use; some of the men openly masturbating their stiff cocks as they watched and waited. Bella was now enveloped in an erotic fantasy, she was oblivious to the identity of the male she was servicing and thought of only one person as her cock rubbed urgently and she sucked the swollen helmet which filled her mouth; the pleasure completed by the probing finger which slipped in and out of her tingling anus. Bella was going to come. She moaned softly as did the male; he pulled his finger, claw-like as he braced himself for a glorious orgasm; the action bringing Bella to a point of no return; she moaned and whimpered in absolute ecstasy as her mouth was filled with hot semen. Her own little cock spurted in heavenly surrender as wave after wave of pleasure coursed through her body. She sucked and spluttered on the moaning male's hot milky offering as her bottom clenched against the finger, now up to the hand inside her tender anus. The crowd applauded and a couple of the men went further than they had originally intended; shooting their hot cream on Bella's soft white legs with wholly indulgent satisfaction. One of the males stood with erect cock and put one hand on Bella's cheeks, tempted to take the sissy as his, only to have Jane wave him away with an indignant smile; Bella was to retain her virginity for a while yet. Sandy sighed and prepared another vodka for her new friend; she knew the evening was far from over for her yet. Outside the door, three young women were fraught with a mixture of eroticism and jealousy. The elder of the three was determined she would make that sissy pay for it... 4 After an exhausting evening Bella was made to wait at the door and humbly kiss the guests as they left; some of the males groping her pretty arse as they departed. She was glad of the alcohol she had been treated to as this masked from her the ugliness of some of the brutes she had been forced to entertain, though she remained reasonably coherent. Bella eyed the vase in which the phone was hidden, which was tantalisingly close. Jane ushered her into the embrace of one of the leaving males, who was also a little worse for wear; he cupped the sissy's sweet little balls in one hand as he pulled her pretty little face toward his with the other. "Ohhhh! I so want to take you home with me now and ride your gorgeous little ass!" he stumbled and slurred as he spoke; Jane took hold of him, concerned he might make a meal of leaving and shepherded him to the doorway. Now was Bella's chance; as Jane's back was turned in assisting her guest, Bella deftly dipped into the vase and retrieved the phone wrapped in notepaper. "I must just go to the toilet Aunt Jane." Making full use of her apparent inebriation, she swiftly ascended the stairs before receiving the usual confirmation that this was acceptable from her stern aunt. She saw the light was on in the room where the girls were, and quietly tiptoed to her bedroom door, slipped in and tucked the phone under her bed before going back to the toilet. As she left, Tara appeared at her bedroom door, on hearing the toilet flush. "I want to see you before you go to bed sissy! You make sure you come in here when you're allowed up." Bella tingled at what Tar might want; she was as much in fear of her as she was her aunt. Jane was not pleased when Bella came down again; she was waiting impatiently with another leering male who was not displeased in any way at watching the sweet feminine legs descend from the top of the stairs; the vista allowing him a peep up at her soft genitalia. Jane frowned and pointed to the floor at her feet. "Bend over!" Bella did so and the man leered all the more, and with a contented smile as Jane lifted the smock to reveal Bella's sweet white cheeks. Jane slapped the delicate target smartly, making the cheeks wobble sweetly; a red hand mark blossomed across the sissy's bottom. "How dare you do as you please! What must our guests think of a sissy who does not wait for confirmation from her betters and keeps those guests waiting as well? I think we'll be seeing this gentleman again tomorrow; I think he should cane you!" Bella looked up at Jane and the man with eyes that welled with the sting of her mistress's hand. The man could not believe his luck; he looked at the submissive little sissy now quivering before him; his cock rose rigidly in his underwear as he thought of disciplining that sweet bottom and hearing the sissy cry real tears just for him. He kissed her tenderly on the cheek. "I shall see you tomorrow then." Bella's little cock swelled too as she watched the burly male squeeze Jane cheekily as he left; his vast frame dwarfing her. She wondered how it would feel to be caned by such a large man; she was scared but her submissive side relished how she might enjoy the pain. Jane simply pointed up the stairs when he left, and Bella ascended once more. What could Tara want of her? Bella went meekly into the room where the sisters sat cross-legged on the beds, eyeing her with severe half-smiles; Tara pointed to the floor in front of her. "Get over here and kneel in front of me!" Bella did so as Victoria and Dominique chuckled at her complete and utter servility when facing their sister. Bella cowered as Tara uncrossed her legs and rubbed the camel- toe of her pussy through her panties; the two sisters followed suit, all three were well and truly aroused by the spectacle they had witnessed earlier, stiff erect cocks spurting loops of milky white cream still fresh in their minds. Both Victoria and Dominique had secretly masturbated to orgasm in the toilet already, but Tara had saved herself; she would have someone perform the task for her. The soft feminine scent of arousal instantly permeated the room as the girl's open legs wafted the aroma of their sticky pussies. Tara was impatient and barked at Bella. "Take my panties off for me right now! We saw what you were doing with those filthy men. You have a cock just like them; don't you know you should appreciate a woman?" Bella did, but not to the extent that her sissy feelings had for men and boys; she so wanted to be a girl and was strangely jealous of the sweet smelling slit and puffy lips which were revealed as she meekly removed Tara's sopping panties. "You have a good sniff of those and lie down face up on the bed; I have a little job for you." The girls laughed at Bella as her little cock rose involuntarily with the scent and excitement. Tara climbed onto the bed and straddled her face; Bella had tasted semen for the first time, and now she would taste pussy for the first time also. She was helpless as she watched Tara's inviting pussy and arsehole slowly descend on her face. The other girls came across and took turns playing with the now stiff sissy cock. Bella's emotions were pulled one way and another as she sampled the rich and heady taste and aroma of her step-sister's womanhood, whilst the delicate feminine hands of the other two took great delight in masturbating her little cock. Tara moaned lovingly and victoriously as she rocked herself to a crescendo on the submissive sissy's face. As she did so, Dominique laughed wickedly as she felt Bella spasm uncontrollably; the sissy's muffled cries just audible as her stiff little cock spent sweetly; her cream shooting skyward in sweet submission to the girls. Tara sighed with pleasure as her delicious orgasm subsided, then she giggled wickedly; she had one more torment for poor Bella. "What do you think Adam will say when we tell him you've been with old men? I bet he won't want you anymore; I may have him fuck me, I might even let you watch." The girls laughed as Bella left the room in tears. How she wanted to use that phone now...

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The Making of a Sissy Part Ten

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 Bella’s little hand and squeezed it tightly; though she had only just met this...

1 year ago
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The Making of a Sissy Boy Slut Part 5

I hope you enjoy it and welcome your constructive comments. Thanks for reading - it's why I write! P.S. Apologies for speech marks turning out as "?" - it looks fine before I publish. --------------------------------------------------------------------------------------------------------- The next morning, having gone through my normal ritual of showering and using the douche on my boy cunt as I had been instructed by my mistress, I pulled on my silk crotchless panties and admired...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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The Making of A SissyPart Five

Bella washed away her tears and the various aromas of the night in her en-suite shower cubicle, shampooing her soft brown hair free of the semen deposited by the males and the womanly essence of Tara. After drying her soft downy body she retreated to her silky bed, shuddered and cried a little more as she remembered what she had been subjected too. Tara was mean, but was also right; what would Adam think of her? She toyed with the phone and the instructions given by Sandy, luckily, the other...

3 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

3 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

1 year ago
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The Making of A SissyPart Two

As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the girls were especially pleased on those occasions when Bella was held naked before the mirror as they stroked and admired her sweet white thighs and bottom, cupped her deliciously formed breasts; the...

1 year ago
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Andrew The Unsuspecting Sissy Part IV

ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

4 years ago
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My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

2 years ago
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Mommys Dirty Sissy Slut part 1

Mommy's Dirty Sissy Slut part 1 by dirteesissy "Answer the door for me, Brother Dearest and make sure to greet my guests Properly!" I headed to the front door, shame filling my heart, as I tottered on 5" stiletto heels. Not the usual footwear for a 20 year old man, but I couldn't have looked less like a male dressed as I was. Chapter 1. Last week my sister, Alicia, caught me masturbating to stories on a website called Fictionmania. In most cases this would have been...

1 year ago
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Trucker Daddy gets himself a New Sissy part 1 and 2

TRUCKER DADDY GETS HIMSELF A SISSY BY DEEWET It could easily be the lowest point in Denny's life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truck Stop. He almost jumped out of his skin when someone knocked on the window. Denny...

4 years ago
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Andrew The Unsuspecting Sissy Part V

ANDREW THE UNSUSPECTING SISSY PART V [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM BRECKMAN: BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

2 years ago
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Maid to Measure or Sissy Slave by Design Part One

(Note from Author - This final more polished version would not have been possible without the very kind help I received from Vickie Tern. Thanks again Vickie) Maid to Measure or Sissy Slave By Design, Part One [by Mistress Kathrine] Nick It was early on Monday morning when the CEO himself knocked on Nick's office door and asked if he was busy? Nick had never said anything more than hello a few times to the man. What was this all...

3 years ago
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The Making of a Sissy Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. 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, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to...

3 years ago
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Maid to Measure or Sissy Slave by Design Part Two

Maid to Measure, or Sissy Slave by Design, Part Two By Mistress Kathrine The room was very bright. It hurt to open his eyes so he tried to cover them with his hand but found he couldn't move it. He started going over carefully the last things he could remember. He was in a beautiful home, Kathrine? No Mistress? Oh if only he could wake up and remember what happened? As his mind began to clear he could start to see more clearly. It looked like he was in a...

1 year ago
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Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

3 years ago
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The Making of A SissyPart One

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father. Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind. Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew The Unsuspecting Sissy Part VII

ANDREW THE UNSUSPECTING SISSY PART VII [email protected] *** A NOTE TO ANDREWS' FANS: I DON'T GET VERY MUCH FEEDBACK, PERHAPS 4 OR 5 PEOPLE WITH EACH CHAPTER. WHILE I APPRECIATE THE SUPPORT FROM THOSE THAT ENJOY THE STORY, I CAN'T SEE CONTINUING THE TALE IF SEEMINGLY VERY FEW PEOPLE ARE INTERESTED. SO, IF YOU ENJOY THE STORY, OR DON'T, PLEASE LET ME KNOW! MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN...

3 years ago
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Maid to Measure or Sissy Slave by Deesign Part 3

With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...

1 year ago
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A sissy called Jezebel Part XX

A sissy called Jezebel Part XX - Jezebel and hir entire family next attend a family wedding, where the bride is a sissy (of course.) What sexy, submissive traditions prepare the beautiful blushing bride for hir big day? Will our bride vow to love, cherish and (especially) obey, all orders, whims, without any hesitation, from hir goddess/wife/mistress and to her complete and utter satisfaction? There is non-stop teasing in the car about the bridesmaid dress. Everyone knows I adore...

3 years ago
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The Making of a Sissy Boy Slut Part 2

If you have not already done so, it may be best to read part 1 first. Your comments and ratings are always welcome. I hope you enjoy the series. M ------------------------------------------------------------------------------------------------------ The next morning, as I gradually awoke from a restful sleep, I became aware of atightness in my groin. With a start, the previous evening’s events flooded back to me as I reached down to find the thick elastic band still stretched around my...

1 year ago
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My Sissy Life Part 17

My Sissy Life Part 17 I fixed my make up and went back to cleaning, I didn't want to get into trouble because my chores weren't done. I don't know how I would explain that, 'I'm sorry mother I couldn't finish dusting because I was too busy sucking Jake's cock.'. That is not a conversation I wanted to have. I wasn't sure what was going to happen when Jake babysat me for the weekend. I had an idea that there would be a repeat of what just happened. The rest of the night. I served...

3 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Mein erstes Mal als Sissy Part 10

Fortsetzung von:https://de.xhamster.com/stories/mein-erstes-mal-als-sissy-part-9-708712„Hallo meine kleine Schlampe“, begrüßt er mich nachdem er mich ein Zeit lang mehr oder weniger ignorierte. „Nun kommen wir zu meinem persönlichen Höhepunkt des Wochenendes“, er führt mich nochmal ins Bad und legt mir Dessous in Rot bereit, dazu ein rotes Negligees, die blonde Perücke lasse ich auf und er bittet mich, dass ich mich ganz nuttig für ihn zu Recht mache. Ich freue mich darauf endlich wieder von...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
3 years ago
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Rubber Sissy Panties Part 2

Rubber Sissy Panties Part II Clark woke up at work. He was dressed in the same clothes as in the previous day, shaven and the clothes were clean and ironed to perfection. He looked at the clock on his computer, and it was 7am, way earlier than anyone else would be hanging around. He raised himself off his chair and walked to the W/C, ready to relieve his full bladder. Not noticing his own behavior, he lowers his pants and sits down on the toilet, and points his sissy clitty...

4 years ago
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Blackmailed Sissy Whore Part Three

Blackmailed Sissy Whore Part 3 I did manage to get a little sleep. After Tiffany finally zonked out, and the continual grinding on my thigh and the relentless playing with my nipple rings stopped, I couldn't keep my eyes open any longer. Friday night was the last full night's sleep I had gotten since Marcus took over my computer, and my life. I woke up before my alarm went off, which was a good thing. I was tangled up in limbs so securely, it took me several minutes to snake my way...

2 years ago
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Lockdown Sissy part 1

Author's Note: Thanks to those who have reached out to me with story ideas. It's been difficult to get any writing done these past few months, but hopefully my head is finally back in writing mode. I hope you enjoy this nasty little fantasy. Please let me know if you have any thoughts or ideas--either here in the comments or directly at [email protected] xoxox Emshoninque Lockdown Sissy- part 1 I made a resolution to become a better sissy in 2020. It's something that has...

2 years ago
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The Making of a Sissy Boy Slut Part 4

--------------------------------------------------------------------------------------------------------------------------------------------- I spent the next hour on my own, cleaning myself up and tidying away the training equipment in the kitchen, until my attention was drawn to preparing my cum meal for the following evening. Miss Marsh had left me with a small Tupperware container, complete with lid so as it could be transported easily during my journey the following night, though I had...

2 years ago
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Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

1 year ago
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I Want To Be A Sissy Part 4

After my intense and strangely satisfying lipstick application initiation, all the women and young girls and the male pharmacist drifted off, allowing Judy to take control of her cute little pansy customer once again. I was dumbfounded that the woman I first saw coming towards me with what I thought was disgust in her eyes, was really a rougher, blunted extension of my darling wife, my Mistress Claire. Judy seemed perfectly happy to take command of me and my sissy needs. She proved...

1 year ago
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Black Master gets a white sissy Part one

Black Master gets a white sissyPart Onebysissy4blackmasterEvery one who saw me at work used to think I was Mr. Clean, Mr. Respectable. I work in advertising and I used to model my appearance on the sort of guys you find between the pages of GQ. Very American, very preppy. I was a nice middle-class boy with a nice expensive haircut and a nice expensive suit. I went to an up market health club to keep my body in peak condition. I'd even dated a nice girl from time to time. So you'd be right in...

3 years ago
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Andrew The Unsuspecting Sissy Part II

ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...

3 years ago
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Sissy Prudence Part 2

Sissy Prudence (Part 2) (by Sissy Caroline 22 December 2006) Section 1 "Prudence. Come here at once." Dressed in his maid's uniform, Prudence walked obediently into the room and then knelt down before his mother, his eyes lowered to her feet. He knew he was in trouble because she had called him Prudence. "I have just been talking to Mrs. Smithton, who tells me that she is increasingly concerned about the quality of your work when you are supposed to be performing maid duties...

2 years ago
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My Sissy Life Part 3

My Sissy Life Part 3 When I got to my room I saw the Hello Kitty dry erase board on my door. There was a note from my brother that said 'Sissy, I need my jock strap clean by Friday morning.' Oh good, I get to hand wash my brothers jock strap again. Is it Christmas already? Almost every day there is a note on the board from someone telling me that they want me to do something. I walked in my room. I still can't believe how ultra girlie my...

1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

2 years ago
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Mommys Dirty Sissy Slut part 2

Mommy's Dirty Sissy Slut part 2 by dirteesissy Please read part 1 before enjoying this instalment. Chapter 5. After I had finished cleaning Lisa's toilet with my tongue, she had me brush my teeth, as she finished her bath. I dried her with a fluffy white towel before helping her dress. Kneeling in front of her as she stepped into a pair of darling lacy pink thong panties, she bade me to pull them up. I obeyed and was overjoyed to serve her in such an intimate way. A pink...

3 years ago
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Becoming A Sissy Slut part 2

I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known. I rolled out of bed and stood up, my wig had fallen off in the night...

4 years ago
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A sissy called Jezebel Part VII

A sissy called Jezebel Part VII - Jezebel has finished hir tour with the Head Mistress into the secretive dungeon/reform school below the fair walls of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. But is the Head Mistress entirely done with Jezebel? Additionally, what ever does one learn in a 'sissy life skills' class? I require the gurls in my harem to crawl on the floor at home and in private at the office. So get on...

3 years ago
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Sissy Prudence Part 3

Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...

3 years ago
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Americas Next Top Sissy part 3

After waking up, Jim finds himself in a feminine bedroom with the 11 other naked men. When the Nurse from the previous night enters the room dressed in a leather cat suit and introduces herself as Ms J, she wakes the men wake up and they soon learn to behaviour or implants in their bodies will make them. Now forced to wear ultra feminine clothes and wait holding each others hand for the looming elimination! Part 3 Jim is standing in the middle of the bedroom waiting for Ms J...

2 years ago
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A sissy called Jezebel Part VI

A sissy called Jezebel Part VI - Jezebel's inspection has been completed at the Head Mistress's office of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. Jezebel is taken by the Head Mistress into the secretive dungeon/reform school below the fair walls of Templeton. All sorts of secrets and surprises are revealed. Headmistress Saxon looks at me. "What class did you just miss?" "Deportment, Headmistress." Forty five minutes...

1 year ago
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Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

2 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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Cometh the Sissy Part 1

Cometh the Sissy (Part 1) Stevie "No. No fucking way." "Ahh, c'mon honey. It'll be so much fun! It's about me not you. I just need you there as, well, sort of a training aid. I promise you that you'll love it." "It's gross, seriously, some fat old man, what the fuck are you thinking about?" "It's about power. Control. Desire. I want to see if I can do it. You'll out all day and I'm doing my online classes and shit, there's only so many dildos and vibrators. I want to...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

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