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Review This Story || Author: Midsummerman

The Making of a Sissy

Part 1

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.  Janes 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 sissys mind.  Janes 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 girls 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; Janes girls were encouraged to tease the sissys little genitals at every opportunity as they dressed her.  One morning whilst with silky pink panties hallway up her milky thighs, Bellas 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 sissys limp little dick hung forlorn and dribbling; Janes 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 Bellas nipples on her flat little chest.

“You have some catching up to do with your sisters; well soon have a little bra on you, now that you are ready to grow up.” The other girls giggled with delight, and unseen, Bellas 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 Taras 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 boys 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 Bellas 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…


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 Bellas 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 girls 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 Janes full approval, would often show off Bellas 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 café 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 beautys 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 Bellas 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, youll 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. Bellas little cock dribbled pee, she was that scared.  The man put his hand under her chin.

“Dont worry, I shant hurt you, youll 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 Bellas nose.  The girls gasped as they jostled to get a peep through the keyhole.

Across town, Adam was blissfully unaware of Bellas situation, and was stroking his cock for the umpteenth time, the crotch of Bellas panties across his nose as he spurted as best he could from his spent balls at the sweet scent of the sissy he desired…


Before the audience at Aunt Janes 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 Bellas 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 Bellas 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 Bellas 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 Bellas 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 Bellas little pink bell-end poking up beyond the frill of the white smock, and felt his balls spasm; he pulled down on Bellas 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 sissys 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 Bellas 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 youve pleased all these people; they are all so glad to see you and you did very well.  You mustnt fret, I wont 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 sissys 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 sissys excitement and knew shed 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 well 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 Bellas 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 Bellas 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 its hard for you, but youll be well looked after; Id love to be friends with you, would you like my phone number?”   Bella was overwhelmed at the pretty maids offer and was eager to be in contact with anyone outside the strict regime of her adopted family.

“Id love to, but Im not allowed a phone; my sisters have them but Im only allowed to use theirs when I have to arrange appointments for them. You are so nice.”  The maid was a little shocked at Bellas 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, Im going to leave it in there with a few notes about how its used and the numbers you can reach me on; itll be our little secret, dont 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 Bellas 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 Sandys 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 Sandys 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 Sandys mission, toyed with their moist pussies as they viewed the sissys 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.  Bellas little cock pulsed rigidly as she felt the mans 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 its 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 males 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 Bellas soft white legs with wholly indulgent satisfaction.  One of the males stood with erect cock and put one hand on Bellas 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…

Review This Story || Author: Midsummerman
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