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A Picture Perfect Sissy
🕑 Added 2022-08-06 13:18:50 +0000 UTC"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie."
Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Karen was snapping off close-ups, zooming in on Jason's puffy tits, his pretty nipples hardening between his french manicure.
I'm so responsive, Jason thought a little sadly. There's really no hope for me.
Karen looked up from behind the tripod, frowned, and Jason felt a bolt of cold terror. But as it turned out, he wasn't doing anything wrong. She'd only had an idea.
She handed him a bit of shiny jewelry.
"Put those on," she said, and checked the light in the studio. "Hurry up."
Jason fumbled a bit with the nipple clamps and Karen got impatient. Now he was doing something wrong: keeping Karen waiting. Karen hollered for her partner Sue and the small dark-skinned woman stepped from the darkroom.
"What's up?"
"Would you clip that sissy's tits, for me? The stupid little bitch seems to have forgotten how."
"Sure thing," Sue said, smirking. "I think it's just hard for him to open and close them with his new french manicure.
Jason bit his plump lower lip as Karen's partner pinched his nipples hard and clamped his poor tits. She grinned, crooked her finger around the connecting chain, and yanked on it.
"Feel good sissy?" she said. "I'll bet you just love this. Don't you?"
Jason felt his eyes fill up. There was no hiding what he felt. The evidence was there, although greatly reduced, between his creamy thighs. Sue was spritzing his tits with an atomizer now so that his beautifully moisturized skin would glisten and Karen was back down behind the camera calling out orders. There was no time to feel sad. Jason bent forward on his big sissy heels, wearing nothing else but a red garter, no panties, and red fishnet stockings. He tried not to lose his balance. He lifted his breasts, now wearing nipple clamps, and offered them to the black lens capturing him for lord only knew how many horny viewers.
"That's it, Holly, sweetheart. Offer up your breasts. Good girl. Give them away. That's it. Now blow a kiss for the camera, sissy. Nice, nice. I'm getting it, getting. Just a few more. Beautiful, girl. Now just stand there for a minute, while I change film. Leave those nipple clamps on. We're not done by a long shot. These breast torture shots always pay a fortune."
How, Jason often wondered, had this happened to him? He used to be a man and now look at him! Oh, he was still a man, alright, but only technically, as Karen loved to point out, and yet, so little a man as to be hardly one at all. To say that he had not foreseen what she would do to him was an understatement. It used to be him on the other side of the camera taking photographs of pretty women. Karen had been one of them. She had, in fact, been the prettiest, sweetest, warmest one of them all. That is why he had gone to bed with her in spite of being happily married. Now it was changed, all changed.
It was so easy, so absurdly easy, Karen often reflected. Men really were such idiots. She had always half-feared that all the jargon of male inferiority was just propaganda. But when she thought of how quickly Jason submitted to her domination and became Holly she was convinced that the truth was even more unbelievable. The idea of "male," at least for a significant portion of what is called the male population, was nothing more than a fiction. Inside most so-called males, there was a desperate, submissive sex-crazed little sissy just ready to serve.
Two days after the breast shoot, Jason was buckling himself into the big plastic platform sandals that Karen had specially ordered from an x-rated clothing store downtown. She was doing a spread for a foot-fetish site and that meant lots of shots of Jason's feet in all kinds of sexy and impossible shoes. He'd been sent to a special salon in the Village where Karen always sent him before shoots. His visits to the salon were about the closest thing Jason ever got to positive attention from women nowadays. Sure, they had poked fun of him at first, but as the months wore on, the novelty wore off, and he was just another client to service. He sat in the chair and let them do whatever Karen had written out on the piece of paper he was required to hand over upon his arrival. Yesterday, it was a simple pedicure: a light pink polish applied several times and, finally, a silver-glitter coat laid over that.
"Oh don't your little toes look so cute and sparkly," Karen had said, mockingly when he entered the studio. "Show them to Sue. Look Sue, aren't they just darling?"
The two women, dressed in their drab clothes and sensible shoes, laughed at the silly sissy with the sparkly toes. Jason felt terribly ashamed. He really did think his toes looked cute the way they looked now.
All day long Jason found himself modeling fuck-me pumps, icicle-thin stilettos, fluffy mules, wedge-heeled sandals, the more straps and bows and ribbons and buckles, the better. For his barefoot shots, he wore ankle bracelets, toe rings, and something he'd never seen before called a barefoot sandal: a kind of decorative ribbon that slipped over his toe with no sole at all. "Arch your foot, stupid," Karen would shout, or "point your pretty toes, you sissy," and Jason would do what she said, if it were possible. "Flex your toes," Karen snapped, "More," as she shot two rolls of film and loaded the camera again while Sue placed a ripe strawberry between each of Jason's toes and then covered his feet with whipped cream.
Many times he wore shoes that it was impossible to even walk in, shoes so complicated that Sue had to put on and take off his feet. But, all in all, it wasn't as difficult as some of the other shoots. He didn't, after all, have to worry about smiling, or looking seductive, or anything like that. "No one is interested in your face today Holly," Karen would snap, annoyed, when he instinctively smiled winsomely for the camera, "all you are to these perverts is a pretty pair of feet." Somehow, Jason found that a little depressing, to think his face didn't matter, although he didn't really know why. So as Karen zoomed in on his feet, Jason smiled prettily anyway.
He was wearing a pair of see-through "cinderella" plastic pumps with a five-inch plexiglas platform, sitting on a prop stool, legs crossed, letting one big shoe dangle tantalizingly off the tips of his curled up toes. Karen had told him to hold the pose for a really long time while she shot what seemed rolls and rolls of film.
"She's amazing, isn't she?" he heard Karen say, and stared through the bank of lights illuminating the makeshift set. "Best sissy model in the business. She'll do anything. I know it's hard to believe it's Jason. He's gone through so many changes. Babydoll, come here for a second."
Jason slid off the stool, trying to smooth the tight pink micro-miniskirt he wore over his ass, but there really wasn't much skirt back there to smooth.
"Oh, doesn't he just look so sweet mincing around on those platforms?" said a voice that sounded familiar to Jason, although he couldn't quite place it.
"He's such a shoe-slut," Karen said. "He always had a foot fetish. Now, he loves showing off his own pretty toes. Darling, you remember Taneesha, don't you? Oh, I see you do. It's okay. Don't be embarrassed. I told her all about you. She doesn't mind you like this. Say something nice to the poor little sissy, Taneesha."
The sexy black woman in the expensive pantsuit laughed and told Jason he had pretty legs.
"See, Holly? She thinks your legs are pretty. Is that a smile, I see?"
It was true, Jason realized, with a kind of silly hopelessness. He was smiling at the compliment from one of his former models. Karen had helped get the struggling woman a job at a big brokerage firm; the last Jason had heard, Taneesha had become a vice president.
Karen shook her head. "What a simpleton. Go fix Taneesha a gin and tonic. And a club soda for me, that's it. Hurry along. And ask Sue what she'll have, too, while you're at it."
Jason hurried to the kitchen as fast as his big plastic sissy heels would carry him. On the way out, he was thrilled to hear Taneesha tell Karen what a cute little white ass he had.
It was strange listening to the three women discuss what had happened to him. In some ways, it was almost like listening them discuss something that happened to someone else entirely. But Jason tried to listen whenever his "story" was retold in the hopes of coming to understand how he ended up the way he had. He couldn't follow it, really, and his attention always seemed to wander off. Of course, Karen would always interrupt herself to tell him to go do something for her or her guests. Other times, he would be required to pose or lift up his skirt or even show what had become of whatever was left of his manhood. As a result, Jason never really did manage to piece it altogether and what did it matter, anyhow?
Perhaps one of the best things about it all, Karen often felt, was recounting how she'd reduced Jason to his current status in life. She had transformed a filthy sexist pornographer into a simpering sissy sex slave. Now instead of profiting off oppressed women, he was doing something decent with his life: posing for photos that would generate money to further topple the patriarchy. Karen loved the shame, guilt, and fear on Jason's pretty feminized face when she spoke of his "crimes." She knew that the former Jason would have tried to excuse his work as merely harmless consensual erotica. But not anymore. He had been rehabilitated to understand the error of his ways. And he was making amends.
"I'm sorry I took so long to have you over," Karen apologized to the black businesswoman. "But I have to go slowly with her. She has so much trouble meeting people from his old life. He still remembers, I guess. It's impossible to tell how much. Enough to be ashamed at what he's become, in any event, and even more ashamed at how much he likes it."
That was true, what Karen said, about him liking what he'd become, maddeningly true. Jason couldn't help himself. He'd heard Karen talk about some kind of gender rehabilitation that had supposedly been done to him. That he had been "corrected," in some way. He wasn't sure, exactly, in what way he had been helped to see the error of his past life. He knew, though, that he had fallen helplessly in thrall with his one-time favorite model and that Karen had slowly helped him to realize his true nature. Under years of cultural conditioning, he was a sissy, and even though society looked down on him for that, it was silly to deny what—and who—he really was.
He never suspected a thing, Karen liked to say. To him, she was just another struggling pretty face. It never occurred to him that she might be a member of Project Harpy, a radical feminist group dedicated to the sissifying of the majority of the male population. With the vast financial resources at Project Harpy's disposal, a new technology had been developed for helping the average male's natural tendency to sissyhood along. It was a beautiful thing to consider, really: all the inheritances from the estates of dead husbands, all the divorce settlements…women had enormous wealth and from that capital most were willing to make generous donations, sick and tired as they were, of weak men and all their stupidities. Add to that all the revenue generated from a new porn industry using already captured sissies, and Project Harpy could project a 37% national sissification rate in the next four years. Jason's wife, Catherine, had been easily enough converted to PH's cause.
Jason always despaired a little at the mention of his ex-wife's name. He always tried not to show it, but he always failed. Karen, Taneesha, and Sue laughed now as they saw him blush to the tips of his pink painted toenails when Karen announced that Catherine would stop by the next day during the bondage shoot. He was sent out of the room for more drinks shortly thereafter and so didn't hear Taneesha volunteer some friends of hers for a very special shoot that Karen was planning. Karen wanted that particular shoot to be a surprise for Jason.
"They'll be okay with a girl like Holly?" Karen asked. "I mean, you'll explain how it is with him? She's just worth too much money to end up with anything broken."
"Oh they'll be fine with him," Taneesha assured her. "The way that sissy looks…and white, to boot? They'll treat her like a girl alright. That lil' boy is going to end up sticky and sore, I guarantee you that!"
Bondage shoots were always difficult for Jason. His arms wrenched painfully behind his back, laced into a leather mitt, cuffed and connected to a chain, he would be winched to the tips of his painted toes. Sometimes his ankles would be bound to his thighs and his bottom half hoisted and attached to the ceiling as well, leaving him fully suspended and perfectly defenseless. Sometimes he'd be laced into a punishment corset so tightly it was difficult to breathe. A ball-gag would be popped into his mouth and Sue would lace up his tiny penis with a leather cord or a satin ribbon, tying his balls off and pulling them uncomfortably backward. She'd attach the other end of the cord to the waistband of his garters. Sue was never gentle when she did these things to Jason and seemed to like hearing his muffled cries and moans through the ball gag.
The worst part, though, was the dildo that always "finished" Jason off, a long insinuating invader that was pushed into his unresisting bottom. That was the worst part because it always made his bound little penis hard, which hurt, and seemed so humiliating. The best part was that Jason didn't need to do any acting whatsoever during these shoots: the pain on his face was real, and so were his bright pretty tears.
Today Jason stood with his arms held out wide in the shape of a "Y," each wrist cuffed and attached to the ceiling. He was forced, as usual, up on his toes, but since he was wearing a pair of 5-inch platform sandals he could only sort of roll around on the fronts of the big heels. His legs had been bound together with several tight leather bands at the ankles, knees, and thighs. He was wearing a pink leather corset which held up his bare breasts, pink split crotch panties, and pink thigh-high stockings in addition to the pink platforms. His pink-painted mouth was around a ball-gag and nipple-clamps decorated his breasts. A vibrating dildo had been stuffed up his ass. His penis, tied painfully back, seemed to be replaced by a big pink bow. His eyes were very big and very afraid.
His ex-wife Catherine held a short crop of braided leather. She was dressed in a kind of catsuit that covered her from head to booted toe. Over her face, she wore a mask so she couldn't be recognized in the photos. Karen was behind the camera.
Catherine lifted her arm and Jason winced just before the blow struck him across his mostly bare ass. His nipple clamps jingled.
"Turn around, Holly," Karen ordered.
Jason was exhausted; it had been a long shoot, and he was pretty well beaten by now. Catherine always seemed to enjoy these sessions quite a bit. She seemed quite willing to beat him with the crop, or drip hot wax on his breasts, or attach weights to his nipples or genitals all afternoon long. She never seemed to get tired of abusing him.
"Turn her around," Karen said to Sue, disgustedly. "I want to see his pink ass."
Sue grabbed a tired Jason and spun his backside toward the camera. Catherine gave it a few extra swats for good measure.
He heard his ex-wife laughing. "I think he's cumming, for crissakes."
Jason hung his head rather bashfully. There was no doubt about it. He was cumming. Catherine stepped forward and spun him back the other way now so that Karen could zoom in on the tell-tale evidence. The way his penis was tucked backwards, Jason's orgasm had left his thighs, smooth and white above his stocking tops, all sticky with his fluid.
Tired as he was, Jason was still required to serve the women after he'd been released from bondage. He changed into a pair of silk tap pants and tank t, his naked feet slipped inside a pair of high-heeled mules, painted toes peeking out from the fluff, of course. He brought the women whatever they required and Catherine seemed to enjoy ordering him about like the slave he more or less had become. His ex-wife looked down at him with a mix of anger and disgust as Jason hurriedly knelt to obey an order to massage her calves, which she hadn't really wanted him to do at all. She only wanted to see how far he'd go.
"Get up you pathetic sissy," his ex-wife mocked. "I don't want your pansy hands on me." She turned to Karen. "And to think I couldn't get him to do anything around the apartment."
You have to know how to handle them, Karen explained. She loved to talk about the deconstruction of masculinity. She could teach a class on it; as a matter of fact, she often did. All sissies are basically the same, she often said, and easily manipulated. What she really loved doing was talking in this way right in front of Holly. Nothing could better demonstrate the degree of total control she had achieved than explaining exactly how she'd reconditioned her sissy and have him still be unable to do anything about it.
The fact is, Karen always saved the best for last, is that a sissy loves his fate and wouldn't have it any other way.
"You wouldn't ever want to change back, would you Holly?" Karen said, cupping Jason's chin, squeezing his cheeks so he made a big lipsticky kissy-mouth. "You don't want to go back to being a man, a husband, do you?"
Jason fluttered his long lashes and shook his head "no."
"You aren't suited for it, are you precious?"
Jason shook his head "no" again. He felt Catherine's icy, disdainful stare as he knelt there, completely subjugated and feminized, a long-haired sissy with painted nails and breasts.
"Good girl," Karen said. And she advised him mysteriously to rest up for a very special shoot the next day.
Jason had heard Karen and Sue talking about his special shoot amongst themselves and to various visitors to the studio for several days. But there was always something else to think about so he didn't fret too much over it. On this particular morning, however, Jason came into the studio feeling quite uneasy. He was dressed all in white: panties, stockings, corset, and baby-doll nightie. He was wearing his big platform white plastic sissy sandals and a white satin choker collar. His hair was teased up and finished with several pretty white satin ribbons. Jason wasn't exactly sure why he felt uneasy; he'd been dressed in similar outfits before. Perhaps it was the many enemas Sue had administered to him that morning, or the insinuating comments she'd made while watching his discomfort as she filled his insides with warm sudsy water.
Whatever uneasiness Jason felt was confirmed and compounded when he entered the studio. The lights seemed much bright, a bed dominated the set, and above it hung a a boom microphone. Jason noticed that a videocamera had replaced Karen's usual equipment on the tripod. Even more unsettling, standing on the other side of the room, behind Karen, were Taneesha and Jason's ex-wife Catherine. Leading Jason up onto to the bed, and abandoning him there, Sue took her place with the other women, presumably to watch the show.
Nervous and bewildered, Jason looked expectantly to Karen for a cue. After several more moments of checking the camera, Karen looked up and smiled.
"A little something different today Holly, sweetums. I've decided you're ready for the big time: film." Karen savored the expression of shock on Jason's face, but only for a moment, before going on. "Photo spreads are fine, but a girl of your special talents should really be doing something more…umm…demanding, not to mention lucrative. I think the audience would like to see and hear what a hot sissy slut like you can do in action."
Jason had no preparation or direction for what was to come next. Karen recorded the mixture of terror and resignation on his pretty face as Taneesha's four black friends came into the studio. Not a one of them stood less than six foot three nor weighed under two hundred fifty pounds and there was no doubt as to why they were here. They had been drinking and they were loud and aggressive and they wasted no time completely dominating the terrified sissy. Within seconds Jason found himself nervously pulling down a zipper, even while his panties were being yanked down over his hips. In short order, a black man was on the bed behind him, probing Jason's white bottom with a long, erect cock. At the same time, Jason was holding a second black cock lightly between his fingers and delicately licking delicately its fat, wet, dark purple head.
They were laughing at him now, manhandling him, commenting on what a good little bitch he was. The way they abused him was in stark contrast to the way Karen, Sue, and his ex-wife abused him. There was very little subtlety in the men's approach. They didn't tease him or humiliate him so much as treat him entirely as an object for their sexual satisfaction. Jason had often heard the term "sex-object," of course, but never had he fully realized what being a "sex-object" really meant—or what it felt like.
Karen moved in for a close-up of the black cock now pushing in and out of Jason's ass. Even she had been surprised at how easily the monstrous rod of black flesh had slipped inside the little sissy's ass. When the man in Jason's mouth started cumming, she switched focus to the semen escaping Jason's painted lips. She caught it spilling over his pretty chin and feminized fingers as Jason continued to pump the man into his mouth. One of the men not currently inside Jason couldn't wait and had began jerking himself off. Now he bucked his hips, spurting all over Jason's hair. The man in Jason's ass came, his semen soaking the tops of Jason's stockings. He passed the stunned sissy to the man who'd been impatiently waiting his turn. Jason was quickly flipped onto his back, legs thrown over a new man's shoulders, and fucked with his pretty feet waving helplessly in the air. Meanwhile, the sissy slut's mouth was once again filled with black cock while another black cock spurted cream all over his soft belly.
This is wonderful, Karen thought, simply wonderful, as she filmed the half-naked white she-male wriggling lasciviously on the bed. He has achieved total sissification. She couldn't help being impressed at how completely Jason had been transformed into Holly. At the same time, Catherine, shook her head in amazement to see just how debased her ex-husband had become. To think, she had been married to this pretty, submissive, plump-titted little slut! He was completely without shame. Looking at him now, Catherine realized Jason was a hundred times more active in bed like this than he'd ever been with her. Taneesha, sipping a drink, bent her head toward Jason's beautiful white wife, who whispered just that, and nodded, stifling a laugh. Taneesha, who'd long ago once heard Jason make several fairly innocuous but to her mind somewhat stereotyped racial comments, was quite pleased at the present arrangement. To see this once rather arrogant white male taking it up the ass, in the mouth, in the face, in the hands from four virile black brothers—that was a dream come true: and it was all being captured on videotape. As for Sue, she just grinned, winked at Karen, her lover, and, feeling incredibly aroused at Holly's total humiliation, she thought to herself, "another spineless male bites the dust."
At this point, Jason was pretty much oblivious to it all. He knew, somewhere in the back of his mind, that it was all over for him now. He knew that his ex-lover, her lesbian girlfriend, his ex-wife, his ex-employee, and soon, tens of thousands of others would be watching him fuck and suck four black studs, but somehow it didn't really matter anymore. He found himself coaxing a black cock to yet another monstrous erection with his soft sissy hands, licking and kissing it, while he was on his knees. A moment later he was being titty-fucked, holding his breasts together over a long slippery black hose, which shortly spurted into his face. He was soon sucking again, taking it up the ass, giving handjobs, tit jobs, and, after his sissy platform had been pulled off, even frigging one black cock under his soft stocking foot. The sensation of hot black semen spilling over his painted toes was indescribably wonderful. His own penis, which Sue had been demurely tied back, as usual, today with a white satin ribbon , strained to achieve an erect state. Jason wanted desperately to free it, or better still, to have one of his black assaulters free it for him. Instead, he managed an orgasm the usual way: a long slow leakage that never seemed to properly end, but kept building and ebbing, building and ebbing. He felt it building now, and at the same time his anal ring massaged the 10-inch hose in his ass so that the man attached to it grunted and cursed his satisfaction as yet another load of black cum was squirted inside Jason's little bum.
Someone was holding him up now, one enormous muscular brown arm with prison tattoos wrapped around his narrow waist, lifting Jason's body clear off the floor, his legs dangling, and he was being told by someone, maybe Karen, to look into the camera. He mustn't have obeyed fast enough because Jason felt a hand in his hair lifting his cum-drenched face towards the black lens which was zeroed right in on his dazed, rapturous expression. The man holding him growled something about him being a white sissy faggot, a bitch, a cocksucking slut, but they hadn't hurt him, and Jason knew they wouldn't. He wasn't a threat to anyone. He was just a submissive, helpless pleasure whore. Was there a cock still inside him?
"Smile honey," someone said. Yes, it was probably Karen who said it, "Smile."
And then it was his ex-wife, standing off-camera, who said, "Say sleaze, Holly. Say sleaze."
There was laughter both in front of and behind the camera.
Jason smiled weakly, contentedly, as he lisped the word.
"Sleaze…"
And then everything faded orgasmically to black.
{the end}
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