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ShadowJack's femboys
#1
Since a loooong time ago i was going to create a separate thread for ShadowJack's art and stories! Since then, his blog disappeared, I messaged him on another blog, did not get a response, found some archived pages, and, finally this is the thread with all I could "save" from the Internet.

shadowjacks-femboys.tumblr.com - original blog
patreon.com/shadowjack - removed Patreon page
https://shadowjacks-femboys.bdsmlr.com/
https://web.archive.org/web/201812102201...umblr.com/
https://e-hentai.org/g/1913935/0ea289bfa5/
https://rule34.xxx/index.php?page=post&s...shadowjack


Table of Content

Stories

Kevin Goes to the Pride Parade
Femboy in the Woodshed
Rape Me
Take Me for a Ride
When I Was a Girl
Kalen and the Sky Pirates
Locker-room Funboi

Art, Comixes

Femboy Carry-Pack
One night in a bar


Related threads

Bound men in feminine clothes and femdom fetish art
Reply
#2
 femboy_11_bondage_feminization_stockings_by_shadowjack.jpg   

ShadowJack Wrote:This is a blog about those beautiful boys who aren’t afraid to be feminine. Some look so much like girls that you can’t tell they’re not. Some actually dress up and pass as girls in their day-to-day lives. We have many names for them, but I prefer the word femboy.

This isn’t about underage boys. Just want to get that out there. Femboys, through artifice, hormones or the blessings of nature, have pronounced feminine features that sometimes make them appear more youthful than they are. Especially when you try to draw them.

I’m an artist, and I draw my femboy fantasies. The artwork I post here is original, and I insist on retaining all rights to it, but by all means reblog it if you like it.

I hope you enjoy my strange and kinky femboy fantasies…
Reply
#3
Secretly-a-Neko Wrote:Hi... I have a question. Femboys are a common fetish. But in about 99% of what's written/filmed about them, they are insulted, abused, even raped. I'm a femboy, but I'm not someone who wants to be fucked by everyone, or forced into it. I want an actual relationship, but as I said, it's hard to find someone who isn't just looking for sex. What do you think? Do you think all femboys should be treated like this or that it should be a choice? I feel like I'm the only one that feels this way... /)-(\

ShadowJack Wrote:Dear Secretly-a-Neko,

You absolutely should NOT let porn dictate your own relationships! Everyone is different, and everyone is entitled to their own feelings and preferences. For many femboys, a desire to be dominated is a big part of their sexuality.  But that doesn’t mean EVERY femboy needs to be dominated. If you don’t have these kinds of fantasies, then you should seek out partners who share the desires you do have.

The drawings and stories I create are only fantasies, and they follow my own kinky desires… I would love to have a femboy to dominate and play with. For me, that would be an important part of any relationship. I’m kinky that way.  But I could only do that if I knew that the femboy wanted me to, and was excited by it. The things I’d do to him would be a mutually-agreed upon, within the parameters of our relationship.  Actual rape or coercion are not sexy at all, and are, in fact, criminal. You should never, ever go along with that kind of action if it isn’t your thing.

You should keep looking for a partner who feels as you do. I’m absolutely certain that you aren’t the only one! Good luck in your search!

-ShadowJack
Reply
#4
 femboy_01_bondage_feminization_by_shadowjack.jpg   
Kevin Goes to the Pride Parade

Kevin was a femboy, of that there was no doubt. But Kevin lived in a small conservative town called Pine Grove, and there was no place for femboys in Pine Grove. He was saving up to get out of this place, to go to college in California somewhere, but in the meantime he had to live with his parents and pretend he was straight.

It wasn’t like he was fooling anyone, other than his parents. Anyone else who heard him speak or watched the way he moved could tell he was gay immediately. Nevertheless, Kevin had to pretend, so he wore blue jeans, white tee-shirts and open plaid flannel shirts like everyone else, and when his co-workers at the supermarket talked about girls, Kevin said the things he was expected to.

Kevin was floored when he heard there was going to be a Gay Pride Parade in Pine Grove. It was scheduled for the same day as the big one that happened in the city, and was billed as a demonstration of the progressive spirit of the new, twenty-first century Pine Grove.

At first Kevin was skeptical. He didn’t know anyone in Pine Grove who was progressive. But he had to admit, he didn’t know all of the seven thousand people who lived there. Maybe he just lived in the wrong part of town. When the local news started hyping the parade and talking about it like it was a real thing, Kevin actually started getting excited about it.

Kevin had never gone outside his room wearing the kind of clothes he wanted to wear. He had never been able to hold his head up and act like himself, never flaunted his gayness. He had never even had a real boyfriend. This Pride Parade was going to be his big chance to finally be who he wanted to be, to join his peers in gay solidarity, to shake off the shame he had always carried.

Kevin had a month and a half to plan his outfit. He agonized over it, spent hours on the internet looking at clothes. Part of him wanted to go full-on femme, but when he really thought about it, Kevin realized that wasn’t actually what he wanted. He didn’t want to be a girl, he just wanted to be a feminine boy. He wallowed in indecision right up until the day of the parade, but finally, he made up his mind.

He wore pointy-toed gray half-boots with two-inch heels on his feet. He wore skin-tight, bright-white yoga pants with a low-cut waist. For a top he wore a white halter-top that had a men’s collar and buttoned in front, but cinched in tight and ended just below his chest and left his arms and midriff bare. He put a shiny brass bracelet on one wrist and a rainbow bracelet on the other. He made up his eyes with mascara, and hung piratical brass earrings from his newly-pierced ears. His hair was the same untrimmed blonde mop it always was.

He fretted because his panties made visible lines through the thin, tight fabric of the yoga pants, and when he experimented he found that he had visible panty lines no matter what underwear he wore. Finally he tried wearing no underwear at all, and he liked the result. His junk was a very visible bulge, but the yoga pants were opaque, and it wasn’t like he was trying to hide his maleness. Quite the opposite, in fact. On reflection, he felt having a visible bulge made a statement.

On the big day, Kevin sneaked out of the house without his parents seeing him, and drove his beat-up baby-blue bug down to the parade. He parked blocks away, hid his keys in the box stuck to the inside of the fender, and walked up to Main Street just as the first float was going by.

He was as excited as he’d ever been, but now that he was out here on Main Street wearing his femboy clothes, fear began to set in. Perhaps this was a horrible mistake, outing himself like this. He looked around, and noticed that there were people in the crowd that he recognized. What’s more, they had recognized him, and he caught some of them giving him the side-eye. Well, it was too late to worry about that now! Kevin was out, and he was proud! Not as proud as he was frightened, but proud nonetheless.

The parade was somewhat less than spectacular. Being the town’s first attempt at mustering a Pride Parade, it didn’t have the polish or the size that more established parades had. But it was an effort, and the crowd clapped reservedly at each entry. Kevin clapped along with them, perhaps a bit more enthusiastically than most.

After the parade had gone by, the crowds of spectators began to thin, while at the same time the barricaded street filled with revelers. Many were obviously gay, like the leathermen, while others were less obvious. At first Kevin thought these were all his people, the hidden gay population of Pine Grove. But the more he looked, the more he realized they couldn’t all be Pine Grovers. Nobody could live in Pine Grove with those haircuts, those piercings and those tattoos. Most of them, he realized, must be from out of town, here to kick off the parade and encourage the local gay population to come out of hiding.

In just ten minutes, the central two blocks of downtown had been transformed from a parade route to a gay street fair, a thing Kevin had never imagined could happen in his tight-assed little town. Street vendors sold rainbow necklaces, tee-shirts and beer in plastic cups. Musicians played on street corners, and gay men openly hugged and kissed each other. Kevin joined the crowd, grinning and greeting everyone he met. This was what he’d hardly dared to hope for, a chance to meet other gay folks.

The first time Kevin saw a leatherman leading his slaveboy down the street on a leash, he felt a strange thrill shoot through him. He stared, astonished. He’d never seen anything like it in real life before. He’d seen pictures on the internet, but had always thought it was just porn, not real. He found himself following the pair, and before he knew it, he was among the leathermen.

“Fascinating, isn’t it?” said a voice from beside him.

“What?” said Kevin, as if snapping out of a trance. He turned to see who had spoken.

The man was tall and well-muscled, his black leather vest open to reveal a thick, hairy chest. He appeared to be in his forties, a touch of gray at his temples, with warm, friendly brown eyes and a sincere smile.

“Didn’t mean to startle you,” he said. “I couldn’t help noticing you watching Al and his slaveboy.”

Kevin felt the heat in his cheeks as he blushed. He looked away, embarrassed.

“Nothing to be embarrassed about,” said the man. “They’re doing their thing in public, they want people to watch them.” The man turned to look at Al and his slaveboy. “Al has absolute power over his slave. At any moment he can order him to suck his cock, and the slave has to obey.”

As if the man’s words were a premonition, the slaveboy abruptly dropped to his knees, his hands clasping behind him. His master unzipped his leather pants and pulled out a thick, heavy-looking cock. He stepped up to the slaveboy, straddling his knees, and inserted it into the slaveboy’s mouth.

“Well sonofabitch, there they go now,” the man chuckled.

Kevin’s mouth dropped open, eyes wide in shock. They were out in the open, in the middle of the street! He looked around nervously. There were no police in sight, and the crowds of Pine Grove residents who had come for the parade had all left. There was no one around now but the gay guys in the street, and they were stopping to watch the scene unfold, obvious approval on their faces.

Kevin had never imagined something like that could happen right there on Main Street. But shocked as he was, it was the implications of what he was seeing that affected him the most strongly. The man had just been saying that the slaveboy had to obey any time his master demanded satisfaction, and now he was seeing that happening. In his mind, Kevin was imagining what it would be like to be that slaveboy, to have to take his master’s cock whenever and wherever his master felt like it. It made him feel all soft and gooey inside.

“You must be a local boy,” said the man beside him. “I love your outfit. My name’s Francis, by the way.” He held out his hand.

“I’m Kevin,” said Kevin, shaking the man’s hand. Francis’ grip was firm and strong, and held him a little longer than was comfortable.

“Care for a beer, Kevin?” Francis held up the can of beer in his hand.

“Sure,” said Kevin.

The leathermen had an outreach trailer right there in the street, displaying rows of pamphlets and informational packets, and a sign that identified them as visitors from out of town, as Kevin had suspected. But inside, the trailer also held coolers of beer and who knew what else.

Francis pulled one out of the ice, popped the top, and handed it to Kevin. Kevin drank gratefully, his eyes returning once more to the slaveboy avidly sucking his master’s cock just twenty feet away.

“Dominance and submission,” said Francis. “That’s what we’re all about. Some of us have the instinctive need to dominate, and some have a need to submit, sexually. The two fit together, and both get what they need. Like Yin and Yang.”

“I’ve never done anything like that,” said Kevin wistfully.

“But you’ve imagined it, haven’t you?” Francis said softly into his ear.

“Yes…” said Kevin, shocking himself. He’d never admitted that to anyone! He felt himself blushing again.

Slowly and deliberately, Francis reached his free hand over to cup the bulge in Kevin’s yoga pants. Kevin’s breath caught in his throat as he watched the hand coming, hardly believing it was happening. Despite knowing it was going to touch him, he couldn’t help gasping as it closed gently around his balls.

Oh my god, he’s touching me!

It felt so good, and it had been so long since anyone had touched him there! The fabric of his yoga pants was so thin he could feel the heat of Francis’ hand, the tiniest subtlety of his caress.

“You’re submissive, I can tell,” murmured Francis as he skillfully stroked Kevin’s cotton-sheathed cock and balls. “In your fantasies you’ve served stronger men with your body, and let them use you for their own pleasure… haven’t you, Kevin?”

“Yes,” Kevin whispered, shivering and closing his eyes.

He felt his cock stiffening under Francis’ ministrations. There was an alarm going off in his head, telling him he shouldn’t be letting a stranger do this to him out here on the street in front of everybody, but god, it felt so good, and he’d yearned for someone to touch him like this for so, so long… Soon he was rock-hard, and Francis just kept rubbing and caressing him, stoking his libido until he couldn’t even think.

“I’m going to put this collar on you now, Kevin,” said Francis.

“What?” Kevin opened his eyes, and Francis was holding a black leather collar with glittering silvery hardware in front of his face. Where had he gotten that? His other hand had never stopped stroking Kevin’s stiff cock.

“It means that you’re my slaveboy, Kevin. It means you have to do whatever I say. But since you’re new to this, you can choose not to be a slave at any time, and I’ll take it off. Okay?”

Kevin was speechless, but the collar went around his neck all the same. This was happening way too fast, but he was so excited now that he didn’t want to resist. He had fantasized being an older man’s slave thousands of times, and suddenly it was really happening!

A leash was snapped onto the front of the collar. Francis relieved him of his half-finished beer, then his strong hands were pulling Kevin’s wrists behind his back, and handcuffs were being fitted around them. Kevin let it happen, his desire overpowering his caution, his head full of fantasies.

Then Francis was leading him around by his leash, pulling him first one way, then another, and Kevin was helpless, concentrating all his effort on staying upright. His master finally stopped him behind the outreach trailer.

“Down on your knees, Kevin,” he commanded, and Kevin dropped to his knees without hesitation.

Kevin licked his lips in anticipation as Francis unzipped his tight leather pants inches from his face. The cock he pulled out was so thick Kevin could hardly believe it. He opened his mouth as wide as he could, and Francis stuffed the fat, meaty appendage inside.

It didn’t go well. No matter how wide Kevin opened his mouth, that cock barely fit into it. His teeth scraped the top and bottom, and deep in the back of his mouth the massive cockhead was rubbing against his back teeth on both sides. As the cock stiffened and swelled, things only got worse. It didn’t take long for Francis to realize this wasn’t going to work. He withdrew, and tucked the monster back into its den.

“Up!” said Francis, yanking the leash. Kevin rose quickly to his feet, his brain trying to frame an apology of some kind. “Okay,” said Francis, “you’re not going to be a suck-slave. Ain’t got the mouth for it.” Kevin felt a big, warm hand caress his right bottom-cheek. “No, Kevin, you’re going to be a butt-slave.”

He led Kevin to the back end of the trailer, and opened up the cabinet doors there. Inside, there were shelves, deep enough to hold the large sandwich-board signs they had distributed around their area. Francis put a hand on Kevin’s head and bent him over, guided his head into a low, empty shelf. He pushed him inside, all the way in, until only Kevin’s ass was sticking out of the trailer. It was just the right height that his feet were firmly on the pavement, and he was bent over at a hard right angle, his entire upper body wedged into a narrow alcove that smelled of plywood.

Kevin was starting to tremble. He knew what Francis had in mind, and it frightened him. He had played with other boys in high school, and on a couple of occasions he and another boy had tried butt-sex. It had been awkward and difficult, their inexperience making a hash of it, and Kevin’s memories of those experimental penetrations were unpleasant. Now suddenly he was bent over and helpless, and he knew Francis intended to stuff that monster cock of his into his tight little hole!

He knew if he started yelling Francis would let him go, at least he thought he would, but he’d fantasized about being another man’s slaveboy for so long, the last thing he wanted was to chicken out and end it. So Kevin kept still, closing his eyes and bracing himself for the ordeal he knew was coming.

Francis’ hands caressed his lean, rounded ass-cheeks lecherously through the thin white fabric of his yoga pants. His thumbs delved into the crevice between, spreading it, pressing the cloth tight against its deepest features. Kevin could feel the questing thumbs seeking and finding the puckered dimple of his anus. Then fingers pinched the fabric in exactly that spot and pulled it out, pulled it far out. There was a snipping sound, the sound that only scissors make, and then the stretchy cloth snapped back into place.

Kevin’s eyes widened in sudden shock. He could feel a cool draft of air right on his anus and nowhere else. Francis must have cut a hole in his yoga pants, right where his anus was! His suspicion was confirmed a moment later when he felt a finger touch the sensitive puckered flesh, skin-to-skin. Kevin yelped and squirmed, but he was entirely helpless as Francis tickled and teased his nervous asshole with his fingers. Before long the fingers were smearing a thick lubricant onto the clenching orifice, and a few moments after that they began forcing their way up inside.

He’s going inside my butt! His finger is sliding in…

Inside his little plywood enclosure, Kevin yelped and whimpered as strong, skillful fingers explored his nervous rectum. Every noise he made was amplified in his own ears, and he was embarrassed at how pathetic he sounded. Francis was experienced and careful, but he was relentless, and while he never caused Kevin any true pain, he kept on pushing the boundaries of his tolerance, stretching the tiny, frightened orifice wider and wider. Finally the fingers withdrew, and Kevin felt the thick, spongey head of Francis’ monster cock pressing against his anus.

Oh god, oh god, he’s going to fuck my bottom!

Kevin had only taken a cock in his ass twice, but he had never given up control to his little friend in high school. This was entirely different. Kevin had no control at all here, and on top of that, Francis’ cock was more than three times the size of his high school friend’s little dick!

God, it’s going in!

Kevin began to panic. He tried to twist away, to switch his ass from side to side, to somehow evade the inevitable. He managed to dislodge the invader twice, but then Francis gripped his hips tightly, holding him still while he pushed. Kevin’s terrified ass clenched spasmodically, but the massive cock was inexorable. The tiny hole stretched around the immense cockhead, and suddenly it was inside.

Kevin squealed, the sound almost deafening to his own ears, but barely audible outside. The pain was intense, and Francis paused there, only the head of his cock inside the femboy, and waited until the squealing stopped. Gradually the pain subsided, Kevin’s tortured anus adjusting to the intrusion. When the squealing petered out into a soft, breathless whimpering, Francis resumed his invasion, and the giant cock forced its way deeper into Kevin’s ass.

Despite a series of pitiful wailings, groans and yelps from inside the plywood alcove, Francis drove his cock all the way into the femboy’s hot, tight ass. Finally, buried to the hilt, he sighed and waited, enjoying the involuntary spasms that squeezed his cock for several minutes.

His cock is inside me! The whole thing! It must be pressing against my lungs, I can hardly breathe!

Kevin gasped for air like a fish out of water, making desperate whimpering noises. So many times he’d fantasized what it might be like to take a man’s cock in his ass, but he’d never imagined what he felt now. His emotions roiled as his body tried to adjust to its impalement. It was agony, the massive cock buried so deep in his entrails he feared he might die. He felt the muscles of his anus still trying to close, their involuntary constriction only making the pain worse. Kevin felt tears stinging his eyes, his body shuddering violently. Gradually, the spasms subsided, easing his pain, but no sooner had he reached a point where it was tolerable, than the monster cock inside him began to slowly slide in and out with long, deep strokes.

Oh my god, he’s fucking me! I’m being fucked!

Francis loved these repressed, small-town femboys. He knew exactly what they needed, far better than they themselves ever did, and he made a party out of giving it to them. He knew their yearning for submission, and he could tell this one, like most of them, had never experienced real submission before. By putting them in a position where they had no recourse but to submit, he could break through the barriers of their inhibitions and bring them their first experience of being truly dominated. The result was nearly always spectacular.

Francis fucked the femboy’s tight, inexperienced ass like it was his own, personal fuck-toy. He fucked it slow and deep, fast and hard, any way he pleased. Sometimes he popped his cock out of the hole entirely, just so he could slowly force it back inside. The desperate noises and protests that issued from the plywood enclosure were so muffled that only he could hear them, and to him they were sweet, sweet music that only fed his libido. The cabinet doors hung open, blocking the view of any casual passerby, and he knew he could take as long as he wanted.

Francis fucked Kevin for a full forty-five minutes. After the first twenty, the femboy’s cries had lost their urgency, and the begging and protests had stopped. The groans and whimpers he listened to toward the end were the sounds of a submissive femboy deep in the throes of his submission, a real, honest slaveboy giving in for the first time to the domination of his master’s cock. When Francis finally allowed himself to cum, his hot flood of semen filling the femboy’s well-stretched rectum, he let out a cry of triumph.

When Kevin was finally pulled forth from the cabinet and allowed to straighten up, he was barely coherent. His bright red cheeks were streaked with mascara from the tears he’d cried while being fucked, and his glassy eyes were wide with awe. He voluntarily dropped to his knees and gazed up at Francis as though he were a god, and Francis smiled, basking in the moment. There was nothing quite like introducing a repressed, inexperienced femboy to the joy of submission!

Kevin’s new master tugged on his leash, signaling him to rise to his feet, and he obeyed quickly, though he was a bit unsteady. The world around him seemed unreal, the only reality his master’s desires… and his own.

“C’mon, Butt-boy, we’re going for a little walk,” Francis said gruffly, yanking Kevin’s leash for emphasis.

Francis led Kevin down the street, pulling him along by his leash just as Kevin had seen that other slave being led. Even through the warm haze of his desire, Kevin was aware of where he was and how he must look, being led like a dog down the street, his wrists cuffed behind him. He was acutely aware of the fact that he was in the middle of Main Street, in the ultraconservative town of Pine Grove, and that there were bound to be locals nearby who could see him. He felt his cheeks burn as he blushed, and he lowered his eyes for fear of seeing someone he knew.

But with his eyes lowered, he suddenly discovered something he hadn’t realized before now; his cock was erect, and it was pushing out very visibly against the thin fabric of his white yoga pants. Worse, the white fabric had been soaked with pre-cum, and had become translucent all the way down to the base of his cock. Everyone they passed could see his rock-hard erection, plain as day! It was glaringly obvious the way it stood out from his abdomen, and every feature was clearly visible to everyone they passed. And with his hands cuffed behind him, there was no way he could hide it!

A minute ago Kevin had been glowing with the first flush of true submission. Now he was burning with humiliation. It was more than he could bear, and yet somehow his penis remained hard. Nearly everyone they passed stopped to stare, many of them pointing at his stiff dick and laughing, but Francis seemed oblivious as he led him down the block. One guy, a member of a large group of local men and women, did a spit-take when he saw Kevin, and the whole group erupted in uproarious laughter. Francis led him on a winding course the entire length of the enclosure, finally approaching another cluster of black-clad leathermen, another chapter from out of town. It was the longest walk Kevin had ever taken.

Abruptly, Francis stopped to greet a friend, a fellow leatherman. No longer being dragged forward, Kevin turned away from the crowds, trying to hide his embarrassment. That didn’t last long. After less than a minute, Francis was showing off his enslaved femboy to his friend, turning him to face the man and yanking upward on his leash to make him straighten up. The friend, a muscular, dark-haired man with a pointed goatee, grinned and stroked Kevin’s hard cock familiarly through the wet, translucent fabric that covered it, as though he were petting a cat.

He commented that Kevin was a very nice-looking femboy, and just like that, Francis asked his friend if he’d like to fuck him. Ignoring Kevin’s shocked reaction, the friend, whose name was Kirk, said he would. Next thing Kevin knew, he was being dragged into a cluster of leather-clad men. They all seemed to know Francis, and were obliging enough to arrange themselves very close together, forming a tight circle and blocking the view of passersby with their bodies. Meanwhile, Francis made Kevin bend over so that Kirk could fuck him.

Kevin felt his panic rising as rough fingers inserted themselves through the convenient hole in his leggings, probing the well-lubricated orifice inside. Despite the thorough buggering Francis had given him, his ass felt as tight as ever. After a very brief probing, Kirk brought out an impressive cock and began stuffing it into Kevin’s shuddering, reluctant ass.

It went in far easier than Kevin thought it would, but the initial pain of it made him wail loudly. There was a ripple of laughter from the leathermen, and one of them covered Kevin’s mouth to keep the noise from attracting attention. Two others held him still while Kirk began fucking him.

The sensation of another thick, meaty cock plunging in and out of his rectum soon put Kevin back into the submissive state he’d been in before. It still hurt, but the pain was mitigated by a growing strain of pleasure and overshadowed by his desire to be desired, to be used by stronger men.

When Kirk was done with him, another man stepped up behind him. Another cock drove its way into him, then began sawing in and out. By now Kevin was only whimpering and grunting softly as he was fucked, so the hand was removed from his mouth. The stranger fucked him for a long time, but eventually he fired his load and withdrew. There was another man waiting to take his place, then another and another. At some point Francis slipped away to find a restroom, and never came back.

All in all, eleven men took their pleasure inside Kevin’s tight little bottom-hole. When there were no more takers, a short, burly guy he’d never seen before cheerfully took his leash and led him away.

Kevin was beyond questioning anyone at this point. Apparently, this guy was now his master. In his mind he was nothing but a slaveboy, an ass that belonged to anyone with a hard cock. He was lost in the rapture of his submission, and didn’t want to have to think. He was still aware of how visible his hard cock was in the pre-cum-soaked yoga pants, but now it was dusk, and the people they passed were shadowed, without detail. He hoped he looked the same to them.

His new master stopped him at a kiosk that was selling arcane-looking gay sex aids. He barely got a glimpse of the oddly-shaped butt-plugs and shiny cock-rings before his burly master bent him over the counter. A moment later he felt a cock forcing its way into his ass through the hole in his pants, and then he was being fucked, right there, out in the open. He tried to keep as quiet as he could, but toward the end he was really being pounded, and he couldn’t keep from wailing.

When his master was finished, Kevin found himself being passed off to another man, who took his leash and led him a little ways down the street until he met someone he knew. Soon Kevin felt fingers slipping into his well-used bottom-hole, and then he was being bent over and sodomized again, right there in the street.

This is what it’s like to be a slaveboy. Anyone can use my bottom-hole, any time, anywhere.

Another load of semen was pumped into Kevin’s ass, then he was turned around and another guy stuck his cock into him. He pounded him mercilessly, then finally came with a loud groan, which was followed by a round of applause. When Kevin straightened up, someone new had ahold of his leash, but Kevin didn’t question it. Soon this guy, too, was fucking him, and when he was finished there was someone else.

Kevin lost track of how many times he was used. He was so deep in a state of submission it hardly mattered any more. Things changed when he noticed that the guy who was leading him now seemed very young. He was skinny, a little gawky, and reminded Kevin of his high school days. The young guy led him down the block, texting on his smartphone. When they got to American Burger, he led Kevin inside, and headed straight for the men’s restroom. There were a lot of guys using the restroom, so the young guy took Kevin into one of the toilet stalls, the big one that was designed to accommodate a wheelchair.

In the light of the restroom, Kevin could see that his new master was even younger than he’d thought, much younger than he was, probably still in high school. He was a little taller than Kevin, but then nearly everyone was. The kid looked him up and down, grinning. “You’re a cute little femboy,” he said. “We’re gonna have fun fucking you.”

He bent down and removed Kevin’s boots, having him lift his feet one at a time. When he was barefoot, the kid ordered him to get up and stand on the toilet seat, then turn around and face the wall. Kevin obeyed him without question. Then he made him squat down, making his ass stick out and spreading his cheeks wide. A moment later he felt the kid’s fingers touching his tender anus through the hole in his yoga pants. He shivered, bracing himself for what he knew came next. The fingers slipped up inside him, and Kevin discovered his ass was sore from all the fucking. He only whimpered softly, and rested his head against the wall to brace himself, his hands tugging futilely against the handcuffs. After a few moments the fingers withdrew, and then he felt the blunt head of a cock against his hole.

The kid entered him slowly, letting him get used to being stretched again. But once he had his whole cock inside, he began pumping away, making Kevin gasp and groan. “Fuuuuuuck,” said the kid softly, “I can’t believe you’re so tight after that gang-bang!”

Kevin tried to make sense of the words, his thoughts scattered. Had he been gang-banged? He had been fucked by a lot of men, but not all at once. Still, now that he thought about it, if you added them all together, it probably did count as a gang-bang. Then his ability to think slipped away, his attention focused on the cock plunging in and out of his ass.

The fucking had been going on for several minutes when there was a discrete knock on the stall door. The kid yanked his cock out of Kevin abruptly, and turned to open the door. Four more high school kids slipped into the stall, giggling nervously. A couple of them looked even younger than the kid who’d brought Kevin here. The kid shushed them, locked the door, and turned back to Kevin’s butt. “I’m first,” he said. “I’ll be done in a few minutes.”

The kids gathered around, uncomfortably close, as the first one stuck his slick cock back into Kevin’s ass. Hands grasped his shoulders, steadying him and moving him away from the wall so that he didn’t need to lean his head on it to keep his balance. The fucking resumed, the other kids whispering and brushing Kevin’s hair from his face so they could watch him as he took cock. They cooed and giggled, and he heard several times how cute they thought he was. They were all high school age gay boys, but Kevin noted that none of them was as femmy as he was. They probably passed for straight here in Pine Grove.

After the first kid came inside Kevin’s ass, another one stepped up and began fucking him. Kevin felt weird about being dominated and used by high school kids, but when he had a cock inside him his thoughts scattered. He was only two years out of high school himself, so they weren’t that much younger than he was anyway, and he was certainly no more experienced than they were.

The second boy was soon squirting inside him, and when the cock pulled out of him Kevin just waited for the next cock. But the other kids were holding an intense whispered conversation, and nobody was stepping in behind him.

“He’s not from out of town,” one kid was saying. “I recognize him, he works at the grocery store.”

“Okay,” said another, “then let’s ask him.”

The kids helped Kevin down off the toilet, letting him sit down on it instead. When they each told him their names, just like he was a real person, Kevin had to slip out of his submissive trance and re-engage his brain. He told them his name was Kevin, and soon they were having a normal conversation, talking about high school and how hard it was being gay in a town like Pine Grove. They were friendly and open, and Kevin liked them. When they asked him if he’d like to come with them to their clubhouse, he agreed, especially after they mentioned they had a handcuff key there.

The kids had formed a secret gay club of about a dozen boys, and their clubhouse was a small guest-house in the back yard of an elderly, secretly gay man who had taken pity on them and let them rent the place for half the going rate. Since they all still lived with their parents, they were rarely all there at once, so it wasn’t crowded despite its small size. The bondage equipment prominently displayed in the main room was an easy giveaway as to their predilections. Within half an hour of Kevin’s arrival, they had him naked, blindfolded and helplessly chained, standing on the low coffee table in the center of the room, hands cuffed over his head.

This was a game Kevin had never played before, but he knew the rules. He was theirs to do with as they pleased, and he had a safeword if he needed it. At first they explored his lean, smooth-shaven body with curious fingers, admiring his feminine attributes as no one ever had before. But soon they were paddling his bottom with an assortment of implements, delighting in the way he squealed in pain just like a girl. Next they toyed with his cock and balls, tying them up and teasing them, oiling his hard shaft and stroking it until Kevin was panting with unrequited arousal, almost begging them to let him cum.

They were inexperienced, exploring their own desires even as they explored his body. They fumbled a lot, and some of them touched and stroked him like they had never handled another person before. Nevertheless, Kevin was entirely at their mercy, his helpless body theirs to play with. For all their inexperience, again and again they stroked him almost to orgasm, only to deny him every time.

Finally, after an hour of teasing torments, they laid him down on the table, tied him with his legs folded against his chest, and took turns fucking him. Only after they had all cum inside his hot, squishy rectum did one of them finally stroke his desperate cock until he came, squealing helplessly, shooting streamer after streamer of hot semen into his own open mouth.

When it was all over they asked Kevin if he would join their club and let them play with him regularly. Without hesitation, Kevin agreed to be their unconditional slaveboy. They may have been young, but Kevin had finally found his masters. Twelve of them.
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#5
 femboy_02_bondage_feminization_by_shadowjack.jpg   

Femboy in the Woodshed

Every time the heavy leather belt struck his naked ass-cheeks, Danny yelped and jerked helplessly, involuntarily thrusting his hips violently forward. Directly in front of him, at about mid-thigh level, there was an electric fan, the blades of which had been replaced by six-inch pieces of leather bootlace. The laces whirled so fast they were invisible, but every time the belt drove Danny’s hips forward, his hard cock was thrust into them, whipping and stinging the tender flesh. He’d yelp or squeal in pain and pull his tortured penis back out of the spinning laces as quickly as he could, which only thrust his ass out behind him, offering a perfect target for the next stroke of the belt.

Caught between the brutal blows of the belt and the stinging lashes of the bootlaces, Danny helplessly thrust his hips forward and back, forward and back, forward and back, yelping and wailing desperately the whole time. Tears ran down his cheeks, the stinging, maddening pain driving him into a frenzy, yet he couldn’t stop the thrusting of his hips. And his cock, seemingly with a mind of its own, remained throbbingly hard as the torture continued.

Danny was only dimly aware of the imposing figure of Jake, standing in front of him, sipping on a beer and smiling in amusement as he watched. Last round it had been Zeke standing there watching, while Jake had wielded the belt. The two of them were taking turns swinging the heavy, doubled-over belt back and forth, strapping his ass from the right, then the left, then the right again, beating him in a steady, metronome-like rhythm.

Danny shrieked and squealed as only an effeminate femboy could, his cries loud inside the small, crude woodshed. But they were miles from anywhere, the shed, and Jake and Zeke’s house, surrounded by nothing but woods, and no one could hear his suffering but Jake and Zeke. They loved making Danny scream. The more he wailed and cried, the better they liked it.

They had been keeping this particular punishment going for forty minutes, by the clock on the wall, which was the longest they’d ever done it before. But they’d been punishing Danny all afternoon. They’d done all their favorite tortures today, starting right away when he’d shown up at noon.

First they’d stripped him down to his stockings, throwing his femmy girl-clothes contemptuously onto the floor. They’d slapped his erection repeatedly, sneering with derision and ridiculing him for being so excited. They’d bent him over and thrust their lubed fingers into his tight little asshole again and again, trying to make him admit that he liked it, even though they knew he could never say it out loud. They’d forced a big, smooth butt-plug into him, and left it there while they tied his hands and put on his collar. Then they’d taken him for a “walk,” dragging him on a leash through all the brush and brambles they could find. Returning to the woodshed, they’d tied him securely to a rack they’d made for the purpose, using yards and yards of rope, his legs well-spread.

Maintaining their usual attitude of contempt for Danny and his feminine ways, they’d settled in for some intimate, sexual punishments. They’d tormented his helpless cock and balls for over an hour, casually drinking beer and laughing every time they got a shriek out of the femboy. They’d used ice cubes until his penis had begun to shrink, then tied it up tight with twine and teased it back up to a painful hardness. They’d slid long, slender model-paint-brush handles into his defenseless pee-hole, going so deep that the brushes nearly disappeared, then yanking them out and laughing at the way the pre-cum oozed from the hole in greater quantity each time. They’d held a toilet-brush, the kind with a ring-shaped wire full of sharp, stiff white bristles, against the tip of his cock, then thrust a rubber dildo into his ass harder and harder until he pushed his own cock in and out of the painful ring of bristles. They’d slapped and tickled and teased his cock endlessly, keeping it always at various stages of hardness, keeping Danny always aroused and then ridiculing him for it.

These little torments had gone on and on, punishments that were intended to humiliate Danny and draw agonized squeals of pain from him, yet never leave any lasting damage. It was only after they were no longer getting sufficiently satisfying cries from the captive femboy that Jake and Zeke had progressed to their current activity, using the belt and the fan with the leather laces, their favorite torture.

At last the beating stopped, Zeke panting with exertion behind Danny. Jake turned off the fan and moved it aside. Danny was left panting and whimpering, his ass-cheeks burning like fire, his cock stinging from the laces, but still hard nevertheless. Jake fetched fresh beers for himself and Zeke, then plopped into a chair next to Danny.

“Look at you, ya fuckin’ faggy-ass girly-boy,” he said with the usual contempt. “Still hard after all that. Yer cock still beggin’ for attention. I can’t believe how pathetic you are.”

Danny looked down at his poor, tortured erection, the tender skin covered with bright pink marks from the spinning leather laces. For the thousandth time, Danny asked himself why, why, why did he keep coming back here? Why did he need this?

Every Saturday afternoon he found himself at Jake and Zeke’s woodshed, and every time he came, they did things like this to him. First they’d make contemptuous, insulting remarks about his feminine clothing and his effeminate mannerisms. Then they’d pull him into the shed and strip off his clothes, leaving him naked and vulnerable between them. They’d ridicule him for having a hard-on from being forcibly stripped, and then they’d make him even harder by slapping his bare butt or yanking him around by his dick. Finally they’d tie him up with rope, and he’d spend the rest of the afternoon tied up, helpless, being subjected to any sort of indignity they cared to perpetrate on him.

They were mean, hateful men. They didn’t care about him, they just liked humiliating and torturing him because he was a femboy. They thought he was some unnatural, pathetic pervert, a mere parody of a man. They’d abuse him for hours, indulging whatever sadistic whim struck their fancy, and after they’d had their fun with him, they’d bend him over and fuck him brutally with their huge cocks before they finally let him go.

That part was always a constant; no matter what else they did to him, they always fucked him at the end. They always did it as roughly and painfully as they could, too, using their cocks as weapons. They pretended the only reason they were fucking him was to punish him for not being a proper man, for being a skinny, whiny, girlish femboy.

And Danny kept coming back for more. He couldn’t have explained it, but after being abused and raped that first Saturday, he found himself there again a week later, dressed even more girly than the week before. After that, Jake and Zeke had known his darkest secret, the secret he hadn’t even been able to admit to himself: the fact that he craved their abuse. Somehow, deep down in his psyche, Danny needed to be treated the way they treated him. They never let him forget it, either, and reminded him constantly while they tormented him.

Inversely, Danny knew their secret, too: They loved using and abusing him. They pretended the brutal fucking at the end was just their way of punishing him for being what he was, but after spending the afternoon playing with him and humiliating him, they were both so hard and horny that they needed to pound his femboy ass as badly as he needed the pounding. But Danny would never mention this. It might ruin everything.

Finally, Jake reached out with a handful of lube, and began to stroke Danny’s drooping cock. After being teased and tormented all afternoon, Danny couldn’t help responding. Jake’s hand sliding along his tortured shaft like that was heaven! He groaned and thrust his hips forward, offering himself to Jake’s mercy, or lack thereof. Jake chuckled derisively, but he kept stroking Danny’s poor, tortured cock, and it throbbed and swelled in response. In less than a minute, it was fully hard and pulsing, nearly quivering with excitement. Danny could feel the beginnings of an orgasm starting to build, and he allowed himself to hope that, maybe this time, they would actually let him cum! He was getting so close…

But then Jake stopped stroking him, and laughed at the femboy’s pathetic whimper of disappointment. Danny’s hips continued to thrust futilely at the air for several more seconds before he could regain control. Jake was so amused by this that he started stroking him again after a minute. In spite of himself, Danny shuddered in grateful pleasure, and his hips started humping again. Jake took him even closer to cumming this time, but stopped well before he’d reached the point of no return. This was a game he’d played often with Danny, teasing him and then denying him, and he had gotten good at it.

Jake chuckled, shaking his head in disgust. He took another pull from his beer. “You are so fucking pathetic,” he growled. “Maybe I should call ol’ Demon in here again, and let ‘im have another go at you.”

Two weeks before, Jake and Zeke had slathered Danny’s cock and balls with butter, and then brought in Demon, their slobbery pit-bull mix mongrel. The dog had gone to town, enthusiastically licking every inch of Danny’s buttery genitals, until it had slurped up even the faintest vestige of flavor. It had been both humiliating and terrifying for Danny, and he’d begged and yelped and jerked around wildly as the dog licked away at his helpless cock and balls. Nevertheless, his cock had responded to the relentless slurping. It was one of the few times he’d actually been allowed to cum, and Jake and Zeke had laughed uproariously at him for a long time.

Again Jake reached out and stroked Danny’s desperate cock. And again he stopped before Danny could cum. It took the femboy even longer to regain control this time. Behind him, Danny could hear the jingle of a buckle, the zip of a zipper. He began to tremble.

“Ol’ Demon sure did like you,” said Jake, reaching over to stroke Danny’s helpless erection once more. “We should let ‘im get to know you better. Maybe we should let ‘im fuck you next time. You’d like that, wouldn’t you, you girly bitch?”

Again Jake stopped just short of letting Danny cum. The femboy’s trembling increased as he heard Zeke’s boots step up onto the platform behind him. Part of him wanted to turn and look, to catch a glimpse of Zeke’s massive cock before it plowed into him, but another part didn’t want to look at it. The sheer size of the thing was too frightening.

Zeke’s big hands wrapped around Danny’s slim hips and yanked him backwards, forcing him to thrust his ass out as far behind him as his ropes would allow. His cock quivered and bounced, hard and ready, but now forgotten as Jake sat back to watch Zeke fuck the little blonde femboy. Holding his breath, his eyes clenched shut now, Danny felt the big blunt head of Zeke’s cock bump against his ass, clumsily homing in on the tiny pink pucker of his anus. Zeke used his hand to guide the rock-hard bludgeon, zeroing in on the little dimple, and when he had it, he began to push. Hard.

Danny screamed as the immense cock surged up into his body. As always, Zeke drove it all the way home on the first thrust, maximizing the pain he knew his cock caused. Once he was buried to the hilt in Danny’s ass, he paused, enjoying the way the femboy’s agonized spasms squeezed his cock. Panting, basking in the tight, moist heat and letting the spasmodic clenching milk his brutally thick shaft, he waited until the spasms subsided.

“This is what you get, you disgusting little girly-boy,” he growled. “I’m gonna fuck you so hard your dick is gonna pop off.”

With that, he proceeded to fuck Danny. Just as he’d promised, he fucked the femboy as hard as he could, each stroke slamming home deep in his guts, his strong hands pulling Danny’s hips into the thrust. Danny wailed and cried in real pain, but deep inside him, his churning emotions embraced the agony, and his femboy body began to work its magic, gradually turning some of the pain into pleasure. He was mindless now, incapable of thought, but his submissive instincts were taking over, and the pounding of Zeke’s cock deep inside him gave him what he’d been needing.

Danny’s desperate cries began to change slightly, becoming less sharp and longer, but no less primal. His voice warbled with each jolting thrust, and though the tears continued to roll down his cheeks, Danny was no longer suffering.

Zeke pounded his pert, round ass long and hard, slamming into him with all his strength, believing that he was punishing him for being such a disgusting sissy. The loud slapping of skin on skin a steady percussion to the long, warbling cries issuing steadily from the abused femboy. Zeke chimed in at the end with his own deep groans of pleasure as his hot semen flooded Danny’s slick bowels.

Then it was Jake’s turn. Jake’s cock, once it was fully hard, was nearly as big as Zeke’s. Once it was inside him, it felt every bit as big to Danny, and he squealed uncontrollably as it charged into his rectum. After the first salvo of slamming thrusts, Jake changed his angle, stepping forward and straightening the helpless femboy’s body more toward the vertical. Now each thrust started low and drove upward, the power of each stroke lifting Danny off his feet. Jake was trying to make the fucking hurt more, to maintain the quality of screams that he liked, to make sure that Danny was being properly punished. But while the femboy’s cries became louder and deeper, he was beyond pain.

Jake hammered away, tossing the femboy’s slender body around, but the more brutal he became, the more it aroused Danny. Finally Jake began pounding down the home stretch, his orgasm only moments away, and that was when Danny came. Untouched, his tortured cock began to pulse wildly, and then jets of white, creamy semen shot into the air. Danny squealed helplessly as he came, but Jake didn’t even notice as he, too began to cum, roaring out his pleasure like a lion.

Afterward, the men untied Danny. As always, they didn’t want to look at him after they’d come in his ass, and they said little as they left the shed and headed for the house. The femboy sat for a few minutes, recovering. Finally he rose shakily to his feet, and started looking around for his clothes. Alone in the woodshed, naked, streaked, welted, well-used and filled with semen, Danny smiled.
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#6
Femboy Carry-Pack

 femboy_03_bondage_feminization_carry-pack_by_shadowjack.jpg   
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#7
 femboy_04_bondage_feminization_by_shadowjack.jpg   

Rape Me

Jackie met Ralph in a nightclub just after midnight. He was big and muscular, with huge, powerful-looking hands. He wasn’t good-looking, but he still made her belly flutter. He wasn’t good at conversation, but within a minute of having introduced himself, his hand brazenly lifted her skirt and grabbed a handful of her cock and balls through her panties.

Alarms went off in Jackie’s brain. She almost spilled her drink as she grabbed his wrist with her free hand and tried to push his hand away, but her push was weak, and his hand didn’t budge. A grin spread across his face as he massaged her package. She stared at him with wide, shocked eyes, and as the alarms died away she was left with one powerful, rebellious conviction: This was how she wanted to be treated.

She’d been coming here for over a month, and had navigated the minefield of revealing that she was trans with dozens of guys. There had been five guys who had made that cut, and three of them had endured the negotiations that followed and taken her home. None of them had thrilled her, none had made her feel the way she felt right now, with Ralph squeezing her junk like it was his. And that was when she said it.

“Rape me,” she said.

She didn’t know what would happen. She only knew she wanted this man to take her and use her like she was his property. She had no idea he was going to take her by the shoulder and guide her to a dark corner in the back of the club. She didn’t know he had three friends, big, military guys like him, who would come over to get in on the action. But when Ralph pushed her firmly up against the wall, lifted her tight mini-skirt up around her waist and began to maul her while his friends stood watching, their bulk blocking the view from the rest of the club, Jackie definitely had second thoughts.

Ralph was rough with her. Maybe he understood that was what she needed, or maybe it was the only way he knew. Jackie yelped and gasped and whimpered as he handled her tender balls and quickly-stiffening cock, but the music in the club was more than sufficient to drown out any noise she might make short of a scream.

He stroked her erection brutally, his rough hands lubricated only by spit and her own pre-cum, and when he decided she was aroused enough he pushed her down onto her knees. He pulled out a massive, impossibly thick cock and stuffed its semi-hard mass into her open mouth. Jackie did her best to try to please the cock with her tongue, and as it thickened and extended, Ralph began to fuck her mouth with it. He held her head with his big hands while he tried to force his monster cock down her throat again and again. Jackie gagged and choked, her eyes filling with tears, but the thing was far too big to swallow.

Finally Ralph withdrew his cock and pulled her to her feet. He spun her around and pushed her face-first into the wall. Driven now by his own lust, he yanked her stretched, soggy panties down and took her smooth, lean ass in his hands. One of his friends handed him a tube of lube, and he forced a thick, slippery finger up into Jackie’s tight, nervous hole. She groaned and hugged the wall as Ralph worked his finger around inside her. Then it was two fingers, and then three, each addition drawing agonized groans from her.

Then Ralph lubed up his immense slab of cock and began working it up into Jackie’s ass. It took a few minutes, with Jackie squirming and squealing, but when the giant cock finally slid deep up inside her bowels, all she could do was gasp and shudder, her face pressed against the wall, mascara streaking her cheeks.

Ralph fucked her brutally, and it went on so long that Jackie lost all sense of where she was or what was happening to her. Her world became that massive cock rampaging inside her ass, the noises spilling from her mouth unrestrained by reason. When he finally pumped his load into her and withdrew, one of his friends stepped up behind her, and it started all over again. After him there was another one, and another after that. Jackie lost track, but afterward she remembered being fucked way more times than Ralph had friends. Either they’d all gone back and raped her ass a second and maybe a third time, or other, random guys had started wandering up and fucking her. She didn’t know, she only knew that every time a cock softened and slid out of her, another one went right back in.

It was, by far, the most exciting night of Jackie’s life, the experience all of her future adventures would be measured against. She never met Ralph and his friends again, but for Jackie, the words “rape me” became a magic portal. She learned to use them judiciously, but when the time, situation and partner were right, those words could take her to any number of bizarre, frightening but ultimately blissful nirvanas.
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#8
 femboy_05_bondage_feminization_by_shadowjack.jpg   

Take Me for a Ride

Darian walked slowly down the sidewalk, sipping his soda and enjoying the warm summer evening. He was wearing his sandals with the three-inch heels, and as long as he took his time, his walk was perfect, elegant and precise with just the slightest sway of the hips. He’d been practicing a lot. His plaited skirt was short, but not too short, the tops of his stockings still hidden by its hem. His top was tight, and it ended just four inches from the top of the skirt, revealing his navel and only a narrow slice of his trim tummy. There was a small padded bra underneath, to give him a small pair of tits. His outfit was sexy, but not slutty, and he was proud of it. He’d bought it just this afternoon, and he was wearing it for the first time in public as he took his Friday Night Walk.

Darian didn’t quite look like a girl yet, but he no longer really looked like a boy, either. His skin was soft and smooth, his body skinny yet rounded in most of the right places. He had soft pink cheeks and wide, vulnerable blue eyes. His hair was a thick, unisex mop that looked overgrown and unkempt when he was dressed as a boy, but on Friday nights he combed it smooth and fluffed it out, and it looked decidedly feminine.

Behind him he heard the familiar rumbling of a retro muscle car as it turned onto his street. Darian shivered visibly as a tremor of fear and excitement shot through him. The car pulled up alongside him, pacing him. The window rolled down, and a voice called softly to him.

“Hey, beautiful,” said the voice, and there was just a hint of a mocking tone to it. “Can we give you a lift?”

Slowly, Darian lifted his gaze, and Grayson, who was driving the car, locked eyes with him. Darian let those dark, intense eyes bore into him for five long seconds, feeling their power. Then, slowly, he nodded, tossed his soda in the gutter, and headed for the car.

Working to keep his trembling under control, Darian walked around the back of the car to the passenger side, where the door opened for him. The Front seat tipped forward, giving him clear access to the back seat, and Darian climbed in. The front seat tipped back into place, the door slammed, and with a barely-muffled roar the muscle car drove off down the dark street.

Inside the car, Darian sat between two boys. They were the same age he was, he knew, because they’d graduated from High School together, but they were both much larger and more mature than he was, and had been even before he’d begun his hormone treatments. The air inside the car was hot and close, tense with expectation. Darian sat straight, hands folded primly in his lap, staring straight ahead, as though he had no idea what was about to happen. The car roared down the darkened streets, heading for the nightlife of the strip.

Before the car had gone more than three blocks, the boys on either side of Darian seized him, lifted him out of the seat, and laid him face-down across their laps. He yelped and struggled, but it was futile, and within seconds Darian’s short skirt had been hiked up to his waist, his silky panties had been yanked down to his knees, and his smooth, pearl-white bottom was naked, exposed to whatever the boys wanted to do to it. Eager fingers spread his bottom-cheeks apart, revealing his pristine pink anus. Within moments, he knew, the insistent fingers would violate that, too.

This was how it always went. Every Friday night at ten o’clock, Darian would dress up in his sexiest girl-clothes and walk down to the store for a soda, pretending he was a girl the whole time. He never went to that store as a boy, so the clerk knew him only as female. Then he’d walk back toward the house, but he’d dawdle and linger, sipping his soda, as though he was waiting for someone. Then, at some point just after ten, Grayson and his friends would drive up and offer him a ride, and he always accepted. He always acted like it was the first time, too, like he didn’t know what was going to happen.

Of course Darian knew they were going to rape him. They raped him every Friday night. There was a part of him that craved what they did to him, and that part drove him to put himself in their hands again and again. But there were other parts of him that couldn’t accept his perverse desires. There was always a line he had to cross, a point at which his mind tumbled into turmoil and his inner battle began to rage. He just couldn’t bring himself to submit willingly to their demands. Whatever it was, his conscience, his guilt, his pride, his fear, or perhaps just his inability to accept what he was, there was a part of him that simply couldn’t allow himself to be used passively. And so, as his emotions and desires fought within him, he always put up a fight.

It wouldn’t matter. He knew they were going to use him anyway. They had done so many times now, and shown no remorse for it at all. They liked raping Darian. They easily overcame his struggles, and he never cried out too loudly. They knew that, deep down, he really wanted it, and that was good enough for them. They didn’t understand the boy’s inner conflicts, but they didn’t really care. It was an arrangement that worked for everyone concerned.

******

The first time Grayson and his posse raped Darian was just two months ago, on a warm spring evening in April. The four of them had been driving around in Grayson’s restored ragtop GTO, horny as hell and beyond being particular. They’d been friends for years and had done some fooling around with each other, and they were all good with a little guy-on-guy action, if that was what it came to. But they liked cruising for girls, and their Friday nights were devoted to that pursuit.

It was just after ten when they spotted him walking along, navigating the sidewalk with intense concentration. Their eyes were drawn to him instantly, because his plaid skirt was short and he was showing a lot of leg. His white, sleeveless blouse was tied off just above his navel, and with his short, pixie hairstyle, he evoked the impression of a vaguely slutty schoolgirl. They all got a good look at him as they drove by, and he glanced up at their car for just a second, then returned his eyes to the sidewalk.

“Turn around, turn around, she was cute!” said Jase from the back seat.

Mike and Paul were making similar remarks, but when Grayson pulled into a driveway to turn the car around, he had a look on his face like he was trying to remember something. Then his face cleared, his eyes popping wide open.

“Shit!” said Grayson. “I knew she looked familiar!”

“You know her?”

“Yeah! You remember winter of our junior year, when I was dating Selena?”

“That wasn’t Selena, dude!” said Paul.

“I know, shithead!” said Grayson. “That was Selena’s little brother, Darian!”

Blank looks all around. Then Mike asked, “You mean Darian the nerd from Economics class?”

“Yeah, man!” said Grayson. “He graduated with us! And now here he is all dressed up like a fuckin’ girl!”

There was a pause as they all shifted mental gears. “He looked pretty good,” said Jase tentatively.

“You wanna do ‘im?” said Paul.

“I’d fuckin’ do ‘im,” said Mike.

“He looked good enough to me,” said Grayson, putting the car in reverse. “Let’s do ‘im!”

The car rumbled up from behind Darian this time, slowing until it was alongside him, keeping pace with his slow walk. The top was down, and all four of the young men were fully visible, grinning lecherously. Darian looked up at them, his mascara-lined eyes cringing slightly, as though anticipating something unpleasant from them.

“Hey, good lookin’,” called Grayson from the drivers’ seat. “Where you headed tonight?”

Grayson noticed Darian’s eyes widen as the femboy recognized him. Darian looked away quickly, uncertain how to react to a pick-up line from his big sister’s ex-boyfriend. He was clearly flustered, and he stumbled in his high-heeled shoes.

“It’s a nice night for a drive,” said Grayson. “Hop in, we’ll have some fun!”

Darian glanced at Grayson for a long second, then returned his gaze to the sidewalk and kept walking. Two cars went by between them, but there were no other pedestrians nearby. Grayson lowered his voice, taking a serious tone.

“I know it’s you, Darian,” he said, “and I’m not kidding. My friends and I want to take you for a ride. Get in the car.”

Darian stopped and stared at Grayson. The car rumbled to a halt, as well. “I recognize that skirt,” said Grayson with a sly smile. “Does Selena know you’re walking around in her clothes?”

Darian blushed and looked up and down the street. “I don’t know those guys,” he said nervously.

“You know me,” said Grayson. “C’mon, get in. I won’t tell Selena.”

Darian looked around again, licking his lips. He seemed to be actually considering doing it. Grayson pushed him harder. “Hey,” said Grayson, “look at me.” Darian looked at Grayson, and was caught by his intense gaze. “It’s going to be fine,” said Grayson firmly. “Get in the car.”

That did it. Darian crossed the street and approached the car uncertainly. Paul opened the passenger door and jumped out of the car, tipping the seat forward to let Darian into the back. Darian climbed in, Mike and Jase giving him room to sit in the middle between them. Darian lowered himself carefully onto the seat. Jase slipped his hand under him at the last second, palm-up, so that Darian sat on it. The nervous femboy didn’t seem to notice at first, or maybe he just didn’t know how to react.

As the muscle-car took off down the road, the guys introduced themselves. Darian vaguely remembered Paul and Jase from school, but they’d never interacted before. Darian sat tensely, his legs primly together, hands on his thighs. The car cruised slowly through town, heading toward the mall. It would be closed now, but the parking lot would be full of young people, and the strip around it would be crowded with cars, cruising and honking at each other. It was like that every Friday night.

As they drove, Jase started wiggling his fingers underneath Darian’s butt. The femboy started to jump up, staring at Jase with wide eyes, but Jase, cool as a cucumber, put a finger to his lips in a shushing gesture, and smiled. Darian squirmed uncomfortably, clearly confused. Then he was distracted as Grayson asked him what he’d been doing since graduation.

Mike and Jase exchanged knowing glances over the femboy’s head, and Mike asked Darian more friendly questions to further distract him. Meanwhile, Jase’s palm was right up in the femboy’s butt-crack, his long fingers caressing the underside of his balls through his skirt. The fabric was thin, and Jase could feel the warmth and shape of the femboy’s balls right through it.

Darian got more and more flustered, but he didn’t try to do anything about Jase’s hand. Jase took that as permission, of course. He grew bolder now, sliding his palm forward to cup the kid’s balls and stroke the base of his cock with his fingers. Darian yelped and squirmed in his seat, his cheeks bright red, but still he made no protest. Jase’s fingers tickled and teased, and within minutes Darian’s penis was stiff, making a little tent in his plaid skirt.

Mike glanced down at Darian’s lap and made a show of being surprised at what he saw. “Hey!” he said. “Look at you! You got a woody!”

Darian blushed so red he thought he might faint with embarrassment. But before he could think about how to react, Mike slipped his hand right up under Darian’s skirt and grabbed his erection tightly in his hand, gripping it through the thin, silky fabric of his panties. Darian gasped and tried to push the hand away, but Mike wouldn’t let go. He squeezed and stroked the femboy’s stiff little dick through the panties, which quickly started to get soggy. Darian struggled and grasped Mike’s wrist, trying to pull the hand out from under his skirt, but his resistance was weak, and Mike continued, laughing. Then Jase slid his other hand down the waistband of Darian’s skirt and right inside his panties, suddenly touching his hard dick skin-to-skin.

This apparently crossed some line in Darian’s mind, and he jumped up out of the seat, suddenly trying to escape. They wrestled him back down, and during the struggle they managed to slide his panties down his legs and off onto the floor. He found himself sitting in the seat once more, but now his skirt was up around his waist. He was naked from there down, his legs pinned wide apart by the other boys’ knees. Mike was holding his wrists behind his back with one hand, and his whole naked crotch was an open, defenseless playground for Mike and Jase. He was shaved smooth, and his pink little penis glistened under the streetlights as the car cruised slowly toward the strip. Darian whimpered and squirmed in the seat as they began to touch him again, and though he seemed frightened at first, he responded to their fondling with obvious arousal.

They stroked his hard little dick at will, using the constant flow of precum oozing from the tip as lubricant, while tickling and groping his tight, hairless balls and smooth inner thighs from both directions. Paul handed them some lube from the glove box, doubling the slipperiness of the femboy’s erection, and they stroked it gleefully, laughing and joking at his unrestrained responses. Though he continued to squirm and struggle, he never demanded that they stop what they were doing, nor did he ever cry out. The boys took this as encouragement, certain now that Darian was only offering token struggles against them because he really wanted them to continue. Mike told his friends later that he’d been able to hold the femboy’s wrists effortlessly, sometimes with only two fingers, so weak were his struggles. This, as far as they were concerned, was added proof that the femboy wanted to be raped.

Once, when they were stopped at a traffic light, they looked up at the cab of a big semi waiting in the next lane. The driver was staring down at them, with a clear view of Darian’s splayed thighs and his hard dick being teased by the guys on either side of him. Mike and Jase grinned and waved at the trucker, who turned away with a disgusted look on his face. They laughed as the light changed and they left the truck behind.

Soon they were on the strip, the GTO convertible surrounded by cars full of Friday night partiers. Whenever Grayson saw someone he knew he honked and waved, grinning like a fiend. The other guys laughed and joked, waving at acquaintances. They made no effort to hide what they were doing to Darian, though rarely was anyone able to see what was going on below their waists. Most people didn’t even wonder why Darian had that look on his face, and those who did found it either amusing or exciting that a girl was apparently being diddled right there in the back of a convertible on the strip.

Darian was mortified that they were doing this to him out in public. It had taken him months to work up the courage to walk to the store and back as a girl, and now he was half-naked and spread wide, being teased up in the back of a convertible driving down the strip! He blushed almost continuously, and struggled to close his legs or cover himself with his hands, but his tormentors held him firmly in place. Hyper-aware of the people around him, he attempted to at least control his expression, but even that was hopeless.

He whined and whimpered as they toyed with him, his body shuddering frequently, the look on his face like that of a girl on the verge of orgasm. Mike and Jase took turns stroking his excited little cock, keeping it constantly stiff and swollen, keeping Darian on the edge.

Grayson drove them round and round the mall, and Mike and Jase continued to tease his throbbing, glistening dick, laughing and joking, completely unconcerned about who saw them doing it. Every now and then another car in an adjacent lane would be in a position for the occupants to catch a glimpse of what was really going on, and their various reactions were always hilarious to Grayson and his crew.

Finally, just as they were passing the front of the mall for the fifth time, Darian’s cries took on a sudden, wild urgency. His voice rose to a girlish squeal, and his body began to shudder and jerk.

“Here it comes!” said Jase, stroking the femboy’s cock all the harder.

“Oh fuck!” said Grayson. “Not on my seat! Is he coming on the seat of my goddamn car?”

The other boys burst out in uproarious laughter as a jet of pearly jism shot into the air, then fell back onto the seat between Darian’s spread thighs. Another spurt followed, anointing the back of the driver’s seat, and the third one shot between the front seats to splatter onto the center console. Grayson started cursing, which only made the others laugh harder.

Darian came down from his orgasm with a final violent shudder. Never had he experienced a climax like that one, and he could hardly believe how aroused he’d become. But now, with his spooge cooling on the seat between his legs and the car-full of guys laughing at him, he was overcome with humiliation. He tried to hide his beet-red face, which inspired Jase to pull him down until his head was in Jase’s lap. Jase rubbed Darian’s face against the growing bulge in his jeans, and Darian didn’t resist. Jase took the femboy’s head in his hands and pressed his mouth directly against the bulge, and as Darian panted, his hot breath warmed his cock through the thick denim. Jase sighed in pleasure, holding Darian’s head in place, while the bulge in his jeans got bigger. The laughter began to die out, and Grayson glanced back to see what they were doing. When he saw, he took a right onto a dark side-street, leaving the strip.

Mike lifted Darian’s butt and laid it across his lap, while Jase continued to hold his mouth against his cock. Darian wriggled uncertainly in Mike’s lap as his skirt was lifted above his waist once more, leaving his smooth, pale bottom bare and defenseless. Mike’s hands stroked and squeezed his cheeks, and a minute later his fingers were slipping between them, touching his sensitive hole. Again the lube was passed back, and then Darian felt Mike’s wet, slippery finger poking at his tiny pink anus. He yelped and tensed, apparently just beginning to realize what was happening, and he reached back with both hands to push Mike’s hands away from his ass. Mike grasped his wrists firmly, and held them at the small of his back with one hand, while his finger again pressed against the femboy’s tender anus. Darian gasped as Mike’s finger penetrated him, slipping up inside his bottom-hole. Panic seized him, and he began struggling for real. But it was useless, for he was tightly pinned down, held in place by two strong men. As he drove, Grayson pushed a button, and the roof slowly rose to cover them, shutting out the wind and enclosing them in relative quiet.

In the now-enclosed space, they all enjoyed the femboy’s frantic yelps and groans as Mike worked his lubed finger up into the boy’s ass. Mike took his time, working one finger in and out for a while before going to two fingers. After a few minutes one of Mike’s hands slipped under Darian, and began teasing his still-lubricated little cock. To his surprise, it responded quickly, stiffening in his fingers. Mike announced the development to the others, who laughed, but the laughter was muted now, overwhelmed by the growing sexual tension. They could all feel it in the long silences. What they were doing to Darian was becoming more serious now, going past the joking and teasing stage. Darian gasped and whimpered, the noises sending mixed signals now as Mike’s fingers continued to move around inside him.

Jase unzipped his pants and hoisted his cock out into the open. It was fully hard, and the size of it was impressive. Darian didn’t resist as Jase shifted his position and pressed the head of his cock against his mouth.

“Open your mouth,” Jase growled.

Hesitantly, Darian did as he was told, and Jase shoved his cock inside. The fat, warm cockhead filled his mouth, bumping against the back of his throat. Though he had never had a cock in his mouth before, Darian knew what he was supposed to do. He closed his lips around the thick shaft and began to suck.

It was quiet in the car, Darian’s distressed cries muted now by Jase’s cock. Grayson cruised slowly onto darker streets, circling around to the empty parking lots behind the mall. The tension mounted as the boys watched Mike’s fingers sliding easily in and out of Darian’s ass, the boy’s struggles gradually becoming less frantic.

Finally, it seemed as though Darian wasn’t really struggling at all, and sometimes it looked like he was actually arching his bottom up into Mike’s plunging fingers. With a series of quiet nods and knowing grins, the boys decided Darian was ready. Grayson pulled into the parking lot that was the farthest from the mall building. It was empty now, and Grayson cruised to the darkest corner of it and parked the car.

Mike withdrew his fingers, and he and Jase lifted Darian up into a sitting position once more. The boy blinked and looked around, as though they’d woken him from a nap. Jase began lubing up his cock, which was already glistening with Darian’s saliva. Darian saw what Jase was doing, and his eyes widened. He looked around at the guys in the car, and recognized the intent they all shared. His eyes returned to Jase’s cock, which was twice the size of his own, and stared. He looked scared, but still he offered no protest.

While he’d fantasized many times about taking a cock in his ass, Darian was a virgin. Aroused as he was, a part of him wanted them to use him, wanted to finally experience penetration by a real cock, but other parts were terrified. The sheer size of Jase’s cock was frightening all by itself.

When Jase was ready, he and Mike lifted the slender femboy, positioning him over Jase’s thick, hard pole. Darian struggled feebly as they slowly lowered him into Jase’s lap, guiding the huge cock into the femboy’s cringing bottom-hole.

Darian yelped and groaned as Jase’s cock slid slowly into the tight confines of his defenseless virgin rectum. Helplessly, he sank down onto it until he was sitting solidly in Jase’s lap, fully impaled on his cock. Darian’s eyes were wide and wet, his mouth open as he gasped again and again, but he was no longer struggling. He seemed afraid to move, now that Jase’s cock was inside him. Jase let him sit there, getting used to it, for nearly half a minute before he began to slowly rock his hips, working his cock just a couple of inches in and out of the impaled femboy. Darian groaned, clutching at Jase’s thighs like a sailor on a stormy sea.

Jase moaned softly. “Damn,” he said, “this is sweet… his ass is all hot and buttery inside…”

Gradually he began to take deeper strokes, evincing more desperate reactions from the tense femboy. Darian clutched Jase’s thighs urgently, as though he was afraid he’d fall off his lap, or perhaps afraid that if he didn’t hold himself up, he might be speared by more of Jase’s cock than was already inside him. But Jase wasn’t concerned about the femboy’s fears. Grasping Darian’s hips, he forced him all the way down on his cock, drawing a long squeal from him. But before the squeal had even ended, he was already pumping in and out, fucking deeply into the femboy’s tight, squirming ass. Before long Jase was fucking Darian freely, he and his friends exchanging growing smiles as they all listened to the urgent gasps and cries coming from the helpless femboy. All of them were burning with arousal now, impatient for their turn to fuck the exotically feminine boy.

After a few minutes Jase grew frustrated with his limited range of motion. Seizing on an idea, he lifted the femboy off of his cock, and pounded the back of Grayson’s seat. “Open the door,” he said. “Let me out.”

Grayson climbed out of the car and tipped his seat forward, and Jase barreled out, dragging Darian with him by his wrist. When they stood outside the car, he looked quickly around, then grabbed Darian by the back of his neck. Darian struggled, frightened by Jase’s roughness, but Jase manhandled him into a bent-over position and thrust his head back into the car through the open rear window. He pushed until Darian was inside up to his waist, only his ass and legs still outside, his hips and thighs pressed against the fender. Finally understanding what his friend was doing, Grayson grinned and closed the car door.

Jase flipped Darian’s skirt up, pushing it above his waist, baring his pale ass to the night air. Then he grasped his turgid cock and pressed the fat head of it between the femboy’s defenseless cheeks.

Inside the car, Mike and Paul had a perfect view of the femboy’s wide-eyed, flushed face as Jase forced his cock back inside his tight virgin ass. Darian cried out as he was suddenly filled once more with cock. He scrabbled blindly for something to brace his hands on, settling finally for the armrest on the inside of the side panel. Jase began to fuck him with long, hard strokes, plunging far more deeply than he’d been able to while sitting in the car. Darian squealed with every stroke, his eyes wet now with tears.

It was a hell of a show. Jase fucked the helpless femboy long and hard, oblivious to his cries. Soon Darian’s cheeks were red and wet with tears, his wide eyes sometimes seeming to plead for mercy, sometimes wild with pain, and sometimes blissed out with indescribable pleasure. His cries ran the gamut from shrieks and squeals to gasps and groans. For a grand finish, Jase pounded the poor femboy’s bowels like a jackhammer, and Darian wailed so loud that Mike covered his mouth with both hands to make sure no one heard him from the street. Jase slowed and stopped as the last squirt of semen filled the femboy’s rectum, and after a few deep breaths, he withdrew.

Grayson was ready and waiting to take his place, and drove his own cock into the femboy’s pale round ass only seconds after Jase pulled out. Darian didn’t even have time to catch his breath before he was again being hammered by a hard, hungry cock. Grayson wasn’t quite as brutal as Jase, but he fucked him long and hard, with another rapid-fire ending.

After Grayson shot his load into the femboy’s hot, slippery rectum, Mike climbed out of the car and took his turn. Mike exerted a little more control than his friends had, and spun out his pleasure for a long, sweet thirty minutes. He varied his strokes, sometimes going slow and deep, sometimes fast and hard, keeping himself from coming for as long as he could. Eventually, though, the heat and creamy tightness of the femboy’s bowels drove him beyond restraint, and he, too, pounded a hot load into Darian’s ass.

Then it was Paul’s turn. His cock wasn’t as thick as the others, but it was long, and it went deep up inside Darian’s body with each measured stroke. He held a steady pace for a long time, sliding his smooth shaft nearly all the way out, then all the way back in with each stroke.

Darian was no longer squealing and crying. As Paul’s long cock slid in and out of him, the little breathy groan that he made with each inward stroke could have been construed as an expression of pleasure as easily as one of pain. His eyes were closed most of the time now, his mouth open, his body tense. When Paul finally felt himself coming, he sped up to a creditable speed, drawing a long, high-pitched wail from the femboy.

After they’d all piled back into the car, there was an uncomfortable silence. Now that their lust was sated, the boys realized that they’d just, effectively, raped Darian. While he’d been giving them mixed signals, they realized that he could press charges if he wanted to. But they didn’t know what to do about the situation. Grayson stopped at a convenience store and bought everyone a soda, including Darian, who accepted it without a word. They headed back toward Darian’s house, and as they neared it, Grayson told him that he would never tell Selena about any of this. As he pulled up in front of the dark house, he locked eyes with Darian once more.

“Are you okay, Darian?” he asked. It was all he could think of to say.

Darian held his gaze for a long moment, then nodded solemnly.

Darian climbed out of the car, his soda in one hand, his soggy panties in the other. He didn’t say goodnight, he just stood and watched them drive away, semen trickling down the inside of his thigh.

It was two weeks later that they drove down Darian’s road again on a Friday evening, and saw Darian strolling slowly down the same sidewalk as before, wearing a short skirt and halter-top. So they pulled over next to him and asked him if he wanted a ride. Without looking directly at them, he nodded and climbed in, just like that. So they gang-raped him again, and it was the same story as it had been the first time. Ever since then they’d been picking up Darian every Friday night.

******

And so it was that Darian found himself face-down across Mike and Jase’s laps two months later, once more at the mercy of Grayson’s posse. Jase held the femboy’s head and shoulders in his lap while Mike worked his fingers up inside Darian’s tight bottom-hole. Jase wrapped his strong hands around Darian’s head, forcing the femboy’s face further down into his lap, pressing his mouth against the bulge of Jase’s erection. Darian whimpered and squirmed, and as he panted, his hot breath warmed Jase’s cock through the thick fabric of his jeans.

“Oh, yeah, that’s it,” said Jase, pressing Darian’s open mouth tight against his hardening shaft.

Meanwhile, Mike had worked two lubricated fingers deep up into Darian’s ass. Darian groaned as he was violated, the sound muffled by Jase’s denim-covered cock. All four guys chuckled at the sound. It sounded so desperate and forlorn, yet they all knew how much it excited Darian to have his ass penetrated. He struggled, but they knew his little cock was rock-hard right now. He would never admit it, of course. Every sound he made was in keeping with his own inner storyline, that he was being raped against his will. That was how it always went with Darian. Except, of course, when they made him come. Ah, how he squealed when he was coming!

While Mike pumped his fingers inside the femboy’s tight ass, Jase decided it was time to get their boy-toy’s mouth around his cock. He unzipped his jeans and pulled his pulsing erection out into the open air. Darian tried to pull away from it, but Jase got a big handful of his mop of dark hair and dragged his face in close.

“Suck my cock, little femboy,” he growled.

As if that had been all he needed, Darian opened his mouth, letting the semi-hard meat slide between his wet lips. His tongue licked the underside of it, tasting the salty flesh. Jase’s cock was thick and heavy, filling his mouth to capacity. All these guys had cocks that dwarfed his, and the difference never failed to intimidate him.

Meanwhile, Mike’s fingers inside his bottom-hole triggered waves of emotion inside him, as his rising desire to be overpowered and used raised a new surge of shame and guilt within him. He could feel his own penis, now stiff and swollen, rubbing almost painfully against the rough cloth of Mike’s jeans as he squirmed, and it only made him squirm harder.

Jase had two handfuls of Darian’s hair now, giving him complete control of the femboy’s head, and he was moving Darian’s mouth up and down on his cock, making him gag each time he shoved his head down. Darian tried to suck the fat monster, but it was all he could do to keep his lips closed around it. He was being increasingly distracted, as Mike pumped his fingers in and out of his ass rapidly now, drawing rhythmic grunts from him that he seemed to have no control over.

“Ah, sweet music,” Grayson chuckled, glancing back from the driver’s seat. He turned on the radio, dialed it down low, then punched the buttons until he found some classic rock with a solid, thumping beat. “There,” he said with a grin, “make ‘im do it to the beat.”

Laughing, Mike timed the thrusts of his fingers to the beat of the music, and Darian’s grunts of distress, muffled by Jase’s cock in his mouth, became a counterpoint to the music. They all laughed, and Mike, Grayson and Paul began bobbing their heads in time with the beat.

Mike began to work a third finger into Darian’s ass alongside the other two, stretching his anus even more. The double violation of both his mouth and his ass was so overwhelming that the battle going on inside Darian’s mind finally receded into the background. He had no choice but to surrender to the moment, to give up and just feel his own utter helplessness. Unable to think, there was no conflict, and Darian floated in a rapturous bliss of submission.

Jase fucked Darian’s mouth for almost five minutes, though it might have been a week for all Darian knew. He was yanked out of Jase’s lap abruptly, the thick, throbbing cock that had become the center of his world sliding out of his mouth with a wet pop. He came up dizzy, disoriented, and gasping for air. Strong hands sat him up in the seat, and he looked around, blinking and confused. Hands brushed at his hair, smoothing it. Darian looked at Mike and Jase, and they both had mischievous grins on their faces. Whatever they were doing, they seemed to have planned it in advance.

Beside him, Mike was taking out his own cock and rubbing it with lubricant. On the other side, Jase was reluctantly zipping up his jeans. Then Mike and Jase both lifted Darian up and sat him in Mike’s lap. Darian felt fingers fumbling beneath his ass, and then he felt the hot, hard tip of Mike’s cock touching his anus. It skittered back and forth for a moment, then it zeroed in on the well-opened hole and drove inside. Darian groaned loudly as the thick, hard cock plunged into the hot depths of his ass. He sank into Mike’s lap, and his legs suddenly went weak, so weak he couldn’t stop the descent until he was completely impaled. The boys laughed as he flailed helplessly, gasping as though he couldn’t breathe. His eyes filled with tears, and he squirmed weakly, even pushed against Mike’s lap with his hands as though trying to escape. Mike held him in place easily, and gradually his struggles subsided.

Darian’s cock was still stiff as ever, and Jase reached over and stroked it teasingly. As he did, Mike began rocking his hips, fucking Darian’s ass slowly. Darian whimpered, losing all strength.

“I think we’re ready!” said Grayson. “Let’s hit it!”

With that, he pushed the button that lowered the convertible’s top, and as it whirred, exposing them to the open air, Grayson pulled the car out onto the strip. Darian felt a surge of panic as he realized what they were doing. They hadn’t taken him back to the strip since that first wild ride back in April. Now they were doing it again, and this time he had a cock inside his ass! Terror filled him as he looked around and saw faces everywhere, some of them looking at him, and some of them belonging to people he actually knew! The femboy blushed a deep crimson, and tried to sink back into the seat to become less visible. It didn’t work, because he was still propped up on Mike’s hips, and when Mike began to rock to and fro, fucking Darian’s ass deeply and slowly, the impaled femboy couldn’t repress his reactions. He groaned with each thrust, and the look on his face was a giveaway to anyone paying attention.

Mike arranged Darian’s skirt so that it covered his stiff dick, fussed with the femboy’s hair a bit more, and then settled back into the seat. He had turned a bit sideways so that it wasn’t immediately obvious that Darian was sitting on his lap, but anyone who took more than a quick glance could see that he was. The guys thought the situation was hilarious, and they couldn’t stop laughing, looking around constantly to see if anyone could tell Darian was being buggered right out there in the open. They were surprised at how few people noticed, and that only made them laugh harder.

Grayson cruised the strip, waving and honking, snickering almost non-stop. In the back seat, Mike and Jase laughed, Jase making stupid sex jokes, while Darian bounced slightly up and down, a stricken look on his reddened face that he couldn’t seem to control. Mike’s cock was plunging up and down deep inside his bowels, draining away his self-control and scattering his thoughts.

On their fourth time around the strip, Mike shot his load inside Darian’s ass, groaning and shuddering. Grayson quickly pulled onto a dark side-street, and Darian was lifted off of Mike’s softening cock and lowered immediately onto Jase’s waiting erection. Then they returned to the strip and resumed their circling while Jase pounded his cock into Darian.

There was less laughing now, but the guys still grinned like hyenas as they looked around at the people in the cars around them. People often stared at Darian, wondering what was wrong with him. Sometimes someone realized what was happening, and laughing hysterically, pointed it out to the others in their car. Darian was painfully aware of these times, but there was nothing he could do. Whenever he managed to compose his face into something resembling a normal expression, Jase deliberately began fucking him harder, ruining his hard-won control.

Finally Jase, too, came in Darian’s ass, and they had to pull over on a dark side-street while the guys switched places, Paul and Grayson getting in back so they could take turns fucking the femboy while Mike drove the big muscle-car round and round the mall. It went on for hours.

At one point Darian told them that his parents were due to get home at midnight, and he needed to check in, so Mike let Darian use his cellphone to call his mom. Of course Grayson didn’t take his cock out of the femboy’s ass, but at least he held it mostly still. Darian’s voice quavered a little as he told his mom that he was at a friend’s house and would be home late. Then he gave the phone back and groaned, clutching the seat, as Grayson resumed fucking him.

They made a night of it, each of them taking at least three turns fucking the femboy’s hot, slippery ass before they finally dropped him off at his house at half-past two in the morning. Darian stood there, watching them drive away, his ass throbbing and hot semen dribbling down both his legs. Next week he would be leaving for college, and would never take a ride with those guys again. He knew that, even though Grayson and his friends were assholes, he was really going to miss these wild Friday night rides.
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#9
One night in a bar

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#10
When I Was a Girl

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Poor Timothy! He was just starting to get comfortable going out as a girl. He’d go to the mall, where he started hanging around with a gang of mall-rats. He dealt with the boys’ advances by sucking them off in the janitor’s closet so they wouldn’t learn his secret, but soon he was sucking all five of them. The girls in the gang didn’t care for that, and arranged a bit of revenge. They set up a group photo of the whole gang, with Tim in the front row. Just before the shutter clicked, they flipped up his skirt, yanked down his panties, and held up a big “slut” sign above his head. The photo revealed more than they’d thought it would!

Tim fled the mall never to return, but the photo went viral. It turned up in the hands of a guy who’d been bullying Tim for years, who threatened to expose Tim’s secret to the whole school. Tim had to do whatever the bully wanted. What did he want? Tim was going to have to dress up as a girl for him and his friends every week until they graduated.

The bullies had planned on just humiliating Tim, but when they saw how hot he looked as a girl, well, other ideas came to mind…

Ron and his buddies soon had Tim coming to their clubhouse, a low-rent warehouse unit in the industrial zone, twice a week. Tim showed up in his well-practiced girl persona, dressed to the nines, only to be humiliated, stripped and used. Usually it began with demands that he suck their cocks, but before long the horny, impatient bullies would be taking turns pumping Tim’s tight bottom-hole as well.

Tim told himself that he was only going along with their abuse because he didn’t want that incriminating photo to ruin his last few months of high school, but he often found himself daydreaming in class about what he would wear to the next debauchery and what Ron and his crew might do to him.

Then, one Saturday night after Tim had sucked off all four of them, the bullies tied him up in nothing but his stockings and told him they had guests arriving soon to fuck him. The “guests,” it turned out, were just random guys that the bullies had brought in off the street, guys who were willing to pay fifty bucks to fuck a naked sissy-boy.

One after another, they lined up to use Tim’s helpless body. Each in his turn, the faceless strangers thrust their hard cocks up into Tim’s ass, plunging his hot bowels with a sense of desperation until they had added another load of semen to the soup inside him. Some turned their faces away in revulsion, some closed their eyes and pretended he was a girl, and some groped his stiff little penis with thick, calloused fingers while they pounded him from behind.

Despite his desperate shrieks and squeals and intermittent tears, Tim came three times during the seemingly endless interlude. While most of the men were quick, hard and brutal, there were occasional moments of tenderness, too…



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Ron and his buddies started inviting their friends and acquaintances, and sometimes the customers they sold drugs to, to enjoy their helpless fuck-toy. Soon every visit to the warehouse was a gang-bang for Tim. He could never admit how much he had come to crave these sessions, or how much they turned him on.

But his penis gave him away every time! Not only did it start getting hard every time they started to touch him, he often came while he was being fucked, which amused the hell out of the bullies. They got their jollies from humiliating Tim, and there he was humiliating himself while they raped him! They all laughed every time Tim started to squeal and squirt, and it became part of the game to see who could fuck him hard enough to make him cum…

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Ron and his buddies sometimes put on shows for their growing entourage of “friends,” making Tim into a helpless, humiliated spectacle for their amusement.

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Before long, stories about Tim’s secret life as a femboy fuck-toy started making the rounds at school. Tim was unaware of it until the day he got dragged into the boys’ restroom by three guys he hardly knew.

“We heard you like dressing up as a girl and getting fucked in the ass,” they said as their hands dove into his clothing, touching and fondling his body intimately.

“N-no, it’s not true,” said Tim, desperately trying to push their hands away.

But Tim’s penis betrayed him, as it always did, stiffening at their touch. Despite his attempts to resist, the strangers had soon gotten his shirt open and his pants down, and his little white panties were no protection at all. Hands were stroking his erection freely, fingers forcing their way up into his tight little anus. They were all over him at once, and though he tried to fight them, within minutes he was panting with need, his knees going weak, his thighs trembling. Fingers slipped in and out of his hole at will, lubing it and stretching it.

Finally he found himself bent over the sink, gazing at his own glassy-eyed reflection as a thick cock penetrated his ass. They each fucked him long and hard, while he whimpered and groaned and sobbed, drool running from his chin as his face was smooshed against the mirror. He never did make it to Geography that day.

From then on, Tim had to spend his study hall hour every Monday and Wednesday in the restroom taking cock from a growing number of guys from his own senior class. They all promised not to tell anyone as long as he kept letting them use him, yet somehow more and more guys were showing up every time…

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It all came to an end a week before Tim graduated from high school. Ron and his buddies had been selling drugs to kids, and the cops busted their clubhouse while they were gang-banging Tim. The bullies went to jail while Detective Garret untied Tim, helped him get dressed, and took his statement. As he was driving him home, he told Tim he wanted to date him after he graduated.

Three weeks later Detective Garret took Tim to the kind of restaurant Tim had only seen on TV. They had a marvelous time, and Tim was the best girl he knew how to be.

Afterward Garret took Tim to his hi-rise apartment downtown. There he made passionate love to Tim, fucking him long and hard, yet with skill, compassion and experience. He fucked him with brutal tenderness and caring cruelty. He fucked Tim like the boy had never been fucked before.

By the end of the night Tim was in love, and when his new master asked, Tim promised, on his knees, with tears and semen all over his face, to be his master’s girl for ever and ever and ever.
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