By Shadowjack (text and illustrations)
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.
This story first appeared on Shadowjack's site.