By Shadowjack

(Text and art)

“Hey Rentboy, it’s time!”

A shudder went through Darby at those words. Whenever his housemates called him “Rentboy,” it only meant one thing: It was time to earn his keep. He’d been sharing the house with Sam, Justin and Trent for a month and a half now. He had no income and couldn’t contribute at all to the rent or food bills, so his housemates had worked out a way for him to do his share.

Darby dreaded these weekly sessions. During the week his housemates could knock on his door any time they pleased, and he was obliged to stop whatever he was doing and suck their cocks until they spurted into his mouth. That was bad enough, but on Saturdays, when they were all together, they really put him through the ringer!

"I'm doing my homework."

“I’m doing homework!” he called from inside his room. “Maybe later…”

That was as far as he got before Justin pushed his door open and strode in. Darby’s bowels turned to icewater as Justin grabbed him by the arm and pulled him out of his chair. “When we say it’s time, it’s time,” said Justin, dragging him toward the door.

“But it’s so early! It’s only like three o’clock! I gotta do my homework…” It was useless.

Justin walked him out into the living room, where Sam and Trent were sprawled on the run-down, blanket-covered flea-traps they called furniture. He positioned him in the middle of the floor, between the couch-like lumps his housemates sat on. “Strip, Rentboy!”

Starting to tremble now, Darby stripped out of his tee-shirt and shorts and stood naked. He knew his three housemates were staring at his slender, pale body, but he couldn’t look them in the eyes. He was skinny and underdeveloped, he knew, especially in comparison to these guys, but for some reason they seemed to like his body. They often said he looked more like a girl than a boy, but he was sure they said it just to humiliate him. He kept his gaze on the floor, and he could feel himself blushing.

“Why you always make such a fuss every time we do this?” asked Trent from behind him. “We know you fuckin’ love it!”

“No I don’t!” Darby protested. “I keep telling you, I’m not gay!”

“Yeah,” said Trent, his voice coming from much closer now. “You do. And we keep proving you wrong, don’t we?”
"And we keep proving you wrong, don't we?"

Darby jerked as Trent’s hand touch his bare ass-cheek. He tensed and held still as the hand caressed him, slipping easily between his slim thighs and touching his ball-sack from behind. Now he felt Trent’s hot breath on the back of his neck, felt his rough jeans brush against his flank, felt Trent’s other hand reach around him to touch his small, withdrawn penis. A kind of panic seized him then, and Darby pushed the hand away from his dick violently. He spun away from Trent, but that only put him in arm’s reach of Sam. Sam grabbed him by the hips and pulled him down into his lap. Darby struggled while Sam twiddled his tiny penis between his fingers. Unable to pull away, Darby pushed the fingers away from him.

Sam chuckled and grasped him by the hips. He lifted him, spun him around, and laid him face-down across his lap. Darby squirmed, trying to escape, but Sam was much stronger than he was. Sam lifted one knee, and Darby’s butt was hoisted high. Sam gripped a smooth butt-cheek and squeezed, his fingers brushing against Darby’s tiny pink anus.

Darby yelped and fought harder, finally breaking Sam’s grasp on his ass with both hands. Sam slapped his butt hard with the palm of his hand, and Darby squealed and bucked, covering the spot with his fingers. Sam grabbed both his wrists firmly and planted them in the small of his back.

“Justin, you wanna grab me the towels and tape?” said Sam.

Justin pulled three thin white dishtowels and a roll of duct tape from a bag next to the couch. It seemed they’d planned this, as Justin helped Sam wrap Darby’s forearms together in a towel, then wound some duct tape around it. Darby’s arms were now bound tightly together in the small of his back, but they weren’t done. Another towel went around each of his elbows, and the duct tape was wound round and around his arms until they were encased in a tight, shiny silver sheath all the way up to above his elbows.

Darby’s hands were rendered completely useless, and he found he was entirely helpless as Sam began to spank his bare bottom with a hard, heavy palm. Darby squealed and bounced in Sam’s lap, struggling futilely. The spanking stung terribly, making his struggles desperate, but Sam didn’t stop until both Darby’s cheeks were bright red and tears stood in the boy’s eyes.

At last the spanking stopped, and Darby lay, tense and panting but no longer struggling, as Sam explored the shallow groove between his cheeks. Thick fingers stroked his tender anus, and he clenched his cheeks against them, but it was useless. Trent tossed Sam a small plastic bottle, and then Sam’s forefinger, slippery with lube, worked its way up inside Darby’s bottom-hole. Darby whimpered and struggled weakly, but there was nothing he could do. The finger wriggled around inside him, and he felt his penis begin to stir. He recognized the warmth growing in him, and he knew what it meant. A wave of panic galvanized his struggles, but nothing he did could dislodge the intruding finger, or stop the rising tide of arousal that was washing over him.

In less than five minutes, Darby was like a different person. In the heat of arousal, he could no longer resist what they did to him. He wanted to be touched, wanted to be violated and used. His penis, not so tiny now, was hard and straining, and his spanked bottom rose hungrily to take more of Sam’s fingers.

In less than five minutes, Darby was like a different person

This was how it always went in their Saturday sessions. Darby dreaded the emotional rollercoaster, and was terrified of his own desires. He feared the things his out-of-control libido allowed his housemates to do to him, and his humiliation and guilt afterward were grinding. But at the same time, there was something inside him that craved the absolute submission, and the violating cocks that used him so roughly. When his perverse lust was in control, Darby could resist nothing.

Sam lowered him onto the floor, making him kneel in front of him. With a grin, Sam shucked out of his jeans and briefs, baring the thick, dusky cock that nestled between his muscular thighs. When he ordered Darby to suck it, the boy didn’t hesitate. Bending low, he took the fat cockhead between his lips and sucked it inside his hot mouth. As it stiffened and lengthened, he voluntarily took more of it into his mouth, until soon he was slurping up and down the thick shaft, sometimes making himself gag as he pressed it against the back of his throat.

Behind Darby, Justin and Trent sat on the couch, sipping beers and holding their cocks in their hands. Before long Justin stood up, lubed himself up and knelt behind Darby. His rock-hard cock forced its way through the tight pink sphincter and up inside the velvet heat of the boy’s colon. Darby bucked and wailed as he was penetrated, wagging his bottom from side to side, but Justin persevered, and once the wailing and struggling died down a bit, he sank the rest of his cock into the boy’s ass. Once he’d begun a steady thrusting rhythm, Darby’s cries became less desperate and turned into rhythmic grunts. Shortly after that, Sam wrapped his hands around Darby’s head and forced his head down on his cock, plunging it down Darby’s throat. Despite the choking noises that revealed his distress, Darby didn’t try to resist.

After Sam shot a load of thick semen down Darby’s throat, they picked the boy up and moved him over to Trent. Darby sucked Trent’s cock voraciously, and when it was fully hard Trent began shoving it down the boy’s throat. Justin, meanwhile, resumed fucking Darby’s ass. Darby was no more than a submissive fuck-toy at this point, and they could do as they pleased with him.

Soon Justin came in Darby’s ass, and then Trent held him down while he shot his load straight into the depths of his esophagus. Darby was aroused beyond thinking, but he fully expected his housemates to continue fucking him until they’d turned him into a cum-dump. That’s what they’d done on previous Saturdays. But this time they seemed to have other plans.

They splayed him out on the couch, and before he’d figured out what was happening, they were shaving him. They shaved his legs, his torso and his crotch until he was smooth as a baby, without a body-hair in sight. They led him into the shower and quickly hosed him down, dried him off, and brushed out his shaggy blonde hair. Then Sam and Justin started putting off-white women’s stockings on his legs, while Trent applied make-up to his eyes. Perfume was dabbed behind his ears, a leather collar with a leash was buckled around his neck, a huge overcoat was draped over his shoulders, and then he was being led, wobbling on white high-heeled pumps, out the door.

When the cool night air hit his naked skin Darby’s brain began trying to re-engage. His housemates, fully dressed now, hustled him into the back seat of Trent’s car, and then they were driving. Some minutes later, Darby had finally pulled himself together enough to ask what was going on.

“It’s like this,” said Sam. “The rent on the house is a lot for three college students to come up with every month. It’s nice that you take care of our sexual needs, but we are in serious need of cash.”

Darby was wide-eyed. “You’re gonna make me sell my body on the street?”

Sam laughed. “No, nothing like that. There’s a prep-school over in Rochester Heights, where the rich kids go to college. There’s a particular fraternity there that has a thing for femboys. Every month they throw a big party, and they all bring their femboys and show them off to each other. We found out that the femboys get paid a thousand dollars to go to this party. So that’s how you’re gonna help us with the rent. All you gotta do is dress up and go to this party.”

Darby was trying to wrap his mind around this, and not doing well. “Femboys?”

“Yeah,” said Sam. “Boys who dress up as girls. You’re one of the prettiest boys we’ve ever seen, so we’re fairly sure you can pass as a femboy. Just, you know, act like a girl.”


Darby tried to argue, but his housemates had clearly made up their minds. They seemed to think this would be easy money for him, that all he had to do was strut around on his high-heels and act like a girl for a few hours while the students and alumni of the fraternity drooled over him. He was terrified, but here he was, naked, with his arms securely taped up behind his back, and he really had no choice but to go along with it.

The building was at least a hundred years old, built of dark red brick and surrounded by trees, shrubs and darkness. Trent dropped them off by the front door, and Sam and Justin led Darby inside between them. The small foyer was manned by a preppie-looking young man, who eyed them suspiciously until Sam pulled the overcoat off of Darby and revealed him in all his feminized nudity. The preppie smiled. There was a brief conversation between Sam and the preppie, which Darby couldn’t hear over the roaring in his ears. He was blushing so hard he thought his head was going to catch fire. A handful of cash changed hands, a couple of forms were signed, and then Justin unsnapped the leash from Darby’s collar.

“Have fun, Rentboy,” he said with a grin. “We’ll be back to pick you up at three.”

“Wait, what?” said Darby. It was all developing so fast!

“Three A.M.,” said Sam, clapping him on the back and almost knocking him off his heels. “That’s when the party’s over. Relax, enjoy!”

And then they were gone, and the inner door opened, and Darby was propelled through it into the hubbub of a major party, already in progress. He stumbled forward several steps before he managed to get his balance.

There were men of all ages, well-dressed and dignified-looking, sipping drinks and expensive beers and holding casual conversations with each other. They held leashes, and on the end of the leashes knelt naked femboys. Like Darby, they were young and attractive, and decidedly feminine. Some of them really looked like girls, except for the lack of breasts and the stiff penises sticking up from between their thighs.

And the boys weren’t just kneeling there looking pretty, either. Darby could see three who were industriously sucking the cocks of their well-dressed keepers. One boy was squealing helplessly as a man slowly inserted a bright red swizzle-stick, inch-by-inch, into his penis-hole! Another boy, just across from him, had one of the swizzle-sticks stuck all the way into his urethra, only the head, sporting a logo for some kind of liquor, protruding from the tip of his cock. Across the room, barely visible between the many bodies, a naked boy was gagging and groaning as two men fucked him hard between them. Cries of sexual distress issued from corners and other rooms that Darby couldn’t see.

This was like no party he’d ever imagined, and was certainly not how Sam had described it! What was going to happen to him here? As he stood there, eyes wide and head spinning, two well-dressed preppies strolled up to him, eying his body up and down.

“And what have we here?” said one. “A femboi with no leash? Well, you know what that means.” The other guy laughed.

Darby stared at them, not understanding.

Darby stared at them, not understanding.

The guy who’d spoken, a handsome man in a tan sports jacket, stepped closer and idly twiddled Darby’s left nipple with his fingers. “You don’t know the rules, do you? You are new.” Darby’s nipple had stiffened immediately, and the guy switched to the right one. “When a femboy shows up without a daddy, it means he’s fair game for everyone. You’re going to be seeing a lot of action tonight, sweet-nips!”

Tan Jacket’s friend moved in close on Darby’s other side, and reached down for a handful of Darby’s junk. Darby’s penis had again shrunk to its non-erect thumb-size, but as the guy’s hand closed around his balls, the pad of his thumb started rubbing against the sensitive head of the little nubbin. Shocked at being touched so intimately by a total stranger, Darby gasped and tried to pull away, but the guy grabbed his ass firmly with his other hand and pulled him back.

“L-look you guys, I think this was a mistake,” said Darby. “My housemates brought me here, and I think maybe it was a joke. They didn’t know…”

“Oh, it’s way too late to back out now,” said Tan Jacket with a grin. “You’re ours for the duration.” He pinched Darby’s stiff little nipple hard enough to make him yelp.

A third guy came over, holding a beer. “What’s this,” he said, “new meat?”

The other two greeted him, calling him Ian. “Just walked in the door,” said Tan Jacket. “I’ve never seen him here before.” Their manner inferred that Ian was somehow of a superior status.

Tan Jacket stepped around behind Darby to give Ian a better view. Darby felt the guy’s hands begin to caress his bare bottom-cheeks, and he shuddered involuntarily. Ian surveyed Darby’s pale, clean-shaven body and smiled.

Darby was terrified, lost and out of his depth. He was naked and helpless, in the hands of strangers who clearly saw him as no more than a sexual toy. He had no idea how far they might go, or if they even had limits. And in the back of his mind was the chilling knowledge that if they got him aroused enough, he would lose control and let them do whatever they pleased.

To his horror, he realized that his penis was beginning to swell. The guy was still fondling his balls and rubbing his dick, and the efforts were starting to yield results. What’s more, Tan Jacket had a finger up between his cheeks, probing at his sensitive anus, and it was about to push through and go inside him! Darby tried again to pull away, but the one guy had his balls firmly in his hand, and he held Darby in place with a grip of iron. Darby whimpered as his cock, wholly against his will, continued to thicken and extend.

Slippery now with some kind of lube, Tan Jacket’s finger slid easily right up into Darby’s rectum. He gasped loudly, and involuntarily his hips thrust forward. All three guys laughed. Darby’s penis was starting to stand up on its own, filling out to its full, erect size. The guy was unabashedly stroking it now, and the friction felt good.

Darby was on the verge of panic. He couldn’t allow these guys to get him aroused! He knew what he was like when he lost control, and the image of him becoming that wonton, submissive sex toy for these assholes was unbearable! He felt his face flushing, and he squirmed helplessly in place. Within moments his cock was fully erect, standing tall and proud in spite of his fears. The guys were apparently passing a tube of lubricant back and forth, because now the hand stroking his cock was sliding freely and pleasurably up and down his helpless shaft. Behind him, Tan Jacket had two fingers buried in his unwilling ass, and they were slipping and sliding around without restraint.

Darby’s ears began to rush, his face burning, and heat was also radiating from his loins and spreading outward. It was happening! His cock throbbed as the stranger’s hand glided up and down its length, and the pleasure was overcoming his resistance. There was no stopping it now, and Darby whined and clenched his eyes shut, his humiliation complete as his hips began to rock back and forth on their own…

This story appeared first on the pages of Shadowjack's femboys.