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Date Night 3
by Emile, 2010
Usual caveats apply.
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Nico had completely freaked out, and refused to leave the car. Finally, Trent relented, and closed the door, ordering the driver to go 'to their usual spot'. Nico was sure a couple of his friends had glimpsed him in the car, but he managed to pull back, and out of Trent's grasp, slide his sweat shorts and tank top back over his lithe body, giving his meat rack and fuckslab a small semblence of decency. Trent just shrugged and left him stewing, arms crossed against his beefy chest, thighs apart to give his thong encased ballbag some room, and ease pressure off his stuffed arse hole. It was a pyrrhic victory. Finally the car began to slow, near where some of the trashier rent boys hung out. Finally Trent found what he was looking for, a guy about the same height and build as Nico, wearing a pair of cutoff jean shorts and a low slung tank that read "fuckboy" across the chest, retro 80's style. Trent told the driver to stop. Nico got ready to bail out, clearly humiliated that he was being replaced by a male prostitute (since he still thought of his escort job as something more than just a fucktoy), but Trent pushed him back to the seat with a firm hand on his solar plexus, just as the door opened and the teen punk climbed in.
The teen punk was clearly familiar with Trent and climbed over Nico with barely a grunt, revealing his dense packed chest in the low slung neckline as he leaned across, and a seamy cumspattered skin. Nico was shocked - he was a model escort, with his preppy looks and rich clientele - and kept his fragile ego intact by pegging himself and his line of work above rent boy sluts. Sometimes the illusion was tenuous, when a john was rough fucking his hole and talking trash, but it was shattered now, being 'traded down' so easily. He found himself wedged between the two of them. Trent slammed the door closed and told the punk that Nico was about to leave, but first he had to give Trent back his thong and dong. The punk smiled evilly, and Nico's cheeks burned hot. Before he could react much, Trent and the punk each took his arms and slid them behind their shoulders, leading him powerless to participate.
Nick sat there dumbly as the punk slid his shorts down, bucking a little as his hands enveloped his straining dork. The silk thong followed, and soon his horsecock was bobbing in mid-air. The punk sat back, and with a nod from Trent, they slid his thighs as wide as the Transvaal, Trent fingering his nipple while planting a hot deep french kiss on his lips, while the punk toyed with his aching meat until it began to drip again. Trent broke the kiss long enough to tell the punk to "get the plug", and the kid began pushing on his stomach again, telling him to 'shit the fucker out'. Agonisingly, while he was still being frenched by Trent, Nico was forced to push the dong out, clenching his arse and grunting as the massive buttstuffer slowly worked its way out. But when it reached about four inches, the punks hand shifted, stopping the progress of the dong, and slowly, relentlessly forcing it back in. Nico couldn't speak, and Trent, still devouring his mouth, saw nothing, so he had to try and eject it all over again. The punk played this game a few times over before gripping the base and beginning to fuck the dong into Nico with long brutal thrusts. There was no mistaking what was happening now, but Trent didn't seem to care much, now fingering the punk and drawing his mouth in to kiss them both as the boy continued to ram the fake dick in and out of Nico's tender hole.
All the kissing and prostrate massaging was making Nico horny, and he was getting on the verge of cumming. Just as Nico began to groan, the load building in him, the punk kid sucked the dong out of his hole, letting it drop to the floor, and the two let go of his body, kissing each other inches from his face. He gasped and panted, his whole naked body glistening with sweat, his foreskin retracted and pearls of precum dripping down the shaft. But spread wide and naked, without skin on his body, he couldn't cum, and as the two continued to tonguefuck, his whole body heaved with the tingling feeling of being on the brink, but not quite cumming. Soon, his ballbag began to pulse and throb, sending a dull ache up his spine, his dick half drooping like a weight had been slung off the head. The two finally broke off their kiss, staring down at Nico. "Look at you, you horny slut" Trent snickered, "you might think you're straight and macho but your hungry hole is pussifying." As if to emphasise the point, the rent boy rubbed two fingers along his distended arse lips, before plunging them into the gaping hole. Nico gasped, the stimulation jerking his wet cock back in the air. It was true, his hole was getting more sensitive, but he flushed hot, angry at the idea that being fucked - being forced to fuck for money - was turning him into a pussy. Angry and frustrated, because he couldn't deny it either, naked and cock-crazy at having just been dildo fucked.
"Tell you what Nicky" Trent began, idly fingering his nipple again, keeping him on the edge of arousal. "Even though you've lost your thong and dong, I'll give you one last chance to make this date work. I mean I'd hate to go back to Penn telling him you were a lousy fuck. Nico's cheeks were red hot now. "No, like I said, I wanna take it slow, get to know you, really let a relationship blossom. Who knows, if I like you enough, we could be regular fuckbuddies..." Nick's heart sank at the thought, he just wanted the date over, but he knew better than to object. "So, you want to please me? Do you Nicky? I'll tell you what. Why don't you borrow this kid's clothes, and we can go out again, start afresh. How 'bout it?"
With the kid fingering his hole roughly while Trent spoke, and still throbbing and sweating like crazy, he had trouble focusing on Trents words, and only realised what Trent was asking of him at the end. He had to wear the punk rent boy trash clothes? And that was a favour? He cringed, and wanted to curl up in a ball. But there was no chance for that, especially not with the kid already pulling the tank top over his head as Trent spoke. There must've been a tacit agreement between the two of them to do this often, because the punk kid stripped to his ripped jock in a flash, and reaching over for Nico's sports bag before he could say anything. He knew the drill, pulling on Nico's expensive gymwear, and helping himself to the Nico's wallet while he rummaged around. Nico saw it all, and tried to protest, but Trent held a finger to his mouth when he first uttered a sound - all but shoving the digit over his tongue - and telling him actions spoke louder than words. His other hand was still pushing down on his chest, rendering him immobile, except his hands still slung on the set backs. Last, the kid grabbed his gym jock and thong, and jumped back out of the car with a whoop, while Trent handed him a couple of crisp hundred dollar bills.
The door slammed, leaving naked Nico and Trent together, and the car leapt forward, racing back through the streets. Trent pulled out his finger with a slurp, and Nico almost choked on his words as he told him how the kid had lifted his wallet. Trent shrugged indifferently, only saying he'd be docking him for the cost of his help. Now Nico was left not just naked, but with nothing to wear but the filthy trash the kid had left behind. Struggling to keep balance as the car swerved and turned, Nico struggled to pull on his clothes, while Trent idly told him how he owed him a favour for this second chance, while copping a feel of his tackle and arse as he wormed around. The kid had narrower hips than Nico, and he had wider shoulders - in fact a much bigger rack, so he quickly discovered it was impossible to get the clothes to fit him. The jean shorts barely pulled over his arsecrack, the fly impossible to button over his horsecock and balls, especially inflated and distended as they were. The tank hugged his body, the thin arm straps cutting into his chest, exposing his nipples and most of his sleeve and body tattoo. The waist clung to his abs, pulling the hem up above his belly button. It was completely obscene, not the gear of an escort, but a fully fledged male hooker. Finally sick of his twisting and pulling, Trent leaned in, shoving his hard cock down with a painful thrust, so it stretched out the right leg of the shorts. His ballbag was mashed between his thighs, and his cockroot and bush still showed between the unbuttoned fly. The car jerked to a halt, back outside the club where they'd been not an hour before. If anything, the crowd was thicker now, people almost touching the windows of the car. "Okay rosebud, now are you ready?"
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