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Chapter 256 by JoeSte91 JoeSte91

Does Trent stay? Or walk away?

Gavin Gets Fucked for Real

“Fine,” Trent agreed with a sigh. He gestured towards Gavin. “I let this guy experiment with my cock-”

“If you’re going to fuck him, you may as well call him by his name,” Chloe interjected, smiling to herself that a guy was willing to fuck another guy just to get a shot at her. Hannah had been right. The power of a beautiful woman was a marvelous thing. “Gavin. His name is Gavin.”

“Alright, Gavin does what he wants, and then I…” He looked Chloe up and down and licked his lips. “…I get to do whatever I want with you.”

Chloe nodded. “So long as you’ve done it with Gavin. For instance, if Gavin got on his knees and started touching your cock.”

His red-headed best friend shot him a look, and he realized immediately she was talking to him as much as Trent. Sliding out of the bed, losing the duvet so that he was once again naked, he crawled down onto the floor, shuffling on his knees until he was in front of Trent. The black footballer player looked even larger from down on the floor, his legs shoulder width apart and his thick dark cock softly bobbing just above Gavin’s head. Tentatively, he reached up and wrapped a single hand around Trent’s shaft.

He heard the black teen suck in air at the other boy’s touch. Looking up, Gavin saw the conflicted look in his eyes. Gavin was still unsure himself. In his head, he’d told himself that touching another man’s cock wouldn’t be much different than touching his own. Just attached to a different body. But it was different. It was warm, like chocolate melted from being left in the sun, but stiff and veiny with ridges and dimples that weren’t on his own. It was like he knew where his nose was on his own face instinctively, and he knew his own cock without even looking. But the member in front of him was completely foreign, and when he touched it, he had no idea whether he was doing it right or wrong.

“And see, because Gavin is on his knees, touching you cock, I’m obligated to do the same,” Chloe insisted as she dropped to the floor beside Gavin and placed her own hand alongside his.

Trent gasped as he looked at the boy and girl kneeling before him, two hands on his cock delicately stroking his shaft. “This is so weird.”

His cock throbbed in their hands. Chloe giggled and looked to Gavin, “He says that, but I think he likes it.”

“It’s probably all you,” Gavin said, then dropping his voice to a whisper, added, “I have no idea what I’m doing.”

“Just follow my lead,” Chloe said, as she tightened her grip as she moved her hand up and down, pulling the foreskin back and forth over the shaft.

Below her hand, Gavin mimicked her movement with her own. The method was unfamiliar to him. He’d jacked off enough to have practically perfected the technique. But the angle and perspective was all different, and the cock twitched and throbbed in ways that his own didn’t. It was thicker and longer too, his hand barely able to wrap around the girth and requiring much fuller strokes to cover the length of the shaft. In unison, they pumped their hands up and down his cock, Trent groaning above at the dueling sensations of Chloe’s smaller softer hand verses Gavin’s rougher, wider palm.

Chloe looked at Gavin, catching his eye as she pumped her hand upwards and stayed there, focusing on the head with smaller strokes. Still watching him, she leaned in and parted her lips, allowing her tongue to slide out and make contact with Trent’s warm, hard cock. Her eyes was all the instruction he needed, bringing his hand up as Chloe removed hers, allowing Gavin’s solitary hand to tease Trent’s glans alone. He brought his own head low and opened his mouth, before giving the black teen’s cock a quick lick. It felt hot and rough, and tasted salty, like sweat, but surprisingly it wasn’t as off-putting as Gavin imagined. He licked again, following Chloe’s example, trailing his tongue from the root up along the full length of his shaft.

Together they moved up his cock, slathering it with their saliva until his erect, throbbing member glistened in the light. Without even thinking, or being prompted from Chloe, Gavin lowered his hand, gripping instead at the base, and their tongues began to lap around the sensitive ridges of his helmet. Trent sucked in a breathe as he watched the two tongues on the head of his cock, trying to forget that one belonged to another man as their tongues met. The friends leaned closer, tongues moving over Trent’s cockhead and into each other’s mouths as their lips met, their mouths kissing around Trent’s engorged cockhead.

“Oooooh, shit,” Trent groaned, throwing back his head, the double suction of the two mouths sending a shot of pleasure along his length.

Slowly Chloe drew away, leaving Gavin’s mouth suckling alone on Trent’s fat, round head. He was aware that Chloe had gone but he continued to suck on the tip of the cock, even though a blowjob hadn’t been mentioned in the deal. But, as Gavin saw it, if this beast was to fit in his ass, it would be better to make it easier for himself, and if that meant lubricating it with his mouth then so be it. On another level though, sucking on the cock was kind of pleasant. The warmth in his mouth, feeling it twitch and throb against his tongue with every action, and that strangely addictive salty taste. He could feel Trent’s cock dribbling pre-cum onto his mouth and he couldn’t help feel a sense of satisfaction that he was turning Trent on.

“Fuck it’s so weird,” Trent said, looking down at Gavin’s face as the boy glanced up, either eyes meeting. “Every time I think this feels good, I look down and see a dude and get weirded out all over again.”

“I may have a solution for that,” Chloe offered as she pointed to the bed. “Lie down.”

Gavin let Trent’s cock slip from his mouth with a wet pop, as the black teen strode over to the bed. He sat down with his legs over the edge and then leaned back, until he was fully supine. Meanwhile, Chloe crawled onto the bed too, and threw a leg over Trent’s face, shifting so that her steaming, wet box was directly above him. She took his cock in her hand and stroked it, lathering his skin with Gavin’s slobber.

“See, now you can’t tell…” she wrapped her lips around his cockhead and gently bobbed her head for a moment. “…who…” She sank her mouth down on his cock, almost half way down his thick, long shaft before she gagged. “…is sucking your cock.”

Trent groaned as she went back to simply pumping his cock in her hand, while her eyes motioned for Gavin to continue the blowjob. The bespectacled white teen shuffled in between Trent’s wide, muscled legs, and brought his mouth back to the thick black cock and rose up in the middle. Chloe’s hand continued to massage his shaft, as Gavin parted his lips and allowed the bulbous head to fill his mouth again. He had no idea how girls managed this. His jaw was aching already. Chloe had even went half way down on his cock. He’d watched her do it before on his own cock, but watching her do it to another, a thicker, longer cock, really was impressive.

He tried to copy his redheaded friend, **** almost instantly, his mouth bubbling forth with even more slobber for Trent’s meat. Chloe spread it all over the thick, black cock, giggling to herself at how Gavin had tried to take as much of the cock as she had. Determined, he went back, sucking and slurping on the cock as he **** his mouth back down, half way on the cock. He tried to suppress his gag reflex, but it was untrained and instead he just lost control, spewing spittle all over Trent’s stomach and thighs as he pulled his mouth from the cock.

“Deepthroating might be a little advanced. Especially on a cock this size,” Chloe chuckled, sitting upright and placing her palms on Trent’s lower abdomen. “Perhaps we should move to the main-ah-aha-aaaaha.”

Chloe looked down over her shoulder at the large, black hands gripping her ass, as she felt a tongue beneath tickle her lips, pushing between them to taste the sweet honey inside. She gasped and moaned as she felt him pull her pussy closer to his mouth, sending erotic shivers up her body. Her muscles tingled as a warmth spread throughout, making her feel sweaty and feverish.

“Oh, fuck,” Chloe moaned, bowing her head. “This isn’t part of the…” she spoke in half-finished sentences, gasping between each thought and panting throughout. “N-not that I mind…” she looked back at Gavin. “So long as you don’t neglect…” her eyes rolled back suddenly as her mouth lolled open, winded by a sudden burst of pleasure. “G-go on.”

Gavin was startled, realizing she was talking to him now. He looked between Chloe and the cock, wondering if she was going to get off to let Trent fuck him, but she didn’t move. She simply sat on his face, rolling her hips against his lips and chin as Trent’s thick, wide tongue pushed inside her hole. When Gavin still didn’t move, even though it was clear that Chloe had no intention of separating that tongue from her pussy just yet, she said, “Go on…get on top.”

“You…want me…to ride him?” Gavin reiterated, going bugged eyed as he looked at the throbbing, thick cock, and tried to imagine sitting on it.

“Sure. You’ll be in-ah- complete control of how much-hm-of his cock you take,” Chloe explained, amidst moans. “And I dunno about you, but I quite enjoy bouncing on a nice, hard cock.”

She bounced her ass on Trent’s face to emphasize her point, chuckling at how she could feel Trent’s tongue slide in and out. The idea of the redhead bouncing on a dick brought back memories to Gavin of his best friend bouncing on his cock that fateful morning…the very incident that had set his break-up with Victoria in motion. She had really seemed to enjoy it.

Swallowing to settle his nerves, Gavin clambered onto the bed with Chloe and Trent and threw a leg over the black teen’s lower body. The actions themselves were strange enough, but nothing was weirder than pushing back with his ass and feeling a hard, warm, fleshy rod-shape poke his cheek. He leaned forward, pushing his face into Chloe’s full, heavy breasts, swaying as her body gently shook with pleasure. Pushing out his ass, he did what any girl would do in this situation, he reached back and took hold of the cock poking him and lined it up with his asshole.

Steadying the cock in one hand, he pushed back gently with his hips, until the cockhead met his hole. Just the contact made Trent gasp, the breath on Chloe’s pussy causing a ripple effect that had her moaning too. Given the pounding he’d already taken from Chloe’s strapless strap-on his ass was already sufficiently prepped and stretched to take Trent’s tip. With just a little extra ****, Gavin was able to lean back, burying the head inside his ass. He paused with just that much inside him, partly to allow his body to acclimate to the object entering him and also to evaluate what he’d just done.

A cock was inside him. For the first time in his life, Gavin, a self-proclaimed straight man, had a real, warm, living dick inside his ass. It was nothing like the strapless strap-on, just as he’d expected. And yet the heat, the thickness, the veins pulsing with blood; it was all so much more vivid than he’d expected. The heat spread throughout his ass, and made his own cock throb, and Gavin was surprised to realize that he had barely even thought of his own cock this whole time. As unexpected and foreign as the member inside his ass was, he felt enthralled and intoxicated by it. Would taking more feel better or worse?

Before the question had even entered his mind, he was already pushing back, sliding his ass another inch down Trent’s shaft. He lifted his hips and pressed down again, taking another inch, gasping at how it felt to be filled by a real, live cock. He repeated the motion, closing his eyes to relax as another inch slipped inside. Over and over, inch by inch, Gavin pushed down on Trent’s cock, determined to take the whole thing inside his ass.

“Fuck, your ass is even tighter than Ashley’s,” Trent growled, prying his mouth from Chloe’s pussy as the tightness around his shaft became overwhelmingly distracting.

“You fucked Ashley’s ass?” Gavin breathed out as he sat on another inch.

“Just before I came here,” Trent told him, his hands instinctively rising to Gavin’s waist and pulling him down, pushing another inch inside. “But, fuck I only thought I knew what tight was. There’s no doubt this is your first time.”

“First time with a real cock,” Chloe corrected, slightly irritated her own pleasure had been halted to talk about Ashley’s ass. “Buuuuuut…I may have a way for you to lubricate his ass and for us to settle our part of the deal.”

“I’m listening,” Trent said from underneath her.

She looked to Gavin for confirmation, and he nodded. “I’ll follow your lead.”

“OK then, first of all, get on your hands and knees,” she instructed, pointing to the edge of the bed, as she lifted her leg off Trent. “And you stand up.”

The men complied, though not quite immediately. I took a moment for Gavin to lift himself off Trent’s cock, even though he’d only taken it about half-way. But the thickness burned his muscles if he tried to move too fast. So, just as he’d taken it, inch by inch, Gavin relieved himself of the cock until, eventually, it slipped free with a small pop. Moving gingerly, he took his position at the edge of the bed, on all fours, his ass pointing outwards, still gaping slightly. Behind him, Trent stood, cock in hand, looking at the other man’s ass where he was soon to insert his dick.

“Brace yourself,” she told Gavin as she swung her leg over him and lowered herself onto his back, her large breasts pressed flat against him. She giggled and whispered in his ear, “am I heavy?”

“Not really. It’s kind of nice actually,” he replied, smiling although she couldn’t see it. “Kinda feels like we’re spooning.”

“Yeah, this is more like stacking,” Chloe chuckled again, before letting out a breathless moan as she felt her gaping, drooling puss spreading around Trent’s cockhead. She looked over her shoulder at the broad, black teen guiding his cock into her, a hand on her ass. “Someone’s eager.”

“Sorry, but I didn’t need any further instruction,” Trent smirked as he felt Chloe’s lower lips grip around his head. Snug inside her, he took his hand away from his shaft and began using his hips to push his cock in and out of her wet hole.

“Mmmm, yeah, fuck me,” Chloe cooed, still looking over her shoulder at him, eyes twinkling. “Fuck us!”

Trent pushed forward until his thick black cock was completely inside Chloe, his balls resting on Gavin’s ass just below. Already her soaked and wanting hole was leaking fluids around wide O-shape her lips had been stretched into. With two hands on her hips, he pulled back until his cockhead began to emerge from her hole, and then shoved it back in again in a single, hard stroke, his ball slapping lewdly against Gavin. Chloe moaned into Gavin’s shoulder, his own cock twitching as he felt her being fucked atop him.

The cock sawed into Chloe’s wetness, squelching nosily along with the slaps of his balls against Gavin’s ass as Trent found his rhythm, fucking the redhead in earnest now, faster and harder, seemingly in time with Chloe’s crescendo of moans. Just as she raised her voice, half gasping for air, half screaming out, expecting the cock to plumb her depths once more, Trent pulled out and angled his cock downwards. Chloe whimpered at the emptiness, feeling herself dripping onto her friend below. Covered in Chloe’s natural lubrication, straight from the source, Trent pointed his cock at Gavin’s anus.

Despite already being well worked over, the rim still offered some resistance. Gavin relaxed, groaning as Chloe nibbled on his ear, while Trent pushed forward, with a little more pressure until, abruptly, his hole widened and Trent’s wide, mushroomed head sank inside the other man’s asshole. He pushed in, and pulled out, only having gone the depth of a couple inches, and returned to Chloe’s pussy, which he slammed into at full ****. She gasped and moaned and resoaked his cock, which was exactly what he wanted. He withdrew and stuck it back in Gavin, driving in another inch.

This was how Trent wound up balls deep inside Gavin Westher. He alternated, fucking Chloe with full, long strokes, coating his cock in her wetness, and then pushing into Gavin’s ass with smaller, slower thrusts, gradually, bit by bit, giving Gavin a bit more and a bit more, until finally his black cock was buried in the white boy’s ass. He brought his hand to Chloe’s mound and rubbed her lips, as, gently, he began to slide his cock back and forth inside Gavin’s ass. Just as he had done with Chloe, Trent built up to a comfortable rhythm, deeper, with full, long strokes, though still slow. Though he’d loosened up considerably, Gavin’s ass was still far too tight to fuck any faster.

“Ooooh, fuck,” Chloe moaned, rolling her hips back against Trent’s hand in time with the two men fucking beneath her.

The pitch and tone of her voice told Trent that the bountiful redhead was close to cumming. So, he pulled his cock from Gavin’s ass and, in one fluid motion, removed his hand and drove his cock back home inside Chloe’s warm, wet puss. She cried out, throwing her head back at the immense pleasure surging through her body at being filled again by that hard, black cock. He fucked her, rapidly pistoning his cock in and out of her body, listening as her moans rose with each thrust, bringing her closer and closer to climax.

“Ah, ah, ah,” she sang as her pussy was packed with Trent’s fat, black cock. “Ah, ah, I’m gonna cum, ah.”

The announcement wasn’t news to Trent. He’d fucked enough girls to know when they were on the edge. Even if her moans hadn’t been a dead giveaway, her twitching walls, spasming like crazy were the surest indicator that within moments Chloe was going to erupt. Less. Something about the situation of being fucked atop her best friend, knowing that cock had been in his ass and was going back there, that Trent had given them both pleasure, set Chloe off in seconds. Her body shook and shivered, writhing on Gavin as the tightness in her body was released and her senses were flooded with pure bliss. Her pussy gripped his cock, squeezing him as he pulled out, and after him poured out her juices. She squirted, gushing over Trent’s lower body and soaking Gavin’s ass below.

As Chloe continued to cum and spray her juices, Trent sunk his cock back in Gavin’s ass, now thoroughly lubricated with Chloe’s squirt. He drove in, all the way to the hilt, his whole length inside Gavin’s rectum, with a single stroke until his balls were pressed tight against the other man’s nutsack. Trent was able to fuck Gavin with ease now, slipping in and out of his ass with the same ferocity and power with which he’d fucked Chloe, listening to Gavin’s opened hole squelching and popping as Trent repeatedly emptied and filled it with rapid succession. Gavin groaned, his own cock throbbing every time he took Trent’s cock deep inside, as if it were hitting some hidden button deep within that sent tingles up his member.

Chloe’s orgasm subsided, leaving only tremors and contentedness. Slumping, her weight shifted, and she slipped off Gavin’s back on to the bed below. With heavy eyes she looked up, and was a little surprised to see the boys still going. Trent’s hands were on Gavin’s waist now, helping to pull him back on to his cock with every thrust. He didn’t seem to care that he was fucking a man anymore. Pleasure was all that mattered, and Trent was close to getting off. His contorted face and gritted teeth made that clear. But when she looked at Gavin’s bowed head, and his twitching cock dangling beneath his body, she could tell he was going to cum soon too.

“Ah, fuck…I…I think…I think I’m gonna cum,” Gavin declared, as he felt that familiar feeling of his load rising along his shaft, amazed that he was capable of ejaculating purely from anal penetration.

Watching his cock, Chloe gasped and smiled as she saw it become completely rigid, the head expanding. The slit at the tip of his cock opened, seconds before he loosed his first shot of white, creamy seed. Gavin’s body bucked, like he was retching, recoiling with every throb and pulse of his cock, firing off stream after stream of his load and leaving white streaks on Chloe’s duvet. The redhead considered sticking her head beneath his cock and letting him shoot it right into her mouth, but she was exhausted. She couldn’t even lift her head. So, she simply watched as Gavin came on her bed from the cock in his ass.

“Oh shit…this fucking ass…” Trent groaned as Gavin’s orgasm caused his ass to clamp around Trent’s thick black cock like a vice. And with every shot, Trent felt Gavin’s ass pulse around his shaft as if it were milking him, urging the cum from his balls. Unable to move even an inch in or out, Trent had **** but to blow his load deep inside Gavin’s ass. “Fuuuuuuck, man, I’m cumming too.”

Gavin didn’t need to be told. He felt Trent’s cock stiffen inside his ass and then sticky, wet warmth hit him deep within. Inside his ass was already strangely wet, but he knew it was cum by how molten it felt hitting his walls. His own cock twitched at the unusual, erotic feeling of knowing his ass could make another man climax, and drooled a few more drops of his seed, completely emptying his balls.

For a few moments, the men shuddered together, riding their orgasms until they died out. Gavin fell forward, face first onto the bed, while Trent stumbled back, lightheaded. The simultaneous motions caused Trent’s still semi-hard cock to slip from Gavin’s gaping hole with a wet pop, cum trickling out after. Gavin turned his head and looked at Chloe, his redheaded best friend resting beside him on the bed with a smile on her face, amused that it seemed she’d disappeared to the two men for several minutes.

“How was that?” Chloe reached out and stroked Gavin’s face. “Better than the toy?”

“Absolutely,” Gavin mumbled sleepily. “That…was amazing.”

Rest? Repeat? Or...

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