The Playmaker

Connors pounding became harder and faster as she licked the remaining cum off Tyler's shaft and balls. He stroked her hair, watching her lick. He reached beneath her and played with her nipples, twisting them between his fingers, sending waves of pleasure through her body.

"I think Connor's getting close now. Are you gonna come again before he does?" Tyler smirked. Nina just moaned in response. Every sensation felt so sharp, so much on the edge of something. Tyler shifted around, moving away from her face and reaching a hand underneath her to touch her clit. He wedged it between his index and middle fingers, rubbing it.

"Argh!" Nina let out a wordless cry as her body shook with another orgasm. Her channel grasped tightly around Conner's thrusting cock and he exclaimed too.

"Holy..." He was coming, his cock pulsing inside her, her body milking his orgasm, and it was more intense than anything Nina could remember from her past experiences. Conner slammed in hard and stayed there, his fingers digging into her hips so hard, she imagined there would be bruises there.

"Nina, have you ever had anal?" Tyler was asking, his hand still underneath her, lazily circling her throbbing clit. She breathed heavily, her eyes closed. She didn't answer him right away. Connor pulled out, moving away from her and she collapsed on the bed, on her back. "Ni-na," Tyler spoke in a sing-song, then ran his wet fingers over her lips, spreading her own moisture there. "Have you had a cock up your ass before?"

"Yes," she admitted on a sigh.

"Oh, Nina, you dirty girl, that's fantastic," Tyler was grinning next to her, his dimples showing. She had a boyfriend a few years back who was really into anal and convinced her to try it. He had always been really careful, took it slow, and used lube and she felt safe doing it with him. She still preferred it in her pussy rather than up her ass.

"I don't know," she wasn't exactly excited about doing this. She understood that this was not over yet, that Tyler wouldn't be satisfied with just the blowjob, that there would be more. She was starting to trust him with the idea that he didn't want to intentionally hurt her. But if both Tyler and Connor took turns with her ass in addition to her pussy, she just didn't think she could handle it.

"Oh, no no, you can't take that back, babe. I definitely need to fuck that tight little ass of yours." He nudged her shoulder. "Roll over." She gave him a defiant look, not moving. Connor stood in front of the bed, his hands on his hips, seemingly watching how this was going to play out. "Nina, I'm not just gonna ram you with my cock with no warning, I promise you. Look, I am not even that hard yet," he gestured at his partially erect penis. "Trust me."

****

Tyler was running the show and they were just the players in his game. So far, he seemed to be steering them in the direction of everyone having a good time and getting off, though he seemed to be coaching Nina a lot on what he wanted her to do. Connor watched them stare each other down until Tyler scooped Nina up and rolled her over onto her stomach. She was so small compared to the two of them. At work, dressed and in a professional situation, Nina was an average-sized woman. She wasn't exceptionally short nor exceedingly slight. But here, naked, between two guys, over six feet each, she seemed dwarfed by their size.

"I can't even reach you with my cock from over here, so just relax, seriously." Tyler stayed at her side, kneeling beside her. His hand went between your legs, dipping between her thighs. Connor came closer, watching. Tyler's fingers disappeared in Nina's pussy, rubbing along her seam. Connor could feel his cock stirring back to life at the thought of how hot and tight Nina was. It was almost a struggle to keep going for as long as he did without coming because every single thrust felt amazing. And watching her simultaneously suck Tyler's cock just made it more difficult to hold out. Watching has turned out to be way more arousing than Connor ever expected.

He watched now as Tyler drew his wet fingers from Nina's pussy back towards her asshole. He rubbed her own juices over that tight, puckered hole, adding pressure to penetrate her with his finger. Nina moaned, her eyes closed.

"Do you have lube?" Tyler turned and asked Connor.

"No," Connor replied quickly. He didn't usually fuck girls in the ass. And the few times that he had, it was at the woman's request, at her place.

"Do you have aloe?" Tyler was looking at Connor while his fingers continued to work on Nina.

"Like for sunburns?" Connor narrowed his eyes. Tyler confirmed. "There might be some in the bathroom."

"Can you throw on some pants and go get it?" Connor's eyes instinctively darted to Nina, to check whether she was ok with this happening. Hers were still closed, her bottom lip drawn in between her teeth. Tyler was still touching her while talking to him. "Trust me, she's gonna appreciate it. She won't want me to try to go in without it."

A wave of apprehension washed over Connor about leaving Nina alone with Tyler. But they were friends, right? They came together. She said she's known him for twelve years. She would be ok.

"Nina?" He wanted to check with her. She opened her eyes and nodded, avoiding looking him in the eye.

"Yeah, get it," she said in a soft voice.

Connor pulled on a pair of his pajama pants and a t-shirt before leaving the room. It was late, nearly two am, but there were still a few stragglers around. His other roommate, Ryan, sat on the sofa with his arm laid out along the back behind a woman he was talking to. Ryan's brother was still there, talking to Oswald about something in the kitchen. Connor tried to draw as little attention as possible as he went into the bathroom and searched through the medicine cabinet.

"What are you doing?" Os stood at the door, leaning in the door jam.

"Umm... just..." He saw the tube of the clear aloe gel then and grabbed it. "Getting something." He shut the cabinet and tried to step past Os in the doorway.

"What do you need that for?" Os furrowed his brow. Connor hesitated for just a moment on how to answer it.

"I will explain that to you later. Excuse me." He pushed past his roommate.

"Did you hook up with that girl you hijacked from me?" Connor was at his door already. He sighed.

"Yeah, I'm sorry man. She's a friend from work. Umm... we'll talk later." He went back into his room, making sure to lock it and test the handle.

He turned towards his bed taking in the scene playing out at the moment. It struck him how awkward he would have found stepping into this situation any other day, but right now, it seemed like the natural progression of things. Tyler was fucking Nina on his bed. There was a slight twinge of jealousy, something about how they were sharing some two-minute, private moment while Connor had had to share Nina all night. He reminded himself though that he'd already had sex with Nina and had come with his cock inside her.

Nina was on her knees, leaning forward on her elbows, bracing herself for the pounding Tyler was giving her. Her head hung down, her hair flipped forward, and he couldn't see her face. When he came closer he saw that Tyler had already gotten a finger into Nina and was carefully working it in and out, talking to her in a calm, quiet voice.

"Relax, you are too tense. Am I hurting you?"

"No," Nina shook her head.

"Are you gonna come for me again? Cause you feel fucking amazing. God..." Tyler looked over his shoulder at Connor. Connor offered out the tube and Tyler took it from him. "Thank you, much appreciated."

Connor watched him pull his finger out, squirt out aloe gel onto Nina's ass and onto two of his fingers and then gently work them into her in tandem. Nina moaned quietly and he continued to thrust his cock into her. She blew out a breath when his fingers penetrated the surface.

"Connor," Tyler called his attention away from Nina's ass and up to his face. "I'm gonna need you to lose the clothes and get on the bed."

Connor found himself following the direction without really knowing what Tyler had in mind next. His cock was at half-mast when he pulled his pajama pants back down and his t-shirt off. He sat down on the bed next to Nina, brushing her hair out of her face and peeking into it. She looked over at him, giving him a small smile.

"Are you ok?" He cupped her face in his hand and she leaned into it.

"Yeah," she bit her lip.

Connor leaned in underneath her to kiss her mouth, his hand on the back of her head, pulling her into the deep kiss. She moaned against his lips. Tyler pulled out and she collapsed into Connor's arms. They were lost in the kiss for a long moment before Tyler cleared his throat and they looked up at him.

"Ok, so here's the game plan, guys." Tyler was sitting up on his knees at the foot of the bed. "This is like the piece de resistance of this whole," who rolled his hands over each other "two guys and a girl combo. Connor's gonna go on his back, Nina's gonna ride his cock, and I'm gonna fuck Nina's ass. Nina, babe, this is gonna blow your mind." She looked nervous, biting her lip. Connor kissed her again, marveling at the electric quality of the sensation. "Suit up." Tyler threw a condom at him.

Nina reached over to grab the foil wrapper, giving him a tiny smile. She sat up at his side stroking his cock for a few moments before ripping open the packet and rolling the condom down over his cock. Her touch was amazing. He watched her small hand grasp his cock and move up and down his shaft and he hardly wanted it to stop. Of course, the sensation of her sliding down onto his cock was even better. The view of her breasts, with pink, pebbled nipples, her blond hair framing her face, those pale blue eyes connecting with his, suddenly made him realize how beautiful he found her.

Nina's hands rested on his chest as she began to ride him, moving along his shaft, grinding down into him. She was so wet and warm and tight that Connor almost forgot about the fact that they weren't alone. Tyler had sidled up behind Nina and he could feel him there. He pressed a hand to Nina's back pushing her down towards Connor's chest. She leaned forward, her breasts brushing against him. Connor took her nipples between his fingers, rolling them. Nina's eyes closed, soft whimpers escaped her lips. Tyler was back to fingering her ass and Nina looked like she was close to coming again. Her tongue kept flicking out over her bottom lip, her breathing was ragged, she moaned, grinding herself harder and deeper onto his cock.

"Yeah, that's it, good girl," Tyler encouraged her. Connor wondered if this is something he should pick up from this guy, whether it was actually a turn-on for Nina to be talked to this way. This has been an interesting experience in seeing what another guy does in real life, as opposed to in porn.

"Ah!" She screamed out, her body simultaneously jutting forward sharply and contracting all around him. She was coming, shuddering, pulsing against him and Tyler had taken that moment as the opportunity to enter her. She moaned louder now, her brow furrowed, her eyes still closed. He was going to hear it from Os about this tomorrow, about how it was one thing to steal a girl he was interested in and another to have loud, screaming sex with her into all hours of the night.

He could undoubtedly feel Tyler's cock now, as well as his balls, which was a bit disconcerting. He felt his movements and a bit of extra weight leaning into him.

"Holy fuck, Nina, you feel amazing. So fucking tight! God, I'm not going to last like this." Tyler moved slowly, carefully. Connor didn't move at all since Nina's latest orgasm, lying still beneath them, just taking in the sensation of the other two.

"Are you ok?" He reached up to brush Nina's hair back. He hadn't asked her this enough tonight. He was so caught off guard by this entire weirdass situation that he didn't think to ask.

"It's... just... so much," she breathed out.

Tyler pulled her hips back towards him, pulling her further onto Connor's cock as well and she screamed again, her body erupting with another orgasm.

"Holy. Fucking. Shit." Tyler grunted out, coming with her.

There was a momentary pause, a stillness between all of them before Tyler pulled out. Nina collapsed on top of Connor, her channel still pulsing around him, and he started pumping into her from below. She nuzzled her face into his neck, kissing him sucking gently beneath his jaw. Her breasts pressed into his chest, her nipples still so hard. Connor grasped the globes of her ass with both of his hands, holding on tightly, and within another minute he was coming again too. She moaned against his neck, her lips vibrating against his skin. Her weight felt so comforting on top of him that he didn't want to roll her off.

He pulled out carefully, without moving Nina off himself. Her face was still nuzzled into his neck, her breathing slowing. Her arms were wrapped under his arms and up over his shoulders, clinging to him. He stroked her hair, breathing her in.

"Nina, babe, do you want me to take you home?" Tyler was standing next to the bed, his pants already done up, pulling on his shirt. Nina didn't respond. Connor angled his head to peek into her face. Her eyes were closed, her lips slightly parted.

"I don't think she's awake," Connor told him. Tyler's expression spread into a smug grin. "It's fine. I'll take care of her."

"I'm sure you will, man." Tyler sat down in his desk chair putting his shoes back on. "This was fun. Hopefully, she's not gonna hate me for this in the morning."

"It's definitely not how I expected my night to go," Connor admitted. Tyler chuckled.

"I didn't exactly plan this either, honestly. But sometimes you just see this opportunity, you know, an opening, and you gotta make a move." Tyler stood up grabbing his jacket. "It was good to meet you. Cool party. Maybe I'll see you around." Tyler grinned big again.

"Yeah, you too," Connor told him from the bed, Holding onto Nina.

Tyler shot a finger gun in his direction before letting himself out.