Truth or Dare

He looked around for Tyler, wondering how he was processing the evening's developments and found him sitting over on his right next to Jackie. They looked to be having a casual conversation except for the fact that Jackie had her seven inch cock out and was playfully stroking it while they spoke.

"---Oh come on, you like pussy don't you?"

Tyler scoffed. "I'm seeing a sausage party here, there's not much pussy to go around."

Jackie rolled her eyes and reached her hand down underneath her balls. When it reached its destination she inhaled sharply and closed her eyes as she swirled her fingers around. She then opened them and looked into Tyler's eyes as she brought a finger up to his mouth, tracing his lips before sticking it inside.

"What's that taste like to you mister?" She smirked.

"Fuck." Tyler was in disbelief. "How is that even—"

Jackie laughed. "Don't ask questions. I've seen the way you've been looking at Amber all night and—" She looked over towards Amber on the sofa and caught her staring at Tyler. "—I've seen the way she looks at you. Why don't you go join them over there? I bet you she's super wet." Jackie then leaned in closer to whisper in his ear, "and I can say from experience that she has the tightest fucking cunt." When she pulled back away she was licking her lips and Tyler and Amber were staring deeply into each other's eyes.

As Tyler stood up and walked over to the party on the couch, Jackie turned to Gina and Chris. "So, what's going on over here? How was baby's first blowjob?" She grinned at him.

Chris blushed, and then turned to Gina. "Do you want to...?" Her attention was down towards his cock, still lightly running her hand up and down his cock which was now standing at attention out in the open, having been freed from his briefs.

Jackie laughed. "This oughta be good."

She smiled at him and licked her lips as she leaned in and gave him a kiss. "So here's the thing..." She paused, her hand freezing in place on his cock as she thought about how to finish her sentence. "I really like you Chris. I've actually had a crush on you for awhile now, and it makes me so happy to see you embracing us and our... condition."

"But?" Chris asked eagerly.

"I only top."

"What? What do you mean?"

Jackie chimed in, "It means she likes to fuck, not get fucked. How adventurous are you feeling tonight Chris?"

Gina quickly added, "But, we can just suck each other off if you'd like. You seemed to really get into giving that blowjob to Kira. And I would love to taste you..." She resumed lightly tracing her fingers up and down his cock.

Chris's mind was racing a mile a minute. When he asked he had it in mind that he would fuck her the way that Tyler was now drilling into Amber from behind. The idea of him taking Gina's cock in his ass hadn't even seemed a remote possibility to him. He looked down at it again. It was big. He had never had anything in his ass before, let alone something like that. But, all the same, he felt himself reaching a new level of arousal. The idea of experiencing the same explosion of cum in his ass as he had his mouth was hard to pass up. In a matter of seconds he did a complete 180 in his mind and the idea of not being fucked by Gina seemed a remote and ridiculous possibility.

"What do you think?" Gina was smiling a sweet smile at him, she seemed kind and loving. He found it hard to imagine her pounding him ruthlessly from behind, but couldn't wait to see it.

"I guess... I guess I'm a little curious to try it." He said, his lips curling into a shy grin.

"Holy shit." Jackie was in disbelief.

Gina's face lit up, he had never seen anyone so happy before. It was more cute than sexy, and for a moment Chris began to wonder what kind of future he might have with her. They hadn't even fucked yet but he already felt more intimacy with her than he had with any other girl before. She hopped up, her cock bouncing dangerously close to his face.

"I'll go get the lube. You stay right here." She then turned to Jackie and added, "Can you control yourself until I get back?"

Jackie just laughed.

Chris's heart thudded in his chest and felt as if it were about to burst. He wondered what he was getting himself into. As exciting and arousing as it had seemed just moments before he was now filled with anxiety. Even his cock had softened a little. He looked back to his left and saw Anna, whose face was now covered in Lexi's cum, almost grimacing and grasping onto the edge of the couch for dear life. She was completely at Amber's mercy. Amber on the other hand seemed to be having the time of her life, fucking Anna's cunt while Tyler fucked her pussy from behind.

"Just relax. You're going to love it." Jackie's voice was lower now, and almost soothing compared to her earlier teasing tone.

"How do you know?"

"Because I fucking love it."

"But it's different taking it in the ass isn't it?"

Jackie smirked. "No, I mean I fucking love taking it in the ass. And you're a guy, so it'll feel even better for you. Just relax and let her do her thing. She's really good. And, you can fuck me while she fucks you if you want." Chris could tell that was what Jackie wanted, and he wasn't going to deny her that pleasure.

"Ok, are you ready?" Gina was back, holding a large bottle. She didn't wait for a response before she squirted some on her hand and began rubbing it all over her cock.

Chris nodded, but he wasn't sure what to do. When Gina finished applying the lube she reached behind her back and with a simple pinch her bra fell off revealing her large round tits. She had small button nipples which had swelled to hard little knobs. Chris was looking at them, salivating when she looked up at him and saw him still sitting in the same position. "Turn over silly! It'll be easiest if you get on your hands and knees, and once we get going we can slide Jackie in. I assume that's why she's hovering over here, right?" She spoke with such a fun and playful voice, almost like they were setting up a board game, not about to have a threesome.

Chris had a million questions but he found it easier to just comply. He found himself feeling surprisingly submissive in her presence. He found that the hardest part of turning over was turning away from her. She was so beautiful, and he found her playful smile reassuring.

Facing the wall now he focused instead on her voice.

"I'm going to start with just a couple of fingers to loosen you up ok? Just try to relax, don't resist it. It might be a little uncomfortable at first, but I promise once we get going it will feel wonderful."

Chris could only nod, whatever words he thought to say got stuck in his throat.

He felt her hand slide over his lower back and down slowly making its way to his ass. When she got there she drew small circles over it with her wet finger before pushing gently inside him. He looked again over towards the girls to his right on the sofa and the the vigor and force with which Amber was fucking Anna and felt fortunate that Gina was the one to take his virginity. He was also surprised that there was no discomfort at all, in fact the further into him she pushed her finger the better it felt.

"Ok, I'm going to put a second finger in now. How are you doing?"

"Great!" He heard himself say, grinning. He couldn't wait to feel the rest of her.

Once her second digit was in she began slowly thrusting them in and out, circling them around as she did. Everytime she pressed them all the way in he felt an amazing, almost orgasmic feeling at the tip of his cock. Jackie was sitting just a few feet in front of him, stroking herself at the sight of his face contorting into shapes of ecstasy.

"Are you ready for me?"

"I think so." Chris remembered how it felt to take Kira in his mouth and how much bigger she felt than she looked and she was so much smaller than Gina. He realized that he was about to experience the same thing in his ass. "Fuck me, Gina. Fuck me hard." He almost didn't recognize his own voice saying the words.

He felt her hands grip his hips and then the wide heavy feeling of her cock pressing against his ass. There was just the slightest bit of pain before it gave way and she slid inside. The sensation of his ass stretching to receive her was intense, but euphoric. He had been staring at her cock for the past hour and it had looked big, but now it felt enormous. He was amazed that his body could even take it. As she pushed all the way into him he let out an involuntary moan.

"Oh my god Chris, you're so fucking tight." Gina moaned the words, and hearing them made every fiber in Chris's body want to please her.

The feeling of her filling his ass intensified the orgasmic sensations in his cock tenfold. It was like having a constant orgasm but without the release. As she pushed all the way back into him a second time the sensations were only amplified. He wanted to touch himself so bad, but couldn't as his arms were planted firmly on the floor supporting himself.

"How's it going? I can stop if you like."

"No!" He shouted. "Don't stop. Please."

Gina laughed. "Good boy." She began to pick up her pace. Starting to breathe heavier.

He turned his head all the way to the side trying to catch a glimpse of her but could only see her out of his peripheral vision. Even so, the vague image of her tits bouncing with each thrust was the hottest thing he'd ever seen.

"Jackie, you ready to join?"

Jackie beamed at Gina, not even sparing a second to look at Chris for permission. It became apparent to Chris that he wasn't going to really have much control of his body, it would be more like Gina was fucking the both of them simultaneously.

Gina slowed her thrusts, much to Chris's dismay. "Let's do it on the couch."

Jackie hopped up and ran over to the opposite end of the couch from the other girls where she sat down and lifted her legs into the air.

Gina leaned forward to whisper into Chris's ear. "I want you to go over there and fuck her pussy. Don't worry, I'll be right behind you."

Her words were enchanting. Chris felt compelled to obey. Not that he didn't find Jackie sexy, or that he didn't want to fuck her. But he never would have been able to bring himself to interrupt their fucking, no matter how brief, for anything on his own.

As she pulled out of him so that he could go over to her he felt a massive emptiness. He jumped up and ran over to her as quickly as he could, hoping that Gina would resume fucking him as soon as possible.

Gina lifted her legs and ass up high into the air giving Chris easy access to her cunt. It was completely smooth and beautiful underneath her balls. He pressed his cock up against it and found it easily slid into her wet pussy. She felt tighter than most girls and he wondered if her anatomy somehow compressed things. The sensation of his cock sliding in and out of her pussy felt better than any other girl he had fucked, yet still paled in comparison to the feeling of Gina in his ass.

It wasn't long before he felt her come up behind him and once again push herself inside his ass. This time she slid in easier without much effort at all. At the feeling of her inside him, he froze, unable to continue fucking Jackie on his own. Luckily Gina was more than happy to take over for him. She quickly resumed her earlier pace and with each thrust into Chris, Chris's body pushed forward thrusting into Jackie.

He was looking down over her body while they fucked. She had taken her bra off at some point while watching them. Her tits were small and round, and she had the tiniest nipples he had ever seen, but his attention was drawn lower by her cock which she pumped vigorously in her hand.

It seemed wrong to Chris that she should have to masterbate herself during sex so he reached down and took her in his hand and took over. Her hands in turn found their way to his ass and tried to accentuate the thrusts into her.

Chris felt as though he was in a perpetual orgasmic state. The pleasure he was feeling from each thrust already dwarfed any orgasm he had ever had before and the sensation was continuing to build inside him. He felt sexual pleasure radiating from his cock and ass out across his body to places he had never felt it before. Throbbing in his hands and feet, a tender sensuous feeling in his nipples, and even a warm sensation in his ears that felt vaguely sexual. He felt like if it continued to build he might explode. He yearned for release, while at the same time praying that he wouldn't come before Gina spilled her load in his ass.

It was odd to be stroking Jackie's cock, which in many ways felt like he was jacking himself off. It was right about where his would be if he were not plunged deep inside her, yet, of course he didn't feel the usual pleasure that came from stroking his own. It felt sexy and powerful in his hand. As these thoughts were running through his mind he heard Jackie grunt and felt a warm wetness explode over his belly. When he looked down he saw their bodies covered in Jackie's cum.

The sight of it, the feeling of it, the smell of it made him want Gina to come inside him more than ever.

"Come for me Gina, fill me up baby." He again barely recognized the timbre of his voice.

She only moaned in response.

"Fuck me harder!" He shouted.

She picked up her pace and Chris soon felt his body pass the point of no return. Seconds before his orgasm began he felt a warmth gush out of Gina's cock and shoot deep down inside him. It was an incredible sensation. With each burst he felt her cock swell and the euphoric gushing of cum filling his ass. He almost didn't notice his own cock start to come, he was so entranced by the feeling of Gina's coming in his ass. His attention was turned back to his own orgasm when he noticed just how long it had been going. He was used to an orgasm lasting a few seconds, but this time his cock continued to twitch and shoot load after load of cum into Jackie, seemingly lasting for almost an entire minute. With each one she let out a satisfied sigh.

When the final waves of pleasure finally concluded he collapsed down on top of Jackie, feeling her flaccid cock against his belly. He looked over to his right and saw that the other group had finished their romp as well. Sitting on the far end of the couch now was Kira who had returned and was stroking herself for round two. Chris looked over just in time to see her shoot cum all over her belly and tits.

"Thanks for the show. You guys really ought to come party with us more often." Kira said, exhaling heavily.

Chris felt a hand on his shoulder turning him over. Gina stood above him with a wide smile across her face. Down below her cock was still hard and dripping cum.

"Come here, you!" She said, taking his hand and pulling him up into a tight embrace. He felt their cocks press up against each other before she turned her head in and gave him a long deep kiss.

When she pulled away she smiled, "So, you down for dinner and a movie this weekend?"

Chris beamed. "Sounds great. But what are we doing afterwards?"

She reached down and clapped a hand on his ass. "I think you and I are going to have a lot of fun together."