Playing with Friends

Things don't always work out like you plan.

I met Jessica through my friend Des. They'd dated for almost a year, but wound up breaking it off. They remained friends, though, and still did a lot of things together. One night he asked if I could pick her up from a concert and give her a lift home as he was going to crash at a friend's house afterwards. I did, and we hit things off, had a great time together, and soon found our way into each other's beds on a regular basis.

I came out to her early on because I was starting to accept my own sexual preferences and I figured she had the right to know since she was obviously part of those preferences. Thing is, you never know how someone is going to react when you tell them you're bi.

She took it very well, as in it made no difference to her. Looking back, it shouldn't have surprised me. Like I said, free spirit. I'd learn more about her own proclivities later, but she was the first girlfriend I ever had where we could both ogle hot guys and I'd feel no sense of shame about it. We both kind of grew into it and soon we found ourselves not only ogling, but talking.

A gorgeous dude would wander by our table at the food court, we'd discuss what we'd do with him. The hows, the whys, and the planning would eventually work their magic and we'd have to find convenient places to relieve our worked up sexual frustrations! It was wonderful, but it couldn't really last for long.

Jessica and I stayed close even after the relationship didn't work out. It was just one of those things where we knew we were going different directions to begin with, so there was no way we're going to end up in the same place. Nevertheless, we maintained a "friends with benefits" relationship because, let's face it, we both enjoyed each other's company both in and out of bed.

I wasn't in a hurry for a new relationship. After all, I had a fantastic woman who called on me regularly for very personal favours. A few months later, I learned about Des's bisexuality. I was shocked! I'd known this guy for years and he never seemed the type. He always had a girlfriend and we'd talk at length about the finer points of pleasing women. One day, while chatting online, he just opens up. He'd been on a short trip to visit a friend in Seattle. I knew that. What I wasn't aware of was that he'd not only visited, but slept with, his friend. It went okay, and they planned to play some more later, but it wasn't a relationship more than a fun time in the bigger city.

Since I had nothing to lose, I came out to him. He wasn't shocked, as I was, but he was surprised. Weirdly, he'd had a sort of, I don't know, "feeling" about me. I confessed another thing to him, something I'd only told Jessica.

Sure, I'm bi, but up to then, I'd not had any experience with a guy. I wanted to, but no takers. There was a pause on the chat for a few minutes and he finally typed out "Well, I think you're kinda cute...." I smiled and invited him over for the afternoon and we wound up in bed together soon after. In some ways, being with Des was much better than my first time with Jessica as I'd learned some control and she'd taught me a few tricks that I could contribute.

Granted, mad, passionate sex with a guy is a hell of a lot different than with a girl, but things managed to work out pretty well. We were both kind of nervous about telling Jessica about our relationship, but figured that we should. Des broke it to her before I did, and she was cool with it, far cooler than we thought she might be. I guess it never occurred to us that some women had certain things in common with guys. In other words, most guys like to watch two ladies get it on, some ladies like to watch two guys go at it. Made sense, if we'd bothered to think about it.

As it happened, we all were hanging out one night in my basement. Des and Jessica were both over that night to watch some movies. I think we were digging on a Monty Python something or other. I'd pirated a massive cache of that stuff from the library since I went there on a pretty regular basis. Dubbing tapes was my second foray into the wonderful world of piracy just after cracking software on the Commodore 64. It always overjoyed me when I figured something out, and it made me just as happy that I could have my own copies of Monty Python's Flying Circus!

In between bouts of laughing our asses off, I noticed Des and Jessica getting kind of friendly. Nothing serious, just her rubbing her hand up and down his thigh and him occasionally running his fingers through her hair. I've never been the jealous type and Des and I were never an official "thing" anyway. I'd watched more than a my fair share of pornography by this point in my life and I knew that I would love to watch two people having sex. After a couple of episodes, she was sitting on his lap and I'd moved from my chair to share the couch with them.

In the middle of a sketch, I glanced over and saw Des's hand under Jessica's t-shirt, lightly rubbing her bare back. As things were building up to the Python's big punchline, I looked them over and said "Look, dude, if you're gonna feel her up on my couch, have the common courtesy to take her shirt off!" I meant it as a joke, but apparently Jessica took it as a challenge. She whisked her shirt off with a small giggle and remained on Des's lap, her top covered only by a simple white and pink bra.

I'm not sure the look I had on my face when she did that. I would like to think it was a mixture of pleasant surprise and utter shock! Not one to pass up an opportunity, Des kept stroking her back and added some light kissing along her ribs and her nearest arm. I eased back against the armrest of the couch and took in the scene. Here were two good friends of mine, who coincidentally shared their bodies with me, and they were getting pretty intimate as I watched. It dawned on me that they had shared themselves with each other too. Each of us knew what the other was like in bed, there were no secrets. As my thoughts passed through my mind, I arose from my seat and joined them; Des sitting down, Jessica on his lap, and me kneeling on the floor in front of them.

The great comedian Bill Hicks had a fantastic rant on how people should fuck artists. Artists are uninhibited, that's why they're artists. Artists are very much into life, sensation, sensuality, and spontaneity. So maybe it wasn't too much of a surprise that a musician/illustrator, a designer/sculptor, and an illustrator/poet might find something sensual and arousing to pass the evening.

Des continued to lightly kiss Jessica's arms and side while I caressed and kissed her other side. I felt one of her hands in my hair, and I became slightly bolder, nipping at the small of her back. I wasn't sure how to handle Des, what with Jessica around. For all I knew, she was just being nice about watching two males. All I knew is that I wanted to touch Des and I figured she wasn't going to freak out too badly since she had her eyes closed most of the time. I ran my hand up his thigh and nibbled at the little parts of her side that spilled over the waistband of her jeans. Des's hand found mine and we linked, holding each other for a moment before I stood up, shut off the TV, and turned on the radio. I remember thinking about putting on a CD or something, but that would've taken time to find, figure out, and all that. I wanted to get back to my friends.

Apparently, Des had gotten a little bolder himself and I lightly kicked Jessica's bra off the floor and into a corner as I returned to them. She had turned to better face him and he was licking and sucking on one of her pert nipples. Jessica has marvelous breasts graced with large aureole and sensitive nipples. She arched her back into his mouth and a soft gasp escaped her lips. Joining in, I supported her back with one hand while cupping her other breast and drawing the nipple between my lips. She audibly moaned at that and her hands grabbed our heads, both pulling us closer and bracing herself against us. She pulled Des away first and kissed him, her tongue mating with his moments before turning to kiss me. I was already fully aroused, but I wasn't in any hurry.

Meanwhile, Des unbuttoned her pants and his hands cupped her ample buttcheeks, flesh on flesh. Jessica giggled a little and moved a little so he had better access. I trailed my fingers down his arms, kissing her body as I again sank to my knees. Des's jeans bulged and I knew that he had to be getting a little uncomfortable there. When she'd moved, Jessica had basically shifted to sitting on one of his legs, so with a furtive glance at both of them, I ran my hands along the waist of Des's jeans and unbuttoned them, easing down the zipper and finding that delightfully hard cock just throbbing under all of that pressure. Des smiled and wiggled a little so I could better get a handle on things. Jessica turned around, saw what I was doing, and sat there, almost transfixed. I don't know why I doubted her, because the look in her eyes as I stroked my friend belied almost animal hunger.

"Callan?" she said, her voice just barely above a whisper. "When you two, you know, when you um...," she stammered "When you two played, did you..."

I knew what she was asking, and I had a fair idea that she wanted to see something. I pulled at Des's pants and underwear, working them off a bit as best I could with her sitting on his leg. She stood up and I slid everything off, leaving him sitting on my couch, naked from the waist down. Jessica pulled her pants off as well, leaving her wearing only her panties. As she returned to the couch, I positioned myself between Des's legs, kissing him from his nipples, to his chest, to his tummy before finally going down on his beautiful, thick cock. Both of them gasped in quite delightful ways as I sucked on him. My tongue swirled around the head of his shaft before taking him as deep as I could. He moaned and his head fell back, inhaling and closing his eyes as I pleasured him. I loved the feel of him inside me, so intimate and so taboo, especially in my home town.

Jessica watched, entranced as I pulled him from my mouth, licked the length, and then took him again while I cupped his balls. As his pleasure built, he grabbed my hair and gently met my downward rhythm with upward movements. I love to watch my lover as I give them pleasure and while Des's eyes were closed, Jessica's fingers were inside her panties, touching and rubbing and I wanted to taste her too.

I sat her down next to Des and she quickly shed her underwear. I'd eaten her like this before and she knew what was coming. I pulled off my clothes and decided to try something new, since I didn't want to leave anyone out. Lifting one of her legs over my shoulders I kissed her pussy, licking around the lips and taking in a heady scent of desire. I kept one hand on Des and did my best to massage and stroke him as I tasted her. It was amazing, and my senses whirled. Des and Jessica were kissing each other while I pleasured both of them. I brought Jessica close, but not quite to the edge. I wanted one more thing.

Kissing her thighs I stood up, pulling on their hands and leading them to one of the bedrooms. It had a full size bed in it, along with a nightstand containing a few condoms I'd picked up from Planned Parenthood. I knew one of them was just a standard, lubricated without the spermicide, type of thing. I pulled it out, opened it, and handed it to Des. By this time, I was totally without inhibitions, and I grabbed him by his long hair, pulled his head back and kissed him, then his neck, and then his ears. He groaned a little at the sensations and then I kissed Jessica, nipping at her sensitive earlobes and blowing slightly in her ears.

I looked at Des again and said, "I want you to fuck her. I want you to fuck her from behind while I eat her." Turning again to Jessica, "Pretty lady, I want you on all fours, on top of me, and I want to make you quiver." She smiled, nodded, and I laid down on my back while she took her spot above me. Des slid the protection down his length and eased into her, filling her in one slow, smooth stroke. She groaned loudly enough that, for a minute, I was worried she'd wake my parents upstairs. He began to move, we all did. I had an amazing view as he worked his hips, riding her. As he fucked her, soft yet strong, my mouth closed over her clit, flicking it with my tongue and gently sucking it. Jessica groaned and then, to my surprise, found a way to cover the sounds.

See, I was so busy being involved, I hadn't thought of myself. I was too busy having a good time. But when Jessica's warm mouth enveloped my own throbbing erection, I remembered that there were three of us here, and we finally found a great rhythm. Jessica worked me while I licked her while Des's hips sped up. My own moans and sighs joined theirs. Occasionally Des pulled out, to calm himself and make things last. Before sliding into her again, I'd take him, tasting her desire on his.

We couldn't have been going at this for long. Jessica soon started to shudder, and her arms gave out, bring her to rest on top of me. I could feel that Des was probably getting close. He makes these awesome little grunts as he nears orgasm and his movements belied his proximity to the edge. Jessica, no longer making any noises louder than gasps, came on me and Des, releasing her pleasure and grinding herself into both of us. I knew Des wouldn't last much longer and, wetting my fingers from Jessica's desire I stroked and clutched at his sexy ass, working the tip of a finger inside. "Oh fucking Christ," was all he could say before a final thrust deep into Jessica and then almost literally quacking as he came, shooting hard and fast like he'd done with me, on me, and in me a few times before. It was a sensation I knew pretty well, and I envied Jessica getting to feel that right now.

Still hard, Jessica moved off of me. I figured I'd have to finish myself, and didn't mind it a bit, but they had other plans. Flushed, Jessica stroked me while I laid back against the headboard. Meanwhile, Des watched for a bit and then dug through the nightstand drawer. I wasn't sure what he had in mind, and I didn't care all that much after Jessica again took me in her mouth. I knew from experience that my friends could roll from one orgasm onto the next, and it wasn't a huge surprise that they weren't quite done. Des disappeared for a few minutes to "clean up and be right back." My eyes closed, I felt closer to satiating my own desires when I felt Jessica's lips disappear to be replaced by strong hands rolling protection down my shaft.

Using some KY, Des stroked me, covering me in the clear, slick gel. I wasn't sure how long I'd last with what he had in mind, but I didn't care. I wanted him and I wanted Jessica to watch me fuck my boyfriend. Apparently he did too and gently lowered himself down onto me. God he felt amazing, and after he accustomed himself to the sensation of being filled, he rocked against me. My hands grabbed his hips and I guided the motions as best I could. For a man who'd just had a shuddering orgasm, he rode me as if it was his first experience of the night. Jessica laid on her side, smiling as her two friends enjoyed each other. I kissed his nipples, licking and nibbling each one. He sped up, and I met him with every stroke. I'd made love to both of these people before. We'd had experiences that were soft, romantic, and very sultry. But now? Now I wanted to fuck him and fuck him hard. I stopped him for a moment and put him on his back, taking the lead and driving deep inside as he grunted with my thrusts. I felt myself drawing closer. I have no idea how long this lasted, maybe five minutes? Maybe twenty?

Either way, I rolled up to the brink, and when I came it was amazing. Rocking against Des and shaking uncontrollably, I finally collapsed on top of him, breathless and completely satisfied. We cleaned up and fell asleep together in that bed, talking and caressing. We had other encounters, both with each other and all three together, but the first time was fantastic in its own right. I felt more alive from that moment on, not only because I'd had some incredible sex with two great friends, but because I felt vindicated. Everything I thought about myself was pretty close to the truth. I knew I was bi, and while I didn't need this kind of experience to prove it to myself once and for all, it certainly cemented the idea in my mind.