First time for everything.

[For the record, there are some spelling mistakes and grammar issues I'm sure, and I think I change tenses a couple times, but what the hell. Hope you enjoy]

For your pleasure

It had been months since I had been laid. I was sitting in a hotel room in Winnipeg, feeling bored and sexually frustrated. In an effort to amuse myself, I opened up craigslist on my laptop and went to “casual encounters”. I cruised some of the w4m posts, and responded to some of them, but wasn’t getting anywhere. I was feeling desperate. I could feel the bulge in my pants growing as I imagined meeting some sexy stranger and inviting her into my room. What would happen? What sort of things would we do? Would I have to take charge, or would the girl take control as soon as she walked through the door? I found myself looking at w4m posts that were weeks old, so it seemed as if I was out of luck. When I went back to the casual encounters menu, my eyes fell on the mw4m section. Hmm, that’s an interesting idea. I had fantasized about having threesomes before, but never seriously considered it. Not only had the situation never arose, but I never trusted myself in bringing the subject up with anyone I knew. The cursor hovered over the mw4m link, and then I clicked it.
There weren’t as many posts in this section, but the posts seemed to be genuine. Near the top of the list I noticed a post entitled “New to this…” Considering I was also new to this sort of thing, I opened the link. The post came from a couple in their early thirties, and basically they were looking for a guy that would be friendly and “chill” with them, as this was new territory for them and wanted everything to go well. The post also specified they wanted someone “open-minded”. There was a picture attached of a sexy dark haired girl in some bathroom mirror. There was that bulge again, swelling up and pressing itself against my jeans. I figured I fit all their requirements and so I responded to their post.
I had pretty much given up hope of getting any responses from my messages, and so I was surprised when I got a response no more than a minute later. It was from the mw4m post. They wanted to see a picture of me, and asked if I had ever done something like this before. I answered in kind, and before I knew it we decided on a time they would meet me at my hotel.
I was extremely nervous. What the hell was I getting myself into? My throat tightened, and so did the jeans around my crotch.
After a quick shower and a pep talk with the mirror, I got dressed and headed down to meet them. They were right on time. He had brought some beer. She wore a slim dress that wrapped itself around her waist and lightly fell short of her knees. Spaghetti straps over the shoulders covered with straight dark hair, high heels. Brief introductions, then we head to the elevator and go up to my room. The walk across the lobby and the wait for the elevator seemed longer than it was with the weight of people’s eyes on us—paranoia. Did they know?
My heart had been racing since our first email contact, but once we were in my room, sitting and talking, sharing a few bottles of beer, I began to calm down. They both seemed cool, and general conversation was easy. Tammy sat beside me on the loveseat, while John sat beside us on the armchair. This wasn’t so bad. We talked for about fifteen minutes before conversation lagged and things started getting awkward. John announced he was heading up to the smoking patio. Tammy and I stayed behind on the loveseat.
So you guys have never done this before? I ask, as I lean in and put my arm around her shoulders. Turns out they had tried once before. But as it happens, they had come to a similar roadblock the last time. Conversation lagged, things got awkward, nobody made any moves and nothing happened. Disaster she said. Well, I ask, do you think John would mind if we got started before him? She shrugged, and her eyes never left me. Without thinking about it I leaned in and kissed her on the lips. My hand slid down her thigh and up her dress. She kissed me passionately back while my fingers found her bare flesh at the top of her thighs. She’s warm, and moist. Do you want to go to the bedroom? I asked her. She said yes and stood up, running her hand up my leg and over my crotch, gently massaging it. We went into the bedroom and undressed each other. I laid her down on her back on the bed and leaned over her, my hands planted on either side of her, my engorged cock hovering between her legs. I kissed her down the neck and across her chest, slowly working my way down to her pelvis and then her thigh, less than an inch from her warm moist pussy.
I was on my knees at the side of the bed, my face buried between Tammy’s legs, my tongue swirling and probing, my lips sucking and maybe a finger or two sliding their way in and pulsating in the some form of hook. I heard the door open and close, and then John was standing in the bedroom door. Oohhh, he said, already shedding his clothes. Oh boy, I think, here we go. I’d never seen another man’s cock before, except maybe my father’s once when I was young, but nothing like this. The light was dim, but I could see John’s erection as he moved to the end of the bad, positioning himself toward Tammy’s head. I watch from between Tammy legs as she takes John’s penis in her hand and pulls it into her mouth. She moans and John sharply inhales through his teeth. Being a part of this is arousing me immensely at this point and I begin stroking my cock as I watch Tammy swallow cock. John looks down at me, You want in on this? he asks me. At first I don’t get it. Get in on what? I think to myself. But then John stands up and pulls Tammy to her feet, positions her between he and I, then pushes her to her knees. Tammy reaches up and coaxes us closer together by the tips of our cocks. I look over and see John’s cock, his shaft thick and strong, curved slightly upwards in Tammy’s hand. She takes him into her mouth and pulls my cock closer. Our cocks are almost touching as she pulls John’s out and swallows mine. I pull Tammy’s head down onto my cock until I feel her gag then pull out. She gasps, rhythmically stroking our cocks. Suddenly I feel John’s hand slide around my back and rest on my ass. I jump in surprise, but the hand remains, and I allow it. After a second or two it feels alright anyways. Tammy then takes our cocks and rubs their tips together. She moves in and licks them. John’s hand has slid between my cheeks and is moving for my balls. What the hell is this? And it feels good. What the hell I figure. In for a buck, in for a bundle. Before I know it John has moved to his knees with Tammy and they’re making out. Tammy’s hand is still stroking my cock, John’s hand is now massaging my balls and inner thighs, and I feel like I’m going to explode any second. NO! I think to myself, don’t blow this! Then, there it is, I knew it was coming, John leans forward from his knees and takes my cock from Tammy’s hand. I made eye contact with him, his dark eyes looking up from under sandy hair. His hand moved up and down my cock. It felt so strange to have another man touching me like this. And not altogether bad. His mouth was warm and full of saliva as it covered my cock. He moved up and down and swallowed deep, then pulled me out. He looked up and smiled at me, pre-cum and spit dripping from his lips, then I held him by the head and pulled him back onto me.
This was nuts. Now to be honest with you, it was during this swap the cock between the two of them, I blew my load. One thing I know for sure was that it was all over Tammy’s tits. She giggled, which was fine, and I fetched a towel. Tammy was lying on her back on the bed again when I came back with a towel and began cleaning her off. John was between her legs, vigorously eating her pussy as she moaned. That sheepish post-orgasm feeling lingered a while as I watched John move himself into Tammy. I watched, recharging so to speak, as John fucked Tammy. At first she had her legs wrapped around him as he fucked her over the side of the bed, but then she moved onto all fours on the bed, back curved, arching into her voluptuous ass and John mounted her from behind.
I’m starting to feel pretty good again, and the sight of Tammy and John on the bed is seriously turning me on. I see my opening and climb onto the bed, positioning myself on my knees in front of Tammy. Her head is bouncing as John fucks her from behind, but they slow down, and Tammy takes my cock into her mouth. I eventually get hard again, and John pulls out. Tammy moans and follows his cock with her ass as it slides away. I see her bite her lip. She’s into this big time. So am I for that matter. I think he wants to switch, so I get up and move past John who again, slides his hand along my side. As I move myself behind Tammy, running my hands up and down the insides of her thighs and rubbing her pussy, John positions himself on his back under Tammy. I notice his legs poking out beside Tammy’s. She moves herself over his engorged cock and teases it with her pussy. I’m not quite sure what to do now, so what the hell and I lean down and start eating Tammy’s ass. I spread her cheeks with my hands, my fingers stretching the skin, and ran my tongue around her asshole, doing my best to cover it with saliva. My toes are brushing John’s in this position, and his cock is very close to my face. Tammy’s still teasing him, gliding her pussy across his tip. I lick Tammy hole some more, then slowly push my index finger in. Her asshole is tight as first, and twitches. But then it loosens and I move my finger in and out. I wonder if they’ve done anal together before, I think. At this point, on impulse, I reached down and grabbed John’s cock. Tammy was still teasing him, and he felt rock hard. Strangely, after having John suck my cock, it didn’t feel as strange as I expected when I moved down and took his cock into my mouth. It felt huge in my mouth as I went up and down. John moaned and he and Tammy kissed. When I pulled John’s cock out of my mouth again, I held it and guided it into Tammy. She slowly slid down onto him and he reached up to her breasts.
I felt so dirty, what was I doing here? But it felt so good. So hedonistic and lustful. Sucking John’s cock seemed like a huge step when I thought about it later, but at the time it wasn’t a big deal. It was kinky and cool. I went back to Tammy’s ass as she moved slowly up and down on John. Tammy was laying on top of John at this point, so her ass was at the perfect angle. My tongue moved and tickled, and my finger now glided easy in and out of her hole. I was stroking my cock with my free hand, coaxing myself from chub to hard-on. When I was close, I positioned myself, in the tangle of legs, behind Tammy. I slapped my cock on her ass, then slid it up and down her crack, paying special attention to her asshole. My cock became fully hard again and I positioned the tip onto Tammy’s hole and rested it there. Everyone on board? I’m thinking. Looking for validation of my intentions and receiving none—I have a pretty good feeling everyone’s cool with that—I pushed her cheeks apart with my hands and began to slowly push my cock into her. I can feel John’s cock moving inside her, and notice he slows down to allow me in. I push some more, my rock hard cock first pressing against and then sliding through Tammy’s asshole. It feels amazing as her sphincter presses around my shaft like some sort of biological cock ring. I stop midway, pull out a little, and then slide my entire cock deep into her ass. I can feel John’s cock against mine as we move together inside her, filling her. Tammy’s soft moan rises higher and a little more desperate as we fuck her together. It feels amazing and, what? already? I feel myself once again approaching orgasm. Try to stop it, try to stop it, annndd….ugh, I pull out and convulse over Tammy, shooting cum across her back.
And the rest is history. John and Tammy fucked a little longer, and then finished. Everybody showered—separately unfortunately—then John and Tammy packed up and left. Judging from the pleasant good-byes and smiles on their faces, we all had a good time.
So. That’s my story. Hope you liked it! Maybe you can share one with me sometime.
The bi thing was crazy. But I don’t regret it.

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Posted by whatRtheodds87
11 months ago    Views: 3,888
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3 months ago
perfect except showering separately.
11 months ago
Helluva story, amigo. I've fantasized about practically everything you detailed. Lucky bastard!
11 months ago
Excellent story!!!! :-)
11 months ago
Sounds like a great time, been there done that and love it, bi sex with a couple is the best
11 months ago
Fucking fantastic! You can come be our third anytime you want. You are exactly what we need.