My First Threesome

I've been lucky enough to have been involved in two different threesomes over the years. Both instances involved a woman and another guy, rather than two women, my as yet unrealized goal. Interestingly, they both occurred within a single year.

This one involved a guy I'd known since high school (Tom) and an attractive woman who worked in the same office as me (Jan). Tom had always managed to attract his share of girls (and frankly some of my share too), but I didn't hold that against him. Over the years we talked freely about our 'exploits,' which is when we admitted that neither of us had ever been in a threesome. When I mentioned to him I had slept with Jan on several previous occasions and got the very clear sense that she would be interested in a threesome, Tom and I just looked at each other and said, 'let's go for it with Jan.'

It took a couple of days before the three of us were free on the same night. We went to a restaurant for a drink and settled in to one of their curved booths, with Tom and I on either side of Jan. Since I had already mentioned our little plan to Jan, we started in with some flirtatious banter, which soon became quite explicit once the drinking began in earnest.

Though we were sitting in a booth, there were a number of tables across from us at which some couples and guys were sitting and eating. The tables didn't have a tablecloth, so anything happening under the table was visible to anyone who looked our way. Knowing that Jan was quite the exhibitionist, I took the opportunity to slide my right hand into her lap and up the slit of her dress. Jan knew I was also turned on by her flashing other people, so she wore a wrap-around dress, held together with a belt, which meant it wasn't hard to find a way in. I guess she knew where I was headed as Jan turned to me, gave me a 'nasty' smile, and then continued on talking with Tom. I put my hand on her inner thigh and pulled her leg toward me just enough to spread her legs so that the folks sitting at the tables could see up her dress.

I had managed to do all of this without Tom noticing, but after a couple of minutes Jan managed to direct his attention to her lap. Seeing my hand on her thigh, he used his left hand to pull her other leg apart. So there we were: Jan's legs were wide apart and Tom and I had our hands on her upper thighs. Jan just kept drinking and laughing loudly which had the effect of getting the people opposite us to turn and look in our direction. It was almost as if she dared them to look up skirt. I noticed one or two of the guys looking and checking her out. Since we seemed to be putting on a show, I moved my hand up her leg, pushed aside her panties and put a finger inside her already very wet pussy. Well, I guess she felt I went too far, because she growled, turned and gave me a 'stop that right now' look, which I did. Her shout, of course, managed to draw the attention any other diners who hadn't already gotten a good view of her parted legs and her panties.

At that point Jan announced she wanted to go now, so I thought I had ruined all of our plans. I apologized for my actions, but she said forget it. The real reason she wanted to go was that all our playing around had made her so horny that she wanted to fuck the two of us ASAP. Well, Tom quickly paid the check and we drove back to Jan's apartment.

Even before we got into her apartment, Tom and I took turns kissing Jan and running our hands all over her body. By the time we got into her bedroom, we had removed her dress, leaving her naked, except for a pair of sheer (and by now wet) panties. We all got on the bed with Jan on her back as Tom positioned himself between her legs and began to pull down her panties. I continued kissing her, massaging her breasts and sucking on her hard nipples.

Tom didn't waste a moment and buried his tongue in her wet cunt as her moans began to fill the room. With her red lips forming a big 'O' I took the opportunity to pull off my pants, straddle her chest and place my hard dick in her mouth. Although her moans continued, the sound took a decidedly different tone as I began to fuck her face. It was as though she understood what Tom and I wanted, which was, a woman who enjoyed being the center of attention, but was also comfortable in her role as our 'play thing.'

After a little while, Tom and I exchanged positions. As we were getting 'into place,' we briefly shared some comments about Jan's various holes that we had just been using. Her only response was to ask when one of us was going to fuck her.

Knowing this question was bound to come up, Tom and I had previously agreed to play a round of 'rock, paper, scissors' to determine who would be first. So with Jan lying naked on the bed and Tom and I on our knees with our rock hard cocks stretched out before us, we quickly played the best of 2 out of 3 games. Sadly (for me), Tom won, and while I watched, proceeded to sink his cock deep into her. I watched them fuck for a couple of minutes and then decided that the only thing that could bring all of us closer together was if I fucked her in the ass. So, I asked Tom to flip over on his back so that Jan was on top of him, which gave me the opportunity to pull apart her ass cheeks. She was exceedingly wet by now, as was the bedspread, so I slowly, but firmly, began to push the head of my cock into her asshole. At first she made a sound that resembled a squeal of pleasure (though it could also have been cry of pain.) I was prepared to stop, of course, but she began to shout 'fuck my ass, fuck my ass,' so I continued to drive my cock deeper into her. I had done anal only a few times before, so I was very excited about getting a 'green light' from her.

Though it took some effort from Tom and myself, we were eventually able to sync up our thrusts, so that I could feel Tom's dick in her pussy as I pumped into her ass. As Jan was pretty horny to begin with, and I knew from previous experience she didn't take long to orgasm, I wasn't surprised when her moaning became rhythmic and her body began to convulse. It was all Tom and I could do to simply stay in her as she twisted and shook as she came.

Once Jan calmed down and caught her breath, I could hear that Tom was getting close to cuming. Given the tightness of her asshole, I was also nearly ready. Tom and I had earlier agreed that we wanted to simultaneously cum in her, so I yelled out to him that I'm ready to cum. He responded that he was also ready, while Jan announced this was the first double penetration she had ever done and was extremely excited to have us shoot our jizz into her. Well, if we weren't ready before, Jan's comment just pushed us both over the edge as we exploded in her.

Between our grunts of pleasure and the twitching of our bodies, it took a couple of minutes till Tom and I regained full consciousness. The three of us understood we had just experienced something very special. Though we did manage to hook up several other times (both as a threesome, as well as each of us with Jan alone), in none of these instances were we able to regain the electricity that we all felt that first time.