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My First Threesome

My first threesome

I always knew that I was attracted to both men and women. Even coming from a small, conservative town it never made me feel odd or uncomfortable. But my first experiences, starting at around 18, were with men. So how do you find yourself involved in any group activities at such a young age? This is how it started with me.

My boyfriend Shane at that time had a lot of older male friends, many of them firefighters or police officers. He was the "unofficial" photographer for them so he spent a lot of time with them, and so did I. One afternoon we were at one of his friend's house, just hanging out. This guy named Brian was probably in his late 20s. Being in our late teens, my boyfriend and I were always horny. Brian was in the kitchen for a while, and Shane and I were making out on the couch when Brian walked back in. We didn't notice him at first so I don't know how long he was watching us. We had our clothes on, but it was getting pretty heated.

When I happened to open my eyes, I saw Brian watching us over Shane's shoulder. Knowing that he was just standing there looking turned me on even more. That was the beginning of my exhibitionistic side. I became more daring, reaching down to stroke Shane's cock through his jeans. I'm not sure if Shane just sensed something or what, but he turned his head and saw his friend. He was just leaning against the door rubbing his own dick through his clothes. I didn't really give it any conscious thought. I just stood up and took off my clothes.

The boy and the man looked at me in awe, not because I was model beautiful, but because they were so turned on by the ease with which I transitioned into a fully sexual woman, confident in my own skin. I looked at Shane, and he shook his head yes so I went over to Brian. Sliding against him, I moved his hand to my ass, wrapped my arms around his neck, and brought his face down to kiss me. We just stood there for a while. None of us was probably sure what was happening. But it certainly didn't feel wrong, at least not to me.

Things then moved quickly. While standing with Brian and helping him remove his clothes, I looked back to see Shane getting undressed. I caressed Brian's chest, his nipples, his ass. I cupped his balls and wrapped my fist around his cock, feeling how hard he was. I dropped to my knees and licked his shaft from base to tip, taking him deep into my mouth and sucking. He let out a groan. This continued for a while, and when I stood up I turned to see Shane lying on the couch masturbating while watching us.

While I had had a few one one one encounters with boys, this was the first "older" man I was with. Holding his cock in my hands, I felt powerful and very turned on. I felt like I figuratively held all of the power in the room. I was still young and exploring, with my experience coming from boys my own age who were just so happy to have any type of sex that they didn't really know how to express what they wanted. This was a man with some experience and was happy to tell and show me how he liked to be touched and licked and stroked and sucked. I had no idea until that point that I could be so aroused knowing someone was watching me. And seeing Shane stroking his own cock while watching me made me feel even more seductively powerful and aroused.

By unspoken agreement the three of us moved to the bedroom. It was the first threesome for all of us, so we didn't know what we were "supposed" to do, just what we wanted to do. I had no experience with homosexual or bisexual men at this time, but they didn't appear to have any interest in each other at all. That was probably good because I might have freaked out a little at so many new things at one time. I just knew that I did feel completely comfortable with the two of them. We kind of eased our way into it with one man on either side of me licking and sucking my tits. I just laid there for a while and enjoyed the sensations. One of them moved down to lick my pussy, but I honestly don't remember which one.

What I do know is that when I next opened my eyes, Brian was between my legs with his cock, looking at Shane for permission. Slowly at first he started fucking me, and it was wonderful feeling the difference between their cocks and their bodies. Shane was still a lanky teenager, but Brian had a man's body and the confidence to take what he wanted. It didn't take long for Brian to come, and right after he pulled out Shane slid in. I had already come once and, between my juices and Brian's, I was dripping. Apparently watching me being fucked had turned Shane on even more, so he came rather quickly. My body was humming.

Until this point I didn't know that I could have more than one orgasm at a time. But with the two of them working on me together, I was in a constant state of stimulation, knowing that the slightest touch could make me come again and again. I loved the possibilities that now lay before me and wanted to explore more and more.

That was pretty much the extent of it. The sex was missionary style, and while three people were involved, there wasn't much three-way action going on. For example, I didn't get fucked while sucking the other's dick. There was sex and voyeurism and exhibitionism and masturbation. Not really unexpected behavior for a first time, and I enjoyed it all immensely as did the guys. And this was the first of many times among the three of us. But I'm going to save those stories for another book when I write about my first few years learning about my sexual awakening in terms of multiple partners, women and men. It was never a lifestyle choice or decision for me. It was just a series of enjoyable experiences that led me to want to experience and experiment more.