This is has way more of a background, a much longer and more complicated story than what I'm presenting but wanted to get a little off my chest (sorry if it's long):
My first and only three some occurred with my best friend and one of my exs, but we'll get there.
Our friendship goes way back but we always have had sexual undertones. The first time I saw him naked was in hs and another friend and I walked in on him jerking. We all joked about it later and throughout the rest of hs I 'accidentally' walked in on him changing or getting ready to shower – those type of things several times. I've shown off my cock to girls in front of him. Other then that, we never jerked together though it was always something of interest to me. Sex topics were something we always talked about often, but other than the mild and wild escapades, we never had contact or were naked at length together without girls present.
I admired his body which was a lot like mine but much more toned and muscular. White, shorter, athletic and brown hair. As far as dicks go, I'd say we match up both about 6-7 inches, I'm a bit thicker but his cock looks much larger than mine soft (or maybe thats just when I saw it lol). His cock head is a bit more pronounced.
He has much more sexual history than me; quite the fiend. In hs he said he was bi but now he is straight, perhaps more open if anything. I've seen (and heard) about many of women, even heard the audio on some sex during parties. Anyways, enough back story. Threesome.
My ex and I hadn't been split for long. She was/ is a bartender who usually shuts down the bar, often by herself. I visited her now and then and we have had a long sexual history together. She has a banging body with tits almost too big for her frame, they were always looking good and showing cleavage. That's how she makes her tips. This night was no different. A black low cut v neck and some short shorts. Tits extra plumped up perfect and round from her bra's support.
My friend and I went in for a late drink. Weekday. Neither of us had to work in the morning. And drink we did. The bar was empty the whole time we were there, just us and her. She drank on the job, so we got her to drink with us. She loves shots. Eventually bar close has come and gone. Doors were locked and we kept drinking.
I'm not sure where things kicked off, but most likely we were talking about her body and how big her boobs were. Probably something along the lines of coaxing her to undress some. She ended up topless and over by me. I encouraged her to feel my cock and slowly drop my pants, standing in the dim lit bar. We began to hook up, the make out, stroking and groping. My friend watched beaming from ear to ear. She had a bottle in her hand, so I got my friend to take a body shot off her.
I think he complemented my dick as she began to play with it, I said something to the nature of 'I know yours is just as big'. I got him to drop his pants, wanting to my ex to see. She isn't very slutty so she hasn't seen a lot of cock, other than porn. He grabbed my semi and said my cock was pretty thick. I grabbed his, something I'd been craving to try. It felt good, semi hard as well. We stroked each other a bit momentarily and then bot let go and turned our attention to her.
I told her to grab it, my friend still in disbelief that she was near naked and we got this far. He smiled and she grabbed his member, grabbing mine next and we both slowly stiffened up as she felt and stroked us. One of the best feelings in the world.
She started to blow me, now beyond hard. I enjoyed it immensely and she continued jerking him. His cock looked much bigger than I remembered. She stopped. "Blow him", I said; wanting to see her mouth wrap around his cock, hoping he'd blow a load all over her face and tits. I wanted to watch his make it's way down her face and chin, hopefully she'd collect some ropes on her chest too. This is a huge turn on for me so I would blow instantly if I hadn't by then. At first she didn't really want to do more than jerk him, but a few minutes later she went over to him and slowly sucked and worked his throbbing cock. He gave me a high five and we both enjoyed the view.
After about 20 minutes of the jerking and blowing between the two of us, I wanted to see if we could take it to the next level. I figured we were both clearly too drunk to cum from a bj. "Let's go to your place" I asked my friend, getting my ex to stand, "I really wanna fuck" as I smiled at her.
She seemed somewhat unsure, but we went there. It was closer than either of our place. From here it gets a bit hazy, but I know I got her naked and fucked her hard. She finally got into it more as I got her from behind. She sucked on him as he watched, more high fives. I flipped her over, attempting to give him a chance to fuck. We'd come this far I thought, why not. She wasn't having it, but continued licking and sucking him as she was now on her back. We continued to bone, I encouraged my friend to try and titty fuck her. He did, something he was clearly enjoying, at which point I'm pretty sure I finished while watching. She got up at this point and was ready to finish. I thanked her and walked her out, disappointed in the fact mostly he didn't finish. I've been craving to watch him blow and on her would have been so hot. Still an awesome night, but nothing happened after. We discussed for some time, agreed to tell no one, and then we went our separate ways.
Needless to say it was awkward for sometime. I saw him less and less. She had leaked what had happened to some of our friends. He told his gf who now hated me. A few months later him and I began to hang again. He told me we'd have to do it with his girl, especially if they broke up. (They have, but still waiting for that one lol). We've only talked about that night briefly a few time since then. Something that at first we avoided and now just doesnt really get brought up unless he's trying to crack a joke. He said most of it's hazy to him as he was so drunk.
Hopefully I'll have the courage to get the discussion rolling or better yet, we find a girl who's down to get freaky and pull that off lol
Well sorry for the length, hope you enjoy
Source: reddit.com/r/sexystories/comments/39oqf0/my_1st_3_sum
Good story, man! Was it real? :) I would love to enjoy a threesome like that with my Kitty.
Oh yeah 100%! I def wouldnt say no to that ;)