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This was a long time ago (I was in my mid-20s). I was freshly divorced, and while not out on the prowl by any means, I was looking to start dating again. To this point I had only had sexual relations with my husband, who was my high school sweetheart. I really had no idea what I was doing, or what I was looking for, but I was introduced to a gentleman by a mutual friend. He was in the service, and seemed like a pretty good guy.
He took me out to dinner. I was modestly dressed in a nice springy dress and heels. He was dressed in slacks and a button down shirt. We had a nice dinner and some good conversation, though in the end it didn't seem like we had too much in common. That's ok though, I was able to get out and enjoy someone else's company...
He asked me back to his place for a drink, and though I didn't think we really had a spark, I said yes. I had no expectations of anything happening, just a drink and to hang out a bit. When we got to his place, there were 4 other guys hanging out. Apparently he has 2 roommates, and they had a couple of friends over. A bit awkward, but I didn't think much of it.
He offered me a glass of wine and we sat around talking. Soon enough we were doing shots, and the conversation turned a bit sexual. I was uncomfortable, but not scared or anything. I just didn't have that much to offer in the conversation, having not had much sexual experience outside my controlling husband.
They were talking about their sexual conquests, what they've done in the past, etc... It was interesting and eye opening to me, so I was intrigued. Then one of them started asking me questions, what my favorite sexual things to do were, what I've done in the past, fantasies, etc.. I really had no answers for them, so I kept my responses short. I told them I'd had sex, given blow jobs (which I HATED to do up to that point, because my ex was always very forceful with me, and ever reciprocated), pretty vanilla stuff.
One of them asked if I had ever had a threesome or more, or a gangbang. I laughed and shook my head absolutely not! It hadn't even crossed my mind! They all exchanged looks, and in my buzzed state I didn't really get where this was going, but then my "date" asked if I'd wanted to. I asked if I wanted to what? He responded "you know, us" as he motioned around to the other guys. I was shocked, and a bit numb, but oddly enough what came out of my mouth was not "no". I guess between my buzzed state, and the fact that I decided then and there I deserved some more sexual experiences, I blurted out "I guess".
Well it didn't take more than that for them to jump into it. My date came over to me and started kissing me first on my lips and then all over my face, neck, and started moving down my chest. Another guy came over and started fondling my breasts and another came over and started rubbing my ass. Someone started unzipping my dress from behind and pulling it down, and I surprisingly let them. My mind kept saying I should stop and leave, but I was also starting to get really horny, and wanted to see where this would go.
They stood me up and finished removing my dress. I stood there in my bra and panties. (I almost never wear a bra anymore now, but back then it was just supposed to be a dinner date, so I dressed a bit more conservatively).
One guy then started undoing my bra from the back, while another kneeled down and pulled my panties down to my ankles, and then lifted each foot up and removed them completely. There I stood completely naked in front of 5 strange men. I was definitely nervous, but also VERY turned on. Having lived a pretty sheltered life to this point, the fact that 5 men stood in front of me were eye fucking me had me feeling desired, if not a bit depraved.
I was sort of trying to cover my chest and crotch area with my hands, but it was obviously no use, so I just let my hands drop by my side. My nipples were so erect they ached, and I felt my pussy becoming wet. Was I actually about to let this happen?
While I was thinking through all of this, they sort of all just started closing in, one kissing me again, one started fondling and sucking one tit, another guy the other tit. The guy on his knees started rubbing and fingering me. And the other was behind me rubbing his clothed cock against my ass.
I'd go into more detail, but it all became a jumbled blur. Hands and lips were all over me, changing positions and angles. I tried kissing and grabbing back, but I was a bit overwhelmed. I started getting weak in the knees, and said so. On queue they led me to someone's bedroom.
I sat down on the bed, and someone gently pushed me down into a laying position. I had only then noticed that they were in the process of undressing. Suddenly 5 naked guys were standing around me, all 5 cocks standing at attention, and smiles on their faces. I had a moment of sheer panic. What the hell was I doing? How was I about to take on 5 guys when I barely knew what to do with 1???
I didn't really have time to process it much though, as all of them once again were surrounding me. One guy put his cock right near my face, and without thinking I just opened my mouth and took him in. I'll admit, back then I'm sure my BJ skills were a bit lacking, but he did most of the work, thrusting in and out. I was just a vessel, mouth open. 2 other guys were kneeling on either side of me, and the each grabbed one of my hands and wrapped them around their cocks. I started stroking then slowly. I was aware that another guy was starting to spread my legs. I was also very aware that 1) my legs were shaking, and 2) I was VERY wet. I didn't resist, I let him spread my legs, and then the next thing I know his stiff cock was entering me.
This was the first time another cock besides my husband's had ever been in me. And it felt GOOD! He started thrusting, and I completely lost concentration on the other cocks I had been previously paying attention to. My mouth was still open, taking another cock in, but I was no longer actively doing anything else with it, and I stopped stroking the other cocks and was just holding them (I know there were 5 guys, and I'm only accounting for 4. I'm honestly not sure what the other guy was doing, or if they were all just taking turns. I just lost track).
Like I said, it all became a big blur. I'm pretty sure all 5 guys had fucked me at some point, and I'm also pretty sure I had all 5 guys in my mouth at some point. I never sat up, turned over, etc... I was in the missionary position the whole time, them all taking turns on me. There was cum on my chest, and at one point someone came near my face, and whether it was on purpose or maybe I turned my head, I ended up with cum in one of my ears. That I didn't enjoy!
I have no idea how much time passed, but when they were finally done I was a mess. I had cum everywhere, my hair and makeup was a mess, my pussy was SORE, and at that moment I felt a combination of horror and satisfaction. It was strange, I felt like someone who did a terrible thing, but at the same time I felt a bit empowered. They had all left the room and were cleaning up and getting dressed. I took some time to wash up as best I could, and get dressed myself. I never did find my panties, they just disappeared. Maybe one of them took them as a trophy? Maybe they just got tangled in the bed sheets? I have no idea.
When I finally got myself together and gathered enough courage to join them back in the living room, they were all having drinks and watching TV again. I told them I was going to head out now. They asked if I was sure I didn't want to stay, and I told them I had to get going, as I had a babysitter waiting. They all wished me a good night, and my "date" said he would call me. As you can probably guess, he never did. But, I never reached out to him again either. It was just one of those things, it happened and I enjoyed myself, but I felt very little and used, and had no desire to see him or them again.
It wasn't until years later my husband and I were talking about sex, and sexual exploits. He knew I had sort of a sheltered past, but I told him I did have a few stories. I took a deep breath and told him this one. I was expecting him to be mad or grossed out or taken aback, or something. Instead he told me how hot that sounded, and why I never told him before. LOL I said I had no idea what your reaction would be! It turned him on hugely. We had sex that night, and he me had me recount this story to him while we were fucking. It was intense. And I no longer felt shameful or guilty about it. He still asks me to retell this story (and a couple of others) to him from time to time, and every time the sex during or afterwards is incredible!
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