So, I’m seriously shook up about this. About 6 months ago I was involved with an older guy. He was about 10 years older than my 24 year-old self. It was purely sexual, not really a relationship.

One night I wanted him to come over, but he was having poker night with a few of his friends. I made a joke saying “I wish I could be the prize”, to which he didn’t respond and I quickly forgot about it.

The next time he came over he asked me point blank if I was serious about being a “prize”. I told him I was joking, but that it was always a fantasy of mine to be with multiple guys at once. A few hours later, we’re in bed and he brings it up again, joking that I would have 6X the fun if I came to poker night. The comment and the look he gave me really turned me on and I responded, “Okay, set it up, but only if you think you can handle watching me fuck your friends.” That made it real and for the next couple of hours we talked about how we would do it. Then we fucked again, and afterwards decided we were both sort of uncomfortable with it for different reasons. For me it was the size of the group. Six guys is a lot of fun to fantasize about, but in reality I think it might be too many. For him it was insecurity. I guess he was worried about me being more attracted to his friends.

Anyway, we set some rules and boundaries and he arranged for 2 of his friends to come over one night and join us. I agreed to anonymity with his friends. Since we don’t know any of each others friends it was no big deal to me either way. As an extra twist I told him to give me little to no warning when they would arrive.

One night I was at his apartment, blindfolded and tied, which wasn’t an altogether unusual occurrence for us. He was being a huge tease and then just leaves me hanging for about 10 minutes without saying anything. When I heard their voices my heart began to pound. I was so nervous my whole body felt like it was on fire. They were slow to finally reach the bedroom, but when they did everything happened so fast. Tom was on me right away. I heard him unzip his jeans, he pulled back my hair, and fully entered me. “Here she is boys”. I let out a gasp and the room feel silent.

Now Tom was a filthy with pillow talk, which I loved. He would always say the most depraved things to me and sometimes really humiliate me. But when he started that in front of his friends it really hit different. While he was fully inside my pussy and grasping my hair he told me to say hello to his friends and welcome them to my body. I was still nervous obviously. My body had still burned with desire (and embarrassment) and words completely failed me. I hesitated and he slapped me hard on the ass, saying “don’t make me repeat myself”. That got a few whispers and hushed laughs from his friends. In the moment I forgot my directive and defaulted to “please fuck me sirs”, which must have been passable because with that Tom began to trust in and out. This provoked cheers from his friends.

We had been through quite a bit of foreplay before this experience and when his friends started to get vocal it really pushed me over the top. I could feel my pussy clenching and buildup to an intense orgasm already. Within a minute of him fucking me hard and deep like that he had me whimpering and moaning. In another minute he had brought me to a full orgasm. He stopped briefly and proclaimed that the slut had cum already. Then he slowly started back up again, and I felt new hands exploring my body. Before I knew it I was getting my nipples teased and giving head to his friends while Tom fucked me with increasing vigor.

I kept having to turn my head away to gasp for air and to let out my moans. Every time I did that I was given a hard slap on the ass and a fresh volley of verbal humiliation from Tom. After a few times his friends started to get more comfortable and joined in on some of the insults. So here I was, tied in doggy style while 3 of them took turns fucking me and calling me names. Honestly it was the hottest thing I’ll probably ever experience.

I had already cum twice on his cock by the time Tom pulled out and shot his cum along my back and ass. He was quickly replaced by his friend. With his friends at either end of me the dynamic was a lot different. They were both more aggressive with their thrusts, much more handsy, and frankly had bigger cocks than Tom. The first guy made me cum once before also leaving his cum on my ass. Then I was sucking Tom’s cock while his other friend had his turn. This cock felt bigger than the others in the best way possible. After he entered me the rest was just a haze. By the end of it the 4 of us were thoroughly spent and I had cum all over my ass and face from I think 5 different loads. Tom helped me to the shower where I cleaned up, and by the time I came out the mystery men were gone. It was an incredible experience and though I did wish we could do it again, Tom insisted this was a one time thing.

Anyway, that’s just some backstory. Last month I went home to visit family and my older brother was there. He’s like 8 years older and we’ve never been close. I hadn’t seen him at all since 2018. We got talking that night while having some drinks and he was telling me stories about his army buddies. He starts showing me pictures of a them all in Greece and Tom was in like all of them.

So apparently he’s like best friends with my brother for the last like 5 years. I managed to gather that my brother is one of the 5 poker buddies Tom had. I didn’t mention the dynamic between us, just that we had met.

Ever since this realization I can’t stop wondering if my brother was there that night.

Thinking back on it, when I replay it all in my head, one of the guys voices sounds like my brothers. But I didn’t notice it at the time, so is it all just in my head? Wouldn’t I have recognized it in the moment?

Also, behind a blindfold he would have seen my face. So if it was him he definitely would have recognized my face or voice and dipped right?

Maybe I’m overthinking, but I absolutely cannot shake the feeling that he was there and that Tom knew what was happening.