I been chatting with a few Redditors and the topic of "who's someone you had sex with that you really shouldn't of". I already shared how I passed my College level English. Now I thought to share another one. It happens almost 10 years ago so my memories are a bit fuzzy on the details.

After my ex and I (18 at the time) broke up, his brother, let's call him James, (24/25?) came to my place to apologize on behalf of the family (tldr my ex spreaded my nudes around the school when we broke up). He was trying his best to console me, helping me get rid of all my ex's stuff from my place.

We had a few drinks after and just talked about whatever. I always knew James had a thing for me. I was getting more drunk than he was. I started flirting with him really aggressively, throwing myself at him. I wanted to get back at my ex. I think I blurted out something like "I just want to get fucked". James was shocked and was a bit flustered, not sure what to do or say.

I put my hands on his crotch and he didn't say anything. I started to massage his bulge and he still didn't say anything, just looked back at me. It didn't take too long for me to pull his cock out of his shorts and into my mouth. Not sure the exact size but it was bigger than my ex's. I remember his hand was where my chest was and I felt it cupping and groping my one of my breasts under my tank top. I don't know how long I was blowing him. It could of been a few minutes or half an hour.

However long it was, James pulled my head off his lap and shot his cum all over my face. I remember sucking his cock again with his cum on my face, making sure I got every drop out. I think the reality of what happened hit him and he rushed out of my place with my ex's stuff, apologizing more on his way out.

We never saw each other again and didn't really text about what happened. I sent him a happy birthday text sometime after and he just replied with just thanks.