I accidentally [F]ucked [M]y best friend’s little sister

So I’ve known this girl longer than I’ve known my now best friend who we’ll call Jim. I actually met her back in a youthgroup when I was a sophmore and she was still in eighth grade. I guess I’ll call her Mary for this story… Even back then I kind of though she kind of had a crush on me. I’m not super attractive or anything but I had that generic skater haircut and girls digged that shit in the early 2000’s. Anyway, fastforward to my senior year in highschool and I had become quite good friends with her older brother and we’d hang out all of the time. At this point she had a boyfriend and we were just friendly. In highschool pretty much every guy and girl casually flirt I feel, so when we had little back and forths it was pretty normal in my experience. Mary was also very cute, was just the right amount of thicc and well endowed.

One day Mary invited me over to help her and her friends with their physics project to which I obliged. I was a good student and had helped her with school stuff here and there before. When I got there I quickly noticed that it was just her and another friend there, both wearing that mask stuff that girls wear for complexion or whatever. They kind of joked about how embarrassing it was and all of that so of course I had to tease them back. We kind of all just talked for a bit, nothing about the physics project came up for a while until I dropped a comment about it. Mary quickly explained to me that their other project partners flaked outright and now they just wanted to hang out. Didn’t bother me. That’s when Mary brought up the idea of them putting a mask on me. Obviously I declined, very adamantly, towards the idea. She teased me and tried to convince me about how good it would be for my skin but I declined. She kind of let it go but would jokingly try to sneak up on me with the shit. Not too long after that her friend left and I started to feel a little awkward, hadn’t noticed that neither Jim or their dad was home. We were just sitting in her room watching dumb and dumber, alone.

For a while I didn’t say anything and I was kind of just watching the movie, then it happened. She jumped on my back with a container of the goopy shit and started trying to put it on my face. I stood up quickly and she fell off, but she got some on my face. Of course this was unacceptable so I smeared it off and rubbed it on her arm. At this point I’m kind of in a bad battle position. See, her bed was right behind me and she had a disjointed hit box in the form of whatever tool girls use to put that on their face. She comes at me and again goes for the face, or that’s what I thought. She just tackled me onto the bed and straddled me. I was fighting off her hand with one arm and trying to push her off with the other. Which, by the way, was really stressful because she had big ass tits and it was hard to aim my hand in a safe area. She kind of just let her self fall and my hand slipped off her shoulder. At this point she was just laying on top of me laughing into my shoulder. After a few seconds of giggling it kind of just stopped and I thought about the situation, and started to notice her tits pressed up on my chest like WOW never dated a girl as endowed as she was so I was actually pretty turned on at that moment.

She started to push her self up a little but was looking down at me, don’t think she had the mask stuff in her hand anymore but I didn’t really care at the time. I definitely had a boner, like 100 percent full mast and I’m pretty sure she could feel it. She kind of just giggled and went in for the kiss. That was it, we made out for like 15 minutes and were dry humping the shit out of each other. I wasn’t exactly a virgin but I’d never been turned on like this before, still haven’t to be honest. Eventually we just kind of fucked. It was awesome, and I’m still great friends with her brother. We don’t talk about it, I’ve never brought it up since and neither has she. I even accidentally sent her a dick pic a few years back that was intended for my GF who was away for college. Was less awkward than it could have been so that’s good. It’s worth noting that her and the guy she was dating at the time are still together and I still feel like a bit of an asshole everytime I see him.

Source: reddit.com/r/gonewildstories/comments/bn91r6/i_accidentally_fucked_my_best_friends_little