Fair warning, I was an absolute douche bag in this story. I was young and dumb. Please know that I’ve matured and changed since then.
I had met Kelley the first day of freshmen year. I could tell immediately that she had a thing for me. The feeling was mutual, but I didn’t want to commit to her because there were about 3 other girls who I was interested in. Rather than tell her I was only interested in something casual, I lied and told her I wanted to get to know her before committing. In reality, I was only interested in sleeping with her. I spent the year stringing her along. Saying just give me more time, nows not a good time, I’m too busy etc. in reality I was talking to a few other girls and I wanted to keep the options open.
During the summer between freshman and sophomore year it all came to a head. She basically gave me an ultimatum, either we make it official or she moves on. Still being an ass, I told her goodbye then. A few days later, my best friend (at the time anyway) Mike, calls me and says that Kelley is interested in him. I knew she was only trying to make me jealous, but he was excited because she was the first girl to show interest in him. I know it sounds cliche but he was shy and hadn’t quite grown out of his awkward phase yet. I encouraged him to go forward with her and a few days later they started dating. She did her best to flaunt the relationship in front of me. Anytime me and mike we’re gonna hangout, she made sure to tag along and be extra lovey with him. If she couldn’t make it out with us, she’d blow up his phone and make sure I knew she was talking to him.
One day towards the end of the summer, mike was out of town visiting family. I was on the way home from football practice when Kelley texted me. She wanted to know if we could catch up. I called her after I got out of the shower and we started talking. She basically admitted that she wasn’t really into mike and hoped that it would make me jealous. I told her that I was sorry for the way things went between us, blah blah. A few minutes later, the conversation turned sexual. She told me that her and mike hadn’t done anything yet, because she wasn’t physically attracted to him. She also casually mentioned she was home alone until 7. She lived in the neighborhood next to mine so I decided to walk over. The whole walk there I thought about how wrong it was. And how I was betraying mike. But my judgement was clouded by the fact that I was finally gonna get to fuck her after a year of talking about it.
When I got to her house she was waiting on the front porch. Kelley was short, petite, short curly blonde hair and blue eyes. At the time I was in the best shape of my life from football. I was 5”11, rock solid shape from a year of football plus summer conditioning. She was wearing a white tank top and a knee length skirt. I hugged her and we went inside. We sat on the couch for a few minutes and started talking.
I honestly don’t remember what we were saying, but I do remember I leaned in and kissed her. She returned my kiss with her tongue lightly dancing around my mouth. I pulled her close and she took that as her cue to straddle me. She grabbed my face and pulled me in tight. I reached down and grabbed her ass and she started rocking back and forth, dry humping me as we make out. All of a sudden she stops, climbs off me and gets down on her knees in front of me. She un does my belt and pants and pulls out my dick. She goes right into the blow job, putting it in her mouth and bobbing her head up and down. Looking back on it, it was far from the best bj I’ve gotten but at the time, I was in heaven. She swirled her tongue around the head every few strokes and tried to deep throat. I put my hand on the back of her head and guided her down. After a few minutes she stood up, and pulled down the straps on her tank top, revealing her breast. I pulled her close to me and sucked on her nipple while I fondled the other. She started whimpering and rubbing my head as I went. I worked my hand under her skirt and pulled down her blue thong.
She straddled me again, her skirt hiked up around her waist wand lowered herself on to my dick. She starts rocking herself back and forth, taking my cock with each movement. Her breast are bouncing in my face as she goes. I suck on the right nipple as she grinds hard on my dick. I grab her bare ass and move her hips for her even faster. She’s moaning loud digging her nails into my back as she’s riding me. After a few minutes she turns around and rides me reverse cowgirl. She bounces up and down and I grab her hips and pull her into me hard. I knew I was getting ready to cum soon so I wanted to try one last position before I did. I tell her to bend over and she nods. She stood up, undressed herself completely and bent over. Until this day no girl has ever done this and I think it’s so hot. Rather than brace herself against the wall or the couch, she bent over and grabbed her own ankles. I entered her from behind and basically controlled her body for her. I pump in and out of her as hard as I could. At this point she’s so loud that her dogs started barking. I tell her that I’m about to cum and she turns around and takes me into her mouth. She sucks men hard and swirls her tongue with every movement. I shoot my load and she runs off to the bathroom to spit me out.
She comes back out and sits next to me on the couch. We talk for a few minutes but then her phone rings. It’s Mike. We share a look, knowing what we just did was wrong. I tell her I should leave and let them talk. Funny thing is, they still dated for a few weeks after that before she broke up with him. We hooked up a few more times the next year before I started dating someone else. Mike and I’s friendship kinda fizzled out as the often do in high school. Nothing went wrong, we just grew apart. He’s married with 2 kids today and as far as I know, he never found out that I fucked his first girlfriend.
Source: reddit.com/r/gonewildstories/comments/gv8h70/i_fucked_my_best_friends_girlfriend_in_high_school