I [M] fucked my best [F]riend’s 18 yr old sister

Quick disclaimer: I have depression and this took place when I was going through a pretty dark time. Everything is filtered through the lens of what was a pretty crushing breakup for me and I’ve tried to convey that. Any disappointment with, or judgment of, the girl in this story is only a reflection of how I was perceiving her at the time in comparison to my only previous partner, with whom I was still very much in love.

This got pretty out of control length-wise so I’ve added the little *sex starts here* line people seem to love so much. Scroll down to there if you don’t want the backstory.

I was around 23 when this happened.

I’d recently broken up with my girlfriend of five years and was spending a lot of time over at my best friend Luke’s house. It was late summer and we were both home from college so a few of us would hang out most nights drinking beers, shooting pool in his parents’ basement.

I’d always heard that Luke’s little sister, Diane, was a slut. She was probably 5’ 1” or 2”, very small, but thick in the ass and thighs like a gymnast, with a cute face, long brown hair, and average-sized boobs. She was five years younger than us so I graduated high school before she was around.

Whenever I was at Luke’s place she was always over at her boyfriend’s. The only time I would really see her was when Luke and I would be smoking on the front porch and she’d run out to her car, yelling to her parents that she was leaving. Her boyfriend was our age and a bit of a dweeb so everyone made jokes about his sister going over and getting railed by this guy. Luke was grossed out by it.

This summer was a little different: her boyfriend broke up with her in the spring. She started to hang out with us. I always got a weird vibe from her – I’d known her brother forever but their age difference was enough that they weren’t very close, which meant that she and I never really talked. And she was a brat. She had no problem throwing a temper tantrum with me around. I probably witnessed it happen once or twice a week over the most mundane things. She was always rude and shitty to Luke unless she wanted something. You get it. Anyway, part of the weird vibe was that I could tell she was into me. I’d catch her staring at me sometimes, and on the rare occasion that she did talk to me I could tell that she was nervous.

When my girlfriend and I broke up I noticed that Diane started paying me more attention. She’d just happen to be around every time I was there, wearing really short jean shorts in their cold basement. A few times she conveniently came down in a towel with her hair wet, thinking I wasn’t there.

Then she started texting me. At first it was just gossipy stuff about girls her brother was dating, things like that. I humoured her but, frankly, it was annoying. She was 18 but talked and acted like she was 14. It was obvious that she was looking for excuses to text me. But I was in a bad place after my breakup so even though she was annoying, any attention at all from a woman felt good.

She stepped things up pretty fast, started saying things like, “You know I’m 18 now right? :)”, or “All my friends are no fun I wish you would hang out with me.” I’d always politely shut her down. I really didn’t want to get involved with my best friend’s sister even if she was cute and had a slutty reputation.

But she persisted. She wouldn’t stop. Soon she was texting me every night, and now it was, “I think you should come over and fuck me. My brothers not home :)” or “Fucking my brothers friends is fun but you’re the one I’ve always wanted to fuck” (she always talked about how *fun* it would be). She was shameless. I said no over and over again but she kept grinding me down. She started sending me nudes and saying, “You could have this.” This went on for weeks. The longer it went on the more I wanted to give in.

I felt horrible for even thinking about it. I did want to fuck her – the taboo of it was hot. I knew it wasn’t right, I knew it would hurt Luke. In retrospect, if I’d really wanted her to stop I would have been more firm about it. I was hedging. It’s really hard to say no – and to keep saying no – when a hot, shameless 18 year old tells you outright that she wants to fuck you with no strings attached.

Summer ended and nothing came of it. I moved back to college about an hour away from my hometown. About a month passed and Diane’s texts became less frequent. But they didn’t stop altogether.

One night, I was sitting alone in my apartment watching a movie, still wallowing over my breakup and getting drunk, the way I spent most of my nights alone around that time. That, and jerking off constantly.

My ex and I had a pretty wild sex life – to this day she’s still some of the best sex I’ve ever had. She loved to be fucked hard and rough, and always insisted on swallowing my cum. I still get hard thinking of the smell of her pussy. It was intoxicating, not like any other girl I’ve been with. For the five years we dated we never stopped fucking at least once a day. Nothing beats sex with someone you know that well. Having that and going immediately to nothing at all was a difficult transition.

My phone lit up. It was Diane: “I’m visiting my cousin in [your town]. I can be at your house in 10 minutes. You should let me come over and fuck you :).”

I hadn’t fucked in months and I thought, as I always did, about just letting her come over. I was seriously tempted. But I told her again for the millionth time that it was a bad idea and I listed my reasons.

“It will be so fun!!” she responded, “I give the best blowjobs in the world :).”

I knew it was wrong but that was it. I didn’t even really like her. But I was too drunk and horny to resist anymore. I told her to come over.

—————SEX STARTS HERE—————

She knocked on my door 10 minutes later (she wasn’t kidding). It was awkward. She was wearing her standard uniform, little jean shorts and a tank top. We sat down, I offered her a beer, and we talked a little. I didn’t really know what to do. I hadn’t been single in five years. She didn’t seem to want to make a move. After about ten minutes I said fuck it and just kissed her.

She quickly climbed up on my lap and started grinding me slowly as we kissed. I opened my eyes at one point and she was smiling like she was very satisfied with herself. I grabbed her firm ass with both hands, spreading her cheeks open, and she moaned, asking me if I liked her young ass. I did. She kissed with a lot of tongue and her tongue piercing felt weird in my mouth, it kind of clanged around.

After awhile we moved to my bed. I took her shorts off and saw her pussy up close for the first time. It was the only pussy I’d seen in person other than my ex’s. I didn’t think it looked as nice. I ran my fingers up and down her freshly shaved, puffy outer lips, her left inner labia stuck out like a sideways tongue. I dug in. I remember being struck by how different the smell and taste was from my ex’s pussy. Diane’s pussy smelled almost rubbery, it’s hard to describe. I loved going down on my ex more than anything. This was different though. She didn’t seem to be enjoying it. She didn’t get that wet. I think, now that I was actually here and we were actually doing this, she was self conscious. Her boyfriend never went down on her. But who knows – she’d told me at one point that she’d never had an orgasm. I’m sad to say she’s the only woman I’ve had sex with who I wasn’t able to make cum. Not for lack of trying – I probably stayed down there for 20 minutes. It just wasn’t going to happen.

I went to grab a condom and she said I didn’t need it, she was on birth control. I was confused. Keep in mind that this is the first casual sex I’ve ever had. I was much more afraid of diseases than pregnancy. She was a little disappointed when I insisted but eventually she gave in and agreed on the condition that she could suck my dick first. I didn’t complain. She took off her top to let her pierced tits out and got between my legs.

She’d been bragging about how well she sucked dick for awhile now and, honestly, it was disappointing. It made me realize how amazing my ex had been at sucking dick. My ex would stare me in the eye and slobber all over it, rub it on her face – all that nasty stuff. Diane took the head and about an inch more into her mouth and bobbed up and down kind of mechanically without looking up. Her tongue ring felt nice but it didn’t even compare. Regardless, I made a show of moaning loudly and telling her how good she was.

I slipped a condom on and bent her over on the bed. She had a small mole just inside of her ass cheek and one of those buttholes with a little tongue that juts out from the middle, just like the one lip sticking out of her pussy. She arched her back and wiggled her ass at me. Her pussy was so tight I could barely fit my dick in. I have a very average-sized dick, around 6”, so it wasn’t a me-thing. She was that tight. I couldn’t believe it. The opening of her pussy felt like it feels when you squeeze just your thumb and forefinger in a tight ring around your dick. It was amazing.

Because of the drinking I’d been doing beforehand and my palpable sadness, I felt like I could last forever, even with her pussy gripping me like a finger trap. Normally this would be a good thing but knowing Diane wasn’t going to cum took some of the fun out of it for me. She didn’t make much noise and avoided eye contact. She let me do pretty much whatever I wanted to her – I pulled her hair and spanked her as I pounded away – but all I was thinking about was how much better my ex had been. Diane just didn’t seem to enjoy it.

I got the impression that Diane liked the idea of me liking her enough to fuck her more than she liked actually being fucked. Here I was thinking I’d be having wild sex with this young girl who loved to fuck, only to realize, mid-fuck, that she didn’t sleep around because she loved sex at all. She slept around because it was a way for her to get guys to like her. I still remember the moment that I realized this as I was fucking her. I felt like a piece of shit.

Eventually I flipped her over and came on her tits. I’ve always been pretty proud of the size of my loads and this one was no exception. I was hoping she’d lick it up but she went to the bathroom to wipe it off instead.

When she came back we talked awkwardly for a while before she eventually fell asleep. I got up and watched the rest of my movie. When I woke up beside her I felt a strong pang of guilt, not only for betraying Luke’s trust, but also for taking advantage of this girl who obviously had some major self-worth issues to work out.

But what’s done is done and we fucked again in the morning anyway, spooning, this time with her finishing me in her mouth and swallowing my cum. It was a little better than the night before but still underwhelming and, for me, deeply sad.

I still regret fucking her. I regretted it while I was doing it. Even so, I’d go on to fuck her three more times over the next year or so before I finally put a stop to it.

And Luke still has no idea I fucked his little sister.

Edit: Formatting

Source: reddit.com/r/gonewildstories/comments/bo6sb5/i_m_fucked_my_best_friends_18_yr_old_sister