[MF] I (22M) fucked a highschool crush (22F) 5 times in one night.

This was back a few years ago. Let’s call her Kelly to protect her real name. You can skip down to the “*****” to get right to the sex part.

For some background, I was very naive when it came to girls back in high school until my freshman year in college. It really never clicked in my head when a girl was flirting with me, wanting to have sex with me, etc. and I cringe everytime I think back on it. There was this one girl, Kelly, who I’d known since middle school, and apparently throughout the years she had little crushes on me, and I had completely no idea. I just thought she was nice and would make random small talk lol.

Anyway, by the time she was a senior in high school she was very attractive, in great shape from running track, and had double D (or larger) boobs. She had a few boyfriends throughout high school, so I never paid her a second thought. Then we both went away to colleges on the opposite sides of the state.

She was single again our freshman year, and we randomly started to snapchat every day. Again, I thought nothing of it lol. Eventually I got a gf who I dated until I graduated, so nothing ever became of me and Kelly.

Then finally after graduating, I broke up with my gf of 3 years (she was crazy, but lots of amazing sex if anyone wants to hear those stories. She was also the only girl I had dated or had sex with until this point in my life). It was summer break, and I was ready to celebrate and relax for months before I started grad school. One day during the summer, me and my friends went to a bar in our college town and randomly ran into Kelly with her friends. My friends had been telling me for years that she wanted me, so I finally thought I’d go for it.

I walk up to her at the bar and we hug and I invite her over to hang with me and my friends. After a couple drinks I ask her to dance, and she just says “don’t you have a girlfriend?” I explain the situation, that I’m finally free, and I can see some relief on her face. But then she just says she just wants to chill and hang out. So I’m thinking, dang I got rejected. Oh well, we all still have a fun night. I mostly hang with my friends, but talk to her every once in a while since I assume she’s not interested.

We all stay at the bars until they close. Once we’re all about to call ubers home, I see one of my friends hanging back with Kelly and whispering in her ear for like 5min, and they keep glancing over to look at me in their conversation. I have no clue what he’s saying, and I hadn’t talked to her for about an hour. Then, Kelly walks over to me and says she’s coming home with me. The next day I asked what he had told her, and he said he just kept telling her that she should go home with me lol, what a great wingman.

***** Sex starts here*****

All I can say is “okay!”. So she gets into my Uber, and we head straight to my apartment around 2:30am not saying too much. We get upstairs and she starts talking about how she thought I never wanted her and how she’s been wanting to come over for years. I explained I was basically a child back then and didn’t realize it, but I’ve finally grown up. She accepts that, and we go to my room.

She was wearing a sundress, apparently with no bra, and the second I close the door she takes her dress off over her head. Out drops the biggest titties I’ve ever seen in my life – double D or bigger. I was instantly hard. She then tells me to lay on my bed and asks me to hand her a condom. She takes my pants off, pulls out my dick, puts the condom slightly in her mouth, and then swallows my dick whole. She comes up for air after a couple seconds and the condom was miraculously perfectly on – I was in shock and had never seen anything like that. I’m just thinking wow, this is really happening.

She then mounts my hips, grabs my dick from the base, and slides me right into her already soaking wet pussy, and begins to bounce and ride like a pornstar. She learns forward and I start sucking on her nipples like a starved baby. Her titties were beautiful, and bouncing around on my face. Then she leans back and grinding, and I start to rub her clit. Then she grabs my hand, with my finger wet from her dripping pussy, raises it up and sucks all of her juices off of it. I’m basically in heaven.

Honestly, I don’t know how I didn’t instantly cum in those first 5min. I think it was from the alcohol, and I could feel the lessened tension and sensation in my body, so I knew I was going to last as long as I wanted, thankfully. I flipped her on her back, lifted her legs up, and began pounding her nonstop. Her titties were almost smacking her in the face, just bouncing up and down. Not sure if they were hurting her, or she was a little embarrassed by that, so she squeezed them both in her hands, and that was even sexier. Eventually I start to slow down and now we’re in missionary. I start slow stroking her, and she whispers in my ear “it’s okay, you can cum”. That’s all I needed to hear, and I shoved my cock as far as it could go inside her and emptied out everything I had. I probably came for at least 1-2 minutes straight and thought cum was going to leak out of the condom.

I got out of bed and went to the bathroom to wash up, it was about 4am at this point. When I walk back to the room she’s already sound asleep. So I just get back in and fall asleep with my arm around her.

Then, probably around 7am with the sun rising and peaking through the blinds, I wake up to her starting to make out with me and stroking my cock. She instantly gets me hard as I remember what happened last night. We had our round 2 then fell right back asleep. Then finally I woke up around 10am starving, and went and picked us up some breakfast burritos since it looked like she had no plans of leaving. After we finished eating we cuddle on the coach for a bit, then she says “let’s go again”. So next thing you know I’m pounding away at her again all morning.

This routine continues – sex, rest and talk for about an hour, then back to sex. Finally it was about 3pm and she finally asked if I could drop her off at her friend’s house, since she apparently was just visiting for the weekend. I dropped her off and she just says she’ll let me know anytime she’s in town from now on (which she did).

That was some of the best sex I’ve had, and I still think about it years later. Our paths just never really crossed to make anything more of it. Oh well, great memories. Just wish I hadn’t wasted years being naive.

Source: reddit.com/r/gonewildstories/comments/jdbvix/mf_i_22m_fucked_a_highschool_crush_22f_5_times_in