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What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 2

Getting Over an Ex

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For 1 to 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was a blonde bombshell with blue eyes and an extremely attractive personality. One time, her, my ex and I went swimming and she had one of the hottest bodies I had ever seen. Maybe it was the surprise because she didn’t wear clothes to accent it, but she caught me looking a couple times and just smiled at me. My ex and her had been friends for a couple years up until that point and we had become friends of her family eventually. While I was very physically attracted to her, I never flirted with her or made it too obvious since I was with my ex girlfriend at the time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When my ex decided to move we had to live together for a month until she left, so we stayed fuck buddies until she left. We went to visit my ex’s friend, let’s call her L, at her mom’s house and we ended up having a pretty good visit, but I could tell they both felt really sorry for me since I was kind of bummed out in general. I wasn’t very upset about the breakup, and at that point was ready to start moving on. My ex was leaving in about a week during that visit, and I was going to stay in town about a month after before I moved away. Before we left, L pulled me to the side and told me to text her if I wanted to hang out so I wasn’t too bored during that month. I didn’t really think anything of it at the time but sure enough, I got bored and sent her a text. At first she didn’t respond but a day later she hit me back and apologized, asking if I wanted to go get some food. I said sure and we met up at a local food spot to hang out.

While we were at the restaurant, L was acting differently than usual, and I realized I had never seen her nervous before and wasn’t sure if that was the issue or what. We hung out and actually had a really good time chatting about everything, and I made it clear that my ex and I were over at the time despite my ex almost immediately trying to reopen the possibility of getting back together after leaving. She thought that was ridiculous and I agreed, and told me some stuff she noticed about my ex that made some of the things happening in our lives make more sense.

Somewhere during that conversation I realized her leg was touching mine and we had just left them touching. When I realized it I got a slight rush of anxiety but kept talking about whatever it was at the time. We both relaxed a bit as we finished eating and I asked if she wanted to come swim at the pool at my apartment after. She loved the idea, so we went back to my place but it was getting pretty late. We got our swimsuits on but the pool had just closed, so we decided to watch some Netflix. On the way back to the apartment I accidentally bumped her butt with my hand, and she gave me the most surprised look that turned to a smile until she quickly looked away.

When we got back to my place we put something funny on and we were laughing our ass off. At some point she reached to put her hand on my leg but ended up ‘accidentally’ touching closer to my dick. We laughed but then started joking around, but then she moved over closer to me on the couch and I put my arm around her.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Right after I put my arm around her we started kissing. We both kept stopping to look at each other because we were both almost shocked what was happening, but we kept going with it. After a while of making out and rubbing up against each other’s bodies, she asked me if I was going to keep this a secret, to which I replied yes. She then stood up and started stripping her clothes off, as did I. I got on top of her on the couch and I started grinding my dick against her pussy, but kept teasing her with it instead of pushing it inside of her. I wasn’t sure if I needed to wear a condom so I was deciding on how I should ask or how I could pivot to get a condom when she reached down, grabbed my dick and pulled it inside of her.

She was about 6 years younger than me and was incredibly tight, much tighter than I was used to, so I started fucking her pretty slow. She kept rolling her eyes and head back, so I started sucking on her tits and pounded her harder. At some point I realized I was incredibly turned on and I didn’t want to embarrass myself by popping early, so I pulled my dick out of her and lead her into the bedroom so we could fuck easier than the couch.

She sat back on the edge of the bed and pulled her legs back, so I took my fingers and started fingering her. She started moaning really loudly and I knew I had her not far from cumming, so I started eating her out along with it and she started going crazy. After a while she pushed my head back and signaled me for me to put my dick back inside of her, so I happily obliged and moved to the edge of the bed, rubbed the tip on her clit then slid it back inside of her.

Luckily in this position she wasn’t as tight, so I just started pounding her pussy as hard as I could. From then on my dick was okay so I just kept fucking her in different positions, and our fucking got rougher and rougher. She started talking dirty and I turned her around doggy style. I started getting close to cumming so I asked where she wanted me to cum. She told me anywhere, and probably three pumps later I was shooting my load as deep into her as I could.

After fucking the first time we collapsed exhausted on the bed and were laughing about it like stupid kids. We agreed it was like we had a ton of sexual tension we just unleashed, and it felt so good. While chatting she told me she had an IUD, which she got thanks to the recommendation of my ex girlfriend. That’s all I needed to know to bend her over and start fucking her again. We fucked until my dick was literally too sore to fuck anymore that night, and continued when we woke up the next morning. We also found out we had some of the same fetishes, so we explored with each other quite a bit.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Before she had left we made it a point to say we would not do it again. At the time she felt a little guilty for fucking since I just became her best friend’s ex, but I knew it was probably a fleeting feeling. The next night we were back at it again, and for the next month we made it a regular occurrence. I had considered getting into a relationship with her, but given that I had just left a long term relationship and she kind of reminded me of my ex, I decided against it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device)

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Marijuana, hashish

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I didn’t tell many people, and when I did I was pretty discreet about it. She, however, did not stay quiet about it and I actually had sex with another one of my ex’s friends as a result of her stories. At the time I wasn’t very confident, and that was a big confidence booster.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? I did like her and she liked me, and I think we both felt eventually that we wasted something that could have been between us. With that being said looking back, that would probably have not been a good idea.

What was the BEST thing about this hookup? Having the new friend feeling before the new sex partner feeling. Having fun before and being flirty made me extremely attracted to her before we started having sex. We both quickly trusted each other and that’s sometimes dangerous.

What was the WORST thing about this hookup? I hadn’t had a new sexual partner for years, and having had sex with her unprotected made me worried she didn’t actually have an IUD or wasn’t clean, but luckily that ended up not being the case.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little bit. In this case, I feel casual sex possibly ruined a friendship that could have become more. With that being said I was never sure about dating her, and just that reservation alone tends to suggest that it wouldn’t have been right.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

You have a hookup story to share? Submit it here!