The Last Time We Had Sex



What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
What’s your current relationship status? In a serious relationship (monogamous)
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)? 30
How many hookup stories have you here posted before? 4

The Last Time We Had Sex

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 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 tanned half Native American with blue eyes and dark hair. She was slim, short and very cute, with a nice round ass and huge tits for her size. We had been dating for 4 years up until a month before, where we broke up and decided to live together until she moved back to her home (we both lived away from home).

Fucking was about the best thing that we ever did together, so for the month before she moved we regularly hooked up. I knew at the time she was having sex with other guys even though she thought it was a secret, but I didn’t really care as I was also sexually active with other girls. I figured it out when she suggested we start using condoms under the guise that she got her IUD removed. I knew it was bullshit because that had happened over 6 months earlier and right after we split she made the suggestion.

Even though we were pretty upset with each other, especially me with her as I was the one who initiated the break up, we still considered each other good friends so the situation was a big mixture of sadness and being pissed at each other. This led to some of the best but weirdest sex we’d ever had.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the day before she got on the plane to fly back home and we were fighting about something random. We were both extremely pissed off and stressed out, as carrying out a sexual relationship with no break after splitting up had kept us both half attached to each other when we were trying to move apart. We had sold all of our furniture as I would be moving soon after too, so we were sitting against the wall on blankets watching TV. We were ignoring each other got a good hour or so and it was getting late.

After we cooled off a bit she moved over to me and said that we needed to just relax and have fun for our last night. I knew what she meant, so I leaned over to her and started kissing her softly.

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? Even though we had been hooking up we hadn’t kissed much since we split up. Slowly the kissing turned to making out and before I knew it she was straddled on top of me, making out with me against the wall. I rubbed her as hard as I could through our clothes and when I couldn’t take it anymore I got her off of me and spread a blanket across the floor as she undressed herself. We went right back to making out, with me on top of her, both of us mostly unclothed. I wasn’t planning on having sex with her again but before, but now all I could think about was getting inside of her one more time.

The more we made out the more we stripped our clothes off until we were both naked. She reached for a condom and gave it to me, and I sat up and put it on then slid into her missionary. Unlike the last month, she was locked onto my face, intensely locking eyes with me as I thrust in and out of her slowly. It was like we both knew this would be the last time we had sex and in that way it almost felt like our first time again.

We fucked harder and harder, and all of a sudden she told me to take off the condom if I wanted to. At first, I decided to leave it on and kept it on for another minute or two until I couldn’t resist anymore. I took it off and slid back into her, making out with her as we fucked raw for the first time in over a month. I then got her on her hands and knees and started pounding her pussy with her hair pulled how I knew she liked it. We changed up positions a few more times, with her rubbing her clit cumming multiple times as I pounded into her until we were back in missionary again.

I knew I was about to cum so I started making out with her as I pounded away, enjoying every bit of her pussy as I could. As I got close I was about to pull out to cum on her face just how she liked, but at the last split second I buried myself as deep in her as I could and came in her pussy. At first, she had a shocked look on her face and then she pulled me to her and started kissing me passionately. I got quite a bit freaked out as we kissed thinking about what I’d just done, as this was definitely NOT someone I wanted to knock up.

She pulled away and told me she had secretly been wanting me to cum in her but wouldn’t ask since she wasn’t on any birth control anymore. I pulled out of her and we started trying to get the cum out of her as much as we could but it never seemed to stop coming out. As I started to relax a bit, I got turned on by seeing my cum flow out of her, something I had never really experienced before. After we got most of the cum out I sat back up between her legs and to her surprise slid right back inside of her. We both got big smiles on our faces as I pounded the fuck out of her again.

From that moment forward the rest of the night was probably some of the dirtiest sex and talk I’d ever had in my life. We fucked like rabbits, with her telling me things like fill her up as much as I could as I’d never be able to again and to knock her up. I knew the whole time how stupid it was but after fucking up the first go already I convinced myself that nothing mattered going forward and kept finishing inside of her.

The next morning my alarm went off to go to the airport and I woke her up next to me. She was in an annoyed mood as she tried to wake up but seeing her naked and stretching next to me made me want one last go. I asked if I could get up in her and she nodded yes and said just don’t cum in me as she stretched. I pushed her legs up and slid into her again, just wanting to get my rocks off before she left as I pounded her as hard as I could. She just laid there half asleep waking up as I fucked her, and at the end, I nutted in her anyway. As soon as she realized I was cumming in her she just let out a god damn it and after I finished got up to go clean herself out.

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? We both got ready and my car packed and I took her to the airport. She was visibly annoyed, both that I was breaking up with her and also probably a bit annoyed that I didn’t pull out earlier. I dropped her off at her terminal, we hugged and I got back in my car and left. One thing I’ll never forget is how happy I felt to finally be done with her as I drove away.

The next day it was like I had woken up from a dream all of a sudden and I started to worry like crazy. I was kicking myself for being so stupid as I knew there was a good chance I knocked her up given the timing of when it happened. There was also the possibility of having an STD as I knew she had probably fucked a few other guys in that last month and possibly before that (which is why I stuck to condoms before then). Luckily I ended up clean and she told me later that ‘unfortunately’ I didn’t knock her up that night. I dodged a bullet there.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To cheer myself up, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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

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

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 anyone, as I knew I made a mistake.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? Honestly, I was only attracted to my ex physically at the time while she still had feelings for me and just wanted one last good fuck before I left and went all out. I sort of took advantage of the situation at the time.

What was the BEST thing about this hookup? Honestly, just the closure that came from it. Also, the high-risk sex with someone I was comfortable with was a huge turn on too at the time and after.

What was the WORST thing about this hookup? Worrying about having an STD or getting her pregnant was not fun at all afterward. That being said I’d probably do it again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little bit. I used to be all about my partner, but now I realize that it doesn’t always have to be that way for sex to be fun. Sometimes it’s fun to just let your inhibitions go and do whatever you want to.

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

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

Anything else you want to add about this hookup? If you break up with someone, it’s probably best to stop having sex at least for a little while.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Everyone sees it in a different way.

What do you think about the Casual Sex Project? Awesome!

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