by L

Gender: Female
Age: 23
Location: MD
Highest education received: Post-graduate degree (currently pursuing)
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

Nailed

How long ago did this hookup happen? 8 months ago

How would you best classify this hookup? One night only with a friend kind of deal

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? We were and are very close friends. We were in the same small department in undergrad together and worked together often. I think we considered each other like family, we’ve always acted a lot like siblings toward one another. We’d always talked about relationships and sex, and we have very different outlooks on the subject. He is a hopeless romantic, always fawning over some girl. I am a sucker for a casual situation, running from anything that seems too serious. I had moved across the country for a year and was pursuing a certificate in the southwest at the time. We talked a lot while I was gone.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was back in town during a break from my program. It was December. I had flown in that morning after an excruciatingly long two weeks of work. I had been hungover all day and was looking to make bad decisions. That night, a mutual friend of ours was having a birthday party. I hadn’t told anyone I was coming, so the party got crazy fast- celebrating a homecoming and a birthday? Shots of all kind were had quickly. He showed up a little later than me and we eventually went up to the roof to catch up, and so I could have a cigarette and he could smoke some weed. We were talking about the usual stuff when he started to freak out. He had been interested in one of our close friends for a long time. She was there that night and he was faced with some weird feelings he hadn’t been dealing with well. I had actually encouraged him to tell her a year prior, so he could get over it and move on. This conversation led to me admitting I had been rejected the week before by someone who I felt had led me on for almost 2 months. I hadn’t been interested in dating anyone in a long time, so I was a bit uncharacteristically vulnerable. We both had gross emotional bullshit we were dealing with. I went downstairs to get another drink. He showed up a few minutes later and that’s when he proposed we fuck.

“Let’s just do it.”
“Do what? Are you propositioning me right now?”
“We always talk about it, we talk about sex all the time.. I feel like we’d be good together. Come home with me.”

He was being so brazen and fearless with me. I’ve been told I’m intimidating by many men and enjoy dominating whatever situation I’m in. He knows me well and has been very much acquainted with my sass. He knew if I wasn’t into it, he would never live this down, he would be the butt of all my jokes, I would harp on him for months. He didn’t care though- and it was fucking hot.

We walked a drunken 2 miles in the rain and freezing cold to his apartment. He admitted he has been attracted to me a few years back and I admitted to him I’d always been curious about him sexually. We held hands for a while and the tension continued to build. During a lull in the conversation, I told him I was on my period, he asked me why that was important- I guess it wasn’t and I was even more turned on by his nonchalant attitude.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I remember how surreal it all seemed when we finally made it to his apartment. I was standing at the window, a fifth of bourbon down, staring out at the city, missing it and taking in the view. He came up behind me and started kissing my neck and eventually turned me around. We were making out, leaning into one another I could feel his cock getting hard in his jeans, never in my wildest dreams did I ever think I would be having this experience with this person. Clumsily and drunkenly we undressed each other and ended up in his bed. He went down on me for awhile and I was loving it, he was amazing, occasionally reaching up for my breasts while he sucked hard on my clit. It was some of the best oral sex I had received in a while. Occasionally alternating with his fingers, and me being turned on by his disregard for my period, I was almost there. I eventually couldn’t take it anymore and told him I wanted him to fuck me. I have no idea how long we fucked, or in what positions, just that I was drunk and that it felt incredible. No one came that night and we both eventually fell asleep. 

The next morning I woke up to a trail of blood to the bathroom. I was so drunk the night before a nail had wedged it’s way into the heel of my foot on the 2 mile walk from my boot and I hadn’t felt it until that morning. I showed him my foot and we laughed about how stupidly drunk we’d been the night before. We spent all morning in bed talking like we always had, about our lives and the people we’d been seeing and our work and the past. We eventually started making out again and I remember him slowly unzipping the hoodie I was wearing and began sucking on my nipples before he moved down. He pulled me closer by my legs and started fucking me again, this time we both came. I apologized for being super hungover and not doing much work and he told me he didn’t mind at all. We both agreed that we’d had a lot of fun and didn’t regret doing it.

Eventually my friends started calling to find out where I had disappeared to the night before, and I was late to brunch with some other out of town friends, so I bid him farewell and they picked me up, confused, from his place.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms, we didn’t discuss it, but we’re close friends and had previously discussed our sexual histories with each other.

What were your REASONS for having this hookup? We were both feeling rejected by other people and thought it might be fun. We were also drunk and horny.

Were alcohol or drugs involved? If so, how much? Lots of alcohol, I’m not sure how I walked away from that without puking all morning. He smoked some weed that night as well.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt a little weird about it. Not necessarily weird toward him, but I felt weird about how much I’d enjoyed it. We are still super close friends and have discussed it openly on a few different occasions. But I think I secretly want to do it again.

To whom did you talk about the hookup? How did they react? I’m not very good at lying, so when my friends picked me up the next morning I had no choice to dish. I got a few “Jesus! He’s like your brother!” but everyone mostly wanted to know if I had enjoyed it and that nothing would be weird between the two of us.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely consensual, we were shithoused, but we knew exactly what we were doing.

Do you regret this hookup? If so, why? Not at all. It was fun, I might regret telling him that it would never happen again after that trip. But I’m not sure he remembers that conversation anyway.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was really everything, it was a pretty phenomenal experience. Friend sex is something rare and special and has a totally different vibe than a relationship or sex with a stranger. The morning after was also really fun, just hanging out and fucking- what more could you really ask for?

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? I could’ve done without the nail in my foot the next morning.

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