Close Friend In College

by Frank

What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual

Close Friend In College

How long ago did this hookup happen? 7 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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? Natalia was a classmate from Italy, about 5’5″, D cups, fit but not skinny. She had a warm, genuine smile, a thin upper lip, and long, slightly wavy brown hair. We had been neighbors freshmen year and she was probably my closest female friend at the time, when we were juniors. Since she was from abroad, I invited her to my family’s house for Thanksgiving the year before. She was a year older than me and had had the same boyfriend the whole time I knew her. So although I always thought she was attractive, I had long ago put it out of my mind that I would ever get with her. She had previously given me really good advice about understanding women and sex in general, and I think she was the only person who knew when I lost my virginity the year before.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’d often come by Natalia’s dorm to say hi and chat during the semester, which was only a block away, but somehow, in that week that we hooked up, it so happened that 2 days before we had both broken up with our significant others. I messaged her asking her to hang out, just thinking that we would talk about our frustrations (we had both been the ones to initiate the break ups). She was usually busy, so I was surprised when she said yes. This time, she came to my apartment, since she had been meaning to come see it for a while. I met her at the door and we hugged, then I showed her around my suite. We ended up in my bedroom, chatting. I had this feeling of excitement, freedom, and connection about being able to share how we were feeling. I offered her a beer, and though it was a weeknight, she gladly accepted. I think we both drank with a sense of abandon, and right away I started feeling buzzed. We started watching youtube videos, but feeling a good connection with her sitting next to me, I started touching her shoulders and let my hand rest on her thigh. After a few minutes of brushing against each other, she suddenly asked me: “Do you think it’s okay if we kiss as friends?” I wasn’t looking at her, but paused for a second to let the moment sink in. It felt as if everything I had wanted yet simultaneously repressed had led to this moment. Then I turned to her, smiled, and said, “do you mean like this” as I leaned in to kiss her. As were making out, I eventually went to close the door and lifted her up on to my bed (which was raised, dorm-style). We made out some more on the bed and I took her shirt and bra off, but when I reached down to unbutton her pants she declined. She put her clothes on, gave me one last kiss, then left. I felt satisfied, but uneasy, not knowing what would happen next.

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? The next day, I messaged Natalia again to meet up, thinking that we would just laugh it off and pretend that nothing had happened. But of course a part of me was hoping we would continue where we left off. She agreed, and so the next day I came to meet her in her apartment. There we talked about what happened. Thinking she might want to forget about it, I fed her an excuse that we were just drunk and fooling around, but she mentioned that I really “seemed to know” what I was doing when we were making out and that she got really nervous when I had hesitated to kiss her. She also mentioned that her ex-boyfriend was actually coming to visit her at the end of the week, even though they were broken up. By this point, I was so horny that I could barely comprehend the thoughts that were swirling in my brain, and I told her that I couldn’t think straight.

During a pause in the conversation, she gave me a look as if to say the next step was up to me. So I got up off the floor where I was sitting, walked over and started kissing her again. We moved back to the carpet while making out, and I immediately took her shirt off. I put my hand in her pants and her pussy felt so wet and soft. I awkwardly pulled down her pants and stuck my tongue inside of her. But I probably wasn’t very good at it, considering I didn’t know where the clit was. After about a minute of that, she told me that it was my turn. As I lay down and she pulled down my pants, I felt a sense of awe at what was happening. Then she took me in her mouth and started blowing me with more saliva and better pressure than either of my previous two partners who I had done that with. Before I knew it, she was straddling me and hovering on top of me, telling me to warn her if I was about to cum. As I agreed, she guided me inside of her as she squatted on top of me.

I was really enjoying the sex, but since I had never cum during sex to that point, I was scared that I might do so prematurely and stopped her early. We both got up and she seemed concerned about continuing without a condom, so I got one out of my wallet and we moved to the bed. There, we did it missionary; I was amazed that she didn’t seem to care about the sound of her moaning and her bed hitting the wall, even though there were other people just outside her room. After a few minutes, she offered to get on top. As she rode me, she reached back with her hand and stroked my balls, which was an amazing feeling. In hindsight, I don’t think I reciprocated the touch enough, but I did grab her breasts (who wouldn’t have?). Then I got back on top. She asked me if I had ever seen a girl a cum. When I said I hadn’t she showed me how to rub her clit as I thrust in and out of her, but I don’t think she ever got there.

Eventually, I got soft and couldn’t get hard again. She pulled off my condom and started going down on me again. It was sexy as hell when she looked me in the eyes and told me she just wanted me to cum, but I was pretty inexperienced and didn’t know how to get in the right mindset, so I told her we could just stop.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

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? Afterward, we hugged, kissed, and I left. Her boyfriend came to visit soon after, and they got back together. I felt pretty guilty, since I hung out with them back in her hometown while studying abroad the next semester but had to pretend nothing had ever happened. After we got back to school and saw each other the next year, I realized that Natalia was avoiding me, to the point that we basically stopped speaking senior year. She did mention at some point that a mutual friend had told her that there was no way she and I could date; I took this to mean that she had told the friend to get her opinion. For years afterwards I tried to stay in touch, but Natalia didn’t reciprocate. Even though she eventually apologized for how she handled it, our friendship wasn’t the same afterwards. In hindsight, I regret having sacrificed such a close friendship for one night of sex, even if it was a formative and memorable experience.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel more confident, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Some guys who knew us both said they expected it to happen, which was crazy since it was never even an option in my mind

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

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

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Somewhat

What was the BEST thing about this hookup? She was hot and we knew each other well.

What was the WORST thing about this hookup? Eventually losing a good friend.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don;t think friends with benefits is possible.

All things considered, how NEGATIVE was this experience? Somewhat negative

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