Location: New York City
Highest education received: Some college (currently in college)
Occupation: Full-Time Student
Relationship status: Open Relationship / Consensual Non-Monogamy
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 0
Losing My Virginity Via Craigslist
How long ago did this hookup happen? 3 years ago (I was 17)
How would you best classify this hookup? One Night Stand (Became FwB)
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? I met him on Craigslist, I didn’t know him at all. We both lied about our ages, claiming to either be a little younger or a little older than we actually were. He was Caucasian, 5’11 thereabouts, blue eyes, lanky. I was quite lonely, growing up in this country. I posted an ad and his response was one of two that I ended up responding to. We talked for about three weeks before meeting in person and hooking up in that same meeting. I could sense that there was a great deal of intellectual compatibility and similar interests despite our age difference (17 and 30).
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It’s hard to say. I’m the one who posted the ad, under the Strictly Platonic section, but the prospect of having sex was something I didn’t mind entirely. I was a virgin, I wanted to take this into my own hands; what I didn’t want was a poor sexual experience with someone inexperienced who would ruin my image of sex entirely. I wanted someone who knew what they were doing. The thought of even auctioning off my virginity for cash was something that crossed my mind. I never really valued it, or sex, as something that should be ‘special’.
That being said, the prospect of sex was discussed and we decided to meet in a park and have wine and see where things would go. But it rained, and we ended up going to his flat. We were on his bed, talking about one another, what he did for a living (he was a professor at a local university), how I came to his country, my plans for university, etc. We talked about my favourite books, his favourite films, music that we both liked. The atmosphere was definitely charged with sexual tension, but it remained very casual. There were never really any awkward silences, just a lot of staring and laughing. He would run his hands up and down my legs, and I would roll over in fetal position to get away. That sort of behaviour. I was laying down on my back, and he tried to kiss me. But I refused. I refused three times before giving in and eventually straddling him, and then clothing and such started coming off.
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? He knew I was a virgin so he tried to be gentle with me. Most of his kisses were gentle, but I changed the situation into something of greater urgency, with much more passion. I really wanted to do this. He gave me oral and fingered me, it wasn’t my first time to receive either of the two, but arguably it was the best I had experienced. I reciprocated, naturally, gave him oral as well. What I remember most was that he said I tasted like vanilla, and that he couldn’t get enough of it. I lost my virginity in missionary, my legs spread, somewhat in the air as he held them; he had a condom on now, and he asked if I was sure I wanted this, and I said yes. I remember feeling this sensation of feeling overwhelmingly filled, this pleasurably full sensation that filled my entire lower belly. I didn’t orgasm and it didn’t last long, since he said because I was so tight, it wasn’t hard for him to cum.
I remember after he pulled out and disposed of the condom, I put my head on his chest and said, “So that’s what sex is like…” And he said, “Yes,” and I excitedly sat up and said, “Let’s do it again!” And we did, eventually, and it did last longer this time, and I tried being on top for a while, but after not being accustomed to the logistics of it, we went back to missionary and he eventually came again.
I saw it as an ultimately positive experience. We had a great rapport; it was fun, we were laughing and joking around as it happened, and it felt very comfortable. It was hitting midnight soon and since I was still in high school, I was supposed to be home by then. He let me freshen up, and he walked me out of his flat. He hailed me a cab and kissed me before I got in and told me that he had a great time and that we should do it again. And we did.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed STI history when we were exchanging emails still. We used a condom during both rounds of sex, and when it became a much more regular occurrence that I knew I wanted to pursue, I had to admit to my mother that I was sexually active so as to purchase the contraceptive pill (the country where I was living at the time didn’t allow minors to purchase the contraceptive pill without parental consent).
What were your REASONS for having this hookup? I was really getting tired of not having done anything. Not out of peer pressure, but because I had quite a prolific online sexual life. I was camming, spending time in sex chatrooms frequently, and had been for years. I knew my body quite well, I knew what I liked, what I enjoyed, the type of sex I would like, etc. I just wanted an experience that didn’t necessitate any feelings. I didn’t want attachment or affection, I just wanted to experience sex under my demands – with someone experienced, with someone who meant nothing to me, with someone who didn’t want a relationship, etc.
Were alcohol or drugs involved? If so, how much? 2 glasses or so, of Sauvignon Blanc.
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? We hooked up for about 11 months after that. It became a Friends-with-Benefits sort of scenario. I would meet him on Fridays after school, or he would come by during my free periods where I could come out and see him, and we would have sex in the fire escape. I experienced a lot of my fantasies with him, including also losing my anal virginity, experimenting with sex toys, shibari (Japanese rope bondage), sensory play (with ice cubes, mostly), sex during menstruation, exhibitionism, roleplay (Daddy/daughter dynamic), food play, uniforms etc.
When he left due to the end of his work contract, we remained friends and we still are friends. We’re still very close and talk to one another regularly.
To whom did you talk about the hookup? How did they react? Probably 2 of my friends, and my mother, eventually, when I had to ask for the contraceptive pill.
Was this a consensual and/or wanted experience for you? For your partner? Yes, it was for the both of us.
Do you regret this hookup? If so, why? No.
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? I think the best thing was that it was under my terms. I essentially got everything I wanted out of it, and so did he. We were compatible enough for it to become something regular, and it wasn’t only sexual compatibility, but intellectual compatibility as well. It’s important for me to be able to tolerate my lovers beyond the bedroom, so it was nice to always be able to have dinners together where conversation would ensue beyond “how was your day?” but also feel an intense sexual attraction to the person.
I think the worst part about it was towards the end, when it started to get a little messy – I really didn’t want him to leave and started to get quite sad about it. Needless to say, I suppose I did form some attachment to him, and even though it wasn’t reciprocated, he was very kind about it. I knew that our bond was special and still is; the fact that he still calls me “daughter” and I call him “Daddy” goes to show that. We still have that dynamic about us.
It didn’t really change anything about casual sex for me, other than the fact that I realised that it was possible for me to do it; to feel comfortable asserting myself sexually with a stranger. In many ways, it made me feel much more confident. While I was generally sex positive, my online sexual activities were things I often did when I felt insecure or depressed, and being able to have a real-life, tangible, healthy sexual experience changed that.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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