Losing My V-Card On A Sexcapade

by Colin

What’s your gender? Man
How old are you? 40
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? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
What’s your 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? 1

Losing My V-Card On A Sexcapade

How long ago did this hookup happen? 20 years ago

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? Just met that day

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 was in an Asian country as a student. My friend came to visit and we headed down to the beach. I had no idea it was a crazy, sex-crazed, party beach area. I was a virgin, so my radar was pretty bad for these things. We went to the beach for drinks at a bar. We were sipping beers when two lovely ladies walked up. I was hesitant to engage them much, unsure of their intentions. My buddy was very clear on their intentions and kept buying them drinks. Finally, the other girl asked him to leave with her. They left. I told the lady I was with, “N”, that I’d walk her home. She acted a bit surprised and said “no, I go home with you.” I knew right then that this was probably the way I’d lose my v-card.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We went back to my hotel room and we each showered separately, I went first. Then she came to bed wrapped in the towel from her shower. She got on the bed and slowly began touching me, eventually reaching my cock. She stroked it, although I was already pretty hard. I didn’t know what the hell I was doing, but I took off her towel and began sucking on her nipples. Finally, I worked up the courage to put my fingers on her thighs, then to her pubic hair, then finally her pussy. I’d never felt that before. She was wet.

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? I began fingering her with very little skill. She at least pretended to enjoy it. Finally, she put a condom on me, and straddled me, slowly lowering herself onto my cock. I remember the warmth and realizing how much better this felt than masturbating. She began bobbing up and down, up and down. We eventually switched positions. I was nervous and in awe at the same time, so I actually lasted longer than I would have expected. I came in the condom during missionary. We fucked again later, then slept.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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? That night we slept naked. I woke up the next morning with an erection. I began gently fondling her and getting her aroused. She responded by stroking me. Then, I put on a condom and began fucking her in a spooning position. I remember it felt extraordinarily good. Warmer and wetter. I came hard and quickly. Only then, after pulling out, did I realize the condom had broken. She didn’t say anything about it, I’m not sure why. At the time I figured I came too deep for her to notice, but now I realize that’s probably impossible. Not sure why she didn’t complain.

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, Learning new things, experimenting, It was easy / convenient

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? My buddy and I acknowledged we had both gotten laid but didn’t swap details.

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

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I didn’t pay her, but she clearly did this with tourists for a living. I felt a bit predatory later on after I thought about it.

What was the BEST thing about this hookup? Experiencing sex for the first time.

What was the WORST thing about this hookup? Not sure why she wanted to do it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup? We stayed together for two weeks, fucking day and night. I was broke by the end. She got my sperm and my money out of me.

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