34 Year-Old Virgin Meets a Woman on Reddit, Still Technically a Virgin (Sigh)



What’s your gender? Man
How old are you? 35 (was 34 then)
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Consultant
What’s your current relationship status? Single
Religious affiliation: Atheist
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)? 1
How many hookup stories have you here posted before? 0

34 Year-old Virgin Meets a Woman on Reddit, Still Technically a Virgin (Sigh)

How long ago did this hookup happen? 8 months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

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? She was a very attractive, petite Asian woman with long black hair, dark eyes, and a cute face. She was definitely “my type.” We met at a coffee shop near my house after having arranged it on Reddit. I had seen pictures of her before, but we had never met in person or talked on the phone.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She contacted me on reddit. My username outs me as a virgin, and she saw that I posted on an NYC forum. She checked my post history and confirmed that I was, in fact, a virgin. Based on that, she offered to have sex with me–to, as she put it help me get over one of my hangups. At that point, she hadn’t actually seen a picture of me or anything, which seemed to concern me more than her. So I sent her some pictures of me and she sent pictures of her. I kind of couldn’t believe that a woman that beautiful wanted to have sex with me. It wouldn’t have happened if not for the fact that I was a virgin, though.

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? Well, it started very awkwardly, with both of us drinking a fair amount of wine. I didn’t know how to go about getting things started, but she took charge eventually, and we kissed (my first time) and took off our clothes. We went to my bedroom. She gave me oral, then helped me to finger her. I went down on her, which was great. Definitely more fun than kissing, as far as I’m concerned. I just really liked the way her body felt all around. The whole experience of that was amazing. Unfortunately, I never got a proper erection, so PIV was just not happening.

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? I walked her out to her car and she left. She seemed to want to try again. I was unsure what I wanted, which I worry may have made her feel bad about the whole thing. She seemed frustrated that I couldn’t get hard, but also said she knew it was a possibility going in. I was hesitant to repeat the experience, I guess, because I didn’t want to find out if I had a real problem (i.e. I was worried about having it happen twice and then being even more worried about it). We also had some scheduling conflicts and at one point I missed her message because I wasn’t on reddit all day. She seems to have now abandoned her reddit account.

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, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Everyone else was/is doing it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? Somewhat

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 talked to two friends who know about my virginity status (both women). They were excited for me.

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

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

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? A little bit

Why do you regret this hookup? Well, in a sense, I’m still a virgin, and now I have this new thing (performance problems) to worry about if I ever have the opportunity to have sex again. Also, nothing changed about my “love life.” I still have none of whatever it takes to get another woman to have sex with me. So I look back on that experience all the time and I’m just sad that I can’t do it again.

What was the BEST thing about this hookup? Her body was so soft and nice. I really enjoyed being close to her. If PIV or having an orgasm weren’t a thing, I would be happy to just do what we did. I really liked cuddling and giving oral.

What was the WORST thing about this hookup? Well, she seemed disappointed, and I was sorry about that.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I definitely feel like I know more than I did. At the same time, it’s a lot more clear to me now that there’s a lot I don’t know. It’s really hard for a guy like me who is in his 30s and doesn’t have any experience, because there’s a pretty big risk if you tell the woman that you’re a virgin that she won’t want to have sex with you (yes, I know, some don’t care, but others do). So what was really nice about this–and what I wasn’t really prepared for, really–was that it was a great experience to be able to share that with someone who was interested in being a man’s first. I mean, all those feelings were amazing, and I think it would have been very hard to keep that to myself and act like I’d done it hundreds of times. And of course, there’s a lot that I didn’t know I didn’t know that she knew to help me with, like guiding me to her vagina, for example. So that said, I still don’t feel like I’d be ready to just go for it with the next woman–it would be nice to have someone who knows I’m still learning–but I still don’t feel comfortable talking about it.

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

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

Anything else you want to add about this hookup? I think that if I ever get out of this funk and have sex with someone else, I will be able to look at it as a positive learning experience. Right now, though, I feel like I got my first hit of something I need, but can’t have again.

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? I came to this page via a New Yorker article. To be blunt, it fucking sucks that everyone seems to be having sex but me. The idea that so many people just don’t care about it–and yet nobody seems to want to do it with me–that really hurts. As a general idea, I think it’s fine. I don’t see any moral problem with it. I think if I could, I’d have casual sex as much as possible. I think people need to loosen up about judging others’ sexual habits.

What do you think about the Casual Sex Project? It’s interesting and a little depressing.

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