Losing My Virginity



What’s your gender? Woman
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Bay Area
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Director of Executive Dining
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? Over 100
How many hookup stories have you here posted before? One

Losing My Virginity

How long ago did this hookup happen? 33 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? For less than a year

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? He was a boy in one of my classes; I think it was math. He was quiet and shy around girls.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I previously had sex with 3 or 4 girls my age and one who was three years older than I was. I wanted to see what it would be like with a boy. I looked for a boy who I thought would keep his mouth shut after and also one who was an only child and had no parents at home after school. I flattered him by telling him how smart he was and asked him to help me with the homework at his house after school.

I started with kissing. I had never kissed a boy before but I didn’t think it would be that different. He had never kissed a girl and while he was shy, he wasn’t at all reluctant. After a couple weeks of kissing that got progressively more passionate, I asked him to take his shirt off for me. He looked puzzled but did it. I took my top off but left my bra on. We kissed and I played with his nipples and got him to put his hand on my breast.

He really got into that and I had no difficulty a week later when I suggested we both take off all our clothes except our underwear. We both loved the skin to skin contact as we kissed and touched. On the other hand, he seemed shocked a few days later when I took my bra off and took quite a while staring at my breasts and was initially uneasy kissing me that way.

The second day I took it off, he was eager and on the third day, I asked him to take my bra off for me. I slowly got him to do more things. I had him touch me down there through my panties and I rubbed his penis through his briefs. Then a few days later I suggested we undress each other; I left his briefs on so he followed my lead and left my panties on. We got our hands under the waistband elastic and then later I spread my legs and got him on top of me and we did some very stimulating dry humping.

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?

After a few days of nearly naked making out, when I was undressing him, I removed his briefs and he reciprocated me taking my panties off. There was a little bit of unease because neither of us had seen an opposite-sex person totally naked. I didn’t know if he knew that I wanted to go all the way but after we kissed and touched and I spread my legs for him, he got on top of me. It took only a second or two for him to get his penis inside me.

The times we had dry humped and neither of us had an orgasm. I had an elaborate masturbation ritual where I peeled a carrot, warmed it up in a sink of hot water and teased myself by rubbing it around externally, finally sliding it in and vigorously bringing myself to an orgasm.

Unfortunately it didn’t work that way at all. He had an orgasm but I never even got close. After he finished I grabbed his fanny and tried to keep him inside me and keep going. He pushed himself away and I let my frustrating show. It was awkward and embarrassing; me laying on the rug naked and him standing and looking at me. We had nothing to say to each other and I got dressed and left.

The next day at school we were both embarrassed and didn’t speak. I was really conflicted; I wanted to go over to his house and do it again but we had no access to any kind of birth control and I feared to get pregnant. Even with that fear though, honestly, if he had asked me I would have done it again with him.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

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? After a couple days I arrived at the conclusion that I was glad it was only once. I thought the reason I could have orgasms making love with other girls and not with him was obvious; I was a lesbian. Looking back on it now I realize we should have talked about it more before we did it. It also would have been nice if we had access to condoms.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Learning new things, experimenting, Thought it was an important experience to have

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 didn’t give a clear ‘yes’ but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Absolutely no one until many years later.

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

Did you get emotionally hurt as a result of this hookup? A little bit

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? I think I probably hurt his feelings.

What was the BEST thing about this hookup? I liked the feeling of having his penis inside me and of kissing and coupling.

What was the WORST thing about this hookup? I risked pregnancy and got no orgasm.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I didn’t love him at all. Later in high school, I had casual sex with another boy my age; I was on the pill by then and things went much better. I also had casual sex with a few much older married men. One of whom I fell in love with.

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

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

Anything else you want to add about this hookup? The big thing I learned was that I liked having sex even when I didn’t get an orgasm.

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 had sex a lot in college and faked orgasms many, many times. In my 20s, I was quite promiscuous. After I got married when I was 29, I fully intended to be 100% faithful but we got involved with another married couple. Later I cheated on my hubby a couple times when I was out of town.

What do you think about the Casual Sex Project? I like reading what the other people are saying.

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