27-Year-Old Virgin



What’s your gender? Woman
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Midwest, USA
Highest education received: Some college (not currently in college)
What’s your occupation? Unemployed
What’s your current relationship status? Single
Religious affiliation: Atheist
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Polyamorous
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? One

27-Year-Old Virgin

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Dating casually

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

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? I had met “Oz” two years prior at work. I thought he was cute, he was dark, brooding, into metal, and decently older than me. I kinda had a crush on him at the time, but I started dating another coworker. I saw Oz once after I left that job but that had been it. Then one night at 2:30am I received an instant message from him saying we should grab coffee sometime. My boyfriend and I were taking a break and I had moved into my own apartment, so I agreed. I was slightly suspicious though, because Oz was friends with another guy I was hooking up with and I wondered if that guy had told Oz I would put out. I mean, it’s true–I would!! But still.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He took me out to eat and paid for my meal… very gentleman-like. I was pretty nervous because I didn’t know if we’d get along, but we found enough to talk about for the most part. There wasn’t really a connection more than friendly conversation, but I still thought he was cute and I was hoping he would be uncircumcised. We went to a cafe-bar and he downed some brews while I drink a coffee. It was getting kind of late so I asked him if he wanted to watch a movie at my place. He agreed.

He suggested Eyes Wide Shut which I had never seen (smooth, looking back on it). He was super afraid of my cat, for some reason. Every time she would jump on the bed, HE jumped! At first I was amused but then he almost kicked her. That kind of threw me off so I decided to shut her in the bathroom for the remainder of the night.

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? During the first sex scene (spoiler alert?) he moved my laptop off the bed to the desk and crawled back to kiss me. We made out for a bit and I escalated the situation by taking my shirt off. I was on top of him grinding. Then I moved down to give him head. He was cut to my mild disappointment. He wasn’t really getting as hard as I would have liked, and he kept telling me to show him my “big brown eyes” which made me feel like he was living out a porn fantasy. I’m not usually judgy but that’s definitely how it felt; we weren’t really on the level where sucking his dick was the greatest thing in my world. But I did it. And eventually I grabbed a condom from my drawer and asked if he wanted to fuck me. He asked me to put the condom on him, but his erection kept losing umph. However after a few more sucks I got it on and climbed on top of him and rode him. It was awkward and I was not really into it, plus his penis was pretty soft. After a while he did cum and we lay naked side by side. I was asking him all sorts of questions about his sexual history trying to piece together why it went the way it did. He said he had never had sex before–he had gotten a handjob but that was it.

How sexually satisfying was this hookup? Not at all

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? I felt horrible afterward. If I had known he was a virgin, I may have treated him a bit differently and with less expectation. He said he hoped we would be fuck buddies, and I told him we could be. But the more I thought about our interaction, the less I wanted to see him again. It left me feeling used. I think I just really wasn’t sexually attracted to him but wanted to have sex for the experience– and my body and mind did not cooperate.

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

What were your motives for this hookup? I was feeling lonely, Making new friends, Material rewards (gifts, money, drinks, dinner…), Boredom

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

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 told my best friend. He came over the next evening and fucked my brains out with a rabbit dildo, teasing me with “You had a different guy in your bed less than 24 hours ago. I’m here to really pleasure you.”

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? Very much

Why do you regret this hookup? I was just having sex to have sex. Oz didn’t attempt to give oral, finger me, or even rub my clit.

What was the BEST thing about this hookup? It taught me that I have to be more assertive with my own needs and not just cater to my partner.

What was the WORST thing about this hookup? Pretty much everything

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I learned that I should listen to my body and if I don’t want to have penetrative sex, I don’t have to. I was playing a sort of numbers game at the time, trying to have as much sex as possible, and it really bit me in my emotional ass.

All things considered, how POSITIVE was this experience? Not at all positive

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

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 like casual hookups but I think being choosy with your partners isn’t a bad thing.

What do you think about the Casual Sex Project? I love it and there is a lot to learn from the data being collected! I will continue to share my most memorable experiences.

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