Popping my Cherry



What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Promiscuous, Slut
How many sexual partners have you had in your life (including oral sex)? >120
How many hookup stories have you here posted before? 0

Popping my Cherry

How long ago did this hookup happen? 17 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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 about 17. However, she also worked at the local bookstore. I often visited during the weekends. She was a brunette with blue eyes, about 5’6”. She was pretty slim, but with a great rack. One of my friends mentioned she used to do some modeling. This chick was the epitome of cool. She’d sometimes be smoking weed when I went there. I had even smoked with her once or twice. I was really attracted to her, but I was dating my middle school girlfriend at the time. Also, she was a fair bit older. However, whenever we met, she’d always flirt with me a lot. Her manager usually left her to handle the store, since few people would come regularly.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day, during the weekend, I went to the bookstore, mostly to just see her. She was wearing a short skirt and a tight t-shirt. She was smoking a joint and we started flirting. I was usually pretty good at looking and seeming more experienced than I was (I hadn’t lost my virginity). We were the only two in the bookstore, and we somehow got around to talking about sex. She easily found out I was a virgin and started talking about her past sexual experiences, turning me on even more. Then, she looked me up and down, gave a sly smirk and said: “Maybe we could go to the backroom and have some fun?” I was really shocked. I didn’t think it would be so easy. She just grabbed my hand and took anxious me to the back.

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? Immediately after shutting the door to the backroom, she started making out with me. And boy, was she a great kisser. I immediately started exploring her body, from her shoulders down to her legs. She started unbuttoning my t-shirt while she was kissing. Soon, she took off my shirt and hers. I remember she was wearing a red bra and I immediately unclipped her bra and started exploring her huge tits. They were round more than long, but with large pointed brown nipples in the center. My dick almost exploded right there, but I somehow managed to keep on. She then lay flat on a table and guided me over her, letting me explore her body with my mouth and hands. She then immediately stripped me of my jeans and boxers and started sucking my cock. I do remember her commenting “Huh, you got a pretty big cock,” before getting to work. I had had a couple of blowjobs before but she was an expert, using her tongue and able to take my entire throbbing member. I couldn’t control it and I exploded in her mouth. She sucked it all like a pro. Then, she smirked sexily at me and took off her skirt and panties. She took my hands and had me explore her pussy. I had had a little experience with fingering before and I managed to make her moan slowly as I fingered her. Finally, the big deed. She lay back down on the table and guided my cock into her pussy. I didn’t have a condom but she said she didn’t mind as she was on birth control. What was really good about this was that she was always giving me guidance, telling me what she wanted and how to do it better. She’d even guide my hands and mouth physically. Moreover, she was pretty receptive, regularly moaning loudly. I could barely last a few seconds and came in her ( I mean, that’s what a tight, soft pussy does to your dick for the first time). She didn’t seem to mind too much.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? We just relaxed there for a bit. I was on a fucking high. She asked me how old I was and I lied, saying I was 16. She did say she hadn’t had any action in a long time and so didn’t mind jumping me and taking my virginity. We went to different schools anyway, so she believed me. Nevertheless, we decided not to tell anyone since we’d get in big trouble if we were caught fucking in the bookstore. After that meeting, we regularly met up for over a year (until she went to college) and she taught me so much about sex and how to pleasure the female body. We often did it in the bookstore, or in my house (my parents were rarely ever home, even during weekends). Still today, I remember learning most of my techniques from her. I did fall in love with her a little bit until she left and I got over it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

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 more desirable, To feel more confident, Power / Dominance, Submission / Relinquishing power, Making new friends, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

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

What substances did your partner(s) consume? Marijuana, hashish

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? Very

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 never told anyone for a long time. I was really frightened it was illegal or something. Also, I’d get in pretty bad trouble if it got out I had nailed someone at that bookstore. However, I finally told my 2 closest friends after swearing them to secrecy. They didn’t believe me for a long time (I mean, it is a crazy story) but they were pretty awed once I finally convinced them.

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

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sense of danger with it. I never thought about it at the time, but when I reflect on it, the fact that anyone could come in and hear us/ see us made it so much hotter since there was a risk of danger. Also, I lost my virginity to this really hot chick, and she taught me so much. Everything about it was great.

What was the WORST thing about this hookup? It led to a fuck buddies situation. I didn’t mind for a long time, but towards the end, I did get a bit attached. It hurt a bit when she left, but I got over it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Umm, yeah! I learned all about sex and how there was a whole world of sexual exploration before me. It really got me into understanding it and how to pleasure people became a huge part of my life.

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

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

Anything else you want to add about this hookup? It was just a wonderful, eye-opening experience.

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? Love it. I’ve enjoyed a lot of casual sex with a lot of people and I’ve always been someone who gets around. I think more people should take part in it. Its made me really comfortable with my sexuality. I wish people stopped being so judgy about it. I mean, its just sex and more people would be happier if they had a larger variety of it

What do you think about the Casual Sex Project? Love it. Sometimes gets me off. I hope to get more things off my chest with this.

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