Cherry-Popped a Non-Virgin



What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
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)? 50, 55-60 if you count oral
How many hookup stories have you here posted before? A dozen or so

Cherry-Popped a Non-Virgin

How long ago did this hookup happen? When I was 18

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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

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? Libby was an actual model. She was 5’10”, around 120lbs, had nice 32 B tits, and a great ass. She was a “white girl” who grew up in Miami; she had fair skin, dirty-blonde hair, blue eyes, full lips, and a killer smile. She was very, very beautiful.

Before my very first semester at University, after moving early into the dorms (like a lot of incoming freshman did), I met Libby through a new friend I had just made. He had known Libby in high school and I was introduced to her a few weeks before classes started. She wasn’t my type physically (I like dark hair and tan skin), but she was astonishingly pretty and very smart, so I pursued her without hesitation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After playing pool in the basement with some friends for a while one day, I asked Libby to come up to my room with me for some weak reason I made up. My roommate hadn’t gotten into town yet, so I knew it would be just her and I up there. She was a smart girl, definitely knew I had impure intentions, but happily agreed to accompany me anyway.

When we got to my dorm room, Libby and I began a more intimate conversation than what we were able to have around our friends. I found out that she had an ex-boyfriend back home who still felt that he was Libby’s current boyfriend. She had lost her virginity to him, he had been the only guy she had ever been with, and she sort of unsuccessfully tried to break up with him when she left for college.

As the conversation went on, we got closer and closer to each other until we were finally so close that it was obvious we wanted each other. It should have been obvious before that, but hey, we were only 18. Anyway, we began kissing and feeling each other up. Pretty soon, the clothes came off and we were pleasing each other orally. She made a comment about my dick being twice the size of her ex, but I took this as an exaggeration and not literally. While she went down on me, Libby offered to put her pinky finger up my ass and I quickly- and emphatically- told her “hell no.” “Some guys like it,” was her sheepish reply.

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? Unable to make one another cum from our oral attempts, we decided to have sex. Libby was apprehensive about rushing into it and made sure that I took it very, very slowly. I obeyed her wishes, lubed my dick up with her saliva through some gentle face-fucking, and positioned the head of my dick at the front of her pussy.

Libby seemed really nervous, as if it was her first time. I knew it wasn’t, so I began to think that maybe I was a lot bigger than her ex like she mentioned. Regardless, I entered her, she gasped, and her hands squeezed my triceps. I had taken one girl’s virginity at this point in my life, and I was definitely seeing a lot of similarities. Libby was trying to make it seem like it was no big deal, but I could tell she was in pain. I asked her what was up and she just said “it’s…just…really big.” I’m not sure there’s anything more flattering than seeing a girl wince at the girth and length of your dick while hearing her make a sincere comment about how big it is. I was in complete heaven.

Anyway, I made sure it was okay with her that I kept thrusting forward. She said how it felt good- hurt, too- and that I should go all the way in. When I finally started to get myself inside of her, I felt resistance. I thought maybe I was just in an awkward position, so I re-aligned myself and thrust again. This time I heard a pop and felt my dick tear through something inside of her. Libby let out a loud, quick scream and followed up with a “The fuck was that?!” It took me a few seconds before I realized what had happened. I told her, “I think I just popped your cherry.” You could tell by the look in her eyes that she realized I was right. “Wow” was her only reply.

As we continued to slowly have sex, things got easier and less painful for her. Her pussy loosened up and stretched to accommodate my dick, and we were able to really go at it after about 15 minutes. Soon, we were doing all kinds of positions and I was bending her in ways that I had always wanted to try but never really could. We were taking full advantage of our new-found college freedom and not being back home and having to sneak sex with significant others in our parents’ homes.

The sweet spot was discovered when I flipped Libby on all fours. She absolutely loved doggy-style. The only small problem was that each time I thrust into her while we did doggy style was that she let out this breathing noise that sounded exactly like a dog panting. She caught me laughing, asked what was so funny, so I told her. We went straight back to fucking, and then she heard it herself and couldn’t help but laugh, too. It was a great way for us to get beyond any sexual awkwardness and helped up become more comfortable with being vocal to one another during sex.

Libby spent the night (another first for each of us) and we continued to have sex, talk, have sex, and talk. She wore one of my t-shirts to bed and we held each other while we slept.

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? The next morning, we had sex again. I made a joke about having popped her cherry and having “scientifically” taken her virginity the night before. She quickly rejected this notion and said something to the effect of “you popped my cherry but you did NOT take my virginity.” I don’t think she liked the idea of me jokingly trying to re-write her loss of virginity.

Over the next two weeks, Libby and I were inseparable. We were always together, constantly, had sex, and thoroughly enjoyed each other’s company. We had a pregnancy scare, considered being in an actual relationship, but eventually realized that we were in our first semester of college. We both wanted to “experience college,” a.k.a. sleep around, so we agreed to spend less time with each other and see what else was out there for us.

We still saw each other every so often and had sex, but the emotional connections would always start to creep back and we’d have to distance ourselves again.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Making new friends

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? 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? My circle of friends at the dorm knew about us fucking. But it wasn’t a big deal to them.

When Libby went home during winter break, on the other hand, she was again faced with attempting to break things off with her “boyfriend.” They wound up sleeping together, and she told me in the subsequent spring semester that when he entered her, he went from being hard to completely limp and asked (without knowing about Libby and I) “Jesus, how big was this guy?” I’m not sure if that embarrassing realization had anything to do with him finally letting her go, but I like to tell myself it was.

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? Not at all

What was the BEST thing about this hookup? It was nice to have really passionate sex with somebody who was both gorgeous and incredibly intelligent. I was used to there being a direct correlation between beauty and stupidity, so it was nice to be able to have an intelligent conversation between all of the great sex.

What was the WORST thing about this hookup? Libby eventually thought I was an asshole because of how cocky I had become. I couldn’t help it, I was juggling anywhere from 7 to 10 girls at a given time and- at that time- couldn’t be bothered to treat any females with the dignity that they deserved. We eventually reconciled in our junior year, but the connection we had previously enjoyed was gone.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Libby was the first girl I slept with in college. She opened my eyes to what potential there was going to be over the next four years.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? When Libby and I reconciled in our junior year, I attempted to seduce her for one final farewell fuck. She flat out refused. She told me that since we had stopped sleeping together back at the end of our freshman year, she had to do a bunch of vaginal exercises to get her pussy tight again. She swore that she’d never sleep with me again, fearing I would permanently loosen her vagina. I guess there’s worse reasons to be rejected.

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