Taking My Ex’s Virginity

by WeCanPretend

What’s your gender? Man
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? United States
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? None

Taking My Ex’s Virginity

How long ago did this hookup happen? 3 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

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? My partner was a girl I had dated for about a year. We started dating the summer after junior year in high school and it wasn’t a great relationship. I was insecure so I felt the need to stick with her even when she was not the best to me. To this day I still have suspicions that she may have cheated on me once or twice. We were all about each other’s bodies though. I was a soccer player and had a toned and athletic body and she was a dancer so she was good looking as well. She had a pixie cut which I was super into at the time and these big brown eyes that just screamed “do me”. She was curvy in all the right places and toned in the ass. She also had some nice big tits. We fooled around the entire time we were dating. We were both virgins so we didn’t go all the way but we did pretty much everything else. We broke up at the beginning of the summer after we graduated and I started messing around with other girls like immediately afterword. I even lost my virginity to one in the back of my car. She also started talking to this other guy who was a weirdo and turned out to be bad news in the end (and I’m not just saying that to make him look bad he was seriously creepy). Anyway after some back and forth we decided to try and rekindle our friendship and by mid-summer we were hanging out again casually, not hooking up. Although I definitely still had feelings for her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was in her house. We were sitting on her living room sofa and her mom was gone. Her mom had always left us alone when we were dating and there’s no way she didn’t know that we were messing around I guess she was just okay with it. Anyway we’d finished some dumb TV show and we’re talking on the couch and we get on the subject of sex. She reveals that she hasn’t had a partner since we broke up and asks me what having sex was like. I told her from my experience and she’s getting more and more worked up. She gets her sex face on and goes right for my pants

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? She unzips my fly and pulls my underwear down. She grabs my dick and I immediately get hard (I’ve always gotten hard easily). She looks me dead in the eyes and starts pumping. We kiss for a little and while she pumps with both hands (my dick isn’t that big she just liked to use both hands) I reached up her shirt and fondle her boobs a little. Her nipples didn’t really stand up when they weren’t erect so it was always fun to get them to show themselves by playing with them. She starts to blow me and was always really good at giving head, she’d started experimenting with it on me after she got her braces removed at the beginning of junior year and had become really good at it. While she’s blowing me a reach a hand down her pants and finger her from a pretty awkward angle. She eventually takes my pants fully off and gets down on her knees in front of me to continue blowing me. She pauses to take her shirt off and I undo her bra while she’s still going to town on me. I tell her I’m going to cum and she stops. She removes her pants and panties (she’s now completely naked) and lays split legged in front of me on the couch. So I finger her and then eat her out for a little while and she came (she always orgasmed super easily, it usually only took a few minutes of fingering or oral to finish her off), but she also had amazing stamina and once orgasmed about 5 times in an hour when we were fooling around. After she orgasmed, she stood up and pulled me up with her. She took my shirt off and we started kissing naked in the middle of her living room. She paused and looked at me with her “do me” eyes and told me she wanted me to take her virginity.

After I agreed she led me to her bedroom and lay across the bed, presenting her pussy to me. Her bed was up on risers so she was the perfect height for me to enter her. I fingered her and ate her out some more and she orgasmed again. She told me she still wanted me to fuck her and that she kept some condoms in her drawer if the situation ever arose. So I pulled one out and slipped it on and entered her. We took it slow for a few minutes while she adjusted to the pain. Eventually, she told me to start speeding up and after a little while, I was going full force. The bed was rocking back and forth and I thought it was going to fall off the risers. Her tits bouncing in front of me was an amazing sight to behold and she was gripping her sheets for dear life and screaming the whole time (she was super loud whenever we messed around too. After a few minutes in that position, I lay her on her side and threw her right leg over my shoulder and screwed her sideways. After a few minutes of that, I told her I was going to cum so she told me to pull out. She got on her knees in front of me and removed the condom and blew me. I told her I was going to cum again so she pulled my cock out of her mouth (she was always afraid to swallow, which was odd because one time she was jerking me off and I finished all over my stomach, back then I had some really nice abs, and she licked all the cum up from where it had fallen between the ridges, so idk why she wasn’t cool with me just cumming in her mouth but whatever) and presented her tits to me, I jerked myself for about 15 seconds before finishing on her tits and neck (which I had done many times before).

She then got up and took me by the hand to the shower to clean up. We fooled around a bit more in the shower. I fingered her and she stroke my cock. She told me that she was disappointed that she didn’t orgasm during sex so I told her I would fix that for her and did her from behind in the shower. Shower sex isn’t that glamorous. It’s kind of cold and the wet slapping is worse that the body farts during regular sex. After a couple of minutes, we stopped cause she was afraid of me orgasming with a condom. Even though she later told me she was on the pill at the time she was still super cautious about not getting pregnant which is a good thing. So we hopped out of the shower and dried each other off. We then returned to the couch to finish up. She rode me this time both cowgirl and reverse cowgirl. I did her doggy style and she gyrated her hips and twerked on me (she was a great dancer with a great ass so this was probably the best part) and she orgasmed after a few minutes. She then blew me one last time and I finished on her face (which was her favorite place for me to finish). She washed her face off in the sink while I fingered her from behind until she had another orgasm. She told me she was exhausted and we got dressed again. I left a few minutes after we got dressed because I was afraid of the awkwardness of seeing her mom. And that was my second time ever having sex. It was way better than my first time in the back seat of my SUV.

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? Afterward, we messed around a couple more times. We kind of screwed one more time in the dressing room at a mostly empty department store late at night. I stuck it in and thrust a couple of times but she wasn’t able to keep quiet so we abandoned the plan. A couple of weeks after we first had sex, she got mad at me for something I said and threatened to go date the weird guy she was still talking to. I got upset because I still had feelings for her and felt like she was using me as a safety net so I left the house and we didn’t talk to each other for a while after that. We made up later and actually sat down for dinner this summer. We hit it off really well and went up a couple more times before we ended up fucking again, this time in my bed. I could tell some of her sexual tendencies were due to lack of experience because she didn’t orgasm once and was much less loud despite the fact that we were alone in the house. The day after she called me and told me had a boyfriend and felt terrible about having sex with me. I agreed not to tell anyone and let her handle it and we haven’t spoken since.

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

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, To feel more confident, Just happened, I don’t know why, just went along with it

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? 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 talked to my friends a couple times about it. They mostly liked that we were exes when we did it, which I guess they thought was scandalous.

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

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

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? Because I figured if she wanted me to take her virginity (which had always been important to her before) it meant we would soon start dating again, but it seems like it was kind of only a power play or just a heat of the moment thing. She’s never told me if she planned it or if she just got horny and wanted me to fuck her before her new guy did.

What was the BEST thing about this hookup? It was like a fantasy come true. I’d had a crush on this girl for most of high school so when we started dating it was great. I’d fantasized about what sex with her would be like since we was a dancer and everything and it was everything I wanted honestly.

What was the WORST thing about this hookup? The fact that it meant nothing to her in the end.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve never had casual sex when feelings are only one-sided before, because I realized that brings a lot of baggage with it.

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

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

Anything else you want to add about this hookup? Eh

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? Eh

What do you think about the Casual Sex Project? Eh

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