This post is sponsored by The T Bar.
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? Seattle
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Photographer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Queer
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? This is my third
Losing My Virginity After a College Party
How long ago did this hookup happen? 14 years ago
What was your relationship status at the time? Single
How would you best classify this hookup? One-night stand
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? She was 20, and I was 18. She was a five-foot-a-few-inches brunette with curly hair and pale skin, a bit chubby but very pretty, and quite hot. Her curves were amazing – not from the chubbiness, but because she was a naturally very curvy woman, with large breasts and very full legs – and she looked like a slightly heavier version of a younger Jennifer Jason Leigh, circa Fast Times At Ridgemont High. I always saw her at college parties, where she invariably was wearing a very cleavage-showing top and a short skirt, and she definitely caught my eye… I was an awkward college freshman, so I thought a woman this hot was out of my league, especially since I knew she was two years older – she was the TA in one of my friend’s classes. But one night, we wound up talking, and it turned out she wasn’t so out of my league after all…
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was a Freshman in college at a school in Chicago, and I was getting very tired of being a lonely virgin. I had very little luck in the dating scene in high school – I was always too shy and awkward, and none too popular with the girls. As I learned as I got older, it wasn’t that I was unattractive – I’ve been told by a few men and women that I’m quite good-looking, and I’ve come to be fairly self-confident in my appearance – but at the time I was just so timid and my self-confidence was so low that I sabotaged my own chances. I didn’t want to just get laid – I wanted a girlfriend. I was and still am a hopeless romantic; I wanted to fall in love with an amazing girl who would be equally in love with me. But after a few false starts, nothing much had happened during my first semester. In the mean time, a few of my friends had at least hooked up – including a couple female friends who I had at one point had feelings for, and their friendly boasting to me about the sexy guy they took to bed the previous night only hurt my self-esteem more, as I knew I wasn’t even on their radar. Still, the talk of casual hook-ups made me at least consider that as a possibility. Then there was this girl I had seen around at a couple parties, who had struck me as very hot – yes, she was a bit chubby, but not overweight; the kind of chubby where I found myself thinking about how soft and sexy she would feel pressed against me if we were making out. I was at a party with some friends on one of the last weekends of the semester, and after a few (in all honesty, after very many) drinks I decided to go talk to her. It was the end of my first semester, goddammit, and I was going to at least take a shot at hooking up with someone.
I was very drunk, and so was she, so I cannot even remember what we talked about. But I must have been drunk enough to be self-confident rather than timid, and apparently I did a pretty good job, because my only really clear memory as I started to sober up towards the end of the night (I have one very hazy memory of us talking on a couch in a basement, though about what I couldn’t tell you) was of us making out, really intensely. We were very nearly going at it against the wall in this party – she had me pinned to the wall, grinding against me, and I was feeling her up so thoroughly that her very large breasts had popped out over the top of her extremely low-cut tank top. Her nipples were out for the whole party to see, but she didn’t care at all – she was kissing me hot and heavy, and rubbing her hand against my cock through my pants. I suggested that we go somewhere more private, but she said that she was too drunk to feel like she should be consenting to sex tonight, and maybe another time. Probably a good decision, as I myself was just coming down from being completely hammered, to that point that I don’t even remember how the hell I managed to get so intimate with her in the first place. She left, and I went home to the dorm and jerked off thinking about what just happened. Seeing her topless(-ish) and feeling her rubbing my dick through my pants was honestly the closest I had ever gotten to a genuine sexual experience – and it felt like so close, but so far.
The next morning I woke up with a killer hangover, and was throwing up. When I finally had myself back together enough to clean myself up and start my day, I took a shower, and found myself thinking about her and jerking off again. I really, really wished I had gotten her number. I had given her mine, but why the hell would she ever call me? Then the next day, she did. She said that she had had a fun night, and she wanted me to know that it was pretty rare that she did that much with a guy she had just met at a party – but since she did, she was curious about the connection, and wanted to get together. I literally could not believe it. I said yes, of course, and when did she have in mind? She said she was free next Friday – and it worked out well, because her roommate would be out of town visiting her parents, so she’d have the place to herself. The implication of that was so obviously sexual, but I didn’t want to get my hopes up. We made plans to go see a movie and have dinner – but she said maybe instead of going out, we could get carry-out and bring it back to her place, since she’d have it to herself and it would be nice to be able to have a romantic dinner in her own dining room. We talked a couple more times throughout the week – getting-to-know-you conversations with a bit of a flirty edge – and I eagerly awaited Friday. I bought condoms just in case I was right about what she wanted. I wasn’t planning on a one-night-stand; I really wanted to have this be a real date, and for her to hopefully become my girlfriend. But I was also sexually frustrated and ready to move forward in the romantic world enough that sex on the first date sounded like an awesome idea.
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? We met up on campus that day, and walked around and talked while we killed time before the movie. Several times throughout the walk, we found ourselves making out very heavily, usually when she would kiss me as soon as she saw that we had turned a corner and were in a part of campus where no one could see. The girl knew what she wanted, and wasn’t afraid to take it. I liked that about her, since I was still a little too uncertain to take the lead. Every mini makeout session boosted my confidence, though, and I started kissing her just as much as she was kissing me. We were both clearly very horny. When we got to the movie, we were some of the only people in the theater, as the film we were seeing had already been out a few weeks. Before the trailers started, we were making out in the theater again. As I had a couple times in discreet locations around campus, I started feeling her breasts through her shirt. But sitting in that dark theater with no one in the rows behind us to see, she did something a bit different – she reached over and grabbed my dick through my pants, like she had at the party. I got hard for her instantly, and she stroked it a little through my jeans. Then the trailers started, and our making-out stopped, since she genuinely did want to see the film. But in the middle of the film, her hand reached over and touched my leg. And then touched higher on my leg. And then slid up, and grabbed my cock again. She started stroking my penis through my pants once again, and this time I reached my hand over as well, and rested it on her thigh. Tentatively, I slid my hand upwards, up her legginged thigh and under her skirt, until I was rubbing her crotch as well. She let out an “mmmmm” as I rubbed her – but then after a minute she stopped, and said, “ok, we should save this for after the movie.” I was so glad I had brought those condoms, as I started to very much suspect that this would be the night when I would finally shed my virginity.
We called a cab and waited for it to take us back to her place. As we waited, I had to ask, being the hopeless romantic that I was – was this a date, and given our passionate crotch-rubbing in the theater, might she be interested in me as a boyfriend? “I’m not girlfriend material,” she said – “no offense, but that’s really not what I’m looking for.” She meant it as “let’s just keep it physical,” but between being romantic and naïve, I took it as probable rejection – the date hadn’t gone the way she’d hoped, so she was done, maybe because I hadn’t seemed like I knew what I was doing when I was rubbing her pussy in the theater? But then the cab arrived, and as soon as it got moving she kissed me again in the back seat. Apparently things were still a go! As the cabbie pretended not to notice, we were making out in the back of the moving car. I placed my hand on her thigh again; she picked it up and placed it straight on the crotch of her leggings. At this point, there were two conflicting voices in my head. One of them, the voice of responsibility, said “you want a girlfriend, not a one-night-stand with a girl you barely know. This isn’t how you want to lose your virginity.” Then there was the other, the voice of horniness… and it said “holy fuck, this girl is holding your hand against her pussy, and this is only in the cab going back to her place! If you follow her in and just go with it, she is going to fuck you tonight.” I was 18… can you really blame me for going with “fuck tonight” over “hold out for an ideal girlfriend?”
We got back to her place, and got some carry-out Chinese, intermittently talking and making out and groping while we waited for it. I cannot possibly tell you how the conversation got there, but she somehow wound up telling me a story about the time her and her high school ex were driving around trying to find a place they could fuck, and she got totally naked in the passenger seat to tease him by playing with herself while he drove. They got pulled over, because he was driving erratically while he tried to finger her, but when the cop walked up to the window and got an eyeful of the fully-nude teenage girl with big tits in the passenger seat, he let them off with a warning. This story of her and another guy was more of a turn-on than a turn-off; she told it like “this is a coming attraction of what you can enjoy, if you want to.” Then she said “so you can tell by that story that I’m not a virgin – are you?” I said, “yes… but not because I want to be. I’d love to not be a virgin anymore, believe me.” She just smiled. Then the Chinese food showed up, and we ate.
Soon after dinner, we were making out again, on her couch – and since there was nothing else like dinner or a movie to make us hold off, we both went into horny overdrive. I pulled her shirt off over her head, and then took off her bra, only stopping kissing her enough to pull the shirt up between us. Holy shit, she looked great topless. I started kissing down her neck, to her breasts, and kissed and licked her nipples. All of this was, literally, virgin territory for me, and I was savoring every second. As I kissed every inch of that beautiful chest, I started feeling one of her thighs with one hand, again creeping my hand up under her skirt to her legging-covered crotch. This time, as we were both totally uninhibited, I could feel the heat of her arousal through the fabric – and just a hint of wetness, which was a sensation I had hitherto only read about. This whole evening had basically been foreplay, leading to this moment – foreplay carefully guided by her, scratching the itch to fuck that I think she had had ever since nearly hooking up at that party. Now, she had had enough foreplay. “Want to take this to the bedroom?” she said. Fuck yes I did!
We ran down the hall to her bedroom, and no sooner were we in the door than the tore off her skirt and leggings as fast as she could, and jumped on the bed – laying on her back, totally naked, with her legs spread and her gorgeously wet vagina on display for me. I looked at it lovingly, appreciating the beautiful folds of her labia, and the river of wetness trickling from within – I had longed for this moment for so long, and I found her vulva to be one of her most beautiful features (I am still a big appreciator of the look of a woman’s vulva – it is such a sexy part of the anatomy). She had a gorgeously trimmed bush, the same shade of dark brown as the hair on her head, standing out in sharp, sexy contrast to her pale while skin. I had always wanted to know what a woman’s pussy tastes like, so I climbed on top of her, kissing her on the mouth once again, and asked if I could go down on her. “Absolutely!” she said. I kissed my way all the way down her body, across those gorgeous tits once again, down her belly, and after a moment of mouth-watering anticipation, licked her vagina and slowly slid my tongue inside. Oh my god, she tasted even better than I thought she would – hot and sticky and slightly sweet, and I loved the way her muscles responded to my tongue sliding inside. This moment began my feeling that going down on a woman is my absolute favorite part of sex; something that holds true to this day (although I also added going down on a man to that list later in college).
I knew that as a first-timer, I couldn’t possibly know what I was doing well enough to please her properly, so I did what all inexperienced guys really should do – I asked her to please tell me what to do to make her feel the best! She explained to me how to give great oral, telling me how to lick and suck her clit, and then when she wanted a change of pace, cueing me to move my tongue back inside her, and then move back to her clit a little bit after that. I wanted to thank her when, that summer, my subsequent friend-with-benefits (who I wrote two stories on here about) asked how I learned to go down on a woman so well. Young guys – ask girls how you can best please them, and take notes! She was very instructive – and VERY demonstrative of her pleasure. I could see why she was so glad her roommate would be out of the house – she loved screaming and moaning her pleasure as loud as she could, and also loved grabbing fistfuls of my hair (early-2000s emo-bangs – my hair looked like the lead singer from The Ataris) while I was down on her. She didn’t come from the oral; instead, once she felt ready, she told me to stop and take my clothes off, as I had been in such a hurry to taste her that I had left them on. She pulled my shirt off herself, and I fumbled with my pants. Then I remembered what was in my pocket, and pulled out the condoms – half-breathlessly, in this total “hurry up and fuck me” tone of voice that really turned me on, she said, “mmmm, I love it when a man comes prepared!”
She pulled off my pants, and found herself face-to-face with my mostly-hard dick. She took it in her hand and stroked it until it was fully hard, while I rubbed her breasts with the hand that wasn’t holding the condoms. Then she laid back down on her back on the bed and told me to put one on. She idlely rubbed her clit while I did. “Are you ready to do this?” she asked while I rolled a condom on. “Yes! …what do you want me to do?” She giggled a little. “Just put it in! I think it’s obvious from there.” She slid a finger inside herself, as if to demonstrate where to put it in. I asked her, “do you prefer to be on top or be on the bottom?” “It doesn’t matter, just fuck me!” she said. I climbed on top of her, and slowly, savoring the monumentous occasion, guided myself into her. Holy fuck, I remember how unbelievable it was, feeling that sensation of a woman’s vagina around me for the first time; it felt even better than I ever could have anticipated. The slipperiness and tightness were more or less as I had imagined, but what had never fully occurred to me was just how hot (temperature-wise) the inside of a woman would be. I told her how incredible it felt, and she just laughed, and said, “I know, right?!”
I slowly began sliding myself in and out of her; clumsy at first, but more assured once I figured out the best motion. I still couldn’t get over how great it felt, and the first stretch of it had an oddly surreal and out-of-body “holy shit, I can’t believe I’m actually having sex right now!” disbelief hanging over it. I was pretty nervous about wanting to do a good job – which I ironically suspect is what allowed me to last as long as I did. The nervousness and slight performance anxiety stopped me from getting close to orgasm too fast, and I lasted a good ten minutes or a bit longer inside her; pretty good for a first-timer, I think. I had nothing to worry about when it came to doing an ok job, though: she started responding very positively quite fast. She moaned so loudly, and grabbed me so hard – squeezing me close to her with an arm around my body, and grabbing a fistful of my hair with that other hand. Grabbing my hair by the fistful was the big thing she’d do when she felt really good, and it was totally hot. I asked her again to please coach me on what to do right, and she would ask me to vary my speed when she wanted a bit of a different sensation. Sometimes she wanted a nice slow rhythm, and sometimes she wanted to be pounded very fast; she liked to switch up the pace. She got on top for a bit, which felt fucking fantastic, but soon she flipped us back around, saying that she liked it when I did all the hard work. After a bit of very hard fucking at her request, I had to pull out altogether, as I was getting too close, and neither of us wanted me to come yet. I just fingered her for a minute, and then once I knew I was safe again, I slid back into her – again nervous enough about coming too soon that I had to focus on pushing the anxiety aside and getting back to the sex and hand; an oddly good longevity aid.
She knew we were reaching the limits of how long a virgin could last, though, and she wasn’t about to let this sex end without her having an orgasm. She reached down and started rubbing her clit; she wasn’t going to leave her orgasm up to me, which was totally fine with me, since I wasn’t sure I knew how to bring her to orgasm without her how-to. I again found her straightforwardness with taking what she wanted extremely sexy. She moved herself around me as I moved myself within her, and made increasingly loud moans as she was getting closer. That got me closer too. She asked me to fuck her hard again, and I did, with pleasure. “Are you ready?” I asked her, as I could feel my own orgasm start to build. She didn’t say anything – just gasped and moaned as we thrust together and she rubbed herself. Then she screamed, and I felt her orgasm explode and tighten around me. With literally the first muscle contraction of her orgasm, I came; it didn’t take much. I came the hardest and the longest that I had ever come in my life up to that point, and filled the condom inside her as her muscles continued to spasm as she kept rubbing herself. She was on a roll, and I kept myself inside her after I had finished as she kept her orgasm going – she had more than one, though I was too in a daze to count (I’m not trying to imply that I was any great lover, for the record – at this point, this was largely her giving herself extra orgasms since she really wanted them. Still very hot for me tho!). Then we kissed each other deeply as she grabbed my hair once again to pull me close, and I slid myself out of her, officially no longer a virgin. I pulled the condom off and threw it in her trash can, and we laid there together for close to another hour, making out and talking. She told me how I did, and gave me some pointers for next time, and at one point the conversation turned so sexy that we both got turned back on, and I wound up going down on her again, and making her come one more time.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, 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 rest of the night was just as positive an experience as the sex itself. She was quite honest about how I did, and genuinely helpful in her tips for how to improve as a lover. At the same time, she was quite self-confidence boosting – she told me (I think honestly) that I did much better than the couple of other virgins she had been with, both in terms of longevity and in terms of actually figuring out what worked and taking direction. Sure, being a better/less-bad lover than typical virgins may be a fairly low standard in the grand scheme of her experience, but it made me feel really good that I had at least done a decent job my first time, hadn’t come too fast, and helped her reach a few good orgasms. The shy, awkward sense of not really knowing how to approach college romance had been replaced by a somewhat raised level of self-confidence; she had made me actually feel sexy, which I certainly wasn’t used to. When we said goodbye I asked her if she’d like to go out again and maybe give me a few more lessons in the bedroom. She said definitely! I walked home feeling great – about the night, and about myself.
But it turned out that she really wasn’t interested in a second date after all. I called her a couple more times before we went home for the winter semester break, and she was fairly distant and came up with reasons why she didn’t have time for a date. I talked to a mutual friend, and she told me that that was just this girl’s style: she liked simple one-night-stands if the guy wasn’t someone she thought was boyfriend material, and she didn’t like giving a second night to a one-night-stand, to stop things from getting complicated. Either she had meant what she said about a second date but thought better of it (probably not, but I had hoped it at the time), she didn’t plan on one at all and was just trying to be nice, or she was just trying to avoid drama and not end the night with bad feelings. Whatever the reason, it looked like she never really planned to see me again after I left that night. Yes, she had said earlier on that she didn’t want a boyfriend, but I couldn’t help but feel lead on by that conversation before I left. I felt very hurt – and even more hurt when over winter break I heard through the grapevine that she had found a new, more serious boyfriend, maybe just three weeks after we had slept together; I couldn’t help but wonder what had made me so unworthy.
I felt very hurt over it for a while, but eventually I put it into perspective: aside from that misleading last conversation at the end of the night, she had been totally straightforward with what she wanted, and I agreed to it, even if I had been thinking more with my dick than with my mind. She hadn’t really been dishonest about what she was looking for, and she had every right to want to get off that night with an equally eager partner. It was, ultimately, my fault and not hers that I had gotten more attached and wanted more than she clearly told me she wanted to give. I wish she had been more clear at the end of the night, but I don’t think she was trying to hurt me; just not end the night on a down note. The hurt subsided and the added self-confidence I gained from the experience came back. Once I had sufficient time to process it all, my feelings about the experience wound up being very positive: despite the unintended pain that it caused to me, it had been a night of great sex, from which I had learned a lot. Aside from getting an actual girlfriend, I don’t think I could have asked for a better experience of losing my virginity.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, It was easy / convenient
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? I was very excited to tell some friends about this. I compared notes with some friends on their losses of virginity, and talked to just a couple especially close friends about how great the experience had been. As I mentioned at the beginning, she had been the TA in one of my good friend’s classes, and when some time later he was in a situation where he thought he might get to finally lose his virginity to a woman, I got the amusement of being able to say to him, “here – take these extra condoms I still have from when I had sex with your TA!” We both got a laugh out of that one.
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? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? The sex was fantastic, and she was such a good lover! I cannot deny that I still sometimes masturbate thinking of sex with her, even a decade and a half later: she was so passionate, and the way she communicated so clearly both verbally and in terms of moaning, screaming, scratching, and hair-pulling was so hot! I could not have asked for a better lover to lose my virginity to.
What was the WORST thing about this hookup? …However, I could have asked for a lover that would have wanted more than just a one-night-stand, or had at least communicated her intentions (before and especially after) as clearly as she communicated what she wanted in bed. I wish I hadn’t gotten so hurt by the situation at the time, although with time the hurt has faded and only the good things about the night remain. Really, I just wish I hadn’t been so naïve, and had been in the same frame of mind that she had been in. At this point, the worst thing is that I never got to sleep with her again – I really, really wish we could have at least fucked another time or two before the semester ended.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Once I got over my initial hurt feelings, appropriately processed what happened, and stopped being so naïve, I was left with a very positive feeling about hooking up: if the chemistry is there, two people absolutely can get together for fun, spontaneous sex that can be really, really hot without being emotionally complicated. She made me more self-confident, both in my own attractiveness and in my ability and knowledge of how to please a woman; this was only the first lesson, of course, but she was a very formative part of making me the guy I am, who loves to give partners multiple orgasms, especially through oral, and has gotten very good at it. I learned a lot from her about sex – partly in terms of technique, but more broadly about how sex can be loud and wild and fun and passionate: she fucked like it was a party, like the sex equivalent of dancing like nobody’s watching. More people should have that kind of sex – it’s so liberating!
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little 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? People need to be more open and honest about both what they want in sex, and actually doing more of it! We need to make relationships – romantic ones or casual flings or fuck-buddies – safer places to talk about what we want and then actually explore those desires, as people do on here. Communication and especially consent need to be standard parts of every conversation about sex – and along with that, we need to build a standard of sexual equality, as I learned in this first sex experience, where a woman’s pleasure and orgasms are every bit as crucial as a man’s, and women have every bit as much a right to want to fuck without being judged or faced with a double-standard. There’s no excuse in the world why both partners in a sex pairing shouldn’t come, or why either partner should be judged more harshly for wanting a fling.
What do you think about the Casual Sex Project? It’s great! I love reading everyone’s experiences – emotionally and intellectually it is so fascinating and eye-opening to get these windows into everyone’s experiences, and sexually I cannot deny that the stories and the level of intimacy that they represent are often very arousing (I always leave this site turned on). The community of honesty and openness that has been created here lets us share our experiences and find things in common with others where we may have felt alone; it really is a social good in our repressed world. And that the stories can leave us as aroused as we are enlightened is a definite plus!
I know that this story was very long, but this is literally the first and only place where I’ve felt I could just share the whole story of my experience of losing my virginity, without feeling like I needed to hold back, so I figured I might as well share it all! Even if people find it too long to read it’s great to just be able to say it to a group that might read it.
You have a hookup story to share? Submit it here!