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The Daily Grind

Losing Your Virginity: Fiction vs. Reality

In so many romance novels, when women lost their virginity the pain only seems to surface for a second before feelings turn into earth shattering pleasure. However, in real life woman usually doesn’t have a whole lotta fun and it takes a couple of tries to get the earth shattering feeling that these romance women get in just a few seconds. Did anyone out there have romance book type experiences where the guy knows what he’s doing when it is her first time? Did the pain quickly turn to pleasure?

How about the guys? Men are almost always portrayed as knowledgeable and experienced. We know that’s hardly the case. Don’t be shy, tell us: Were you nervous, uncomfortable, was your partner helpful, or scornful? —Alyn Rosselini

I always thought of losing my virginity as a career move. —Madonna


  1. Comment Import

    From Lov3r
    Losing it at 27, I was a bit of a late bloomer. Partly because of culture, the rest was personality I guess. It was roughly 6 months into the relationship and we were both virgins. We’ve done a lot of fondling, kissing and oral before, but I didn’t really try to initiate in real intercourse until she asked for it.

    The very first time, we only managed like an inch and stopped because she was feeling pain. To my surprise, she wanted to try again the next time we got together. She had done research and was told that it would be better for her to be on top since she could control the speed and movement better. It was a mind-blowing experience for me, feeling her warm wetness while staring at her back and gorgeous ass as she crouched above my penis and slowly impaled herself on it. She said it kind still hurt a little but she could take it and didn’t bleed. As she started pumping up and down I felt my orgasm quickly approaching. Luckily we both had the sense to pull out before that happened.

    The next time we did it better prepared, with a condom. This time she did bleed a little, and she didn’t orgasm from it so I had to finish her off with my tongue. It took a couple of tries before we got into a familiar and comfortable pattern. We usually end it with her being on top. Condoms prevented me from coming before her, but she was always patient to continue pumping and grinding until I (and sometimes she again) came.

    We are no longer together for too many differences came between us. It didn’t end very well and both of us have had other partners by now, but if there was anything right about our relationship, without a doubt it was the sex.

  2. Comment Import

    From Knox
    I was 20 my first time. We were in college and had been a couple for over a year. It happened in my car. She was not a virgin, the result of a teenage one timer (so she said) with a sailor on shore leave. It was practically rape according to her. Anyway, I wore a condom. Penetration was problem free. An average cock in an average cunt, so it slipped right in. No instant ejaculation. I lasted a few minutes. I don’t think she came, but I certainly did. It was more rite of passage than sexual pleasure. I’d had much stronger orgasms masturbating.

    Of course I was excited afterward because I’d finally done it, but, in retrospect, it wasn’t much. I was pretty naéve at the time, but I now realize that a transaction occurred. In her mind, I’d traded my freedom for a few moments in her priceless pussy. I think the code word is “commitment”.

  3. Comment Import

    From J
    Really, the only thing I don’t like about my first time was that I had to wait until I was 25. But then, had it happened when I was a teenager it wouldn’t have so good. For one thing, as we were both adults at university we didn’t have to worry about getting caught since we were in her bedroom in her flat. She was really nice to me, very patient (the first two times of putting a condom on me resulted in loss of erection!), and helpful at the vital moment by reaching down to guide me in.

    Of course she had to tell me to slow down, but also told me to let her know when I was coming so she could orgasm with me. A remarkable skill to have! Sadly our relationship only lasted about four or five weeks, but we had a pretty good sex life in that short time (but then I would say that; I had catching up to do). I still miss her – although we are still just about in touch by email – and would love just one more decadent afternoon with her, even though it’s 25 years later.

  4. Comment Import

    From Doug
    I was 20 years old in the summer of ’68. My experience was totally different than anything else I had seen here. I had been hanging with my girlfriend for 9 months at college and now home for the summer. She decided that I should not remain a virgin much longer. She set it all up, the music and refreshments. She included some psychedelic refreshments of the time.

    As we lay there on the bed we were playing around and I got a very firm erection. She straddled my body and put the head of my penis into her about an inch and just danced a little around it. Eventually I was all the way in. She moved very slowly and found a deep spot to rub against, very slowly. After a while she started groaning and grunting and each time she contracted that caused my penis to contract as if I was coming which caused her to contract again and me in turn, over and over. She sat there with my body sort of flip-flopping under her in an orgasmic feedback the likes of which we never had happen like that again.

    I kept that erection and couldn’t stop orgasming with her. It was a most amazing psychedelic orgasm, inconceivably great first time and never equaled since. The next day we were both so totally sore that we both had trouble walking.

  5. Comment Import

    From Boris
    As a male, the first attempt at losing my virginity was fraught. It was a freezing cold night, we sought a spot to make love, choosing the backyard vegetable garden of my wife’s parents. She (now my wife) lay down on her back at her initiative, with me kneeling in the missionary position. My penis had not touched her, when I had to turn away gushing and squirting fulsomely into the frosty night air. My embarrassment to this day is great and abiding.

    The next time my virginity was tested with her was one Saturday night at my parents home, heavy rain drumming on the corrugated iron roof. Again we used the missionary position, but this time, not only did I enter her full length slow and easy, but amazingly, also managed to stroke rhythmically for about five minutes without the clamour of premature coming. I pulled out just before spurting my semen.

    My wife thrilled me by saying how wonderful it was. I certainly thought it was. I can still feel the full-length strokes and smoothness to this day, see her breasts jiggling as I thrust into her.

    Nearly 50 years later, we are both still keenly at it, still with utter delight for both, using a wide range of confident and secure sexual expression. Bravo!

  6. Comment Import

    From Anonymous
    I was nervous. Mainly because of hearing about pain and bleeding and such but I had NO pain, (yes, I was tight and it took some effort and stretching for him to get inside all the way, but no pain) no blood. No soreness that I recall the next day. And the next time no discomfort at all either.

    I really wish I had been able to relax more and not have had these ideas in my head. Would have been much better. But apparently, many girls DO have some or even a lot of pain, so I won’t say those stories were “myths”, but for me, as it turned out, they did not apply.

    I’ve read that there are vast differences in hymens between different populations and individuals within populations, to the extent that some tend to have very thick and pronounced hymens, and others tend to have little or only a residual hymen. According to this study, ALL girls have a hymen, even if it is virtually undetectable and with no need to be torn.

    Anyway, I didn’t come (but then, I don’t come from intercourse alone even now, I need clitoral stimulation instead or along with penetration) and that first time, we were both so focused on the intercourse aspect that a few kisses aside, nothing else was going on! It wasn’t a “fairy tale” scene, a bit awkward and sort of anti-climactic, all in all. But wonderful still, very intimate and pleasurable (not orgasmic for me, but yes, felt good to have him inside me.

    This is an awesome forum! So great to read everyone’s experiences.

  7. Comment Import

    From Anonymous
    Wow…it really makes me feel so much better reading everyone else’s postings. I was greatly disappointed. It was nothing like I ever imagined it would be. I didn’t know the guy as well as I should have, not that he wasn’t great. But I felt that it was a mistake. It hurt, quite a bit, and I was drunk. Wrong thing to do.

    Afterwards I slept, but woke up about an hour later…and felt paralyzed. Not really knowing what to do with myself, and feeling sorry that I started the whole thing in the first place. Too spontaneous. I felt like I let him down somehow because it wasn’t the fairy tale that I thought it would be. Am I crazy?

  8. Comment Import

    From Mary
    I’d like to get my hands on the guy who took my virginity when I was a mere 15, he was 28. What did I know? Nothing. Yes the jerk was considerate, right up to penetration, then he went at it like a sex starved cave man.

    One minute he’s all like nice and gentle, and I was feeling a real nice sexual buzz, and the next minute he’s slamming into me like a steam hammer and it hurt like hell. Then he’s coming and groaning and grunting like a sweaty pig, cleans up and he’s out of there like bat out of hell. Jerk. And he’s got the nerve to call a week later – a whole week! Looking for more sex no doubt. I told him to eat shit and die.

    I guess I should be a bit thankful. He taught me to wise up, wait until I really know the guy before becoming lovers. A good man is worth waiting for, girls. Don’t waste your sexuality on idiots who think with their dicks rather then their brains.

  9. Comment Import

    From ETM355
    My first time was probably a little later than most guys. I was half way through my junior year of college. I had been dating my girlfriend for a couple months. We were in her dorm room. I didn’t ‘ ask if she was a virgin and didn’t volunteer that I was until later. I loved kissing her, especially her breasts. By the time we had all of our clothes off, I was so turned on. She took my cock and guided me into her. I couldn’t believe how warm and wet she was. The feeling just overwhelmed me and I came after just a couple strokes. It was a little embarrassing, but she was really nice about it.

    When I told her later that it was my first time, she said she wished I would have told her because she could have made it better. A few weeks later, I found out what she meant. She masturbated me to an orgasm first. Then when I got hard again, she got on top of me. She started really slow, and gradually built up until I came with a lot more intensity. I felt her suddenly tighten around my cock. When looked at her, she was a little sweaty and were breathing was just getting back to normal. That ‘a when I realized she had come just after I did.

    It was a much more satisfying experience for both of us. We dated the rest of that year before splitting up. My first time was more memorable for how understanding my girlfriend was than it was the actual experience itself. I will always be grateful to her for that; as well as showing me how great sex could be the second time we did it.

  10. Comment Import

    From Another Male Perspective
    Just thought people might be interested in another guy’s first time experience – thanks to the first one for breaking the ice.The woman I got it together with was eleven years older than me and very dominant. I just didn’t feel like I had any way out. Let me put it like this: I didn’t have to fake orgasms, but I did have to fake enjoyment. (I’d say a lot of porn actors do the same; it can’t be that much fun having sex in a brightly-lit studio, especially when there’s a bunch of guys standing around.) What baffles me is how I got involved with her. I guess I was pretty insecure; a lot of guys are in their teens.

  11. Comment Import

    From Liz
    So many women say how they bled the first time they had sex, and it hurt at first and the hymen broke and all that jazz. I never bled or felt pain when I first had sex. The only time I feel discomfort is when a guy goes in before I’m wet enough. So I guess I’m just different. Either I never had a hymen, or mine is just really stretchy. Or maybe I broke it by accident as a child, and I just don’t remember—although I think I would remember something like that.

  12. Comment Import

    From Sheila B
    Well well well. Losing my virginity was hell. My first time was at my sister’s graduation party (at the time I was 16 and still a virgin). The boy I was mooning over (he was 18) for the past couple of years was finally paying attention to me. So I started playing big girl by drinking and dancing and flirting with older guys (much older guys). Anyway, it was nearing time for my curfew so I went on the porch to get my bearings together and low and behold this boy decides to come out as well. I was 16 so I was extremely naive he started saying how he always liked me and I’m different from all those other girls. And we started kissing and lifting my skirt.

    Conveniently the porch was connected to a bedroom (now how did he know that) we stripped and he kissed my breast and went lower on me. It felt good. But when it came down to the actual penetration it felt as if I was punched in the gut. And I seriously thought having my period was bad but that was terrible. He pulled out just before he came. And then he toppled right over me and a few minutes later went to sleep. I was up and decided to push him off of me. My mistake he woke up again and this time when I said no I have to go he laughed held my hands over my head and did it again.

    When school started again I noticed the whole foot ball team was making a pass at me (strange isn’t it that before they never noticed me) and every time I looked the boy in the eye he smiled and looked away. But that was my story.

  13. Comment Import

    From Bernie
    I lost my virginity at age 17. My girlfriend was 19. She was a virgin too. It was in the front seat of my Ford Pinto. I know those of you who remember that vehicle are wondering how that happened. It was on desolate dead end street of a housing development under construction. I think it hurt her a little but not for long. Subsequent sessions were much better. I didn’t last very long. As I ejaculated a pall washed over me as the words of my parents telling my sex was bad echoed in my head. Hormones were stronger then my parents words though.

    Sex for me and sex for her were different. I was a young man with raging hormones, yes, but a plan for my future. The future included college and career. Was I in love and did my future include her? I hadn’t thought out the relationship that far. I was sincerely in love at the moment. She had apparently thought about the relationship and her career. Her career was me. I think the moment we had sex, she felt like we were going to together forever. The reality was neither of us were mature enough to know what we wanted forever. We were together about six or eight more months before I graduated and headed off to college. I broke it off before I left for college. It ended badly. I didn’t miss her and still don’t.

  14. Comment Import

    From Christian L. Ambrose
    I did not experience pain myself and there were no huge fireworks. It was also incredibly awkward as it was his first time too. He kept falling out and other weirdness so we finally gave up, snuggled, talked and eventually drifted off to sleep. The next morning, I climbed on top and went for a ride until he came, which didn’t take long at all. It was interesting and sex did get better as we both learned more about it from personal experience. I did not expect much in the way of fireworks and did expect a little pain.

    Sex is a lot of fun and I have had some great orgasms but I wouldn’t say it’s the best thing in the world. Another friend equated it with a full body massage and she is kinda right. I still enjoy snuggling and talking more than sex. Having said that, I don’t anticipate returning to celibacy anytime soon.

  15. Comment Import

    From Jerry
    I lost my virginity at 15 years old by my mom’s friend who used to stay with us at times. Some say that this type of thing does harm to a young man, but I can only say that after that first time, I was in love with her and I learned how to make love, including oral, to a woman. This woman is 24 years older than me and is still very beautiful, but she is now happily married. She will always be important in my life and I will always love her. I think my mother can somehow feel how much I care for this lady.

  16. Comment Import

    From Anonymous
    I’m 29, and I gave my virginity away to one of my brothers’ best-friends (who is 36). He is my first true love! He was so gentle and pleasing; I actually came before intercourse. Ooh, he gives such good cunnilingus! Anyway, before we began intercourse, he kissed and licked the entrance to my vagina (I’ll never forget the sensation!) and rubbed his erect penis against my clitoris moving me into another orgasm. In the middle of this orgasm, he squeezed my clit as he slowly entered my vagina. The sensation sent me over the edge and even though I felt the fullness of his penis, I felt no pain. When he began thrusting, I surprised both of us by contracting around him until we both came.

    That morning, I was very sore. After we did it again and slept a few more hours, he drew a warm bath for me and massaged all my sensitive areas. I never imagined my first time to be so beautiful!

  17. Comment Import

    From Anonymous
    Losing my virginity sucked in the worst way. I was 15, at a party and had fallen asleep (passed out?). Next thing I knew my “date” was pushing himself inside me. Yes, this is date-rape folks. Not fun. I don’t remember bleeding but I can tell you it hurt for days and I could barely sit the next day. When I finally did choose to have sex I had no problem being intimate at all. That surprised me because my first experience was so horrid. My first “chosen” experience was kind of awkward but he was older and had more practice so was able to help me along.

    I kind of envy women who choose when and to whom they wish to give their virginity to. When I read those romance novels (past-tense) they piss me off because they just seem so phony. I know my experience was hardly the norm (although I’m shocked at how common date-rape actually is) it still doesn’t seem like anyone could not just scream from the pain of it. I guess it’s true for some people though since I’m reading about here on the site. Anyhow, those are just some of my thoughts on it.

  18. Comment Import

    From Teresa
    I always found the concept of virginity kind of baffling. My first boyfriend and I did practically everything together except intercourse (mostly due to lack of birth control). And somehow because we hadn’t done that one specific act we were virgins? Silly.

    I think because we were so comfortable with each other that when we finally did “lose our virginity” it wasn’t painful. I found it kind of weird, not really exciting, except that watching his response was fun. It wasn’t until much later, when I went on the pill, that I began to understand the appeal of the whole thing. I think anxiety about pregnancy plays a role in women’s feelings about intercourse.

  19. Comment Import

    From Fred
    My was not the ideal situation. I had been friends with this girl and we would fool around some when we got together. Nice kissing and she let me feel her tits which were wonderful. One night we got together and ended up in her bedroom. Unfastened her pants and pulled them off and had her in just her panties. She insisted my pants come off and she also pulled off my boxers. Soon I had her panties partially down and had full access to her pussy.

    Nice fingering and she was so wet. Soon we were humping and it felt good sliding my cock against her pubic hair and mound. We had a nice motion going and I felt my orgasm coming and couldn’t stop it felt so good. Soon I shot loads of cum and had a great release. Found out later that my cock had actually slipped inside her pussy and we were fucking which is what made me orgasm. I wish I would of realized that it was my first fuck at the time. Would be years later that I realized what had really happened and that the change I had felt on my cock was it slipping in her wet willing pussy.

  20. Comment Import

    From Daniel
    Guys are nervous too. I was young when I lost it, I just wanted to get it over and done with, so I rushed and made a embarrassment of myself, I felt nervous scared and excited all at the same time, I was more worried of what the girl thought of me and looking like a idiot than anything else. And wouldn’t you know, I ended up looking and feeling like an idiot.


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