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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 Anonymous
    My first time was not the best way one should lose their virginity. I was 16, and he was 23. He wasn’t nice or understanding about the whole situation. He pressured me into having sex with him until finally one night I did.

    It was the most horrible night of my life. He wasn’t on the small side so that was one thing going against me…he barely got the tip in good. I tried to push him off because it hurt so badly, but he didn’t stop. After he finished I got dressed and went home. I was soo sore and I bleed for 2 weeks after that, and every other time we had sex. I truly regret it till this very day, but I can’t change the past.

  2. Comment Import

    From Suzie
    I lost my virginity to a small vibrator…hardly the fantasy scenario. That did hurt – a lot, but really turned me on as well.

  3. Comment Import

    From Jane Noel
    Owie, owie, owie that first time. He went where no man had gone before slowly and considerately (I had a really wonderful guy in my life at the time) and sex got much better within a week or so. But the first time? That hurt.

    I did have someone who knew what it was like to make love to a virgin, and for a teenager, he had a lot of self-control. (No mad thrusting!) I was really lucky, considering most of the girls I knew lost their virginity under much less joyful or caring circumstance. I feel like the exception, not the rule. We planned our first sexual encounter (more exception than rule again) and I was already on the birth control pill by the time The Deed was done.

    But the pain lasting but a moment, then earth-shattering pleasure? Nope. When I read those stories where the pain only lasts a moment, then ecstasy descends, I usually snort. In derision.

  4. Comment Import

    From JT (Sweden)
    Despite being shy, nerdy and insecure during my teens and early twenties this Swedish male eventually turned out ok (I’m now 40, a physician and considerably more self-assured) and part of that was due to the confidence boosts my first sexual experiences gave me. I had read enough on the subject not to feel completely lost or fumble-fingered but to this day I am still amazed at how easy and natural it felt when the day came.

    I was 22, madly in love for the first time with a beautiful visiting Israeli girl, and on that day I received not only my very first kiss but then she also guided my hand to her breasts. I ended up not only getting to adore her stiff dark nipples but also to fully explore her orally, an act I of which I had dreamed ever since I first learned the concept of cunnilingus. Suffice to say that worshipping the wetness between her silky thighs was the most beautiful experience of my life! Alas, she had to return to Israel (although we would stay in touch for many years) and I thus technically remained a virgin, but in my mind that day would forever be My First Time even though I never even got out of my pants.

  5. Comment Import

    From No Pain, Much Gain!
    Ladies, ladies ladies. Do not ever have sex if you are not ready, and truly in the mood. Being mentally and emotionally prepared for sex is the only way to have a pleasurable—at least non-painful—first experience.

    I lost my virginity during a one-night-stand with a sexy, confident, experienced and satisfying man. It was the 2nd semester of my freshman year in college and he was the best friend of my friend’s boyfriend. We never talked again, but that evening remains one of my most enjoyable sexual experiences. He was approximately four years my senior (22), and very smooth. Foreplay is key—good foreplay! He did not know I was a virgin, but continued to take his time to get me in the mood. To make a long story short, I was extremely aroused before he went below the border. By the time he started fingering me, I was so wet and so open, I could hardly feel his fingers, and believe me—my pussy was tight. By the time his penis finally entered me, my mind was reeling! As soon as he entered and began thrusting, I felt like my head was going to explode. I can honestly say that I’ve never had such a (near) orgasmic experience since then (kind of sad, I know).

  6. Comment Import

    From Emily
    I lost my virginity to my boyfriend of about two months. We actually did it in his car (classy, right?). I’m glad to say that despite the location, it was overall a positive experience. I told him I was really nervous, and he told me that he was too, (he was a virgin as well). He left the final decision up to me, which I think was really respectful. After removing our underwear, we held each other for a minute, which gave me some time to mentally prepare for what was about to happen. It didn’t take too long for him to penetrate me the first time. It hurt so much that I dug my nails into his back and gritted my teeth. But even though I was in pain and did not have an orgasm, I had this amazing feeling of closeness and trust with him that was like nothing I had ever experienced.

    And now for some advice for those thinking about loosing their virginity: Before you have sex, I think the most important thing you and your partner need is mutual respect and trust. Sex is a big deal, so don’t do it until you feel completely ready. If your partner pressures you or tries to rush you, that’s a sign that they only care about themselves, not about you or your feelings.

  7. Comment Import

    From Anonymous
    I lost my virginity when I was 16 years old to an older guy. After the first few minutes of pain…it hurt so much I had to scoot back on the bed so I could breathe for a second. He didn’t get in all the way and we didn’t have an orgasm, but I bled. My first time is something I’m not too proud of because I felt that I should have waited for that special person. I cried a lot that night…he wasn’t anything to me and I wasn’t anything to him either.

  8. Comment Import

    From Stacy
    I was 14 when I lost my virginity. To be honest, it was with a guy I had just met (he had no idea I was a virgin). A total one night stand. I was (and still am) an avid reader of romance and erotica stories so I was expecting fireworks and for the earth to move. None of that happened and I was highly disappointed.

    Highly disappointed that is, until I met my steady high school sweetheart about a year after I lost my virginity. He was the first one to bring me to orgasm. The earth really did move and I really did see fireworks. I’ve LOVED sex ever since.

  9. Comment Import

    From Joni
    I was young when I lost it to a very loving and gentle man. He took the time to make sure that I was ready and when he gently put it in me it was heaven! Yes it did hurt and I did bleed a bit but the pain lasted just for a minute or two. The next morning I was just a little sore and he made love to me again. wow! After that first time wow! Even now at 52 I still enjoy the memory of a wonderful time.

  10. Comment Import

    From Cat
    My first time was neither a horror story or mind blowingly amazing. To begin with it hurt so much that I couldn’t even get his penis in, after a bit we tried again and it hurt but much less. As I accommodated him he moved in a bit further and further each time until he started thrusting very gently. It only hurt at the deepest part of each thrust, then that pain gave way, not to pleasure but to ‘oh, its not too bad”!I was not with a guy I loved, just one that I liked – to be honest I just wanted to ‘lose it’ before I hit 20, and he was nice, gently and caring.

  11. Rob

    It’s still a little embarrassing when I think about my “first time penis in vagina”. I was 22 and not inexperienced with sex, in fact, quite experienced in everything but intercourse. I was a good looking, intelligent guy who’d had a lot of girlfriends, but was kind of scared off of “going all the way”. (It was the early 80s)😜 and I had been raised in a fairly strict conservatively religious home.

    When my good buddy B figured out that I was a virgin, he went to his girlfriend S and asked her to tell her friend C, who I knew and dated a couple of times, to see if she would have intercourse with me. B and S, and C and I had double dated once, and long story short, the four of us got pretty naked when we parked on “Lovers Lane”. My girlfriend C got a pretty good look at B’s very extra large cock (truthfully, he’s probably 9”- 10” and thick).

    Well, as it turned out, my buddy did alright for himself. The “price” for me to have sex with C that his girlfriend S extracted from him was that he had to have intercourse with C first… and this was with S’s blessing! Turns out that C wanted to try my buddy out after seeing his cock! So he expedited the process the next morning, unbeknownst to me, spent the morning at his apartment having sex with C, and that afternoon I got my booty call. C’s family was home, but we went down to the laundry room. C had her diaphragm in and was ready to go! Remember, at this point I had no idea of the bargain my buddy had made with the two girls.

    C spread her legs and like a good novice, I popped my aching cock in and came with two thrusts. How satisfying (not!) And that was it— we dated one more time and it ended.

    Good news is that eventually I met my wife of several decades now. She taught me everything, and even today “at our age” (mid 50s) we often have long, languorous sex sessions. She taught me how to give her oral (thank goodness for her boyfriends that she practiced with before me!). She comes prolifically and I restrain myself while she rides me until she has to stop. Then it’s my turn, and she can bring me along until I just can’t wait any longer.

    I occasionally think about my old buddy B and my old girlfriend C, and how we all got what we wanted. B had sex with his girlfriend S, and my girlfriend C, and then an hour or so later C and I had sex… a right bargain!

  12. Toby Reeves

    Losing my virginity was an educational film about the consequences of having unprotected sex, of having sex you’re too young, and basically almost all of the “don’t s” I did the first time I had sex. And, the actions of that day wounded me so bad that I’ll never get over them.

    She was 18 and my little brothers babysitter. I was 16, very shy, and a geek as well. She was the aggressive one. I really liked that. And, my nightmare began right after my/our first time.

    When I was about finish I said to her,”I probably shouldn’t cum in you, right?” And, she said,”No. you shouldn’t” So I pinched it! Not a clue as to what happens to you when you do that. So, I pinched, we got dressed, she went back to watching my brother, and I headed off to my friends to boast about my achievement. He lived about 2 blocks away, and half way there I began to hurt down there. the pain grew. When I got to his place I could barely walk. He asked me,”What’s wrong?” And, I had no idea. Of course, once I started telling him about what I had been up to for the last 30 minutes( 3 min. worth of work took 27 more minutes to make me pay of it!). He spat out,” You got Blue Balls!” and immediately started laughing his ass off.

    We stayed together for a couple more weeks, but that was the only time we did “it.” And, we occationally saw each other. We broke up on good terms. I still liked her a lot! But, around 7 months later I heard that she became pregnant and later she gave birth to a healthy girl. I was happy for her!

    Then 2 to 3 months later , as I’m approaching my house, I see a sheriff leaving my house to get into his car. I reach the porch, and see a letter addressed to me from the state. I open it up and start reading. I didn’t notice that the sheriff waited as I read the letter. It was a notice for me to supply a blood sample for a DNA test for paternity. Failure to appear would result in me being declared the father by default. Then I read the day and time for the appointment. It was for that day, and 2 hours ago! I looked up, and yelled to the sheriff,”Hey! I was supposed to have been there 2 hours ago!” And, the sheriff said (with a smile on his face),”You should’ve kept it in your pants, kid!” and he left.

    Instant ulcer! Really! And, from that there were many more problems, emotionally, that arose and would appear every time I liked a girl. Unable to talk to them to this day. Such is my life.


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