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Losing Your Virginity

Fiction Versus 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

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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 mindblowing 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.

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". 

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.

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.

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