Losing Your Virginity

Fiction Versus Reality

I was reading a few romance books to take my mind to another place. One thing I noticed was that when these women lost their virginity, the pain only seems to surface for a second before the feeling turns into earth shattering pleasure. However, when I read other types of literature, I learn that this not true. The 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 to the the woman when it is her first time? Did the pain turn to pleasure quickly? 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 Faenia
My first time hurt so much that my boyfriend had to stop halfway through because I honestly couldn't bear the pain. The second and third times were also quite painful. It wasn't until halfway through the third time that the pain subsided, and it wasn't until the fifth time that I began to see what all the fuss was about. Prior to my fifth time, I had sex out of a sense of obligation and curiosity; afterwards, I did it because I enjoyed it. I envy girls who have an easy first time. I really do.

From Sam
I was seventeen at the time and the girl who gave me this experience was nineteen. I meet her through my older brother and we started to hang out some. She had her own apartment with a roommate so it made it nice to go over and just hang out or head off to a movie. She had a boyfriend at the time but didn't seem too serious. One night I went over and she was all bummed out since they had broken up she got a little cuddly with me which felt nice. I hadn't been with very many girls and had only kissed a few. One night we were watching tv on her couch and we started to make out. This was the beginning of my sexual learning curve that took off from here.

It wasn't long after this that she moved just right so my hand was on her tit. Once it was there, I took full advantage of it and enjoyed my first tit. She then laid on me one night and I had a nice hard cock which I knew she could feel and I wasn't shy about giving her full access to it as she laid on me. She started to dry hump me and I ended up shooting a stream of cum in my pants that night. So we would hump each other and I would let my hands wander under her blouse and down her pants. I could hardly wait to go back again.

Then one night we were in the middle of a nice session and she unzipped my pants and pulled my cock out from my shorts. I just laid there as she gave me my first hand job and I sent streams of cum all over me. She had a wicked but erotic smile. After a few more hand jobs, I finally returned the sexual favor and had her pants off and gave her a nice fingering. I wasn't sure what I was doing, but she sure seemed to enjoy it.

Then the special night happened. We got going making out, with some dry humping, removing each others clothes, and I was fingering her and she was stroking my cock. She pushed me onto my back and straddled me, then took my cock and slid her pussy down on it. I watched as it parted the labia lips through her bush, and disappeared partially in her. She started to move her hips and I could feel her pussy moving against my cock. I started to pump also and it felt so good to be moving deeper into her. I only lasted a minute and then I felt my cum squirting out filling her pussy. She milked me dry and I was now no longer a virgin. She taught me so much about fucking before we moved on.

From Tim
I was 22 at the time and she was 21. We had been dating for awhile and were engaged when it happened.  Things started to progress rapidly at one point and it started with some dry humping. I was nice and hard and she had her pubic area pressed right on my hardness. A slight movement started and it wasn't long before we were grinding hard against each other and thoroughly enjoying it. This opened the flood gates for us and it wasn't long before I was feeling her tits, rubbing her ass, and continuing the humping. Access to below the pants was our next step. I was the first to explore this area by sliding my hand down her pants to her ass then to her pussy. Absolute heaven for me and she couldn't get enough of being fingered. She also started to go for my cock and I unbutton my pants. We kind of took turns removing each others pants so it never went any further than some fingering and hand jobs. But she was the first woman to give me a hand job.

It finally happened one afternoon. We had started to enjoy each other and I had her naked except for her panties and I only had my shirt off. She then slid my pants off and pulled my shorts off releasing my swollen cock. She was stroking it and I had my hand down her panties fingering her wet pussy. I then removed her panties and enjoyed the nice view of her nakedness in the afternoon light. She straddled me and took my cock up to her pussy letting it slide through her bush of pubic hair. She moved it down to her labia and was stroking her labia with my cock. I was covered with my lubricant and she was wet as could be. When she put the head of my cock in her labia, it slid in and there was no stopping us. I pushed a little and it went in further, she then followed and little by little it went in. Our previous humping experience kicked in and we were pumping my cock in her pussy. She was tight, but we had taken it so slow at first, so she didn't have a lot of pain. But she wanted my cock in her and I wanted in there too. We weren't backing down now. It was a nice short fuck and I could feel me ready to cum. We were smart enough to pull out, even though it was so hard to do so. I started to shoot cum all over me not long after pulling out. The next time we fucked, I had a condom on and we went all the way.

From Greg
I had been seeing this girl for awhile and we had fun fooling around. Lots of making out and she didn't mind me feeling her tits at all. She had marvelous tits, some of the biggest I have ever played with even to this day. She was also the first girl that let me finger her pussy. One night we were messing around at her house in her bedroom and I had her shirt and bra off enjoying her tits. She pulled my shirt off and the skin on skin contact was great. I moved onto her pants and this time she let me pull them off instead of just playing under them. She then took mine off and pulled of my boxers.

This was the first time I had been nude with her. I felt my cock against her nice panties and we started to hump each other for awhile. Then I moved my hand under her panties to feel how damp she was. I pulled off her panties had a nice fingering session. Then I was laying on her feeling my cock against her nice bush. We continued to hump for awhile like that it was feeling really good. It then felt slightly different but better and I wasn't sure why, but couldn't stop humping. My cock had actually slide inside her and I was now fucking her enjoying her vagina wrapped around my cock. I finally felt that great feeling and released my first squirt of cum. I kept on pumping with each pulse and had my first orgasm from fucking. I wasn't sure what had happened until after and thought about it. I realised I had actual had my cock in her pussy and it was my first fuck ever.

From Sarah D
I was 17 and the youngest of four daughters, the only one still living at home. I don't think I am particularly good looking and this makes me shy. I can never think what to say to people. I was going out with a physics student at the nearby university who I met at a youth group he was helping at, but after a year we had only snogged and groped a bit. He was a bit geeky but was nice to me and my parents and I loved him because although he had had sex with a previous girlfriend he didn't put pressure on me. I went to stay with my older sister who has a boyfriend who stays over a lot. I was waiting to go off to college and my sister said I'd fit in better if I did the deed beforehand. She gave me a box of the pill and told me to talk to my boyfriend.

Turns out my boyfriend liked the idea, and one Saturday I went back to his room- my parents liked me home at night. He drew the curtains and undressed me in the gloom. A man taking off my knickers for sex - very grown up. Then onto the bed - starkers - and his hands were all over me. I was shy but turned on by his passion, then he's moving over me, between my legs, I never realised how far you had to spread them, and then he was in. It was a bit sore but nice to feel him moving inside me. He said it was fantastic - he'd never been bare before - and got into a nice slow rhythm. He must have lasted about five minutes before he goes frantic, and I feel his penis jumping and throbbing up inside me. He had a fantastic climax, thrashing with repeated aftershocks, and there was loads of his thick juice in me. I didn't come but after we napped I showered and went home with sperm in my womb and texted my sister, "job done". 

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.

From Rachel
I was 16.  I dated a few guys beforehand but never had the courage to follow through.  I waited until I was drunk one night and pursued the only descent looking single male at the party.  It was awful.  We ended up making out and feeling each other up on a hood of a car.  He took me inside and we had the option of sleeping on the futon, which we took and my best friend was on the couch,  just a few feet away across the living room of the house. 

I was on top of him and told him it was my first time.  He just stripped us under the blanket we had and entered me.  I had no clue what I was doing, plus I knew my friend could hear everything.  I could feel wetness down there but had no clue at the time what it really was.  All I remember was him pushing me off of him and leaving,  me bleeding like a bloody rat,  my friend asking  "are you okay?" and a guy (turned out to be the man of the house) throwing rocks at the house we were at because he was mad because the lady of the house just slept with my cousin.  Which by the way my cousin caught herpes from her! 

From Jerry
I lost my virginity at 15 years old by my mom's friend who used to stay with us at times. My mother was divorced like this woman. My mother seemed like she suspected that we had did something but she never said anything to me about it.

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.

From Shaikh
Well I was in my 7th grade at that time, and had never had a sexual experience before. There use to be a maid working in our house and one day I was sneaking up on her when I saw her stealing some money from my mom's draw. I shouted at her, she told me she has done nothing, I told her that I know you put the money in your bra, but she said no and then all of a sudden she asked me to check her myself and then I put my hands in her bra, and did not find anything.

Then she took of her bra, and asked me to check her panties which I did, but by that time I was rock hard and started sucking her breasts, then every thing is history, as then she became my sex teacher. By the way, after that I use to steal the money myself and give it to her.

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. This experience is alien to me. 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.

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