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Jonathan

Age when it happend: 18
Where it happened: Her parent's house
Langauge: English
Sex: Male
Rating: 9
Category: Straight

In the summer between 6th & 7th grade one of my camp bunkmates received a letter every week from his girlfriend back home, which made him a little boastful. I didn’t know any girls at the time, so I was a little bit intimadated by the fact that he was way ahead of me in that department. His hometown was about 300 miles from mine so I thought maybe they grow up faster in those parts.
When I was in 9th grade I noticed one of the 7th graders on my Jr. high school bus was incredibly cute. Everyone knew that it was very tacky for a 9th grade boy to date a 7th grade girl, but I knew that a two year difference became less significant at some point in the future. I thought about that for a minute and expected that down the road, I’d still be at a competitive disadvantage compared with other guys.
Three years later I’m a high school Senior. That girl from bus is a Sophomore with an exotic look (sort of Asian or Hispaic, neither of which is in her background) and small breasts. We know some of the same people and are in some of the same clubs.
We talk occassionally. I notice she talks about herself a lot. Over time I notice she also talks about me. Sometimes she talks about sex in the abstract.
I started to pick up on the clues & tried to figure out how to act on this without risking complete humiliation.
Finally, I simply said to her, “I think you have a crush on me”.
In hindsight I should have made a point of saying that in a private place. She responded, “Yes!” loudly and started arguing that I should stop being so standoffish in front of a handful of people.
So there is was, a beautiful female, that I’d been interested in for three years, offering herself to me. Since she was being confrontational, I couldn’t agree to anything with her without seeming like I was losing some argument.
So for the last few months of my time in high school we still talked occassionally and she would still have ridiculous moments with me where she was publicly very inappropriate.
She got a summer job at a sleepaway camp & we stayed in touch on & off via the mail.
In my Freshman year at college, nearly everyone I met claimed to have had sex & I believe it was true in most cases. Naturally, I was determined to join the club.
My pen pal invited me to her Sweet 16th birthday party on Thanksgiving weekend. When I first got home, while I was riding in a car, she & I saw each other for the first time since June. From a distance, I could tell she had stepped up her cup size in the intervening five months. I went to the party. After everyone left, I stayed & played a little backgammon, which was popular at the time.
After my first semester ended, we got together for a movie & I began a makeout session in the car afterwards. After I unclasped her bra, I asked her if she minded. She said not at all. What a stupid question.
The next night, we had her parents house to ourselves so we had a chance to fool around again.
Two night’s later was New Year’s Eve. She had ideas of a quiet evening alone together, but her dad vetoed that one, so we went to the club which had the smallest cover charge.
She had fake proof, so we got in with no problem. The place was crowded & the band was lousy so we left a few minutes after midnight & headed back to her place.
She told me we’d have the place to ourselves for a while since her parents would be out late. We went to her bedroom. Her blouse & bra came off immediately. Then I unbuckled her jeans & began to pull them off. She wasn’t wearing panties.
Once her pants were on the floor, she gave me a look that was part embarrasment and part excitement. I asked her how she felt and she told it was a nice feeling and now it’s my turn.
My clothes were off in about five seconds. In bed with a naked girl, I had been fantasizing what I would do at this moment. Kiss her here, stroke her there, all very romantic. No time for that, I was determined to lose my virginity before her parents came home.
I started to get us into position. She stopped me & asked if I was expecting we’d be having sex. After I said yes, she wanted to talk about & asked me if I had done it before. I told her no. She was surprised, oblivious to the fact that I had no other prospects. Finally she agreed.
Just about everything the can go wrong in the act did go wrong. We took a break and I gave her a backrub. We resumed the effort but things did not get any better. Must have been nervous as hell about her parents catching us.
I said we should put our pants on that way, we’ll have a less to put on if they did come home early. So we retreated back to second base. By the time her parents did come home, we were safely downstairs in the den and fully dressed.
We stayed together for about a year after that. I’m happy to say, we did get the the hang of it and our sex life became fairly adventurous. Wild sex with a stunning young lady, not a bad way to start out. We were a volatile combination and we eventually had an angry breakup.
That was my introduction to sex. In that department, I’ve had my ups and downs. Have to mention one of the better moments (which I am not making up). When I was around 30, I compared life histories with my girlfriend at the time. Turned out she was the one who wrote those weekly letters to my old bunkmate. Quite a conquest.

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