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Karen

Age when it happend: 17
Where it happened: Her bedroom
Langauge: English
Sex: Male
Rating: 9
Category: Straight

I was a senior in high school and had been dating Karen, who was a sophomore, for about 4 or 5 months. Karen was a pretty brunette with a fantastic body. Somewhat dark complected but with geen eyes that seemed to glow from across the room.

It was the first real relationship for either of us, and we were both virgins. We’d worked up to masturbating each other, but things had stalled there. For some reason Karen had the rule that one of us had to have our underwear on at any given time.

At a certain point I’d decided I’d had enough. One afternoon after school we were on her bed, and she was naked. I had my boxer-briefs on, as per the rules. Figuring it would be harder for her to resist if she were face down, I told her I wanted a good look at her ass and asked her to roll over.

Once she did, I rolled over on top of her, pinning her with my weight and keeping her legs apart with mine. I pulled down my underwear enough to free my cock and began to rub the head between her legs, searching for the right angle, as I had no experience. She kept saying “Mark, no, I don’t want to.” I slowly forced my cock inside her anyway. She was incredibly tight, and it was very difficult. She grimaced but didn’t cry out, probably because the only other person in the house was her little brother Jack, 7, in the bedroom across the hall. Eventually I achieved full penetration.

As I started slowly thrusting, she began softly crying. After two or three minutes there was a knock on the door. It was Jack, asking if he could go outside and play. She said yes, but he could hear her crying and asked if she was OK. She told him yes, he left, and I resumed thrusting.

I had been pinning Karen’s upper body with mine, but she hadn’t put up a physical struggle, so I decided to lift up off her a bit so I could look down and see her body. As soon as I got a look at that perfect, tight young ass with its tan lines, and my cock thrusting up between her legs I felt that familiar sensation stirring in my balls. I thrust hard to full depth, causing Karen to cry out, and I shot my load deep within her.

After we got dressed, things were amazingly normal between us. She didn’t seem to blame me for what happened, and we starting having sex regularly. As it turned out, Karen liked to be dominated and I had a good time telling her to strip for me, suck me off and swallow my cum, etc.

We even experimented with anal sex. We never managed full penetration on that, but I got the head inside, which gave me a way to cum inside her bareback once we started using condoms for vaginal sex for fear of pregnancy. I also had her penetrate my ass with one or two fingers while she blew me.

Eventually we were caught doing exactly that when her mother returned home unexpectedly one afternoon and found us in front of the TV in the family room. I’d already cum, and Karen had swallowed, but my pants were still around my ankles and her right middle finger was still inside me when her mom walked in. Her finger came out *fast* and it didn’t feel good!

After that her parents banned her from seeing me. That didn’t stop us, though, and we continued to see each other until I went off to college.

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