Where it happened: her house
Langauge: English
Sex: Male
Rating: 9
Category: Straight
My name is Brett and I am 22 years old. I lost my virginity about 8 years ago, the summer just before I turned 15, with Karen, the girl who lived across the street. She is almost 3 years older than me and a knockout, about 5’4”, beautiful face, light brown hair, great body with nice 34C tits. Karen was very popular and she had been dating Jim, one of the High Schools star athletes for about four months.
Karen’s family moved across the street when I was 7. Since we live in the country and houses are far apart, there were not a lot of kids to play with, so we spent a lot of time together.
One day when I was about 8, we were swimming in her pool and her mom had to run to the store. We had heard some older kid talking about skinny dipping, so we decided to try it. Her mom forgot something and came back and almost caught us so we did not have much time to examine each other. We were scared and did not try it again.
Karen started middle school and we kind of drifted apart, but still talked whenever we saw each other. Karen began to develop and from the time I started puberty Karen was my favorite jerk off fantasy.
One hot July day in 2000, both of our parents had left for the wedding of another neighbor’s daughter. I was out front cutting the grass with my shirt off when I saw Karen walking across the street in her bikini. I walked over to talk to her trying to hide my rod. She asked if I would like to come over and swim when I got done with the grass. I said sure and then she commented about how tall and muscular I had gotten over the winter. I had pretty much finished my growth spurt and was about 5’10, 145 pounds. I am fairly good looking with brown eyes, dark reddish brown hair and a slender, but athletic body. My mind was racing with fantasies, but I never dreamed they would come true. I quickly finished the grass, put on my suit and crossed the street. Karen was lying in the sun. She got me a cold drink and we talked for a while. I asked her if she wanted to swim now and she floored me when she said “You know we never finished that skinny dip”. Karen had her top off before I could say anything exposing the most beautiful tits I had ever seen, actually the only real tits I had ever seen. She said come on don’t be a chicken, so I quickly pulled off my trunks and jumped into the pool to hide my growing cock. She took off her bottoms exposing her nicely trimmed pussy and jumped in also. I could not keep from looking at her beautiful body and I could see she was checking me out also. We swam back and forth for a while, splashing each other. She swam over to me at the shallow end and stood right in front of me. Karen put her arms around my ass, pulled me tight and kissed me. My half hard cock was touching her stomach. She told me that she never saw red pubic hair on a guy before and that I have a real nice cock. My cock at that time was about average in length, a little under 7” hard, but it is real fat and I have rather large balls and a lot of pubic hair. Karen asked me if I was a virgin and I told her the truth. I had only gotten as far as feeling up a girl at a party one time. Karen said she lost her virginity to her first boyfriend when she was 15 but only fucked him a few times before they broke up. She fucked a couple of other guys before Jim. She said she and Jim fucked a lot, but she caught him cheating on her last week and broke up with him. Karen said seeing me naked has made her so horny and asked if I wanted to go to her bedroom and fool around. I could not believe what was happening but mumbled sure. I said I had a condom back home, but she said not to worry, she was on the pill.
We got out of the pool, dried off and she grabbed my hand and led me to her bedroom. I could not feel my feet hit the stairs. She had me lie on my back on the bed and said not to worry, she would teach me what to do. By then my cock was as erect as a flag pole. She flicked her tongue on the tip of my cock. Then she licked my fat shaft while sliding my foreskin up and down. Karen tried to deep throat me, but my thick cock was too big for her to get more than a couple of inches in her mouth. She sucked and licked the underside of my shaft and sucked on my hairy balls. Before long I felt like I would explode. I told her I was cumming. She continued to suck me off as I shot my load in her mouth and she swallowed it all.
Now she said it was my turn to eat her pussy. Karen laid back and spread her legs. I did not know what to do, but she took my fingers and pulled back her pussy lips exposing her clit. She told me to flick my tongue on it and she let me know when I was doing it right. I loved the smell of her young hole. Before long she got real wet and started to moan. She kept yelling “Oh Brett Oh Brett” and moaning louder and louder until she exploded in a huge orgasm drenching my face with her sweet pussy juices.
She grabbed me and put me on my back again saying she needed me inside of her now. She straddled me and positioned my fat cock, which had regained its hardness, at the opening of her pussy. My cock was as long, fat and hard as it had ever been. Slowly my cock head entered her hole. I still remember the look of pleasure on her face as she took the entire length of my shaft. Karen rocked back and forth telling me how good I felt and that I was splitting her apart. Her tight pussy griping my cock was ten times better than any of my jack off fantasies. Since I had just cum, I was able to hold off for at least 20 or 30 minutes before I blew my load in the most intense orgasm of my life. Karen kept moaning, and yelling my name during the fuck session and came right before I did. Later she told me she never had an orgasm fucking before, only during oral sex. We both collapsed on the bed and held and kissed each other for about an hour before getting up and taking a shower. We stayed naked and went downstairs to watch a movie holding each other and making out. Before long we were fucking again, this time on the floor, doggy style, then with me on top. I got my nut two more times that night. I don’t know how many orgasms Karen had, but we were both exhausted. Karen admitted that she wanted to bag a virgin and that she had been planning this for several weeks, even before she broke up with Jim. She wanted to get me before it was too late. I kissed Karen good night and she said I gave her the best fucking she ever had. . I floated back across the street right and got into bed right before my folks got home.
I am pretty smart and a good student. I decided to read everything I could find about pleasing a woman. Since Karen’s and my parents all worked days, we had plenty of opportunity to practice.
Even though she was a senior and I was a freshman, we became boyfriend and girlfriend for a while. A short time after school started, we decided to just be fuck buddies and date people more our own age.
During winter break, Karen called me up and said she had a present for my 15th birthday. She had gone back with Jim by then, but he was out of town. When I got to her house and asked where the present was, she said that since I had given her my virginity she wanted to give me her last virgin hole. I reminded her that we had tried that and my dick was too thick to get in. Karen said that she had been practicing with lube and a dildo and she was determined to give me this. We went up to her room and performed oral on each other to get warmed up. She loved to suck my cock and balls and play with my foreskin. I quickly was hard as a rock and she lubed up my cock. She took some lube and buttered up her sweet little bung hole. Karen got down on all fours and I positioned my cock at the gate. We pushed against each other and Karen let out a large sigh to relax herself. To my surprise her sphincter opened up and the head of my cock slid in. Karen then pushed harder as my fat shaft slowly entered her completely. She was so tight, but it felt so good. As I slid in and out, I reached around on fingered her pussy and clit. Karen moaned “Fuck me, fuck my ass hard”. It did not take long before she came in a tremendous orgasm as I filled her hole with hot milky juice. I told her that was the best birthday present ever and I would have to think of something really good for her birthday.
Having dated a senior raised my social status. Karen was not shy about telling her friends that I was a great fuck. A lot of little sluts wanted to hook up with me just based upon my reputation, but I did not take all of them up on it. If I did fuck them, I always used a condom. From time to time, I would go steady with a girl for a while, but most of those relations did not last long. I needed variety.
Throughout high school and college I have had more than my share of sex. I kept track and have had 46 different sex partners, ranging in age from 14 to 33. Three of them were virgins. I had one threesome, but I did not care for it. I would rather concentrate on pleasing one girl at a time. Luckily I never got anyone pregnant or contracted a STD.
Karen and I still fuck whenever one of us gets the urge and it usually includes anal or anything new we want to try.
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