Where it happened: Back seat of the family car
Langauge: English
Sex: Male
Rating: 10
Category: Straight
It was my senior year in high school. I was 18 and one of the “good looking” guys in my class (although I had been raised strictly as a “good boy”, so I didn’t necessarily have the right upbringing to take pride in my looks and use it in my favor with women.) I was an athlete, big and pretty muscular. Her name was Jenne. She was from another town and was dating a teammate of mine. She was blond, athletic and simply gorgeous to me.
The first time we met, she was visiting her then-boyfriend at our high school. There was a strong attraction between us from the first time we met. (So strong, in fact, that I felt guilty and tried to be extra-platonic with her (if for no other reason, many of my other teammates were hitting on her like crazy and I thought that was a really disrespectful thing to do to their fellow teammate and his girlfriend.))
Maybe a week or so later, she started calling me at home to talk. The attraction was still there, as strong as the first day. After a few calls, she started talking about wanting to go out with me. I was very, very attracted to her, but I told her I wouldn’t do anything with her behind my teammate’s back. A day or so later, she called me up again and said she broke up with him (which pretty much floored me on the spot.) Needless to say, we planned our first date for the next time I was in her town.
The first date went smoothly…just dinner and shopping at the local mall. We ended up kissing heavily in the car at the mall, but nothing further that night. A couple weeks later, the next date was similar (dinner and a movie) and then drove to a quiet spot to “play.” We went much further the second time…long time of kissing and touching. I felt her bum for the first time (she was a sprinter on the track team…incredible ass she had) and even got to rub her pussy from inside her undies. She also took my cock out and played with it, even licking the head a few times. (Before licking it, she said, “I’m not going to do what this looks like, but I want to try this”, which in retrospect makes me smile, thinking how she was embarrassed to be “giving a guy a blowjob.”) It was also on that second session that she told me she wasn’t a virgin…she’d done it twice before. I was a virgin and told her so…I don’t remember much of the conversation other than that, but I do believe it set her mind on being my first.
Our third date wasn’t as much of a date. My older brother and best friend were along with me on a shopping trip. (We lived in a small, rural town that didn’t have any real place to shop.) My girlfriend had to work, but we made plans to get together after she got off work and my brother/friend were at a movie.
Anyway, the time came to go pick her up. We talked about going to the movie, but we decided to just go park. She directed me to this riverside park where we parked and got into the back seat. We made out intensely, with her pussy getting a lot of manual attention, as did my hard cock. Pretty soon, we were both naked and I started eating her pussy (something she’d never had done before.) Unlike her, I had given oral [to a woman] before, so I proceeded to eat her for maybe 5-10 minutes. I’d seen guys rapidly flick a woman’s clit in pornos, so I lifted my tongue off (when my jaw started to ache) and flicked her clit rapidly with the side of my index finger. My girlfriend started moaning loudly and moving around and, before I realized what was happening, she tensed up and grunted loudly. I felt a warm, thick liquid spray out of her and onto my chin and lips. She squirted a couple of times then stopped, but continued to tense and grunt for a few moments longer. (I knew it wasn’t pee…didn’t smell or feel like it…it was only later on that I learned that she had “squirted.”)
After she relaxed, I got out a condom and rolled it onto my stiff dick. She smiled at me and spread her legs further…welcoming me to go all the way. I fumbled for a few seconds, trying to find her opening in the dark…but then the magic happened. The head found her opening and slid into her very tight, hot pussy. I slowly pushed into her and once I was all the way in, she pulled me to her and started kissing my very passionately. I wanted to be a good lover, so I was trying to hold off (she was incredibly beautiful and very tight…but it felt soooo good to be inside her like that.) I pushed in and out of her for close to 10 minutes before I couldn’t hold off any longer. (She told me later that she had another, smaller orgasm during that time.) I was afraid that the rubber might have broken without me knowing it, so when I started to cum, I pulled out of her while I shot the load of a lifetime into that unbroken condom. My goodness, that was a wonderful time!
After we both relaxed, we figured we better get back to the movie theater. I still remember her smile and look while she dressed. I had the dome light on while we cleaned up, so I could see her lovely, small breasts…her flat stomach…her toned legs…and her lovely, chestnut-colored bush. Had I known at the time that she was probably the mostly lovely creature I’d ever know intimately…hell, I think I might have known that even then. I loved her as much as a man/boy my age could at that time.
I dropped her off at her house (as I was late for picking up my brother/friend at the movies). When I got to the theater again, my brother and friend were majorly pissed. It turns out that they had issues with the film and weren’t able to show the movie. So they were stranded at the mall for 2 hours. I got to hear them bitch me out the entire way home (75 minute drive), but I really didn’t care. I had just lost my virginity to the most beautiful woman in the world and could care less about them having to hang out at the mall for 2 hours.
The ending of this story isn’t as happy as I’d like, but here it is. Jenne’s mom was a psycho man-hater (she was a divorcee and a raising two kids on her own.) She was deeply involved in church and she loved Jenne’s ex (who was the son of a preacher.) Her mom started reading our letters (this was back in 1990…no e-mails or cell phones) and found out that we had been intimate. She put a stop to the relationship immediately. I saw Jenne one more time (under strict supervision of her mother), but we never had a chance to build on the love that might have been. We don’t get the chance in life to go back, but I still wonder to this day (even as a married, father of 2 with a successful career) what might have happened if I’d had more time with Jenne. (I even tried calling her a couple of years later, but got her mom on the phone and she wouldn’t let me talk to her.) I still carry that love with me to this day.
Jenne, if you ever read this (and are still talking to me after posting our story), you can find me on classmates dot com. I’d love to talk to you again…to see if life has been good to you and hopefully be friends.
Thanks for listening!
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