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High School Hijinks & Beyond

Posted by: Age: 99 Posted on: 10 comments
3 likes 23 views Category: Sex Stories General Tags: Masturbation, jerk-off, reach around, sucking and fucking, high school, multiple partners
My main squeeze in high school and what we did. 

100% true story.....


As related in an earlier story, I had quite an active sex life while in high school. But about halfway through my Junior year I hooked up with one particular sweetie and we went steady my remaining year and a half and continued as a couple until we married on my 21st birthday. She was 2 years younger than I and a real cutie. She was a petite 5’ 2” with really nice tits. She was a varsity cheerleader by her sophomore year and also made the list of top ten school beauties, also by her sophomore year. It was unusual for a sophomore to achieve those lofty heights.


I really don’t remember exactly how we hooked up but by the second date we were fucking our brains out. She claimed I was the first guy to fuck her which may or may not have been the case. But once we got going, we were at it every chance we could find. Unfortunately at that age, there were limited places we could have sex. Most of the time it was on the bench seat of my ten year old Ford coupe. And it was almost always fully clothed. Back then high school girls always wore skirts so access to her pussy just required pulling her panties to one side. I rarely dropped my pants. Just unzipped my fly and pulled it out. The drawback to this, other than the obvious downside of not being totally naked, was her pussy juices transferred to my cock which ended up leaving faint white stains on the fly of my pants. I spent a lot of time trying to scrub out those stains. Mostly with not a lot of success. Wonder what my mom thought?


My gf babysat for various people, usually on a weekly basis and that gave us an opportunity to shed our clothes and do some serious fucking on a real bed. She also spent a lot of time at my parent’s home and we were able to sneak in a surprising number of hookups. My dad had a pool table in the basement and while mom was cooking dinner we were down at the pool table, but not playing pool.  I would bend her over the table, pull her panties to the side and slide my hard cock in her wet cunt and fuck away. The stairs to the basement were off the kitchen so my mom would be right above us cooking our meal. The whole time I would be pounding her pussy I was listening for the basement door to open. Thankfully it never happened while we were fucking. If mom came down the stairs it would be a challenge to get everything put away in time. 


Sometimes, if I was unusually horny, but the situation was not conducive to a quick fuck, she would take my cock out and masturbate me. These jack-off sessions rarely ended with ejaculation because of the mess. Once in a while if I had an overwhelming desire to cum, she would cover the end of my cock in a washcloth or several tissues and I would cum without any stray jism escaping. 


I used to work on my car out in the family garage and I got a number of stand-up reach around  handjobs from my girlfriend in the garage. Then I could just shoot my load onto the floor. I would reciprocate with some juicy finger fucking. We even did a few stand-up fucks since there was no place to lay down. I usually had her bend over and doggy-fucked her from behind. 


On rare occasions we would be home alone. There was one time when we were going to the movies with another couple. We were at the house alone and weren’t due to be picked up by the other couple for about 30 minutes. I lay on the sofa in the living room and she straddled me and bounced up and down on my erect prick. But the other couple arrived early and came in through the back door. We never heard them until they walked in and caught us fucking. Nothing could be seen because her skirt covered everything. The guy said, “We’ll wait in the car.” Not a word was ever said about it. That was the only time in my life I ever got caught having sex except my second wife caught me jacking off once after we had separated. We were still living in the same house until it sold but in separate bedrooms. She walked in on me one morning with my hard cock in my hand just as the semen started spurting. She was quite embarrassed but I thought it was really funny.


After my GF and I had been together a while I developed a really strong desire to suck on her pussy. But back then oral sex was a taboo subject and I was afraid to even bring it up because I was afraid she would think I was some perverted sex maniac. It was rarely mentioned with other boys my age and if it was, it was always in dismissive terms. I had a summer job on a construction site and a couple of the guys caught a couple in a parked car with the guy eating her pussy. There was a lot of derogatory remarks about “the freak pussy eater.” So that even solidified my thinking that there was something wrong with me for wanting to go down on my girlfriend. 


But on one of her babysitting jobs, I found a copy of the Kinsey Report. The book was quite a shocking publication at the time and had only been out about three years. It surveyed the sexual activities of people and was broken down into three classes of people. Those with grade school educations, those with high school educations, and those with college. As expected, those with college educations were quite a bit more liberal in their sexual activities. I found the section on oral sex and was shocked (and pleased) at the very high percentage of people who performed oral sex on each other. I don’t remember the actual percentages. I showed these statistics to my girl friend and although she had some reservations about it, we gave it a try that very evening. And a whole new way to enjoy each other was born. I lapped her pussy until I had her screaming in ecstasy and she sucked my cock, tentatively at first, but got more into it as the evening progressed. I don’t remember ever cumming in her mouth. That might have been a bit too much for her at the tender age of 15. Actually, even into marriage I don’t remember ever shooting in her mouth. That changed rapidly with subsequent girlfriends and wives. 


Back to the oral sex percentages. I attempted to look them up online but couldn’t find anything from back then. But did find a lot of more recent studies. Interestingly, back prior to 1970, oral sex was considered a much more personal act than vaginal intercourse and was mostly performed by married couples. Unlike today where oral sex is probably one of the first sex acts a new couple performs. After reading some of these studies I came to realize that my gf and I were likely in a very, very small group of high schoolers who were sucking each other’s privates. 


As a child of that early era, oral sex has always seemed to me to be a far more personal act than vaginal sex. As I got older but partnered with younger women, it always surprised me how willing many of them were to suck a cock but were a bit shy about fucking. 


During our time together in high school we broke up for a short period. I don’t remember why. But there was another real cutie tht I had had my eye on for some time and I invited her out. It was to attend a party of high schoolers. We hung out at the party for a while but I got bored and got her to leave. As soon as we got in the car, which was actually parked in the driveway of the house where the party was going on, I was all over her. She was very receptive and after a few minutes of serious spit swapping, I was sitting in the passenger seat and she was straddling me. I had already sucked her titties and finger fucked her until her pussy was nice and wet. I got my cock out and slid it right into her cunt. She started moving up and down on my cock. While this was going on there were a number of people coming and going to the party. If anybody realized what we were doing, which was extremely obvious, I never heard anything back about it. Through a story too complicated to tell here, I had several 8x10’s of her topless and for a 15 year old, she had a really great set of tits. I kept those photos (hidden) for many years and from time to time I would get them out and jack off remembering the wild fuck we had. Unfortunately it was a one and done session as my gf and I made up and got back together. During our high school days, that was the only other girl I fucked. Once we had been married a few years that changed dramatically.  


There was another guy in our school who had the hots for my girlfriend. I kind of suspected that he might have had some history with her before she hooked up with me. He was always giving me dirty looks and one night at a school dance, as my gf and I were leaving, he stepped out from behind a parked car and sucker punched me in the mouth. Splitting my lip and spilling blood all over my coat and tie. Then the chickenshit motherfucker took off running. I never had a chance to confront him again except at school where fighting was seriously punished. He was smaller than me and in a fair fight I think I could have kicked his ass.


Coincidentally, his name came up on the Classmates site recently. I sent him a private message asking him if he was still sucker punching people he didn’t like. Never got an answer. 


After graduation I went to college for a year that was located a half a continent away. And although I never had any proof, I’m pretty sure my gf was fucking him while I was gone. I had a younger sister who told me that the two of them seemed a bit too chummy in school. Once I got back from the year in college we took up right where we left off. I wasn’t away from her for the entire year as I had frequent visits home. One visit was particularly memorable as we hadn’t fucked for a couple of months and were hot to get it going again. We were parked in a deserted area in my car and started fucking. It felt absolutely wonderful. I came pretty quickly but wasn’t remotely satisfied. My cock was still as hard as a bar of steel so I just kept fucking her. And came again. No stopping now. I kept on fucking and literally had five separate orgasms. I know this sounds impossible. I thought so at the time but it happened. I’ve never come close to doing anything like that again. I’ve done it where I had three orgasms once and also did it with two consecutive orgasms a few times. 


If my gf was fucking that other guy during my year in college, I couldn’t be too upset about it because I was keeping plenty busy myself with almost more pussy than I could handle. 


The craziest thing about all this fucking my gf and I did is we never used a condom and birth control didn’t exist back then. Despite shooting gallons of cum up her pussy, nothing happened. We had been steadily fucking for over four years before it caught up to us. Two months before we were scheduled to get married, she turned up pregnant. We had three kids and two abortions before calling it quits after nine years of marriage. 


My first marriage came to a very unlikely ending. One night I was  horny as hell and my wife refused to fuck. She told to go get it somewhere else if I needed it that badly. So I got in my car and left. For whatever reason, since I am not a drinker, I took a couple of heavy shots of booze before leaving. I drove to the nearest pay phone and called my wife’s recently divorced best friend. I zeroed in on her because there had always been a vibe between the two of us any time we were around each other. By now it was about 1 am. I woke her up and asked if I could come talk to her. She didn’t want me to come but I went anyway. She opened her apartment door in a robe and we talked for a bit and I made my move. She was very receptive to some heavy kissing but refused to let me fuck her. After a good hour of heavy making out, she said she had to check on her baby. She was gone longer than I expected but came back wearing a see-through negligee that left nothing to the imagination. She was not only a beauty but had a Playboy centerfold body. She said we could not go in the bedroom because of the baby so we got busy on the floor. We sucked and fucked on and off the entire night and early morning. I got off three or four times. It was some really glorious sex. Finally about 6 am I said I had to go home. She told me in no uncertain terms that while it was some of the best sex she’d ever had, it was a one-time thing. And it never was repeated.


I got home and immediately got in the shower. When I got out my wife asked me why were my knees so red. “Rug burns.” I replied. “You told me to go get get laid somewhere else and so I did. Multiple times.” She went ballistic and that was the end of the marriage. Which was already in its death throes. 


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