Risky Sex

We’ve all done it. We’ve all had sex at risky places or times. But there is something about taking a risk that makes the sex even more exciting. I’ve been around long enough that I have had a number of situations that in some cases, bordered on crazy. And looking back, I wonder how I got some of those women to go along with it.

And it’s interesting that the very first time I attempted to have sex with a girl it was very risky. I worked part-time in a gas station, and this girl used to stop by in the evening to buy candy. Without so much as a conversation, I led her into the lady’s room and tried to fuck her. She didn’t resist but I never made penetration. The excitement was too much and I shot a load of semen all over her pubic area. The following evening we had a proper fuck in the front seat of my car,

About a week later, I picked up a gal who was hitchhiking and immediately sensed that pussy was there for the taking. I drove to a local park. We walked back into a wooded area and went at it on the ground but in plain sight of any other visitors. This was only my second time fucking a girl.

I hooked up with a regular girlfriend while still in high school. She spent a lot of time with me at my parent’s house. The house had a basement with stairs from the kitchen. There was a pool table in the basement and we used to go down there almost every evening while mom was fixing dinner in the kitchen above. Supposedly to play pool. I would pull her panties down and bend her over the pool table and fuck her doggy style. Either of my parents or my sister could have come down at any time and caught us.

I broke my kneecap in an auto accident and had a hip-to-toe cast on my right leg. My GF and I were at my parent’s home alone, waiting for another couple to pick us up to go to the movies. We had time to kill so I lay down on the sofa with my pants unzipped and my dick out. My GF straddled me and pulled her panties to one side and slid onto my cock. She was bouncing up and down on my dick when the other couple walked into the room. They were early and had walked in the unlocked back door. Nothing could be seen because my GF’s skirt covered everything. The guy said they would wait in the car and they left. We couldn’t finish because my dick instantly went limp. That’s the only time I was ever caught.

My GF and I broke up for a period and I took another high schooler to a party. We got bored and we went out and sat in my car in the driveway making out. I proceeded to fuck her while several of my schoolmates walked right by my car.

Back with my GF we used to neck like crazy in movie theaters. I never fucked her in a theater but I did get several hand jobs. We eventually married but it didn’t last.

During all my years of dating her before we were married, we used to fuck five or six times every week. But during all of that time, we were never able to be fully naked while fucking. So it was always just me unzipping and getting my cock and balls out and her pulling her panties to the side. Since the majority of our fucking was in risky situations we always wanted to be able to get our clothes back to normal as quickly as possible.

While in college in Michigan I was taking an overnight train ride home and was fortunate to sit next to a really cute high school girl. After everybody was asleep. She climbed on top of me and we fucked. It was very risky because the conductor frequently walked up and down the train cars.

My wife and I attended a Halloween party. We knew the hosts but nobody else. I hooked up with a very attractive gal in a catsuit and pulled her into a hall coat closet and fucked her standing up. It was awkward and difficult but fun. I never knew her name.

At another party at our house I was attracted to the wife of a friend of mine and we somehow snuck out the back of the house to a wooded area and did the deed on a bed of pine needles. Luckily nobody missed us.

I took a woman on our first date to a Trader Vic’s restaurant. We proceeded to get shitfaced on rum drinks. She got my cock out under the table and I finger fucked her pussy. While our actual activities were shielded by the table cloth, it was very obvious what we were doing. We finished things off royally at her apartment.

I was on the beach at the Crown Colony Club in the Bahamas with a girlfriend who later became my second wife. We were horny as hell. Surrounded by other beachgoers, I managed to somehow get my cock in her. I had gotten my dick out of a pants leg of my swim trunks and pulled her bikini bottoms to one side. Once inside her I proceeded to slow fuck her with barely perceptible movement. Agonizingly slow because there were other people within 30 or 40 feet from us. When I finally orgasmed it took every bit of willpower I had to keep from ramming it home but I somehow kept that slow pace. It was one of the best orgasms I ever had as stream after stream of semen shot from my dick into her pussy. This was probably the riskiest fuck of my life. And one of the best.

I ran a rather large company and had a girl working for me that for some reason drove me crazy wanting to fuck her. One day she was in my office and despite the fact that nothing had ever gone on between us, I couldn’t help myself and I kissed her. She surprised me by being extremely receptive. We kissed several times and I did something that could have cost me my job. I pulled her skirt hem up and tucked it in a belt she was wearing. I dropped to my knees and pulled her panties down and buried my face in that sweet pussy.

I stood up and led her into a private bathroom off my office. I bent her over the sink and buried my rock-hard cock to the hilt in her sweet-tasting pussy. She said she was on the pill so I unloaded spurt after spurt of cream into her.

A couple of days later, I took her to lunch at a local restaurant, and after we ate, I fucked her in the car in the parking lot with many restaurant patrons walking by. We had some crazy chemistry that I’ve only had with one other woman.

As part of a new position I assigned to her, I drove her around to several suppliers she would be working with to introduce her. After the introductions, I would fuck her in the parking lot. She wanted to resist me because she had a serious issue with me being married. But the chemistry was so strong between us that it was impossible for either of us to resist.

Between marriages, I dated a woman, and we went to a luxury resort called the Palmilla in Los Cabos, Mexico. On the lightly attended beach, we found a somewhat secluded spot behind some rocks, and I ended up fucking her. Mostly at her insistence because I was very concerned that we would be seen.

I also fucked her in the front seat of my Porsche (a real challenge in itself) at a country club parking lot. Again, with other people in view.

I met a flight attendant on a cross-country flight. On a later flight, she had a stopover in my town. We went out to several nightclubs and ended up spending the entire evening partying. Much to my disappointment, because I had planned to take her to my apartment for sex. Finally, when the last club closed at 2 AM, we went to my car in the club parking lot, where I expected to drive her back to her hotel and drop her off. Instead, as soon as we got in the car, she got my cock out and gave me a great blow job. Again with club patrons streaming by my car while I pumped my entire load down her throat.

I took a couple of buddies to the 2 O’Clock Club in Baltimore where a stripper jacked me off under the table with both my friends sitting with me. It seemed risky at the time but was probably a common practice.

That’s some of my risky hookups. Tell us about yours.

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