Some Unusual Experiences

This story is sort of a compendium of various oddball sex experiences I’ve had over the years. All totally true. I may have touched on some of these in previous stories.

When I was first married at a very young age at 21 and my wife was 19, we didn’t know anything. This was many moons ago. We had a very lively sex life although by today’s standards it was pretty boring and nothing special. But we didn’t know any better. Missionary position was basically it as far as intercourse was concerned. Even though I knew nothing about oral sex, I did have a craving to try it but thought it might be perverted. I had had a summer job while still in school, working at a large construction site and some of the workers had caught a couple parked in what they thought was an out of the way place. The guy was going down on the girl and the workers laughed about it and kept calling the guy a sick pervert. So, I was afraid to try it. But one night my girlfriend (this was before we married) was babysitting and I was keeping her company. I found a copy of the Kinsey Report in the home, which was a book on human sexual behavior. It had all kinds of charts showing the various types of sex and the frequencies of performing it. Kinsey had his subjects broken down by the degree of schooling. I don’t remember the exact breakdowns, but it was something like; no schooling, grade school graduate, high school graduate, and college graduate. As might be expected, the more schooling one had, the more adventuresome they were with regard to sexual activities. I was shocked to see at the college graduate level how high the percentage was of people who engaged in oral sex. But people who had no schooling hardly did it at all. Anyway, after reading this, I just had to try it. My girlfriend didn’t want to do it but after showing her the statistics in the Kinsey book, I convinced her it was ok to try it.

Of course, once we did it, we were both hooked. I know this is going to sound strange, but I can’t really remember if she sucked my cock in return. Maybe not at the beginning but I’m pretty sure during the nine years we were married that she did. There was a strange thing we did together, and it happened several times. I would wake up in the middle of the night fucking her. Obviously, I had achieved an erection, gotten between her legs and penetrated her vagina while I was sound asleep. Then I would wake up while pumping away. The first few times that it happened, she didn’t even realize I was asleep when I started fucking her. One odd thing about my early sex life is that other than self-gratification, handjobs were not a part of my married sex life. Or even my sexual experiences with various high school girls prior to getting married. Back then I was solely focused on intercourse and luckily, I was successful more times than not. But looking back, I’m sure I could have settled for a handjob during the times I couldn’t get the girl to fuck. My loss.

By the time I got married a second time, blowjobs and handjobs were all part of the mix. One early experience with my second wife, which actually occurred just before we got married, was a trip to Florida where we were renting a 46-foot Bertram double cabin motor yacht and then taking a two-week trip cruising the Bahamas. Unfortunately, a month or so before the planned trip, my father died from lung cancer. He was a heavy smoker but back then, nobody knew it killed you. Anyway, my mom was super depressed, and my girlfriend and I decided to invite her along on the trip, hoping it would cheer her up. Despite the fact that my girlfriend and I were in a super hot and heavy stage of our romance, we agreed to take mom with us even though we knew it would put a damper on the sex to a certain degree.

At one point on the trip we stopped over at a resort in the Bahamas called the Crown Colony Club. Originally started as a private resort by a group of Greek shipping magnates, including Aristotle Onassis and Stavros Niachros, it had been opened to the public although a reservation was required to stay overnight. I had made a reservation way in advance. On our first day there we had a great lunch at a café right on the beach. After lunch, my girlfriend and I elected to lay on the beach and get some sun. Mom sat on the patio of the café reading a book. We were situated less than 100 feet from where she was sitting on the patio along with another 20 or 30 beachgoers, none of whom were closer to us than maybe 30 or 40 feet. We were feeling particularly frisky that afternoon and after getting in the spoon position, I got my cock out of my swimsuit and she stroked it for me. I got a finger under the corner of her bikini and eventually worked it into her pussy. After some foreplay, I was able to get my hard cock into her wet pussy. No swimwear was removed, and it took quite a period of very small movements and adjustments to eventually make penetration. All that the other people on the beach could see was my back. She was mostly hidden behind me. Once I was in, I began to very slowly slide my cock back and forth, just an inch or two at a time. So slowly that unless somebody was really paying attention, it was not even noticeable. The feeling was exquisite, unlike any other coupling I’d ever had. As my orgasm approached, it took every bit of self-control to keep from ramming my cock to the hilt. When I actually began ejaculating, it was an incredible feeling.

Keep in mind that sex is made up of two distinct aspects; physical and mental. In this particular instance the mental side of it was what made it so good. Doing it on a public beach within sight of my mother and 20 or 30 strangers just elevated the experience way beyond what we could have experienced at home in my bed. In fact, we attempted to duplicate the experience of extreme slow fucking once we got back home and it was impossible. Without the public aspect and the fear of getting caught, it just wasn’t the same. Plus, after trying it for a bit, I couldn’t handle the slow fucking part and just started drilling her in the usual way. (Special note: The Bahamian Island were the Crown Colony Club was located is called Chub Cay. The island has changed ownership many times since I was there, and the club no longer exists. But it is still a favored harbor for big game fisherman.)

After my second marriage ended, I dated a woman for about a year. We really had a great sex relationship and had some great times together. One particular outing was one to remember. She was a line dancing fan and took me to a place where that type of dancing was held each week. We had a difficult time finding a parking spot and ended up a good distance from the venue. At the time I had a 928 Porsche and was quite particular about where I parked it. After an hour or so dancing, she got fairly heavily sexed up. So did I. So, we decided to leave and get some action on. But once we got in the car, we didn’t want to wait. I suggested she could blow me or give me a handjob but she wanted to get fucked. So somehow, we both got in the passenger’s seat of the Porsche, which was quite a feat. I was sitting while she straddled me. She was wearing a skirt and had removed her panties. I somehow got my cock in her and we started fucking. But I had a problem. I had to piss really, really bad. I finally told her that I had to go take a piss or I would never cum. It was actually pretty funny. Somehow, I managed to get out of the car and run back to the venue. By the time I got to the men’s room, my cock was still rock hard. I can’t piss when I’m hard, so it took a while to get the damn thing to go down enough to empty my bladder. Then a run back to the car and we again managed to get into position. Laughing the whole time. Got my prick into her…it was hard in an instant because I was so damn horny…and we achieved a fairly quick orgasm for her, and I was right behind her filling her cunt with a huge load of jism. Of course, we had no cleanup materials so my wet cum covered cock went right back into my pants and I’m sure by the time we got back to her house her panties were filled with cum. It had been many, many years since I had done any fucking in a car, but it was definitely very memorable.

Now, I am going to go back a number of years when I was in college in Michigan. I would have been 19 at the time and I briefly dated a really sweet young high school girl who was 18. We went on a picnic to a local park. I didn’t have a car but had borrowed a friend’s car. We did the picnic thing and then got in the backseat to start making out. It really didn’t take long for things to heat up which really surprised me because I didn’t think this girl would give it up as easily as she did. She just didn’t seem the type. But to my amazement, this girl gushed out pussy juice like no other woman I have ever been with. Thankfully the car had vinyl seats because there was literally a puddle of pussy juice on the seat. I got my hard dick out and started nosing around trying to insert it in her pussy. But she wasn’t giving me any help at all, leaving it totally up to me. I wasn’t that experienced, so it wasn’t easy. Finally, it slid in, but she whispered in my ear, “It’s in the wrong place.” She was so wet and juicy that my cock had slid right up her ass. I pulled out and then found the sweet spot. I was wearing a condom at the time which I normally am not a fan of, but everything was so wet and slippery, plus she was pretty tight, that it ended up being a real enjoyable fuck.

Between my second and third marriages, I was seeing a girl fairly regularly, but on a fuckbuddy relationship. We both knew it wasn’t going to be any big love affair. She was appealing, but not a great beauty, however she had a body to die for. I’m somewhat of a leg man and she really had great legs. She would come to my house for the day and both of us would spend the entire day without any clothes and I really loved to look at her. We would laze around fucking whenever we felt like it. She would blow me or give me handjobs while I would suck her pussy until she screamed in heat. We took a trip down to Los Cabos in Mexico which is at the tip of Baja. We stayed in a 5-star resort that was called The Palmilla at that time. It was later made even swankier and renamed The One & Only Palmilla resort. It’s now a favorite of the Hollywood elite and I probably couldn’t even afford to stay there now since it’s about a thousand bucks a night.

Anyway, we had a room in one of the upscale buildings that had a ground floor patio. One night we were out there sharing a chaise lounge, both dressed only in the fluffy bathrobes provided in the room. While there was a walkway that wound by our patio, it was late at night and nobody was out. We were looking at the stars and listening to the surf crash while I fingered her pussy and she stroked my hard cock. She told me she wanted to fuck me and had me lay back while she removed her robe and straddled me, stark ass naked to anybody who might walk by. I was a bit concerned but she told me to shut up and fuck. So I did. But we had no more than started than I heard voices and told her to cover up. She ignored me and kept on fucking. Since she was on top, she controlled the action. I looked over her shoulder and saw two couples walking our way. I started to say something, but she told me to shut up and let her just keep pounding away. As the people got closer, they realized what was going on and stopped and watched. By that point I really didn’t give a shit. The only part of me they could see was my dick as she stroked up and down on it with her cunt. After pausing for a few seconds, our audience walked away clapping their hands.

On this same trip I had rented a Suzuki Samurai which is like a Jeep. It was an open car and one day were driving between Cabo San Lucas and San Jose Del Cabo. She decided to give me a blow job while we passed several trucks filled in the back with workers who all cheered as we drove by. She was definitely a fun partner. She was open to anything and didn’t really give a fuck what anybody thought.  

OK, my next story is a bit crazy and I probably shouldn’t even tell it. I was living on the east coast but had traveled to L.A. on business. I literally had nothing to do one night and although strip joints had never been my thing, I found myself in one of them. One of the girls was drop dead gorgeous with an unbelievable body. This was back before fake tits were commonplace and hers were perfect and real. After one of her routines she came over to sit with me to work me for drinks. I don’t go for that shit because it’s really pricey and usually wasted money. I normally never pay for sex, but I was super attracted to her and made an offer. And she agreed. I frankly didn’t expect her to go through with it, but I gave her my hotel room number and she said she would come over after she was through for the night. The problem for me was I didn’t have that much cash on me, and this was before ATM’s. I figured I could use my credit card and get the hotel to advance me the cash. Well, they didn’t want to do it. After much wrangling I finally got them to do it by paying the additional percentage it costs them for a credit card transaction. I no more than had the money in hand and damned if she didn’t walk in the lobby. Although she did not look at all like a hooker, the hotel staff immediately knew why I needed the cash and although they didn’t say anything at the time, they were pissed. We went to my room and it was a very enjoyable night. She actually stayed much longer than I expected and damn near wore me out. She even wanted me to fuck her in the ass which really surprised me. The next morning when I checked out, I was informed that I was no longer welcome in that hotel. I didn’t give a shit. There are plenty of nice hotels in L.A. and the night was more than worth it.

A former business partner of mine owned a night club and although night clubs have never been my thing, I stopped in the place to say hi and see how he was doing. He introduced me to a couple of attractive 20-somethings and I hit it off with one of them. After a couple of drinks, I invited her to my place which was about ten minutes away. We left, both knowing full well where things were headed. The only thing that makes this particular session worth talking about was at one point, I was on my back and she was perched on top. She said, "I am going to spread my legs out to each side while riding your dick and it’s going to feel just like a blowjob."  She did, and sure enough it felt really good. In that position, spreading her legs caused her pussy to actually get much tighter than normal, and she had an ok tight pussy to start with. It looked like that position might be a bit uncomfortable for her, but she bounced up and down on my cock until I unloaded several spurts of jism into her.

If you are not clear on exactly what her position was, picture her squatting down with her knees together pointing forward. Then she lowers her pussy onto my upright cock. Then she grabs both knees with her hands and pulls them to the side as far as they will go, almost straight out to each side. It really did feel somewhat like getting my cock sucked. This turned out to be a one-time thing because both of us were in other relationships at the time. My girlfriend was out of town for several days. I don’t know what the situation was with her significant other.