Clueless

In my lifetime so far, I have run into a few clueless, oblivious, or just plain stupid people or sexual situations.

I was dating a beautiful woman. I knew it might be pushing beyond her boundaries, but I asked her whether she’d like to go to the nude beach with me. To my delight, she accepted. However, there was one condition: She wanted her two brothers to come along. I figured a chance to see her nude would be worth it, even with those encumbrances.

The weather was perfect. We got to the beach and stripped off all our clothes. I was very happy to see her naked, and have her see me. I guess I’m a bit of both a voyeur and an exhibitionist. I kind of liked the idea of being naked with the guys, too. Her older brother turned out to be a nice and interesting guy. The younger brother was a bit slow in the head. I think maybe he had something like autism, although he was fairly chatty. What was rather amazing about the kid is he sported an erection almost the whole time we were there. Everyone ignored his erection, and a good time was had by all.

For a short time, I dated a woman who turned out to be more of a nymphomaniac than I could handle. For instance, she’d knock on my door at 11pm wanting sex, even though I had told her earlier in the day I needed time to myself. We’d fuck, then she’d wake me up again at 3am wanting more. It was just too much!

One time at a restaurant with this woman, she started trying to unbutton my pants under the table. The tablecloth may have partially obscured the view, but I wasn’t so sure. I pushed her hand away, and a minute later she tried again. I scowled and said I didn’t want that. Still, she continued to try to unbutton me, ostensibly to give me a handjob, like five more times.

I was in the YMCA shower. It was the older style, open shower room. No stalls. It also didn’t have doors. Instead, there was a wall and another wall arranged in such a way that coming from the gym or the pool, you could walk right in, but no one could see inside. It was not soundproof. Just the opposite, as the quietest voices would echo off the tile walls. I was the only one there at the time except for a child about 11 or 12 years old. I could see by the look of his face that he was off in some way. Maybe Mongolism or mental retardation. He just came out and asked, “Does it feel nice when you touch your penis?” I don’t remember what I said if anything, but you can bet I grabbed my towel and got out of there right away.

I found another girlfriend who was more balanced than the nympho. I had a friend who knew my girlfriend was visiting. Her car was in the driveway, and there’s no way he didn’t notice. It was a good neighborhood so I left door unlocked. It was around 10pm. He just came right in as we were both naked on top of the bed. She was on her hands and knees, and I was fucking her from behind hard and long, but making sure not to cum too soon. He sat on the edge of the bed and started a conversation about politics just as if we were clothed and having tea. He didn’t make any move to participate in our activity or anything else. He just kept on talking.

She and I didn’t quite know how to react. My penis started to soften, but to her credit, she wanted to keep going. Soon I was fully erect again as Keith kept talking. She and I had a simultaneous orgasm. I’m sure it helped her that I had a finger in her ass. I think it also was helpful to have him watching. He was looking right at it, yet he didn’t say a thing about what had just happened. He just kept going on about Republicans and Democrats.

When I was working as a general welder, I would sometimes hire a kid to fetch and carry. It was better than arranging clamps to have him just hold things in position while they were being tacked. He was fine kid but his thinking was kind of slow.

One day after work, I invited him to the nude beach. He had not been to a nude beach before, and was excited. I explained that when people get to the end of the trail at the bottom of the cliffs, they take off their clothes and enjoy the sun. This was the more conservative kind of nude beach where nothing of a sexual nature takes place.

As we were walking down the trail, he removed his shirt then his shorts. He was nude half-way down. People just didn’t do that there. I was embarrassed, but didn’t say anything. When we hit the bottom, he spread his towel right away, and started slowly jerking off. His penis was fully erect. I explained to him that it wasn’t proper etiquette. He surely heard my words, but didn’t change what he was doing in the least. I was so embarrassed, I walked away and headed up the beach. In retrospect, that was inappropriate of me, but hey, I was young.

When I returned, he was still masturbating right there in front of everyone. The funny thing is, there were around 6 men and two women standing around him, admiring what he was doing, and holding on a conversation as he continued to wank.

In my late teens, I had a jack-off buddy. This was in a time when masturbation was pretty much never discussed, and considered bad news in much of society. One day, while standing in front of a store with a lot of people standing around, he quietly asked whether I’d like to get off with him later that day. No one could hear him, but as he said it, he made the universal sign of forming his fingers in the shape of holding his penis, and moving his hand back and forth in front of his crotch. I don’t think he was aware of his gesture.

I had a friend who loved everything anal, but he was willing to do the things I liked also, such as practicing multiple dry orgasms, post-orgasm stimulation, and glans blame (rubbing the oiled palm of a hand over the tip of the penis). The poor fellow had no limits. He wanted me to fist him, which I did reluctantly. It should have geeked me out, but actually, I found it quite intriguing to have my hand that deep inside another person. I tried to feel and identify his internal organs. I figured I might be able to feel his kidneys, his bladder, maybe even his stomach. But all I could make out was his backbone.

On another occasion he had a 36″ (92 cm) soft dildo which he had me insert all the way except the last inch. The thing must have gone most of the way to his appendix. He loved butt plugs, enemas, everything to do with his butt. Then one day, I heard he was in the hospital. It seems he had given himself such an enema that he burst his colon and needed surgery.

I had a girlfriend who I asked to tie me down and do whatever she’d like. I had assumed this might be things like testicle massage, tickling, or an edging handjob. First she crawled all over my body and kissed me extensively. I rather enjoyed that. But then, she had this notion that somehow I’d like her to open a little box of cockroaches she had collected, and set them loose all over my body.

I went to a convention. In the hotel on the first evening, I had nothing to do and was thinking about sounding, the act of inserting something in my peehole. Looking around the room, I found a ballpoint pen with a long tapered end. That would make a nice sound, but what to use for lube? The only thing there was a packet of shampoo. OK, I figured, that’ll be sufficiently slippery.

I coated the pen with the shampoo, and stuck it about 4 inches (10 cm) into my dick. It started to sting, so I removed it. It turns out shampoo and urethras don’t get along well together. The sting continued to build and build. It got so bad that the next morning, when I tried to pee, it took twenty minutes, letting out one little, but extremely painful squirt at a time. It took three days before I could walk fully upright again. The pain was just that bad. I told people at the convention I had hurt my back.

Back in the days when one could hook up with people on Craigslist, I encountered a guy who was willing to offer exactly what I wanted at the time. I was really intrigued by glans blame. For those who don’t know, when done right, it really makes a guy squirm. Then after a few minutes, the feeling changes, and a guy might feel like he’s going to pee or cum, simultaneously. In most cases, he doesn’t urinate or ejaculate, but sometimes one does let out some pee involuntarily.

So this guy started rubbing my glans, and although he was a bit too intense for my taste, it was wonderful. Then, while he was still doing that, I ejaculated. But he didn’t stop. It was terrible, excruciating, exciting, actually quite wonderful. I squirmed and tried to get away, but he just kept going. It started to sting. Finally he quit. For the next few days, there was a scab on the end of my cock, because he had worn right through the skin. It healed without a trace within a week.

When I was around 13 years old, I was into photography. This is in the days when serious photographers had a darkroom to develop their own film and make prints. I knew in my adolescent brain, that ‘real’ photographers do nudes. After all, there were always artistic nudes in Popular Photography Magazine. Not knowing any willing girls at the time, and I think not even noticing that the pictures in the magazine were all female, I asked a 13-year-old fiend to pose. He took off his clothes, and I took a bunch of pictures. When my dad came home from work that evening, he saw the negatives hanging up to dry. I got a pretty good lecture about what’s what in the sexual world, including, ‘keep my hands off boys.’ As you can tell, that lesson never completely sank in.

Those are a few of the clueless situations I’ve encountered. Leave a comment below telling us about what clueless sexual things you’ve seen, heard, or done.