Clueless

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 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 autistic or something. What was rather amazing about the kid is he sported an erection almost the whole time we were there. Everyone ignored his erection, including him, and a good time was had by all.

I had a male 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 and she was giving me a wonderful handjob. 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 softened, but to her credit, she kept going. Soon I was erect again as Keith kept talking. I ejaculated right in front of him. 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 a 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 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.

When I was around 13 years old, I was into photography. This was 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 of 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.