Posted on Leave a comment

Gay Man’s First Encounter With A Woman

I made it to 34 years old without ever being sexual with a woman. I’m gay. I knew that from my early teens. I loved seeing workmen in bluejeans. Bearded was better. I like thin, tall guys. I’m a tall, thin guy. I don’t have a regular boyfriend. I just have all kinds of sex with guys when the situations come up. No strings attached.

Women are almost non-existent in my mind. They’re just there, like furniture.

Except one woman. She drives a truck for the same company I do. Every now and then, we have two drivers in one truck, usually when there’s a lot of unloading to do. We had a two-day trip through the mountains, involving twenty stops. They figured two drivers was best, and I got paired with Judy.

She’s of Japanese descent, and I actually noticed her. She is attractive. Even though she is small, she is strong and very good at unloading. I know the hetero guys just lose it in her presence. I think she is tired of their juvenile behavior around her. I think she respects me because I act normal around her. I mean, she is only slightly attractive to me. I’m gay, after all.

So, as evening approached, we pulled into a Motel 6. The company reimburses expenses on the road, but just barely. For instance, they’ll pay for one room for two drivers. I figured Judy and I would split the cost of a second room. But no, we discussed it, and decided we were adult enough to share a room. They always have two beds, so no problem.

So we got in there, Judy turned up the thermostat while I took a shower. Then it was her turn, and to my surprise, she took off all her clothes in front of me before stepping into the bathroom. I was a bit appalled to see how naked she was. Women aren’t as hairy as men, and it looks weird. Her breasts were probably average size, but they sickened me a bit. Her vaginal area was covered in black hair, so I couldn’t see anything clearly. But still, that nicely rounded small butt, and her Asian looks were somehow attractive.

While she was in the shower, I started masturbating under the covers. I guess I was actually thinking about her. Why, I don’t know. I was really starting to get into it, getting near orgasm, when she popped out of the bathroom more suddenly than I had expected. She noticed the movement under the sheets.

“Are you jerking off?”

“Well, yeah.”

“Is it because of me?”

“No…. no! – well, yes, I guess so.”

She smiled, and dropped her towel. She climbed into the bed with me. She put her hands on my shoulders, and then sort of started rubbing my neck. Then she kissed me. I lingered, and stayed with it, but didn’t really care for it. But, I didn’t want to hurt her feelings, so I let her kiss me a bit longer.

My penis stayed hard. She noticed, threw the covers off, and wrapped her fingers around it. That felt nice. She stroked it a bit, and I started to feel a bit orgasmic. She stopped suddenly, and asked whether I had a rubber. I did. I rumpled around in my pants on the floor, found it in my wallet, and opened the packet. She expertly fitted it around my hard penis. She then gently pushed me back against the bed so I was laying face up, and climbed on top. It was obvious that she was going to sit on me, and have me enter her mysterious pussy.

I wilted to about half-erect right away. She tried this way and that to get my penis in her, but it wasn’t happening. The more she tried, the softer I got.

“You’re afraid, aren’t you?” she asked.

“Something like that.”

I didn’t want to tell it was more like a mild revulsion. She then climbed off me, and started giving me a tour of her body. That was interesting. She showed me her large nipples in detail, and said she likes having them sucked. She turned around, spread her ass cheeks and showed me her asshole. I liked that. I could easily have gotten hard again (I think) if she had invited me to put it in her anus. But she didn’t. Instead, she continued the tour, showing me her clit, and pulled open her vagina a bit so I could look deep inside. To me, I have to admit, it looked more like an injury between her legs than something sexually inviting.

Have you ever watched a drunk at a party throw up? You know how it makes you feel nauseous too? That’s what I felt when I saw that, and my penis lost any remaining erection it might have had. With the tour over, she suggested we lay side by side and masturbate ourselves. And that’s what we did.

I enjoyed the adventure, and I enjoyed her company. She laid right next to me, with our shoulders touching, and she rubbed herself to an orgasm within a few minutes. Almost as if I wasn’t there, although she later told me that by me being next to her, it made her very, very horny. While she was doing that, I rubbed my penis, and it eventually became hard, and I finally ejaculated. That was it.

She climbed into the other bed, and after an hour of television, we went to sleep. I like Judy, and we have driven together a couple more times, but a situation in which we need to share a room has not come up again. I don’t know what will happen if it does. I’d kind of like a do-over. I think I could get hard and fuck her. I’d like to try and see what it’s like. My buddies tell me it is like butt-fucking, but looser, and that in some cases, you can feel the girls grip you with their inner muscles when they orgasm. I’d like to at least experience that, but don’t know if I could actually manage to get hard, or not. Maybe, we’d just masturbate side by side again. In retrospect, that was fun.

Leave a Reply

Your email address will not be published. Required fields are marked *