A couple of commenters have asked me to relate this experience. This was just about 20 years ago so one, various things may have changed since then, and two, a few details may have slipped my mind- I am getting old.
But first, my first attempt at sex. When I was 26 or 27 I decided to go to a prostitute to end my virginity. I was living in southern California at the time so I made a trip to Tijuana. With much embarrassment I bought some condoms at the drug and discount store, as they were called then, as if anybody cared I was buying condoms. I parked my car on the American side, walked across, and went downtown. Until recently Tijuana or the equivalent border towns were an excellent value for paid sex, if you lived within driving distance of the border- prostitution is legal and cheap. Today is a different story. I don’t know if Tijuana is as bad as the eastern part of Mexico but anywhere in Mexico is probably bad news. If you want to try this carefully check out the situation before you go.
I found a bar/strip club with a few women hanging around. One was pretty cute but not making eye contact with me. Another was OK looking but I wasn’t that interested in her. Somebody throws a little wad of paper at me. I look and it’s the second woman. She is making a sex motion with her hands, running a finger in and out of a circle made with the thumb and forefinger of her other hand. I look away but she comes up to me. I decide to go for it so we leave the bar, go next door, and I pay something like $10 for the room to a guy at a gate, who lets us in and we go upstairs. She asked for the money then, it was something like $25. I pay her and we take off our clothes. She was an actual woman, closing in on middle age, who looked like she had had a kid. She didn’t look like the women in Playboy, so I was a little disappointed. And I was kind of freaked out by the whole thing anyway. As an older guy who actually has experienced a little of life and sex, I would do her with gusto now. She was very nice.
She starts sucking me but I’m not really getting hard. I tried putting a condom on but again I’m not getting hard. I tried inserting but it wasn’t happening. She asked me if I had ever been with “a girl like me” before, and I told her no, I had never had sex before. We gave up shortly after, put our clothes on and went downstairs. She kissed me on the cheek and we went our separate ways.
So I would not recommend a prostitute for a first time. If you’re nervous and inhibited, you’re not going to have the time to relax.
A couple years later I was feeling very disturbed sexually. I had read about sex surrogacy and thought that might be the answer. I looked in the yellow pages and indeed there was a sex therapist offering surrogate therapy in the area. I called and made an appointment, and I explained my problem was I had never had sex before.
The therapist was a relatively young guy. I talked to him and he explained each session would be two hours. I would talk to him first about what I would be doing, then spend an hour with the surrogate, then talk with him and the surrogate about what we had done. I was required to take and HIV test and bring the results but no condoms were involved.
I came back a few days or a week later and he introduced me to the surrogate, a Filipino woman. The program was a gradual process, starting with just touching with clothes on and only getting to intercourse at the end. I went with the surrogate to the other room. It had a mattress with sheets on the floor. I started crying. She comforted me a little, but then asked me “Are you going to be able to do this?” and I took the hint I needed to stop. The first session was she spent some time just running her fingers over my face, then I did the same to her. The next was touching feet. The next I think we got naked and did backrubs. This was not cheap- I was paying $200 a session, out of my own pocket or credit cards, not covered by insurance- but I was getting comfortable with sex and contact.
We got to the genitals and she showed me the parts and function of the female anatomy. I learned cunnilingus and stimulating the clitoris and G-spot with a finger. I got quite good at it, she had an orgasm and said “I got your face all wet!” I enjoyed it a lot then but haven’t felt the urge to perform orally on a woman for a long time.
They told me I was going to get inside her, but at a time of her choosing. They had something they called a “quick dip”- she gets on top of you, inserts your erect penis into herself to check you can do it and nothing happens, and then quickly gets off. I remember her getting on top of me and her straight, shoulder-length hair brushing against my face. That was erotic. Then she put my penis inside her vagina, and I wasn’t that impressed. “Is that what all the fuss is about?” I asked myself. Remembering it now it was wonderful. It was tight, deliciously warm, and to my surprise rough.
As an aside, that’s why I hate condoms. You feel none of that with a condom, except a little pressure. If there is one reason we have to hate gays, it’s because they got everybody convinced you have to always wear a condom or you’re going to die. Actually, no. Men having anal sex need to use condoms. Otherwise you don’t.
I had full intercourse with her the next time, I think, but couldn’t come. They switched me over to another surrogate for what they called “validation”, or seeing if everything worked with another woman. She was a nice-looking, fair-skinned Latina, and we hit it off great. I ate her out and she loved it, we had intercourse but I couldn’t come. Still that has been one of the best sexual experiences of my life. The next week I came back. I wanted to try it with a condom on. I made some positive mention of the small amount of fat on her body and she pouted. I couldn’t come this time either. She was curt in the debrief, still hurt, and left. I still feel bad about that. One is constantly reminded how sensitive women are.
So I learned how to have sex with a woman and do it pretty well. The problem of not being able to reach orgasm has continued to bother me. The reason I recommend this for guys with no sexual experience is I think if you are trying to get with a woman, the fear of what is going to happen if and when you finally get her naked is always there.