Since my divorce, I have dated a number of women. For the most part, my dates, with few exceptions, have been women who were divorced after being married for a substantial amount of time. Most were married at a fairly young age; right out of college or soon thereafter. In other words, they spent the majority of their sexual lives with one man, with whom their relations had been strained for a number of years. It is logical to assume that their love lives suffered as well. Chances are, then, that they didn’t have much sex toward the end of their marriages.
So, it’s not surprising that once they are back in the dating pool, they are anxious to meet someone who can provide them with the things they were lacking in their marriages, both physically and emotionally. I don’t want to paint an incorrect picture of these women’s priorities. They really do want to find a man who they like and respect, who respects them and makes them laugh, and who could possibly become a long-term love interest. They aren’t kidding when they say they value honesty and integrity. Uniformly, they want someone who will really listen to them. They seek kindness and consideration. Little things actually mean a lot.
If I am honest with myself, I am not too different from these women. What I want is more a matter of degree than of kind. In other words, perhaps I am more willing to compromise on the woman’s commitment to having a relationship with me in favor of sex. Still, I would like to have a long-term relationship some day. I suppose like everyone else, it will happen when I meet the right person.
Finding the right woman, however, is a challenge. As expected, on a first date, everyone puts their best foot forward and endeavors to make a good impression. When I go out, I try to have a good time and usually do. That often leads to a second date and beyond. If things go very well, we might even wind up in bed.
I am 49 years old at the time I am writing this. That puts me into a certain demographic when it comes to eligible women to date. And despite how many times you have heard that men only like young girls, I am happy in my chosen demographic – 18-24. Just kidding. Since my divorce, I think the youngest woman I have dated was seven years my junior. I would be happy to share the age of the oldest woman I dated, but she refused to tell me. She claimed to be 52. Right!
There was another clear sign that this relationship was not going to work. One night, I brought this woman to Pinto and Hobbs, my favorite karaoke bar. I love it there because it has a very mixed and relaxed crowd of people who love to hang out, drink, chat and sing karaoke. My date, on the other hand, who must not get out that much, was horrified by some of the patrons. I guess she wasn't accustomed to seeing tattooed youths, blacks and homosexuals, all in the same room with white people. Apparently, she was not a bar person at all, and felt more comfortable in the dinner/theater world. Sensing her discomfort, I brought her to my house, had sex with her, said goodbye when she left (she had to be home by midnight or so - work the next day) and then tended to my sore dick. During sex, however, and knowing she had to leave, I could think of only one thing - getting back to Pinto and Hobbs to sing another song. And return to karaoke I did. I sang Delilah by Tom Jones, but changed the lyrics a bit. Instead of "why, why, why, Delilah," I sang "dry, dry, dry, vagina.
I don’t know if it was a post-menopausal issue or what, but to be frank, I decided that there was no way was I going to risk having my dick fall off. Call me chicken for not being able to explain the issue to her. I don’t care. My dick comes first. So, I broke off the relationship before my dick broke forever.
The “52” year old had a problem, but at least she could orgasm without too much hassle. I dated another woman who actually did come with a warning-her own. Before we had sex, she told me that it took her an inordinate amount of time to achieve orgasm and I shouldn’t worry about it if she didn’t climax. Content with my sexual prowess, I was confident that I could satisfy her. Well, my dear readers, it took her forever, as in “forever and a day.” At some point, as I was still making love to her, she began to masturbate, explaining to me that it was the only way she might be able to climax. Fine, I thought, I’ll just keep doing what I am doing. After what seemed to be about three hours (and I am still going strong, mind you), she finally managed an orgasm. Hallelujah! It did make sex seem a tad strained, to say the least. For that whole time I was inside her, she was working on her orgasm. I kept going, but I felt more like a dildo than a person. Or a dodo, I’m not sure. Apparently, she developed this problem during the sexless years of her marriage. Poor girl. Sexual issues aside, however, she was a very nice woman and I wanted to see her again. And I did. But I came prepared. I brought a copy of Tolstoy’s “War and Peace” to read in bed while we were having sex. I had always wanted to read it, but never found the time. She was a little put off when I first started reading during sex, but a lot of life is about compromise and accommodation. And as long as I was able to keep going, which isn’t always easy while reading a Russian novel, she was happy. Still, it was kind of a pain finding a comfortable position to read and turn pages, so the following time, I popped in a long movie – “Lawrence of Arabia,” one of my favorites. Unfortunately, that made me think about the dry as a desert woman and ruined the sex and the movie for me. I don’t know if I’ll ever be able to watch Peter O’Toole again without think about my “tool.”
Of course, there have been less dramatic encounters since I started dating. There was the woman who drove in from Massachusetts. Relatively good-looking, nice figure, but absolutely horrible teeth. Dreadful, in fact! Brown and rotting. No wonder she didn’t have a big toothy smile in her picture online. Could this be what the Mona Lisa was hiding? Bad teeth? In all likelihood, yes. The whole time I was wondering why my date never had them fixed. She seemed to make enough money to have done something. I had only one word for her. Veneers!
Some dates have taken me by surprise. Last year, I was scheduled to appear on the Coop and Tobin morning show (WPDH in Poughkeepsie) to promote my book and have a general good time, which I do whenever I am on the radio. This woman I had been seeing for a short while lived nearby within the station's coverage area. Of course, I told her I would be on the show so she could listen, and made plans to visit her afterwards. When I am on the radio, I am often confronted by angry callers who think I am despicable for having written a book about how to get away with cheating. To be honest, I think of my book as tongue-in-cheek to a great extent, even though it is based on many true observations about the human condition. Many people, however, take it seriously, and as Sid Stein, I defend my book. In the course of defending my book, things sometimes start to get a little out of hand and over the top. Conversations often devolve into arguments which at least makes for entertaining radio. As things were heating up on WPDH, a woman called in and began arguing with me. We really knocked heads over the airwaves. She was one of those adultery survivors who get holier than holy about fidelity. It was pretty funny until I later discovered that the caller was the woman I was seeing after the show. Despite the fun romp we had at her house, I didn't hear from her after that. I hope it had nothing to do with the handcuffs.
If you have been reading my blog, then you know I could easily wax on and on. Some women I have dated who should have come with warning labels I have already written about. There’s the one with the violent ex-husband. There was one who would have six orgasms during the first minute of sex and then fall asleep satisfied. One turned out to be racist. She was from South Carolina. I should have known better. You've already read about the one with the fiancé in "Sid Stein vs. the State Police. There was one who called a condom “your little friend.” Sheesh! There are those with just so much baggage they shouldn’t be dating in the first place. And if you aren’t completely satisfied with this entry, don’t worry, some women warrant their own stories and those are in the pipeline.
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