The Ex-prostitute

Today’s entry is about one of the more memorable women that I dated waaaaaaaaaaay back in the 90’s. This took place in 1990 to be exact. After reading this one you’ll think I should have called my book Can’t Get Laid. Enjoy!

When I was 18 I had this whole semi-long hair, long bangs, dark jeans and rock band t-shirts phase I was going through. When you’re shy you need a plan to attract women. Yes, I was good looking but in order for me to get dates I needed something to break the ice, something that would make me stand out and help the women come to me. So yeah, the long haired rocker look got me attention from all kinds of young ladies which sounds like a good thing until you realize it was all kinds of young ladies. One of them was a former prostitute. I think she was only 20 when we met. Not a career with longevity I guess.

I worked at the local mall about four miles from where I lived. I only worked at the fish and chips for six months but it seemed like I met my fair share of young ladies during that time. Deni was about average height with short hair and this whole punk rock girl thing going for her. At that time I liked girls who really stood out and she certainly did. She was what you would call chunky and pretty but not downright gorgeous. Just to give you an idea let’s call her a 7 on a scale of 1-10 since I don’t have a picture of her for you to look at.

One of my shifts I noticed her with a couple of friends and checked her out. She caught me noticing her and we had a brief exchange. She came back a few days later and ordered from me and gave me her phone number. I knew right away I liked her. For me it was always like that. This is why I can never understand when a woman would say she didn’t know if she was romantically interested in me or not because I always knew right away if there was an interest or not. I would know within 5 minutes, they either have that spark or they don’t. It’s not just about being pretty they also have to capture my imagination. They had to have some sort of edge, something which makes them stand out. And I have to feel like the conversation with them is easy. And after my high school years if they were too conservative looking that just didn’t do it for me. I need to feel like I could cut loose a little and say a few swear words or crack a dirty joke. I went to a private school so in my experience a lot of young ladies were way too conservative for me, too easily offended.

Deni and I had a very memorable first date. I mean really the more I think about it I remember a lot, especially considering she didn’t turn out to be a great love of my life, not even a girlfriend. Nonetheless, she was very important. We ended up meeting at a park about forty-five minutes from my house, I walked to meet her, as I typically did back in those days. I had a lot of time on my hands. We hung out at the park. I remember crossing the street with her as we left and she put on this pink wig. I cracked a joke about how somebody might see me and comment that they saw me with two different girls that day. She said she could easily see that because I was very pretty. It was a great compliment and very memorable because I wasn’t often called pretty. We ended up going to a great burger place about twenty minutes away. It’s not the burgers that make it memorable it’s the conversation we had afterwards that was.

She ended up telling me about her history in that town we were in. We were in Newark which is a neighboring city and a random guy approached her and said “Don’t I know you?” she said no. After that she told me how she used to be a prostitute. Not your typical first date kind of conversation but she was like that.  She also told me that the most people she had slept with in one night was 8. The phrase TMI was not invented yet. Then as we were walking some more she told me “If you want sex, and I think you do, it will happen.” When I remember this I often wonder what the response of a typical guy would be. What does one say when they hear that? I imagine in her experience that is all she needed to say to a guy in order for that to happen. Being pretty and a woman she probably figured it was that easy. Having slept with eight people in one night I can only assume this was a successful approach for her.

The thing about me is that I have a way of not making things easy for women.  Or for that matter, myself. First off in this instance I was actually offended. Not offended by the idea of first date sex but offended that she would make an assumption about me that I wanted sex. I was always taught that I couldn’t speak to a woman that way. If the roles were reversed and I were walking along the street on a first date and we haven’t even so much as kissed yet it would be considered crass for me to say something like that. I was taught that would be offensive. So for her to make that assumption about me was just downright wrong. Hey if a woman wants to be forward and make a first move like a guy typically might that is fine but there has to be a single standard as far as decency goes. If I can’t say it to you then you can’t say it to me. Second of all what bothered me is that she didn’t even bother to ask me if I wanted sex. She just said I think you want it but didn’t bother to find out if she was right. This defies all logic to me. Why would you not ask? If you’re going to be that bold and make that declaration what is preventing you from the next step which would be confirmation?

So me being me, I just kept my mouth shut. I had this whole thing about if you want to know you need to ask. The real reason being that there were so many times in my life where I suffered because I was cautious and overprotective of my feelings so I never asked thet questions I should have. I would not ask women out unless I was sure of the outcome. I would not disclose an interest without feeling secure. All of this caused a lot of hurt which results in a lot of anger. And she never asked. To be more truthful I should also let you know that I hadn’t decided if I wanted to sleep with her yet. Back then I wouldn’t know until after I had kissed a woman. If I kiss a woman and she is not a good kisser it ends right there for me. We did end up kissing a little and we ended up going to an AA meeting as she was a member. That was my first AA meeting. I remember exactly where it was. Right next to the porno store. And yes we went in there too. Her idea of course. Quite an adventurous first date I would say. We hung out so long we went to eat again and this time at the Bakers square in Newark. It serves your basic American fare. Meatloaf and gravy, fries and burgers, that sort of thing.

We ended up hanging out all day and at around 11 pm we went to her place. I really like this girl. She was definitely different and the conversation was anything but normal. We ended up watching old Mash episodes together and then went upstairs and sat next to each other on a couch. We kissed some and even though I got the green light for sex earlier in the day I was still very shy. I can’t just jump right to it. So I kissed her but I was very respectful about doing anything else. I am not a magician so there was no “David Coppafeel” or anything like that. I was looking for her to lead me in that direction and it didn’t happen.  And frankly the kissing didn’t turn me on. I mean I gave it a good try but I just didn’t get turned on so I had no desire to further things along. After a little while I just knew things weren’t going to go anywhere and it was getting late so I just told her I had to go and I walked home. Maybe the eight guys in one night thing kept me from getting too excited about her. 

Anyhow I saw Deni a couple of times after that but things never really went anywhere. One time I told her I had something I really wanted to tell her and she met me and told me she was wet but she didn’t actually physically try to take things further. So we never actually had sex any of the times I saw her and I never felt the need to take things beyond simple kissing. I think that she was one of those ladies that always had it easy with guys. She could just show an interest and bring up sex and the guys would just do everything for her. They would make the physical move and initiate. I don’t think she was comfortable physically initiating things with a guy. I think she was actually shy about that so I was definitely not right for her. Perhaps after the first date I knew that physical spark wasn’t there but for some odd reason I kept seeing her to see if anything would change. Although she was attractive I never got turned on from kissing her. I liked the idea but it just didn’t happen.

I remember feeling like a real dipshit for awhile when I would think of Deni. I mean here is this girl telling me sex was on the table and it never happened. I felt really inept when it came to women. I couldn’t score with an ex-prostitute. For a guy this is a source of embarrassment. My dating life was like a soccer game, a whole lot of running around but very little scoring. This romantic interest of mine left with me some serious issues about my ineptitude with dating. And I already carried that feeling of I suck at this since way back in the 6th grade. And it just perpetuated. So why do I bring this woman up? Why do I still think of her? Why? Because years later when I identified as an alcoholic I remembered her and I remembered where that AA meeting was, right next to the porno shop. In later years this would help me turn my life around.

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