Tuesday, July 29, 2008

I'm Only Going To Be Alive Once

I am now in my mid 40s. In my early 20s, a time when I had very little sex experience, I'd gotten married. We were incompatible sexually, never really comfortable together that way. Still, we had a big group of friends and family. Because of that (and just plain fear of change,) we stayed together for several years.

During this time of sexual frustration at home, I became obsessively interested in streetwalkers. At first I would just go to different parts of town where street prostitutes worked and watch them. Then one day I paid for a blowjob and it was on— every chance I got I was out getting street sex. In the car, in alleys, doorways and parking lots, in the hallways of apartment buildings, once in an airshaft of a public housing project, in the cab of an abandoned truck and sometimes in scary hotels.

It was an adventure, and there was a "thrill of the hunt" almost as fun as the sex. I knew all the different parts of town where girls would be, and which types would be there— from the classier ladies to the crack smokers and junkies.

The really rough, druggie girls were fascinating to me because they were exotic and intense. (After all, I grew up on a farm and had just moved to the city a few years earlier.) I did this in such a compulsive gonad-stupor that I only later gained the minimal empathy required to realize what hellish lives many of these women must have had. I realize now what karmic awfulness I was implicating myself in.

Still, I'm glad for many things I got to experience— the kinds of girls and body types I would have never otherwise been able to explore. Beautiful fat girls, black girls, tiny small girls, tall-like-a-basketball player girls, asian girls, classic blond bombshells, punk rockers, beautiful mature-aged ladies, etc.

Prostitution is often thought of as a disease risk, but I never met a street-girl during this time who didn't carry condoms and insist on their use. I never felt endangered, aside from the possibility of getting jumped or carjacked in some of the neighborhoods I went to for sex (which never happened either.)

Some of the situations were completely odd, but totally fun. I remember running into a cute, funny, curly-haired girl on the street once. I would have never guessed that she was turning tricks until she made the first move of propositioning me. We went up to her room and I laid on the bed for a great blowjob. It was only after this that I noticed that she had a ferret on a leash scrambling around in the folds of her little fur coat.

My obsession pretty much ended when my wife and I divorced. I moved on, found a girlfriend with whom I had harmonious sex so excellent it made furtive back alley transactions seem uninteresting. I didn't look back.

Flash forward twenty years. In the wake of a breakup from another relationship and a series of professional failures, I find myself looking in the Erotic Services section, and eventually I meet up with a few girls advertising there.

It's been a very different set of experiences than before. It's much more expensive (though I feel I've gotten what I paid for.) These girls have been very professional, without signs of drug addiction or desperation. There has been a leisurely pace and a general good humor and friendliness that I didn't experience in the old days. Through the internet it's much easier to access different, diverse and exotic types that would be difficult to find otherwise. Finally, it takes a little research and investigation to find the experiences that are right for you, so be careful and use common sense if you're going to do this.

I met with a gorgeous older woman in her fifties. She was incredible. like nothing I ever encountered in streetwalker days. Gentle, cheerful, thoughtful. She seemed to truly enjoy having sex and talking with me. It was so much like a 'girlfriend experience' that it felt completely natural that I go down on her, which, again, she at least appeared to enjoy. She finished me off with a lovely blowjob. Laying around talking with her, I felt really comfortable. Walking up the block, I still could smell her scent on me. I realized that this had not only been the best sex I'd had with a prostitute, but some of the most memorable sex that I've had in my life, period.

I met with a preop transexual, who was stunning, friendly and awe-inspiring in fishnets and boots. I thought I would be freaked out, but she immediately put me at ease. I had a really fun time learning that the 'girl with something extra' experience was not really for me.

I met with a heartbreakingly beautiful latin lady who gave me a fantastic sensual massage ending with a perfectly controlled handjob. We sat naked in her studio for more than an hour after, idly talking. I could have proposed marriage then and there.

Most recently, a pretty blond BBW welcomed me to her place with cheerful jokes. She encouraged me to come multiple times and there was lots of giggly moving around and shifting of positions. Afterward, we swapped life histories.

As a sensualist, prostitution gives me access to experiences which would be otherwise impossible for me. As a human, it temporarily provides for me a kind of companionship I spend long periods without. I'm only going to be alive once, so I really might as well. (The judgement of others is really the only thing stopping me, and that's pretty easy to circumvent and/or disregard.)

Friday, July 25, 2008

I Partook

My wife at the time had left me, and my confidence was at an all-time low.

I got on one of those phone lines and replied to an "exotic Asian female" as she put it.

I show up at her apartment, and she ushers me to her back bedroom where she has a myriad of sex toys and an half full ashtray.

She comes into the room and starts smoking crack.

I had never smoked crack, but she offered, and my mind wasn't right, so I partook.

Next thing I know, we're high on crack and she's ready to do it.

It was very mechanical and I had trouble getting into it.

After 30 minutes, she said my time was up and we hung out and smoked yet more crack.

I ended up spending $600 for the evening and felt like a hollow shell of a man afterwards.

Monday, July 21, 2008

I Was Smitten

My problem is that I tend to fall in love a little with my "providers," sometimes just a crush, sometimes veering towards more. And it’s sometimes mutual—I’ve actually dated two providers I first met as a client. Truly dated, without paying for the sex. I think it goes back to my young marriage. I was quite young, 19 years old, and I married a girl my age who was so completely sexually open that she set an almost impossible bar for the relationships I’ve had since. We divorced when we were both 23, and for a long time the only way I could experience the kind of sexual intensity I had with my former wife was to date much older women, 30 or older. Occasionally I would date someone my age or younger, but invariably I was disappointed. Younger women, and I know this is generalizing, are just not as comfortable in their own skin. Now, at the age of 38, I realize just how lucky I was with my young wife.

Right around the age of 30, I started seeing prostitutes, always in between "real" girlfriends. I use a local Internet review board and do a lot of research before settling on someone new. For the first few years, it was more about sexual variety—women of different ages, races, body types. And they were almost always extremely sexually skilled. It created kind of a vicious circle: when I started my next relationship, I would long for and expect the sexual competence and freedom that prostitutes often provided. Finally, about four years in, I started falling for a provider for the first time. Her working name was Trixie, and I was smitten the moment I laid my eyes on her. She looked like Bettie Page, tall and voluptuous, and we both felt an instant rapport. The sex was completely off the charts from the very first time. I’ve been with many women and can be a little jaded, but she surprised me with every move. From the deepest deep throat of my life to her actually asking for anal (and coming that way), she initially reeled me in with her superior sexual skills. But then, fuck, she turned out to be smart, as in scary smart. She was more than just a dirty talker... she would spin crazy, creative, erotic stories on the fly, while we were fucking, and by the time an hour was up, I felt as though I’d had sex with a dozen goddesses.

I saw Trixie as a paying client for about six months before I finally asked her out. I took her out just a few times, and we had a lot of fun, as well as a lot of really great sex. Unfortunately, I started having true feelings for her. I remember a really sad moment where the impossibility of the situation hit home. We were having Sunday brunch at a cool little neighborhood spot, and it hit me: "Dude, you’re dating a prostitute." I suddenly realized that this was something I just was never going to be able to explain to most people, certainly not my family, although I’ve since told a couple of friends who didn’t think it was that big a deal. Anyway, that was the last time I saw her as a non-client. I stayed away for almost two years and went back as a client just once before she retired. We had a sweet little reunion, and she told me about her plans for going back to school, and getting married, and moving to a small mountain town. She said, "You know, we probably could have made something work." We had amazing sex one last time. About a year later, I got an e-mail invite to a BBQ at her and her new husband’s place. I had a new girlfriend at the time, and I couldn’t figure out a way of explaining my connection to Trixie, so I ignored the invitation. I think of her fondly now, but haven’t tried to make contact.

Since then, I’ve dated one other provider, and a part of me wants very badly to ask out another who I’ve been seeing recently. It’s sad, because the sex is at the level I desire, and, like so many working girls I’ve met, she’s incredibly witty, big-hearted, and intelligent. But there’s no good end. It would break the hearts of so many people in my life if they knew the truth about a relationship that started that way, and I couldn’t live with myself lying about it. I have a suspicion that I will always harbor crushes and strong feelings for providers. There are worse crosses to bear.

Wednesday, July 9, 2008

I Said That One

I saw a sex worker just over a year ago, but I had thought about it for a long long time. It never seemed like something I could really do. A sex advice column pointed me to an escort review board for my town. Reading through it, I was shocked at the openness of the posters and just how many different services were available. It didn't change my mind, but I kept looking every few weeks, using the advertisements on the site instead of porn to jerk off. The women seemed closer, more real, with a call I could actually fuck them.

I changed my mind a year ago because I was turning 30 and I was still a virgin. At the time going to a prostitute seemed like the only way to do something about it. Even after I had made my decision it took me a few weeks to actually make the call. I chose an incall service near my apartment, I didn't want to meet her at my place and I didn't want to spend more money on a hotel room.

I was so nervous when making the call I barely paid attention to what the operator was saying. I heard the name of a girl I remembered from the website and I said that one. I noted down the information on where to go, but I made a mistake and had to call back twice.

Once I finally got there, I was shocked by how broken down the room was, but the girl was pretty. I handed my money, she told me to get comfortable and she went out of the room for 5 minutes. I had no idea what to do. I removed my clothes, keeping on my underwear. When she came back in the room, she immediately got undressed and got on the bed. She was beautiful, but this is not what I had imagined. I couldn't do most of what I had in mind: couldn't undress her, couldn't kiss her, couldn't perform cunnilingus. She was also weirded out by my penis, I have a phimosis. Still, I was enjoying myself until she got on top of me. She immediately started to moan, and it hit me as incredibly fake. I lost my erection. We spent the rest of our time together lying on the bed, me holding her.

For the next few weeks what I had done would hit me: sometimes it would make me happy, sometimes sad. Now it's just another memory. I stayed away from the review site for a few month, but I started going back recently. I may end up trying again, but right now it doesn't feel yet like I need to.