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.)

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.

I'm a Young Black Guy

I'm a young black guy with a thing for older voluptuous white women. Prostitution has helped me realize my fantasy. My most memorable experience was with a single mother. We set a date at a hotel. She got some candles, started with a massage and we started having a nice conversation. Her body type was prefect for me: slightly saggy big breasts, round belly and nice ass. We got a great time together. 5 minutes after fucking, she started telling me funny stories about her son, the apple of her eye. We talked about normal stuff, like old acquaintances who had already met each other. I'm still struck by how giving she was by telling me about her son. Maybe she felt like I needed a little more confidence, she even gave me some nice compliments. Those lasted more than 1 hour.

I keep thinking of how nice it would be to keep my head buried in her chest, for protection. To only leave it unless absolutely necessary.

I have not tried that hard to explain my preference for larger white women to myself. Maybe I'm afraid it's based on this horrible stereotype of white women that I'm not even aware of. Maybe I'm afraid to put black women in perspective in this too. It's hard enough to talk about sex without putting race in it. As for my age preference: maybe I'm looking for a mother-son relationship.

I Like Women

I'm 41 and divorced. I have had a few girlfriends since breaking up, but the combination of a demanding job and the fact I spend most weekends with my children means I am usually single.

I have a high sex drive - not freakish, but I like sex, and I like women. I started seeing working girls after I'd been single for 6 months, and have had the usual range of experiences - I even made friends with one of the girls.

A few weeks ago, I arranged to see a girl who advertised on a web site. Her online persona is very much the crazy cumslut porn queen - she wears exotic make-up, has huge silicon boobs, and in her blog wonders if she's a slut or a whore.

I visited the hotel where she was staying, expecting a full-on session of filthy porno sex - and I wasn't disappointed. Thing is, afterwards, we chatted for a bit - and she opened up to me, a total stranger who had paid her for sex - about her life. She showed me pictures of her cats, told me about her no-good ex husband, how she was hoping to move to a remote place and just have lots of animals. She told me about her boyfriend, and how her submissive bedroom persona was matched by a bossy and demanding real world attitude.

I fell a little bit in love with her - wanted to hold her and make her feel safe. Of course, I knew that to her I was just another nameless guy with a hard-on, so I suppressed the feeling.

I Had Also Done Many Things During Two Deployments I Never Wanted To Do

Where to begin.

I'm a mid-twenty-something, currently in the military. I have a stable girlfriend and several unstable yet available female friends. I am vastly overeducated for my job and am generally a well-respected person. I'm not too shabby in the looks department and am very seldom ridiculed. Generally being gone for a year at a time overseas is a terrible experience. Every time I've gone it's been a miserable series of events that makes suicide seem palatable. One day I decided to visit Toronto with some friends. After a complete failure at the bar scene I decided I could part with some money for some stress release. I had never bothered to resort to prostitution, but I had also done many things during two deployments I never wanted to do. After the concierge at the hotel was appalled by my request for female companionship, I hailed a cab and asked the best place to find a professional. He suggested the intersection of two streets named Church and College respectively. This was very comical to me, but I was eager to begin the adventure. Upon arriving I found a gaggle of women who were wearing what could only be described as whore uniforms. I decided on a young blond who seemed to fit the part. Negotiating the price during the cab ride back to the hotel, we eventually made our way to my room, finding many odd stares from hotel guests and the staff. This part was actually very exciting for some reason. In the room things began very fast, and while thrilling it was obvious she was doing her job, which in a way was more arousing. After a seemingly endless 35 minutes of nervous thrusting, I managed to complete my task, which seemed the most satisfactory part of the evening to her. Pleasantries were exchanged, and I handed over her garish clothing and sent her on her way. After a cigarette and some self soothe saying, I managed to convince myself somewhat that the money was well spent and that I had a "good time." I would possibly seek companionship in this manner again, but honestly it was a frightening act of depravity fueled by a complete loss of morals related to my murder for hire status in the military.

I Told Myself I Was Just Being Honest

Have I ever been with a prostitute?

Yes.

Why?

Greed certainly. Adventure maybe. Relationship challenges absolutely. For a time I told myself I was just being honest and that the professional sex worker offered a degree of honesty. But that's all bullshit.

And what was my experience of the girl?

Girls. The experiences have been varied. Talent-wise, I've had three girlfriends that were better than any pro.

My first was in Tel Aviv. A Romanian girl--way too young for me but irresistibility beautiful. I felt like a thief but that didn't stop me.

The best pro was in Mexico. She was older, closer to my age. We did the hour thing in the hotel next to Adelita's. That's in Tijuana. I liked her so I made a deal. I told her, "Puedo una esposa por la Noche, no puta, una esposa. ¿Entiende? Y yo creo usted esta perfecta. ¿Entiende?" She smiled and said, "Yes, I understand. Perfectamente." I took her back to the hotel, past the disapproving doormen (it was not that kind of hotel).

She was a pro. She did know exactly what I wanted. Honestly, mostly we just lay there in bed watching Mexican TV, ¡El Channel Historico! She ordered me a fruit platter from room service. Not for her, for me. She took care of me. Mostly, we just held each other. Perfecto.

It made me realize that what I wanted was intimacy, not sex. I've come to see that as dangerous to try to get from a professional.

So I keep my experience limited to travel. I rarely use a professional at home. I understand what I want and what I can get are two very different things.