Bob’s First Experience with a Pro

As you know, I enjoy sharing stories from my readers, especially when it involves exploration of new aspects of sexuality (to them).  One of my readers, cum Twitter follower, had his first experience with a professional today, and elected to write about it and share it here and on his blog.  He was so excited; he tweeted about it while he was waiting for her to arrive, so I knew they’d have a good time together and he’d have an experience to share.  Here it is in his own words:

The Background

I am a 59 year old man. I’ve never had a truly satisfactory sexual relationship. There is a long, and perhaps tedious, story behind this dissatisfaction and the long and lasting impact it has had on my life (see the comment by BobF HERE). I spend many hours contemplating this and have learned a lot in the past few years that I wish I had learned much earlier.

I grew up in the late 50’s and 60’s; in the south; as a Roman Catholic. Those three elements go a long way to painting the cultural milieu from which my sexuality emerged. When I was a child, I seemed to be carefree and happy in my relationships with girls. But as I reached those crazy years of puberty, I became shy and apparently unable to enter into any sort of friendship, much less something more.

At puberty, my father passed no information about sex to me at all. Probably pretty typical, but in retrospect it seems significant that the only sexual information I got was either from my mother or from the scuttlebutt that reached my ears and eyes from friends and occasional peeks into my father’s Playboys that he kept hidden in his dresser.

And my mother really upset the applecart very early on. During one of her ‘talks’ I recall her saying to me, and this is exactly word-for-word the way I remember it, “I don’t know what the big deal is with sex. It just hurts.” IT. JUST. HURTS!! Can you imagine the effect that simple statement had on my entire life? I was probably only 11 or 12 when she said that to me. But that line wound its way deeply into my unconscious and it took about 40 years before I finally opened my mind to what was so blatantly obvious had I simply been able to erase that youthful message: women enjoy sex.

But the damage was done. I had squandered my sexually prime years. Without going into the lurid details, suffice to say that I had very few sexual encounters in my life. I married at 32 and stayed in that marriage for 19 years, until 2001. Divorced and single again, I spent the next few years in deep contemplation of what had happened to me. I leave out many important details of the story, but I finally began to get at that underlying issue that had held me back. Sex does not ‘just hurt’ women. What a revelation! What a new outlook it brought to how I interacted with women.

I spent the past 8 or 9 years chasing my dream of reliving the sexual life I never had as a young man. I dated people I met through friends. I dated women I met on various online dating sites. I even tried the hard core sites like AFF, Wild/Bang Match, and Fling; with mixed success.

On the whole I had more sexual encounters in the past few years than I had in any similar period of my previous life. But still feel like it was more work than fun. It was like for every time I actually got laid I had to spend an enormous amount of time and effort to get to that point. And then none of those encounters ever amounted to anything much more than a roll in the sack for a few hours, then it back to the drawing board.

There must be a better way.

The Planning

Enter my discovery of The Real Princess Diaries. Sure, I knew of escorts, but what did I know? It turned out after reading through some of Alexa’s posts and following links from her site to those of other escorts, I discovered that I knew virtually nothing about escorts. And it was about time for me to check it out.

So in early November, I did some research and looking around. I happened into the professional site for a local escort and was enthralled by how she looked and by her apparent intelligence. Her reviews were, well, unbelievable. I mean, I had to wonder, could this really be true?

So I emailed her. I told her flat out that I was a total newbie and had no clue how to start. I sent her the information she had requested on her site from a newcomer without any references from other escorts. She replied to my email in about 20 minutes. It was a sweet, understanding message. She said I had given her enough information for screening. Funny thing is, I told her my whole damn life history. She could have checked out pretty much anything about me she wanted to.

By the fourth email exchange we had selected a day and time. I opted first for a 90 minute gentleman’s hour, but later contacted her to extend it to a full two hours. She asked me to get the room, but suggested a good hotel. Then it was time to wait…three weeks plus a few days. Damn, that was a long time!

During that time I would often look at her site, and imagine what it would be like when we met. Yeah, that’s it…”imagined!” Ha! It was hard to simply imagine. Real hard. *wink*

As the day came closer I found that I was preparing for this ‘date’ like I would for a real date…maybe even more so. I had champagne, a gift card from one of her favored stores, a special trip to get my hair trimmed (nose and ears too, Alexa!), made a playlist of music (didn’t use it though), scented candles, and more. All this for what would be, from all I had read in reviews, about as close to a “sure thing” as a date can be. Short of her finding be totally repulsive, I was pretty sure I was about to have sex with an angel.

The Event

And I did.

The day arrived. I was so incredibly excited that I felt like a teenager with a hot date. That is definitely the best way to describe it. I was 16 or 17. I knew I had to perform well. I just HAD to. So I had refrained from any self pleasures beginning two days before. I also had to make a critical decision that many older (and some younger) men had to make. Do I use the blue pill or not? I have suffered ED, particularly in the waning years of my marriage and then a few years ago during a relationship that lasted about 6 or 7 months. But I don’t always have that problem and I really prefer to do it without the help if I can. I have a supply of the “quick acting” Viagra, so if I was having difficulty I could still count on it kicking in quickly enough, so I decided to not use it. Good choice.

I got to the room early. Nice place. The room was great. A large king-sized, canopied bed. A sitting couch. In other words more places to consider for sex. At 12:55 my phone rang. It was her, driving into the lot and wanted to know the room.

Holy shit. I mean, at this point I am practically out of my skin with excitement – not nervousness. This was simply put just a plain exciting moment in my life. Perhaps a life-changing moment.

At 1, she knocked on the door. I opened the door and my angel walked in the door. My first impressions: “she’s gorgeous”, “she’s tall”, “she has a beautiful smile”, “she looks real young” (she is 32, looked 25 to me from my 59 year vantage point), “she has big tits”, “her ass is fine”, and “OH MY GOD I AM GOING TO FUCK HER!!”

I sort of slipped into a dimwitted horny guy mode for the next 5 or 10 minutes. I’m not going to spill all the delicious details, I think most readers have a pretty damned good idea of what happened. And it was, for me and I hope for her, exquisite. We looked at a portfolio of my photographs that I had brought along to share. She happily complemented me on all the work and spent some time looking at the small set of nudes that have in portfolio. At that point, I ‘m hoping she will consider me to help her shoot pictures for her ads. Opened the champagne. Some fun on the couch, clothes thrown, on the bed… oh, use your imagination (or come visit my blog to read about it in more graphic detail.)

And then. As suddenly as it had started. It was over.

So, we finished (or should I say I finished) right on the dot at 3. My two hours were over. But it had been everything I expected, and more. There were a couple of disappointments, but nothing that put me off at all. In fact the two things could have been more about us being together for the first time¹ and could go away completely the next time.

The Followup

So what did I make of this experience?

I liked it. I sensed that she loves her work. I make this point now because there has been so much recent press about Belle De Jour/Dr. Magnanti and whether or not escorts like what they do. My provider today definitely loves her work. We talked about her passion for it. How it fills her needs (and we were not talking about money). We agreed that having sex like this made a lot of sense for certain types of people.

And it appears I am one of those sorts of people. I am divorced. I live alone. I spend a lot of time online watching porn, reading and writing erotica, masturbating, and generally obsessing about sex. I am not in the least interested in getting married again, or even, for that matter, in any sort of complicated relationship. I am comfortable having sex with total strangers (I have done that a few times in the past few years).

The best parts (yeah, weird I should feel this way because I LOVED the sex) were when we were simply talking and touching one another. It just felt damned good to be able to simply hold one another naked, and talk about sex. To hear her confirm the lesson I finally learned: she likes to have sex! She is loving every moment of this.

Will I do it again?

Simple answer to that. Yes. I have another date with a different escort in a couple of weeks. I have been exchanging emails with another in NYC about a possible date in the City, probably in a month or so. I was referred to a squirter by my provider today as well (thinking it might be fun to be drenched). So I’ll tell you that without question, if I had the resources, I’d see an escort at least once a week. But that is not in my budget. Life seems to step in and change things. Like having to spend $600 on Sunday to get my son’s car repaired (that was what my two hours cost today, so there went a second meeting with her anytime soon).

Is it the answer to my sexual exploration needs?

That remains to be seen. Honestly, I don’t think I can afford it often enough to really meet those needs. I still need to find sexual partners the old fashioned way: Craigslist. Ha!

You can find Bob on Twitter or at his blog.

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