My first experience with a SP - read it all, it's funny, sad and pathetic
My first experience with an escort was this spring in Montreal. I’m from Toronto so I thought this would be a great chance to try something new. I booked a really cool downtown hotel that has at least a 4 star rating. I planned a four hour date – dinner and dessert.
I’m a middle-aged man, married for a long time. I’m social by nature, reasonably successful, and I present pretty well. I am comfortable around women as friends, socially, and professionally. I am pretty confident in myself and I don’t try too hard. All in all a pretty good package, imho.
Booked with an indy, who has since retired after about a 5-6 month stint as a sp. Beautiful girl, around 28 years old, educated, auburn hair, pretty face, awesome ass, and 36D breasts! I’d say she was about 5’7”. There were no reviews or even a mention of her on MERB. That did not concern me. I read a couple of glowing reviews from CERB, the board that only provides recommendations not reviews. I thought things were set. Emails back and forth with her seemed fine.
We meet for our date in the funky bar of my hotel. She’s dressed pretty plainly. Sweater and slim, maybe stretchy black pants tucked into average boots, somewhat scuffed. She mentioned that she dresses discretely on her website, so I guess this is what she meant. I could tell within 20 seconds that she was not into this “date” at all. No smiles, no flirting, no laughter. Ok I thought I’ll just charm her over dinner.
At a nice restaurant within walking distance of the hotel, we dined. Good food, even better wine. A nice California white because she preferred white rather than red. We talked, it was dull. More like a dinner with a colleague whom you didn’t have much in common with. She was educated and a mature student in a field sort of related to my profession. We talked about movies, music, that sort of stuff. I like arts and culture, so I’m not out of my element here. She was very interested in Japanese movies and directors. Pretty interesting stuff and not something I know much about. I was happy to listen. There was no chemistry whatsoever. Her body language was that of an uncomfortable person, leaning back. She spoke softly and was hard to hear.
Walking back to the hotel for the final two hours of our evening we simply walked side-by-side. The vibe I got was that she did not want to be seen on the street, at all. She seemed a little nervous. Up in the room, which she liked, things did not improve. She disrobed, kick-ass body. I moved in for a light kiss. No tongue or anything. What? No kissing? Oh, and stay away from those breasts. I asked about DATY. She said “Why would you want to do that?” I remained calm. She did a CBJ, for a while. It was fine, but my wife, who is an amateur btw, is much better. On to CG. What, we have to switch condoms I thought? It’s not like I came. I kept this comment to myself because I wanted to see where this was going. The next while, it could have been 45 minutes, we switched positions, changed condoms, and I did not come. Wow. It’s not hard to make me come. My dick had figured this girl out and knew the evening was a waste of time for both of us. Oh, and at one point I asked about DATO – just as a joke. I got a stern look.
Later, after I gave up and we laid on the bed, killing time and having some pillow talk, she loosened up a bit and laughed some. She was actually warmer then than at any other point during the evening. Warmer, but not really warm if you know what I mean.
Our time ended, she dressed and left. My balls were blue. I felt frustrated and upset. I didn’t sleep for hours. For whatever reason I may not have been her type, but she should have been more of a professional. I was never rude, unkind, or negative even as the evening was in its death spiral. I guess it was doomed from the beginning for reasons known only to her. Perhaps she just had a fight with boyfriend who didn’t know about her part-time job (she told me about the bf during our pillow talk). Maybe she didn’t like what she was doing with her life. It could be that she distrusts middle-aged men in Italian suits. Who knows?
She sent me an email a couple of days later with some recommendations on movies and Japanese cinema. I suppose that was kind of her. No mention of our evening and how it went. Wow.
I suppose I could have trashed her on MERB that evening. I wasn’t sleeping anyways. But, I just can’t do stuff like that. I’ll either tell her directly what I think, or I’ll keep it to myself. She was not evil, mean, or dangerous. She was, in my opinion, just not good at her job.
I moved on and have seen a number of sp’s since then, with much better success. There’s one in particular that I have an awesome time with and I see often and is very friendly, within the confines of our relationship. I’ve made a few mistakes along the way, but nowhere near like the one I made the first time.
So ladies and gentlemen, that’s the story of my first time. I hope you enjoyed it. Oh, and did I mention, I paid $1000 for the pleasure? You can stop laughing now.
