Ugh!! I wrote this whole thing & then I was told that I wasn't logged on. Rather than copying and pasting, which I should have done, I hit the back button and it was all lost. I don't know how that happaned. If I'm not logged on, I shouldn't be able to write anything, right? Anyway, let me get back to the subject...
I started my original post by commenting on this comment that you made, Merlot: "I'm still not sure entering this hobby was the better choice." This is an interesting observation and one that I have wondered about myself from time to time.
Anyway, back to the beginning. Where was I? Oh, right: Backpage. I don't know how legitimate Backpage is in Canada, but in the US it's completely sleazy & it's LE bait. I searched the ads for years, wondering how I could get into the hobby. I asked the age-old question: "If you need references to see a woman, and no woman will see you without references, how do you get references?" I didn't know the answer, so I circled the Backpage ads like a shark around a bleeding swimmer. Eventually I discovered TER & joined & did some research. This led me to third-party verification services & I ended up joining Preferred 411. When you first join P411, there are very few women who will see you. You still need references! But, a handful of ladies describe themselves as "newbie friendly" & it's these that you have to see first.
So, I contacted one of them & made an app't. This was for 9:00, after I got out of work. I'm a suburban boy, so I had to drive into NYC to meet her. In retrospect, this was mistakes #'s one and two -- now I will never see a woman after work because you never know how tired and stressed-out you will be after work. Also, I tend to avoid NYC. There are plenty of gorgeous providers in Northern NJ or Long Island and I will go out of my way to see them first. Some amazing ladies are exclusive to Manhattan so, yeah, I'll bend my rule for them, but I try to stick to it if I can!
Anyway, I texted this girl to confirm my app't and she got back to me with the hotel she was staying in. I did a little research, found parking near the hotel, so all was good. Just before I left work, she texted me and asked if I could make it at 10:00 instead of 9. I said, "Sure, no problem," even though I wasn't happy about the schedule change. I live in the opposite direction of the city, so after work I drove down to a mall and just hung around in the parking lot to kill time. When the time came, I drove into the city & parked my car. At 9:59 I texted her and said I was there. She texted me back: "You're here already?? Give me 15 minutes" So, I wandered to the other end of the block and waited next to a homeless guy that was sleeping under a staircase. At 10:15 I texted her again & she gave me instructions to take the elevator to the third floor & text her again. Before I could even get there, she texted me, "Where are you?" I said, "I'm here!" She gave me her room # and told me to tap lightly on the door, which I did. So...
...she opens it up. Now, she had described herself on her web site as "slender" and was described on TER as "skinny". She was neither of these things. Her belly was bigger than mine. I came into the room and this flashed through my mind, but I thought, "Fuck it!" I had gone through so much time and bullshit to get to this point that I didn't care. We stripped, which was interesting in itself. The question of "Can I strip in front of a woman I just met two minutes ago?" was answered. Yes, I can. We showered together, which I think was just a way for her to kill 15 minutes. She did give me the most unusual compliment that I've ever received, though, which was: "Wow! You have a really clean asshole!" "Oh... Thank you!" I said.
So, to bed. She went down on me for a while, rode me CG and RCG, and on to doggy, and it never happened. I don't know if I was too nervous or if I wasn't very sexually attracted to her. I think it was a bit of both. She was disappointed that I didn't cum & I felt bad for her. I think I felt worse for her that I didn't cum than I felt bad for myself! I think I actually apologized for not cumming! She knew I was nervous, so she gave me a shot of whiskey before we started & even though I kept saying no, no, no, I eventually relented and took the Xanax that she offered me. It didn't help. It made for an interesting drive home, though. I had to get off the highway about 2/3 of the way home and drive the back streets for fear that I was going to crash my car. These are learning experiences & I learned a lot of what NOT to do that night.
Now, my 2nd experience, that was a good one...!