1. “Emotional attachment”

I’m an actively working girl. My first time was only about a month ago. It was through a website where you make offers to pay a girl to go on a date with you. They had to be very clear that it was’t a prostitution website (you compensate for time it said, many many times) but sex was fairly well implied.

My first time was with a 43 year old married man in town on business. He had contacted me about a week prior, through the website, offering £200 for a date. he said he would give me £3000/month for regular sex if we liked each other. I said yes, and he told me which hotel to meet him at and when. He also told me what to wear.

I arrived and he wasn’t too bad looking–slender and way more tan than you normally see as far north as I am. He bought me a drink first at the hotel bar and we talked for a bit. I was unbelievably nervous, but he was fairly reassuring. I was sure everyone knew what I was there for, and I was terrified of anyone calling me out.

Eventually he suggested we head up to his room, and I gave the meekest “okay” that has ever passed my lips. We went up and sat on the bed and chatted a bit more before he kissed me. after a couple seconds he pulled back and said “i like the way you do that. Let’s take off your clothes, and see what else you do well.” I got naked and gave him a blow job. I was’t really expecting him to finish that way, but he did.

After that he laid back on the bed and indicated I should join him so we snuggled and talked for a bit more.

Eventually he told me that he thought I was funny and sweet and “too good at that” and that he didn’t want to see me again in case he formed an emotional attachment. He said he just wanted sex, he didn’t want to mess things up with his wife. I said that was fine and we talked some more.

Eventually I started putting my clothes on. I was waiting for him to give me some money, but he was’t making any moves in that direction, so I sat and talked with him a little longer. Eventually I reminded him that we had agreed on £200 for the date, and he acted all surprised. then he made a show of looking for his wallet and then counted out each bill and dropped it on the bed as he did. I took it and left, not accepting his offer to call me a cab.

I felt pretty gross. My later experiences were better.

 

2. Cried after

My first job was a private client, and I was totally calm on my way there and during, it wasn’t until I got into a cab to go home that I started crying. I wasn’t even upset, It was just involuntary.

A month later I joined an agency my first night they gave me this guy who became my first regular, always booked half an hour and I never stayed longer than 10. The other job of the night was in an office in an old industrial estate, two very married man and another escort. She was really nice and reassuring and helped me get over the initial embarrassment. The rest of the night was just sitting in the car with my driver talking about life and listening to Frank Sinatra.

Most of the time I even had fun! But I still always got butterflies on the drive there. I think it was the anticipation of not knowing who the guy was, they could he sincerely nice or they could be a complete jerk.

3. Lucked out!

I was an independent escort for 4 years. My first night, I was ridiculously nervous.

I went to an upscale hotel, nervously walked thru the lobby, hoping I looked like I belonged there, and not like what I was really there for. I was nervous the whole elevator ride up to his room. I walk to his room, lightly knock on the door. He opens the door, says (for the story’s sake, we will use the name Sarah) “Hi, Sarah?” and like an idiot I reply with my real name. We laughed it off. It was quick, 10 minutes. He was polite and clean. In the area for business. I ended up seeing him a few more times over the years, always very nice. Tipped on top of the hourly rate, which was always appreciated and made me choose to see him over other clients in the future. I have dozens of other stories if anyone is interested in hearing!

4. Male esscort

I’m a straight male escort and my first day of work was definitely not what I expected. I had (female) friends in the industry so I already knew what a normal job would be like. It’s the same regardless of gender.

In a typical booking, you meet, chat for a bit, sort out business, ask the client to shower then get down to business. For me, that generally includes a massage, foreplay, sex and a fair bit of conversation.

For my first booking, I received an email from a girl that basically went as follows:

“Hi, I’d like to book you as a birthday present for my friends 24th surprise party.”

No worries, I can do that…

I turned up early to help these girls prepare the surprise and they’re all insanely attractive. Out-of-my-league attractive. The girl who booked me then drops this bombshell on me:

“Oh, by the way, all of us girls are either escorts or strippers.”

Uh oh, I’m in way over my head…

I do my best to remain calm and collected and we all enjoy ourselves before the birthday girl shows up. They all turn out to be lovely girls and we all had a fun night. No actual sex but there were a few shenanigans that went on.

At the end of the day it was a definite “thrown in the deep end” experience but one I’ll never forget.