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9+ Escorts Talk About Their First Day on the Job

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These posts from Reddit shine a light on a segment of society that most of us will never know about: people who work as escorts.

Take a look at their stories about what their first day on the job was like.1

1. Dominatrix

“I was a different type of sex worker, a pro Domme. My first pro session was terrible! He was a good client, however anything bad that could have happened did happen…Including cracking his rib during a trample session (very rare when everything is done correctly). However I never had an issue after that first session, ended up with quite a few wonderful regulars.”

2. Loved the rush

“I drank a heap of wine before I went to the agency. This was about 2.5 years ago when the industry was booming. I did booking after booking and went home with a massive wad of cash. I didn’t think about it too much. I just loved the rush of being booked and making so much money. The industry is dead over here now and I have no idea why.”

3. Sarah

“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 storys 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. Obsessed

“I was registered on a few escort websites. I had to pay to post my ad and be a member, and potential clients had to also pay to see my contact information. It kept the “craigslist” type people from contacting me, which were always more of a hassle then it was worth. I saw this one late 40’s, retired military man. He became a twice a week regular for quite awhile. The regulars are always the best.

You already know what they like, there’s no nervousness, and they usually tip on top of the rate. The regulars I did see in my home, I had a separate bedroom from my bedroom to see them in. He ended up becoming a little obsessed. Ended up giving me a quite expensive Rolex, which I ended up selling and buying a car.”

5. Male escort

“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.”

Uhoh, 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.”

6. Didn’t realize…

“My first time and only time as a male escort, I didn’t realize that I was.

I used to hair model from time to time for wedding photographers and hair salons, so I have a few headshots floating around on different modelling websites and stock images. One day, I got an e-mail from a photographer that said he was practicing drawing and needed a nude male model to practice form. He said that he had a studio he could book and would pay $100 for two hours.

I was saving up for a plane ticket to come home to surprise my parents for spring break, so figured this would be an easy way to make a connection in the art industry as well as pick up some cash. We agreed on a time, he gave me his number and we talked on the phone to voice verify, as well as the studio that we would be working at.

When I arrived at the location, he was waiting there and said that the studio had been booked out to the night, and so he asked if I wanted to grab some food and then head to a hotel so we could just pose and draw there. I agreed.

We had dinner, made small talk about church and what I was studying at my University, and eventually got a cheap hotel room in downtown Nashville.

Eventually I got naked, and he asked if I thought I could get an erection so he could draw it. I said maybe, and he asked if he could help. I declined at first and attempted to get an erection, but eventually he said that he wanted to help and came over to me and started j*****g me off. I didn’t know what to do, as he was significantly bigger than me. I started to try to get up but he laid on me and wouldn’t let me move. He kept saying “shh” and told me that everything was going to be okay and he would get me back to my dorm in an hour.

I gave up struggling and he gave me a b***job while he laid on me and kept me down. I was so scared that I came in about 2 minutes. I didn’t say anything as he got up, tossed me my clothes, and said “let’s get you home.”

He drove me home in silence and as I started to get out of the car he grabbed my arm and said “I hope that was fun for you too, i’ll let you know if i need any more fun in the future,” and dropped two 50s on the seat.

I went back to my dorm and cried, not knowing if I just became a prostitute or got sexually assaulted.

Sometimes I get contacted by him, and got a couple messages from him while he was drunk, but I just ignore them and try to forget about it.”

7. Working girl

“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 $80 for a date. he said he would give me $2000/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 chatteda 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 b***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 $80 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.”

8. Butterflies

“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 world war 2 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.

Edit: A few people have been asking about my education, I am a med student in one of the more expensive parts of London. UK student loans are based on household earnings. My family are quite wealthy and I have a few pre-existing debts. Thus zero money.”

9. I never went back

“This sounds awful, but I was so desperate for money that I posted on Craigslist. Obviously that was stupid and dangerous, but I was 17 and I didn’t think about it. I basically asked people to bid to see who I would go with. Keep in mind this was a suburb in the midwestern US, so the money wasn’t crazy. I ended up driving 45 minutes to meet a guy who then drove me to his house. Again, so stupid. I can’t believe I didn’t die that night. This dude was like 50, heavy cigarette smoker, smelled like booze. I told him I was 19. (So stupid.)

The guy paid me $60/hr for three hours. He smoked a few bowls, talked about jazz, and then very creepily went on and on about my boobs. I jerked him for like 30 minutes with this horrible rose-scented lotion, blew him, and eventually we had sex. I was impressed he could get it up with how high he was and figured he must be on something else. That’s mostly what I was thinking about the whole time.

I didn’t feel it when he came because I was too concerned trying to give a good performance. So awkward, but he didn’t seem to notice. When I got off him there was no condom on his d**k and I freaked until I realized it was still inside me.

We “hung out” for a little while (read: he slept and I tried not to puke) and then he took me back to my car, filled up my tank and gave me $300. All in all, not a horrible first experience, but also not wonderful. He’s called me a few times, but I never went back.”

10. My girlfriend

“Just after high school, my girlfriend got a job as an escort. It was back when pagers were cool, for reference. I dropped her off at work on her first night. The place was in a strip mall, just a little spot that looked like a half-empty travel agency or insurance shop. It was out-calls only, so you basically wouldn’t know it was an escort service. I hung out in town, because she said she’d page me if she needed me to come get her.

She paged me pretty quick. I picked her up and we drove to a McDonalds and got coffee. She was a wreck. She said that she told them she was going on a break, but that she wanted me to take her home. She wasn’t even going back to get paid.

She went on an out-call, to a guy’s house. They had bouncer-like guys to drive the girls places, and so a guy drove her to some guy’s house and waited outside in the car. The customer obviously wanted to have sex, and she was totally blindsided by this. I honestly don’t think she knew that she was a sex worker. She thought she was going to be a “go out on the town for a date” kind of escort. She even wore one of her nicest dresses.

Long story short, she ended up just watching the guy masturbate before fleeing the place and getting driven back to the office. Then I picked her up and she never went back. The thing I remember most clearly was when she was describing it to me. She was disillusioned, incredulous. “There were pictures of his wife on the walls! Pictures of his family!”

She was a great gal. FYI, from what I know via Facebook, she went to university, traveled the world, has a beautiful family and a successful career. Happy ending.”

11. Strangely empowered

“No longer an escort (only saw a few clients and decided I’d rather make money the normal way) but here’s my first experience. Signed up to an escort & cam girl site, my partner couldn’t accompany me to the meet so I got my gay best friend to drive me. It was in a Travelodge (classy!) And I was super nervous. I’d asked him if there was anything in particular he wanted me to wear, and he had said he wanted me in casual clothes and no make up. Of course, guys don’t really have a clue what girls look like without a stitch of makeup on so I put on foundation, blush and mascara and a cute sundress.

The guy was around fifty (I was twenty at the time) and he mainly wanted to make out and cuddle. For some reason he had covered himself in talcum powder which was odd, and he wasn’t attractive which made it hard for me to get aroused but he seemed very happy. The thing that weirded me out a little was he kept talking about how young I was and asked me for my real name several times (I had a fake name for obvious reasons). I was reluctant to give him my real name and instead just gave him another fake name – I told him my real name was Elizabeth but my friends called me Lizzie and he called me Lizzie for the remainder of the appointment – then had the cheek to try and haggle me down for an extra hour which I declined. Afterwards, when I was 300 quid richer for an hour of “work”, I felt strangely empowered.”

12. Wasn’t too bad

“I was 22, just graduated with a BA in a major that would make me no money. Moved in with my parents and was on a downward spiral. I posted on Craigslist ($400 an hour, I had no clue about rates and still don’t but from this thread it seems high) and met a man the next night at his house for an agreed-upon 30 minutes. We sat on the couch and talked a little bit. He ran a small business, divorced, overweight, 40s. Really ordinary and quite nice, actually.

He took me into the bedroom and there were lit candles and a bottle of lube on the nightstand. I wouldn’t kiss him for awhile, but he seemed lonely I guess? I eventually did. (Stupid, probably.) He put a condom on and I bl*w him for awhile, but he didn’t stay hard consistently. I climbed on and rode him and he didn’t come by the time the 30 minutes were up. I liked him, so I kept going until he finished — maybe another 20 minutes? I didn’t charge him for the extra. I didn’t enjoy it as much as I would with a regular partner, but it wasn’t bad. After we finished he thanked me and we hugged. He suggested that next time he make a spaghetti dinner and we could eat and get to know each other.

It wasn’t as bad as I had expected, and I wasn’t traumatized, but I never did it again. I’m not sure why. He texted me several times after and eventually I told him I’d moved.

Sorry for the stilted writing, I’ve never told this to anybody before and it was kind of strange typing it all out.”

13. Better than I expected

“This was only a few months ago. I haven’t made the best decisions in life. I was still 18 at the time and I moved out on my own. I started having a hard time making rent so I started posting ads and going on “dating” sites. I got a lot of attention and started to talk to a lot of men but never actually went through any of it. That was until a month later or so and I got desperate and finally accepted an offer from one guy I had been talking to for a while. He was in his 40s, from another town, and offered me $900 for the night.

When the night came along, he booked a hotel, and I went over there some time that evening. I was so nervous, I could barely speak a word when I got there. He was an average looking guy. I wasn’t attracted to him but it didn’t cross my mind that it mattered. I was still about to have sex with someone I technically just met, and for money. He ended up offering drinks (yes, I know how stupid this was now that I think about it) and I got drunk enough eventually to relax a lot more. Once I was relaxed, he started kissing me, we eventually got naked, performed oral. We had sex twice and he got off in less than two minutes each time. Which was a really good thing because he was bigger than I expected too. After that, we just went to sleep and I left in the morning. yes, i stayed over night which was probably another dumb thing to do but oh well.

I guess it ended up being better than I expected but maybe I was just luckier than some girls here that he wasn’t too creepy or gross. Since then I’ve only done this twice more but not with him.”

h/t: Reddit