Whether you’re crunching numbers at a cubicle or stuffing a ball gag into a grown man’s mouth, the first day at a new job can be intimidating. Escorts of Reddit were asked to share what happened at their first day at work. From nervous butterflies to a 50 Shades of Grey-esque ass fetish, here are 7 of the most enticing stories.
He was just looking for a blowjob, so I saw it as a very easy job, but then he wanted to talk for a while first. He was talking about Opera and I mentioned having sang a certain piece in choir, so he ended up asking me to sing, which was really strange, then told me to get on my knees and get down to business.
The first blowjob was pretty normal. He had asked if he could cum on my face and/or tits and I’d said OK, so I was expecting that. It just seemed like it took him forever to cum and he had this whole deal about grabbing my hair while doing it and going on and on about my hair (it’s long and red, but nothing really special). After he came, he put his dick back in my face, so I assumed he wanted me to lick it back clean, so I did, and he told me to suck him hard again. Then he told me we had 20 minutes left and told me to lay on my back on the bed, with my head off the edge. I figured he was going for sex and reached for a condom, and instead he told me know and that he wanted to “face fuck” me. He came a lot faster that time, pulled out and came on my face and I could feel it running down the side of my nose toward me eye. He yelled at me not to wipe it off and to leave it there until he left, then asked me to stand up and sing for him again while he was getting dressed. It was kind of surreal.
I was extremely nervous but I had an experienced girl showing me the ropes. We had posted single ads and duo ads and my first call was asking for a duo, which made me feel a lot more comfortable with he whole situation. So I get all dressed and am about to pee myself waiting for this guy to knock on the door. He was a pretty good looking 40 ish year old businessman. Then he explained his fetish… He wanted us to feed him his cum. So we both fool around with him and he ends up banging me while my friend watches. Then he’s ready to go… He finished on his stomach and I scooped it up with a spoon. Had to force him because that’s what he was into. I felt pretty gross, he got dressed and left and I made a quick 120 bucks. That call definitely broke me in for the rest of the calls that day as they were all normal. I have seen the guy a few times since then. We call him the cum guzzler
Tl;dr my first call ever was a guy who liked to be force fed his own jizz.
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 blowjob. 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 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!
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.
I had two clients my first day.
The first guy was really nice. Mid 30’s, extremely average looking. We started out with small talk. He offered me a bowl, which I refused. He smoked a little and then eventually kissed me. He had a bit of an ass fetish, I let him eat my asshole and lightly spank me, and then I let him put it in my ass– I figured that it was my first client, I should do a good job. I still see him from time to time, and he always tips very well.
The second guy didn’t even try to have sex with me, he wanted me to smoke a cigarette while watching him masturbate. That’s about it. He paid me for an hour without question and I never saw him again.
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 dick 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.
Photo by Chulkova