21 Male And Female Escorts Describe Their First Day On The Job

via twenty20/santiago__cervantes
via twenty20/santiago__cervantes

1. It Completely Turned My Life Around

I was from a small town and really sheltered, but had lost both of my parents and my foster family kicked me out at 17. I stole some of her shit, pawned it and made my way to a greyhound bus that took me to a big-ish city. I found a job on Craigslist looking for women with an interest in massage, cash paid daily, no experience required. Awesome. This was in 2008. I had like 12 dollars left to my name.

I worked there a few months without ever touching any dude’s genitals. I think they kept coming back because I’m pretty and do actually give a decent massage. Anyway, a few months in I figured out that a handjob basically doubled my income. So I popped some of those off.

Working at that studio was NUTS! I was hungry for money, so I’d work open to close 6 days a week. I became really popular and the boss said he’d never seen someone earn money like I did. I got to keep my tips and split the hourly rate 60/40 with the boss. I was clearing like 3k a week. I saw C list celebrities, super rich old dudes, athletes, everyone. One of my regulars was a cop. He came to see me and was like “don’t come in tomorrow and tell no one I told you”.

Anyway, they got busted.

A girlfriend of mine and I worked together for a while, splitting hotel rooms and stuff.

Now I’m back in school. I work part-time at a real job that I like. I’m in school full time. I own my own home and my car is paid off. I live beneath my means and still have stacks of cash from the Jack shack days. I also have an unpaid internship that’s going to be great for me when I’m done with school. Now, I have seven clients. They’re all married dudes. Some I see weekly, some monthly. It’s sort of like I just have seven part-time, low maintenance boyfriends really. Oh, except they leave cash on the table.

This experience hasn’t been traumatic for me at all. It’s helped with my negotiating skills, it’s made me more comfortable around people, it’s made me sharper and more aware. I know it’s dumb, but I love it.

2. I Made $5,000 Masturbating Five Times

I met him at his 5 star hotel and he had bought me about $400 worth of sex toys. All he wanted to do was watch me cum with the vibrator he had bought me. After I came, I gave him oral until he came and he then gave me $1000 AUD. He let me keep all the toys too. On the train ride home I couldn’t stop smiling because I was so happy. I saw him maybe 5 times and we still didn’t have sex. So basically I gained $5000 for masturbating five times.

3. She Had To Do Things Wives Wouldn’t Do

I’ve worked as a male counterpart with a female escort before when clients requested a couple. the whole thing depends on the clients personality though, my escort partner had rough time of it as many of the clients wanted what their wives wouldn’t put out, so she often went home and sat on an ice pack, though other girls I knew in trade got paid up to £3000 for an all expenses weekend abroad with true gents. Hit and miss, use a website like adult work dot com and read the client feedback and reviews

4. Stayed A Virgin The Whole Time

I was pick of the pack since I’m a virgin and some guys are really into that. There are four girls at my club that remain virgins to cater to these guys because it’s a pretty common fetish. I was nervous as hell, but I knew that I was chosen by that client specifically for my lack of experience (minus training), so there wasn’t much point in hiding it.

All the girls were super supportive before I left, giving me lots of tips. I met up with a not totally unappealing, wealthy business type. Pretty typical client. I went to an event as his girlfriend, got a few drinks, ate a nice meal, made conversation. We actually had a lot of fun coming up with my back story on the way there. How we met, my name, etc.

We went back to a hotel room and he wanted a dance. Granted. Then some dry humping and oral sex. Granted. He really, really got off on the fact it was my first time, and that he was my first client. Spent most of the night there – he didn’t push the no penetrative sex rule. He ended up giving me $3000.

I was really wound up all the way home, and honestly, I’d never seen that much cash in my whole life. I’d heard other girls say they’ve done this, and I guess I couldn’t help myself either because the second I got home I masturbated with the wad of cash in one hand because I was so turned on from the nights activities + money. I knew it wouldn’t always be like that, but oh my god. It’s been two years since then, and he’s still a regular of mine. I haven’t told him yet, but I’m pretty sure he’d love it.

5. Here’s What “Full Massage” Means

Well my first day was an interview. I was a nude ‘masseuse’ so the interview basically consisted of giving the owner a rubdown. He came out with a towel around his hips and I wasn’t really sure what to do. I was like 95% sure that I was supposed to give him a handjob, but pulling someone’s towel off and grabbing their cock is something which really requires 100% certainty. So, I did a basic massage for about twenty minutes before he says “this is a full massage.” So he got his happy ending and I passed the interview. He showed me some massage ‘moves’ but honestly, I was better at it than he was and never really used them.

Then I got a tour of the facility- two massage rooms, hot tub, showers, case of sex toys for sale, laundry room, and also the BDSM room for people who liked spanking. It was pretty tacky, a lot of red lightbulbs and signs that say “thanks for cumming.” The owner was incredibly sexist and racist, so much so that it seemed more like an act than something that was actually part of his personality. He had a little white dog named after a nearby suburb, because it “started off white and then got all black and dirty.” That sort of stuff. On the other hand, he was a dead ringer for David Duchovny. He and a Scully lookalike used to do parties.

After the tour I spent most of the time hanging out in the break room waiting for clients to show up. The dude called all his regulars and told him he had a new girl, so I got a fair amount of business the first couple days. In between clients I read “The Terror” which is a fantastic book, incidentally. The other girls didn’t really get why I would want to read a fictionalized account of a historical mission to locate the northwest passage. Mostly they were on the phone having arguments with their boyfriends. I think a lot of them were having sex with the owner. He asked me, but he wasn’t paying, so I gave it a miss.

The second client I had offered me extra for a blowjob but I was pretty set on sticking to handjobs. That’s what the job advertised for and that’s what I felt comfortable doing. I think a lot of the other girls did extra things for extra money, but everything was discussed in euphemisms so there was really no clear way to work out what was expected of me or what I would be receiving in return. No one could speak clearly because there was always the possibility that the other person was a cop.

I only lasted a few weeks on the job. A regular came in and I guess he was used to the other girls doing extra stuff. He asked if he could massage me, which was a fairly common request, but once I was relaxed he started to fuck me. I panicked, he panicked, it was bad. He seemed genuinely confused which made it really hard to come to terms with. You can’t really say “I was accidentally raped” without starting a fun and exciting round of the blame game. Anyway, that was my last day.

6. I Couldn’t Stop Shaking

I work in a brothel. And my first night was terrifying. So much so, that I didn’t make a single cent. But I went back the next night and persevered and was assigned a friend and from there it was awesome! My first client was a house reg, and I couldn’t stop shaking. But he was really sweet. My mentor and i have become best friends and i have turned it into an amazing business for myself!

7. I Expected To Feel Degraded But I Felt Worshipped

I put my ad up on a website. He replied. We set up a meeting, he paid for the room and got there first. I was so nervous. I imagined being arrested for prostitution, my picture in the paper. What would my family say? I imagined being choked to death, unable to scream. So many horrible thoughts. I regretted this. I shouldn’t be doing this. This is horrible, karma is going to get me.

When he opened the door, he had this welcoming, warm smile. We began making out. And really all that happened after that was 45 minutes of being eaten out and less than one minute of sex at the end that I wished would have lasted longer. He offered extra money at the end.

I absolutely was expecting to feel degraded and used at the end of this. Instead, I felt like I had just been worshiped. We kept in touch for three years afterward. On the drive home, I said to myself, “and to think I’ve been doing this for free all this time.”

8. Not A Modeling Job After All

I didn’t know I was escorting.

I was just out of undergrad and working part-time. I was broke and desperate for money and trying to find a second part-time job at least. I started browsing ads for “adult gigs” on craigslist as well as creative gigs, etc, when I came across one advertised as a modeling job.

I’d done some amateur modeling, some “shot girl” type work, band promotions, etc. so this was my usual sort of gig except that there was more nudity I figured. I called and went in to interview.

The woman who ran the agency asked me a few questions, one of which was if I knew what the job really was. I said I thought it was just modeling and posing, and she said it was “more like a stripper job without a club setting”. I told her I couldn’t dance, but I was okay with that and willing to learn.

My first night a few days later was not particular scintillating because I still didn’t really understand what was going on. In retrospect, I feel bad for my first couple clients because they didn’t get what they paid for at all compared to later on when I knew what was expected of me.

Once I figured out what was actually going on, I did have fun with the job and mostly had a positive experience. Ultimately, things went sour a few months later just because the money wasn’t reliable enough. I’d make a ton of cash one week, but then make almost nothing for the next three weeks and still wind up broke. Plus I was still working a normal job during the day (2 PM-6 PM 5x/week) and then going to the agency and being there from 9 PM to 3 AM two or three times a week. It was pretty exhausting both physically and emotionally.

Personally for me it was mostly a lot of handjobs in cars. I wasn’t interested in providing oral because I wasn’t going to do it unprotected and I hate the taste of latex too damn much. A couple guys wanted to go down on me, but I always refused just for personal reasons.

A lot of the other girls regularly handed out BJs, let dudes eat them out, and did full service, but I mostly tiptoed around that stuff. I did full service just a few times, for guys I really liked and/or who were willing to really pay out for some time and effort. I also took on a few clients who were into being dominated and did full service there if you count pegging, which a lot of the other girls wouldn’t do, so that sort of became my niche.

But it took a good month of me talking to other girls and even watching them work (with clients who would hire 2 or 3 of us at once) to really understand that no matter what the agency owner claimed the rules were, we were expected to fuck for money.

9. I Hadn’t Eaten In Nearly A Week

I was living across the country from anyone I knew. I needed to make some cash, so I turned to the oldest profession. My first day involved getting driven out into the suburbs of a affluent desert town. A guy who owned a limo company paid me $200 to spank me while nude and walk me on a dog leash around a hotel room.

I hadn’t eaten in almost a week prior, so I went to the grocery store with a friend, got the fixings for stew and a six pack of Guinness. I still to this day don’t feel guilty about it nor do I feel ashamed of anything I did afterwards. I had a full stomach and cash until I found another job.

10. “Hot Damn, I’m Worth Something”

I met the guy in the Internet, went to his house and sucked his dick, he sucked my dick, then we sat around smoking cigarettes and talking for a while, then cuddled and went to bed. He gave me $300. I felt so so so powerful and fucking beautiful. That intoxicating sense of “hot damn, I’m worth something” became addicting. I eventually was running with four regular clients, all except one were just lonely old guys who wanted to get their rocks off and have some company. They treated me well and paid me better; between them I was making about $2500 a month on top of my legit day job. Not a bad deal for a college student.

11. “There’s No Way It’s This Easy”

First time went fine. I was an independent so I did everything myself except drive. Went, hung out for a few hours, etc. When I left all I could think was “there’s no way it’s this easy”. But it was. Most of the time it was fun. Being independent, I only saw people I wanted to see which helped a lot I guess.

12. Not How You’d Think At All

This was a part of my life at one point and I’m not ashamed. I do want to tell my story. It’s definitely not how you would think it would be.

I worked at an agency in the city. Pretty well known and had about 9 or 10 other girls. All very nice and very attractive. I believe just one of them was on drugs but hey, all her. My first day was very busy. I had outcalls all afternoon so I was driving from one part of town to another. A woman ran the company and she was pretty professional about it. I believe she ran the business for about 8 years. Had her own lawyer and everything. Pretty sweet. I was a new girl so every guy I saw was trying to break me in. I’ll be honest, the first day I took so many showers I thought my skin would start peeling. I felt so gross but I made about $700 doing only a couple of calls in a few hours. After I was broken in and got used to everything going on, I was making a comfortable $5000 a week. The money was too easy even with the risk. We always used protection and we were able to decline anyone we didn’t want to see.

I got out of it because it became overwhelming and I got into a relationship with someone I love. Some days I want to go back to making easy money but I sit down and think to myself it isn’t worth the emotional damage that comes with it that you have to cover up and wash off. I am clean. I got tested once I left and am grateful I didn’t catch anything.

Forgot to mention!! The guys range from asshole to really smelly to the business man you never thought you’d see there to someone thinking they know you.

13. I Looked Like A Panda

It’s been a long time since I did ‘massage work’, and I only did it for a few months. I was young, the place was brand new and it was the opening day. I turned up early and only one guy came that day, it was also his first time, which made it a lot easier, we were both pretty nervous but that seemed to comfort him.

We chatted as I showered him, he had kids, I’m pretty sure he had a wife too but maybe divorced, ex-army. He was really nice. We went into one of the rooms and started the massage. It was height of summer and it turned out the windows were broken in the room I was in and because we’d only just opened – no fans. It was alright at first, bit of warmth, but then once we started getting into other stuff we were both getting so hot and sticky.

We finished off and we were both dripping with sweat, it was pretty grim. Luckily we both found it kinda funny and ignored it. He went for another shower and I looked in the mirror, all of my eye make-up had completely run down my face. He basically fucked a panda.

14. MY FIRST DAY WAS MY LAST

I worked as an escort one day, and only one day. The short story is that there’s a reason these people have to pay for sex, and most of the time it’s not because they’re too lazy.

The long story is that I was on grindr “joking” about how I’d hook up with guys only if they could pay for my tuition. After a ton of guys actually started giving me offers for regular things, this one fairly normal looking guy gave me an offer I actually took. He told me he lived 20 minutes away, but somehow it turned out to be almost an hour. It was awhile ago, so I don’t remember exactly how it happened, but I was already a little sketched out because he lived in a fairly remote part of Vermont just across the border from my state. The “neighborhood” didn’t have a paved road, and I was terrified I was going to drive off the road or get stuck because it was winter.

So, already going in I was feeling really uneasy, not even taking into account what I was about to do. The agreement was that I would get $100 guaranteed just for showing up, without having to do anything sexual. So the one settling thing was that I wasn’t committed to doing anything.

I get there, and he’s fairly normal, but definitely a bit weird. I can’t really describe it, but he was almost slightly delusional about things. Despite being quite successful and looking pretty young for his age, he isolated himself and therefore lacked some important grasps on reality.

He had us sit down and watch a movie about a gay Mormon boy, which was terrible, and then he just vented for a little while. He dropped casually that his mom just died, which is sad, but he mentioned that he was about to come into a multimillion dollar inheritance. If this became a regular thing, I could easily have my tuition paid for.

That segued us into his loft bedroom. He smoked, and I told him that’s a no go for kissing, but he went and mouthwashed for multiple minutes. While in the bathroom, he had me pull up porn on his iPad to get us in the mood. He had like 38 tabs of porn open already, and that was like a reality check that this guy is really really not like my generation, which really turned me off. So at this point, I was already scared to go through, but the thought of no student debt was too good.

He comes back in the room smelling like mint and tobacco, but he has a candle in his hand. I lost my virginity to candle light and the whole shebang, so I was thinking this was going to be somewhat comforting. But no, he dropped that he has a slight pain fetish and wanted me to drip the wax on him while he jerked off.

He disrobed, and there was the biggest, thickest, mass of hair I’d ever seen on a man’s pelvis, which concealed a pretty average dick. It was instantly a huge huge turn off that this guy was not hygienic. It was at this point I decided that no amount of money was going to make me hate myself for doing this repeatedly. But I made mistake number one and hadn’t collected the money upfront, so I was stuck here.

For an extra $125 on top of the $100, I reluctantly dripped wax, even though he kept telling me I was doing it wrong and that it was too hot. I reluctantly kissed a horse, or at least that’s what it felt like. I reluctantly got enough pubes stuck in my mouth to make a merkin. And he dropped the ball that he has problems finishing, so I reluctantly jerked him off for like 20 minutes while he tried to find some porn he could finish to.

To be honest, the entire thing creeped me the fuck out, the second I pulled out of his driveway with the $225 in hand, I texted him via grindr that this wasn’t going to happen again. He went from being super sensitive not to scare me away (very unsuccessfully) to bring furious and calling me a slut and leading him on.

I drove home with my dignity in pieces and only $225 to show for it. I have fully respect for people who are able to work in this industry because it is not easy. I consider myself a very tolerant and accepting person, but I could never work with people like this guy ever again. From then on I vowed to only have consensual sex.

15. IRREGULAR FREELANCING

I’m still not really sure what to call myself even to this day, over a year later since I first accepted money for sex. I don’t work for an agency and I don’t ‘work’ everyday. Every so often I will meet up with one of the men I have an ‘arrangement with.’

In total I have only ever met 3 guys for straight up sex (sometimes just oral.) When I say that I mean there was no arrangement or relationship type deal. The first time was with a guy that contacted me through a dating site, it took me a while to actually meet up with him, but eventually I did and I don’t remember feeling upset. I was glad to have the extra money as I wasn’t working at the time. The first guy and second were great, the third was awful and I had to shower for a long time after. That is what I would call prostitution. Eventually at a bar while drunk I found a man in a business suit, he wanted to take me home and somehow we agreed on a price. I saw him for 7 months.

I would call that escorting or having an SD. As sometimes we would just go for dinner or I would come hang out at his house for a few hours. I never stayed the night and very very rarely did we do anything sexual. He would still give me upwards of $300 each time I saw him. I was always on edge and worrying about running into someone I knew while out with him (he was much older, it would look fishy), so it got to the point of going very far out of town or just staying in.

16. Thrilling But Scary

I’ve done it only once. After that, I got sick again and it forced me to stop. (kinda a standard in my life).

Anyway, I placed an add on an escort site, with fees for a variety of things I would do. I had a ton of people lined up, though many bailing. Many others were serious (site required a membership for the clients, so more serious people than you’d have on a free site).

Anyway, my first (and sadly last) day on the job was easy. The guy paid me upfront, as I required. He paid for the things he planned to do + tip. And he didn’t get around to doing most of them. It turned into a very short encounter of like 10-15 minutes and he was all done.

Being respectful, I offered him the money back for the extras we didn’t do, but he was okay with it.

Was easy money. Thrilling to do, but kinda scary.

I am considering trying again in the near future.

17. EMOTIONALLY DRAINING

I was 19 it was 1999. I was a model that would come to you as an escort for one hour at $500. The first call they sent me one was a very nice fellow not that old clean fit. I talked to for about 10 or 15 minutes, realize what was expected of me, and went running back to the car. I couldn’t do it and went directly home and quit. Three weeks went by and I realized doing what was expected of me on those dates would at least put food on my table. The next date went well enough, and I did about another 50 or 60 before I had to quit. Shit became too emotionally draining.

18. My First MILF

I’m a guy… I am 6.4, blonde, blue eyes and (back in the days of 2002) athletic but not overly muscled. I worked in a popular bar, I read a lot of books and talked to a lot of older people about everything. And, I have an identical twin brother. I treated everybody equally and (at least in my own mind) I was not arrogant.

I had a lot of sex.. to the point that I had to tell the 1 to go, because the other (girl) would arrive in about an hour. At one point I had so much sex that I was happy that I had “a night off”.

Anyway…at one moment there was this older women, probably about 45. We talked a bit (treat everybody the same), had a few laughs and eventually she offered me 600 euro’s for the night. I was about 20 y/o, so I had a lot of wishes and not enough money to cover haha so I happily accepted. I was kinda nervous but also very turned on by the idea, and it was my first “milf”. I just did what I do to every other girl, treat her with respect… slowly try dirty little things to see what she likes, talk to her about stuff, laugh, and just fuck in all different ways. (nobody gets their parents to sit down and explain everything, so I bought a 15 dollar “sex-Bible”).

I told her I liked it, and also made clear that I appreciated the money. And, if she had any friends to do the same, I would like to “help” them as well. And they came… some married with guys who wouldn’t touch them anymore, some younger, some older…

But after about 1 year I stopped because I wanted a serious relationship. And that is the goal from there on.

19. My First Evening Was Amazing

I’ve worked as a male escort for a year. My first ‘evening’ was pretty amazing. She was 40 year old black woman married with an older white man. She picked me up at a random location, we smiled to each other in the car and started to talk. I’m doing my job so I need to make sure she feels good about the situation and herself. Give subtle compliments, etc.
Normally we would eat in a fancy restaurant but instead she drove to a hotel, payed a room for 2-3 hours, telling me we could do better things then eating while staring at eachother. (TBH I made her horny in the car).

I didn’t expect it but her body was fucking awesome. No fat, everything was tight except her boobs. They ‘started’ to hang a little, nothing bad, nothing granny. Her ass was firm and almost the perfect roundness.

Now, I know exactly what to do to make a woman horny but I didn’t expect that level. I wanted to go calm, tickle her ears and gentle caress her while going down in a subtle way.

NOPE, not what she wanted. She actually ripped my T-shirt and if I didn’t lose my boxers fast she prolly also would rip that.

The sex was awesome. She actually made ME cum (and I’m trained for delaying orgasms). At the end of the act she was shaking and shivering and we were both sweating.

I was so proud of myself, for weeks.

I saw her 12 times in that year (every month) and I became excited the closer we came to that day.

The other woman were totally different, I was glad she was my first day because I don’t think I would have continued if any other was my first.

There are mental downsides to that work though. I was 23 at that time and hung out with girls of age 18-23. Girls of that age, after you spend time with mature women, aren’t so interesting anymore. They aren’t experienced so they have almost nothing to say. So boring, and sometimes not so sexy.

20. The Worst Part Was Hiding It

My first day was actually my 3rd time going into the agency my friend worked at. She was supposed to see the client that came in but she didn’t line up with his physical preference so she came down and offered him to me. She lent me an outfit and I went upstairs, the agency was in a character two level house. I took the money and brought it down, they helped me count it and gave me some last minute advice, all of the girls were in the kitchen at this point.

I literally nervous sweated and shook my whole way through the call, it was my first time and his so we were both a mess. I’m sure he looked back after some more experience and laughed at how awkward it was. I didn’t know if I would come back but I did, my first three calls were the same and eventually I kind of got more comfortable getting naked with strangers within minutes of meeting.

I have been working now for about 5 years, saving a lot of money and traveling a couple times a year. I recently downsized my living costs so I could save even more and currently moderate on an escort review board which is pretty cool. I help organize information about bad clients and rally the ladies to work together more cohesively, I still work on top of this as well. Now I work in my home City and also tour pretty often, this business has it’s ups and downs but with reference checking and being independent I feel like it’s a lot safer.

Agencies definitely didn’t care who they set me up with, they were in it to make a buck and because of that my safety was often a second consideration. I went Indy after a couple years and loved taking the reins of my business. I learned a lot about marketing, website building, photography and editing, interpersonal skills, intuitively reading people and of course sex ;) It’s changed me a lot, some for the better some change for the worse. It’s difficult believing in true love when I see so many married men, I do hear a lot of what bothers men in their marriages though.

The worst part of my job is hiding it, people are so against sex work and often that alienation makes me feel quite alone. It took me a lot longer to make friends in my new City because I work alone and people would judge me if I opened up. They also changed the laws recently in Canada and made it less safe for sex workers and clients alike, it’s a hard thing to realize that no one cares about your well being because of a false image presented about your entire work. I don’t use drugs, drink socially and save money, I also already went to University but love this job more than what I trained for.

21. NERVOUSNESS THAT WASN’T QUIT FEAR

I had a preliminary face to face interview with a reasonably attractive well made up looking girl a couple of years older than me (about 25, nicely done fake nails, hair extensions, makeup, good figure) who explained how it would work and the expectations in a matter of fact way.

After agreeing when I’d be available, I got a call from the agency operator to book my first client, an incall to their serviced apartment.

It was a normal, nondescript flat, in a residential block, in a non-student area on the edge of the city centre. A white man in his late 30s who called himself Martin (coincidently the name of my first boyfriend, which I felt was a kind of a sign) met me at the door and I let him in. He knew I’d not done this before, as the operator would have told him it was my first time, and I think perhaps they have a list of people who are keen to go with inexperienced girls. He paid and I counted the money. He put me at my ease by making some small talk to get us both feeling comfortable and asking bland questions to get us chatting before kissing and embracing me. The nervousness that wasn’t quite fear and the strangeness of what was happening was arousing for me and I had sex with him that wasn’t unsatisfying or uncomfortable. He joked a little with me before he left to show that the air was clear and the ice was broken, and was generally just a normal pleasant person. I didn’t see him again but I only worked for about 3-4 months.

I actually can’t really remember it clearly now, unlike some of the other men I was with, but it was just a normal but thrilling hour and I felt totally comfortable with doing it again. Only a dozen or so more times in that flat though because the risk of multiple girls using it was too high (that classed it a brothel) so one girl started using it full time and I only did outcalls after that.

I was an undergrad university student in a large UK city and following a breakup with my high school boyfriend I struggled to come to terms with, felt now was the time to find out if I could go through with escorting.

I’d always been attracted to the idea of being paid for sex but coming from a totally normal, sheltered middle class upbringing in the suburbs never really considered it more than an intriguing what if fantasy.

I’d only had 2 boyfriends and a couple of more casual sexual encounters, and had never used sex toys, but had been adventurous and happy to try anal, fuck outside etc. TC mark

Related

More From Thought Catalog

blog comments powered by Disqus