26 Escorts Reveal What Their First Day At “Work” Was Like

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 $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 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 $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.

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 WW2 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 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.”

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.

5. He 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 modeling 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 jerking 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 blowjob 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.


6. Horrible first time

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.

7. Short on money

I started working because I’d gotten a few propositions through a dating website. I was studying med at the time and I was short on money. So one time, this guy made me what seemed like a lucrative offer and I agreed.

I didn’t know how any of it worked, so I told a friend I was going out and to call or text me in an hour’s time. We initially met in a park at night, sat in his very, very nice car, had a bit of a flirty chat, then made an appointment. He said he was 58 years old, but I think he was about 15-20 years older than that.

A week or two later, I drove over to his apartment. I was petrified, but I needed the money so I rang the doorbell. It was a lovely apartment, and he paid upfront. He was nice enough. He asked me to do some things that I didn’t want to do, so I said, “Maybe not this time.” Kept an eye on the time (via the helpful clock radio next to the bed) and thankfully he finished on time. Had a shower, bit of a chat afterwards, and then he kissed me goodbye on the cheek.

I think the fact that I said no to rimming annoyed him a little, but he texted later and asked if I would like to do a threesome with another working girl. Things proceeded from there.

8. The business was booming in 2011-12

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.

9. Two clients on her first day

Yes I was nervous, but it wasn’t really awkward. I had two clients that day.

I can’t even explain the feeling of my heart in my throat on the way to my first job. I thought my heart was going to burst out of my chest. But it ended up very well.

The first guy was really nice. Mid 30’s, extremely average looking. It was somewhat… boring. 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. Along with the occasional gift of art or books.

And 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.

I still escort from time to time. It’s great money and a lot of the time, it’s just lonely older men. My agency is very safe, my clients don’t have my personal number (unless I give it to them) and they make me check in with them before I go in and again when I’m done.) Don’t get me wrong, I get some strange requests, but for the most part it’s just sex. I love sex, it hasn’t discouraged me in any way shape or form.

10. He had a curved penis

My first time professionally was with an awkward Indian engineering student who paid me $500 to drive out to his apartment and do a two hour session with him.

Oh my gosh, I was so incredibly nervous the whole way, didn’t really know what I was doing, but once I got there, I pretty much went with the flow, chatted him up, started playing with him, and we had really epic conversation and he’s still responsible for one of my top ten orgasms (perfect little 4″ curved penis, hit my g spot with every thrust). Fucked twice, I gave him a blowjob while he was on the phone talking with people he was working with. I’m fairly certain he thoroughly enjoyed himself.

Immediately afterwards, on the drive back, I was just so utterly dumbfounded that I got paid that much to fuck a guy that was theoretically dating material if he had the time to date. It was tremendously encouraging, and I have those sorts of experiences with wonderful men (usually around thirty years my senior) sufficiently often that I’m not going to quit escorting until I age out.

11. She felt sick

When I was 18 I was tight on cash and decided, fuck it. I need a sugar daddy. I went on craigslist and found a guy. He wanted to meet me first and needed a new girl to replace his old one, he was willing to pay 4 figures per date. I drove to meet him and was stuck in traffic on the way for an hour or two. I sat at a Starbucks for a while waiting, he got lost because he was only there on a business trip. I was shaking by the time he came. We got burgers and drinks and sat at a table waiting for everything, talking. He was sweet but not my type, I was so nervous and shaking. We got to his hotel and sat and talked and ate, then started getting frisky. He would not stop talking about how amazing I looked and was and I know he was trying to flatter me but after a while it got really old. I stayed the night and left in the morning. He gave me money for gas. I later told him I’m sorry but the age difference felt too weird and he would have to find another girl, but really I just couldn’t stand him.

Then I found this married guy. We talked, I sent him pictures of myself and he was hooked. He ordered things off of Amazon for me to bring (we’re talking bondage/anal stuff) Anal was on the list of “necessities” to him. I was an anal virgin and reaaallly hesitant about it. I told him I wanted to be blindfolded for the thrill of it, but really, I just didn’t want to see his face. Drove an hour to a motel in his town to see him. The way everyone looked at me, I knew they knew what I was there for. I knocked on the door, it opened. I stepped inside where the lights were off, kept my eyes to the ground. He came up to me and started stroking my arms, my face. He instructed me to put the blindfold on and I did.

I hated it. I hated every minute of it. I lost my anal virginity to him and it was painful and I cried. I could feel his fat slapping against my stomach, he kissed me with his bushy beard tickling my face and I fucking hated it, I wanted to vomit. He gave me the $400 and I left. I cried all the way home.

He was nuts about me, wanted to take me on trips and buy me an apartment in his town and all that. I agreed to meet him again, but no anal and no kissing. I told him it felt weird to kiss him when he had a wife (I know, what a fucking lame excuse but what was I supposed to say, “you disgust me”?).

The second time he was coked out and had a hard time keeping it up. I had to awkwardly console him while he beat himself up over it, and suck his flaccid dick several times. We laid together for a while and we had a bit of “sex” (without a full boner it’s pretty much a fail). Once he gave up on the whole thing and admitted defeat, I packed everything up and sat at the edge of the bed. He brought my money and placed it in my hands, and told me to look at him. I was still wearing the blindfold and I shook my head. He took it off of me and told me to look at him. He was wearing a bandana that covered most of his face except his eyes. He had lovely eyes, and it made me want to cry when I thought of his wife.

This dude was convinced that I wasn’t in it for the money. I had a sick mind, I had a dirty side, and only he could fulfill it. I didn’t bother correcting him because I didn’t want to kill the self esteem he was building for himself.

I told him I couldn’t do it anymore. He messaged me a few times over the next year but I kept telling him no, no matter what price he gave me.

I regret both encounters to this day and nobody knows about it.


12. He threw cash at her

When I was 18 I was looking for a sugar daddy when the CMO of a very well known company (he didn’t tell me this, I screened him and the reverse image search brought heaps of Forbes articles on him) offered me $1000 for the hour if I came to his hotel room. I hadn’t considered transactional sex for money before but I was interested with the price so I showed up, got my money in about three minutes and went home with an uncontrollably large smile on my face.

I wasn’t nervous and I didn’t feel guilty but then again I’ve never been sexually repressed and did plenty of research beforehand. The only awkward part of the night was when he finished rather quickly and then, I’m assuming from embarrassment, threw the cash at the door and asked me to leave.

I’ve been doing it ever since (15 months now) and it’s been such a positive experience I’ve begun seriously considering taking a sabbatical from university and pursuing sex work full time.

13. Not what she had envisioned

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!”

14. Sad encounters

Gay man here.

I remember the first time I accepted money for sex. A guy messaged me on a gay dating site. I was 17 at the time, “18” on my profile. This man (60-something years old) offered me $100 to suck my dick. I knew I was down immediately.

I countered back that I’d do it for $150, and he had to let me watch porn while he did it. “Can I swallow it?” Uh yeah, duh.

So I went to his place. As a (28 year old) adult now, I think – what the fuck… that guy could have murdered me. He could have raped me. He could have cut my skin off to wear it like a dress.

But he didn’t do any of those things. He put on some porn for me (very helpful, as I wasn’t attracted to him at all). I pulled out my dick, started jacking off, and once I was hard he sucked me to completion.

$150. Thank you very much. “Would you be willing to come again some time?” Uh yeah, duh.

So I would head over to his place about once a month. Cum. Get paid. Repeat.

When I moved away for college I found similar guys. Old men. Fat men. Especially ugly men.

I never had to make them cum. They just wanted to make me cum. So that’s what I sold them – a chance to make a hot young guy with a big dick cum. (forgive the vulgarity). It was all about letting these guys fantasize that they had gotten me without paying for me. I learned quickly that they were happier if I could make them feel like it wasn’t an exchange.

My favorite/fondest memory though was one guy who didn’t even want that. He wanted someone to cuddle with, rub against. We stayed in our underwear. I actually sort of felt good about visiting him because it didn’t feel as gross.

He just wanted human contact. And I gave that to him. For a price, but I gave it to him.

15. Happy ending?

2003, I am an exceptionally naive 22 year old with six figure debt from a failed marriage and a baby to support on my own. A year before I had been approached by a friend of my sister who offered me a job as an escort. A had no idea what an escort did but the offer of $150 an hour remained in my mind and I called the guy when I reached as low as I was willing to go. I thought escorts danced or masturbated, I wasn’t even a good dancer. I have no idea what I was thinking.

Looking back, my first appointment was a disaster. John was exceptionally patient but I was so anxious. We had a drink, smoked a bowl, and he offered me some coke. Never have done coke before, I hoped it would help my nerves and obliged myself to his offer. That obviously didn’t work. Another hour of chatter and he asked me what I could do, sensing I wasn’t exactly on firm footing with the current endeavor. I had brought a bag of lingerie and offered to model it for him. Somehow this was sufficient for him and the drive home later was to this day one of the most fun drives I have ever had.

Of all the things in life I am thankful for, few rate higher than my dislike of coke. Instead of getting sucked into all that, I got myself out of debt, bought a house and went back to school. Graduated two weeks ago debt free with one of the most sought after degrees from a prestigious school. I have been working independently since 2005 and currently work one $1500 session a week (all my clients I have had more than five years). It has been a lifestyle that has served me well, I have met amazing people and had unforgettable experiences that would otherwise been impossible. Retiring is one of the harder things I have to do but in three months I hang up my heels and am walking away.

I still see John, of course I fuck him now. It only took about four appointments and a huge blow up with a client with more realistic expectations for his $250 an hour to figure out what I was supposed to be doing, then I learned how to do it really well. I have spent a third of my life as a prostitute but I have a beautiful home with big diploma on the wall, happy kid, multiple vehicles in my garage, and the world an open possibility. I am a very lucky lady.

16. Weirded out

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 50 (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.

17. Degree with no money, left to own device

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 blew 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.

18. Very nervous, so much that she almost turned around on the drive over

It all happened over Thanksgiving break my freshman year (college). I had heard a website for sugar baby a/daddy’s and decided to try it out. After weeding through all of the messages I got, I found a guy that was actually attractive and had chemistry with. So we decide to meet up at his place.

The drive over I almost turned around 5 times, I was so nervous. I know on his door and he looks mostly like his pics, just a little older and shorter than I was led to believe haha. Its both of our first times so we have no idea what to do. We sit on the couch, talk and put on a movie.

Afterwards we go to the bedroom and fool around and do everything but sex (I was too nervous). It was great and I spent the night. He ended up paying for my rent ($670) and a new phone ($500). All-in-all, he was a super nice guy but ended up getting too attached :/ I’ve continued to be a sugar baby and make awesome money from it with the added bonus of only sleeping with guys that I’m attracted to 🙂


19. Deepest and darkest fantasies

I was 35. I’m fit, tall, long brown hair and eyes that shift from blue to green, in good shape from bicycling. I have a Ph.D. in linguistics and a master’s in literature, and I’m male.

I was “in-between employment” and talking in a philosophy-oriented discussion forum on the Internet with some friends I had made there. I had discussed, at length, the importance of Jung’s notion of the Shadow in proto-Indo-European myth cycles, and was privately messaged by a woman who had not taken part in the discussion, but had followed it with interest.

She is a practicing Freudian psychoanalyst, in a large American city, and we discussed the tensions between Freud’s and Jung’s approaches, and the nature of the Shadow and integration. We began discussing sexual proclivities, then of course it turned to our own, we shared several compatibilities, and she confessed that she wanted to explore some kinky fantasies she had, and wondered if I would write her some erotic fiction on a number of themes. I agreed, and she enjoyed them immensely.

We talked more in-depth over the course of a month, had chatsex, swapped pictures, and so forth. A month after we first talked, she offered to fly me to her, put me up in a hotel for two weeks, and pay me a sum of money to act out her fantasies with her.

I considered it. She insisted on it being a business arrangement, so that she wouldn’t “catch feelings” (in not such exact terms) and because of the rather intense nature of her fantasies – “buying a sex slave” was part of them. I finally agreed.

Two weeks of the utter legal limits of debauchery (aside from the fact of the exchange of money for companionship and services) ensued. Sex while reciting poetry, sex while drunk, sex in public, sex at a private party with an audience, domination, submission, role-play, on the roof of a high-rise in a thunderstorm half-expecting to die of a lightning strike. Waking up tired, sore, bruised, and mildly dehydrated was the norm. I tied her up, suspended her in a web of ropes, and thrummed them with a cello bow until she orgasmed from the sensation and the verbal accompaniment. She placed a rather vicious dog’s choke collar on me, chained me, and proceeded to entice and humiliate and tease me for hours – until I was slavering and manic to ravish her, and only then she tugged open the knot securing me from acting on my impulses. Far darker things we did.

Over time, we met for sex a few more instances – but we inevitably had developed feelings for each other, and so discontinued the business end of the arrangement. I had used the money to start a business, and gave her back every penny she had given me, and we agreed that we’d finally consider it an interest-free loan. Some of what I wrote for her and that we wrote together has since been published under a pen name, with a little commercial success.

She considers me her last hurrah – she went through menopause shortly after our last sexual visit together, and now doesn’t have the same sexual drive.

I have never involved money in a sexual relationship before or since, and honestly, none of the other relationships I’ve had compare in intensity or raw honesty with the experience we spent together. We stripped each other’s souls bare and bleeding, and know one another more intimately than anyone else knows us.

20. Was offered $900 for a night

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.

21. No sex, just talk

When I was 20 I used to troll around on Grindr for guys, and one day this guy messages me to hook up. He seemed to be the older type and I was interested so we met at a Starbucks to see if we liked each other. He turned out to be a fairly fit man in his late 40’s that was still quite handsome.

We chatted each other up and he was really nervous, and admitted it was his first time. We eventually went out to dinner and went back to my place where we had sex. I was letting him sleep over but he suddenly had urgent business at 3am in the morning so he left. When I woke up I found that he had left 300 dollars on my desk.

Honestly at first I wasn’t happy because I’m not a whore and I didn’t need the money but I figured what the hell and got over it. He texts me a week later and wants to get back with me and I wasn’t dating anyone at the time so I agreed.

We did the same thing where we went to see a movie instead and went back to my place where instead of having sex he just wanted to cuddle me and talk about his job. So I sat through 3 hours of him bitching about his life before he had to go and again I found 300 dollars in my desk.

This continued for a good 4-5 weeks of the same thing where we didn’t have sex and he just wanted to cuddle me and talk, and where afterwards he left me money. I found out he was the directing manager or whatever of a company and he had a wife and kids and didn’t want them to know so he’d say he was out drinking with his friends.

One week he stopped texting me and I didn’t bother texting him so that was that. I think he was a closeted guy that just wanted male contact and it was quite sad but just one of those things

22. Very odd first time

I was very nervous my first time. Even though, at that point, I had had several hookups and play sessions with men I had met off craigslist or Fetlife, it was still weird transitioning to paid work and being afraid I was walking into a police sting.

It was awkward at first, just because the guy seemed nervous too, but it went pretty smooth once we both relaxed a little. The most awkward thing was handling the money, because I wasn’t sure how to do that. He gave it to me up front and I wasn’t sure what to do, so I excused myself to the restroom, freshened up, and counted it, which is still my MO.

My client was very happy, and ended up giving me an additional tip and leaving me a positive review on the site he had found me through, which helped to start my career out and get me more dates.

I was a little surprised at that because I thought it went OK but was awkward. He was a bit older, and someone who was pretty recognizable in the community, which might have explained his nervousness. 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.

Now, part of me wonders why I kept it up, because it really was odd now that I look back on it. I think if I hadn’t had better experiences when I was hooking up for free that I would probably have stopped right then because of the wierdness. OTOH, it was easy money for doing something I was doing anyway. The next few experiences were better and more encouraging, and most of the time it’s fairly enjoyable compared to some of the other jobs I’ve held.

23. Adult Friend Finder

At 20, I was on AFF when I was offered 2,000 dollars for two hours of my time and a few snaps with his cock inside me. He was a 65 year old man. The sex was pretty good for being twenty, and I got off on the notion that he was paying to fuck me. Honestly, holding the money in my hand afterwards turned me on much that I masturbated the second I got home with the envelope in my hand.

I did escorting for three years before an ex ruined my reputation. I loved it. Sure, some guys were dicks, but I was making anywhere from 250-400 for like twenty minutes of work. Now, I can talk to just about anyone without reservation.

24. Started as a dancer

I’m a former escort. My first day was easy because I started off as a dancer. I used to work bachelor type parties. The guys would ask for more. Eventually I just agreed to more. My cousin and her friend did parties like “reverse bachelor parties.” Basically a guy getting divorced so like 2-4 of his buddies would hire us to go out and dance. Almost always in a private residence. I would say like 90 percent of the parties the men were over 45. So we would go and dance and hang out. Then at the end either my cousin or her friend would go with the “bachelor” into a bedroom.

When I first went along it was because my cousin got sick and she asked me to go with her friend. She explained I would have to just go, flirt, sit on a few laps. I could dress as sexy as I wanted. So I did that. I wore shorts and a tank top. I looked cute but didn’t really fit the look. I turned out to have fun.

I ended up topless and basically got paid to sit around, joke and flirt with a bunch of men. I really love attention so worked out well. We were there like 2 hours and I got $150. After that they used me as a substitute more often or if the group was larger. I got a bit more crazy with my outfits.

When you’re in that environment it’s fun. People were laughing, drinking. Passed around joints (etc.) it was just fun. My outfits got more daring and I started to REALLY enjoy the feeling I got. I sat on a ton of laps and basically would feel boners. I would laugh and joke. Men treat you differently. The same man who would be embarrassed if you caught him looking at your tits at the super market had no problems looking when you are there to party. After a few months (7-8)of doing this I felt like the next step was no biggie. I would get like 120-160 for just hanging out but the girl who went with the bachelor for more.

When I would go to parties the other girl would just tell the guys right away that she would be the girl for the bachelor. After I felt ready, we gave the option. I’m smaller/petite. My cousin was curvier with booty and boobs. Her friend is curvy too but Asian. The first time I got picked I pretty much just gave him a naked lap dance and stuff progressed. Afterwards I felt super sexy and empowered. I would do like 1 or 2 parties a month. Who ever got picked would go in the bedroom. The other girl would just hang out and flirt. We would also give out info for 1 on 1 meetings.

I never had to use websites or walk the street. That lead to more traditional meetings. I never had any creeps. Every guy I met was a guy I had laughed and joked with before so made it easier. We all normally played safe but I let a few regulars do different stuff. Anal or unprotected. I am a sexual person so I tended to have fun. I didn’t orgasm Every time but I did a lot.

Many of the men I met with 1-on-1 were married over 45. The only down side for me was making an appointment a few days in advance and just not being into it the night of the meeting. Since many were married they would plan a night when their wife was busy or whatever. Some nights I wasn’t into it and had to fake it. Boo hoo right? I did like 1 or 2 parties a month and met 1-3 guys for 1 on 1 meetings a month. It wasn’t full time, I just did it to supplement my income.

I made around an extra 1200 a month. It was fun. I stopped around a year ago because I met a guy in my “normal” life. We dated a while and I got serious. By then I also got a better “normal job” and was making a lot better than minimum wage. After I quit I still met a few of my regulars for a bit. I love my bf and my current life but occasionally I still miss the old life. The excitement. My bf treats me well. Tells me I’m beautiful. But not the same as the other men looked at me.

25. She felt gross

I don’t remember my first day as much as my very first client. 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.

26. From the other side of the looking glass

This is from the other end of things. I’m in my early ’50’s, fairly wealthy, and I hire a specific escort 1-2 times a month to play my girlfriend at social/business events. I do it for one very specific reason: to see the mixture of jealousy/hatred in the eyes of my associates when I walk in with her on my arm. Since I’m not interested in cultivating an actual relationship with someone less than half my age, I find this to be an excellent way to really piss off the people (both men and women) I socialize/do business with, without looking like I’m actively trying to piss them off. Petty, I know, but sweetly satisfying nevertheless. All the men want to bang her, and all of the women want to kill her in some gruesome fashion, especially the older ones.

We’ve never had sex. Although I was practically insatiable when I was younger, these days the only reliable of way of doing the deed requires the assistance of little blue pills, and I find I’m just not terribly interested anymore. It still surprises me at times, but I have to say I’m considerably more clear-headed now than I was even ten years ago. A fair trade-off, all in all.

For those who’re wondering, the girl looks somewhat like a taller, much more physically fit Inara from Firefly. She’s a med student (many escorts are college girls who’re in need of cash, according to her), works for an agency, and I pay $500 for her time, plus extra if there’s sex (negotiated outside of the agency). We don’t have sex but I pay her an additional $500 anyway to make it worth her while, more if we go out of town. She plays the role of devoted girlfriend very well and seems to enjoy the effect she has at the gatherings I take her to almost as much as I do.

The fact that she’s not only beautiful but highly intelligent just makes the folks at these events hate me all the more.

If things end early we’ll sometimes go back to my place and watch bad horror movies, which we both love. We do our own Mystery Science Theater routine, shouting at the screen (e.g., “don’t go down into the basement!”) and throwing popcorn at the idiots getting hacked up by the killer clown or whatever. It’s a kick.

She doesn’t talk about her other clients, but from what I gather I’m the only one she doesn’t do something sexual with. I gather I’m sort of a “paid night off” deal, where she gets to play a role while circulating with the rich and sometimes famous without having to get sweaty at the end of it.

I have to say, I’ve had more fun with this girl, an escort, than most of my ex’s. It’ll be a sad day for me when she becomes an MD and moves out of escort work. I’ll be happy for her, of course, but I’ll miss the stir we cause when we go out together.