A Day as an Escort

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You might be curious how a day as an escort looks like, or what experiences are escorts and clients going through. These are 10 real stories reported picked up at Reddit.

Beginner’s Luck

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.

From Crying to Fun

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.

The “Generous” Gentleman

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.

The Next Dating Site

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.

Safe and Fun

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.

Pleasant Surprise

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.

This is Not For Me

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.

Pretty Good For an Hour

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.

An Odd First Experience

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.

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