Yes, me again. As I alluded to in my previous post, I had a date yesterday.

I use the word date here pretty loosely because the reality is that I was paid by the guy to be there. That’s right, after a long time, I delved into escorting.

I have discussed this topic with a few people in the past. Sex work, the exchange of money for sex, the explicit objectification, the power dynamic between provider and client, has turned me on for a long time. It’s a multifaceted kink, so I don’t want to go into too much detail here. The main reason I never acted on it beforehand though is because I was apprehensive about putting myself out there. The possibility of being identified and called out, having that “stain” on myself (quotes here because I am not using this word to shame anyone, I am simply referencing the general, negative opinion society has towards sex work).

Side note before I go further. I will NOT be sharing any of the information I’ll be referencing in this post for reasons that should be obvious. Anyone asking me for those are going to be ignored and blocked outright. Also, if you are looking for information about sex work yourself (either as a provider or a client), don’t ask me, I am not a reference, do your own research and be careful.

I’ll also divide the post into multiple sections for ease of reading.

Handling the business

So, for starters, a bit over a week ago I created an account on a few websites using older sexy pictures I had for my Tinder profile as well as taking new, glamour selfies in lingerie and taking inspiration from other postings to describe myself and my offerings. The whole thing reeks of amateurism at best and looks like a scam at worst, but I did with what I had in hand.

I then waited for the messages to come. I didn’t receive a whole lot of them, and I decided to focus my efforts on those that were the most promising, meaning the ones that were polite and business oriented. As exciting as it was to think that I was dealing with selling myself, I tried to remain as grounded as possible towards what I was doing. To that end, I tried to rapidly veer any discussion towards business talk, what/when/where/$$$.

Long story short, I booked a single appointment. I didn’t want to take on too much too fast, so as soon as I got one, I locked that in. The deal was $600 for a two hour meet divided into a dinner date and the remaining time spent in private at a hotel of my choosing.

I asked him to pay half in advance, he accepted, and with that, I booked a hotel room not far from the restaurant we were supposed to meet.

The initial meet

I arrived at the restaurant before he did, and using his name for the reservation, went and got seated to wait for him. The place is nice, but otherwise ordinary and casual for a date setting.

For this, I dressed with a sexy (but not slutty or that revealing for that matter) black dress, with my hair up in a ponytail, lingerie underneath and light makeup. Nothing out of the ordinary for a date.

As I waited for him, I won’t lie and admit that I was a bit nervous because I felt a certain pressure to please, to actually give that man a good time overall despite not knowing what to expect from him. However, I was also excited as I had this feeling that the staff and other patrons knew my reason for being there, like I had this “escort” (to use a non pejorative word) target painted on me.

He arrived a short while later. I recognized him from afar from the pictures I had seen of him. He is an almost 50 years old, lanky man with a bit of a gut and short salt and pepper hair. He was sporting the classic polo and jeans combo.

He made his way to our table, and with a charming smile introduced himself. I did the same on my end and the date began. He was very talkative, which I think made things easy for me on that front. He mostly talked about his job, some politics and a bit about his family. For my part, I participated without revealing anything about my real job or any personal information, which was hard at times. All in all, I think it went well and the dinner lasted for a bit less than an hour, as expected.

He paid for us and we left for the hotel. Because we were seated face to face in the restaurant, he couldn’t really be handsy. There was light flirting, compliments and glances, but it was PG. Getting to the car and once inside though, he started to take some liberties concerning the goods; hand on lower back, a kiss before getting in the car, resting his hand on my thigh during the drive, but again, nothing outright sexual.

The follow up

We arrived at the hotel and made our way to the room I had booked. It might be worth noting that I had checked in earlier in the day with some change of clothes and stuff to actually stay the night (without him, he was to leave as soon as his time was up).

I talked in the previous section about how I felt exposed when I was at the restaurant. That feeling actually began when I first walked through the hotel lobby decked out for the date. It was even worse walking back in with a man twice my age in tow. That receptionist, who was there the whole time, knew everything. I am sure of it.

The elevator ride was similar to the car ride. As soon as we got alone, he slowly started to get handsy. He first put his hand on my lower back, as before, but moved down for a quick squeeze of the butt and a cheeky wink before stopping (which I returned, as I really was starting to get turned on by the situation and the anticipation). All in the single minute it took to reach our floor. We finally got inside my room and again, there was some light touching and kissing. He took his phone out and put on some light music before asking me to dance. He laid down, and per his instruction I slowly danced for him. Once in a while, he would tell me to remove/move a piece of clothing. He encouraged me by showering me with compliments. He took his clothes off and started wanking off as I performed. I must admit that it was quite hot, this hits exactly the kind of exhibitionism I am into.

As I had only my panties left on me, swaying my hips side to side and massaging my boobs, he asked me to suck his cock. I proceeded to kneel on the side of bed in between his legs, and executed his wish. I took this man’s smallish cock into my hand and mouth, licked his shaft from bottom to top and even tried to deepthroat him. Gauging his enjoyment from his moans, I continued until he told me he was about to cum, and further until he did in my mouth.

There was then an intermission of maybe ten minutes. We mostly talked about our respective sexual lives. How he hires escorts every month or two since his divorce. I talked about some of my tamer adventures, and “revealed” that it was my first time escorting. The quotes here are because he had a pretty good sense that it was the case. He said it was actually a turn on for him to “break in a new girl”.

Towards the end of that conversation, I saw that he was hard once again. He made a joke about it being the time for the main event. He put on his condom while instructing me to remove my panties and to present myself in doggy. He first used his finger to touch me and explore my pussy before moving in to kiss it and eat me out just a bit, commenting on the view and taste. He then moved behind me and slowly entered himself into me.

What followed was what I would consider textbook sex. He fucked me from behind for a bit, grabbing at my hips and tits before wanting to switch positions. I then took the lead by riding him, then missionary, and so on and so forth. At some point I came from touching myself as he was thrusting into me. Soon after he filled his condom with a deep grunt.

We had another pillow talk. Talking about the sex we just had, comparing it to other experiences. A few minutes later he took a shower and left soon after, paying me the rest of my due.

Closing thoughts

At some point during the event, the setup and context kinda gets lost in the moment, so the sex itself feels just like that, sex. I was not thinking about the cash he had sent me beforehand, nor the cash he was supposed to give me afterward. With him, it really was just like having sex with another random hook up, with the difference that it was in a hotel room and he was twice my age (which I rarely do).

With that being said, thinking back on it and writing this, it really turns me on to think that I sold myself to him. To think that he chose me for the sole purpose of getting off and that I made it happen is hot to think about. I am going to say it, I feel like a whore, and it’s a good feeling.

For those curious, because I know you are, between the hotel and other expenses, I brought home a bit over $400. And no, I don’t know what I will do with it.