You know when you first see or experience something and it, for better or worse, changes your view or perspective on something forever? An amazing meal, a new sensation, that first white hair, an unexpected confession from someone you respect, a fart you trusted but knew you couldn’t. You get my drift. For me it was when I went down the rabbit hole looking for a casual encounter on Craigslist. I am largely ignorant of many things, being the focused shut-in that I am, so I had no idea that Craiglist had an “adult services” tab. That fateful click has lead me to spending, or wasting depending how I saw it at the time, on risky, adrenaline fueled meetings with women of different walks of life and has, in no way, helped my mental wellbeing.
There is a lot to learn about “the hobby,” as it is called, and you can learn a lot about it online pretty easily with a few quick searches. Depending on what you find, you may not read about the times you might be in a house that is largely unfurnished and be sitting on a mattress without sheets. Or the extravagant hotel room you couldn’t afford (but could afford some of its occupant’s time). Or the fact this seemingly young, pretty, nice girl just asked if it was okay to remove her teeth first because they were hurting. Or the other simple signs of drug abuse. Call me stupid, because I was definitely naive. I thought I knew what to expect, but I never knew what I was getting into until I was there and I had a lot of learning to do since I was so sheltered early in life.
The number in the ad was attached to someone with a goal or purpose and it is just that. An advertisement that maybe false or tell you exactly what you are getting, either for better or worse. My first time I took my time to find someone who was not out of my league. Her photos seemed good, although a little staged. She had blond hair down to her shoulders. She was overweight, but not overly so. She was smiling, which can go a long way sometimes.
I text the number and get short, misspelled responses. How much is the donation, when do you want to meet, where are you staying, etc. I get in my car and I’m a nervous wreck. To this day, I have only ever felt the level of anxiety, unsurety, arousal, and adrenaline that I get when I was about to see an escort. I think that it was due to the sheer volume of hormones that would cause me my whole body to shake and shiver as I made that short drive to meet the lady of the night.
First, the donation. Pretty much any old gas station would do as a quick pit stop. I would often get something to drink or some kind of candy after hitting the ATM, but I dropped the pretense after awhile. Gotta be frugal. Once at the hotel, I text the number again letting them know that I arrived. I waited only a few minutes before I received a three digit number before making my way to the second floor of the notel and knocking lightly on her door. The door opened and I didn’t see anyone, but I slowly stepped in and turned to look at her aaaaaannnd it was a her, which is great since sometimes it isn’t. She had short blond hair held back with a barrette or some other hair device I don’t know the name for. She was overweight, but not overly so. She wasn’t smiling.
However, it was not the woman in the photos. After a time I got better at spotting photos reused by many people, whether stolen from instagram, crappy “girl next door” porn ads from 2001 or from pornstars. She wasn’t ugly, so that was a plus. Look. I am there for very shallow reasons, but looks aren’t always the most important. You don’t want a car crash and you don’t want it to work against you while you are getting it on. You can’t ask them, even jokingly, to put a paper bag on because they are people too dammit. Sometimes they are horrible people, but how about some mutual respect (and caution) before you throw insults?
Anywhosit, she was average in many respects, but she was nice when I first walked in. The room stank strongly of weed. I don’t partake and I hate smoking in general, so it was a bit of a turn off for me. The place wasn’t trashed though, which is a bonus. Some rooms can be covered in clothes, or takeout boxes. Sometimes it is leftover food, cigarette ashes, and needles. I lucked out this time.
We talked very briefly, I placed the donation on the side-table, and we got undressed in silence. I laid down and she rubbed my semi-flacid penis to full-mast before slipping on a condom. She began sucking my covered cock very slowly and very poorly. Thankfully, I had the condom on so I didn’t get scratches from her teeth. After a little longer to make sure I was good and hard she flipped over as I got behind her on the squeaky spring mattress. I wasn’t a virgin, but the amount of fumbling trying to get into her hole was rather embarrassing, but I eventually found her warm and moist pussy. I thrust into her from behind slowly for a minute before picking up the pace as she was beginning to breathe heavier and just starting to moan. Her ass jiggled like nothing I had experienced up until that point in my life and has instilled an appreciation in larger women since that day.
I was marveling at how physics was causing interesting waves of flesh from our bodies colliding as I felt that familiar surge of pleasure and I knew I didn’t have long. I began to thrust harder into her, grabbing her lovely, soft, jiggly ass more firmly, as I was getting closer before she said what every man wants to hear during sex. “Can you slow down a little, it’s starting to hurt some.” Well, sure, okay. I slowed down and lost some of the arousal before taking long slow strokes that brought it back. Six more pumps and I came in her pussy (in the condom of course) before slowly stopping due to sensitivity. I’m not very vocal (see lack of dialogue above) so it often leads to confused women below me when I cum and am slowing down or stop altogether. My wife understands, but it is something I’m working on. You learn a lot of good tips from stories on this subreddit. This lady was also confused.
I let her know I came and asked where I could throw the condom (ends up being the toilet, in many cases. Sorry hotels). She just laid down and I sat next to her, quietly, awkwardly, before we began to talk for a few minutes. “Was that your first time?” Me being dense, thought she meant seeing an escort. “Yeah, it was. That obvious?” “Yeah, just a little” and she gives a light giggle. She mentions she is 22, 2 years younger than her ad, and she said “Do you believe everything you hear in ads?” which I should have taken to heart more before learning the hard way later. I said thank you and goodbye and went to my car. I sat in it for a second thinking about what had happened, trying to take in the positives more than the negatives and figure out how to do this again, but better next time. Sometimes it can be better, but more often the little head prevails and it gets its way, but I suffer the consequences. I drove home, took a shower and started looking at the “adult services” some more before passing out that night.
This was the first of many women I would meet in my foray into “the hobby” and it slowly sunk its insidious hooks into me. It has been a taboo and risky past-time that has made it all the more exciting for someone without other vices. The longer time went between seeing an escort, the greater the desire increased for the next time, leading to potentially less vetting and faster action.
Source: reddit.com/r/gonewildstories/comments/ljofk9/mf_22_my_first_escort_experience