That Time I Convinced My Ex I Was A Prostitute [F/M]

Big ups to /u/wilson48 for not only convincing me to share this story, but also editing it thoroughly for me. If you haven’t read his stories, they’re awesome, though he could stand to share some more ;)

This story is an oldie but a goodie, taking place a couple years ago. I had a boyfriend at university, (I’ll call him “Logan”) we started dating as Freshman, and broke up at the start of our senior year. To keep it simple, he was a sweet guy, but our post-university plans weren’t lining up and the fire was pretty much gone. A week after we broke up, he was far from over it, but we were instantly friends again – we’re friends to this day even.

Fast forward a few months after our breakup, Logan and I ran in similar crowds, so him and I are hanging out at a low key birthday party for one of our shared friends. It’s a great night, and Logan and I are still hitting it off well as entirely platonic friends. At one point in the night, one of our friends brings up this one insufferable guy from a class most of us had together, and how there was a rumor going around that he had hired some sort of Craigslist hooker.

Prostitution, and the art of marketing to the XXXXL customer.

During my time as a prostitute (I don’t like the term escort for various reason), the agency I worked for had a certain number of high value ‘clients’. Many of these clients were loyal to the agency but a few were loyal to specific women, so when those women left the agency, retaining the client was something that could be difficult. However the agency always very focused on having a small client base, always went to extreme lengths go get them back.

Freebie’s are not usually a big marketing tool for most escort agencies. However if the agency knew a client had the capability to pay, then they’d sometimes consider it.

The departure of one particular girl from the agency left several regulars to be hoovered up by the other girls. One man however wasn’t for hoovering, let’s call him Harry and he was a league by himself.

As a prostitute you learn early on, how to handle the morbidly obese, and Harry was almost into disability territory he was so fat. I’d first met him about 3 months previously, when he’d booked a threesome with his regular girl and me.

To cam or not to cam [sex] [webcam]

Before you make your judgments, know that I never intended to find myself here. It's a big secret, what you're about to read about. It's a dirty secret. Embarrassing secret. Shameful secret. I have a BA in Anthropology, and am a passionate people-watcher. I don't judge, because it takes all kinds to make the world go around.

Humans are sexual beings, curious and sexual. How else would our species have succeeded? It is in our genetic code to spread our gene pool as much as possible in our lifetime. Whether we like to admit it or not, humans are not monogamous creatures. We pass ourselves off as such for reasons that society imposes. For that reason, sex sells, and sex will always sell. Prostitution, for example, is the oldest profession in history. With that being said, I am not a prostitute.

For those of you who are perhaps naive about the term "Webcam Model," I can only say that the name of the profession is misleading. A Webcam Model is one who puts on a show (I use this vague term for a reason) for money. Visitors to the website that you are broadcasting on are primarily men. Depending on the website, different tipping or payment systems apply. In short, I appear on a live webcam stream in exchange for money.

Worst prostitute ever! Part III [m/f]

Oral sex can at times be a fairly complicated process, whether it’s a man or woman you’re performing it on. It’s made harder if you were in a situation like I was, where I had a large butt plug sitting rather uncomfortably inside me.

As a prostitute there are a few key points to consider when you’ve got a client’s cock in your mouth. The key one is when to put the condom on him. It was entirely up to me when to put the condom on during oral sex. With my first few clients, I’d always put it on immediately but then quickly discovered that caused all sorts of problems. It was hard to get guys to cum, they’d lose their erection and decide they wanted to fuck you vaginally or anally instead. It was easier just to leave the condom off and either put it on towards the end, or let them finish by masturbating and ejaculating onto me.

The second point was whether to let a guy put his hands on your head to guide you. With some men (not just clients) this could be seen as an invitation to try and jam their cock down my throat. However by letting him guide me, they often ended up finishing a lot faster, and provided I kept both hands on the base of his cock I could usually stop men from getting carried away.

When hiring two prostitutes to have a threesome, there are some points to consider. [MFF]

The absolute key thing to remember is to try and make sure that the prostitutes you hire don't hate each other. There are other factors as well, but that one is pretty key.

Let's call our big spending customer Alex. For the 6 months I'd been working as a prostitute he'd been a regular of mine, for the most of it.

He was a bit weird, and a lot of the other women at the agency didn't like him, but I got on with him pretty well. With me at least he directed a lot of his energies towards role play and light humiliation, rather than the more extreme stuff he often wanted with other women.

He was that key thing, a regular. Someone that would adjust his booking around your timings. He'd book me for two hours twice a month on whatever time was convenient to me, so it spared me having to fight for bookings with the agency.

Let's call my colleague Alice. Straight off Alice called herself an escort rather than prostitute. Despite the fact that like the majority of the women at the agency rarely actually did anything that included the social aspect of escorting with the clients. Rather than a descriptive term, I felt she used it as a kind of euphemism, for how she earned a living.

Worst prostitute ever! Part II [m/f]

As a prostitute you get lots of bad advice from a lot of different people. From how to deal with the customers, to how to handle money. You always needed to consider who it was coming from, whether it was other prostitutes, the agency, drivers or doormen. Women in the business that were very keen to offer advice, I suspected were doing it to mentally reinforce their own decisions.

Some women prided themselves on how they tough they were with the clients, enforcing limits and demanding certain standards of behavior from them. In my experience it never worked, they inevitably struggled to retain clients, they’d fall out with the agency and would end up being strung along without getting the hours they wanted.

Your hours quickly became the focus of your work. The agency in quite a smart way had side-lined the issue of money. Most prostitutes will have a list of services and charges, we didn’t. We all provided the same services, though some more enthusiastically than others. The client paid a flat rate per hour to the agency who in turn paid us, usually again by the hour.

The Extreme Fantasy Business-Part One [FMM,BDSM,Fsub,oral,prost,sadism]

I made sure he could see up my miniskirt while he described his preferences. Most clients that we deal with are either insecure men and you can sense the sex crazed manic in them the moment they walk in. Adrienne was different. He was by all means a complete stud and could probably get any woman he wanted. Not only that but instead of being eager and excited like our usual clientele, Adrienne seemed more frustrated than anything.

“What can we do for you today Adrienne?” asked my boyfriend/boss Ian.

He shuffled nervously. “Uggghh… your flyer said that you guys can um… satisfy the most extreme of fantasies?” His nervousness made him sexy. “It said here that there is limit to what your willing to do to satisfy you..” he stopped talking and awkwardly awaited a response.

“Mr.Panouge” said Ian breaking the silence “Call me A.D.” Adrienne said “A.D. Fantasies Limitless is unique for a call girl service for one simple reason. We. Will do. ANYTHING to ensure our customer is satisfied. You see the girls our company employs have to fit a very specific profile. Every woman in our employment has what we call an “extremist” personality type. They are adrenaline junkies. Not only have the ability to go far beyond the limits of what even the most intense human would say is painful, but the get off on it.”

Worst prostitute ever! [m/f]

He didn't actually use that phrase but he strongly implied it.

Let's call him Kevin. Kevin had been a regular of the escort agency I worked for, long before I arrived and years after I left both the agency and the glamorous world of prostitution, I'm guessing he still is.

The woman that ran the agency loved him. It wasn't just because he was a frequent customer and the amount of money he pumped into the agency, I think it was because he fulfilled her expectation on every level of what her ideal customer would be like.

He was fat (pudgy rather than obese) balding and his 50’s, every woman’s dream, and he just wanted to be our friend. He also wanted to fuck us in the arse and urinate on us, though he was still a good bloke apparently!.

From before we joined the agency we were told we had to provide all the services the agency offered. So while a woman at another agency might not want to offer say, anal sex and her agency might work around it, our agency wouldn’t. In fairness when they were always up front about it. In practice how it worked was that your first time with a new client, if he asked for something like anal, you’d say not now, but once we’ve had a few bookings we’ll do it then.

[M/F/F] I went on a date at the lake with my high school crush and a third wheeling lesbian, got stranded out in my car for the night with the two girls, and ended up with an awesome threesome.

I have had the biggest crush on this girl since high school. Her name is Melody. I grew up in bum-fuck nowhere, and went to dumb-shit redneck high school with this girl. Never got a chance to meet her… well, I did, but I couldn't get out more than a few mismanaged words to her. Regardless, I went away to college without ever giving myself a chance with Melody, but I never quite forgot about her.

She's the quiet-shy type, and shyness has always had a weird-sexy appeal to me despite my obnoxious, extroverted personality. Although she never had the voluptuous body of the women I shamelessly masturbate to, I was still enormously attracted to her in high school.

Of course, my feelings towards her were for more than just her reserved persona. It was her face and her eyes, specifically. Her eyes were those one in a million aqua-marine eyes that you just got lost in. If the myths of a prostitute that could make a man cum from just staring into his eyes in Game of Thrones are true, then she would be that prostitute.

My paid sexual encounter with a 69-year old woman

I will start from the beginning.

I have always been attracted to the idea of paid sex with a stranger that I just met for the first time, but have never lived out the experience. The appeal is tied the thought of having an encounter where there are truly no strings attached and the whole reason for being in the same room is to simply have sex. There is also an "I'm in charge of this." edge to the fantasy that is not something that ever happens in a normal sexual exchange.

I recently had a small financial windfall and decided that it was time to live this fantasy for real. Just the act of making the decision to do it was enthralling. The next step was to "shop" for the woman I would hire, and the task was akin to being a kid in a toy store with a wad of money. I know that doesn't really paint me in a positive light, but it's what it is. Just the act of looking was a fun and extremely satisfying activity.