Chapter 1: My New Job

I was happy with my job as a high school math teacher. The pay wasn’t great, but I knew that going in. I was young and attractive and had heard that I was considered “the hottest teacher in school”. I found out about that when I confiscated a cell phone from one of my students because he was using it in class. I couldn’t resist looking at his recent activity and saw several text messages from other boys that backed up his assertion that I was a TILF. I knew what a MILF was, so it didn’t take me long to figure out what that acronym meant. It was a bit surprising but nice also. After that, I started dressing more provocatively, still within the dress code for teachers, but something my new “fans” would enjoy. I know, bad me.

Like I said, I was content with my life. I had learned to live within my means. I hadn’t had a real date in a while, but I wasn’t celibate. I would occasionally put on my sexiest outfit and go to the tourist side of town, where there were lots of large, fancy hotels. I would hang out in some of the hotel bars, and if things went well, I might end up with a one-night stand with some cute guy that was enough to keep my libido in check. Maybe I was trying to live up to that TILF label.

Things changed when I ran into Sarah Mitchell one Saturday afternoon at my favorite mall. We went to high school together and ended up at the same college. We were both Education majors with an emphasis on teaching math, so our friendship grew as we worked toward our degrees. After graduation, we got jobs in the same city at different high schools. I hadn’t seen her for a few months and was surprised by her appearance. If I was hot, Sarah was sizzling. Her clothes came from stores I could never afford, and her long red hair was stylishly draped over one shoulder. I think the expression is, “You look like a million bucks,” but I didn’t say it out loud.

We decided to catch up over lunch at a Chinese place we used to visit. Sarah said she would drive, so we headed to the parking lot. When she pushed her key fob, an almost new, silver Mercedes beeped back at her. “That’s yours?” I asked, even though it was a stupid question.

“Yep, it’s two years old and only has 18,000 miles on the odometer.”

I knew even a used Mercedes was out of my price range, and her clothes didn’t come from the same places I shopped. “Damn, girl, they must pay a lot better at Taylor High. You’re livin’ large.” I knew that wasn’t possible since we both worked for the same county school system. Even though I was curious about her newfound wealth, I didn’t ask.

As we left the mall, instead of heading for the restaurant, she drove to a park where we used to hang out as bratty teenagers. I wondered what she was doing when she pulled into an empty parking spot in the shade of a big oak tree and finally broke her silence. “I’m going to tell you something that may surprise you, shock you, or even make you hate me, but I need you just to listen.”

“Damn, Sarah,” I said, “are you a hitman for the mob now?”

She took a deep breath, and I knew whatever she was about to confess was something big, so I tried to contain my snark and just listen for a change. “I have a side hustle, and it’s not working for the mob, wiseass. I’m an escort.”

When she said that, it was so unexpected that it took me a few seconds to understand what she had said. “An ... escort? As in hooker?” I asked.

“Hookers work on street corners or in bars. An escort finds her clients online.”

The comment about meeting guys in bars hit close to home, but I didn’t say anything. “You mean like backpage.com?” I asked. It was the only site like that I knew anything about.

“That’s a little too ... uhh ... rough for me. There are lots of trashy women there and even rumors of underage girls being trafficked. No, I work for an agency that has its own website. The men who use it are vetted and as safe as possible, considering the business.”

“Aren’t you afraid of being arrested?”

“That could always happen, of course, but part of that vetting I mentioned is trying to ensure we aren’t walking into a sting.”

“What about disease?” I asked. I was getting more curious, even though I wasn’t sure why.

“That can be a problem, but condoms are a requirement, and if the guy seems sketchy, you can always leave.”

“So, they don’t come to your home?”

“God, no. That’s called incall, and I don’t do that.”

“So,” I said, trying to make sure I understood, “you get a call from some guy, go to wherever, and have sex with him for money?”

“It’s not quite that simple. Like I said, I work for an agency with a website. The men find us there, and if approved, contact us by email. Then, if things seem okay, we arrange a date, usually in a hotel or sometimes at their home. Believe me, these guys have some nice homes. That’s pretty much it,” Sarah said. “I told you it might be shocking.”

I wondered if Sarah or one of the other girls from that site had been working in one of the hotels while I tried to pick up guys for free. “How long have you been doing this?”

“A couple of years,” she said. “Slowly at first, but now I get at least one call a week, more when there is one of those big conventions in town.”

I’m good at math, but I can be a bit slow when it comes to other things. That’s why it took me a moment to realize why Sarah was being so candid with me. “Are you trying to ... recruit me?” I asked.

She smiled and said, “Are you interested?”

I was, so after Sarah answered about a thousand or so other questions I had, she arranged for me to have an interview with the woman who ran the site. It was all online, and I never found out where the company was. I got the feeling that they worked in several different cities. The woman Sarah put me in touch with was a very nice lady named Naomi. At least that’s what she told me to call her. Pseudonyms were part of the business. My friend Sarah’s escort name was “Meghan.” Naomi appeared to be in her mid-forties and projected an air of confidence and authority. Talking to her reminded me of interviewing for my first teaching job.

After half an hour of conversation, Naomi finally asked me if I wanted to go to work for her. I told her I was willing to try, so she sent me a contract to sign and return, then scheduled me to meet with a local photographer to get some pictures for their website, and I was on my way to selling my body for money. I tried to convince myself it wasn’t much different than what I had been doing occasionally as an amateur, but I also knew that now I wouldn’t be able to pick my potential sex partners.

A few days later, I got an email from Naomi telling me to go to her site and check out my page. My escort name was Kitty (not my choice), and when I entered that name, my official escort page popped up. I saw two of the probably fifty pictures the photographer had taken. One was a headshot, all fancy and not looking much like me. It looked more like something Glamour Shots might do. The other picture was a full-length shot of me in a tight red dress that Sarah had helped me pick out. I stared at the image momentarily, wondering what the men who clicked on my page would think of me.

There was a description next to the pictures, most of which had been made up by Naomi. There was a ‘More’ button under it, and when I clicked on it, another page was displayed with more of my pictures, including some where I was wearing more revealing clothing, a revealing nightgown and a bikini. I felt like I looked good in all of them. I’m short, 5’ 5 “ or so, with a slim body that I try to maintain. My breasts are average-sized, with what one of my boyfriends called “spectacular” areolas and nipples, which weren’t displayed in any of the PG-13-rated pictures on my page.

So, there it was. I called Sarah and told her. She agreed that I looked desirable and should expect to hear from men shortly. Clients didn’t contact the girls directly. They went through the site, which gave Naomi and her staff time to vet them before they were allowed to contact the girls they were interested in.

I waited impatiently for a couple of weeks and almost gave up when Naomi sent me a notice telling me to expect an email from my first client. His name was George, and he claimed to have never done anything like this. From our brief email exchange, I learned he was middle-aged and divorced. He visited our town several times a year for business. He told me where he was staying, and we agreed I would be there at nine o’clock that night.

I parked behind the hotel and walked around to the front. I was wearing a coat too warm for the weather, but Sarah had warned me that my very revealing dress might attract too much attention when I walked through the lobby. Even though Naomi had told me that there were a lot of escorts working at the two large conventions in town, it was still a good idea not to attract attention as I walked through the lobby. Occasionally, hotel security would be looking out for girls using the hotel for their sex work because they didn’t want to attract the attention of the vice squad. Her advice was to look like I belonged there, so I walked straight through the lobby to the elevators and took one to the third floor.

When I found room 312, I hesitated before I knocked. I knew George was waiting for me inside, and I was probably more nervous than he was. I had never had sex with a total stranger, and certainly not for money. What if he didn’t like me? What if he was some kind of weirdo? What if he wanted me to do something I didn’t want to, even though my limits were listed on my page? And worst of all, what if I was walking into a sex sting? Having my picture on the six o’clock news would end my career.

I was right on time, a trait I had learned as a teacher. I looked up and down the hall before I knocked. I didn’t want anyone to see me going into the room. Somehow, I just knew they would know why I was there. That was the kind of fear I had to overcome to begin my career as an escort. I took a deep breath, tried to calm my paranoia, and knocked.

George must have been standing close to the door because he opened it almost immediately. He stared at me momentarily, then said, “Oh my, you are even more beautiful than your pictures.”

“Can I come in?” I asked. George hadn’t lied about his appearance or age. He was in his mid-thirties, and his male-pattern baldness was already taking a toll. He wore wireframe glasses, which he constantly pushed back up his nose. My first impression was that he looked like an accountant—a very nervous accountant, maybe about to accompany a client to an IRS audit.

He laughed. “Of course. I’m just stunned that you are here. I’ve never done this before and thought it might be a scam.”

“Nope, I’m here.”

I followed him into the room and took a quick look around. Sarah had told me that I could get a good idea of how the appointment (that’s what she called it) would go based on how messy or neat the room was. George’s room looked like he had just checked in, even though I knew he had been there for three days. That was part of Naomi’s background check.

“Get the money first,” Sarah told me when she gave me my final briefing. I saw a dresser with an envelope lying on one corner. Kitty, my escort name, was written on it, as we had agreed. I didn’t say anything and didn’t look inside. I just tucked it into my purse. So far, no surprises. I took my coat off and put it and my purse on a chair by the door.

I heard George gasp when he saw my dress. It was the same one I was wearing in my homepage picture, bright red, mid-thigh short, tight across my hips, with a plunging neckline that drew attention to my average-sized boobs. If a dress could talk, it would have shouted ‘hooker here’, which was the reason for the coat. I did a quick pirouette, letting him get the full view.

“You like it?” I asked.

“It’s amazing, and you look great in it,” George said, his voice jittery with excitement. Sarah had told me that the best clients were often jumpy, nervous, or scared.

“Take charge,” she had told me. “You can usually get a guy who is jumpy or nervous off quickly. It’s the calm, controlled guys who want to get every minute of the time they’re paying for.”

“I’ll bet you’ll like me even better out of it,” I said, stepping closer to him and turning around. “Little help, please?” I asked, pointing to the top of the zipper. I could feel his hand shaking as he searched for the slider on the zipper. He finally managed to find it and pulled it down. I didn’t turn around, keeping my back to him as I shrugged the dress off my shoulders and let it fall to the floor. I wasn’t wearing panties, so he got a good view of my bare butt. He briefly patted it, almost like he was afraid I might slap him for doing that. His shyness was almost cute.