If you’ve had the pleasure of meeting me, you’ll know that I can speak openly about my past as an escort. It wasn’t always like that. In fact I still hesitate to share that information with certain people mostly because we live in such a slut-shamey, sexphobic society that I’m still unwrapping the residual shame I feel about disclosing information like this. Now that I have this online platform, I feel a bit more open to talk about this in detail. If my parents ever saw this though, I might just crawl in a hole and lay there to rot for the rest of my days. Sorry, mom and dad.

I graduated high school in 2011 and started my undergrad in Forensic Science in 2012. I don’t know why I went in to the program to begin with. I guess it was because I really thought it would be a lot like CSI despite being told that the real job is nothing like it. I got a wakeup call when I saw my grades in the first semester. Straight D student. My second semester was even worse when I failed all my courses because I couldn’t stomach the idea of cutting open a pig carcass. I was put on academic probation, but I eventually decided to drop out. This wasn’t my thing and I learned that the hard way.

In the summer of that year, I got a job working retail. Hours were inconsistent and management was incompetent on top of having to deal with customer abuse. At least I was making money and not getting sick and feeling like shit because my grades were suffering. One day I got assigned to do inventory. My shift partner was a really pretty girl. She had a fit build, average height, hair was styled in a balayage, her skin had a nice olive complexion, and she smelled of expensive perfume. Her nametag said “Ashley” but she wanted me to “call me Ash even though that’s not my real name.” Normally I don’t question these types of things because it’s your life, whatever. But this was a long shift and we were the only ones doing inventory so I decided to make small talk.

I said, “Oh okay, cool. I’m Tim. Nice to meet you.” I shake her hand. “Are you new here?”

“Yeah, I just started last week. I just wanted to work here to feel normal,” she replied.

“Normal? What do you mean?”

“I just wanted to get a normal job so I can feel like I’m doing something when I’m not at my other job.”

At this point I’m really curious, so I keep prying. “I get that. What’s your other job?”

“I’m a pimp.”

At this point in the story, I feel that it is necessary to disclose that I identified as bisexual at the time. This will become relevant in a bit. It took me back a bit to hear that she was a pimp. I have never met a pimp in real life before, but things got interesting and the conversation flowed naturally.

“Oh that’s interesting. Do you have, like, a team or something like that?” I asked.

“Something like that, yeah. I’m surprised this isn’t awkward for you.”

“Yeah, I don’t judge. Live your life, y’know.”

A couple hours in to our shift and we have grown comfortable as co-workers and we start talking about really mundane things like traffic in the city or where we go to eat or sharing workout routines. Time passes and we’ve reached the end of our shift, so we clock out together.

As we walk out of the store and I’m about to say goodbye she stops me to ask, “Hey can I ask you something?”

I chuckle and say, “You just did.”

“Haha, funny. But seriously, I wanna ask you something. Please don’t be freaked out.”

“Umm, okay. What is it?”

“Do you wanna come over to my place and fuck?”

Remember how I said me being bisexual at the time would be relevant? Yeah, it was very relevant. I had nothing else to do for the day I agreed. We took the train heading north and got off after a few stops. Her apartment was a short walk away from the station, and it was one of those apartments where the lobby was lined with marble and it had really bright lights hanging from its 100-foot ceiling. It was fancy. While we’re waiting for the elevator, my palms start to sweat while we’re making awkward eye contact with each other. I’ve never had sex with a pimp before. This was so random and weird. Why did she want to fuck me so suddenly? Did I say anything to make it sound like I was flirting? Is it even legal for coworkers to have sex? I had about a million questions running through my mind, but by the time I could come up with one more question, we were naked in her bed.

We’re making out really passionately. Her tongue playing with my ear and my tongue tickling the side of her neck. I slowly trace my finger from her nipple down to her clit, and she arches her back and stifles a moan. I can feel her pussy start to moisten around my fingers, and I slowly put in one finger at a time making sure she can feel every nerve being stimulated. My mouth follows suit and goes down to meet my fingers at her lips. I use my tongue to flick her lips and tease her. She holds my head and starts moving it around, ordering me to lick her a certain way or gently bite down on her inner thigh. So I comply.

“Yeah, fuck right there! Just like that,” she mutters with bated breath.

“Don’t stop! Fuck. Keep licking me exactly like that.”

“Mmhmm,” I reply as she holds my head down against her pussy.

“Okay, fuck me.”

I had only a moment to gasp for air before she grabbed my ass and shoved my cock inside her.

“Fuck! Yeah, that’s perfect!” she shouted. “Fuck me hard!”

I’m thrusting as hard as she wants me to. And she looks good with her hair spread out on the sheet, her hands gripping the pillow, and biting her lower lip. She looked so hot that it almost made me wanna cum.

“Fuck, I’m almost gonna cum. I’m so close,” I told her in between thrusts.

“Cum in me. I’m close too,” she says.

And with one final thrust I let go and let my body empty itself out inside her. She grabs my torso and digs her fingers into my back holding on for life as she starts to convulse from her orgasm. We’re breathing heavily, we’re both sweaty and covered in bodily fluids, and simultaneously coming down from our synchronized climax. I collapse on the bed beside her, staring at the ceiling wondering what just happened. I can’t believe I just had sex with a pimp. I really just fucked my coworker. Is this gonna make things awkward at work? I sure hope not.

She reaches for her purse sitting on her nightstand and pulls out five one-hundred dollar bills.

“This is for you. I want to hire you,” she says as she hands me the money. “There’s more where that came from if you work for me.”

I’m so confused. “Wait, what? Slow down. What just happened?” I ask in a daze.

“I want you on my team. You seem really cool, and you were really good just now. I want you to work for me. We can still keep working at that shit hole, but at least you can get some extra money on the side. You don’t have to agree now, but I’m just saying. You’re good and I wanna work with you.”

This was a lot to take in. I can’t believe that she’s asking me to be an escort. I don’t know anything about sex work. I don’t know what the hell is going on right now. I’m still coming down from my orgasm, and she drops this huge question on me so casually as if it’s just business as always.

“Okay, obviously you have a lot to think about. Go home and text me tomorrow.”

I didn’t realize I was so quiet. “Oh. Uh, no, yeah. Sorry…yeah, I’ll text you.”

I take her money, and I try my best to locate my clothes in my still present haze. She walks me out the door and gives me a hug. I wait for the elevator still processing what the hell just happened in there. It was a lot to take in. How did I end up in this situation? What was supposed to be a regular shift at work folding clothes and checking boxes on a clipboard turned in to…whatever that was. To this day, that whole situation feels both blurry and clear as day. It happened so fast, yet so slow.

The rush from one moment to the next was so overwhelming. The sex, the money, the questions running through my head. I had so many questions that I needed answered. I had concerns about safety. I had concerns about friends and family finding out about this. I was worried that this might come out at work and I might get fired. I was scared that this was a scam. This, all of this, was all so unexpected. What I didn’t expect was that by the time the elevator had stopped at the ground floor, I took my phone having already made my decision.

“When do I start?”