This Is Me is a column in which we speak to Washingtonians who have a unique story to tell. Did you leave your job on the Hill to become a bartender? Are you getting your tubes tied because you don’t want children? Do you support yourself as a social influencer? We want to hear all of your stories—no matter what the subject or how kooky they may be. Email Mimi Montgomery at mmontgomery@washingtonian.com.
Who: A single mother now working as a contract bartender
Age: 39
Where she lives: DC
On how she found out about the business…
“I was comfortable for a time hooking up with [different] guys, so I’d be on Craigslist and sometimes I’d [use it to] hook up. It was more instant gratification—this was before Tinder and all that started. It was risky, but it was never anything too crazy. If my dating life was boring, it was just something I’d do.”
“I’d been used to the Craigslist community for a few years, looking around on those kinds of sites [like Backpage] and being on the swinger sites from time to time. I figured a quick way to make money was to throw a party. [On those sites], groups would post every week that they would have a party at a hotel, and they’d have pictures of the girls they’d have there and guys could answer back and pay like, $75 to come to the party. They’d call it a swingers thing so it didn’t seem like it was actual prostitution…but that was what was going on. So [a friend and I] decided to have one of our own.”
“I put an ad out—you know, a lot of the girls, they just wanted to make quick money. So they were down for it. The only expense we’d have to put up front was getting the room, Then we’d [tell the guys] to pay a rate at the door and they could pick from five or six girls to have fun with for the night, and then we’d pay the girls based off that fee.”
On how she started working as an escort…
“[That first party] was in a hotel room in College Park. That was before College Park got busted for all the low-end prostitution. We made the cut. It was understood that I was just the hostess. I had a male friend there, and he was like the bodyguard-slash-money-taker. I was in the room facilitating in some lingerie, offering drinks, making sure everybody was safe and cool.”
“[One guy said] he’s having a good time, but he was really interested in seeing me. And I told him that’s not an option. I’m just hosting the event. [Then he said] I can offer you 600 bucks. So I was like—oh. So we exchanged numbers or something, and I got to talking to him and eventually saw him.”
“He was a realtor out in Maryland somewhere, older white guy. It was not a sexual thing—he wanted it to be like, a degrading kind of role play. I was just thinking about it like, oh my gosh. Is this really happening? Is he really going to bring $600 for me? So I just prepared myself for whatever.”
“I got a lingerie outfit from one of my girlfriends, and we set up this whole thing where he was a puppy dog and crawled around on the floor. I gave him commands on what to do, and he wanted me to beat him with a newspaper. I had bought a leash, and was [leading] him around on the leash and beating him with it and doing different commands. I had cookies, but I was treating them as dog treats and made him eat out of a bowl. Stuff like that.”
“At one point—it was really uncomfortable—he wanted me to walk on him in my heels. So I did a little bit of that. At the end, I didn’t know if he needed any kind of sexual release, but he was like, no, no. It’s cool. This is all I really wanted. So I was like, okay, and we hugged, and that was it.”
On her clients…
“I was looking for more of the companionship and escort aspect, not so much the quick money [of prostitution]. A lot of the time that I escorted, I had a lot of guys come to me with particular fetish requests. I’d see guys that’d kind of get obsessed with me. [I was building] a relationship with repeat customers to the point that, over the five years [I was doing this], there were guys I’d seen, oh my gosh, so many times. Like monthly or weekly.”
“One guy, we never had sex. It was just straight oral. One guy had girlfriend issues, so he would always want to ask me girlfriend advice. A couple guys, they wanted me to urinate on them. I had one guy who wanted to drink my urine. I had another guy, he wanted to wrestle. He paid for my dinner, we had the whole date and then finally got to the wrestling, and again, I wasn’t sure if he needed something sexually done. I went to give him a hand release, and he like, froze up. He was like, that’s not what this is. I just wanted to wrestle. And I was like…okay.”
“My day would consist of getting up, checking the message board, checking emails to see if anyone had emailed me from the previous night, setting up appointments. I had my regulars on one schedule, but I also allowed for new guys. I probably worked like, four days out of the month, and then I’d probably make anywhere from $2,800 to $3,500. I was [charging] around $250 an hour at first, and then when I was finished, I was getting about $400 or more an hour. Towards the end, I was offering [the clients] doubles and dinner. I actually did it at my home, and they got a home-cooked meal and I’d invite one of my girlfriends over and we’d have a threesome. I’d offer that for $1,400, and they were going for it for like, three hours.”
On what she told people…
“A few of my friends knew about me seeing guys, maybe in the capacity of like, oh, you’ve met married guys online and they’re like, taking care of you. I even kept it from my therapist for three years. My family—I don’t know if they’re under a rock. They just kind of never said anything to me. If my mom needed something or my dad needed to borrow money, they would come ask me and never say where are you working? It was kind of scary because I was like, wow, they’re actually not asking me where this money’s coming from and I’m getting like, thousands a month in cash that I’m not claiming.”
“[I didn’t worry about my son finding out]. He was young enough, and he always had a sitter. All the hours that I would see the guys would be before 6 PM, so it was like a regular job. I could start taking appointments at 10 and be done by 6, home cooking dinner, and no one would know. It was funny—my girlfriends [that knew] often joked with me, oh, you’re a ho and a housewife, because I would go out and take appointments for like, an hour, two hours, come home, and be like, I’m baking cookies.”
“[But] I was constantly researching how to do it beyond Backpage. I have a kid; I didn’t want to get busted. I didn’t want to go to jail. It was just too risky for me—all my family’s in this area, all my friends. I didn’t want my name out there doing this.”
On why she decided to stop escorting…
“At the time, I was getting too good at it. It was going on five years. It was really isolating. You can’t talk about this. You have a bad day escorting, who are you going to talk to? [And] what is this going to look like down the line? What is this going to look like when I’m 40? I mean, there were woman who were 40 and still escorting who lost custody of their kids and had criminal records for prostitution. It was just like, I can’t do this forever. I’ve got to get out.”
“I got my head straight and I was like, I want to fall in love and have a real relationship. Yeah, I probably will think the guy will cheat on me, but at least I know a little bit more. I found out a lot about men, of course. I mean, even the guys that I would never say oh, he’s a cheater. I had some little lawyer guy in Georgetown come see me. [Afterwards, he] said I have to go to dinner with my wife now. Goodbye. Like, what? He was so petite and nice. It blew me away. It’s crazy.”
“And still, even now, dating is rough because I don’t take a lot of guys’ crap. I can’t believe them on everything. If they do that whole let’s chat online thing and they go ghost for a couple days, it’s like, oh, you have a girlfriend. You have a wife. I can tell.”
“One of the girls that I would do doubles with, she found me and was sending me DMs on Instagram. I’m like, dude, that’s a different life. Please don’t contact me. Even last night, I worked an event at a hotel, and I got propositioned. It still happens. It’s still like that temptation, you know? Do you want to go back and do that? It just doesn’t stop.”
This interview has been edited and condensed.
Mimi Montgomery joined Washingtonian in 2018. She’s written for The Washington Post, Garden & Gun, Outside Magazine, Washington City Paper, DCist, and PoPVille. Originally from North Carolina, she now lives in Del Ray.
