Random acts of escorting

We got a note a few weeks ago from a girl in, of all places, Pittsburgh.

Her note directed us to a website unlike any escorting site we’d ever seen. Pictures, hundreds of pictures, of bars, of restaurants, vintage clothing stores, some high fashion boutiques and, interspersed, shots of a girl. It was hard to tell if it was the same girl from shot to shot.

The words were equally ambiguous. Quotations for the most part. The effect was like a neighbourhood scrapbook of a place we’d never been featuring glimpses of a girl we never saw in full. Of course we were intrigued. Of course we got in touch.

by Hannah Jay

“So you liked my website.” said Carre. “Some people get it, others don’t. Which is my whole take on escorting right there.”

“I arrived in Pittsburgh with a girlfriend who was doing graduate work at Carnegie Mellon. Total Brainiac. Loved her a lot but I loved Southside Flats and East Carson Street more. So when she got a post doc in California, I stayed. I was twenty four and I had a couple of years of college but that was not at all what I wanted to do.”

I had done a bunch of stuff in Pittsburgh – worked in an office, sold vaping supplies, did some retail downtown – all those sorts of jobs. I didn’t really fit in with any of them. A bit too alternative for retail or office work, not nearly alternative enough for server jobs at hipster bars on Carson. Plus, and this was the thing, I had somehow bought a really sweet little house a couple of blocks off Carson. I had inherited a bit of money which covered the down payment.

Long story short. I was fast running out of money and I’d have to sell the house unless I found something to do. And it needed to be pretty lucrative. I made one of those lists, you know, with all the possibilities and, for some reason, right at the end, I wrote “escort”.

Beside escort I wrote: “illegal, yeccy, dangerous”. I thought for a few more seconds and then crossed out “illegal”, because escorts are legal, and added “$$$” instead. Or at least I thought it might be. But the thing was, for me, pretty lucrative was about $3500 a month because my mortgage was $1350 a month. There are really not a lot of jobs which pay that sort of money.

To make it a bit more complicated, just as I was hitting this cash crunch a guy I knew offered me a great part time minimum wage job in the whiskey bar he was opening up on Carson Street. The great thing about it was it was only two nights a week and because he felt guilty about the minimum wage thing he offered me a piece of the business if I stayed for a year. The tips had the potential to be good. I took the job but I was still a couple of thousand dollars a month away from making my nut.

Southside Flats is a really tight little community. Sure, on the weekends there are thousands of people in the bars from all over Pittsburgh, but during the week it is quiet and actually really friendly. Meanwhile, just across a bridge, was downtown Pittsburgh with big banks, huge corporate headquarters and all sorts of government, academic and medical people making huge amounts of money.

My thought was if I could pull a few of the suits across the river there was money in it.

My second thought occurred as I did a bit of research on advertising options. Wow, I don’t want to be nasty but the “girls” who were advertising as escorts sounded scary. I mean sure, escorting is going to be about consenting adult activity at some point but the ads were just so “to the point”. All 38DDDs and booty shorts; I could not do that if I tried. So I didn’t.

Does it make any sense at all to talk about artisanal escorting? I had no idea but I figured it was worth a try. I had my pretty little house, all square up and down with three bedrooms and a nice batheroom upstairs and a living room, dining room and kitchen on an open plan on the first floor. There was even a hall. My question was whether I could figure out a way to reduce the “illegal, yeccy, dangerous” factors enough so I would be happy seeing a few men a week.

I wasn’t all that worried about the consenting adult activities. While I usually date women I love men. Especially older, well to do, non-hipster men. I like my social life to be in female friendly parts of my community, but if I was going to do the escorting thing I would make use of the bars and restaurants on East Carson Street.

Here’s the thing about East Carson Street: there are two or three blocks which have been transformed into some of the coolest bars, restaurants, tap rooms and dive bars you can find anywhere in America. Plus, and this is a huge factor, while it gets a bit rowdy on weekend, Carson Street is amazingly safe. You can park your car and it will be fine, I walk home from work at 2:00 AM and I don’t worry. It helps that my house is a block away.

While there are plenty of the neck bearded, plaid shirt, wearing hipsters floating around Carson, across the river there are these same guys but they are in town on business or they work downtown. So they don’t have the beards or the tattoos but they still like the whole “modern food, hand made whiskey, craft beer” ethos. And they have a lot more money.

Like the hipsters on my side of the river these guys love the idea of experience rather than stuff; but, escorts? No way. Not at all cool. Sexist, often racist and definitely oppressive because, after all, it is the inequality of income which forces women to escort. And so on. So the very people I wanted to have as my clients were way too hip, too socially concerned, to even think about hiring an escort.

Which goes a long way to explaining my weird website. I am not so much selling an escort date as offering a guided tour of the more interesting parts of Carson Street. I am a girl who likes her cocktails and since I came to Pittsburgh I made a point of spending time in most of the bars and tap rooms on the street. After all, I help run one of them. I know the burley guys with full sleeve tats and beards which have not seen a comb in a year. I know the wait staff in most of the restaurants. I am a member of a couple of clubs which don’t officially exist right in the middle of the Carson Street world. And all those people know me.

My idea was to come at escorting a bit obliquely. First off I was not willing to offer any sort of escorting date which was just “consenting adult activity”. There is no question that the Pittsburgh law enforcement people run stings on a regular basis and I wanted no part of that. Second, I wanted to offer an actual, fun, bar and restaurant tour of East Carson Street. Meet at one end of the strip, end up at the other which is around the corner from my cute little house. I wanted to make sure that there was no way that any fee I might charge could be seen as just money for sex. If you look at my website you’ll notice that there is no real mention of any sort of sex: just pampering, luxury and fun. Which is what you get.

I realized that while I could use escorting websites to advertise my services, it was smart not to advertise on the sleazier sites. First, I didn’t want those customers, second, law enforcement is lazy and they will go there first. I picked sites with national exposure.

My ads were all about “Exploring the hippest strip in America” and “Let a pretty, alternative girl be your guide to the fun, food and nightlife of the East Carson Street Strip”. The only contact information I gave was my website. I didn’t quote rates and I never, even on the phone, discussed any services. If a potential client had trouble with that I simply pointed out that this ambiguity was for his security and mine and that he could be assured that his tour would be tons of fun.

I think part of the artisanal escorting model needs to be taking the entire idea of escorting and turning it on its head. Instead of the purely transactional, money for sex, idea, I took the idea of paid companionship seriously. I didn’t really have an “escort persona” because I was not really hiding what I was doing from anyone. I couldn’t because I needed the help of the servers and the bar owners and the restaurant managers to make the evening really memorable. Which is not to say I announced that I was escorting. I said nothing and let them try and figure out why, a couple of nights a week, I would be out with a different, beardless guy in “Dad” pants. But the thing about Southside Flats is that everyone is committed to doing what they really want to do without a lot of judgement. So I had no trouble.

Taking a guy to three or four bars and two different restaurants where everyone knows my name and the really brilliant food arrives unordered in sample portions five minutes after I walk through the door really reassures my clients. They realize that I have a lot of roots in this community, that I am safe.

I love dressing for these dates. I know my date is going to look a bit out of place but I like to play the hipster girl who does not quite get the under-sexed ethos. I take my look from the opening video for Portlandia, “All the cute girls wear glasses.” I do. Big ones. And I have my hair in a long messy bob, usually dyed a really brilliant platinum or shimmery grey. It changes. Depending on the weather I am either wearing one of my vintage, deliciously soft and well worn cashmere sweaters or a little silk cami. Never a bra. I don’t like bras. I have tiny boobs. I do like little skater skirts or really lacy longer dresses where I can wear stockings instead of tights. Boots or runners depending on the weather and a bunch of different coats – it gets cold in Pittsburgh. Red, red lipstick and a little eyeliner and mascara and I am good to go.

I may have tiny boobs but I have nice long legs and I enjoy showing them off. Almost every one of my escorting clients makes a point of complimenting me. My whole look is completely anti-escort. Which always makes it fun when they first meet me. As you can see, none of the pictures on my so called escort website really shows my face. I’m either in shadow or turned half away from the camera. Totally deliberate, Pittsburgh is a big city, the Southshore Flats are a village.

I always meet my dates in my whisky bar. I think it is safe to say that I never have any trouble figuring out who the date is and I spend a couple of minutes behind the bar taking a good long look. Of course he is also on the bar video. Something else I don’t mention. They don’t know it’s my whisky bar until the first drink turns out to be on me. Jake, my whisky slinging partner and a major hipster bruiser has a little routine where he brings the drinks. He’s a teddy bear but with loads of tattoos and big. All he says is “Drinks are on the house. Enjoy your tour with Carre.” Which is all he needs to say. He is sufficiently intimidating that I have had clients make their excuses and leave. Which is fine.

One drink at my whiskey bar and then we walk down the street to one of the tap rooms. Which ever has the best drink special that day but I know them all. Then one of the restaurants where we have a tasting platter. Small food. Usually great and certainly a break from downtown hotel food. Then another dive bar.

If my client is having fun and is fun to be with and is sipping rather than shooting his drinks, I might take him to a tap room where there is live music.

Oh, almost forgot, business takes place at my whisky bar. This lets me put the money in my locker and forget about it. I am not terrifically expensive. In fact, per hour I am an amazing deal. But I like to have the money for the “tour” out of the way. Critically, I have the exchange of money on tape hours before any suggestion of activities between consenting adults take place. Date stamps are important. And yes I do sound a bit paranoid but the reality is that escorts can be harassed by law enforcement. I have no intention of letting that happen to me.

By the time the evening is coming to its natural close my client will usually be a bit buzzed, very well fed and more than happy to do what he is told when he gets to my house. I know I sound paranoid about law enforcement but I am totally serious about avoiding any problems. I have a great, free standing tub in the master bath and that is where my client is sent after one last little snack. I run up and turn on the water and ten minutes later off he goes. I, of course, keep all my clothes on and discourage any, what my grandmother would call, hanky panky until my client is fresh and clean and, most importantly, naked. Is it a sure fire way to identify a cop? I have no idea, but I do know that it is awfully tough to arrest an escort when you are buck naked.

From there, as you might guess, consenting adult activity proceeds without much difficulty. I like men and I enjoy the pleasures of the bedroom. I would not even think of escorting if I didn’t.

As I said, all this takes most of an evening and that is just fine with me. I have an income goal every month from my escorting business and I routinely exceed it. The funny part is that about half my clients will book an evening a month so now I barely have to advertise. Again something I like because a random escort ad is less likely to attract law enforcement.

For me the whole escorting business is a very random thing. I will have some weeks with four dates and some with one. It doesn’t actually matter because with four escort dates a month I cover that nasty nut, the rest are really about having a very entertaining life.

Believe it or not the biggest issue for me with escorting is having to watch my weight. The first two months I was doing my tours I ate far too much and didn’t really notice until I tried putting on a cute little pair of cutoffs and couldn’t get them done up. Yikes. Escorting makes you fat? Who knew? So I do a gym bunny thing a couple of mornings a week and eat a lot less on dates.

I don’t really have any big plans for all of this. I like leading my life, working with Jake, working on my house. I see a couple of girls casually neither of who know I escort. I think one of them would be fine with it the other would think I was somehow exploited by the patriarchy or something. Quite honestly I don’t really care.

My whole take on escorting is that it is something I’ll do for a while and then, at some point, I’ll stop. Or at least I’ll stop advertising. I don’t think I’d stop seeing my regulars because we have a great time together. It really is like hanging out with a friend who you like taking to bed and who gives you $500 or $1000 for being good fun.

I don’t really think too much about why my escorting clients come to see me. What’s the point? For a few hours once in a while they get to live a life they decided not to live full time. They get to drink whiskey with a boho girl who they know is going to take them home with her. I don’t think you need to look too deeply for a lot of explanations.

In a lot of ways I wish there was some other word than escorting for what I do. Not because I am shy about the whole escorting thing but I am pretty sure I am doing something which is very different from the more basic escorts. I keep going back to that idea of artisanal. I craft my clients’ experience of a wonderful little part of the world which, in their normal lives, they may have heard about but are not likely to visit. I am as much a guide and a companion. I know which craft beers to try and which to avoid. For an hour or three, they can imagine what their lives would have been if they had stayed in the hipster world and dated a girl like me.