Now, I cannot – will not – divulge certain information as to exactly how and where, but, I recently found myself becoming acquainted with a prostitute. ‘Acquainted’ is not a euphemism – I have not paid her for sex, let alone engaged in it with her. When I told her I wanted to write about her for my little blog or maybe send something to a magazine, there arose the subject of how she ought to be identified. “You can’t use my name,” she said. That goes without saying. I told her I was going to call her Misty in the writing. She said “No,” and rather emphatically at that. Lacey? “Why do you want me to sound like some stripper? Call me Jane.” “Jane V.?” I asked. “Ha. Ha. (sarcastically) V for vagina?” We settled on Jane.
Although Jane is a hooker by definition in that she takes money for sexual favors, she is not a hooker by stereotype. She is not to be seen late at night bent at the hip, a short skirt lifting up to expose the top of her thigh-high fishnet stockings with one hand on the roof of a car, the other resting on the small of her back while she coyly negotiates with a john. No. Rather, Jane spends most of her “working hours” (euphemism) in the late afternoon or on weekends. She is usually wearing jeans – sometimes with holes in them – or leggings and a hoodie with her hair pulled back. Jane is quite appealing, don’t think otherwise. Her attractive figure is still perceptible through her jeans and hoodie. (I’ll stop here with physical description since I don’t want to describe her in too much detail – for obvious reasons.) Her attractiveness is how I met her in the first place (as is likely the case with most prostitutes).
I met Jane on a dating app. I messaged her first. We met downtown for the first time – actually we always meet in the city (she’s never come out to the suburbs). I met her at a Potbelly’s during my lunch break. In our messaging beforehand, it seemed established that we were meeting as friends only (i.e. this was not a “date”). On her profile, as on mine, one sees that she is looking for “short-term dating, long-term dating, new friends.” We were becoming new friends. During our lunch I learned that she already had a boyfriend. I don’t know if I said something or if she was able to divine from my body language (or perhaps a silence?) that this fact perturbed and disappointed me a bit, but she chose to then inform me that she’ll still hook up with other people. Hmmmmm. OK….
This excited me. Was she shopping for a booty call or something? I’ve never thought of myself as the kind of guy a girl would want in her phone solely for when she was horny or bored. “So you cheat on your boyfriend? Are you in an ‘open relationship?’” I used air quotes condescendingly. I learned it was not exactly an “open relationship” but he did know she shagged other guys. Then she told me it earns her money. Immediately, Jane changed before my very eyes. She didn’t seem like a sexy student anymore but more like a sad piece of trailer trash, hot, yes, but depressing. I could very easily picture her smoking cigarettes and not showering for days at a time. In my mental photos of this version of her she is mad, usually in a half-yell, arguing. I have seen crack whores before and was drawing on those images. Those thoughts faded and I became somewhat desensitized to this news after some more conversation. By the time we left the restaurant, I perceived her as I did before she told me: cute, touchable, clean. It was hard to work the rest of the day. I kept looking at her profile pictures and – I admit it – was kinda horny. We met the next week and then began to get lunch together once or twice a week. I also wandered around the city with her once on a Sunday, doing nothing in particular.
Jane is a couple of years younger than me and works and lives in the Chicago. She is a student at one of the universities and also has a part-time job (I’d rather not say what it is, but rest assured, it’s a normal job). She has a boyfriend, or rather, a guy she sees and goes out with sometimes. (‘Boyfriend’ doesn’t seem right. I think he just ‘dates’ Jane for the occasional roll in the hay. He’s a full-time student at her college and it sounds like his studies come before everything – more power to him.) Jane has feelings for him though. She explained this to me when I asked why she doesn’t just charge him too.
Jane charges fifty dollars for blowjobs (it just occurred to me now that she wanted to be Jane because of ‘Dick and Jane.’ I don’t know.) and $150 for sex. NO ANAL (atta gurl). I began to feel some relief the more I talked with her. For example, she told me that she doesn’t really do either very often, but “probably only a couple blowjobs a month.” Straight intercourse for money sounded like more of a rarer occurrence. Also, she is very selective with her “clients.” She will only solicit guys she would want to have sex with anyway. If she’s at a party, perhaps a little tipsy, a little horny, she’ll keep her eye on a hot guy and eventually, when the timing is right, find him somewhere and straight-up say “I’ll suck your dick for fifty dollars.” She says it works perfectly because even if they don’t want to do it, she just plays it off as a joke and laughs like a drunken idiot. Usually, giving them head turns her on, and if she finds herself wanting to have sex, she will offer the sex for $150 and make even more money as she gets her rocks off. Sometimes she gets carried away and has sex anyway without the higher price but still getting the fifty bucks for the prelude of the blowjob. These poor suckers.
Usually she never hears from these guys again. I suppose they don’t want the word to spread and then get expelled. There are a couple of guys though who will call periodically and proposition her. This is the closest thing she has to a “regular,” but, like I said, these are guys she would fuck anyway. It’s win-win for her. Imagine someone you want to fuck calling you and saying they’ll pay you to fuck them once every month or so. If Jane ever gets propositioned by someone new whom she’s never been with before, she tells them to fuck off and accuses them of being part of the “rape culture.” I told her that’s some bullshit: she could get one of them expelled. She said that she only does it to their face in private to scare them out of trying again or thinking that she really does give head for bread (corny, I know).
Eventually, I didn’t feel uncomfortable about the subject anymore and whenever I asked her about it, she would answer any question. I never asked about any raunchy details, examples of which I do not want to write here. Besides, those are just sex questions, not necessarily prostitution questions. Once I asked her if she ever gets nervous or scared about getting caught. “Only sometimes,” she said. But it seems that everyone involved is conspiring together yet unbeknownst to one another, for if one gets caught, they all go down. If one of the guys were to rat on Jane, she’d rat on him – and possibly others. The thought of her family finding out is the only thing that will make her lose any sleep. Strangely, she admits, she doesn’t really care about the selling of the sex, she just doesn’t want her parents to know she is having sex.
I’ve eased up somewhat on my contact with Jane because sometimes her whole situation makes me uneasy and I get paranoid of being caught in some crazy bust (cops, not breasts) or something. But it sucks because she is a genuinely fun person and easy to be around. Plus, like I said, she’s quite attractive and it’s nice to walk around the city with a pretty girl all day. She hasn’t solicited me (which I admit, kinda disappoints me), but even if she did, I’d decline. I swear I would!!!
DA-PHNE (chicago) 
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