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Talking Strategy with a Craigslist Voyeur-for-Hire

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What first gave you the idea to do voyeur sessions?
I answered an ad on Craigslist. A gay man posted an ad asking for somebody to watch him jerk off while he was in town on business, and I answered the ad. I was just looking around for work; I had recently lost my job and was looking through the “gigs” section. I figured if a gay man would pay me to do that, then a straight man would too.

What would you say is the weirdest thing that ever happened to you during a session?
One gentleman had a micro-penis and he paid me to humiliate him. So I spent the better part of an hour just telling him how pathetic and disgusting his penis was.

How did you know what you were going to say to the guy? Did you just wing it?
Yeah, I did. And it was — I dunno, I actually started to feel bad after awhile, you know? After berating someone for so long, I felt kind of terrible. It’s hard if you’re not naturally a mean person.

Would you ever get physically involved with someone during a session?
No, I’m in a committed relationship.

So does your boyfriend know that you do this?
He knows, and he’s ok with it.

“I might slowly unbutton my shirt so that they can see my bra…”

Does voyeurism carry any kind of emotional appeal for you?
Honestly, yeah. A lot of times these men are divorced and lonely and not comfortable going to a prostitute. So this is something close, but it’s still clean. Some of them just want company, you know? They want to talk. I think it helps them to just spend time with another person.

Do you ever feel like you know your customers on an emotional level, rather than a purely sexual one?
Often, actually. They tell me a lot about their lives. And a lot of them are super nervous just to be there. So I try to make them as comfortable as possible. Usually, that just takes small talk. I ask them about themselves. Whether they’re lying or not about who they actually are, or what they do, doesn’t matter. As long as they feel more at ease, you know? So it’s like they’re talking to someone they know instead of just some random stranger that they called up on Craigslist.

What’s a typical voyeur session like?
I wear lingerie underneath my clothes just because it makes me feel sexy. And occasionally, I’ll be in a session, and if I like the guy and I feel comfortable, I might slowly unbutton my shirt so that they can see my bra, but I never take anything off. There’s a lot of teasing, whether it’s talking to them or stroking their leg or thigh or arm. It gets physical, but not in an overtly sexual way.

How do you decide what — if anything — you’re going to say?
Every guy is different. Sometimes it’s just instructing them, and tell them how I want them to jerk off. Sometimes it’s humiliation. Sometimes they ask for a specific fantasy that they want me to portray. I had one guy who had an incest fantasy, and he asked me to pretend I was his mom, which was weird, but whatever. Who am I to judge? It varies. If it’s a normal, run-of-the-mill guy, it’s mostly just things like, “I like watching you stroke your dick for me,” and “Does that feel good?” and “What would you do if I put my face here?” or whatever. Some guys are really reserved and some are more adventurous, but once they get more comfortable, they’re more open about telling me what they want.

When you’re not interacting with a client, what do you usually think about during a session?
Hmm, that’s a good question. I’m definitely in the moment, I enjoy it. I think it’s sexy. I mean, if I didn’t like it, I don’t think I would be good at it, and people wouldn’t contact me to do it. I have a lot of repeat clients, so it’s often not just a one-time thing. But I’m turned on by it, I’m turned on by talking dirty to them, or rubbing my leg while they’re doing it, or whatever. For the most part, I’m in it. I don’t really take myself out of it at all.

In the six months that you’ve been doing this, do you feel like you’ve improved?
I think maybe I’ve gotten better at reading what triggers someone. If you’re better at reading what works for them, then you can get them to come faster.

So do you feel like this enhanced perceptiveness has carried over into everyday life?
Maybe. I think that I’ve always been pretty perceptive about people’s motivations. If I wasn’t, I don’t think I’d be able to do this sort of thing. Also I just think I’ve gotten a lot better at vetting people. I mean, there’s a chance that this could be really dangerous, because there are psychos out there. There are people I’ve corresponded with over email for a while and they turn out to be a little crazy and you realize it. I feel like I’ve gotten a lot better at just being able to pick out what kind of person they are, and what it is that they’re looking for. I can usually tell before they even tell me if they’re married, divorced or single.

“I don’t like doing couples because the power dynamic is gone.”

Really? Why’s that?
They act very differently. I actually prefer the married men; they’re usually better-looking, and they also don’t get weird on you. They don’t email you all the time, they don’t bother you. They don’t get nasty with you… because they’re probably terrified that you’re gonna turn around and do something to fuck up their marriage. They’re just better.

What steps do you usually take to screen your clients?
Just email correspondence. Occasionally I’ll give a phone number after a few sessions, if I’ve seen a person repeatedly and they want to get in touch with me more easily, I’ll give them a number, but it’s not even my real number, it’s a Google Voice number.

Have you ever been a voyeur for couples?
I don’t like doing couples because the power dynamic is gone. Because it’s a very two-against-one type of situation when there’s a couple and I just don’t like being in that kind of scenario. The reason why I do this regularly is not because the act of watching them turns me on, it’s the power dynamic I’m interested in. Plus, couples don’t really need to pay a voyeur to come and watch them—people will come and watch them fuck for free. You could get anyone to do that. And every time I’ve ever been contacted by a couple — which I have — they’re constantly trying to chew me down on the price. As soon as someone even offers me an alternative amount of money, I won’t respond to them anymore. Because then whatever I do in a session, it’s not going to be enough, because they’re gonna be pissed that they’re paying for it.

Have you ever felt like you had to draw the line with a customer either on an emotional or a physical level?
Emotionally, no. Spending an hour together doesn’t really lend itself to that amount of intimacy. But physically, there are times when I have to tell the guys to restrain themselves; that they’re not allowed to touch me. And most — I would say 99% of the time — they’re completely respectful of it, and they don’t really try again once you say “no.” It’s almost as if they’re testing their boundaries, like, “How far can I actually get before she tells me I can’t do this anymore?” But for the most part, they’re completely receptive to me saying no.

This article originally appeared in Hooksexup’s Storytime series.

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