One of my Instagram followers—who inquired about my services earlier this year, but lives too far away and couldn’t afford me—sent a direct message recently saying that he’s never been able to talk to a woman about sex or fantasies without it being “seeped in a relationship and the fear of being rejected for actually saying” what he wants, and that he sometimes “desires the conversation more than the physical act.” He added, “You are so open about sexuality and that drives me wild.” He also admitted that he was debating sending the message. He finished it up with, “You probably think I need therapy, not a professional companion….”
I responded almost right away. I know it’s tough being vulnerable with a stranger: “Not at all! And I’m flattered you feel open with me (it’s one of my natural talents), but what I was thinking, and I hope this comes out right, is that I don’t want to get into a situation where I’m here for you without compensation. I hope you understand. A lot of what I do for work is allow men to be themselves, but they pay me. I don’t do it for free.” That last part wasn’t entirely true…it does happen without compensation, but with men of my choosing—I’m sure my readers, including him, know this by now. Anyway, the conversation continued and we finally figured out a possible scenario that would work for us. We said we’d have an email date the following day when he got home from work. He sent me money via PayPal before we ended the conversation, and then emailed me a letter describing his sexual history. Which confused me a little—I still wasn’t exactly clear on what he was hoping to get out of our communication, but I was pretty sure he wanted someone to tell his secrets to. Someone he knows is a fellow kink, and with whom he can be totally free. Who knows, perhaps this will be my fallback career?
The sexual history email was interesting. A portion of it turned me on: it was a story about him jacking off in the bushes near a river when he was younger. I made myself come to the visual. Something about him needing to ejaculate so badly he did it in the bushes. It was the raw sex of it: the sense of taboo and sneakiness. Don’t worry, I’m not into teenage boys, I just love the imperativeness men have when they need to come.
The email date:
It went really well! It occurred to me as I sat down at my computer, that it would be easier to instant message from my desktop. Duh. I rarely give out my phone number, but my instant message has no real information (it’s under one of my many fake names), and I’m never signed on. So we did that.
The session wasn’t very long. The exchange became sexual within no time at all. Not my typical sexting—which I usually only do with guys I’m interested in—but similar. Enough so, that it was clear he wanted to use this as a way to get off. Not unholy surprising, but surprisingly easy. With the exception of “The Unicorn” I never sext with clients. They get me in person, that’s what they pay for. Anyway, soon after his long email, he sent me a jackoff video (which I had solicited). The video also turned me on. Which is odd, because he’s not my type and his dick isn’t big, but the angle was good (head on and close up). He came pretty fast—he didn’t even look fully erect—he sort of just milked the jizz out. And it spilled, rather than shoot. It was different than most of the jack video’s I see. I think the fact that it was so non-porno is what excited me. I told him I liked it while we messaged.
It wasn’t difficult to inspire him to come. I didn’t make anything up either. My perverted mind was enough. Money well spent…and earned! I could do that all day. Other than the non-cash issue, it was pretty fucking fantastic. “PayPal” and I have direct messaged on Instagram a couple times since that date. I told him what I specifically liked about his video, and also described my fantasy about men jacking off at work. I love the thought of a man getting so turned on that the only way to make his cock go down is if he comes. So, it’s him being stealthy—prison-style in the bathroom—and the urgency factor that turn me on. PayPal liked hearing about my fantasy and said he would do that for me when he could. I also love knowing that men, and especially married men, are secretly jacking off. Hiding it from their spouses. It’s in my wheelhouse of taboo turn-on’s. Sorry gals, I promise I’m not trying to come between you and your husbands. I don’t think cheating is ideal, but jacking off? Fair game. In the scheme of life and reality, it could be worse. Granted I’m not married, but no one has control over whom we think of. It astounds me when wives don’t think (or assume) their husbands jack off. Most men need to come. It’s as simple as that.
During this direct message, I said I was being a bad businesswoman (letting my inner slut get the best of me), and that these conversations should be saved for our paid online dates. He was understanding and said he wanted to book another session in a week or so. I’m excited about this new venture. In fact, it’s a no-brainer. I have an adventurously perverted mind and I don’t judge. People have asked me about Internet sex work before, but I don’t allow video or images of myself that I haven’t taken, but written sex-change and watching men come for money? I’m in!