It's hard to believe I've been working as an escort for a whole year. I'm glad to say that, even during a slow week, I nearly always make $3000. I've made as much as $7000 quite often and $10,000 a few times. I was started in the business by my former boss arranging dates for cash, usually with clients of his law office. Up to now, my dates have been from him or by word of mouth from those people. But I'm thinking I need to start marketing myself in order to work to the next level.
I still live with my boyfriend. Things are fairly strained, it's true. I did tell him, after doing bookings for a few weeks, what my work now entails. He is not happy with that. The thing is, I don't want us to break up but I also know that my chief assets are my body and my sex appeal. I believe strongly I have to capitalize on those while I still have them.
So, I've paid image consultants for advise on walking, talking, speaking, dressing and makeup. I'm adhering to a rigorous fitness routine. I read insatiably on subjects an upscale man might be interested in. I'm going to place ads in places where those men will be likely to look -- 'Experience discrete companionship. View my photos and videos on Facebook...' or whichever site. I have a portfolio of professionally done photos and videos ready.
In the meantime, my boss Sydney still sets up dates. Lately he has asked me a couple of times if I will have sex with a man while he watches. I've been reluctant to agree but I decide to ask what exactly he wishes to see. Me sucking a cock and being fucked is the response. Big surprise. I agree to do it for $1000.
It's a bit risky but I also agree to do it at Sydney's home. His family is away so he's a temporary bachelor. But I employ my own part-time driver/body guard for my dates now. I can alert him if things go badly south.
I arrive at Sydney's rather grandiose house and am led to a living room. The date is already waiting. There is a sofa and chairs around a large and expensive looking oriental rug. On the carpet is a mattress covered in soft cotton sheeting. Sydney has what appears to be a double whiskey, the date has some mixed drink. I decline the drink offer. Before we begin, Sydney makes another request.
"I'd very much like to take some digital photos of what happens. "I have a mask here that will hide your identity. You will remain anonymous and I will pay an additional $1000."
He's holding a thin batgirl mask that will cover almost half my face and my hairline. Obviously, he knows who I am, so if he wanted to out me it would be easy. But a casual viewer won't recognize me. I'm concerned about him posting images of me but I insist on seeing all of them when we're finished, to delete the ones I don't like. We agree and Sydney hands an envelope with cash. My driver has accompanied me inside but I give him the envelope and he leaves, leaving the front door unlocked.
Time for the sex part. The date stands up facing me as I kneel on the mattress. The boss already has his Nikon ready. I unzip the trousers and allow them to drop to the floor. Immediately, I take his dick in my mouth, all the way to the back of the throat. I hold that position so Sydney can get a good shot. Then, I begin running it in and out while sucking gently.
This continues for maybe four minutes. I glance at Sydney, who is busy snapping away, and see he might be more excited than the man I'm blowing. I crouch my body lower to angle my neck, making it easier to swallow the entire cock. Again, I hold for the camera and do some gag and cough action, too. But I pull away when it's clear that he's too close to ejaculation.
The date guy steps out of his trousers as I undress. He plays with my breasts as Sydney takes some close-ups. Then, I guide him to the bed and onto his back. Making sure the condom is secure, I straddle his body to ease myself down onto his stiff penis. I ride him gently to prevent any premature shooting.
After another few minutes, we go to the missionary position. He is thrusting fast now. I almost burst out laughing as he bucks away and makes the funniest moaning sounds. I keep my composure, though. Shortly, he comes and I pull him down to wait for him to finish. When I'm sure it's over, I roll from under him, sit up and smile at the camera.
My date hurries off to the bathroom with the condom dangling. Sydney asks if he can take some solo nude shots of me in the mask. For the thousand, I suppose he's entitled to that. I just go to another bathroom to clean up some and freshen my lipstick. Sydney takes another fifty or so shots. When I'm dressed again and the camera is put away, I remove the mask and thank both the men. My driver drops me at home.
My boyfriend is asleep when I arrive but the next morning, he sits me down for a talk. The gist is, he's done. I can't say I'm surprised. I don't have a problem with what I do but he does. And I realize most any guy would. But I'm planning to move up in my escort work not give it up. It's also consuming more of my time as I become increasingly successful. So, we separate amicably. I decide it's best if I move out. That afternoon I start apartment hunting.
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