Chapter 1 - Joining an Escort Agency
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Ever since I gave up my virginity almost six years ago I've had sex with a lot of guys in a wide range of situations. As varied as they may have seemed at first glance, until recently there was one thing that they all had in common. Either I knew who my partner were or at least someone I knew also knew who he was. In all that time I'd never gone out alone with some stranger just to have sex. When it comes right down to it, it wasn't so much that I didn't want to or was afraid of it, the opportunity just never came around.
Going to a strict religious school where any form of sexually-related conduct was forbidden had proven harder than I'd expected when I signed up. My freshman year turned out to be not so bad once I discovered that my roomie was bisexual. Unfortunately her parents decided to save some money so she was living at home our sophomore year leaving me with nice, but very virginal, new roomie.
Although there were some times during Thanksgiving and Christmas breaks when I was lucky enough to go home and enjoy myself, there were only a few other times that I was able to have sex with someone. Needless to say having been accustomed to having sex on an almost daily basis it was not easy for me to accept this sexless situation. When I was horny it didn't matter that I "knew what I was getting into." It's easy to think you can do something but sometimes putting it into practice can be a lot tougher.
In a recent diary entry about my first bachelor party I explained a lot more about all of this so I won't repeat everything here. Bottom line is I got to the point where I had to do something about the insatiable cravings growing within me or die of horniness. Well, maybe I wouldn't have physically died but it would've been a welcome respite!
What I DID do was to apply for a position at an escort agency and it wasn't long before I was the entertainment at my first bachelor party. I can't tell you how nervous I was before it started but it turned out to be an incredible experience! Having a room filled with horny men all staring at me with pure lust in their eyes and raging hard-ons was one of the most erotic things I've ever experienced!
Since I first noticed it happening as I was growing up, I've always loved it when I saw men looking at me like they want me, when they openly show signs that they desire my body and are willing to do just about anything just to see me naked let alone touch me - or do more. To have a whole roomful of them all at one time, and then to be fucked by each one in front of the others regardless of their age or marital status, was enough to make me cum over and over again.
After the complete success of that night, I was ready for more and tonight was going to be another first for me - being an escort for a total stranger.
One of the first things I learned was that there are some pretty strict rules if you're going to be in the escort business, at least if you're part of one of the legitimate agencies that's not serving as a front to a prostitution ring. First and foremost, such agencies do NOT sell or promote sex. They only arrange for a man to hire the services of a girl for a date - be it dinner, a movie, show, or business affair. Supposedly they check out the guys to be sure they're not felons or wanted by any police agencies or listed on any sex-offender lists. The main point again being that they are a legitimate service and not a pimping agency. If a guy just wants a hooker then he can cruise High Street in Columbus and take his chances.
Payment terms were something new for me as well. At my agency the client paid the agency directly for the evening so I never had to deal with cash or credit cards. This also had the added benefit of provided me with protection against prostitution charges as I wasn't handling money. I was paid by check twice a month just like any other job, paying taxes and all!
The agency also provided for my transportation each way in the form of a taxi that picked me up at school, dropped me off at the arranged location, and then was always available on a moment's notice to take me back whenever I called.
Of course, all that was said with a wink and a smile. During my indoctrination I was warned that most men would ask if I was available for additional "services". You can probably guess what such services consist of. The agency's official policy was that anything I arranged with a client AFTER the date was entirely my business AND my responsibility. It was up to me to establish what, if any, "tip" I wanted if I decided to go beyond the standard "date" rules.
Even though I knew this all up front, I still couldn't help but wonder just how it would all go in actual practice. One thing that made me feel better was that I was able to have a say regarding the guys I would meet. When I filled out my profile I limited myself from the start to only married men over forty, preferable with a family, and they had to be from out of state.
Yes, there was a method to my madness. Older guys had always treated me well. I figured married men would be more discreet and less likely to have STDs. As for being from out of state, I hoped that would keep them from any expectations that they might meet with me again afterwards.
Finally, I also set a strict rule that only one date per guy - no repeats. Unlike most of the whores I met at the training class who were plainly in it for the money, I was doing this for fun and so I wanted variety over quantity. Plus, I didn't want there to be any chance that someone would think we were starting to form any type of "relationship".
Chapter 2 - Getting Ready
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The agency must have had a lot of guys applying because despite my tight restrictions it wasn't long before I was getting numerous e-mails from the agency regarding potential clients. One guy caught my eye right away. He looked pretty handsome and had written a clever and entertaining introduction. He was from Chicago but what caught my eye was that he'd always been married to the same woman and even had two daughters, the oldest who was my age. He seemed to be the right one to start with so I replied to the e-mail and soon received a confirmation for the upcoming Friday.
For the rest of the week all I could think about was my upcoming "date". I had been on blind dates before and I knew most guys expected to have sex so that wasn't the issue. The difference here was that nobody had ever paid me to go on a date with them which put everything in a while new light. On a blind date, if I didn't like the guy I didn't even have to leave my house with him. In this case I was being paid to at least have dinner with the guy, no matter who he turned out to be.
I had never been this nervous before a date before! The night before I could barely sleep wondering what else he would want to do beside just have dinner. At the same time I was getting hornier each day wondering the same thing. The fact that I had no idea what he might want to do with me was exciting. Would he want just a hand job in the restaurant? A blowjob in the car? Would he take me to his hotel room? Would he want it rough or gentle? What if he was into something kinky? The possibilities were endless and I masturbated several times a day thinking of a different scenario each time.
