Chapter 1: My Escorting Resume

In my diary entries about my first bachelor party and two escorting jobs I explained in detail how and why I got into the escort business. Briefly, I attend a very strict religious university and during the second semester of my sophomore year I was becoming depressed from the lack of sex to the point where it was beginning to affect my schoolwork. Given the small size of the community and the nature of our campus, doing anyone at school to the extent I needed it was not an option so I looked into a few escorting agencies to see what they had to offer.

Eventually I signed up with the one that seemed to be the best and soon started out my new “career” with a crazy bachelor party and then moved into personal escorting (alright, maybe a fancy name for being a whore but I wasn’t streetwalking). The first two time with “customers” went so well that I would have done them for free to be honest. I had established a rather narrow profile with my agency of men I was willing to escort which limited my opportunities quite a bit but nothing I can’t live without. I only wanted to fuck married men around forty or older, preferable from out of state with a family.

Now I am sure you’re wondering why I wanted someone like this instead of some young stud who could fuck my brains out all night. If I was at a party maybe that would be who I would be drawn to. In this case I was escorting so I wanted to be more careful. My experiences with older guys have shown me that they generally appreciate me more and treat me better than the young guys who just want another notch in their belt.

As for wanting them to be married, I hoped that this would help to ensure discretion on their part plus it turns me on something fierce knowing a man wants me bad enough to risk his marriage just to have me for a few hours. The out of state requirement is so they won’t try contacting me afterwards even though they have no idea who I really am other than what I tell them.

Finally, I also established a strict rule of only one date per guy - no repeats under any circumstances. I was only doing this for fun and I wanted variety. I also didn’t want there to be even a remote chance that some poor guy would think I actually cared about him and think we were forming any type of “relationship”.

My first “job” was a bachelor party which turned out to be one of the most exciting events of my life. It’s hard to express the thrill I got from having ten guys horny lusting for me, all of them wanting me in the worst way, including the groom. Well I can tell you that it was a tremendous ego booster! I wound up doing more than just stripping - a LOT more.

Greg was my first escort. He had looked handsome in his profile picture and had written a clever and entertaining introduction. He was from Chicago but what caught my eye was that he had always been married to the same woman, like my dad. It turned out that he even had a daughter my age and a hidden desire to have sex with her so I became his “daughter” for the evening. The success of that night was enough to convince me to continue on with my escort career.

My second escort was John who was 45. He had been married to his wife for ten years yet had four children, three by previous marriages and a fifteen year old boy with his current wife (not a typo, the son was fifteen and John had been married ten years after having been divorced for one year - you do the math). He wasn’t the poster child for marital stability, that was for sure! What drew me to him and agree to meet was his witty profile.

John met me at a GameWorks after which we went to his room in a nearby Hilton. What made it really hot for me though was he talked to his wife on the phone almost the entire time he fucked me and she never had a clue what her husband was doing. I came so hard when he told her how much he missed and loved her when at the same time his cock was filling my cunt with cum!