Spring Break is a huge time for all college students, with may flying off to hedonistic spots in Florida, California and Mexico. I believe it or not had money to do something, but had no friends or desire to travel to one of these spots. My school work was all caught up, as most professors made sure that all assignments were due before this week, and were kind enough not to schedule anything due the following week.
I took a few days to rest up, my last assignment had really worn me out. If I had not been 18 at the time and able to bounce back after only a moments rest, I would have never made it through all three "films". Kevin had not called during the beginning of the week, so on Wednesday I called him to see if he had any assignments. I was told no, not at that time, but that he would work on trying to get me something for later in the week or the weekend. Now I knew that Kevin was driven by money, and I had a sneaking suspicion that he was making as much or even more than I for each of my assignments.
I was a little disappointed, but did my best not to come across that way over the phone. I was horny actually, that is what was driving my desire to "work". It was mid-morning by now, and I needed something to do. I went to the grocery store and purchased a number of items from the produce section, most of which would be going straight into the garbage when I got back to my room, but I did not want to just walk in and purchase a cucumber.
As soon as I returned to my room, my clothes left my body, and I jumped on my bed. I took out a condom and rolled it onto the cucumber. I used the cucumber to penetrate myself, it went in with no trouble, and really felt good. I held it in for a while, then began to slowly moving it in and out with one hand, while stroking my cock with the other. I came, but was still horny, so I moved my self activity's into the bathroom. I had to pee, and just then got this nasty idea. I climbed into my tub and laid down, and shot my urine up towards my head. I could feel the warmth of my piss as it hit my body. I then strained to arch my body and position my head so that a powerful stream flew up and hit me in the mouth. I opened my mouth for some reason, but it tasted horrible, so I just let the rest hit my body.
God this felt so nasty, that I masturbated myself silly while taking a shower to clean up. In less than a half hour, I had brought myself off three times. My cock was sore at this point, so I finally decided to leave myself alone for a while. That ended anything of note for that day.
My prayers were answered the next morning, when I was woken up by a call from Kevin. Another one of his models had to cancel out on an assignment, so he was offering it to me. I said yes without hearing what it was, immediately Kevin backtracked and told me that this one particular model would sometimes dress up in drag and that the client had a thing for transsexuals. Well I had never done anything like this, plus I did no own a dress or makeup or a wig, you name it. Kevin told me that if I took the assignment that he would take care of everything, including transportation, and I would be paid $ 1,000 for just over an hours work. I agreed once again.
This was something new and I was not sure what I felt about it, but I had materialized into some who was willing to try anything once. Kevin arrived and had a bag with him, he spread it all out on my bed. There was a woman's thong, a bra with false breasts that would make it look like I had breasts. The dress was a small red one that barely covered my ass. Kevin had a blonde wig, lipstick and makeup too. The shoes were the last thing that I saw, they were a pair of slut pumps I guess you could call them.
I was going to get dressed, when Kevin told me that I had to first get ready. He had me go into the bathroom and get into the shower. I had to shave my face, all the hair off my legs, under my underarms and all the hair from around my cock. I used some hair removal to help expedite in the process.
