Putting Myself Through College Ch. 08

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.

Finally I put everything on, and Kevin did my lipstick and makeup like a pro. He also helped me put on temporary fake fingernails, then Kevin painted them as well as my toenails. It hit me, I could not be seen walking out like this. Thankfully Kevin had with him a long trench coat, it was too big for me, but it worked as I walked barefoot to the car.

I was driven to the man's home by Kevin, and when we arrived, Kevin phoned him and he opened his garage for us to drive into. I immediately put on my shoes, the wig and took off the coat. Kevin got out first and made a big production in opening the door for the nice young lady.

I was greeted by my client, a nice older man, somewhere in his late 40's. I was not given his name, and when I said "Thank you Mr.?" after his greeting, he did not offer his name. I know that some clients take the privacy very seriously, but when you have models escorted to your home, it kind of takes the anonymity out of the picture. While I waited, Kevin told him that he would be back to pick me up in an hour.

Kevin left and I was escorted into the gentleman's home, he wasted no time in lifting up the back of my dress and squeezing my ass. I was led to his bedroom, and he lifted my dress from behind and moved my thong to one side. He told me that he just loved fresh young pussy, then he buried his tongue into my ass. I squirmed around in his grasp, as he buried his tongue into me. He loved my reaction, as he commented on it several times. He then backed away and told me to turn around.

He looked at me, then bent forward and kissed me passionately on the lips, eventually forcing his tongue into my mouth. I kissed back as he wanted, until he broke our kiss, stood back and smacked me across the face, calling me a filthy little slut. The client then took his cock out and shoved it into my mouth very hard. I started to gage, and had trouble keeping up with his assault. He would pull it out long enough to see the rings from my lipstick on his cock, then would shove it back in even harder.

I was yelled at and told to relax, that he wanted me to deep throat him. This was an act that I had in no way came near to mastering, but this man insisted, and eventually he worked his cock in to his liking, I had to concentrate very hard to be able to breath through my nose. Suddenly he came with a super fast explosion, shooting about 9 or 10 streams into the back of my mouth. He held my mouth closed around his cock until I swallowed.

"Good girl" he said to me, "I will make a nice little cocksucker out of you yet". He then had me get up on the bed and he removed my thong entirely. His fingers pocked me hard, until he had penetrated me dry, it hurt and I tried to move away. He saw this and then "let" me suck on his fingers, I had to taste my own ass. I did suck on them, coating them with as much saliva as I could. When his fingers pushed into me again, lucky I did not feel the discomfort of the first time.

I was then forcibly thrown over his lap, as he said what is this, referring to my cock. He yelled at me for having a "hard clitoris". Reaching down he grabbed a pair of slippers lying next to his bed, and spanked me with them as hard as he could. I could feel his cock harder during this time, and before I knew it, I was being thrown back down on the bed.

Without warning I felt his cock enter me, it hurt, as he had not lubed it before he began. He withdrew and turned me over to face him. He went to fuck me again, when I got upset over my cock being hard. He slapped me a few more times, then started to rough me up beyond a playful nature. I put up my hands to defend myself, when he struck me with a shot that knocked all of the air out of me. His roughing up worked, as my cock had deflated during this time, as I had tears in my eyes. This really turned him on, and then he shoved his cock back into me, and was chocking me as he was fucking the ever living hell out of me. I was really scared at this point, this nightmare of a man wanted to kill me I thought.

I did survive, as he came in no time, driven by his violent sexual rage. After that he became nicer to me, spending time by letting his hands roam around my body, feeling up my ass, tits and legs. He then sucked on my painted toes for a while. Just before our hour was up, he ordered me to strip out of my clothing and take my shoes off. I was now back to being just a nude 18 year old man/boy. He finally grabbed some lube, yet it was not for his penis. He rubbed it generously over the heels of the shoes that I had been wearing, then inserted one shoe into me. He kept pushing it in and out, thankfully he was very gentle while doing so. The client masturbated himself at the same time, he the shot his cum into my mouth, as he had grabbed me by the throat just as he was to finish.

The client backed away, I spit his spunk out of my mouth into a nearby wastepaper basket. The time was up and I quickly tried to gather my things to leave. This man must have been a regular, because when Kevin arrived they talked very nicely to one another, and Kevin would not acknowledge me when I tried to tell him what had happened.

I drove home with Kevin, wearing only the trench coat. He helped me inside, then told me that he would help me clean up. I put everything into a trash bag, and told him that I did not want to do that again, I enjoyed it much more being a man. Kevin had some products that helped immediately remove the fake nails and the polish off of my toes. He said that he would dispose of everything, and I thought that he was leaving after giving me money, so I headed to the shower.

Just as the hot water was taking it effect, relaxing me, I heard my door open and in walked Kevin naked. He joined me in the shower, and started to stroke my cock. I enjoyed the hand job, he kept it up until I had finished. Kevin then took the soap and lathered up his cock, while turning me around. He did not ask, he just fucked me like I was his little bitch. I would have enjoyed this, if it was not for the discomfort that I was still feeling from earlier. I pushed my ass back to Kevin, matching every pump, this worked and he came in minutes. Kevin pulled out, washed his cock, then without even saying goodbye just left.

I sunk down to my knees and left the water hit me, trying to gather myself. I finished my shower, then went to the sink to make sure that I had removed all traces of makeup. After that I called it a day, $ 1,000 richer, but a million dollars wise, I was no tranny.

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This is the end of Part 8, please e-mail me with your thoughts, and if you want to see more. Thanks RobXXX