tagGay MalePutting Myself Through College Ch. 05

Putting Myself Through College Ch. 05


I did not work the next week, I was able to focus all of my efforts on school. Kevin called me on Thursday to see if I wanted an assignment for Saturday, I said yes. Thanks to this job, I had been able to save over $ 5,000 at this point. Kevin told me that the assignment would be a "modeling" project for a much older man. I asked him for more details and was told that a wealth older gentleman in his late 70's had dropped by his office and was very excited after seeing my pictures. He wanted me to model for him, and maybe something else as well. The job paid $ 2,000 for the afternoon, I could tell that Kevin had taken him for more money than usual, as my normal fee for that amount of time would have been $ 1,500.

I was told that the man's name was Mr. Phillips, and was given his address, it was a very large condo in the city. I arrived that Saturday afternoon and was shocked by what awaited me. Mr. Phillips was in his late 70's for sure, in fact he looked like he was even older. He was very nice, and explained to me that he wanted me to model for him, I saw a brand new ultra expensive camera and close to a dozen roles of film. I questioned since it was not digital, he told me not to worry it was for his private collection only.

I removed my clothes and modeled on a chair for one roll, then on a couch for a second. We moved into his kitchen area, and I smeared some chocolate syrup on myself as he shot a third and forth roll. His balcony was next, I was nervous about being seen nude outside, but it was what Mr. Phillips wanted. He must have really enjoyed the scenery as he shot at least 3 rolls out there. Finally we moved to his bedroom and he had me lie on his bed as he shot another roll. For the money he must have spent on that camera, he could have purchased a digital one which could have taken several hundred pictures before he would have to upload them.

Mr. Phillips ended our photo shoot by having me roll my body upside down and masturbate with my cock lined up with my face. I did this until I was about to cum, and Mr. Phillips asked me to keep my mouth opened he wanted to see it fall in. I did as he snapped away, and before long, my warm cum was spurting out of my cock, falling into my mouth. I was instructed not to swallow or spit it out. He took several close ups, then requested that I swallow, which I did despite the fact that I really did not like my own taste.

Once our modeling session was over, I had been there about an hour and a half. I asked Mr. Phillips if he wanted anything more. He put his camera gear away and then took off his clothes. His body was not a pretty site, and thankfully he did not want oral sex. He had me bend over, and he spent several minutes trying to maintain an erection and get it inside of me. He finally achieved his goal, and started to fuck me. Surprisingly his cock must have found some life, as I found it to be enjoyable (as long as I was not looking at him). He lasted longer that I had expected, and finally came shooting a few spurts into me.

He was spent after that, but did request that I masturbate for him once again. I did so, and he even reached out and took over for a while. I came all over my stomach, and he stuck out his fingers to scoop some of it up. He tasted me and said that I must have really enjoyed the way he ended the modeling session, if he only knew, different tastes for different people I guess. My time with Mr. Phillips ended at this point, just over two hours, not bad at $ 1K per hour I thought.

On my way home, I discovered a voicemail from Kevin. He told me that if I was up to it, he had another assignment for that night, a last minute assignment, which would pay the normal $ 1,500 for the evening. I agreed and was told to come to his office that night at 6pm, and that the client would pick me up there. I headed home and showered quickly, I had very little time to clean up, change and get back to Kevin's office. I wore a dress shirt, black dress pants and a tie for that evening.

I arrived at Kevin's office just before six, I could tell that he was happy to see me, as he made a comment that I had just made it. Kevin filled me in on the night ahead, a Mr. Cheek was picking me up in a limo, and that we would drive around the city and the surrounding areas for the evening. Mr. Cheek I was told was a Vice President in a publicly traded pharmaceutical company.

A stretched limo arrived a few minutes later, and a chauffeur got out and opened the door for me. Once inside I could not believe my eyes, the back of the limo was huge, with two very large leather seats, each the size of a couch. There was fully stocked bar, and a large screen television. Mr. Cheek greeted me and asked if I was up for a night of adventure. I said yes sir, then he used an intercom to tell his driver to take off, then I noticed that he turned the unit off. I inquired about privacy, and he told me that the driver could not see or hear anything that went on in the back.

We drove for a few minutes as he opened up a bottle of champagne, he offered me a glass. I really did not like the taste, but I knew not to insult the client, so I quickly drank the entire glass. This only resulted in Mr. Cheek refilling my glass, as he filled one for himself. We toasted a wonderful evening, then talked for a while. I was told that we would drive around for several hours, then we would be going to the west of the city, out towards the mountains, as he loved the scenery. It was getting dark, so why did that matter I wondered?

Mr. Cheek finished a drink, then another, my stomach was not responding well to my first glass, so I only sipped at the refill. He took our glasses away, and started to unbuckle my belt. Soon my pants were off, in fact everything I had on below the waist was on the floor of the limo. Mr. Cheek stood up and lowered his pants, and displayed his cock to me. He talked about its size, 8 inches, and had me bring it to life with my hands. I came to life at the same time, Mr. Cheek was happy to see that, before once again pointing out his size and he enjoyed the fact that he had me beat by a few inches.

I was ordered to suck his cock then, as he said, "well you brought it to life, now go to work". I did as instructed and took him into my mouth. As I sucked him in, he picked up his drink again and emptied the glass. He was in a good mood, he must have had a few drinks prior to picking me up. I worked his cock in and out of my mouth, spending time on the tip, then the shaft. I removed him to work on his balls, and tried some other things, but to my surprise he was not really paying attention. His cock on the other hand was responding.

I did not bring him off, as he removed his tool from my mouth and ordered me to finish undressing. He then tackled me back into the seat and immediately lined up his cock with my anal entrance. He poured some champagne on his cock, which did little to grease it up, then pushed into me with great force. Once again I found myself squirming at the assault of a client. He worked himself all the way in, in no time at all. I guess that football party had loosened me up a little as it did not hurt too much to take him in so quickly.

Mr. Cheek fucked me for a long while, he must have been on something, as his attack did not seem close to finishing. After what seemed like an eternity, he pulled out and came all over me. He then gave me the instruction that I was his cum slut, and that I was not to wipe anything off myself.

While this was going on, I did not realize that the limo had stopped moving. I only became aware of this when the driver opened the door and joined us. Mr. Cheek told him to strip and he did, exposing a rock hard 7 plus inches, just slightly shorter than Mr. Cheek. He is all yours Mr. Cheek said to the driver, he immediately replaced Mr. Cheek inside of me and fucked me hard for several minutes. I think that he was going to cum inside of me, but Mr. Cheek yelled and at the last minute he too pulled out and sprayed me with his cum.

The driver then exited the back and started up the limo again. Mr. Cheek ordered me to get up so that he could sit down, once he was comfortable, he ordered me to drop to my knees and work on his cock again. I did as I was instructed, this time to my delight, he actually seemed to enjoy my labor. I sucked on him for a while, but again he was not close to finishing. He stopped me and then reached into a bag and pulled out what I instantly knew was drug paraphernalia. He then produced a white powdery substance and started to snort it. I just kept concentrating on sucking his cock, but he did not cum.

A few minutes later, he was acting crazy. He tried to get me to use some, but refused. Mr. Cheek just laughed. Then removed his cock from my mouth and ordered me down onto my hands and knees. Mr. Cheek entered me immediately and started to pound me really hard. His hands then went around my neck and he started to chock me, I moved immediately as I was starting to get really freaked out. He then pinned me under him and entered me again. He left my throat alone this time and fucked me until he deposited another load on to my chest.

I was a mess by now, this was not turning into a good night after all. The limo had stopped once again, and the driver opened the door, and Mr. Cheek said that we would be getting out here. We were in the middle of the woods somewhere, and Mr. Cheek had be get up onto the hood. His driver fucked me again, with the same result. By now Mr. Cheek was really high, and he ordered his driver to get him a spoon. He used it to scoop up what he could off of my body, most of the earlier portions had run off or dried up thankfully. He then placed the spoon up to my mouth and ordered me to eat it. I had no choice so I did so. Mr. Cheek then grabbed me off of the hood, and he and his driver pinned me to the group. Mr. Cheek took me once again in the ass, as his driver stood over me and lowered his cock into my mouth. I was a mess by now, just trying to keep up with the action. I am sure that the drugs were driving Mr. Cheek most people would have been exhausted by now.

This went on for over 10 minutes until I could take no more, I tried to get up, when Mr. Cheek struck me very hard. This must have turned him on, as he hit me some more, but he did come once again. His driver then removed his cock from my mouth and entered me to finish. Once the driver had finished again, he picked me up and threw me back into the limo. Mr. Cheek followed me in and actually worked the spoon into my ass, to scoop their cum out of me. I had to eat a second spoon full, as Mr. Cheek berated me to no end.

Thankfully the driver was on his way back to the city, and Mr. Cheek turned his attention to his drugs. I was left alone for about an hour, then just before we reached Kevin's office, Mr. Cheek attacked me again. He slapped me, then grabbed me by the throat and spit in my face. I felt humiliated and scared for my life. He produced a dildo and shoved it up my ass, he then fucked me with it was quite a while, slapping me intermittently and insulting me. He finally ended his assault and removed the dildo from my ass. The limo stopped, and I thought that we had made it back to Kevin's office and I was finally saved. Unfortunately, the door opened and two young men entered, both in their early 20's. Mr. Cheek introduced them as his nephews, but I doubt they were. They both started to take some of Mr. Cheek's drugs and then he directed their attention to me.

They pulled me down on the floor, and turned me over onto my stomach. I knew what was coming next, as one shoved his penis into my mouth and the other entered my ass. They fucked me for a while, both had strong grips on me. Finally the one who was in my ass pulled out. He then lied down on his back and his friend pulled out of my mouth, just long enough to move me on top of his friend. I sat down upon the first guy, sinking down on his cock, this was a position that I had never tried before. The other guy was back in my face in no time, shoving his cock back into me mouth. They started to fuck me again when Mr. Cheek offered me something that would help me relax, I again declined, but I was soon wishing that I had.

Mr. Cheek then approached me from behind and I soon understood why the young men switched places. I tried to push Mr. Cheek away, but I was over powered. Mr. Cheek then tried to force his cock into my ass. There was no way I could take two in me at once, I would have been ripped apart. It really hurt as he tried and tried, but I was not big enough to accept him. Luckily the young man inside of me came, he exited and Mr. Cheek entered me once more. The guy who was assaulting my mouth, suddenly finished as well, would my face on his cock so that I had to swallow his entire load. Mr. Cheek fucked me as hard as he could this time, yelling at me for not taking two cocks in my ass at once.

By this time we had reached Kevin's office and the driver had once again joined us. Mr. Cheek finished, allowing the young man I was sitting on, to get up. The four of them stood around me as I could not stand. Mr. Cheek poured four glasses of champagne, and then the four of them toasted me. Then without warning, they spit or pour what they did not finish with the toast, all over me. I was then allowed to dress and leave the limo, I was a complete mess.

It was dark out by then and I tried to call Kevin, I wanted a ride home, I looked a mess and did not want to use public transportation. Kevin did not answer, so I was forced to walk several blocks to get the train. I made sure to stand far away from the few down who were underground waiting for its arrival. I got on the last car, but since there were only three that time a night, I could not avoid everyone. I sat with my head held down for the entire trip, I know that some people were talking about me, but I would not given them the pleasure of acknowledging them. I got off at the stop before mine, and walked too far to get home. Luckily by the time I reached my room, it was well after midnight and everything was dark and quiet. I was happy that I had a private entrance.

I felt terrible; I had been abused, humiliated and embarrassed. I immediately took a shower and then went to bed. Unfortunately I could not sleep, and I lied awake most of the night. The next morning I called Kevin, I was very tired and was not in a good mood. I spoke to him about the night before, and he said that he was sorry, and then proceeded to convince me that it was nothing to worry about and that I would enjoy my next assignment a lot better.

Kevin drove over to pay me that morning, and as if it was an after thought, he mentioned that he had an assignment for me that day. I was in no shape for an assignment, and I needed to rest as I was dead on my feet, but somehow Kevin convinced me as it was only a short one hour job.

That afternoon I went to the house of a Mr. Smith (not his real name, but as I was learning, most wanted to keep their identities private), and he invited me in. I was on autopilot and I think it showed. I got undressed immediately and got down on my knees. He had not even asked me to do anything, and I was already trying to get him out of his pants. I took his cock in my mouth and started to really punish it, I am not sure why, but I was sucking it in for all I was worth. Mr. Smith loved this and I could hear him moan. He soon shot everything he had down my throat. I just got up and waited for his next instructions.

Mr. Smith was confused by my actions, and I forget exactly what I said, but he then had me follow him into his garage. He took my arms and tied each above me and then pushed me forward a bit. He explained that he had watched a scene in a movie where a guy did something similar to a young man that he raped. When I looked at him, he quickly assured me that he was not going to do anything to hurt me, that was a welcomed acclamation after what had happened the night before.

Mr. Smith produced several dildos and took turns insert one after another into me, they were getting larger each time. He did this for a while, then left a large on inside of me, as he walked around in front of me and smoked a cigarette as he spoke to me. Mr. Smith must have been repeating what he had heard in the movie line for line. Once he had finished he dropped the cigarette to the floor, blew smoke in my face and then walked around behind me. Mr. Smith removed the large dildo, and I almost did not feel it when he replaced it with his smaller cock. Mr. Smith grabbed a hold of my shoulders as he plowed into me. He was really trying to hurt me I thought, trying to shove his cock through my ass and have it come out of my mouth. His thrusts soon slowed down and then his body slammed into mind as he gripped me really tight and came hard into my ass.

He left me and then sat down for a while, catching his breath and watching me hanging there. He threatened to keep me there forever and some other shit, again it sounded like a crappy movie script. Soon though he did release me, and then started to act normal again. He thanked me for my services and said that he was happy that I had no problem going alone with his fantasy.

I left to head home, and was not half a block away from Mr. Smith's home when Kevin called. He told me that Mr. Smith was a new client and that he just wanted to check up on me. I told him that I was fine and Kevin said that he would meet me later in the week to pay me.

This is the end of part 5. Please e-mail me with your thoughts. Did you like the more extreme experiences? Would you like more, or should they be more tender and loving? Thanks RobXXX

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