Putting Myself Through College Ch. 03

After I was paid for my second assignment I enjoyed the next two days, peace & quiet, the calm before the storm so to say, with the spring semester at college coming right up. I took the time to really think about my sudden transformation for a scared 18 years old wondering how he could remain in college, to someone who had allowed himself to be used by two men for money (basically raped by one), and how I felt as if I was in a better place as a result. I guess the money, and the ability to pay my way, had made me feel like an adult for the first time in my life. I also came to the realization that I did not mind the sex, it was almost like a performance, and that I could careless what anyone thought at that point, my life was mine.

Wednesday morning I received a call from Kevin, he had an assignment for me that afternoon, a one hour quickie as he put it. I would be paid $ 500 for my time, if I was interested. I said yes. I was then given the number of a real estate agent named "Larry". I was to call Larry and request that he show me a vacant house. I took his number and did so, Larry made arrangements to meet me there at 2pm that afternoon.

Larry was a heavier set gentleman in his early 50's, he was obviously a real estate agent, and as he told me as we chatted on the phone during the arrangement that he was recently divorced. It was easy to see why when I meant Larry, one could obviously see that he had no interest in women. Larry and I went into the house and into an empty room that must have been the master bedroom. Larry quickly took off his shirt, his chest was hairy, a mix of black and gray. Larry then approached me and wanted to kiss me.

As we kissed, Larry brought my hands to his chest, so I started to rub him. At his direction I then started to play with and twist his nipples. He then guided my mouth to his nipples and I sucked them, a new thing for me. Then Larry took a step back and dropped to his knees, he unzipped my pants, lowering them to my ankles. Larry then reached into my underwear, and brought my cock out through the fly opening. He hungrily devoured my cock, he was not a handsome man, but his mouth sure felt good.

Larry sucked my cock for several minutes, and then brought his hands around to my ass. He took a finger and played with my ass, eventually working two into my ass. This had an effect, as I came into his mouth only moments after he had penetrated me. Larry played with my cum in his mouth for a minute, then he swallowed. Larry stood and kissed me again.

Larry then asked me to turn around and he lowered my underwear. He took his time to take off my pants and underwear all the way at this point. Larry then took his pants off, and asked me if he had excited me. I said yes, the answer I knew he wanted to hear, he then stepped up behind me. I looked back as Larry reached into his pocket and took out a very small vile of lube, his cock was not too big, in fact it was smaller than mine. It was a little thicker than mine though, so it actually did feel good when it penetrated me.

Larry then fucked me for just over a minute until he had cum inside my ass, well it was nice while it lasted. We then talked for a while, Larry was using his full hour. He told me that he had just sold a very expensive house and that I was a present that he was giving to himself. I could have gone home with him, he joked (a little too much), and I could tell this older man was desperate for male company.

With just about 20 minutes left, Larry asked me to fuck him, that he want to feel me inside of him. This was a first, up to now each man I had been with was a total top, Larry had performed oral sex on me and now wanted me to sodomize him. My cock came to attention, and I used some of his lube to get ready.

Larry laid down on his side, a different position, and I laid down on my side behind him and aligned my cock with his desperate opening. I had barely penetrated him when I could tell that he was going to town on his own tool. I worked my cock into his ass, then started to slowly pump in. It was a first for me, but the position was awkward on the carpeted floor. I picked up my pace and soon afterwards, Larry let out a moan, as he had finished his manual manipulation. Larry was then bringing his ass back to meet each one of my thrusts, this really made it feel good for me.

My thrusts became more harsher, which seemed to turn Larry on even more, as he pushed back even harder. I could take no more, I filled Larry's ass with my cum. Larry was like a woman in a porno movie, he was moaning as if he was having an earth shattering orgasm.

I took my cock out of his ass and Larry turned over and kissed me once more. He then rolled over on to me completely, almost crushing me with his weight as he was rubbing his body into mine. Larry finally stood up off of me, he then asked if he could keep my underwear, I said yes, Larry then took them and clean my cock with them.

We both dressed as Larry asked me to come home with him again, I laughed it off as a joke, but I could tell it was not. We parted as Larry told me that he would love to see me again. That was different, just a one hour sex session, straight and simple, but very enjoyable for me. I would learn to enjoy assignments like this, as versatile men are few and far between in this business.

I had no more walked in my door when Kevin was on the phone, telling me that Larry was happy, and asked if I would be interested in a second assignment that evening. I said yes, what did he had lined up. The man I was told was named "Mr. Smith". I was told that he was in his early 30's and that he had recently left the marines. It was another 1 hour assignment, and I would meet Mr. Smith at a motel room. This caused me some concern, but Kevin told me that Mr. Smith was a return client, so he felt that I was safe. Still a cheap motel room, that was for hookers, I did not consider myself in that order.

Mr. Smith meant me at his room, he was dressed just in a robe. He was a large man, about 6'4" and I asked, he said he was 260 lbs. He asked me to undress immediately, which I did with no fan fare. Mr. Smith picked me up and carried me to the bed. He opened his robe and my mouth fell open. His cock was huge, I mean it was the largest I had ever seen, it must have been 10 inches if not more.

Mr. Smith took my cock into his mouth, and worked me to an erection. He then grabbed a hold of my body and flipped me over, and picking me up in the process. My face was only inches from his cock, as mine was his. He took me back into his mouth, and I knew to do the same. It was difficult in that position to get him in, as my hands were around his waist trying to hold on (with the blood rushing into my head). I took as much of him as I could into my mouth, but did not really do too much.

Mr. Smith then put me back down onto the bed, my head was lying on the edge. He got over top of me, and pushed his cock back into my mouth, then drove it in like a piston. I was chocking instantly, but he just kept telling me to relax my throat. I almost vomited, in fact I believe I did so a little. This must have turned him on, as he pushed down really hard, and I felt him go down my throat. I thought at that moment that I was going to die by asphyxiation. Thankfully though he must have realized this as he pulled out, and I spent the next few moments regaining my breath.

Mr. Smith was now on the bed and he told me about some of his sexual exploits in the marines, I guess there were more than a "few good men" in his squad. Next he took out some lube and really put it on himself. He then lubed me up, working several fingers inside of me, he had large hands. He was pulling the walls of my opening for all he could, it hurt, but he said that I needed it in order to take his tool as I was small. He entered me with a sudden thrust and I almost blacked out. He brought his mouth down upon mine to muffle my screams, as he immediately assaulted my ass with the largest cock that would ever go in it. His was in very good shape and he lasted for what seemed like an eternity, the funny thing was by the time he had finished, I had actually began to enjoy it.

Mr. Smith was not done with my ass, he was a young man in excellent shape and he rebounded quickly. He fucked me twice more, we were soaked in sweat by the end of the hour, in fact I think we went a little over. When he finally took his cock out of my ass, I felt empty, no in fact it was even more than that. I could not walk for a couple of minutes, it was an entirely new experience. I called a cab, not caring how it appeared, and was driven home rather than walking several blocks to catch a bus.

I went in and collapsed on my bed and immediately fell to sleep, I did not shower and clean up until the next morning. Kevin called early and said that I could come by and pick up my money when ever I wanted that morning. I dressed and immediately headed to his office. When I arrived, he had a big smile on his face and gave me my $ 1,000 for the prior day's two assignments.

Kevin then asked me if I was available that day, I commented that he was keeping me very busy, he said that I was a very reliable person. I wondered to myself what his other "models" must have been like? He then told me that he had a special assignment if I wanted it, I asked him for the details. A gay couple was having an anniversary, and they wanted a threesome. I was intrigued and said yes. I was told it was for the evening and it would pay $ 1,500.

Just before I was ready to leave, Kevin asked me to model for him again, that he needed a few more pictures of me. I agreed, and quickly took my clothes off, thinking it would only take a minute. When I looked up, Kevin was fixing himself, and asked if I would mind proving myself to him. He told me that if I did, he would "trust" me with some real money making assignments. It actually excited me a little to know that Kevin wanted to fuck me.

I bent over Kevin's desk and he quickly inserted himself into me. This was a straight fuck, he was going to town, no kissing or caressing or even communication on any sort. Kevin came in my ass, and then collapsed on top of me. We remained in that position for a moment, then Kevin removed himself from me and said boy did my ass feel good around his cock. I cleaned up and went on my way, Kevin would make the arrangements with the couple and call me with the specifics in a few hours.

My instructions for that night were to go to the men's house, it was tucked away in the suburbs, in a nice development. I arrived at seven at evening and was greeted by Craig and Mike. Craig was in his early 40's he stood about 6'0 and Mike was in his mid 40's and was around 5'5". They asked me to enter their home, it was very nicely decorated, and extremely clean (I guess what they say is true).

We talked for a while, they offered me something to eat, which I politely declined and then we made our way into their bedroom. Mike and Craig undressed as did I, we did not talk during this time or do anything special. The two of them started to kiss and their hands were roaming over each others bodies, I was just standing there all alone for a while.

Finally the three of us climbed onto their bed and Mike laid down on his back, and Craig motioned for he and I to blow Mike. We passed his cock back and forth between out hungry mouths for a few minutes, then Craig move down to suck me. We continued to suck away, Mike in my mouth, and my tool in Craig's. Craig was a real master and I soon removed Mike from my mouth and told Craig that if he did not stop I would cum. He did not stop and sucked me down harder, until I came in his mouth. I then continued to work on Mike, until Craig move up and brought his cock to my face. Before I knew it I was sucked both them, taking turns with each. I actually tried to get both in my mouth at once, they appreciated my effort, but it was not really a successful one. Mike eventually grabbed a hold of me and used my mouth to finish himself. I then moved my attention to Craig until he filled my mouth as well.

While Craig was receiving my attention, Mike had picked up some restraints. Next thing I know I am tied down on the bed on my stomach. They then put a pillow under me to raise my ass, then each took a turn with me, until they had finished in my ass. Craig took a minute to rest as Mike grabbed something else out of their closet. It was a butt plug, and he plugged me so that I would not feel "empty" as they recovered.

Mike then produced a small whip and started to whip my ass, but not too hard. He told me he liked to play, but would not leave any marks. Craig joined in on the fun, as I was helpless to do anything else. Then punished me for about 10 minutes, doing more than just whipping my ass, Craig in fact started to fuck me with the plug.

Once they were ready for another round, and then untied me, and Mike entered Craig from behind. It looked really funny as they moved towards me slowly so that Mike did not come out of Craig's ass. Craig then entered me, and before I knew it, they were fucking in rhythm. This continued until both had finished. Mike then mounted me, and told me to stick my cock into Craig. We then fucked again, this time I was in the middle. My first sandwich, I totally new feeling, one I recommend if you ever get the opportunity.

This finished up our activities together that evening, as they were worn out and so was I. They asked me if I wanted anything to eat before I left, and this time I accepted. Mike was a good cook I found out. We ate and talked some more, then they thanked me for such a special evening. I left just before midnight, a new man, having just had my first three way.

Kevin called as usual the next morning to arrange for me to pick up my money, I wonder if he wanted to fuck me again? I needed a few days off after this, but the wonder of what my next assignment would be, kept me masturbating on a regular basis just thinking about it.

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This concludes Part 3. Please e-mail me with your thoughts. Any e-mails from a MM Couple would be highly appreciated.