Putting Myself Through College Ch. 09byRobXXX©
My Spring Break assignments were not finished, just my time pretending to be someone I was not, well at least the sex I was not. I received a call from Kevin the day after the cross dressing assignment, he apologized a little bit for the previous day, then jumped right back into work. That night he had another client for me, this one he said was a known client, who always liked a new model. The man went by the name detective, he was an actual retired police officer. I was told that he loved to handcuff and interrogate his models, and that the more I played along, the happier he would be. I could tell by Kevin's voice that this was a client that Kevin wanted me to impress.
I arrived at the client's home that evening at 7:30 as instructed. When I arrived, there was a note at the front door, with directions that I was to follow. Kevin had told me about this earlier, so I was not worried about the instructions. I was wearing jeans and a dark t-shirt, another request. The note said that I was to try and break into the house, that I was supposed to break in through a window around the back of the house. There was a fence around the backyard, so none of the client's neighbors would mistake my actions for the real thing.
I went around to the back of the house and found the window that was mentioned in the note. It was slightly ajar, so I started to push it open, half suspecting his face pop up at any minute. Instead this large man came at me from behind, and before I knew it I was on the ground being handcuffed and read my rights. He drug me into his house and into a room with only a small table and two chairs, I took it this was his interrogation room.
He yelled at me for a while and then recapped my crimes, the whole time I sat there with my mouth shut, letting him finish his diatribe. He then picked me up and pushed me back against the wall where he took a considerable amount of time frisking me, he must have checked my groin area five times. I was then offered a deal if I would confess, but before I could even speak, he screamed at me that I would be sorry for not taking his deal and admitting my guilt.
The "detective" told me that since I would not cooporate he would now have to strip search me. I was then picked up by the back of my pants and shoved across the room to the wall opposite from where I was frisked. I had not seen it earlier, but there was medal hook in the wall that had been driven in on both sides. One hand was released very briefly from the cuffs, only to be secured once again, as arms were suspended above my head with the cuffs secured to the hook.
The strip search began with the detective slowly untying my shoes, tossing both to the other side of the room. He then undid my pants, again slowly taking them off of my body. My shirt was then ripped off of my body, as it could not be lifted over me head due to the handcuffs. The detective took a step back and let his eyes roam my body, he then started to feel me all over, eventually working his way down to my feet. It was at this point that he removed my socks, taking each foot one by one into his hands, then he sucked on my toes.
The only thing left to do was to remove my underwear, but he did not. Instead he stuck his hand inside of them and felt around until I was erect. The detective then started to stroke my cock, but suddenly stopped and said that bad boys like I did not deserve any relief. He moved in very close to me, so that his body was pressing into mine, his hands grabbed a hold of my underwear, and then he ripped them off showing me his strength. At this point I was completely at his mercy, totally vulnerable, with no way to defend myself.
The detective then announced to me that he felt I was still hiding something, and thus he must given me a full body search. I hands were unsecured, as he led me over to the table in the middle of the room. I was thrown across the table as he pushed my face down, and yelled some more, he was determined to get a confession out of me. He released his hold on me for a moment while he retrieved some rope, I was then bound to the table. The detective left the room and returned with a bag. He held it up in front of me and asked me if I knew what it was. Once I said no, I was told this bag was a special bag, inside of it was his special tools for giving bad boy a full body cavity search.
Latex gloves were the first things that I saw retrieved from the bag, he put them on, and then stuck a finger into my mouth to probe all around. After he was satisfied that there was nothing in my mouth, he pulled out a ball gag, and secured it in and around my mouth. He next pulled out what looked like a leather bracelet. My groin was the next place of interest, as he poked and pulled it out from underneath my body. He then secured the bracelet thing around my cock and adjusted it so that it was too tight, causing me discomfort, I could tell that was his plan.
More yelling and some slaps to the back of my head were followed up by the client pulling a paddle out of his bag. He immediately moved around behind me and proceeded to paddle me for several minutes. I could not scream, but tears were running down my face from the pain, as he made sure that it was a spanking that I would never forget. The paddle was put down as he next pulled out a plastic bottle of petroleum jelly. He scoped globs of it onto his latex covered hands.
My very red and sore ass was now about to be searched, how at that moment I wished I had been a good boy and not tried to break into his detective's house. First one large finger, then a second, I was trying to scream no more when a third was worked in. This man was ripping me apart, and I could not stop it, I was totally at his mercy. I could feel that he was trying for a fourth finger, he most likely wanted to fist me, but thankfully he realized I was just not big enough to accommodate him.
The fingers were thankfully removed, but then I saw him go into his bag once more. He pulled out a very large butt plug, and then inserted it into me. I tried to move away, but the restraining rope held me in place. The plug was inserted into me, and then I was left there for a while to think about it. The detective then took a break and smoked a cigarette. He would blow the smoke into my face after each puff and once again offered me the chance to confess. When the ball gag was finally removed, I immediately admitted my guilt before he had a chance to do anything else to me.
The detective accepted my plea and judged me guilty as charged. He took his time removing the butt plug, and then the ropes. I was then given me sentence. I was thrown to the floor as the detective took out his cock and something that he had hidden behind him the entire time. He told me to suck his cock as he shoved it into my mouth, as I started to suck, he showed me his gun. Like a bad movie scene, he held the gun up to my head as I sucked his cock. I did the best job that I could, but I was not in the best shape after his interrogation. I worked his cock in and out of my mouth, making sure to use my tongue to work all around his tip and shaft. I worked me way down to his balls, and even moved my tongue further down, as my head was completely underneath him, I licked his ass. Was I scared, yes a little, but somehow I knew the gun was just a prop.
He ripped my head up, and then slapped me in the face knocking me back to the ground. I was pulled up by my head as he inserted his cock back into my mouth and with a firm grasp of my head, he fucked my face with as much force as he could muster. He shoved it in so hard that it was forced into my throat. He must have liked the feeling of being deep throated as he held it there, as a result I vomited. He released me only long enough for me to finish, then he shoved it back in until he finished, shooting his cum down my throat.
I was then told my sentence and taken from the room to his bedroom. He told me to lie down on the bed as he took his clothes off. The detective then put his cock at the entrance to my ass, and held it there for a while. He looked me dead in the eye and told me that he was going to fuck my ass, but if he ever caught me doing anything "bad" again, that he would kill my ass. As soon as his line was finished he pushed in.
Having just cum a few minutes early, the detective was able to hold out a long time, he gave me the fucking that I deserved. He looked me straight in the eye the entire time he was fucking me, drawing it out slowly then slamming it back in hard. Finally with one brutal thrust it was over, I could feel his ending shooting into my ass.
The client immediately turned into a different person at this point, he smiled for the first time and led me to his bathroom to clean up. While I was pulling myself back together, he had gathered up my clothes, sans my underwear and t-shirt. He watched me dress then, walked towards me and felt up my chest one last time, while never breaking eye contact. To my surprise he moved his face in suddenly and kissed me right on the lips, just a quick kiss, very gentle.
I was led to the door, shirtless, and told to leave. I did as told, but was completely uncomfortable leaving shirtless. It was still a little too cold, especially during the evening, but I had no choice. I had walked only about two blocks back towards where I could catch a bus back to my train, when a car pulled up along side of me, it was Kevin. He rolled down his window and handed me a shirt, he must have known this client very well. He made a comment about the way I was walking, but I was very sore. Thankfully though he did have my money, and I was paid right then and there. Kevin told me that he would call me the next day to discuss my next assignment, lucky me, after this one I needed a rest.
True to his word, Kevin was on the phone with me early the next day. He had two one hour assignments for me for that day. The first client a Mr. Beebe was an older man who I was told had an oral fixation. The second client was a businessman just in town that night, who went by the name of John. I took the assignments despite the way by body still felt from the night before, Kevin had a way of talking to people which could get them to do anything he wanted.
I meant the first client Mr. Beebe that afternoon, he meant me at his hotel door wearing only a robe. I had no more walked in the door when he let it fall open, exposing a very small erect penis. My god I thought to myself, this man makes me look like John Holmes. I was immediately ordered to start sucking, so I dropped to my knees barely three feet in the door and took his little cock, not even 5 inches into my mouth. I worked it for a while, I could do lot more with it than any other I had in my mouth before. I sucked it all the way in, and then licked his balls while his cock was still in my mouth.
Mr. Beebe was very nice at this point, complimenting me, which only encouraged me to do a better job. For the first time in my life, I was comfortable enough that I was able to relax and deep throat someone. I had the tip of his cock down my throat with the rest in my mouth. I could feel the base of his cock with the middle of my tongue each time I moved my face forward. This had quite the effect, as he exploded down my throat, but this was like no other, I had his cock in my throat so that blasts were half way down into my stomach before I felt them. This was a new sensation, Mr. Beebe did not know that I was enjoying this experience, probably more than he was.
Next thing Mr. Beebe led my over to a chair and just before I sat down, he lowered my pants to my ankles. Mr. Beebe then engulfed my cock and tried to out do my performance. I could tell that this man was an expert cocksucker, as he did things with my penis that I had never end thought to do in the past. Not only was this very pleasurable, but a learning experience as well. Mr. Beebe waited until I was almost there and then withheld my pleasure, he did this several times, bringing me almost to the edge then drawing back. He worked my cock for about 10 minutes before letting me cum. He did not swallow, only took it into his mouth, and then spit it out.
By this time Mr. Beebe was ready for another one, and I complied. I really tried to do my best, even incorporating a few things that he had just taught me. I only brought him to the edge and back twice, before he came. This time I spit it out, I was not sure why, but again I was just repeating his actions. Mr. Beebe thanked me for my time and sent me on my way, this assignment had lasted less than 45 minutes, a major bonus in my field.
John the second client of the day was a businessman from the Midwest, your typical closeted conservative from the central part of the country. I could tell that he was nervous, not only upon my arrival, but through out the entire session. There had been a few recent high profile busts in which several married businessman and other important figures had been arrested for trying to have sex with other men in public places, I guess this is what had driven John to me. Another clue was the fact that he mentioned how expensive my services were, money was something that no client, except for my bragging first had ever brought up.
John asked me to undress him, and then he returned the favor. He kissed me hesitantly for a while, before suggesting a 69, as if he needed my permission. We performed this act together on his bed, but neither of us finished one another. He next had me turn around and he kissed the back of my neck while masturbating my cock from behind. He did this until I had cum, and then pushed me forward, so that he could take me from behind. John pushed into my ass quickly, and thankfully his cock was still coated slightly with my saliva. He pounded my ass as quickly as he could, until he had cum, not two minutes into the act.
At this point John withdrew and did not say to much to me for a while, he cleaned off his cock, then walked around in front of me, and bent down to lick my cum up off the bed where it had landed earlier. John then turned his attention to the television and after five minutes or so I was left to wonder if I was just going to sit there naked until his hour was up. Sometime during this period though, John must have been getting up the encouragement to ask me the question. John finally looked at me and asked if I would fuck him, but that I had to be careful and take it slow.
John did not come back to the bed, instead he handed me a bottle of lube, then bent over the hotel dresser. I coated my cock with the lube, I had a feeling that this was not something that John had the pleasure of doing everyday. I rubbed some lube at his opening, and then inserted a finger to apply so more just inside his opening. I placed my cock at his opening and waited for a second, once I was sure that he would not change his mind, I pushed forward.
This man was tight, he was no virgin, but his ass immediately gripped my cock like it had never been gripped before. It was a memorable experience, I could feel ever movement around my entire cock. I fucked him slowly for a few moments, and then I too found myself climaxing very quickly. John though had enjoyed this very much, I could tell by his reaction and the words that he was saying to himself in a very low voice.
I pulled my cock from his ass, and as soon as it was out, our session ended. John asked me to quickly leave, so I put my clothes back on and walked out of there with a messy feeling inside my underwear. My train was delayed that evening, so it took me over two hours to get home. Kevin called me during this time to inquire about my availability for the next day.
During the rest of the long ride home I started to really think about Kevin, it dawned on me that he was nothing more than a pimp, he was not my friend. Kevin had been nice in the beginning, and while he has never turned on me, he has never shown any concern for my feelings after a few strange assignments. My eyes were finally opened, Kevin was in this for the money, and to tell you the truth, so was I to a point. Kevin had used me sexually a few times, and I had willingly let him. I guess at that moment I had an epiphany about what I had become, who Kevin was, and that I had come to terms with everything in my head.
This is the end of Part 9, please e-mail me with your thoughts, and if you want to see more. Thanks RobXXX