So one day I’m just sitting in my apartment, bored and horny, reading some online personals. Most of them are totally pathetic and I’m having a hard time even maintaining an erection. I never really answer personals but sometimes they get me pretty excited and I end up with a damn good orgasm. On this particular day, however, they weren’t even getting me hard. I was just about to give up when one definitely got my attention.
56 y/o WM professor ISO failing student in need of extra credit assignment. You can’t afford to fail my class. What will you do raise your grade?
This turned me on. I e-mailed him right then and begged for an extra credit assignment. I told him I need to pass his class to graduate and that my parents would kill me if I didn’t graduate on time. I stressed that I’d do ANYTHING for a passing grade. Two days later he replied. He gave me the address of his office (at a university downtown) and told me to be there Tuesday at 5:30. This had potential.
I went to work that Tuesday with a backpack and a change of clothes. I had a lot of trouble concentrating all day. Mostly I just sat staring at the clock waiting for 5 o’clock. When quitting time finally arrived, I grabbed my backpack and ran down the stairs and out to the subway. The anticipation was killing me. When I finally got to the building his office was in, I ducked into a bathroom on the first floor and changed into the extra clothes I brought. I wanted to look the part, so my suit came off and jeans and a t-shirt, sneakers, and a baseball cap went on. I put my suit in the bag and went looking for the elevator.
I knocked on his office door and he told me to enter. “Hi Professor,” I said. “I’m Joe. You told me to come to talk about extra credit because I’m not doing to well in your class.” “Yes,” he answered. “You’re not doing well at all.”
The Professor was a grey haired man who looked his age (56) and although he was sitting at his desk, I could tell he was a bit overweight. Not especially attractive, though he wasn’t terrible looking either. It was actually perfect for the role I was all too eager to play. “Shut the door,” he commanded.
I shut the door and walked to the side of his desk. He mentioned something about how I’m a fine looking boy and he’s surprised he doesn’t really remember me from class. I told him it might be because I don’t go too often. He asked me if I work out and mentioned how he’d gained a lot of weight since he stopped running a few years ago. He suggested that maybe for extra credit I could be his sort of personal trainer to help get him back in shape. At this point I got a little confused. Had I totally misread this guy? Is this not going to be what I had expected?
“Well, I don’t really know how qualified you are to be a personal trainer, ” he said. “You look pretty fit now, but much of your body’s hidden under all those clothes. Take them off.”
“Now? Here?” I asked, pretending to be surprised and embarrassed. “Yes,” he answered. “Here and now.”
I pulled off my shirt and bent over to untie my sneakers. I un-zipped my pants and pushed them to my feet. Then I stepped out of my pants and stood there in my boxers and socks. “That’s very nice, but you still have some clothes on, don’t you?”
“Sorry,” I said and I bent over to pull off my socks. Slowly then, savoring my role as a stripper, I slowly wiggled out of my underware. My dick was hard enough to look impressive, but not so hard that it stood out straight. The Professor liked what he saw.
“Very nice,” he said. “Now come over here.” I walked over next to his desk and noticed that he had un-zipped his pants and pulled out his cock. It was not so impressive. He was about 5 or 6 inches, circumcised, and not very thick. He was semi hard and it was not sticking out very far past the edge of his pants. “I haven’t had a good blow job for quite some time,” he announced. “If you’d like to pass my class, perhaps you can do something about that.”
I knelt on the cold tile floor between his legs. I grabbed his prick and leaned in to engulf it in my mouth. He tasted like sweat and his overgrown pubic hairs were everywhere. I bobbed up and down on his penis sucking away, hoping if I sucked hard enough it would grow a bit. He decided he wasn’t comfortable enough and stopped me so that he could pull his pants down to his ankles and unbutton his shirt. I went back in feeling more like a whore than ever. The guys legs were fat and hairy, his nutsack was sweaty and smelly, and his gut hung over his waist like a giant glacier ready to unleash a deadly avalanche of fat. I hesitated for a minute.
“May I remind you that you’re failing my class?” he asked. “You need to suck my dick and swallow every last drop of cum I feed you, young man, or you won’t graduate.” My own cock started stirring and I started sucking for all I was worth. He grabbed my head and held it still while he started fucking my mouth. His spare tire gut was hitting my forehead with each thrust and his nuts were hitting my chin. I felt so dirty. I was loving it.
Finally he started cumming in my mouth. Even his cum tasted bad. I was far more bitter than any I’d had before. He told me not to swallow because he wanted to see it on my tongue. I obeyed and opened my mouth to show him what I’d collected. “Okay,” he said, “you can swallow now.” I swallowed and almost gagged. It really tasted bad. “Well then, ” he said. “That wasn’t bad. I’m willing to consider giving you an extra credit project. Come back Thursday, same time, to discuss the details.”
I got dressed and left. The terrible taste of his cum mixed with his sweaty balls was in my mouth the whole way home. When I got back to my apartment. I stripped naked and jerked myself off to an amazing orgasm. Then I brushed my teeth.
Thursday, I followed the same routine of leaving work and changing my clothes in the first floor bathroom of his office building. Again he had me lock the door and strip naked. He stayed at his desk and pulled a dildo and some lube out of one of his drawers. He them to me and told me to fuck myself in the ass with the dildo while he finished grading some papers. I sat on the floor and began fingering my ass. The floor was cold and hard and I really started getting off on the idea of sitting there naked, next to this fully clothed man. It was so degrading.
I played with the dildo for a while, rubbing around my asshole. The skin right at the opening of my anus is so sensitive, I love the feeling of the lube on my ass-lips. I pressed the tip of the dildo against the opening very gently and savored all the feeling of my asshole loosening up and spreading open to allow entrance into my rectum. I pushed a bit harder and the dildo slid up inside me. My cock immediately sprang to full attention and I pushed even harder, feeling the plastic cock slide up past my prostate milking a few drops of precum out of me. I was just starting to really get into it when the Professor stood up.
“Okay boy, “he said. “Get that thing outta your ass and bend over this desk. You’re about to get fucked for real.” I stood up and bent over the desk. Apparently he had gotten pretty hard watching me and didn’t need any fluffing. He stood behind me, pants around his ankles and pushed the head of his cock against my puckered anus. I loosened up as best I could and in he popped, right down to the base of his shaft. His dick was actually a bit smaller than the dildo and slid in without hesitation. He didn’t waste any time. He started thrusting his prick into me as deep as he could, then pulling all the way back out and then plunging it all the way back in. I stood there, bent over his desk focusing not only on the feeling of his cock up my ass, but also of his big, fat belly smacking against my ass and back. I was getting fucked by a big fat pig and I loved it. I was hard as a rock.
Eventually he started grunting and with one last push, he buried his prick as far inside me as he could get it and I felt streams of cum shooting out into my colon. He pulled out quickly and warned me not to let any cum drip out onto his office floor. “Tuesday five thirty,” he said, “now get outta here.” I asked if I my performance was helping my grade. I was standing next to his desk, butt naked, clenching my ass cheeks together to keep all the cum inside. He looked at me and stroked my hard penis for a second. Then he said, “Tuesday at five thirty. You’re on your way.”
So the following Tuesday I showed up at his office and started to get undressed, but he stopped me. “Keep your clothes on,” he said, “we’re leaving.” He stood up, put on his hat and coat and held open the door. We went outside into the street and walked a few blocks to a small residential building. We went up into his apartment and he told me to go into the bedroom and get undressed. The apartment had a decent sized living room with a couch, two easy chairs, a table, and a TV. There was also a kitchen, a bathroom, and two bedrooms (one of which he turned into a study). I went into the bedroom and got undressed. He gave me a dildo and some lube and told me to “get myself ready.”
I sat in his room for at least a half hour, playing with the dildo in my ass, wondering what was taking so long. Finally he came in and told me to leave the dildo and follow him out. As I walked out into the living room and saw what he had arranged, my stomach dropped and my heart was racing. Seated in the couch and chairs were four other men, looking me up and down and saying things like, “well done, Peter. A fine specimen.”
I stood there, completely naked, being ogled by these men, and I was so turned on that my dick felt like it might explode. The four men must have all been professors, too. One was younger and good looking, about 35 years old and in good shape. Another was much like my Professor, mid-fifties and overweight. The last two were both even older, I’d guess late sixties or early seventies. One of them was a bit heavy, but the other was stick thin. The Professor took the remaining seat and told me to stand in the center of the room (he had moved the table aside).
“Gentlemen,” he began, “this young pupil of mine has found himself in quite a predicament. He’s needs an ‘A’ in my class to graduate on time, and currently, he’s failing. He’s volunteered for an extra credit assignment. This is his assignment. He’s ours to do with as we please.”
“Son,” he said to me, “you can begin by sucking our cocks.”
With that, all the men opened their pants and started pulling out their penises. Some just pulled it through the zipper opening, while others pushed their pants down to their ankles and spread their legs. I went to the younger one first. He had a beautiful penis – long, thin, circumcised, and slightly curved upward. I sucked him for a few minutes and then moved on to the next. This was the heavy older man. He wasn’t even hard. I was thinking ‘I hope he took his Viagra,’ as I went down on his limp little dick. With a little licking and sucking I managed to get him up, but even at full attention his little soldier was not scaring anyone. I moved on to the next guy who was built like my Professor. He was just as sweaty as, too and I got just a bit nauseous as I licked up and down his shaft and around his balls. Fat and sweaty as he was, though, his cock was huge – about twice the thickness of the next biggest.
By the time I got to the second older guy, the youngest one was up from his seat and started fingering my ass. I tried to concentrate on the wrinkled old dick in my mouth, but the guy behind me kept talking dirty while he attempted to stuff more and more fingers up my ass. “Yeah bitch, you like that old man’s dick,” he said. “How did a little whore like you get such a tight asshole? I should be able to drive truck up the ass of a little hooker like you.” I moved on to the next cock, which was my Professor’s and sucked on it like a starving man. The guy in my ass was getting me so hot, I was losing control of myself. Finally he pulled out his fingers and replaced them with his dick. Precum was dripping out of me so fast it felt like I was peeing.
For the next hour I was passed back and forth between these men, sometimes on all fours, sometimes on my back, sometimes bent over the side of the couch. As they fucked my ass and mouth, I concentrated on how unattractive they were. I was really getting off on the idea that they were all (or almost all) dirty, fat, disgusting, old men and I was their whore. Eventually each of them came in me and when they were done I had about three loads of cum up my ass and two in my stomach.
When the last one came, I thought that would be it, but boy was I wrong. The Professor went into his kitchen and came out with a humongous cucumber. “Let’s see you get this up your ass,” he said, handing it to me. I started to work it around my well-used anus and the tip slid in pretty easily. The rest of it was another story. This thing was huge. I tried everything I could think of to get it in without tearing myself apart, but there was just too much pain when I pushed. I reached a few fingers into my ass (and it was a bit disturbing how easily they slid right in) and scooped out some cum to lube the cucumber with. I tried clenching my ass muscles as hard as I could for as long as I could to try to loosen them up. But mostly, I just pushed and pushed and pushed. All of a sudden, like a dam had burst, my ass hole open just a bit more and the widest part of the cucumber flew up inside. My penis shot up like a rocket. This was the most intense feeling I’d ever had. The fullness in my rectum was overwhelming. My prostate was being squished so hard that I think it emptied all the precum I had. I started to get dizzy and really felt like I was on drugs. I was in another world.
I played with the cucumber for a few more minutes taking the whole giant thing up into my ass. My audience was very impressed and the younger ones were starting to get hard again. Professor went into the study and came back with a new challenge – an aluminum baseball bat. “Here you go, slut. Try this.”
I pulled out the cucumber and scooped out some more cum to lube up the bat. I was insane with lust. The bat was actually not much thicker than the cucumber and it it slid in fairly easily. The problem was that it was so long I kept trying to get more and more of it in. Some of they guys came over to help and grabbed the end of the bat and started pushing it up my ass. It was incredibly painful, but all I thought about was how I was lying naked on the floor of an apartment with five older men who were shoving a baseball bat up my ass. I started cumming without even touching my dick. Gobs of cum were shooting out all over my stomach, my chest and the floor. At this they pulled the bat out and told me to clean up the mess I’d made.
I scooped the cum off myself and licked it off my fingers. I was still way over the edge and willing to do anything they wanted. I got on all fours and licked the cum off the floor like a dog. One of the guys then decided to fist me. I felt his five fingers pressing against my ass-lips and a burning pain shot through me. I cried out but soon had a penis shoved into my mouth. To take my mind off the pain in my asshole, I concentrated fully on the cock in my mouth. As I licked and sucked and slurped away, I felt a great relief as the man’s knuckles cleared the rim of my anus and his whole hand slipped in up to the wrist. The guy I was sucking got really turned on by that and soon started squirting into my mouth. While the guy fisting me attempted to get in up to elbow, I sucked off two of the other guys again. Finally the fister had enough and decided to fuck me.
When he pulled his arm out of my rectum, I felt a gust of wind shoot up inside me. I felt wide open. I knew my asshole had not closed back up. I was gaping wide open. The guy put his cock in me, but I was open so wide I could barely feel him in me. He must have been pretty turned on because he came after only a few thrusts. Everyone had come twice and seemed about ready to pass out and I started thinking that was the end. There was just one more thing to put the icing on the cake.
As I lay on my back with my asshole still open wide, the other middle aged guy stood up and came over to me. He told me to roll up onto my shoulders so that my legs went behind my head and my ass was straight up in the air. He then positioned himself directly over my gaping hole and with two fingers of each hand stretched it even wider. As I prepared myself to get fucked again, I felt a strange sensation. A warm fluid was splashing around my asshole and pouring inside me. He was pissing into my open anus. The feeling of the hot piss filling me up inside was unbelievable. I was instantly hard again. He pissed about a half a liter and then warned me not to let any drip on the floor.
I rolled down onto my back and started to get up when I felt a barely controllable urge to empty my bowels. The Professor handed me my clothes and told me I was finished, but that if I wanted to pass the class I’d have to see him again next Tuesday. I begged him to let me use the bathroom first, but he refused. He opened the door and threw my clothes out in the hall. I ran out after them and quickly got dressed in the hallway with tiny squirts of cum and piss leaking out of my ass. I ran down the stairs squeezing my ass as hard as I could to keep it all in, but as I ran out into the street, I lost control.
I gave up trying and slowly walked toward the subway with piss and cum gushing out of my ass and down my legs, soaking my jeans. I smelled like a urinal and felt like a crack whore. I couldn’t wait to get home and jerk off.