Professor Herbert's Assignment

My dad used to warn me: “you win some, you lose some”. He was a man of few words and it had made me and my brothers and sisters believe there was a pearl of ancient, simple wisdom in all he chose to say. Yet, even after all these years in college, I started to admit there was wisdom in this common sense.

Take me, for example. Since day one in San Francisco, I did all I could to make myself the best. The best student, writer, all of it. I was in all of it, working my ass off to get the best of me. That landed me an early opportunity. An internship all of my colleagues wanted and fought hard for. And they had chosen me.

It was the beginning of the end of my school greatness though. Even as an intern, the workload was enormous. Add that to the fact some of the other journalists always assumed that I was there to buy them their coffee and keep their desks clean. As humble as my old man had taught me to be, I, of course, submitted to those older men's commands, knowing one day I would be amongst them. That was the goal.

But for that to happen, I still needed to graduate. For that reason, with the paper in my hands, I ran down the halls, carefully passing through groups of students leaving their classes. I bumped into them and shouted apologies. I turned left and right and finally I found the class I was supposed to be in. The door was open. There was still a chance. I entered the enormous room and descended down the stairs jumping two at each time. By the main desk at the center of it all, an old colleague of mine was gathering some paper.

“Is this from Professor Herbert's assignment?” I asked, out of breath, as I reached him.

“Hello, Donnie. You are late.” It was his reply. Jack was a strong contender for the job I got. We used to be better friends. And that was saying much since I was never good at having friends. “Here.” He pulled a sheet of paper from between the others.

I took it in and looked at the grade in red. It was good but not as good as I once had been.

“Can I leave this one with you?”

“No, sorry. Professor Herbert took them all with him. He left two minutes ago.”

“Ah, for fuck sake.” This was the third time it happened. The third assignment that I was too late to deliver.

“Where were you?” Jack asked as he took his own bag and started up the stairs. “Come on, don't stand there, I have to lock this room and give the key back.”

“Right.” I started climbing after him. “There was something to work on. I stayed up all night long. They had me on call.”

“Uh-hum.” Jack's reply was still bitter whenever I mentioned the job. “Why don't you try to reach him at the parking lot. He might get it from you.”

We had reached the door and I nodded to Jack, patting him on the shoulders before starting down the halls again. This time, I rushed even harder. The last time I was late, Professor Herbert did accept my homework. He told me I had to participate in his class and he wasn't happy with my absence. But he did me the favor. And he said it wouldn't happen again. I did hope I could change his mind as I went out of the building and into the parking lot, stopping quickly by the entrance to look out for him.

A few meters from where I stood, he talked to another student. The girl seemed about to burst into tears in front of him. I knew I should have kept my distance, but maybe it was the rush of running around. Or the fear of constantly being late. The thing was... I ran to them and I reached them as he touched her shoulder. I heard his words, a rough whisper that left his lips as if he didn't want to be heard.

“You are a beautiful girl, Sally. The most beautiful I've been with in a long time. But I can't be the man for you. I just can't.”

Her red and wet eyes turned to me. And Professor Herbert's attention too. I stopped by them, breathing hard and I suddenly understood what I had done. Under their watch, I felt I could bury my head on the ground like one of those enormous birds at the zoo. I opened my mouth to say something, but all I managed to do was breathe in harder.

The girl shrugged the touch away from Herbert and nodded to the man.

“You can go to hell, professor.” She grunted before turning away and leaving in a rush, not looking over at where we were anymore.

And I stood there, next to my old Professor Herbert, who was probably as old as Sally's father. I watched her go and with the corner of my eyes, I looked at the old man. He wore a brown suit, which was somehow fashioned back at the time. His white shirt was buttoned up to his neck and his tie was perfectly tied. He was tall. As tall as I was, reaching almost 1,85m. He had large shoulders that filled up his coat quite nicely. Adding that to his voice, Paul S. Herbert was quite an imposing figure.

He turned to me and I saw blood on his eyes. He had black eyes and over his lips, a black mustache gave a bigger feel of masculinity to him. Now, back then I had never been with any man. Ever. I had had two girlfriends. One in high school and another in college, with whom I had lost my virginity in a weird and not sexy way. She dumped me a couple of weeks after.

I struggled because under those angry eyes, I felt myself get hard. I shook the feeling away and tried to smile at him. My best smile. People had always told me I had a nice smile. I tried that with him.

“Sorry to interrupt, Professor. I met Jack in class and he told me I could find you here. I have brought you my paper.”

He looked at me for a few seconds of complete silence. I almost held my breath. He was not saying anything but I could feel his eyes analyzing me. Under that sight, the volume of my bulge grew. I wanted to put my hands on my pockets to hide it. But honestly, I didn't know if that would be a wise choice. Even if I could do it. Because under his eyes, I felt paralyzed. For a brief moment, I thought his eyes had turned down. My heart skipped a beat at that. Had he seen me hard? I raised the papers as if the enchantment was broken and I was free. It was a desperate move to try and hide my growing volume.

“No.” He grunted and started walking away.

I stood there, holding the paper to an invisible companion, as it hit me. An old me would have given up. I was always terribly afraid of authority. People in a position above mine always made me feel as if I was not worth their time. And yet, I moved towards him.

“Professor, I am sorry. They kept me all night at the Chronicle. I came home around seven and yet I did the assignment, Sir. I really, really think you should take it.”

He stopped and turned to me.

“I should?”

For a journalist, I apparently had a terrible way of choosing my words.

“I mean...”

He crossed his arms, staring at me with pure content.

“I am a good student, Sir. I promise you that. And I have worked my ass off. I... please. I can't have a bad grade. It's my future at stake.”

I lowered my eyes, ready to accept defeat. He stared at me and I could feel his eyes on me. And I could feel the hatred there. Or something close. When I raised my eyes again, he had a grin on his face.

“Fine. If you want me to take it, I will.”

I couldn't control it. I opened a big smile to him, lifting the paper as if ready to handle it to him. But he shook his head at that, scoffing.

“Enter the car, Mr. Graysmith.” His voice was hoarse and commanding.

"I beg your pardon.”

"I said enter the car.” He motioned to an old BMW on the side. “Or else you can take your papers home.”

I didn't dare to move as my brain tried to work through that situation. What was really expected of me at that point? I hesitated and watched him opening the driver's door. I looked over my shoulders, to the imposing buildings of my college. They were a safe place, my island. Somehow I knew that if I entered that car, I would be going on an adventure. And I was never an adventurous person. I thought about Sally, how she shrugged under his touch. How she walked away never looking back. I wondered if she had entered that car as well.

"Mr. Graysmith?”

I looked at him and I felt my cock throb as I imagine Sally sitting there, where I would sit. I walked to the car and entered through the passenger side. I sat down and put on my seat belt as he was doing the same. He touched my knee and squeezed it and my cock reacted immediately. He started the car and through the side window, I watched the buildings being left behind, turning smaller and smaller as the car started faster. And soon we were passing through the University's gates, going down the road and leaving all I knew behind.

After my ex, Tina, broke up with me, I went downtown to Castro. I would not have admitted it aloud, but inside I knew what I needed to do. I spent a day walking around, looking at buildings I knew were for sexual encounters between gay men. I found myself by their door, asking myself if I would dare to come in. It was a struggle that day. It was painful and it hurt deep. All I did, in the end, was buy some magazines of naked men. I still had them somewhere under my mattress in the dorm.

We traveled in silence as we entered the city and went through the blocks of houses. We passed through neighborhoods and we climbed hills until he finally started slowing down. He hadn't said a word and I kept it to myself, thinking about that day in Castro. And thinking of Sally. I imagined Sally with that old man by my side and it was as if I was burning inside. Strangely, Sally was just a shadow in these thoughts. My brain was trying hard to figure out what hid under that suit and what had Sally felt when she touched it.

The car stopped by a two-floor house. It was an old-style building, typical of the city. I had never been inside of one, but I have already gone through the city to just take a look and take pictures. I didn't expect Professor Herbert to live in one but when the engines stopped working, he tapped my knee.

"Come.“

That was the only word he had said since we had left campus. I stepped out of the car and closed the door. The street was quite empty, even though it was still the middle of the day. One car went down the hill as I followed my professor through the entrance and stopped a couple of steps away as he unlocked the door and stood to the side. It was his invitation for me to come in, but the gesture seemed more like another silent command of his. I nodded, still holding to the papers with my left hand.

The hall of the house was barely illuminated. I noticed a place for the shoes so I quickly took mine off and let them on the side. I heard the door locking behind me as my eyes adjusted to the dim light. I could see coats by my right side and ahead, the stairs that would lead to the second floor. The hall ended in another room, which I figured was the kitchen. To my right side, there was a door to a room that seemed way more illuminated by the sunlight. I stepped to the side, my eyes wandering all over, taking all the details, when I felt a hand on my shoulder.

"Now, Mr. Graysmith, this is the third time something of the sorts happens between the two of us. I am a patient man, but even my patience has a limit. And yet, I am not unkind to my students, especially when they prove themselves to be better.“

His firm touch led us into the house. We turned to the right and entered a living room. To the street, an enormous window was in the corner. There were a few plants here and there among the old-style couches and a small table. One of the walls was covered with books and a small, box television was in a corner. The biggest chair was the one that looked most used. It faced the tv and had a small table at its side where an empty mug was left on top of some newspaper. I entered and my eyes caught all the details that it could as I felt his warm hand now on my neck. He pulled me into that room and made me sit on the bigger couch.

"But I must add, despite your brilliant works so far, you have been pushing my limits. And I don't like that. I don't like students who take advantage of my kindness.“

I nodded as he sat down on the chair and looked at me with his small black eyes. Again, I felt as if he was measuring me. And again, because of that, a feeling on my stomach went down like liquid gold, to my crotch. I felt myself hard under those measuring eyes. And I asked myself if Sally felt the same when she came to visit.

"I am so sorry, Professor. I really don't mean to do so.“

"That's why I brought you here, Mr. Graysmith.“ His voice came over mine so I stopped my excuses immediately. All I did was watch and listen. "I have good faith in you. But I must ask you if you are willing to put your money where your mouth is.“ He leaned over, his elbows resting on his knees as he held both hands in front of him, watching attentively. "Are you?“

I nodded, my breath stuck on my throat as the professor talked.

"Leave your paper there, over the table.“

I did as he told and when I looked over at him, he had a smile on his face. It was a dirty smile. One that I had always associated with my Uncle Mark, who had been a ladies man and trouble to all my family. Word in town was that he had more than one bastard running wild. And all his boys were, unfortunately, just like his dad. They were always ready to go for girls. And their dirty smile was the signature all old ladies warned their daughters about.

"Now, I will accept your paperwork, but first we need to come to an agreement. What you saw today in the parking lot...“

"I didn't, Sir, I was just-“

He raised a hand that made me shut up immediately.

"What you saw today at the parking lot is a rather private matter. But you are an intelligent boy, aren't you? You figured it out. Only one dumb kid would not. Sally had come with me to this house several times. I fucked her right there, where you are sitting. I did more." He admitted all of that without one trace of shame or demure. "She was a very obedient girl. She came from a very catholic family down from Texas. She was a smart girl too. And she had needs that I helped her take care of.“

He laid back on his chair.

"But she wasn't enough. I tried to push the buttons, but she didn't follow. So I called her yesterday and canceled our meeting. I told her we were done. Which led to us, today.“

I think my face was burning. I felt it burning. And I was always easily red. I didn't lower my eyes though. I drank every word of his little story and I felt my heart beating fast, my cock growing hard. Harder. I felt it wetting my underwear as he looked at me, the dirty smile still there.

"Are you interested to know what I did to her there, where you are sitting?“

I swallowed hard. I wanted to say no. That it was rude of him. He was being completely rude. I didn't know why he was telling me that, but I didn't want to know. I hesitated, my eyes staring at him in complete disbelief. He waited, patiently. And my hesitation just lasted more and more.

"Or do you prefer I show you?“

The words were like a slap to my face. I stared at him, opening my mouth again, ready to protest.

"Professor.“ I started, but he got up immediately, walking towards me and grabbing my hair with his fingers. 

"Think hard what you are going to say, boy.“

I looked up at him, scared of that new development of our relationship. I tried to think, but my brain was taken by a blinding lust. I remembered one of the magazines I had bought. In it, an older trucker fucked a younger man on a toilet. I had played with my dick staring at the pictures, reading the story that accompanied it. The trucker saw the boy staring at his cock and that was an insult to his own masculinity. So he punished the boy by fucking him hard. Even when other men came in, he didn't stop. He would tell the other men that the boy was looking for dick. And he would offer the boy too.

That was on my mind. That story only. And somehow Professor Herbert could read it too in my eyes.

"I know, boy. I know.“ He said as softly as his hoarse voice could be. He freed me from his grip on my hair and his hand was on my crotch before I could even do something. He grabbed it hard and I felt pain on my balls. I groaned, looking up at him. His eyes, his black dark eyes were filled with a savage lust. "I know you want to take Sally's place. Isn't it right?“

I nodded. I fucking nodded at that question. And I knew I was doomed for it.

He pulled his hand back and stood up, looking like the old Professor Herbert once more. "Take your clothes off. Not your underwear, but all the rest. I'll be in the kitchen preparing some coffee.“ He turned and left the room as if nothing more had happened. He left without another glance at me.

My first thought was the window. Someone could see. I stood up and walked towards it. There was a thin, almost transparent curtain. I pulled it over the windows and turned again. My head was throbbing and so was my cock. I looked at the paper over his small table. That was my mission and I had accomplished it. I walked immediately to the door but stopped before leaving. I could see the hall in front of me, nothing held me back. But I felt as if an invisible wall stood before me. As if air pushed me back into the living room. I bit my lower lip and turned, trying to figure out a way to escape. To run. I crossed the invisible wall with effort and I felt sweat over my back, wetting my white shirt. I found my shoes and put them on and I reached for the door. I stopped myself for a moment. One part of me wanted to stay. One part of me wanted desperately to know what Sally knew. I looked over my shoulders and I heard the hot water boiling in the kitchen. I shook my head, trying to shake off the feelings and thoughts. Those damned dirty thoughts. I imagined myself going home and burning all those damn magazines. I would even go to church on Sunday. I would, I promised myself.

I reached for the door and tried turning the doorknob. Nothing happened. I heard the click, but nothing happened. He had locked us inside. I stepped back, the realization falling over my shoulders. I tried to breathe and think. Professor Herbert would, of course, let me go. I turned, decided to go talk to him in the kitchen. But by the door frame, he stood with the keys on one hand.

"You are not naked.“

"No, Sir. I-“

"Do you really want to leave, Mr. Graysmith?“

I lowered my eyes once more. My heart was beating so fast. How would I tell that man that I didn't know? I heard his feet coming closer. I felt his hand on my shoulder. "Come.“ He whispered.

And I followed. We were back in the living room. "Sit.“ He ordered and left me there once more. I had not dared to look at him. I still looked at my own shoes, at my own hands. Thoughts clashed over my head, so hard that they hurt.

I heard him coming in and he put a mug over my homework. He sat next to me. I still didn't dare to look. He took my hand and led it to his crotch. I let him. I offered no resistance. That was the first time I felt a cock under my hand. It was still inside his trousers. But I felt it. Big. Hard. Pulsating. I finally dared to look up. He stared down at me.

"I give you another chance, Mr. Graysmith. And this is the last one.“ He paused, letting go of my hand. I continued to work my fingers on his crotch, massaging whatever was down there, waiting for me. "Will you take it? Or will you leave it?“

Next to the mug, he left the keys to his house. I stared at them for a brief moment and then returned my eyes to his face. He smiled and I felt his cock moving under my fingers, like a living being trapped in a cage.

"Good. You made the right choice. But you did disobey me and unfortunately, I cannot accept such terrible behavior. You are going to lay on my lap so I can give you a good spank. You are going to count to ten. I think ten is a good start.“

I looked at him, not believing his words. But I didn't need to. He held me by my neck and pulled me down so I had nothing else to do but obey. My stomach was against one of his knees as I looked at one of the pillows of his couch. He caressed my ass and my cock throbbed hard in my pants.

"Count.“

His hand hit me so hard that I let out a whimper. The sound of it was muffled thanks to my trousers. But I damn well felt it. I remembered when I was a kid and my dad used to put me over his knees and spank me. He stopped once when, after he was done, I was crying loud and my dick was hard as a rock. It was the last time he ever spanked me. Ever.

"Four. Five.“ Each number was followed by the next slap. Hard and uncaring. Far from gentle. He slapped so hard that despite all I wore, I felt the skin of my ass begin to burn. When I reached ten, I felt tears on my eyes.

Professor Hebert helped me up. I sat down and looked at him. He touched my face with his rough fingers. "Are you going to obey me now? Are you going to be my good boy, son?“

I nodded at the question.

"Take your pants off.“

I stood up, looking down as I took my shoes off and unzipped my jeans, pulling them down and standing up with them around my ankles. I wore old white briefs. A dark wet stain was on it as my cock pushed the tissue forward. It was a tight small underwear and because of my hard-on, my black wild pubes were out, the cloth pulling between my round cheeks, entering my crack. I had a good size of cock. It was uncut but very hairy. Professor Herbert looked at it and laughed.

He put his fingers over the wet spot.

"Not even Sally was this horny on her first night.“ He looked over at me. "Take your shirts off too, boy. And why the hell are my windows closed.“ He stood up and walked past me, pulling the curtains away from the big windows before opening them up and letting the fresh air blow in.

When he turned, I had only my briefs on with my cock pushing it forward. I had just completed 25 one month before. I had black hair all over my chest and abs. I had developed well because I used to play football in school. I stopped in college so I had gained some weight, but the muscles were still there from occasional training and the new weight seemed to fit with the rest. I had hairy armpits and a hairy ass. I tried to cover my cock but I saw Professor Herbert shaking his head and my hands stopped in the middle of the way.

He came to me and his hands were guiding me. He pushed me over the couch and I knelt on it. He made me bent over, my chest against the back, my face almost touching the wall behind. "Take your panties off.“

Without looking back, I did. I pulled my briefs off, revealing my hairy ass to my old professor. He was watching up close, I could feel his eyes on me. To my own shame, I was loving it. My panties, as he called them, were gone too. He helped me out of them. He took them and pulled them off of me. When I turned to look, he had them over his face, sniffing them. He threw them over at me when he caught me looking.

"You smell like a bitch. Put it in your mouth.“

I obeyed. He approached me and put his fingers over my ass. He opened my cheeks and looked at my tight, virgin hole. He spat over it and used his thumb to spread his saliva. I moaned but it was a muffled sound against my own underwear that I was biting and tasting.

"You are tight. Are you a virgin here?“ He asked, pressing his thumb hard. Hard enough that my pucker started to give in, allowing his digit just a bit. It was a lot of pressure, or so it felt. I groaned, closing my eyes at that new touch. He pulled back and I nodded at his question. "I will break you in.“

He walked to the wall where the books were. I looked over my shoulders, not daring to change position. I watched him take a black box from one corner and take from it something I could not see. When he walked back to me, he was holding a small pot of Vaseline.

He unzipped the brown trousers he wore and pulled off his cock. He didn't even give me the chance to take a look at his body. When he saw me looking, he raised one hand and slapped my ass really hard. Another muffled moan came in, but it was nothing to him.

"Look over at the wall.“

I nodded and did as he said. The white wall had no noticeable details. And besides, it did not matter. I was about to lose my virginity to my old professor. My old professor who I was sure was at least double my age. I felt his thick fingers on my crack, spreading vaseline all over my cheeks, my ass, and especially over my pucker. He pressed his finger in and it slid so easily that startled me. I clenched my hole hard and groaned over at my underwear. He laughed.

"Calm down, son. Easy now.“

He pulled his finger out and pressed two digits. They also slid in easily with how much grease he had put over my ass. I cried into the underwear and another muffled sound was gone to waste. His fingers dug in deeper, spreading my hole, my pucker apart. I grunted and moaned and closed my eyes, trying to relax. My own cock was hard and aching. I reached one hand to it and I immediately felt a slap on my ear.

"Don't touch yourself. Do you hear me?“ My ears were ringing and I was slightly off-balanced. But I heard him. I put my hands down on the couch and waited.

His two digits pulled out and my ass was once again empty. But not for long. One of his hands held me down by my lower back. I raised my ass a bit because of that and I felt his cock pushing against my virgin pucker.

"I love tight virgins.“ It was all he said as his cock was being pushed in deep into me. I screamed against my underwear. I cried and I even tried to pull back, but he held me. It was a pain that went over to my guts, up to my spine. I felt like I was being broken in two. Whatever he was pushing inside of me, felt big, thick. "Shhh, Daddy's coming in.“

His voice hit me deep into all of that confusion. I breathed in.

"Are you a bitch or a man? Take it like a man, you dumb fuck.“ His words continued to slap me just like his hand did. I felt my cheeks burning red, I felt my ass being torn apart. But each new word made me toughen up. At least, that's how I felt.

He pushed himself all the way in and I felt my hole full of cock. For the first time. I never imagine it would hurt so damn much. In the magazines, the bottoms always seemed to love it. I imagine myself in their places, taking all of those handsome men with their big dicks. But now, I felt like I was going to cry.

"Please, Sir.“ My muffled cry came through the cloth.

"Shh, it hurts. I know it does.“ I felt his body over mine and he kissed my ear. Softly. "But I will train you to never feel this pain again. Never.“

The uncomfortable feeling remained but while he didn't move, I could feel the pain slowly receding. I thought I was ready so I moved just a bit. It made me clench my hole. I moaned. I didn't know if from pain or pleasure, but I moaned. And my Professor took it as the sign he needed. The hand on my lower back firmed me in position and he started banging me hard. His cock moved back and forth and each new thrust was a gain of rhythm, a gain of speed and force.

By the third or fourth, I was already a mess of mumbling, moaning, and grunting. I felt my insides being touched, I felt parts of me I never knew existed sending messages to my brain. I felt pain. But a sweet kind of pain. His cock was thick, I could tell it. I hadn't properly seen it, but I felt it in my guts. A well-deserved place to be.

Sometimes it felt like I was going to make a mess, make us dirty. I would open my ass and put a hand over his chest. Professor Herbert would tell me to not worry. He would slow down though, sometimes even stop. He would caress my back and pat my ass. "Enjoy your first cock, son.“

And I did. I eventually did. It was strange. A quick, brief moment of letting go. I breathed in deep. And I felt myself relaxing. Professor Herbert held me by both sides of my waist and he started pounding hard again. Harder than ever. I was screaming at this point, completely pounded into the oblivion. No shame, no fear, just cock. Cock up my hole, breaking me to serve his pleasure, a Man's own pleasure. My Professor. My Man.

I didn't even try to stop my orgasm. It filled me from head to toes and I shot over his couch. It was so intense that I felt I could pass out. I shot a thick load. A big load. I was sweating from head to toes and my hole was clenching hard on Professor Herbert's dick. I felt myself involuntarily milking his dick and soon he was flooding me with his own seed. Deep into me.

He let himself fall over my back when we were both done. He kissed my shoulder and stood up a moment later, pulling his cock out. I felt it sloppy. And I felt cum dripping from it. I immediately rose and put a hand on my ass, holding whatever was coming out. Professor Herbert seemed to notice it. He patted my shoulder, taking a small handkerchief from the black box to clean himself.

"Follow me. Let us clean ourselves now, son.“

I did. My legs seemed weak, shaky, open. I felt open. I felt as if I walked like a cowboy. He was waiting for me by the stairs. "In this house, you will always be naked. Are we clear?“

I nodded.

"Come on. Follow me.“

Up the stairs, we went, and I felt cum dripping out of my used hole, right into my fingers. I had been fucked by a real Man. Everything was different now.