DISCLAIMER:
This story is a work of fiction and contains descriptions of explicit sexual acts of boys and men discovering their sexuality. It contains graphic scenes of sex between consenting underage boy and adult males... If this type of content offends you or you are under the age of 18 do not read it.
Author's Note:
This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission.
If it is illegal to read such material where you live or if you find the topic distasteful the please leave now. If you enjoy the story or if it evokes memories of your own, please let me know. I am happy to write stories from outlines.
Copyright 2016 Wolf, All rights reserved.
You may contact me at pomowolf74@yahoo.com if you like. All flames will be ignored.
Deflowering a Collage Boy
By
Wolf
My life changed the night after finishing taking my semester finals at the University of Berkeley. I felt like celebrating so took pains selecting my clothes. I selected my shined oxfords, Navy slacks, a royal blue gingham sports shirt, a gray cardigan sweater, and a water repellent wind backer with hood tucked into the collar. I walked to a bar about a mile from the campus called 'The White Horse Bar.'
When I reached the door of a bar with a diamond tucked vinyl covered door. The smell of cigarette smoke and booze seeped from the door. I entered on impulse. It was mixed bar during the day, but became a gay bar after dark. I was curious to see what a San Francisco area fay bar was like.
I thought I'd give myself a treat and go to one. Everybody knew about The Black Cat, which supposedly was "rough trade bar," down near the Embarcadero. But one contact at The White horse told me the names of three bars in San Francisco.
I decided the one where I'd feel safe was one on Taylor Street. It was just the street number, 487 Taylor Street or something like that, on a door otherwise blank. I had been told that it was a "coat and tie" bar, so I dressed appropriately. I'm sure I looked lost, but one man walked up to me, introduced himself as Harris, and led me to a table where he bought me drinks. I told him where I was from and that I had just finished my final exams at Cal. I think it only took a couple before I was a little buzzed and, in fact, knocked over my glass. Harris took this as a good time to suggest that we leave, and took me to his hotel
Harris told me that he was a salesman for a national insurance company and was in town for a week to attend office seminars. I liked his looks. He was wearing a three pieces business suit that looked like it had been bought at Sears. It was a Navy Blue pin striped suit with a power tie. It could have been a college tie, because it was a striped tie in dark blue and yellow. It could have meant he had graduated that he had graduated from Cal or Michigan.
The damp cold air on the street almost sobered me up as we walked across the street. The hotel was the kind of a hotel that catered to businessman, defiantly not a high class hotel. I remember the walls as a dull beige color, and a pull- down blind.
Without warning he kissed me on the mouth. I had never been kissed by a man like that before. He probably hadn't shave since that morning, so there was at least sixteen hours of stubble on his face. I could feel the stubble pressing against my mouth and cheeks.
I was over whelmed with emotion. I was not so naïve that I didn't know about homosexuals, but I didn't know for sure I could be attracted to a man that way.
I didn't resist as he started taking my clothes off. He was very careful about removing my suit and tie. He removed all of my clothes before removing his own clothes. The only things he left on was his socks and the garters holding them up.
He returned to kissing me with tongue while he felt my chest and tweaked my nipples with his fingers. I was sweating with mixed feelings. I felt like I should have stopped his assault, but it felt so damned good.
He wore rimless glasses and kept his boxer shorts on, pulling his dick through the fly (I'm not sure why he left the boxer shorts on, but I remember his body had some hair on it, and his head hair was light brown. He looked very sexy to me, and even today, if I see a picture of a man in boxer shorts and sheer socks and garters, I get turned on. The sheer socks were black, the garters were maroon. I'm sure the boxer shorts were plain white.
He had an arm around my shoulders reached down to play with my left nipple while he used his right hand to squeeze the bulge in my slacks. I had a boner screaming to let fly with a load of cum. He pulled my belt open. Then he unfastened the top of the slacks before unzipping the fly. I sat there motionless as he stuck his hand in the fly of my boxer shorts and pulled out my penis. He jacked me off until I had a large boner before he laid me on the bed and bent over to suck my cock.
I sat there not knowing what to do. I simply rested my hands on his head while he sucked my cock like an expert. Eventually I couldn't prevent myself from cumming in his mouth. I even warned him that I was about to cum, but he continued sucking my cock until I couldn't hold it any longer. I squirted my load of cum into his mouth. He swallowed it all, and sucked as well as licked my cock clean. While I sat thee recovering he finished taking my clothes off.
I lay there in all my naked glory while he got a tube of Vaseline from his pants and greased me up, and his penis. He didn't say what he wanted to do, but it was obvious to me that he was going to fuck me. He seemed to know what he was doing, so I just did whatever he said. I told him that I had never been fucked before. He lifted my legs up and rested my heels on his shoulders. His penis was neither small nor large, and I thought this is a nice guy, I'll probably enjoy this. He proceeded to give me a brisk fuck which I recall as painless. He must have prepared me well before fucking me. Maybe it wasn't erotically pleasurable, but it was a new sensation and I liked it. He even played with my cock while he fucked me. Eventually with on final thrust he buried his cock deep in my ass and stopped moving as he spilled his milk in my ass, after about 15 minutes, he came, and pulled out.
We lay there and talked. He said he was from Michigan, and would leave San Francisco the next morning, but he was willing to give me another fucking, because it had felt very good to him. He played with himself until he was hard again, and then inserted his dick into me again.
He lay behind me and lifted my right leg up as he slipped his cock back into my ass and fucked me again. He even jacked me off with his right hand until I squirted cum on the sheets before he deposited his cum in my ass again.
I thought surely he wouldn't want to give me a third cucking, but he said he thought he could. He said I had a cute butt that he couldn't resist, and that my rectum had just the tightness and length he wanted, so he wasn't going to waste the opportunity to fuck me another time. He got his penis hard a third time. He had me get on my hands and knees so that he could mount me like a dog mounts a bitch. He took it a little slower, but still intense. It took a while longer (I wasn't watching the clock). He managed to go in and give me a slow, deep fucking which I remember as particularly enjoyable. When he got to orgasm, he said there was no question that I should become a bottom. "You are perfectly built to be fucked, you can probably have your choice of men willing to give you a hot screwing" was what he said. He pulled out after that orgasm, and played with himself.
I thought to myself that he was a true sexual animal. I was lucky to find such a man to give me my first butt-fucking.
He didn't pull out of my rectum, although he said he had no more orgasms left that night. After a few moments, he said, "But I had such a good time, I'd like to put something else in you..." and I felt a surge in my colon and realized he was pissing in me. He took his time, and I remember thinking, this guy hasn't pissed all night, he's giving me a really memorable load, When he finished pissing, he still stayed inserted, telling me that he wanted me to enjoy having his output in me for a while. Eventually, he released me and I went to the bathroom.
After a while he came into the bathroom to see how I was doing. I remember putting my arms around the waistband of his boxer shorts and thanking him for all he had done. I asked him how I could attract another man who would be interested in fucking me.
He said, "If you walk around the men's gym locker room in only a jockstrap, and if you bend over so that you butt faces towards the opposite row of lockers you might find someone striking up a conversation with you.' He also suggested, "You could go to any of several men's rooms on the UC Berkeley campus such as the bathrooms in the Theater Arts and Music buildings, and stand up to a urinal and shove my pants and jockstrap down. Some man will step up to the urinal next to you and show you his dick, and you can decide if it's one you'd like to be fucked with. "Pay no attention to what the guy's face looks like or who he is, you're looking for a fucking, not a romance. If he seems to get hard looking at your butt, he's probably a good candidate. Start a conversation and arrange it to walk out with him. Don't be afraid to tell him you'd like to be fucked."
I thanked Harris for all he had done for me, and I left to get to my car, which I had parked in the underground garage in Union Square. As soon as I arrived there, I felt a need for a men's room, and released more of the liquid Harris had sent up my rear. Then I got my car, and headed over the Bay Bridge back to Berkeley and my room.
I was really satisfied, and I slept most of the day, which was already dawning. I had one thought, something I had wanted to ask Harris, but which hadn't occurred to me at the time. I noticed that I hadn't gotten two orgasms, but I didn't feel bad about that. Harris had made no attempt to get me off. He had just played with my cock to keep me hard. And I thought, that's Okay, because I liked what happened, and I would have been willing to repeat the session with Harris to all over again. He had told me he had a male partner back in Michigan, and he didn't give me his address, so I assumed he didn't want me to write. I was satisfied by the evening. I just wondered how to proceed from there. I knew I wanted to be fucked again, and I was hoping to find a man willing to ejaculate inside me who would also be willing to piss into me also.
I had laid there in his arms basing in the afterglow, because It had felt so good. Harris said, "You were made for fucking! You would be a fool not to seek out men willing to breed you!"
I applied for graduate status to earn my Master's Degree and it was granted. I deliberately avoided any physical entanglements with fellow students and professors, but I had a burning desire to have a warm cock in my ass.
Taking Harris' advice I thought about which bathroom to check out. I figured that the Theater Arts bathrooms would have more queens looking to be buggered, so I figured that the Music building would be a better choice.
I made my way to the building and entered the men's room and approached a urinal. I unfastened my pants and pulled them down below my ass and pressed my thighs against the porcelain bowl to keep the pants from falling down. Also taking his advice about wearing a jock strap, so when I pulled down my pants my ass was exposed. While I stood there pulling my cup aside to pull my cock out to piss, but I held it waiting for someone to take the urinal next to me.
It didn't take long, an older man with gray hair pulled back into a ponytail stepped up to the urinal and pulled out a very respectable cock. As he started peeing he asked, "Are you taking one of my classes? I don't seem to recognize you."
"No Sir...I'm not a music major. I just stopped by looking for a little action."
The man reached over and placed his hand on my ass. While I was peeing he stroked my ass and slid his fingers between the cheeks of my ass until he reached my asshole. Then he stuck his finger into my ass up to the second joint and lifted it up like a fishhook. "Is this the action you were looking for?"
"Yes sir"
As he stuffed his cock back in his pants he said, "Why don't you come up to my office to discuss what you're looking for?"
I quickly adjusted my cup and pulled up my pants and fastened them, as I followed him out. I took a good look at him as we made our way to the elevators.
He looked like the kindly grandfather type. He sported a neatly trimmed full beard as gray as his hair. He had mysterious looking light blue eyes. He was the same size as me, and dressed casually with a sweater over a sports shirt.
On the rid up the elevator we introduced ourselves, as he smelled the finger he had probed my ass with. His office was typical of any professor's office. His desk was pressed against one wall so that the window to the quad was on his left shoulder when he was seated at his desk. Book cases lined the wall behind him and there was an old leather couch next to the desk.
After he locked the door behind us he sat in his swivel chair facing me as he gestured to me to take a seat on the couch. "Now tell me Steuart what do you want? I want to hear you say it"
"I want you to fuck me, Sir!"
Stand up and remove your clothes, Son!"
I stood up and removed my clothes, down to my white sport socks. He had me turn around so that he could admire my body before he demanded, "Kneel on the couch with your face against the wall!"
I knelt on the cushion and crossed my arms on the back of the couch. He stood behind me while he dropped his pants and shorts. He used his hands to spread my butt cheeks to get a look at my asshole. He spit on my asshole as he positioned himself with his hard-on against my asshole. He slid his cock up my ass with a long stroke. He held my hips while he fucked me. He was good at it and his cock rubbing my prostrate through my rectum caused me to squirt cum all over the couch in front of me. After he deposited his load in my ass he slowly pulled out.
When I stood up and faced him, he kissed me. Our flaccid dicks rubbed each other. I knelt before him and took his cock into my mouth and sucked his cock clean.
When I stood up he sat down and handed me a box of tissues for me to clean the couch and my asshole. I even stuffed a couple up my ass so that my pants would stay dry until I got back to my dorm to clean up. Before I left he gave me a business card and told me to call anytime I wanted to get fucked again.
I noticed that the middle aged janitor for my building gave me a look every time we met that felt like he was undressing me with his eyes. One evening I entered one of the elevators and pressed the B for basement. When the door opened I noticed the infrastructure required to support. The heater and air conditioner along with the ducks covered with heat restart material. Further back was a work bench where the janitor could make small repairs to plumbing and such. There was an adjacent room that was the living quarters for the janitor. I found the janitor cleaning up the emptying the bucked used to wash the floors and the mop. When he became aware of my presence, he asked, "May I help you?"
I said, "I was hoping that we could be friends."
He washed his hands and dried them before shaking my hand. He still smelled industrial cleaning materials as he approached me. "Should be discussing this in a more private place?"
"That would be appropriate!"
He unlocked his door with a key attached to a retractable change attached to his pants.
When I entered his room it was a simple thing. Just a twin sized bed against a wall, a simple dresser that looked like an Ikea item. There was a closet with a mirrored door. I found it interesting that the only pinups on the wall were of naked sexy men. Seeing the pictures confirmed my suspicion about him.
"Would you like to fuck me, Bob?"
"Sure, Steuart"
"Can I rely on you fucking me on a regular basis?" I figured that because he was janitor he wouldn't go around telling people that I was a queen.
He started rubbing his hands all over my chest as he said, "I would be happy to satisfy your every desire!"
He started kissing me while we both started taking my clothes off. When I was totally naked he started removing his own clothes. He was about five-feet eleven feet tall. He was a little chubby but unlike Harris his body was almost hairless except for the normal underarm and pubic hair on the crotch. I was impressed with the size of his cock and a little apprehensive about him being able to fuck me without it hurting. Just the same I bent over and placed my hands on his unmade bed. Bob approached me and placed one hand on my butt while using the other hand to guide his un-cut cock to my puckering asshole.
I have to admit that it did hurt entering but as soon as he started fucking me it turned to pleasure. I even had an orgasm while he was fucking me without touching myself. After he finished I turned around to clean his cock with my mouth, then we settled down to cuddle and kiss while we played with each other's cocks.
As soon as he was ready he got on top of me and pulled my legs up to mount me in the missionary position and fucked me again. When he was finished I asked him if he could pee in my ass. He smiled down at me and let go with a stream in my ass, but he pulled out long enough to piss in my face. Afterwards I sucked his cock again, and he sucked my cock for another orgasm. At the end of that I got dressed and took the elevator up to my floor. Luckily I didn't run into anyone before I was softly in my room and took a shower.
Bob became my regular sexual outlet during the two years I spent earning my Master's Degree.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@yahoo.com