My Experience with Another Man

I was married young and had spent the majority of my adult years working and raising a family. My job required me to be away from home frequently and I spent the majority of my time engrossed in my work.

I met a man over coffee one day while working in Chicago. He was a fascinating guy, older, distinguished and for some reason had a draw over me. He talked about his expansive career as an educator and the various roles he held over the years. He was now 86 and fully retired but still worked as a volunteer in an older school but missed his active years. While I was fascinated with his stories I had to excuse myself and get to work. The man, Roger, gave me a card with his name and the address of his school where he told me he would be all day Saturday and to stop in and visit. I placed the card in my shirt pocket and rushed out.

That Saturday I was sending my suits out for cleaning and took the card out of my pocket. It had been days since I met this man and had almost forgotten meeting him. I put the card down and carried the laundry bag to the desk and went out for a breakfast trying to decide what to do since I was not used to having a day off. For some reason, the meeting with Roger kept popping back in my head. I thought about meeting him but figured he probably was just being nice and would not even remember meeting me. Anyway, what would we even have in common? I went about my day without much fanfare and arrived back at the hotel with a salad for dinner that I put into the fridge and sat on the bed trying to find something online to entertain myself for the rest of the afternoon.

It was close to four that afternoon when I got my car and drove to the address Roger had provided. It was already getting dark and a cold blustery Chicago day. The doors at the school were all locked and I decided to knock knowing Roger had long since left for the day. I was getting back into my rental when I heard a voice behind me and turned to see Roger in the doorway of the dark building. I turned around and ran inside as he closed the door behind me and locked it. He told me to follow him down the hall and he would show me his studio where he enjoyed painting. The halls were cold and dark and Roger led the way.

Walking I question my mental state, who was this man, what if he was a serial killer and my body was found in the icy waters of Lake Michigan in the spring? Finally, we reached an old wooden door frame with a large door with glass windows and a light shining dimly. Roger opened the door and I walked inside. I could smell the distinct aroma of oil paints. It was not much warmer inside the room. "Take your coat off and hang it up three on the hook," Roger said in an authoritarian tone. Almost instinctively I did as he commanded and then returned to where he was standing.

The room was something out of the sixties, a large high ceilinged room with huge six by six panes of glass, green dark tiled floors and dim fluorescent lighting suspended from the ceiling. Roger explained the school had closed twenty years ago and was sold by the city of Chicago to an art school that was barely functioning. Roger had numerous large canvases of male nudes around the room in various states of completion. He told me the school permitted him to keep and use the studio space in return for his facilitating several human drawing and painting classes each term for adults with interest in the arts. For some reason, my natural feelings of preservation were gone and I was mesmerized by this man who stood clad in a full suit with a bow tie. He was old fashioned and preserved my memory of the traditional school headmaster. I felt underdressed in my jeans, tennis shoes and a pullover shirt.

Roger seemed to possess a power over me. He pointed to a large wooden desk and told me to move and bend over. As a youngster, I had been spanked and paddled at school many times but now I felt powerless as I did as he told me. Without warning, I felt his bare open-handed swat across my cheeks. Despite my layer of clothing it still was sharp and burned. I did not move for reasons unknown but cried out a sharp "ouch!" Roger rubbed my burning ass through my jeans and then delivered another blow. I had not been spanked in years but for some reason, despite the pain, I was enjoying this man I did not know giving me a burning spanking. I had tears streaming down my cheeks as Roger asked me if I had learned my lesson. I had no idea what lesson but mumbled "yeah" and was smacked again until I finally replied with a "Yes, Sir."

I had taken an unknown number of "smacks" with Roger's open hand over the last fifteen or twenty minutes and finally stood up feeling a burning on my backside that I had not felt in years. As I stood my hands moved and began to rub my cheeks over my pants.

Roger told me to remove my shirt and without questioning him I did as he instructed. Once my shirt was off I stood shivering with my bare chest covered only by a thin line of black hair down my sternum. I then was told to remove my shoes and socks and was left standing on the cold tile barefoot. After a few minutes of Roger looking me over I heard him tell me sternly to remove my jeans. I don't know why but without hesitation I pulled my jeans off and lay them over the deskside chair with my shirt. I was embarrassed and my mind raced hoping Roger would not make me removed my underwear in front of him. I had always been very self-conscious of the size of my penis and did not want him to see it.

To my horror, my hopes were quickly dashed when Roger told me to get my underwear off. I could have turned and walked away, I could refuse, I could have left but instead I began to beg as I slowly and methodically slipped my underwear off my hips and down. I stood in front of this stranger now fully nude, humiliated and cold. Roger chuckled and said "boy, do you have a dick?"

I have always been small, soft I am less than half an inch while fully hard I am less than three inches. I also was fully shaved and smooth outside of the sparse chest hair, one due to genetics and secondly because my wife insisted on it. She always said I had a "teeny weenie" and said she could not see it when I had any pubic hair. I had been teased about my size in school for years and right now the feeling of intense humiliation was back full. Despite these feelings, I felt alive and aroused.

Roger had me removed his pants and revealed a nice, sizeable hard dick. He was hairy and somehow seeing the size of my penis and seeing my humiliation was growing even more erect. Roger once naked told me to show him my ass so he could see how tight I was. He instructed me to call him "daddy" and although it felt incredibly weird I did as he instructed which served to further embolden him.

Roger asked me as he had me bend over at the waist of his large cold desk how many dicks I had taken up my ass. I told him none and he smacked my ass and pushed his dick against my hole telling me not to lie to daddy and to tell him the truth. My ass stung and I again replied "none, daddy."

A sharp pain tore through me as Roger's dick pushed inside me and I cried out in pain. "I know you have been a little slut, now don't lie to daddy. How many dicks have you had up your man pussy?"

In tears, I replied "Daddy, I am not gay. I would never let a man put his pee-pee inside me"

Our banter continued for some time and I don't know how far Roger had pushed inside me but I felt like my insides were being ripped apart and finally, almost balling I for the first time, with anyone was honest.

"Daddy, please don't be mad, I have had seven pee-pee's inside me."

Roger already seemed to know the answer and he was no longer inside me. He kissed me and hugged me saying it was ok.

I told him how one year at a party during my senior year I got my pants pulled down in front of a group of buys and girls. I was embarrassed and tried to conceal myself but was overpowered by a group of the guys who displayed me to the others. I was bent over a bed and with the others, all watching, cheering and making fun of me seven of the guys took turns on me.

Roger told me he would love to help show me how wonderful sex can be when I was ready. A short time later I begged Roger to fuck me. This time he was soft, gentle and loving. Roger lasted a long time and finally came inside me. We ended up on a platform covered in drop cloths and I still had not climaxed. I leaned over onto my knees and took Roger's limp cock inside my mouth and began to suck him. I could taste his cum and he smelled like butt hole but I sucked him wanting to feel him get hard again. Finally, Roger got me laid back and alternated between sucking me and stroking me until I erupted in a massive orgasm. He spent time dipping my cum from my chest and belly and feeding it to me and I licked every drop from his fingers.

I got back to my hotel around 11 that night after we stopped and he bought me dinner at a fast food place. I had to work the rest of the week and Roger said he had dinner with his daughter and grandchildren on Sunday and asked if I was in town next week when he would have the school again. I flew out on Thursday the next week and we never saw each other again.

To this day I have never met, hooked up or played with another man. Roger offered to take my pictures that day but I declined, I often wish I had done it for the memories. This happened in 1997