Kipling F. Holliday IV By Bald Hairy Man
This is a story for adult men. It depicts gay sex. If this offends or bothers you, DO NOT READ IT. It is a fantasy and is not a sex manual, or a discussion of safe sex. If you have comments send them to rwinarch47@google.com
In a perfect world I should have had it made. I was a member of a wealthy and prominent family. My parents were well respected, and I was handsome and intelligent. After years of careful consideration, I have concluded that I was the problem. I do not know if there is a name for success crushing indolence and grotesque self-admiration.
I was smart, but I was so smart there was no need for education. Many people wanted to be friends, but all gave up on the effort. When you are as good and brilliant as I am, who needs friends, education, or work?
My family had owned Holliday's Department Stores. It was a chain of mid-sized stores serving mid-sized cities. When you needed a suit to wear on an interview, or a dress for a wedding you came to Holliday's. We sold good taste and quality at a good price. It was slightly expensive, but worth the price. I was a member of the fourth generation.
There was a problem. The Holiday's tended to have large families, three to four children per heir. I had 24 cousins in my generation. The fortune had to be huge to stretch to leave each of my cousins' wealthy. Holliday's did not evolve with the times so big box stores and nationwide discounts stores did us in.
Most family members were energetic and driven, two qualities I lacked completely. They tended to rise to the occasion when presented with a problem. I prefer to ignore problems. I made problems and left a mess for others to solve.
I did not share in the family tendency to reproduce. Let's just say girls weren't my thing. Some thought that was my only good quality. I never ruined a girl's life. People made allowances for me. My parents were good people, and most wondered what they had done to be stuck with me. I never was legally bad, but I left a trail of aggravation and disappointment in my wake.
The accident was the final straw. I was at a drunken party and sometime around 11:30 my car hit another car and then ran off the road. The death toll was seven. I was the sole survivor. I do not know what happened. I think I was in the trunk of the car, passed out during the accident. Two people at the party thought they saw me passed out and being carried to the car. That was the final police report.
No one believed that. They assumed the Holliday name was the reason I was not arrested for vehicular manslaughter. My father and mother left town and moved to Florida. Two of the victims were their best friend's children.
I was up the creek without a paddle.
People knew I was gay. They didn't know I had secret playmate forty miles away running an ageing motel on the edge of the Adirondacks. Davidson D. Davis was a sex crazed, dirty old man. He was also a nice guy. He tended to understand men with problems and short comings. He was incredibly nice if you were youngish, good looking and had a strong sex drive.
Self-awareness is not my strong suit. It took me ten years to realize I fell into that category. You might think he was taking advantage of my weaknesses. I and the guys he knew, thought we were taking advantage of him.
I met him when I was in college, and he was the Special Collections librarian. I went to the only college that would take me. The library was small, but someone had endowed the Special Collections Room and Davison sat around most of the day. I had a project that took me to his office. I think Davison got my number after five minutes of conversation. He seemed to have figured my sexual orientation as I opened the door. We hooked up.
I had been under the impression I was a sexual man of the world. Compared to Davidson, I was in Pre-K. He taught me a lot. Academically I was a dolt. Sexually I was a sponge. He was a sperm factory and at one time I thought half of my body weight was his cum. I was insatiable and he was in permanent heat. I made it through one and a half semesters before they kicked me out.
It turned out that the college's president was using the Special Collections endowment for his own needs, and Davidson was soon out of a job. An uncle had left him a secluded resort called The Peaks. The Peaks was the motel with a pool on the edge of the Adirondacks. It became a gay resort and home for lost souls.
It wasn't exactly a brothel. Sex was available, but it might have been more correct to think of it as a dating service. Davidson's friends hung around the Peaks until someone took them home to be a personal assistant or a pool boy.
The lost souls had a variety of problems, but all were blessed by an overactive sex drive. I planned to stay there until I could catch my breath and get my bearings. That took three years. I had no goal in life. I had one rule and guide to making a friend. He had to have a cock and want to use it.
If a guest was interesting and pleasant, we got together. If his cock was big or interesting, we got together. If he or I were board, we got together. If he was one of Davidson's friends, we got together.
Davison had a Friday night party for his weekend guests, and a Sunday brunch for the guests before they left. The weekends began with a cocktail party. I was the sparkplug at the parties. I ever quite sparked, but with a group of older gay men, a young man who looked good enough and was open minded was a find.
My first experience at the Peaks was with Milton. Milton did not mention his last name. He was 60 years old, a businessman, tall and in good shape. He was also a wilderness hiker. We talked some and didn't hit it off. He went off, but that night he came over to me.
"I was looking for someone to spend the night with. Are you game?" he asked.
"I didn't think we got along that well," I said.
"Let me level with you. I like to fuck. I like to go at it like a dog in heat. It is better for me with a guy I don't like much. Does that bother you?" he explained.
"I sort of bothers me, but not enough to say no," I replied.
"I don't like a guy who whimpers and cries," Milton added. I told him that wasn't a problem.
We went to his room. Milton was not a sadist or into inflicting pain. He and his cock were big. He knew what he wanted and was forceful. I like that. He used tons lubricant. His cock was one size too big for me, and that was perfect for me.
Academically I am a bit dense, but I learned a lot from Milton. He wasn't mean or nasty. He was driven, and that drive spent a lot of time up my backside. My ass was his cock's play playground. Sometimes, I was his sperm receptacle other times my ass was a cock garage.
He pulled out and took a shower. I joined him and sucked his relaxed cock. His cock was still drooling and that got me going. He took several breaks during two hours of fucking. During the breaks I felt empty; I missed his cock and seemed to fall in love with it.
It seemed beautiful to me. I thought about it pounding my ass, drooling precum exploding and filling my fuck tunnel with his man seed. I kissed his cock head in shower. I had fallen in love, not with Milton, but with his cock. Milton told me I had been good, all he hoped for.
That was downright strange. My strong suit had been leaving my parents, relatives, and friends disappointed. My Mom who tended to look on the bright side would say things like, "It not quite as bad as the last report card." Milton's "You were good," was high praise.
Later that week Davidson had a new boy, Eustace. He was a twenty-year-old guy who had left home at 16 to make his fortune. Fortune had eluded him. There is a Catholic saint of lost causes. Davidson was the gay equivalent. A trooper dropped Eustace off at the Peaks. Davidson took him to a doctor to make sure he was not contagious and then dropped him off at my room. Eustace became my roommate.
Eustace was malnourished, so I took him to the kitchen. He wanted potato chips and a chocolate bar; he had a burger and fries. I made him take a shower. Davidson had made him shower too, but Eustace needed more than one shower. I asked him what he liked to do. He replied he liked to suck cock. I pulled out my cock and asked him to suck me.
Eustace was the worst cock sucker I had ever met. It turned out he had been surviving on quick blow jobs and that enterprise had been a total failure. I told him to stop, and I'd give him lessons. I took another shower with him and gave him a real cleaning, combined with blow job instructions. I sucked him and his freshly cleaned cock was better than I expected.
I told him to treat the cock like a popsicle. Lick it gently and savor the taste. He tried that and complained I was oozing stuff. I explained pre cum, and the cock turned off piss during sex. He was relieved and told me my goo tasted good.
"Does cum taste as good?" he asked.
"It's different, much thicker and slightly bitter. I should warn you that if you are planning to make a living as a cock sucker, spitting out the cum is a turn off for most men," I explained. I had to explain that cum was not thickened piss.
"What should I do if a guy shoots in my mouth?" he asked.
"Pretend you won the lottery and gobble it up," I said. "You can swallow it or save it in your mouth and kiss him."
I did a little demonstration and saved his load in my mouth. I kissed him and poor Eustace went crazy. He loved it.
The next day, Davidson assigned him to the yard crew mowing grass. He discovered that his diet of Mountain Dew and potato chips was inadequate, and he ate actual food. He found out about my back story from the crew. That strangely improved me in his eyes. I was a fuck-up like him, so I was okay. He also realized I knew more about sex than he did. He was still hoping for a career as a toy boy in the employ of a millionaire.
Eustace was slightly more attractive than a normal guy, but his poor education was an obstacle for his plans. He thought he was a free spirit and did not want to ruin his freedom with education.
Eustace had never fucked, or been fucked, suggesting that his career as a call boy had not even got off the ground.
I was not a good guide to helping him learn the skills he needed for the vocation. While I rarely worried about what my playmate was feeling, I did know that unless he got something out of it, it would be a short session. I had figured out ways to make the session last, and I knew my playmate had to enjoy it.
Eustace seemed to understand that. He said he wouldn't mind fucking a guy. I had to explain that usually the man who pays picks the menu of activities. "If you tell a guy you want to fuck him and don't want him to fuck you, you've lost a sale." I explained.
Eventually I nudged my cock into Eustace's behind, and I expected him to seek out other ways to earn a living. I was wrong about that. Eustace's ass had been waiting for a good cock to fuck it. His ass was made to be fucked. He loved it.
I had to admit his ass was ideal for fucking. It responded to every motion, every movement. He loved it all, and I could tell.
After that success, he fucked me. I do not know if there is a phrase like ultra-Graceless or uber-Crude. I told him that maybe if he were a rock star or a multi-millionaire he could get away with his fucking technique, but it was more likely he would be on the front cover of a scandal sheet as the world's worst fucker.
I suspected Eubank thought a cock was for pissing, and once and a while you shot off. For me, the cock is a delicate, multifunctional sex organ. If you are smart it can be the Swiss Army Knife of sex organs.
I explained it was important to get paid, not have his customer call the police to report a rape. He understood that. I tried to figure out what to do with Eubank. He was dumb as a post and damn proud of it.
Two days later we had a new guest at the Peaks, Bradford Mullens. He was a fifty-year-old former high school coach and had inherited a fortune from a maiden aunt. He saw Eubank and liked what he saw. I told him Eubank was difficult.
"I was the football and hockey coach, but I should have been a Bronco Buster. Difficult guys are great once you get them in the harness," he explained. Bradford was a handsome man if you like domineering
, brawny musclemen with wills of iron. He liked Eubank and Eubank had no choice in the matter.
Eubank was unhappy with me but awed by Bradford. He moved into Bradford's room. Bradford never asked; he stated facts. Eubank obeyed. Bradford expected to be obeyed and was rarely disappointed.
A week later I met Roger. He was a bland, tall man who seemed to fade into the wallpaper. I sat next to him at the pool. His older partner had died six months earlier. He was lost. They had been together for 25 years. He was 45 years old and was not into bars. He was wearing swimming trunks, but the pool was mostly nude, so he stripped them off when he jumped into the water.
When he got out of the water, the eighth natural wonder of the world was hanging between his legs. That night it stretched my ass wider and went deeper that any cock that had fucked me.
Roger liked me since my ass was as receptive as his late partner's hole had been. Two months later I moved in with Roger. Roger was an investment advisor for the rich. He inherited a bundle from his late partner, so I thought I was set for life.
Roger had other ideas. He told me that he liked me and loved the sex, but 24/7 was too much. I had to get a job or go to college. I went to college as the lesser of two evils. I became an art history major as I thought it was the least demanding major available.
That was a mistake. I didn't do any research on the school. Art History was well known and highly respected department. When I took a course on Greek Art, I discovered I shared the ancient Greek taste for naked men. If you are a gay man who likes nude men, Greek art is the place for you. I also discovered a drawing class focused on the male body.
I had no interest in art at all. Naked men were different. I had a good professor, Ralph Dewing. He looked like a thin Grizzly Adams. Much to my amazement. I could draw. Even stranger, I could take advice on how to make the works better. While I drew naked men, but they struck people as non-pornographic.
Ralph was a direct man. "Kipling, you are an idiot, but you can draw!" It turned out that I could paint and sculpt too. Ralph later recommended that I keep my mouth closed and look moody. I could be a major artist if no one discovered my personality.
At the final student art exhibition, I won the top prize. That was good, but I had guys asking to buy it. Ralph told me to wait. My stuff would gain in value.
I no longer had Roger as my sole playmate. The artist models liked me too. They liked to look good, and my drawings and paintings made them look good. You would think that naked guy paintings would appeal only to gay men.
A man told me I didn't just show a nude man. My drawings gave a vision of the men's inner life. I knew most of the models had no inner life, but I did not need to tell anyone about that. The look of longing was often due hunger and the prospect of a Big-Mac for lunch.
One day the model did not show, and we had a substitute, Rusty Rabinowitz. I later found that Rusty was the product of only coupling of Misty Jones and Saul Rabinowitz. They never married, or had sex again, but Saul paid child support. Rusty inherited his father's tendency to be heavy and hairy. He was muscular but not toned. He had a working man's body, not a gym rat's musculature.
Ralph used Rusty to screw us up. Our models were smooth so we could focus on the musculature. Rusty's auburn body hair was thick and hard to draw. I just worked as fast as I could. One of my fellow students said I had a future in pet portraiture. It was snide comment, but when I stopped drawing, and stood back, it was a surprise. Rusty glowed. His hair was gold.
Ralph saw it. "Kipling you are a fucking genius; a fucking ideo-savant, but a genius." One of the women in the class worked for a local art gallery. She told her boss about it. A few days later he came to see my work. He wanted to do a one man show. He had a small gallery so that wasn't as grand as it sounded. Three months later my work was on display in a show named Nude but Not Naked.
I assumed it would appeal to only a gay clientele. The show was a success, with gay and straight people. I thought that was because they were not erotic. Ralph said it was because they were beautiful, well drawn and painted. Roger loved it. He no longer kept a boy toy. He had encouraged a talented new artist.
I was different too. Despite my own worst tendencies, I was good at something. I also discovered I liked it as much as I like sex with men.
I also came to know successful gay men. They were realtors, teachers, and bankers. I had a new social life too. There was another bit of good news. Someone found a phone video of me being dumped unconscious in the trunk of my car. The phone was lost in the aftermath of the accident. I was not driving the car. When the police reexamined the evidence the other car hit my car, not the other way around. That driver died in the accident, so there was no need to do anything. Problem was gossip, not the police. I was relieved. My mother cried when I told them about it.
A week later Rusty Rabinowitz's uncle, Abraham Rabinowitz came to see me. He said Rusty's father had died five years before and his mother had disappeared. Rusty was pleased by the publicity. People noticed him for the first time in his life. Rusty worked at the family a jewelry shop and this had improved sales. We had a friendly conversation. He told me Rusty liked me. I felt feeling he was checking up on me to make sure Rusty not being used.
Apparently, Rusty and Abraham shared other interests. How our conversation moved to my bedroom and became more intimate I do not know. It became more intimate after I skewered myself on his thick cock. He was hairy like Rusty and told me Rusty shared his sexual tastes. His cock had seemed short and stubby. His large knob rubbed my prostate giving it a massage.
I asked if he and Rusty were playmates. He said no. Rusty was afraid he would find out he was gay. "I did let him watch me as I frolicked with a friend. Eventually he and my friend got it on, and I left them alone. Rusty told me he appreciated that." I felt him shooting off in my ass.
"I'm sorry, I usually ask permission before I spread my seed," Abraham said.
"A cock has to do what a cock has to do," I replied.
Two months later, Rusty told me Abraham died a week ago. He was now the owner of the jewelry store and was upgrading it. Abraham told him we had met and got along well. "Usually when Uncle Abraham gets along well with a guy, he has sex." he remarked.
"Well, your uncle and I got along well," I said.
"This sounds stupid, but I would like to feel what he did," Rusty said.
"It was good," I said, "You knew he like to top?"
"I did," Rusty replied. "He told me you were that last man to fuck him." He paused, "Would it seem ghoulish to tell you I would love to feel what he felt?"
"Is there room in your ass for a load of cum?" I asked. Rusty began to strip.