Fits Like a Glove

By Robert Winthrop

Published on Dec 20, 2023

Gay

Fits like a Glove

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 winarch47@yahoo.com

Dad ran the Paramount Company, a successful development-real estate company. He was a smart man who had a knack for finding the next big development area. I am Carl, his youngest son. When I was growing up, my my brothers and I didn't see him a lot except at dinner, but he never missed a school play or conference with the teacher.

Mom ran the house. I had four brothers, but Aunt Sarah lived with us and she was nice. My bother's tried to get away with stuff sometimes. Mom didn't always notice, but my oldest brother Dan called Aunt Sarah Hawk Eye. He said she should have worked for the FBI. I was the youngest son, Greg, and I was calm and easygoing. That was not my brothers' characteristic.

When I got older, I found out that Dad had a trick to stay successful. He tended to buy out other developers properties, renovate them and sell them for a profit. His did this declining and slum properties. These became the next big thing and became part of reviving neighborhoods.

Some of the properties were not good enough to sell or rehab. He gave them to Uncle Bixby, his youngest brother. We called uncle Bixby uncle Bee. He was our favorite uncle because he gave us great presents at Christmas. There were noisy and potentially dangerous presents, and thus were incredibly attractive to little boys.

Looking back, I think my mother would have said, "Oh Shit, what is that man thinking." My mother would have never used that language, but the dangerous toys had a short lifespan. I think my father may have had a role in that.

Uncle Bixby liked the left over properties. Somehow he made a little profit on them. They were off Dad's books, so he was happy.

I was the youngest son and graduated from college with a degree in Engineering. My Dad retired and he and mom moved to Florida. I got a job with an engineering firm specializing in sewers and waste water treatment. I soon became a senior designer and had a good salary. I loved the job. I am a tree huger and an environmentalist. I thought sewage treatment plants did more for the environment than going to demonstrations,

My older brothers were married and had children. I didn't but no one noticed. Six grandchildren were all that my parents needed. My sexual interest did not include grandchildren or a women. I knew I was gay, but I was also shy and not prone to leave my comfort zone.

I was invited to have Thanksgiving dinner by uncle Bixby. My parents were California with an older brother's family, so I went to Bixby's house.

He lived in a fairly large house in a good neighborhood. I met five of his close friends. It took a minute or two to realize they were either gay or incredibly gay. I was surprised, but they were all friendly and easy to talk to. Dinner was traditional and very good. Mom was a good cook but in a family of eight, food was simple.

There was one guy there who was about my age, Bill. After dinner, he asked if I wanted to connect. I said I was uncomfortable in my uncle's house.

"Bixby's parties always end in an orgy," Bill said. "Everyone here is into sex big time."

Uncle Bixby must have over heard our conversation. He came over to me.

"I have assumed you are gay. I am really sorry if I made the wrong assumption," he said.

"You made the right assumption, but I don't know many men, and I am not really experienced," I said. Looking back I realize that I forgot to tell him I wasn't interested.

"Everyone here is friendly and experienced. If you need lessons, this is a good place to learn," Bixby said.

An older man named Charles came over to Bill. They were partners. It turned out Bill was recruiting me for a threesome. Bixby told them I wasn't very experienced.

"Bill and I have enough experience for three men," Charles said. "We're nice guys. Come join us and we give you some lessons. Don't worry, Bill and I are definitely not no pain, no gain guys. Man sex is for fun."

Charles was a big, muscular man. Somehow I had the feeling he expected to be obeyed. I went off with them to a bed room they called the bridal suite. A few minutes I discovered that Charles and Bill were both hairy muscle men sporting impressive sexual organs.

I was surprised to discover I was what they called an Otter, and my cock was impressive. Of course I knew I was hairy, but I thought that was a problem. In the dorm showers I had been called the missing link. That was not a compliment.

Charles and Bill were nice guys. I discovered that for me, a nice guy is good, but a well hung nice guy was even better. Somehow they were nice guys who knew how far they could go sexually. More importantly, they knew when I was ready to go further.

Bill was in his thirties, but Charles was in his fifties. I had never sucked an older guy. Charles' was into sex and his cock was responsive. I had tasted precum a few times, but that was seconds before the guy I was with was ready to shoot. He pushed me away and shot off. Somehow I knew that Charles wouldn't push me away and he would expect me to take his semen.

This shocked me. I was surprised that I was excited to be sucking this macho man and I wanted to taste and savor his seed as it squirted from his balls. Bill was sucking my cock. Just as I realized I was going to shoot off in Bill's mouth, Charles' load flooded my mouth.

I had thought that jerking off was as good as it got. Shooting off into a warm mouth as a hot man shot off into mine took me to a place I had never been to before. I felt like a rural hick who goes to technicolor movie for the first time.

I made another discovery. After a brief rest, I was ready to do it again. I had been with guys who usually zipped up and left as fast as they could go. I wanted more.

Uncle Bixby and Maximilian came in the room. They were naked.

"How are you doing Carl?" my uncle asked.

"It couldn't be any better," I replied.

"Have you had enough?" my uncle asked. "This isn't a marathon. It supposed to be fun not an endurance race."

"I think I just started. I loved it and want more," I said, "A lot more!"

"Would it be a problem if we joined you?" Maximilian asked. "I need to warn you, I like to be the first up a guys ass. That a big turn on for me."

"That's a bit much Max," Uncle Bixby said.

"You uncle is a big boy. His cock is a bit thick for a maiden voyage," Maximilian explained. "Mine is thin and long. It's easy to take."

"I can vouch for that," Bill said. "Max was the first up my ass and it was a good ride."

"Just good?" Max asked. The men laughed.

"Let's just say that when Max lets loose deep in my ass, it was like a fire hose. It was beautiful," Bill said.

"Are all of you guys into fucking?" I asked.

"The short answer is yes," uncle Bixby said. "We all top and bottom. It's a little like those old cowboy movies where a cowboy becomes a blood brother of an Indian. You could say were are all sperm brothers." All the men laughed.

Bill caught Uncle Bixby's eye and they paired off. Max and Charles came to me.

"I am going to gently slip my cock into your ass. I will eventually leave a present as deep in you as I can. It there is a problem and it hurts just tell me, I will pull out," Max said. "This isn't a contest. Think of my cock as an explorer. If I hit pay dirt, that's fine. If I don't, I am a big boy. It's not a problem."

"What if I don't like it?" I asked.

"That is not a problem either," Max said. "Explorers don't find the city of gold every time. Scientist don't expect every experiment to be a success."

Max was really experienced and I knew I wasn't the first virgin ass he had explored. Charles gave me a running commentary as Max's cock pushed it's way into me. Max's cock wasn't pencil thin, but my sphincter was the major obstacle and that was not a problem. His knob massaged my prostate and then he pushed deeper. Charles bent over so he could get a better view of Max's cock going in deeper and lick my cock. It was okay until Max began rhythmically thrusting into me. That was a lot more than okay.

It was exciting when Max gave up the fight to hold back and he began to shoot. The sensations were unlike any I had experienced before. I could feel each ejaculation. They were forceful and then diminished. He pulled out and all was well. Everyone except for Uncle Bixby left.

"I assumed you were gay, but I had no idea you were new to the scene," he said. "Are you still okay?"

I told him I was fine and then asked if this was typical of his friends and parties.

"I wouldn't say this is typical, but it's not unusual," he said. "Is this a new experience for you? Are you shocked?"

"I have a feeling that I should be shocked, but it was too pleasurable for that," I said. "It has opened up a new and unexpected world for me."

"Some men are looking for true love and a lifetime commitment," Bixby said. "This was just a bunch of guys having a good time. It's not deep, although some of us have been friends for years. You could say that sometimes we express friendship with sperm. Most of us are old friends."

"Bill wasn't that old," I said.

"Charles likes to help young men with their careers," Bixby replied. "Many of them think they are fine, and don't know they are on the wrong path. Charles knows that he is an oversexed wealthy man. He eventually guides the men to a better life. Sex eases the way."

"Anal sex as therapy?" I suggested.

"For years, I was looking for Mr. Right," Bixby said. "I have found Mr. Right Now. Mr. Right Now can be a nice guy and a good friend. I have had a happy life." He paused and then asked, "Does having Max's sperm deep in your ass make you feel any different about him?"

"I'm not sure. I sure felt good when he was shooting in me," I said. "Do you want to fuck me?"

"Greg, we have good relationship as nephew and Uncle. Replacing that with a top and bottom relationship is a risk I wouldn't like to take. Does that make sense to you?" I said it did.

"By the way, if I were to mention that you enjoyed this get together to you fellow guests, you might improve your social life. Would you like that?" Uncle Bixby asked.

"I think that would be nice," I replied. We returned to the other guests.

A week later I had a call at home from Charles. "Greg I was having a few friends over for dip in the pool and a barbecue. I was hoping you would come?" he said. "There will be some old fiends and some new friends."

I said I would love to attend. "Is there any thing I could bring?"

Charles laughed. "No one told you I am an importer of gourmet foods, I take it?"

"No they didn't. I was asking to bring coal to Newcastle?" I asked. He laughed.

"Bill is having some of his friends come. You should help to balance the old-fogy to hot-stud ratio," he said.

"I'm not sure I have even been considered a young stud before," I said.

Charles laughed again and said, "I can assure you that I am good at identifying young studs! Come by around three. Dress is very informal." I said I would be there.

I arrived at three and went to the enclosed pool area. Charles was clearly a prosperous man. Greg was in the pool with an older man. Both were skinny dipping. A heavy set man wearing a jock sat in the shade with another older man who was wearing a spaghetti strap tee shirt and nothing else.

I must have looked surprised. "I did mention the dress code is informal I hope," Charles remarked.

I smiled and said it was a hot day. We laughed. Charles leaned close to me. "The older guys are not old fuddy-duddies. They are most open minded. Several more men I didn't know arrived.

I was surprised when a man from my office appeared. John Dexter was a construction manager. He was every inch a construction type in boots, dungarees and a work shirt. It was unbuttoned to the waste exposing his hairy tanned chest. He was working on a job I worked on and we had been on a site meeting together.

He came over to me and said, "You look familiar."

"We were at the East Side Treatment Plant job meeting," I said.

"You didn't say much," he said.

"The head of the department doesn't want underlings to speak. He's in charge," I said. It turned out the president of the construction company was out of town, and he was pinch hitting. John explained a problem he was having, a pipe was over sized and wasn't fitting properly. I explained that the pipe was sized to accommodate future phase-three expansion. I had added two inches to the diameter of the pipe to be generous in case the addition was larger than anticipated.

"It is a lot of work, but it makes sense now," he said. "Is that why the east wall footings are over sized?"

"There is to be a fifty-foot clear span addition attached to the east wall work," I explained.

"It would have been nice to know that," he said.

"One of the city council members didn't want the addition. He seemed to think if we showed it, it would have to be built. The council wouldn't approve the project if the addition was indicated," I said. "I can get you a copy of the master plan drawings if you hide it from public view."

"That would be helpful," John said. "It's hot here in the sun. Do you swim?"

"I do but I didn't bring my trunks," I said.

"As the said in the Beverly Hill Billies, this is a cement pond, but I've never seen anyone do anything other than skinny-dipping here. We're all boys," he said.

I glanced around and saw one woman. John saw her. He leaned closer. "That little lady has a cock. There is no need to be shy." He said. We stripped and jumped into the pool.

Shortly after we made the jump, most of the other guests stripped and entered the pool. John and I were a minor focus of attention. I was considered to be new meat, and John was rough trade. Let's say that construction workers were rare and exciting to this group.

It took fifteen minutes to notice fondling under the water and another fifteen minutes for cock sucking to be obvious. John and I both had admirers. John was with a man I knew as Judge Watson. He was a known as a strict judge. He specialized in corporate crimes. He seemed to like John a lot.

I was with the woman with the cock. He was Frank or Francis depending on his mood. He was naked so he was a well known interior decorator. I later found out his specialty was emergency decorating. When another decorator fucked-up or left town after pocketing the fee, Frank could save the day.

He actually worked for my firm. When you are spending millions on a project and the office looks like a World War II temporary building, Frank came to the rescue. He could produce a simple, attractive professional office. It would be attractive but not flashy. He could also do flamboyant showplaces when required.

Naked he was obviously Frank and not Frances. He was smooth, muscular and hung. He knew who I was. He asked if I preferred him to be Frank or his alter ego. I said Frank was good for me.

"I've known your uncle for years. We have never exactly been lovers, but my prostate and his cock are almost civil partners," he said.

I laughed, "You get along well?"

"We are old fiends and sexually compatible. Living with me takes a lot of effort. I'm better in small doses," he explained. "Bixby told me that an evening with me is fine, the entire night is too much. I usually leave after the orgasms."

"Does that offend you?" I asked.

"It did, but the truth can be a harsh mistress," Frank said. "I have many friends, but your uncle is my best friend. I need to be truthful with you. My interest in you is not platonic. My interest in men is never platonic. I would love to trade orgasms with you. I am polite but my long term objective is to feel you ejaculating in my ass."

John came over and said his friends wanted to meet me. I asked Frank to give me a rain check. He understood. I went with John to meet Judge Watson.

"Both your uncle Bixby and Frank thought I should meet you. Bixby is an old friend," the judge explained. "I've known him since high school. We had a lot of fun back then. Bixby told me we share some of the same interests." He leaned closer to me ans whispered, "Bill and Charles thought we would get along well."

I smiled and said, "I lived here until I went to college. Since I've been back, everyone seems so friendly. It has been unexpectedly pleasurable."

"I have a few intimate friends. We have what you might call high intensity interludes. No strings, but very pleasurable encounters. Please call me Adrian," the Judge said. "It's getting too hot here for me. Charles has a room for the former chauffeur next to the garage that is cool. Would you men like to join me?"

"That is fine with me John said. The four of us went to the chauffeur's room. Adrian got on the bed. John fed him his cock and I began to suck Adrian's cock. His cock began to grow and so it was an impressive organ. A minute or two later his cock began to ooze and I could taste his excitement. He was an older man but he definitely was getting in to it. A little later my cock was rock hard and I was getting into it too.

Fifteen minutes later Adrian was easing his cock into my ass. It felt bigger than it looked and suddenly it hit a spot I didn't know existed. It was beautiful. I tried to spread my legs so he could go deeper and his cock would intensify the sensations. I don't know exactly what happened but wave after wave of sensations spread through my body. Judge Adrian Watson had discovered the perfect place in my ass.

I was deeply embarrassed by my feelings. That was made worse when I realized he was having the same feelings. I didn't want to be a boy-toy. Watson knew my father and fucking his son was one thing. Getting intimate emotionally was another. A few minutes later the situation got worse. He had a spectacular orgasm, and I was wondering how I had managed to live without his sperm flooding my ass.

Next: Chapter 2


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate