Bankrupt, Downsized and Screwed 4 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, any comments send them to bldhrymn@yahoo.com
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Leo was tall, thin and handsome. He was a somewhat effeminate man, packaged in an intensely masculine package. He body was that of a young Marlboro man or Tom Selleck. His personality was that of Paul Lynd.
"Oh, I'm so sorry you broke up with your partner. Let me console you," Allen said in an impressively insincere voice. "Tell me where it hurts and I'll kiss your boo boo!" There was more laughter. Luckily, Leo had a sense of humor.
"My partner insisted on strict monogamy," Leo said. "He didn't explain the strict monogamy applied only to me. All the time we were together, he was trolling for a sugar daddy. I was a temporary cook and provided a place to live during the search."
"I am truly sorry," Allen said. "I didn't mean to insult you."
"Well, I'm not exactly a virgin and there were warning signs I chose to ignore," Leo said. "He was scum, but I was gullible." Leo looked around at the naked and semi naked men in the room. His eyes rested on the bulge created by Luke's monster. His face brightened. "Shit, have I died and gone to heaven? Is that fucker real?" Luke dropped his towel. There was another burst of laughter.
At the time, I thought it was funny, and that Leo was stunningly superficial. Actually, Leo was not one to cry over spilt milk. He didn't ever look back with regret, he just moved on. While he could learn from past mistakes, he didn't dwell on past problems.
"Exactly how interested in Grand Daddy sex are you?" Donovan asked.
"I'm not exactly sure," Leo said smiling. "I can say that no one over forty has ever rung my chimes. That may be because I'm not into older guys, but it also might be because I've never let them in the belfry." He went closer to Luke. "That thing is beautiful, can I touch it?" he asked.
"We do have an audience," Luke said. I noticed that comment wasn't a no.
"I've never been with a bunch of naked gay guys before," Leo said. "I tried a threesome years ago. It was okay, but never happened again, and then I got into this strictly monogamous thing.
"Strictly speak I have got into this "Do it with anyone who is willing" thing." Donovan said. "As long as it's with no strings attached and it's fun, I'm game."
"How has that worked for you?" Leo asked.
"I like it," Donovan said. "By the way I think there are five or six men here who would be willing to help you out." If you had been listening to the conversation you might think it was just a bunch of gay guys talking bull shit. As we talked, Leo's organ began to firm up and soon he was obviously hard. Men have to be men and soon several of us responded with sympathetic erections. Leo seemed to appreciate that.
The storm came and went and then came back again outside. The house was closed up and humid. We opened the windows for some air during breaks in the rain, but the air outside was just as muggy. The conversation had remained sexual and playful, until Luke became excited and his cock responded. That upped the excitement level in everybody. Most of the residents hadn't seen Luke erect. All appreciated the view.
Leo was explaining that his former partner's organ was long and thin, and he was afraid his asshole might have returned to is virgin state due to lack of stretching. Leo tended to sound like a gossiping hairdresser, and what might have seemed odd or peculiar seemed perfectly sensible as he spouted drivel. Even the more conservative members of our group, Luke and Melvin, were amused and not offended.
Freddy brought up some sandwiches and beer for lunch and the conversation remained ribald and funny. I went to the kitchen to make some more sandwiches. Leo came with me.
"The men here seem okay to me," he said. "Are they as nice as they seem to be? I'm in the mood for some fun, but I'd hate to bite off more than I can chew."
"They are all good men, even if several look a bit rough," I said. "They are all pretty vanilla, but they sure seem to like a lot of vanilla."
"I was fucked by both guys in the threesome I told you about. I loved it," Leo said. "I wouldn't mind sampling a few more cocks if they aren't too aggressive."
"I've never seen anyone doing anything painful here," I said.
"Even with the big guy?" he asked. "It's huge."
"Luke is careful," I said. "The only problem is the size of the thing. There is nothing you can do about that."
"I know it's stupid to even think about taking it, but Damn, I'd love to try," Leo said. We returned to the bedroom with more food and beer.
"When was the last time anyone other than your lover has been in your ass?" Donovan asked Leo. Leo took the question in stride.
"I think it may have been more than two years ago," Leo replied. "To tell you the truth, you men are all bigger than my usual playmate. That excites me, but it hard to decide which of you I should play with."
"I can answer that question for you. Try us all. Just think of us as a Whitman's sampler of cocks. I sure one of us can ring your chimes," Donovan suggested. Leo laughed and continued to chatter. We all noticed he did not object to Donovan's suggestion.
The men were talking and laughing. I took me a while to realize Marvin was sitting on Gus' cock. No one seemed to mind, and that included Luke. Leo went to Luke and they talked as we watched Marvin bounce on Gus's organ.
It's possible the afternoon turned into an orgy, but I'm not sure that is the right word. For a real orgy you need a perverse Roman emperor, some chained slaves and an open mind. We had the open mind part, but the afternoon was relaxed and enjoyable. There was a lot of sex and it involved everyone in the house.
While the sex became hot, sweaty and intense, it was also relaxed and casual. We became friends that afternoon, not just roommates. It was just sex in the best possible way. No one found an all-consuming passion, or the "One." I was surprised that while most of us had lost much of our former wealth and life styles, everyone was willing to share. That included everything for friendly advice, helpful hints and sharing their cocks, prostates and rectums.
In some ways, we filled the afternoon with several sexual experiments, and a number of discoveries. Leo discovered he liked grand-pa sex. He also found out his ass was still flexible and accommodating. He was born to please, or at least his asshole was born to bring joy. Freddy was the first to limber up Leo's under used sphincter.
I had known Freddy for years. He was a chandelier Queen, and had a taste for needy young men. Freddy thought of them as needy. I would have described them as manipulative. I had a few minor interludes with Freddy, but that was casual, all-oral and usually late at night after drinking a bit too much. I assumed he mostly bottomed for his boys.
Freddy did what Donovan described as a complete buff and shine on Leo's prostate. Of course, he was well beyond Leo's standard sell by date. Apparently, Freddy had double the endowment of Leo's former lover. It was a tight fit at first. Leo complained there was hardly any room in his tender ass for Freddy's organ.
Gus and Allen were trying to encourage Leo to take it like a man, then Freddy's battering ram discovered an unused back room in Leo's ass. Leo was shocked at first, and then very appreciative. It's not every day you discover a new place to feel pleasure. Leo was vocal and we all knew exactly how appreciative he was.
My sexual connections with Freddy had been quick and easy. We were friends but did not excite each other. I thought he had a short fuse. Freddy had an unusual sexual characteristic. Usually the more exciting your sexual partner is, the more intense the sexual activity will be. Of course that means the climax will be sooner. For Freddy, the climax was the end of sexual relations; he crashed. When a man excited him, Freddy could postpone the orgasm. He was able to grow his sexual fuse to extend the quality time. Middle-aged Freddy fucked Leo to exhaustion. Leo begged for some rest time.
Freddy was always courteous and accommodating and he pulled out. Marvin was watching the pair and when Freddy pulled out and rested on the bed, Marvin quickly straddled him and impaled himself on Freddy's pole.
Marvin was very much not Freddy's type, but he had never experienced Marvin almost prehensile sphincter. Marvin did a wild and sensual pole dance on Freddy's cock. It looked like a small man bouncing on a cock to casual onlookers. When you looked closely, Marvin's hips were in perpetual motion as he massaged the organ in his ass.
They broke apart so Freddy could go back to Leo. Poor Marvin looked empty. Marvin needed a cock in his ass to be complete. Luke just found out his cock was a joystick the night before. He thought it was too big for regular sexual use.
Marvin saw Luke standing alone. He bent over and presented his ass to Luke. Luke moved a few steps closer and then slid his entire cock into the willing hole. That caused gasps of amazement from the onlookers. To be more correct about that, some were amazed; others were envious.
I am not psychic, but I had a vision of Leo impaled on Luke's organ. Oddly, I felt an itch deep in my rectum. It was one of those odd itches that I knew I could never scratch. Luke pulled out leaving only his cock head in Marvin and then he slid it in to the hilt.
"Damn, that's beautiful," Gus exclaimed. I did a quick mental calculation and realized Luke's cock would be able to reach the itch. I was shocked I had that thought, but the idea began to grow on me.
Luke had seemed so out of the normal swing of things, I assumed he would have a difficult time adjusting to new activities, especially the sex. He wasn't at all imaginative, but he knew a good thing when he found it. Always polite and sensitive, Luke was also a fast learner.
I knew Luke enjoyed the way his cock felt in the tight confines of another man's ass. As his monster slipped in, he felt his partner react. Luke sensed where the good places were and was sure to return to them. After five or ten minutes in Marvin's ass Luke played him like a violin. It was lovely for both men.
Luke's cock turned Marvin into sex slave. Marvin surrendered to Luke's cock and quivered like sexually charged jelly. This would have been embarrassing if it hadn't been so joyful and uninhibited. Allen, Donovan and Gus watched were happy men. They were all masculine and macho men. As they watched Marvin quiver and Luke glow, they understood if they gave up on the macho attitude, the sex might get better.
Marvin later told men that he was afraid the men would look down in him for the unseemly display. That didn't happen. At first, I thought that was because everyone liked an easy bottom, but I enjoyed Marvin too. Anal sex is very intense for me and I tend to be tense and uneasy. I never know if it was going to be easy or difficult. That Marvin loved it so simplified things. You didn't need to worry that you were hurting him. You could concentrate on relaxation and pleasure.
The men had been uneasy about Whitey. While they had played with him, they didn't want to trespass on Luke's personal turf. When Luke slipped into Marvin's ass, they made a move on Whitey. Whitey wasn't very experienced, but he had liked everything he tried. Whitey was just a guy, much more masculine than handsome.
When I was younger, I went looking for handsome, beautiful men. To be truthful I wasn't looking for them, I was hoping one would fall in my lap and all would be well. As I aged, that hope turned into a fantasy. None of the younger men wanted a geezer, unless he had more disposable cash than I did.
When I moved into Freddy's house, I thought I was slumming. Not one of the men there, except for Allan, was conventionally handsome or beautiful. We were all plain, average, middle-aged men. Our main asset seemed to be willingness. As I watched Luke and Leo go at it, I realized that while these men weren't the men of my dreams, the sex was great and getting better.
Melvin and Leo were needy bottoms, and Allen, Donovan, and Gus tended to top. Whitey had a classic beer can style cock, thick and graceless. It wasn't huge, but it was a challenge for a tight hole.
Marvin and Luke broke apart and Leo was next in line to sample Luke's huge cock. I think it was a size bigger than Leo could take, but willingness can be the best lube. Leo didn't have a shy bone in his body, and he told Leo what to do. Most men just take what they get when they bottom. Leo told Luke when to go slow, push a little to the right or left and when to add lubricant. This made it easy for Luke.
Luke was a good-looking older man; Leo was a stud muffin. They made an odd, but compatible couple. Whitey looked on approvingly. Donovan was next to him talking. Gus came over to me.
"Whitey's interested in taking a trip deeper into the wild side," he whispered. "Donovan and I are going to be his guide. He wants to fuck. I was hoping you might help us out?" Gus leaned close to me. "We need a guy with a tight hole."
I was a bit taken back. I didn't think of myself that way. I must have been giving off the wrong signals. I said I would think about it. They went back to Whitey.
I was use to picking my own playmates. I never thought of myself as playing the role of a utility bottom. I was offended. I watched as Donovan put his arm around Whitey. All three men were getting hard, but Whitey's organ was still not fully erect. Whitey was just a workingman with a butt-plug style cock. What made them think I would help them out and take it?" I felt sorry for Whitey, but there was a limit. I stewed a little longer.
Suddenly, mid stew, I laughed at myself. In theory, I picked my own playmates, but in reality, I actually picked up damn few over the last decade. It wasn't that good for the last two decades. Whitey wasn't good looking, but he was a good man. There was no reason not to help him out.
I laughed at myself a second time. I wasn't actually playing Mother Theresa, being nice to the pathetic. His cock was looking really good, and I wanted to feel it in me. Whitey also tended to be reserved. I was hoping fucking would let him let go and we would go at it like dogs in heat. I walked over the trio of men. Donovan smiled.
Soon I was on the edge of the bed with Gus lubricating my ass and Donovan lubricating Whitey's cock. Gus took his time and eventually had two fingers in my ass. He seemed to be interested in my prostate and had me twitching in pleasure as he massaged it. Whitey then stepped up to the plate. It was thick, but the lubricant was thick too and it took only one thrust to get in. His cock was like a stubby cucumber. Once his was in, my sphincter clamped tightly on his organ.
Sometimes delayed gratification is good, but Whitey glowed as soon as he was in. "Damn, I didn't guess it would be this good," he moaned. He closed his eyes and cried, "Oh baby, it's so soft!"
"Oh baby you're so hard," I replied. I could barely think. Later I figured out the widest part of his cock must have been at my prostate and every movement was spectacularly pleasurable. My sphincter remained tight, and I essentially was jerking him off with my ass. All of the men clustered around us, offering helpful hints to Whitey, mostly dealing with how to make it last longer.
"Am I hurting him?" Whitey asked. I was gasping for breath.
"Look at his erection! It's not pain he's feeling!" Gus explained.
Of course, I was making a public spectacle of myself, but I was fine with it. While the men enjoyed watching, they were coaching Whitey. He obviously enjoyed it. Everyone was having a good time. I saw Leo watching and jumped when Donavan fucked him from the rear. He relaxed as Donavan's slipped in deeper.
It seemed as if being fucked in a group of friends was the most normal thing in the world. Whitey was trying to hold back, but he miscalculated and filled me with his man seed. He bellowed as he shot off.
When he pulled out, Gus took his place. My cum-filled ass was too inspirational for him and he shot off quickly. I loved the way the spurting sperm tickled my rectum. He pulled out and I relaxed.
"How are you doing," Allen asked.
"It's good," I replied. There was another cock at my sphincter. I was relaxed and had closed my eyes for a second. The cock popped through my sphincter and then began to slip deeper into my ass tunnel. This cock was filling, but with several loads of semen in my ass, it was fine. It went deeper and deeper. I suddenly realized it was Luke and his monster was already half in.
I didn't think there was any way his cock would fit on my hole, but by the time I formed that thought his cock was in all the way. I thought he was rearranged my internal organs at first. He made a few quick thrusts, and his cock found just the right spot. I wiggled my ass a few times and the right spot, turned into a spectacular spot.
Luke was very careful at first and he waited for me to respond before he moved. He jiggled and twitched a little. That felt good, and then he pulled out part of the way and then pushed in again. I had a sudden fear he would pull all the way out and leave men empty. I tightened my sphincter to hold him in. He seemed to like that and he began pumping hard.
The intensity of the sensations doubled and then quadrupled. After that, I don't know what happened. I lost the sense of myself. I was simply a part of his cock. Luke filled me completely. There was room for nothing more. I knew he was fucking his way towards a massive orgasm. I briefly worried there wasn't room for his man seed. A few minutes later I discovered that was not a problem.