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Pool Party - Jump Right In


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Last summer, I was short on time and money, so for vacation I bought day-passes to a nearby gay resort. Known for its high sexual energy, the place has a clothing optional, pool, patio and outdoor bar. To make the most of my time, I planned to squeeze in as much fun - and fucking as possible. This would mean not being as picky, or indecisive, or cautious as I usually am.

 

I arrived at the inn early and chose a lounge chair in a sunny spot by the pool. I kept on my t-shirt and baggy shorts and settled down with a book. As guys showed up I would sneak occasional glances as they stripped down to their swimsuits and oiled up. Within two hours the place was packed.

 

An older pair of black muscle daddies took the two chairs on my right. One of them stared right at me as they both completely undressed, then quickly donned matching red Speedos. Their cocks were two of the biggest that I’d ever seen. I was glad that I had peeked. I mentally put them on my “yes I would” list, but since they were a couple I didn’t hold much hope. They introduced themselves as Max and Troy, but soon put on earphones to listen to music.

 

A group of six friends, three bears, two cubs and an otter took over most of the remaining empty lounges to the left and behind me. They were loud and friendly, greeting me, Max and Troy, and everyone else that looked their way. There were too many to keep track of, and their personal interactions made it difficult to determine if any were couples. The biggest and oldest bear had extensive tattoos on his arms and was wearing a pair of white boxers. They all joked how he had lost his swimsuit in some trick’s room the day before. The otter and the other bears wore baggy swim-trunks. One of the cubs wore pale blue Speedos and had a huge package. The other cub got completely naked and had a beautiful, furry bubble-butt. They both were mentally added to my to-do list.

 

After settling in, they continued joking and laughing. At least one of them always seemed to be talking. They were quiet only one moment: when I stood up and removed my shirt and shorts. I’m hairy and a little on the short side, but I work out, so I’m what you’d call a fit cub. I was wearing a black, mesh thong that left nothing to the imagination. I guess they liked what they saw, because I heard one of them grunt “Woof.” Max also noticed and I saw him motion to Troy so that he could check me out too. Like I said, I needed to make the most of a short vacation.

 

The otter, who sat to my left, seemed to be the leader. He was cute with wavy brown hair and fine blonde hairs all over his body. He was also the funniest. I was trying not to listen, but after one particularly funny remark, he caught me laughing at his joke. He gave me a little wink and flashed a big smile that moved him to the top of my “yes I would” list. He extended his hand and introduced himself as Peter. We chatted a few minutes and he offered to buy me a drink.

 

We spoke for quite a while at the bar. He was overly sure of himself and pushier than I usually like, but he was easy to talk to and we had some common interests. Before finishing our second drinks, he brought up the subject of sex. We seemed a good match. (He: total top. Me: versatile bottom.) Both of us hated condoms and both of us had last tested negative. He suggested that I join him and his friends for dinner and dancing later that night. I accepted, sure that the evening would lead to something more.

 

When we returned to the pool, the naked cub with the beautiful butt was sitting and chatting with Max and Troy. The rest of Peter’s friends were in the pool. Judging by all the discarded swimsuits, they were skinny dipping. Peter and I stripped naked and joined them.

 

They were standing in shallow water that came up to my nipples. It was hard to see under the surface, but I suspected some of them were jerking off. Peter introduced me and space was made for us to join the circle. But instead of shaking my hand - their hands were all over me; squeezing my butt, pinching my nipples and tugging my cock and balls. Peter pulled me close and French kissed me. Someone else slid a finger up my asshole and worked it around roughly. When I squirmed Peter said, “Just go with it babe. Don’t make a scene,” and stuck his tongue further down my throat.

 

“All lubed and ready now boys,” someone said behind me and removed his finger. “Let’s break this cub in.”

 

I was a little scared, but my dick was rock hard, so I didn’t protest, especially as Peter’s kissing muffled my cry as somebody jammed his giant cock up my hole. Luckily, he held it there a moment while my ass got used to the intrusion. What had started as pain quickly turned to pleasure and my whole body relaxed as the cock slowly moved back and forth in my ass.

 

“You like that dirty dick fucking your butt?” Peter asked.

 

“Oh, yeah,” I managed to say.  Dirty?

 

“Good. We’ve got lots more if you’re up for it.”

 

“Yes please.” I said more turned on than I’d ever been. I was a little nervous having sex in public. I looked around to see if anyone was watching, but all eyes were distracted elsewhere. I followed their gazes. Max and Troy were spit roasting the naked cub out in the open for all to see.  “I’m getting close,” a voice said behind me.

 

“Breed him,” Peter said.  The voice behind me softly moaned as the dick in my ass pumped and unloaded deeply.  “That’s one,” Peter said “Next.”

 

The spent cock slowly pulled out and another took its place. Peter worked my nips and between kissing, he talked dirty to me, almost whispering. “Fucking slut, I knew you were a dirty cum whore the second I saw you. You like taking dirty cocks, don’t you? Gonna get you all charged up before the night is done.” The cock in my ass fucked faster and faster as Peter’s talk got nastier. Without losing pace, I felt the dick spasm in my ass and heard muffled grunts in my ear.

 

“That’s two,” Peter said. The dick in my ass softened a bit, but maintained its size.

 

“Milk that dirty dick,” Peter told me. “Milk every fucking drop.” I squeezed my ass muscles and massaged the cock until it pulled out.  Peter asked “Who’s next?”

 

From behind, a pair of tattooed arms wrapped tightly across my chest and lifted me several inches off the pool floor. Peter reached underwater and guided the big bear’s average-size, but rock hard cock into my cum-lubed hole. Peter kissed me some more, sandwiching me tightly between their naked bodies. They both talked dirty in my ears as the big bear fucked me slowly. The cub with the big package moved in to help hold me up and rubbed his impressive cock against my leg asking “You like that Daddy-dick fucking your ass?”

 

“Oh yes.”

 

“You ready to receive Daddy’s gift?”

 

“Yes please.”

 

“Yes please… what?” He fucked faster.

 

“Yes please Daddy, please give me your gift.”

 

The big bear made no attempt to be quiet. He grunted and growled with each spurt of cum shot in my ass. A few curious heads turned our way, but a moment later their attention was lost as Max cried out loudly and shot his load up the naked cub’s bubble-butt. The crowd of horny men cheered and applauded. Max pulled out and high-fived a couple guys, but the show wasn’t over. The cub turned around and offered his ass to Troy.  “Squeeze tight,” Daddy told me. “Don’t lose a drop.” His cock fell out as they slowly lowered me down.

 

“Next,” Peter said.

 

“I’m going to enjoy this,” the cub with the big package said as he positioned himself behind me. By now I was loose enough and lubed enough to take most any cock, but as the cub’s dickhead push against my hole there was resistance. A few hard pushes and the head entered with a pop that made me cry out.

Peter smiled an evil grin asking, “Feels good, doesn’t it?”

 

“Oh…” was all I managed as the fat dick inched its way in.

 

Then, “It’s too big, too big,” I said when I thought I couldn’t take anymore.

 

Dizzy from the pleasure, I almost missed it when Troy came in the naked cub’s ass and the crowd again cheered in approval.  “I’m only half in,” the cub said.

 

“Keep going,” Peter instructed.  I can honestly say I was grateful the cub had been slowly withdrawing from my ass, and I expected to be relived when he popped-out, but instead he pushed back in again. Then almost out again and back in. Out and back, each time going just a little deeper, each time stretching my innards a bit more. After a few minutes I felt the cub pressing up against my back. “I’m balls deep,” he said.

 

“Go for it,” Peter said.

 

The cub began thrusting harder, but now he didn’t pull out much at all, just an inch or two. I leaned on Peter to brace myself against the increasing force. The cub fucked faster, but deep in my guts. A wave of pain and intense pleasure filled and warmed my body. I couldn’t keep from crying out and the crowd around the pool was now watching me.  “I told you not to make a scene,” Peter said. “Now everybody’s going to see you take your fourth poz load.” I looked him in the eyes, but couldn’t say anything as grunts of pleasure escaped my mouth. “That’s right slut. You never did ask them their status. Nothing I like better than watching poz peckers breeding neg hole.”

 

“I’m gonna cum,” the cub shouted. The crowd started chanting, “Shoot! Shoot! Shoot! Shoot!”

 

“You gonna take that dirty load?” Peter asked.

 

“Yes!” I almost screamed. “Give me that dirty fucking load!”

 

The crowd was stunned silent. The cub bucked and thrashed in the water as he filled my ass deep, loudly grunting with each pulse of his cock. He must have shot ten times. The crowd began to cheer and applaud before he had stopped shooting. He left his enormous cock inside me as he caught his breath. The crowd broke up and moved along.

 

The cub that had taken Max and Troy’s loads got an oversized butt-plug out of his bag and threw it to Peter. Peter held it in front of me and said, “You wouldn’t want to lose a drop now.”

 

“No,” I said, “I wouldn’t.” and “Thank you.”  The cub pulled his giant cock slowly out of my ass. I felt empty for just a second then Peter slid the butt-plug inside me and I was full again. Peter kissed me softly.  “Thank you,” I said, “For everything.”

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Sounds a lot like a sex motel I stayed at in Palm Springs one New Year's Eve. I'd never been part of an orgy before, but the whole place--pool, lounge, and most rooms--were a total fuckfest that went on until dawn. Singles, couples, locals all joined in. It was wild.

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  • 5 weeks later...

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