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Jail and Bail


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All I'd really known about the pub's Friday Nights was that they were the night that it more or less transformed into a bear and leather bar, but that a little guy like me could still go without feeling completely out of place. When I got there, and saw it was packed with big guys - the kind of big guys that I adored - I was very happy I'd plucked up the courage to head out on my own. I hadn't thought it was going to be so incredibly busy at the pub - the one time I'd gone before, with friends from university, it hadn't been anything like this. I was nervous, but with a big crowd, I figured hiding wouldn't be a problem.

I paid my entry, got my stamp, and then saw the big sign over the coat check. "Jail and Bail!" Underneath that was a picture of a guy behind bars with a big grin on his face, and a note saying all the money was going toward local LGBT outreach. I realized I'd come on an event night. That was fine by me, and given the plethora of big hairy guys on display - seriously, this was a lovely gathering of bears, and this wee fellow wasn't going to look a gift horse in the mouth - I wasn't going to bedgrudge a slightly higher than average cover charge.

At the coat check, though, a guy in a black "STAFF" t-shirt peeled off a sticker and smacked it onto the back of my shoulder. "What's that?" I asked. "Your number," he said, putting another sticker on the front of my chest. I must have looked confused. "For a buck, someone can send you a message - you just find one of the wardens and they'll give you the paper and a pencil and deliver the message to the number you write down." "Ah," I nodded. "For twenty, you can send someone to jail. You stay in jail for fifteen minutes, or until you bail yourself out - which is any donation you want to make." "Jail?" I asked. He just smiled. "Upstairs."

Okay. I hadn't gone upstairs my last time here, but that seemed fine. "You want to break some cash?" he asked, gesturing at a box in front of himself. There was no harm, so I turned a ten into singles, and then went further into the bar. There were more than a few guys in leather, which definitely turned my crank, but mostly the room was filled with stocky guys with beards. I went and ordered a beer, and then found a spare spot against one of the walls - all the stools and booths were taken - and settled down to drink and a look around. I spotted some hot guys. Most of them at least a decade my elder, I figured, but it was fun to look. One, at the bar stool with a friend, was a wide-shouldered bearded guy whose sleeveless black shirt showed off the impressive amount of dark hair that trailed all the way up his forearms and a bit above his elbows - and the arms themselves were thick with muscle. On the back of his shirt, I could barely make out his number, and was considering finding a "warden" to send him a note when he turned and saw me staring at him. My face went beet red and I turned away, tipping my bottle back and feeling stupid. When I finally got up the nerve to look up again, he was still looking at me - and beside him, his friend (who kind of reminded me of Mr. Clean - bald head, big chest, tight white shirt) leaned in and said something, and they both laughed.

I looked away again, studiously avoiding looking back until I was done my beer. By that point, they had moved-on. I sighed. "Should have sent a message," I muttered. Beside me, someone said, "Which one?" I turned. The guy leaning against the wall to my left was looking at me, waiting for my answer. He was taller than me (not difficult) and had a neatly trimmed beard, a ball cap on, and a khaki green t-shirt. He was pretty fit, though he was thick enough in the middle to more-or-less be a bear. "The one with the beard," I admitted. He nodded. "Hot guy." He offered his hand, and introduced himself as Steve. "You been to a Jail and Bail before?" I shook my head. "Nope." "Well, I'm pretty sure the jailer took them both off to jail. They'll be back out in a little while, if they want." "Oh," I said, sure I was blushing again. "Did you catch his number?" Steve asked, smiling. I nodded. "Thirty eight." "Hang on," Steve said, and pushed away from the wall. "Be right back." I watched him move through the crowd, approaching a guy in a dark blue cop-like uniform with mirror-shades and lean over to ask him something. The guy looked at a clipboard, and nodded. Steve handed him some money, and came back bearing a small handfull of paper slips and two pencils, saying "I was right. Number thirty eight is upstairs in jail. Here," he said, handing one of them to me. "Write him a note for when he gets out." I laughed. "I have no idea what to say." Steve smiled. "Tell him you want him to maul you." I laughed again. "Oh my God." Steve's eyebrows rose, and he smiled mockingly. "But that's what you want, isn't it?" "Right," I said, shaking my head. "I could never write that. Oh my God." He tapped his pencil against his lip. "Tell me the truth. You're a chaser, right?" I'd heard the term before, of course. Bear chasers - guys who liked bears, who weren't bears. I nodded. "Yep." "I take it I don't measure up?" he said, with another mocking smile. I blushed. "Oh, no. I mean... You're really nice!" He laughed, and shoved my shoulder. "Don't worry about it. I'm probably almost as big a bottom as you are." He raised an eyebrow. "You're totally a bottom, right?" I blushed. Laughed. Nodded. He nodded. "Of course. Well, I think you should just be honest. Tell him you want his big ol' beardick up your butt, as soon as possible, please and thank you." I shook my head. "You're awful." "But that's not what you want?" he asked. I rolled my eyes. "Well, I guess you're right: it's totally what I want." Steve's smile was smug. "What are you going to write, then?" I thought about it. "I suppose I could ask him if he liked guys like me?" "Bottom sluts?" Steve asked. I shoved him. "Little guys." "You calling me fat?" He narrowed his eyes. I laughed again. Steve was fun, and I definitely felt more comfortable now that I had someone to chat with. "No. But so many guys like him don't like guys like me." Steve nodded. "Fair enough. Go with that. Only don't be so high school. Try... 'Any chance you'd be interested in the naughty boy next door?' or something like that. Something not so bland." He waved a hand. What the hell, I thought. It wasn't likely the bearded stud was, so what did I have to lose? I wrote down his message, put the number thirty eight at the top of the note, and my own number at the bottom. I also added, 'Didn't mean to stare earlier, but couldn't help it!' for good measure.

Steve was writing some messages of his own, and glancing up to look at numbers as guys walked by. I admired his confidence. When he was done, he held out his hand, and I reluctantly gave him the paper. I felt my own confidence drying up. "Back in a sec." He left, handed the papers to one of the wardens, and came back with two beers. We clinked bottles and drank, Steve nudging me every time a bear walked by that he found attractive - he liked them even bigger than I did, I realized pretty quickly.

I spotted thirty eight a few minutes later, and saw him looking around. When he glanced out way, I turned my head to face Steve, feeling my face burn up, but Steve raised his bottle in the thirty eight's direction. "Stop it," I hissed. Steve laughed. "Oh shut up. He's smiling." "He is?" I asked, and turned to look. Thirty eight met my gaze and was smiling, yes, but I wasn't sure it was entirely just friendly. Yow. Was it just me, or did he almost seem... hungry? I shivered, and looked back at Steve. "Oh wow." "Yeah, he's definitely enjoying the view." "Now what?" Steve laughed. "I guess that's up to him." I got my answer a few minutes later, when a jailer walked up to me. They were really playing up their role - there was no smile on the man's face, and he was all business as he handed me a small folded piece of paper. "You have a letter, prisoner." I grinned, and took the paper. I looked down first, and saw that it was from number thirty eight. Then I looked at the message. "See you in a few," it said. I blinked. "You're coming with me," the jailer said. "Pardon?" I asked. "You've been found guilty," he said, showing me a twenty dollar bill, which he tucked into the front pocket of his shirt. I laughed. I was being sent to jail! The warden took my arm - I laughed a little nervously - and he led me towards the stairs. "Drop the soap!" Steve called out. I felt my face turn beet red. As I passed number thirty eight, I couldn't help but glance at him. He nodded and smiled - that same deep smile that made my whole body shiver. I was just about at the stairs when I saw another jailor stop by him, and take him by the arm.

The "jail" wasn't the entire second floor, I realized. Once we were at the top of the stairs, the jailer led me across the dance floor - I hadn't known there was one - and to the back wall of the bar, where there was a long chain that had been fixed to both sides of an opening. The jailer pulled out his little clip-board, wrote down my number, and checked the time on a glow-in-the-dark clock that was beside the opening. Beyond the open doorway there was another wall - it seemed to be a hallway running perpendicular to the open doorway - like the way some bathrooms didn't have doors, but blocked the view of what was inside. He reached out an unhooked the chain. "Your sentence is for fifteen minutes. You can bribe yourself out at any time." He gave me a little shove, and I stepped through into the "jail" area just as number thirty eight came into view behind across the dance floor. "Enter the cell," my jailer said. With a quick glance behind me at thirty eight, I walked left around the wall that formed the barrier to the jail.

As soon as I rounded the corner I realized that the "jail" was a dressed up backroom. It was larger than I expected, a rectangular room with very dim lighting (the bulbs were red) and inside I could see men in various states of nudity moving or standing. One guy was completely naked while another was on his knees in front of him, giving him a blow job. A few were just making out. And in the furthest corner, there was a bear who was definitely fucking another bear who he had pinned against the corner, if the motion of the bear's hairy ass was any clue. I froze. A couple of the people looked up as I came around the corner, though most were just watching the shows all ready in progress. I'd never been anywhere like this, had never seen - or smelled - anything like this. The place smelled like sweat and salt... I shivered. Fifteen minutes? Oh my god - they were having sex in front of me.... That's when a hand took my shoulder, and I nearly yelped. I turned, shaking, and saw thirty eight beside me.

"Hey," he said, and leaned in very close to me. Up close, I could see that he was older than I'd guessed, but that he was definitely in good shape for his age. His beard had a few threads of grey in it, and he was way taller than I'd thought. I had to tilt my head a little as he stepped towards me, and backed up on reflex. His hand still held my shoulder. I hit the wall with a bump, and he smiled down at me, closing the gap a little further. Oh my god, I was in a back room with him. "Hi," I said. It came out a little squeaky. He leaned in close, and his beard tickled my ear as he spoke. "Your friend was right. You're shy." I blinked. "My friend?" "Yeah. Your friend. He sent me a message. Said you were too shy to ask for what you really wanted." He was pressing his chest against mine now, and unbidden, my hands came up and sort of awkwardly gripped his waist. He leaned back a bit, meeting my gaze. Steve. Steve had sent him a message. Oh. My. God.

I guess he could tell when it clicked. He smiled, and his teeth were a little eerie in the red light. He leaned back in again, pressing the whole of his body against mine, moving his bearded mouth to my ear again, so close I could feel the warmth of his breath. "Something about a big ol' beardick, and your naughty boy butt?" My whole body shivered, and he had to have felt it. Also, my cock got rock hard, and I knew he could feel that, since he'd pressed one of his legs between mine. More to the point, I could feel his own dick against my stomach, even through his jeans and my shirt, and holy shit, I couldn't believe any of it. "Oh," I said, and then his tongue flicked my ear, and I repeated myself while my whole body shook. "Oh!" "Turn around," he said.

I was shaking, but when he took my shoulders and pulled me, I obeyed, turning around to face the wall. I pressed my forehead against the cooler stone, breathing heavily. When his body leaned back against me, his hard on was all the more obvious. His held my shoulder with one hand, and the other rubbed against the back of my neck, then up the side of my face, cupping my cheek for a second before he pushed his thumb into my mouth. I sucked it. He chuckled. "Yeah, you are a naughty boy, aren't ya?" I sucked again. He laughed. He pulled his thumb from my mouth and slide his hands down my arms, taking my wrists and then pulling my hands up and placing my palms against the cool stone wall. His hands pressed enough for me to realize he was telling me to stay put, then his hands slid back down my sides, gripping my waist and tugging me a bit, until I took a step back, arching my back and leaning against the wall. "That's right," he said, nudging his thigh between my legs. "Spread 'em."

I shivered. My eyes were closed tight, even though I couldn't have seen anything but the wall in front of me had I opened them. "Stay," he said, and then his hands were working my belt, my button, and my zipper. My entire body jerked as he pulled my jeans and underwear down, just far enough to expose my ass and set my cock free - my hard on sprung free to attention. Oh my god. I was showing my ass to a whole room full of people. What was wrong with me? Then he crouched behind me, and his bearded mouth pushed between my ass cheeks. I gasped, grunted, and pushed back against his mouth. I could feel him laugh into my pucker, and his tongue made some broad strokes against my hole. Nothing makes me hornier than a mouth - especially a bearded mouth - eating my ass. His rough hands kneaded my ass cheeks, and he tugged at my jeans a bit more, pulling them a bit further down my thighs, and then dove back into my ass with his tongue. He ground his face into my hole, and I groaned and moaned - I was biting my lip to make as little noise as possible, but it was so hard when his tongue was drilling into me. He pulled back, and it was everything in my power not to whimper. He spat. Once, twice, three times. Globs of hot saliva hit my pucker, and he used his rough fingers to rub it around my hole before sliding a finger in. The groan escaped me before I could hold it back, and then he spat again, repeating the process twice more. Then he rose, and I heard the unmistakable sound of his zipper behind me.

Only when he pressed his dick against me did I realized he wasn't wearing a condom, and that the spit was all the lube I was about to receive. One hand on my waist, I felt him adjust his dick and then push into me with a long, slow, thrust. I grunted and shifted in front of him, rising on my toes a bit, and then he was buried inside me. "Fuck that's nice, boy," he said, and his other hand rested on the back of my neck. He fucked me in short, hard thrusts, and it was obvious from the first thrust that this would be fast and rough. I shoved back onto his dick in counterpoint, and his grunts matched my own. God I wanted this! His dick was hot inside me, and the spit wasn't the greatest lube, but the feel of his cock made me crazy, and my semi-prone position against the wall seemed perfectly suited to him. He fucked me for minutes that felt like forever and not nearly long enough, until he tightened his grip on the back of my neck, and shoved in as hard and as deep as he could and blew a hot load of spunk up inside me. The sensation was too much. Before he could pull out, I jerked my dick frantically with one hand, bracing my forearm against the wall, and felt my own cum spray out in a fan across the brick wall. No doubt it wasn't the first load to dry there.

We stood there panting a moment, and then he pulled out. I felt his load hot against my thigh, and heard him zipping up behind me. I shook, then slowly pushed off from the wall. By the time I got up the guts to turn around, he'd left. More than a few eyes of the men were watching me, many of them with their dicks in hand. I felt a flush of pleasure at being the object of their attention, especially given how many of them were bears. I pulled up my pants and underwear, not bothering to try to stop the cum leaking from my ass, and got out of jail.

Edited by Hotload84
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This story reminded me of almost getting auctioned off by the chain of commandd out if Austin , at the cattle drive campout in Cameron or counterfeiting their command cash. And per the agreement, I do carry the one bill to this day, for any of them that even remember its my get out if jail card if you will. And a pleasant memory. Thanks for the story again Barratboy.

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