Charity Hole

The sound of steel sliding on steel woke me to Fredo standing silhouetted by a streetlight outside the van. Without a word, he leaned in and placed a leather collar around my neck with a leash attached. "Lay on your back and spread your legs." I looked down to see him fitting me with a shiny pink chastity device. First my balls went through a ring, then he placed the head of my penis into the cage, closed it so it was pointed down with no room to grow, and then he locked it with the smallest key I'd ever seen. It was only after he was done, I noticed the little opening with vagina lips on the front and the word 'SISSY' emblazoned over it. In case people couldn't tell from the pink cock cage?

He slapped my exposed balls squeezed out from their usually tight position by the contraption. "Me and the boys all chipped in for your uniform. Whenever you're brought here, this is what you'll be wearing. Everyone here tonight paid fifty bucks to the food bank charity to get to use you. You ready?"

"Yes Sir." I couldn't wait to go inside this place I'd heard so many stories about.

He pulled on the leash, and I followed him from the van, across the street, and down an alley. The whole time my mind sat on the knife edge between embarrassment and excitement at the thought of somebody passing by and seeing me in my uniform. We turned into a backyard covered in gravel to serve as a parking lot with a few cars and a couple of motorcycles. The cold early morning air was making me want to pee. The house looked completely dark, until Fredo opened the door, and a shaft of dim pink light came up the walk to greet me.

"Take your boots of and leave them by the door," Fredo instructed as he led me over the threshold.

Inside, they had taken out all the walls and left a few supporting columns. At one time I imagine it had been a very cozy two bed, one bath house. I was intrigued by the shiny chrome drains dotting the polished concrete floors. They had drywalled over all the windows, taken out the ceiling to reveal the rafters, and installed a long trough on one wall that slanted towards a tub. On various screens around the room played videos of my sexual escapades from the day. In addition to the one Alvin recorded and the one from being waxed in the bar, there was now a video from inside the van and various clips taken by the truckers as they used me on the picnic table. Even the Indian guy had taken video of me, and I could hear him calling me a whore in surround sound.

At the far end stood a group of men at a bar in various states of dress. Upon noticing me, they started to meander over to check me out.

The owner of the Padlock, the bar where I was waxed, cupped my caged dick in hand. "Nice, uniform fits perfectly." He reached around with his other hand and felt the plug in my ass. "Perfect. I hear you made four hundred dollars for the food bank."

I looked him in the eyes and said, "Yes Sir."

"In here, your head should be bowed unless somebody tells you otherwise."

I bowed my head. "Yes Sir."

"Do you have any questions?"

"Yes Sir. If I need to pee, where do I go?"

His voice changed from caring old man to sketchy asshole. "Well, you ain't got a dick in here so you can't use the trough. I'm thinking since you got a pussy, you're just gonna have to squat. Here, let me take you over to where we usually let pussies relieve themselves."

He took the leash from Fredo's hand and led me over to the bar area where I quickly counted fifteen guys, not including the bartender and Fredo. Among the men were my waxer from the bar, Ken, Eskander, the hot Persian daddy celebrating his birthday, Leroy who'd lifted me with one arm while waxing one of my armpits, and Mike who'd whored me out at two truck stops. While mike wasn't as pretty as the rest, tall skinny ugly guys usually threw a mean fuck in my experience. I was so turned on to have them see me in my uniform and hopefully take their cocks.

"Hey guys, our friend with the pussy needs to pee."

A tall Asian man with skin smoother than mine moved one of the biggest feet I'd ever seen to reveal another drain in the floor. "Here you go pussy boy. Squat over the drain and don't spill a drop."

They formed a tight circle around me as I squatted in front of them. I performed a delicate balancing act between clenching my ass to keep the plug in and trying to release my bladder at the same time. Try as I might, I just couldn't relieve the stress in my bladder.

"Here, let me help you out." A short, 5'2" if he was lucky, Latino walked over and unzipped his pants unleashing a huge cock. I must have inadvertently given a look of surprise, because he continued in a thick Mexican accent, "I know, I know, I'm half cock. I also need to piss, so open up pussyboy." I opened my mouth and the head of his warm cock weightily sat on my tongue. Soon a stream of piss flowed down my throat.

When he was done, Leroy took his place. He unsnapped the front of his leather pants and pulled out his thick limp cock and massive balls. He was everything I'd ever imagined he'd be in that department. Ken was next with a nice uncut cock surrounded by strawberry blonde pubes. Mike's cock unleashed a stream of piss into me next. Unlike the others, he didn't place it on my tongue with any sort of grace, he just pushed his half hard cock into my mouth until his pubes tickled my nose. Like most men built like him that I'd had he was hung like a generic 9" dildo I had in my nightstand, not too thick and with an aerodynamic head that went down easily. The faint scent of ivory soap fought with a long day, and I wished somebody was working my nipples.

Eskandar approached next. He was still shirtless and fumbled with his belt under his perfect round hairy belly. I felt like a kid on Christmas morning waiting for a specific present and he didn't disappoint. His thick dark uncut cock sat nestled on his large balls contained in a loose hairy sac. The best surprise was the bar going through the head of his cock with a huge ball sitting at either side. He smelled like hot man and sandalwood. After him, another man would take his place until everyone had used me as a urinal. With the last man spurting his last few drops into my mouth, my own stream finally started.

The tan man with the square jaw who had just pissed in me, felt my piss splatter on his boot. "Fucking hell! This bitch can't control her piss. Hand me a rag Bill."

I looked down to see the design of the cage, coupled with Fredo's haste in getting me caged, had allowed for one stream to go down and another to go up, he had been assaulted by the latter.

The bartender threw him a blue shop towel and he threw it onto my face. "Lick it off then shine it up with the cloth." He placed his boot on my knee while I was still pissing.

As I licked the boot and then buffed it to a shine, a few moved behind me. "From back here it looks like a real pussy pissing." A hand felt my crack and patted the plug. "Fuck that ass is smooth. Ken does good work."

I finished pissing and buffing the tan man's boot when he said, "Now clean up all your piss off the floor."

A boot was placed in the small of my back and pushed me onto my hands and knees. "There ya go," a voice said, "and don't miss that spot over there and there." Men pointed to small drops with the toes of their boots.

Another pointed to a spot with the same hand holding a bottle of beer and it spilled. "Get that beer too." For a while they all spilled little drops of their drinks onto the floor and the group followed me around as I crawled on the floor cleaning a never-ending spill, dragging the leash behind me.

They had finally had enough fun with that trick when Leroy dropped a pile of leather in front of me. Crumpled on the ground it appeared to be nothing but a pile of scraps. "Pick that up and I'll show you how to set up your sling. If you prove to be worthwhile, it'll be your job to set up your sling if you get invited back."

He led me over to a particular rafter with two shiny metal hooks in it. It felt so hot being the only naked person in the place and everyone watching me. If I'd had any natural rhythm, I'd probably have been a stripper. He continued, "You'll find two ends with grommets and stretchy rubber on one side. Attach them to those hooks and then attach the other two ends to those springs up there."

With my head bowed, I asked, "How do I get up there to attach everything?"

"Pick up the first end and I'll show you." When I found the first strap to attach, I felt Leroy's big arm sweep between my legs and my taint was suddenly sitting in the crook of his elbow as he lifted me to the ceiling. The plug in my ass sat squarely on his vibrating bicep while my caged cock pressed into his forearm. I was in heaven.

When we were done, a woven square of wide leather straps hung loosely in the air and my caged cock had become a fountain of precum. Attached to the straps leading to the ceiling were smaller straps with buckles on them. A tall skinny light skinned African American man with a stubbly beard and close-cropped hair approached me. "Let's see if you fit." He picked me up under each thigh, making my cage press into his stomach. He smiled as he looked down at the trail of precum I had deposited on him. "This bitch's clit is leaking." The men laughed and started to head over. He placed me into the sling and buckled my ankles in while Leroy secured my wrists.

My racing heart made the sling sway slightly as I lay there naked, defenseless, and splayed open. An older white man with sagging skin and a bald head cleared his throat before speaking in a gruff voice. "Let me get down there before you pull the plug." He squatted with his face almost in my ass as the tall Asian man slowly worked the plug out. The older man spread my ass and tongued my hole like a dog eating peanut butter.

He came up wiping cum off his upper lip. "Damn! That boy's ready. I don't think we got enough dick in the room for him."

Fredo smiled at me. "Yeah, she's good little sissy, but she's a whore."

A young Latino man in his early twenties sat a leather top hat on my stomach. "We all know the rules, pick your place in line out of the hat for your first load. If you feel like a second go, then it's catch as catch can."

They all drew a number and the short Latino man who started me off as a urinal held up his tile, "Number one!"

The old white guy held up his tile, "Fuck, I got number two. After Jose's been in him, he'll be all stretched out."

Fredo piped up, "We still got those e-stim clamps here?"

"Yeah, they're behind the bar," Bill, the bartender replied.

"Go get em, let's light this bitch up. Her pussy's wired to these nips." He took one and twisted it hard, making my body clench.

"Hey, lookie there's she winked at me finally," the old man said.

Jose grabbed a footstool to be at the right height for my hole. He slipped the tip in and wiggled it around in my wet gaping hole. "Fuck yeah! This bitch is the definition of pussyboy. This shit is wet. Should I go all in guys?" It took a mere moment of cheering for Jose to thrust the entirety of his cock deep within me. Even after all the thick cock I had taken in the past twelve hours, Jose's dick felt like it was pinning the walls of my ass against the bones in my hips. I gasped at first while he grabbed my hips to push just a few more millimeters into me. He swiveled his hips against me and rubbed his hairy balls against me. It was that move that switched my gasp to a moan and Jose saw my eyes roll back into my head. "Fuck yeah, this bitch can roll with it." Slowly he drew his cock out of me and then slammed it back in. Guys took pics with their phones of his massive cock as it stretched and pulled on my hole.

Leroy stood by and videoed my hole being use. "Look, Jose's making that ass into real pussy lips." Jose and a few other laughed.

Jose closed his eyes and bit his lower lip as his pace quickened to a hammering pace creating a steady thump against my body. "I can't believe how much my dick is sliding around in this bitch."

He looked at me and asked, "How many loads you take tonight?"

Fredo laughed, "This whore started in the afternoon." He turned and slapped my face. "Didn't you whore?"

"Yes Sir," I replied shyly.

An older bear with thick salt and pepper hair covering his body added, "Why you shy now with your legs spread and a giant dick in you? Be proud. Have you been whoring around since this afternoon?"

"Yes Sir."

"I can't hear you over Jose slapping against you. Have you been a big ol' sloppy whore all day?"

"Yes Sir!"

They all let out a chorus of "Yeah," while Jose's pace picked up even more.

He was pounding hard inside me and repeatedly whispering 'fuck' to the insides of his eyelids. Soon he tensed and every vein in his small muscly body popped out, he bared his clenched teeth and released into me. His warmth flooded my cavernous insides. He stayed in me for a minute and then pulled out his softening cock. Everything around his crotch was white with foamy cum he'd churned up from within me. "Damn, talk about a cumdumpster. Somebody throw me a towel. Fuck."

Another blue shop towel flew through the air in his direction, and he wiped all around his cock and even up into his inner thighs.

The old man looked at my gaping crater of a hole. "New rule, Jose goes last."

Fredo appeared with nipple clamps with wire dangling from them, "I got you pops. We'll get that ass around your cock." He plugged the wires into a box and pressed a button. An intense electrical pulse zapped my nipples. I screamed out and my body convulsed.

"There she goes winking at me again," the old man said to a response of laughter.

Bill appeared from the side with another box like Fredo held, but the wires didn't end in clamps, but instead a small elastic band with something attached to it. "I haven't tried this yet. Let's place this on pussyboy's balls and see if we can't get you a more virgin-like hole daddy." He placed the band around my nuts, and I could feel a cold metal spot press into me. He pressed the button on his box and the pulse was even more intense. While men have often played with my nipples, few have ever done any CBT with me, so they were extra sensitive to the treatment.

"Heck ya, that'll work." The old man slid his cock in me as Fredo and Bill randomly pressed their buttons making my aching hole clench around the dad's cock. Slowly a rhythm evolved between the three of them. "This is awesome. That pussy's just pulsing away on my cock. This is better than that blowjob machine I got." His pace quickened gradually, as did the shocks to my balls and nipples until the man let out a groan and shuddered a couple of times within me.

Mike stepped up next and slid inside of me with little fanfare. He was quiet and mesmerized by his cock sliding in and out of me.

"You want that hole to dance," the bartender asked.

"Yeah, shock him as I come out so he can milk me."

They did as he instructed, and it wasn't long until quiet Mike started moaning louder and louder. Eventually he ordered the e-stim left in the 'on' position while he finished. The feeling of electricity running through me was extreme and my body tensed into an arch while Mike grabbed my hips down onto his cock. I could feel my hole gripping the entire length of his cock moving within. His moaning stopped, his mouth opened to a silent scream, and his body shook inside me. He took a few more strokes in me before signaling the e-stim to be turned off. My hole let go of his dick and he slipped out of me. "Fuck yeah," Mike said in a tone reminiscent of a WWE wrestler.

Leroy stepped up next. While I didn't get to see his cock at full mast, I could certainly feel it. It was thick with a pointy head, a big vein on the bottom and big hard veins all around the shaft. It curved up inside of me and I could see the skin above my crotch pulse with each of his thrusts.

Fredo thought he'd be helpful and zapped my tits, causing my hole to act like a braking system on Leroy's cock. "Dude, don't do that again. I'm pressed tight against all 360 degrees of this hole."

He pulled out of me, deposited a gob of spit on his cock, and slid back in, resuming his rhythm. He looked me in the eyes and asked, "You want this cum?"

"Yes Sir."

"Start trying to milk me. If you can clench with the e-stim, you should be able to milk my cock."

While I couldn't tell if I was actually able to clench, the smile on his face said I was successful. "Yeah, that's a good boy. Keep that up and earn this cum." His pace quickened and he slammed into me even harder than Jose had earlier. The hardware holding the sling in place rattled as sweat rolled down his face and dripped onto my skin. He grimaced, but never slowed his paced as I felt a new warmth deep within me. When he'd shot his load, he fucked me slowly for a couple of minutes to drain the last drops into me. He leaned over, kissed me, and whispered in my ear, "Gonna have to have you over for a pool party in the summer."

"Yes Sir," I said with a smile.

Eskandar's fuzzy body rubbed against my inner thighs. He slipped a couple of fingers in me, drew out some of Leroy's cum. "Open up, I know you want to taste it." I opened my mouth, and he inserted his fingers, letting them linger for a moment so I could suck all the salty semen off. As he leaned into me, I felt his hot thick cock rubbing in my crack and his soft hanging balls against my lower back. He didn't have the longest cock of the night, but he was certainly top three when it came to girth.

He lined up his cock and pushed it in all at once. It felt amazing. It filled me perfectly and the piercing instantly connected with my prostate. Every thrust inside me I could feel my balls getting tighter and tighter until my dick exploded inside the cage. Cum came out of both the piss hole and the little vagina and ran all over my balls, down my crotch, and added to the cum Eskandar was using for lube. My orgasm was so intense I soon felt him release his load.

After Eskandar, Leroy, and Jose, the rest of the men couldn't help but feel average. The remaining men opted for using the e-stim to control my hole. A few had nice curves and PA's that made things interesting, but with the e-stim going, I couldn't help but really connect with my hole and just use them as human dildoes for my own pleasure.

One after the other they took their turns inside me as Fredo and Bill made me convulse uncontrollably. Some of the guys left after their first turn, but others went a second round. Eventually just Fredo, Jose, and I were left.

"You want to try that hole with the e-stim Jose?"

"Can you run both units alone?"

"We'll have the sissy whore run one."

"Fuck yeah!" He said as he brought over his stepstool.

He handed me the controller attached to my balls. "Get it up to halfway every time or I turn them both on full. Got it?"

"Yes Sir,"

Jose slid his amazing cock in me. Between his enormity thrusting in me and the pulsing of the e-stim I came again inside the cage. It was such an odd yet satisfying feeling to cum without an erection, just deriving pleasure from being fucked. I really was becoming a sissy like it said on the cage.

"Damn bitch, you've cum twice from that pussy being used," Jose said as he picked up his pace.

"Yeah, he don't need his dick in here."

Jose was getting closer with every slap of his body against me and soon he seized up and unloaded his second load of the night into me.

Fredo pulled the plug out of his pocket, "Here, put this in him so he doesn't make a mess in his car."

The plug slid in with ease after Jose's assault on my hole and slowly my ass closed around it. Fredo lifted me out of the sling and handed me a mop and a bucket on wheels. "Clean up your mess before you leave. I'll be nice and take down the sling for you."

A mix of gelatinous pools of cum and dried boot prints of the men who'd fucked me covered the floor where I'd been fucked for hours. It took a while to mop up all the boot prints and I ended up mopping most of the building before I was satisfied it was clean enough they'd ask me back.

Jose had finished cleaning up behind the bar and Fredo had put away the sling just as I was done mopping. Fredo came over, pulled out the tiny key and freed my cock and balls from the cage. He looked inside and saw wet cum still inside. "Lick this out." I did as instructed and then he wiped the inside out with one of the blue shop towels the club used. He then took the leather collar off me. While I'd only had the collar and the cage on for a few hours, it felt like something was wrong when they were taken off. Damn, Fredo had turned me into a hairless sissy.

"May I go pee Sir?" I asked with a downcast gaze.

"I don't have time to wait for you to piss. Do it in the alley on the way back to your car."

"Yes Sir. Do you have anything I can wear?"

"Does this look like a fucking Macy's? Jose, get me another towel."

Jose brought over a towel and Fredo handed me the one in his hand. "Tie these together and make a little skirt for yourself. bitch."

"Yes Sir." I took the towels and started tying two of the corners together.

"Jose and I don't have time for you to make your dress. Do it outside."

Fredo opened the door for Jose and kicked my boots out onto the gravel after him. One of them went under the front of Fredo's car. "Guess you'll just have to wait bitch."

It felt like forever waiting for him to get in his car and leave. When he finally did, I realized I was naked, I still needed to piss, and the sunrise was starting to make my pale body very visible.  I tied two corners of the towels together, put them around my waist and tied the other two corners making a sort-of loincloth. I put on my boots and walked behind a giant trash bin to piss and then down the alley to where it met the street. I looked both ways and was relieved not to see any cars. The cold morning air felt amazing against my recently caged cock.

I crossed the street to the parking lot of Padlock and walked over to my car, unlocking with the keypad on the door. I had been so intent on getting in my car, I hadn't seen the two cop cars sitting side by side as the officers talked to each other. A quick sound of the siren froze me with my car door open. I heard one vehicle drive up behind me and park, while somebody got out of the other vehicle and slammed their door shut. One whispered to the other one, "body cam," as their boots got closer.

"Well, well, well, what do we got here?"

I turned around to see two male officers, one a bit closer to me than the other. They were practically carbon copies of one another, fit, with military haircuts and an undeserved air of authority. The one close to me had a name tag that read 'Williams, D.' while the one further away read 'Daniels, W.' and for a moment I wondered if they had the same first and last names, just reversed and how funny that would be.

"Looks like Fredo came through after all," Daniels said with a grin on his face.

Williams slid his hand up my thigh and grabbed my ass. "Fuck, that's a big ass for such a skinny guy."

"All these white guys doing squats to get curvy like black women," Daniels added.

"Open that door all the way, bend over, and put your hands against the car." Williams turned to Daniels, "Put your cruiser across here so we got some privacy."

I complied with Williams' request as I heard Daniels moving the cruiser behind my car, creating a little square between the three vehicles and my open door.

William lifted the back of my makeshift loincloth and ran his nightstick up my inner thigh and up my ass. He felt the 'clunk' of the stick hitting the plug in my ass. "What's this?"

He pulled my ass apart and I saw him bend over in the reflection of my car. His fingers latched onto the plug and yanked it out creating a vacuum that suction hours of deposits out of me. Cum fell out of my ass with a splat onto the blacktop.

Daniels laughed, "I've heard of being rode hard and being put away wet, but this is the first time I've actually seen it."

"Nice that he's preloaded for us. Saves time. I got to get home, and you got to start your shift." Williams yanked the shop towels off my body and handed one to Daniels. "Use this so you don't get this whore all over you. Something tells me she's gonna be a gusher."

Williams took off his belt and placed it on my front seat, then I heard his zipper, and then I felt his cock slipping into me. In contrast to the chilly morning air, his dick felt like a hot sword pressing into me. It was far from the biggest dick I'd had in me in the last twenty-four hours, but it wasn't the smallest either. One of those that makes its owner feel like they are just above average enough to say they have a big dick. He wasted no time getting up to a jackhammer pace while Daniels served as a lookout. In just a few minutes he added his load to the mix.

"Clean off my cock."

I squatted and licked the mix of DNA off him. He handed me the towel, "Get it dried off." I followed his orders. Afterwards he reassembled his pants and his belt and motioned to Daniels it was his turn. "Come and get it."

Daniels dropped his belt in my front seat, unzipped his pants, and pushed his much bigger cock into me. It was ramrod straight with a big mushroom head. With every thrust in, it would collect cum from my inner walls and pull it out to run down my legs. With me bent over, he hit my prostate every time, making my dick rise to attention. Like his partner before him his pace was frenetic, and his staying power was minimal. He grabbed my sore nipples, causing me to bear down on his cock, and the sensation made him blow his load. And what a load! I had always dreamed of being with a guy who came ribbons of cum for six or seven strokes and he made it come true. I might have lost a few loads when Williams pulled out the plug, but Daniels replaced them and then some.

Soon his dick was out of me, and I watched as he wiped it down with the other half of my loincloth.

He redressed and walked over to Williams, "That was just what I needed to start my day."

Williams looked at me standing naked next to the car, "Better get covered, be shame if you had to go on the national sex offender's registry for being naked in public."

"Yes Sir."

I grabbed the plug off the top of my car, got in and shut the door. I stared straight ahead with my heart racing as I listened to the officers leave the parking lot. Soon, the fear subsided, and I looked in my center armrest for my phone that had just buzzed. Fredo had sent a video clip with the message, "Can't wait to add this to your playlist at the bar." I pressed play to see a recording of the two cops fucking me. The security camera on the corner of the building had been high enough to capture everything despite the position of the cars.

In the silence of my car, I became aware of my still erect cock and fluid moving in my ass. I reached between my legs and pressed the plug back into position. I couldn't wait to go home and use some of this cum to jack off with and some of it to ease my black horse cock dildo into me. I deserved a reward for all the work I'd done tonight for charity.