By JR

Florida has a funny way of taking things the rest of world enjoys and making them trashier.  Outside of the state’s biggest cities and most expensive zip codes, this state has all the refinement of a Jerry Springer episode, and the gay culture is no exception.  One area where the trashy factor really shines through is in the run down mid-century motels turned into gay resorts.  They litter the state and all have a similar feel: sparsely furnished rooms, poolside bars, and lush landscaping to keep activities somewhat private.  One of these resorts on the west coast is pretty big and has some well attended themed weekends, so naturally I checked in for their annual leather weekend.  I left my sometimes uptight professional demeanor at home, submitted to the fact that it would not be a weekend at the Four Seasons, and packed for what I hoped would be Florida’s version of IML.

I set my work aside early on Friday afternoon and headed across the state to the resort.  It was exactly what I had expected from the online photos, perhaps even a bit cleaner and more updated.  There were two long two-story buildings with second floor open walkways flanking the pool.  The former hotel lobby and restaurant had been converted to bars, one with a little dance floor.  The décor was part kitschy mid-century modern, part whatever the owners could find on the cheap.  The place reeked of bleach, which I took as a good sign.

I lugged my minimal bag of clothes and a heavy bag of gear up to my second floor room, from which I could observe the activities around the pool.  The owners gave the rooms far less attention than the bars in their renovation, but at least the sheets looked crisp and clean.  I unpacked, hanging up my leather jeans and harness in the closet and setting some toys and other gear on the dresser.  I showered and put on a pair of camo shorts over a jockstrap and some flip-flops to head downstairs.

I didn’t have any agenda or specific friends to meet.  A few acquaintances would be there, a couple of guys I messaged with on Recon, but otherwise I had the weekend on my own to explore.  Being Florida, the crowd can be older, which makes a muscular bondage sub in his 30s like me a hot commodity.  I wanted to spend some time checking out the crowd and the little bar venues off the main pool area before seeking any action.  The weather was hot and the pool looked inviting, but there were not many guests there yet.  There were at least three bars around the pool, each manned by a hunk in a harness and shorts.  It would be much busier the next day, with every poolside chair claimed and vendors set up in tents around the perimeter.

I wasted no time getting a beer from the hottest of the bartenders and chatted him up about the resort and what he expected for the weekend.  He was pretty certain I would have no problem getting into some trouble, and if I was still up when his shift ended, be would make sure of it.  I promised him that if I wasn’t tied up somewhere, I’d find him.  But no need to spend time flirting with the bartender when there had to be plenty of more available guests to meet.  I grabbed a second beer and moved on, walked to the back of the property to see the sun setting over a little marina.  As the sun set the music from the poolside DJ got louder, a dark beat to get my pulse going in anticipation of after-dark activities.

I walked back towards the pool, past the big tiki bar.  A few older bears called after me, and I went over to the bar to say hi.  They seemed to think I looked innocent, like maybe I didn’t know it was a leather weekend.  I used to play innocent – it turns some guys on – but I’ve matured and go after what I want now.  I called one of the guys “sir”, and just the sound of that made his dick twitch visibly in his shorts.  He grabbed the back of my neck with his meaty bear arm and pulled me close, promising that if I wanted a sir he would make me his boy.  I just smiled, felt my own dick stiffening in my tight jock, but pulled back and moved on.

I headed towards the inside bar that I’d passed when I checked in.  There was a sign posted: gear only.  That was my cue to get changed, so I headed back upstairs.  I shut the door to my room and took in the air conditioning.  After an hour in the humidity I was already slicked with sweat.  Another shower and some preparations were in order, then I would head back out.  I selected a black leather chest harness,   then a put on a thick metal cock ring and a rubber ball stretcher, and stuffed myself into a pair of dark gray skin tight rubber jeans.  Black boots completed the look, a simple outfit for the first night of a long weekend.

As I was dressing I noticed someone outside the window, peering in between the curtains.  I didn’t mind giving some guy a show, and never bothered to shut them.  When he saw that I noticed him, he didn’t move.  He just stood there staring intensely. I smiled nervously, finished combing my hair, and headed for the door.  As I opened it and turned to look at this guy, he turned to look at me and continued staring.  He was intimidating even in his silence, a couple of inches taller than me and every bit as solid.  He had on black jeans and a tank with a thick black leather band around his left bicep.  Clean cut with a rough edge, I liked that.  And direct.  “Thanks for the show.”

“You’re welcome.”  And after a bit of a pause and checking him out head to toe, I added “Sir”.  My response brought on a big smile, and we got to chatting.  We covered the basics.  Where are you from?  Both from different parts of Florida.  Who are you here with this weekend?  Both on our own.  Been here before?  No.  How long are you staying?  We both planned to leave Monday.  What do you do to keep in shape?  I’m a runner, with alternating days in the gym.  He was mostly a gym rat and played in a gay volleyball league.  And then the inevitable, what are you into?  Him:  “Just your everyday bondage top who likes to keep his slave locked up, stuffed, and ready to serve.  To get punished and humiliated and beg for more, even when he doesn’t think he can take any more.”  Me: “Challenge accepted.”

He warned me against diving into his control too easily because once I submitted I was his until Monday, and he suggested we spend a little more time chatting down at one of the bars.  I followed him along the balcony and down the stair, but when we got to the bottom he turned and walked towards the parking lot side of the building.  “On second thought, let’s stop by my room and get you dressed a little better.”  I thought I looked hot as I was, but was also eager to see what gear this guy brought.  I followed obediently.  His room was at the end of the hotel, the last room in the building facing out to the parking lot instead of the pool.  I followed him into a dark room, with only the dim light of the parking lot peeking through a small gap in the closed curtains.  He turned on a lamp to illuminate a hotel room turned dungeon, with cases of gear everywhere.  It occurred to me that he had to be a vendor.  They often set up tents by the pool for events like this, making a small fortune off with high prices that customers don’t seem to mind paying once they are drunk and horny. I was a kid in a candy store.  I moved forward to look at his inventory, but was sharply rebuked.  “Stand at attention boy.  Turn and face the door.”  I did as ordered, as he rummaged behind me.  “Hands behind your back!”

I quickly clasped my hands behind my back, and stood up straight with my chest out pressing against the harness straps.  He came up behind me and hugged me from behind, grabbing and massaging my chest and kissing my neck.  I felt his erect dick through his jeans and instinctively pushed my ass into his crotch, proving to him what a horny and eager slave I would be.  He ground against me and told me how hard I was going to work for his cock.  Fucking me would be a reward only after hours of bondage, torture, and humiliation.  He stepped away and came back with some long leather mitts.  He stood in front of me, told me to make a fist, and slipped the mitts onto my arms nearly up to my elbows, taking his time to buckle three straps on each and then fold the ends over and lock them to the straps, forcing my hands to stay clenched.  He then pulled my wrists behind my back and told me to stay still as he grabbed something to restrain them.  He showed me the rigid metal cuffs before installing them on my wrists, two 3” wide bars of steel clamped over my wrists like guillotines keeping them about a foot apart and unable to bend.

I stood there for a couple of minutes again facing the door, my dick pulsing in anticipation of what would come next and leaking into my rubber pants.  Twice he came over to me to try different collars on, then I heard more rummaging.  Curiosity then got the better of me, and I made the mistake of turning my head around to see what he was up to.  He noticed, and immediately decided that my curiosity to see should be countered with the most intense hood I have experienced.  It was massively thick leather with laces up the back and then four heavy straps that each buckled and locked.  The eyes had pinholes so I could still barely see and the mouth was open, but there were extra buckles for attaching a blindfold and gag, which I was sure he had nearby and would need little protest from me to install.  He went over all of the laces and buckles twice, then stepped back to enjoy his work.  He could see me smiling through the mouth hole, enjoying this tight and immersive hood, taking in its strong leather smell.  I shook my head just to hear and feel the padlocks rattle.

“How do you feel about wearing that over to the bar?” he asked me.

“I’m ok with that sir, just don’t lose me.  It’s hard to see.”

“It was a rhetorical question, boy.  Let’s go.”

I followed him out of the room and down the covered walkway, past the pool and into the main bar area.  It was getting busy.  The smells of leather and sweat were just starting to penetrate the air.  I stayed by his side, drank a beer when he lifted it to my lips, and gyrated awkwardly on the dance floor with my wrists still rigid behind my back.  He may as well have strapped the blindfold on, as I could barely see anything in the dark club.  I was completely dependent upon him, and he knew it.  Eventually I had to pee, and asked him for help.  There was a line for the restroom so he took me back to his room.  He undid my jeans and peeled them down, then stood behind me and held my dick so I could pee.  I couldn’t pee.  The ball stretcher and cock ring combined with my general situation left me too aroused, and I stood there for several minutes trying to pee as he grew impatient.  He then took off the cock ring and ball stretcher – a huge relief to my aching balls – and I was finally able to pee.  I then moved aside as he peed, which gave me a glimpse of his dick for the first time.  I wanted to get down on my knees and worship it right then, but was getting to know this guy enough to know not to take initiative.  When finished he shuffled me out to the bed, pants still down around my thighs, and bent me over the bed.

In a matter of fact tone, he stated “Time to stuff your holes,” and then produced an imposing silicone butt plug.  I took a deep breath, and could not stop myself from protesting, “Can you please start with something smaller sir?”  The answer was a simple no, and he went to work lubing up my hole.  I gasped when he thrust his fingers in, then relaxed a bit and enjoyed his touch.  But when he removed his fingers and started with the tip of the plug I resisted, begged him not to put it in me yet.  He got up, I hoped for something smaller, but instead he returned with a thick penis gag, roughly shoved it in my mouth and buckled it to the hood.  Then I saw darkness as he strapped on the blindfold.  Then he returned to my ass and worked the plug in as I bit down hard on the gag and resolved to just take it.

Eventually I took in this entire plug and enjoyed the full feeling.  He stood me up and told me to stand still.  “Now that your dick is finally soft, I can lock that up to.  And just so you know, boy, none of this is coming off tonight.”  I then felt a cold tube encasing my dick, my balls pulled through a ring, and the sound of another padlock clicking shut.  My dick started to test the cage, getting hard within its confines.  He noticed my arousal, and grabbed my balls hard, pulling me across the room by them.  “You’re liking this a little too much, boy.”  He then swatted at my balls hard with some sort of paddle sending pain right to my stomach, still keeping them in his tight grip.  I next felt more pressure on my balls as he applied a ball stretcher – not sure if was mine or one from his collection – before shoving my junk downward and pulling up my skin tight pants over my locked up bulge.  He quickly switched to my nipples, adding clamps on each connected by a chain.  This he used to pull me behind him, out the door, and back to the bar.

I stumbled along in complete darkness, ass filled and prostate stimulated with every step.  My balls were already aching and they’d only been locked up a few minutes.  He went quickly, forcing me to trip and torture my own nipples as he kept an unrelenting grip on the chain between them.  All I could do was follow him and try not to fall.  We stood around the bar for awhile.  I could hear him chatting with others, but he music coupled with the hood made voices impossible to hear.  We left and spent some time sitting poolside, which I could tell from the sound of occasional splashing.

We then went into another of the resort’s bars.  This one felt warmer and the music was not nearly as loud.  He pulled my arms up behind me and I felt the rigid cuffs secured to something at about shoulder height, putting stress on my shoulders.  And he left me.  Within minutes my shoulders were on fire and I was struggling against the cuffs, trying desperately to lower my arms even an inch.  There was no movement, and I just rocked back and forth to maintain circulation, wondering how long he would leave me like this.  I was drooling through the gag and at some point tears formed in my eyes.  I was truly fucked, locked up in a bar by a guy I hardly knew.  But I was still hard inside the chastity, my dick flexing against the tube and pushing against the crotch of my rubber jeans.

It must have been an hour before he came back.  He released the gag, gave me some water and kissed me deeply.  He asked how I was.  I was sobbing, “I need out sir.  Please!  My arms are on fire.”

“I don’t like wimps,” was his only response.  Suddenly I feared disappointing him, and was mad at myself for being weak.  I tried to apologize, but as I opened my mouth he shoved the gag back in.

“I know you’re sorry,” he said as if reading my mind.  “Just a little longer.”  He lowered my arms to about the middle of my back and left again.  This position was more bearable, but not easy.  He came back in less than an hour this time and when he released the gag and asked again how I was, I simply said “Thank you for testing me, sir.”  He liked that response far better, enough to release my arms from the wall completely.  He left the gag out, pulled me out of this bar and back to his room.  Once inside he told me, “You’re going to suck my dick and then suck my friend’s dick, and then we’re going to talk about the rest of the night and weekend.”

I got down on my knees immediately and took his dick in my mouth.  I greedily sucked his salty dick, thrusting down to the base over and over.  I wanted desperately to make him happy and even more so to taste his cum.  He pulled out and I felt someone else grab my collar, taking his place.  Again I sucked obediently as this guy raped my throat, jamming his dick inside and holding it there as I sucked like a trained whore.  This went on, back and forth, until they each exploded in my mouth.

I heard the door open and close, telling me I was alone with him again.  He asked how I was persevering, if I was having a good time.  I told him I was sore but ok, definitely enjoying.  Did I want to stay or get free?  It was a fun crowd and he didn’t want to deprive me of playing with other guys, but if I did stay he would make it worth my while.  I was horny and wanting more, and not worried about what I might be missing outside.  “Alright, here’s the deal.  I’m going to get you out of some of that gear so you can sleep, and tomorrow I’m going to put you to work at my booth by the pool.”  He started to undo the rigid cuffs, finally giving my shoulders a break.  “When I go to these events, I like to find a willing boy that can make my gear look good, or for customers to use to test anything I sell.  Are you game for that?”  That sounded like a lot of fun to me.

“Yes sir.”

“And as a reward, I will keep you locked up the rest of the time just like you seem to enjoy.”

“Thank you sir.”

He pushed me onto the bed onto my back, removed my boots and then my pants.  He commented on how sore my balls looked as he removed the stretcher that had been on for several hours, but he left the chastity device in place.  He removed the nipple clamps and massaged my aching raw nipples, making me scream into the gag.  He flipped me over and pulled my mitted hands over my head, cuffing them and then clipping the cuffs to the back of the hood’s collar.  He then told me he was going to keep me stuffed, but with something more comfortable for sleeping.  He removed the massive plug from my ass and decided he would give me a good fucking before inserting another one for the night.

I was bent over the bed, moaning and enjoying his dick, begging him to fuck me harder.  He obliged for a moment and then stopped, pulled out, and told me I needed to learn some obedience before I earned his load.  I next felt a gag entering my mouth, this one as big as the one before but more pliant and with a breathing tube.  I realized he chose this one because it would let me breathe overnight.  He then told me that a good fifty strokes with his paddle would teach me to be quiet, and started working on my ass hard.  It felt like a thick leather paddle, and it came down squarely on my ass over and over.  I stayed as still as possible for the first twenty swats, tried to keep my ass up in the air and prove I could take his punishment.  But eventually I reflexively pulled back, and he was not pleased.  He threatened to bind me to a chaise by the pool and let anyone take turns using and punishing me through the night.  I screamed into my gag in protest.  He could tell that the threat genuinely scared me.  And I stuck out my sore ass for him to paddle some more, mumbling “thank you sir” into the gag after each swat until he was done.

He made good on his promise of stuffing my ass, this time with a slightly smaller plug than before.  He guided me to the bathroom to pee, then back to the bed area.  He pushed me onto the bed, laid down next to me, and told me to get some rest.  I laid there on my stomach, mitted hands locked to the back of my neck, gagged, hooded, harnessed, ass stuffed, and dick locked up.  Too horny to sleep and trying to move as little as possible so the noise of the metal handcuffs would not disturb him.  I got into a steady breathing rhythm through the tube of the gag and dozed off intermittently.  I had horny dreams and woke up numerous times with my dick trying to escape the chastity device, followed by a brief panic as I remembered where I was and why I could not see or move my hands.

I woke up Saturday morning to the sounds of Sir moving his inventory out of the room, presumably to set up his tent for the day.  He let me rest awhile longer, and then unlocked the cuffs and mitts.  He placed a key in my hand and told me to figure out the rest and clean up.  I removed the gag, blindfold, and four locks on the hood, unlaced the hood, and took in a deep breath of fresh air as my eyes adjusted to the sunlight streaming in the window.  There was no key for the chastity device.  As I was gathering my pants and harness, he returned to the room.  He told me to take my time to go shower in my room and get some breakfast, then meet him by the pool.  He then handed me a small bag and told me my uniform was inside.

I pulled my rubber jeans back on and headed back to my room to shower, stretch out my sore muscles, and recuperate.  While showering I had a chance to check out the chastity cage, which looked like something I had seen on the Steelworks website, gleaming stainless steel and very secure with a completely solid tube except for one hole to pee and thick ring around the base of my shaft. I emptied the bag and found only tiny yellow swim briefs inside, shiny like water polo players wear.  I pulled these on and the impending humiliation from having my locked dick clearly on display as it stretched the front of the briefs forward set in.  But I had no choice.  I headed down to the pool to see Sir, trying to avoid eye contact with the men staring at me and my pitifully locked up junk every step of the way.

I approached his poolside booth, a 10’ x 10’ tent with gear on every surface and a table in the middle with more gear.  His booth had a sign: Tom’s Leather Shop.  Then I noticed a second booth adjacent that was rather empty, except for a black wood platform and a set of stocks.  “Here’s the deal, boy.  You are going to stand on that platform and whenever I or a customer needs to try out a product, I will let you know.  Understand?”

“Yes, sir.”

I stood on the box obediently, waiting for further direction as I gazed at the pool and the growing crowd.  It was about 10 AM.  Hotel guests made their way to the pool, the DJ started up with subdued tracks, and the sun started to bake Florida in its typical June way.  It did not take long before a few guys made it to Tom’s Leather Shop.  And once they did, Sir was eager to let them know that I was there to assist in any way necessary.  In fact, he insisted, when one of the guys picked up an extreme looking pair of hinged cuffs.  He summoned me over, instructed me to turn around, pulled my wrists behind my back and locked on the cuffs.  “Struggle, boy!  Show my friend how secure these are!”  I struggled, uselessly, as the wide and heavy cuffs did their job.  The customer was impressed, but did not make a purchase.  “I’ll just leave them on him in case you want to see their long term effects.”

I returned to the platform, hands cuffed.  A few minutes later some other guys gathered at the table.  They wanted to stock up on lube and asked Tom’s advice.  He again summoned me over, turned me around, and bent me over his table.  He pulled down my swimsuit, grabbed a massive stainless steel plug, and spoke about the virtues of one of his lubes while liberally applying it to the toy and my hole.  He teased my ass with the tip of the plug for a moment, then shoved it in with one swift motion, making me gasp and squirm.  He pulled my shorts back up and sent me back to the platform.  They bought the lube.

As soon as the customers disappeared sir came over to me and told me that I nearly cost him a sale by resisting and making noise, and I was going to pay for that mistake.  The next half hour was slower with few customers.  I stood on the platform, sweating.  Sir decided it was time for a flogging demonstration, and placed me in the stocks.  He fit a thick bit gag in my mouth and a blindfold over my eyes before warming up my back with a flogger.  I heard the DJ announce the demonstration, inviting guests to participate.  The “demonstration” started with Sir warming up my back and legs, before he turned over the flogger to a series of other guys, none of whom were gentle.  He then switched to a bull whip, striking my thighs over and over as I bit down hard and screamed into the gag.  He stopped periodically and asked if I wanted more, and I nodded each time because though I did not think I could stand any more pain, I did want to make him happy.  The demonstration lasted about a half hour, before Sir released me and told me to cool off in the pool.  The lukewarm water soothed my back slightly.  I had never gone swimming with a butt plug in before.  The wet swimsuit clung to the chastity device, making it even more obvious, but I no longer cared.  I felt lucky to have sir’s attention and to be the subject of punishments from the men around me.  My dick was throbbing inside its metal tube, anticipating what might come next.  One of the hot harness-clad bartenders came over to deliver a beer, and I gulped it down greedily.  Maybe the alcohol would numb the stinging marks across my back and thighs.

After cooling off in the pool for a while, I headed back to Sir’s booth.  “I thought about your punishment, boy, and here’s what we’re going to do.”  Fuck, I thought the flogging was my punishment.  “Go to your room, take out that plug, and get dressed for a run.”

I went upstairs to my room and slowly removed the plug, which was no longer lubricated after being in the pool.  I put on a jockstrap to keep the chastity device from bouncing around, some short nylon track shorts, a matching tank top, and my running sneakers.  I wondered why Sir thought running would be a punishment for me, as I am an avid runner.  It was a bit hot, but nothing I had not experienced before.  I grabbed my phone and headphones, then headed back to the pool.

“Damn you look hot, boy.  But before I send you out on a five mile run, let’s lose that shirt and find some better shorts.  I want everyone one you pass to see what a fucking disobedient slut you are.”   Now I understood where he was going with this punishment.  He made me strip down to my jockstrap right there in his booth and then handed me some tiny super gay white booty shorts, shorts that look hot on Andrew Christian models but I would never actually wear for a run anywhere outside of West Hollywood.  “Now you look ready for a run, boy.  Head any direction you choose, but don’t come back until your running app hits five miles.”

“Yes sir.”  This was going to be humiliating.  The little resort was an island of gay in a bit of a rough neighborhood, mixed with rundown shopping centers, highway overpasses, and some industrial buildings.  I imagined I would hear the word “faggot” yelled at me on every block, or worse.  I walked towards the parking lot and stopped to stretch a bit before taking off. The only thing worse than running through this area dressed like this would be getting a cramp and having to stop. Sir saw me stretching and walked over to me. “Are you delaying, boy?”

“No sir, just stretching before I run like I always do.”

“Good idea boy, you should also probably hydrate.” With that statement he grabbed me by my neck and pushed me down to grass. “Stay.” He pulled down his zipper and brought out his dick to pee on me, while motioning behind him for someone else to join. Before I knew it, there were four other guys standing around me pissing all over me, Sir demanding that I keep my mouth open. I was soaked and reeked of beer-laden piss. The tiny white shorts were already clinging to my jockstrap, making the chastity device obvious. Now I was sent off to run. I took off through this unfamiliar neighborhood, guessing which direction would be least populated. Soon my sweat mixed with the piss, making me a slimy mess from head to toe, socks getting wet and squishy as I hit the second mile. Sweat dripped down my face, mixed with piss, and left a salty taste on my lips. I looked down at my soaked white shorts, clinging to my black jockstrap and chastity device below. Why was I doing this? I caught my reflection in a shop window, then saw the puzzled looks of people inside, and picked up my pace.

The run was uneventful, other than a few car horns and whistles in my direction. I had my headphones on, which mostly drowned out the few people yelling queer and faggot at me. I hit a good stride, ran through some unattractive neighborhoods, and let my mind wander. As my running app hit four miles, I realized I had better turn around because I was mostly running away from the resort and would have four more miles back. The last couple of miles were a struggle under the late afternoon summer sun, and I was relieved when I saw the resort ahead, and already aroused thinking of what Sir had in store for me next.

I made my way through the parking lot, panting, and back to his poolside tent. I was a sweaty mess. I stunk. “Let’s see your app, boy.” I showed him that I had run just over eight miles at 7:24 per mile, thinking he would be impressed. “I said five miles, not eight. Don’t you listen, boy? Obedience is doing what you’re told, not taking initiative.”  I was still panting. All I wanted was some water and a shower, but I knew that I would not get off so easy. I wanted to quit this game, give up, rest, get my dick out of Sir’s cage, jump in the pool, recuperate, have a cocktail, and watch the action around me. But I agreed to be Sir’s slave until Monday, and I was positive he would not let me off the hook. I allowed my negative disobedient thoughts to pass as I listened to his next set of orders.

“You need to spend some time thinking about obedience, boy.”

“Yes sir.”

“I can’t leave my shop here, but I found someone to take care of you for a bit. Say hello to Tony.”

A stocky young guy came over. I had not seen him yet that weekend. He had on an orange rubber harness, black rubber shorts that were well filled out in front, and sneakers. His dark hair was cropped short and his eyes hidden by dark aviators. I wanted to lick the sweat off of his nipples right there. He smiled. I smiled. And I followed him back to Sir’s room.

“Tom said I can do whatever I want with you, as long as I leave you locked up with all of your holes filled when I’m done. Sound good?”

“Yes, sir.”

He let me take a shower first.  I dried off and Tony handed me a full body rubber neck entry body suit, then helped me into it with squirts of lube. He pushed me over the bed, unzipped the back zipper, and went through a variety of plugs trying to decide which to insert. He held up a massive red plug, way too big for my ass, and asked if I wanted that one. “Please, no!” I begged. Thankfully he put it down and found something more suitable, stainless steel with a narrow neck designed for long term wear. I had one like it at home and knew from experience how filling it would be once my ass closed around the narrow neck and held the heavy mass of stainless inside. He lubed it up and shoved the plug in my ass unceremoniously. He asked how it felt, would I be able to keep it in for at least a few hours. Did I want something bigger? I was ok, so he zipped up the rear. He stood me up and unzipped the fly, pulling out the chastity device with my dick engorged inside. Tony bent down to lick the bit of precum leaking from the small hole at the end of the metal tube, then produced a little plug that screwed into the head of the chastity device, penetrating my dick about an inch. I winced at this unfamiliar feeling. “Tom did say every hole, and I am pretty sure he meant that one too.” He zipped up the front again, then found some earplugs. He handed them to me to plug my own ears. He grabbed a complicated rubber hood. It had a thick posture collar built in and nose plugs with tubes attached. He handed it to me to put on myself. I jokingly asked him, “Uh, what if I refuse?”

“You won’t refuse!” he barked loudly enough to hear clearly through the earplugs.

I paused for a minute. Why was I doing this to myself? He took notice. “Ok, here’s the deal, boy. You’re not going to refuse because you fucking love this. And because that device is staying on your dick long after this weekend, and if I tell Tom you resisted, he will add another month to whatever duration he already has in mind.”

Fuck, I just met this Tom, and I did not agree to any kind of long term keyholder situation. I reluctantly put on the hood. Adrenaline and fear coursed through me as I tightened the laces. I’d signed up for a weekend of fun, what am I getting myself into? Tony completed the job by double checking the laces and then buckling down three straps. He told me that he was going to insert a gag, but only after he exploded in my face. He pushed me back against the headboard until I was sitting up, then stood on the mattress straddling my torso and began rubbing my face so I could feel his hard dick through his rubber shorts.  He teased me, grinding against my mouth and letting me feel his body with surprisingly unsecured hands. I felt at his ample ass, pulling him ever tighter against my face. I felt between his ass cheeks and found something firm. His ass was plugged too. He purred like a cat when I pressed on the base of his plug, and then quickly pulled back so he could take off the shorts and slam his dick into my mouth. He fucked my face aggressively through the small mouth opening of the hood, pressing me hard against the headboard. He grabbed my hands and pinned them above my head as he jackhammered away, deep into my throat. I heard his sweat dripping onto my rubber suit and took in the sweaty smell built up from his dick being encased in rubber in the Florida sun.

He took a break for a moment, pulled me downward until I was horizontal on the bed, and told me to stay put. The room went silent, as I could not hear what he was doing through the earplugs. I felt him doing something next to me on the bed, and then felt him slide me over on top of something. He slipped my legs and then torso into a sack, then seated my arms into pockets in this sack, and zipped it up to my neck. It felt like thick neoprene, totally encasing me so that the only skin uncovered was my mouth.

He then resumed fucking my face and I lay there nearly immovable like a gimp. I felt his load fill my throat a minute later and then he just held his rigid dick there as I swallowed. He pulled out and replaced his dick with a long penis shaped gag, and buckled that onto the hood.

“Did that taste like a lot of cum, boy?” he asked him loudly. I shook my head. “Let me tell you a little secret. You know that tube on your dick?” I shook my head again. “Tom locked it on me at this event last year. It did not come off until Friday, when he found his next victim. You.”

I started freaking out, struggling against the sack and yelling into the gag.

“How’s that year’s worth of cum taste now?”

I heard Tony laughing.

I heard the door slam.

I laid in silence wondering what the fuck I had done.

That was three months ago, and I have had almost no contact from Sir since the weekend ended.

 

Metal would like to thank the author, JR, for this story.