Self Bondage Roulette

The following is a true story, believe it or not. I let my fantasies become a little too real. Anyways I thought others might enjoy the absurdity I put myself through. 

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Over the past few months I’ve started getting into some simple self-bondage ideas to create a little more excitement in my boring life. But today I decided to really go all out. The outcome of the predicament I would put myself in would be entirely beyond my control. The idea of not knowing what would happen once I locked myself up got me hard just thinking about it. 

The predicament I would be subject myself to is as follows:

1. I would use two pair of cuffs to lock each one of my ankles to the back two legs of the chair I would be trapped in.  This forces my legs to be completely open allowing an unimpeded view of my manhood. 

2. Each of my arms would likewise be cuffed to the back two legs of the chair also, though each pair of cuffs will actually be connected to the chair via an electronic timer lock. This is how I would be able to get free. I chose to use an electronic timer on each arm just in case one failed to work. I would probably set the timers to an hour or two. 

3. I would be positioned directly in front of my laptop, the webcam positioned to see everything except my face.

4. A simple program I wrote using AutoHotKey would then dictate how the rest of my self-bondage session would go. The program begins by choosing a random number between 1 and 100.  

5. If the number is below 5, the program ends.

6. If the number is between 5 and 50, the program activates the a website called dirtyroulette.com and I get shown to viewers across the world for 10 minutes

7. If the number is between 50 and 99, the program will activate the dirtyroulette website but with no time limit. I would have to wait for the electronic timer to release my cuffed arms.

8. If the number is 100, I am in trouble. I wrote this part in my code mainly just to create a genuine sense of excitement and fear. If the random number is 100, the program will pull up an application that is connected to my phone. My phone will have the Grindr app already loaded up. The program will click the profile of the first guy listed (the closest person to my location) , and then it will click the message icon. It then Pastes into the message box the following - “Hello, I know this sounds weird, but if you have gotten this message, it means I have lost my self-bondage game. I am currently locked to a chair for the next hour. A program I wrote has sent you this message, you have my full permission to come over to my apartment at 462 Riverdale Lane Apt 34 and do whatever you’d like with me. The door is unlocked.”

With everything finally prepared and tested properly, all that was left was having the spare time to actually follow through with my plan. And today, on this beautiful lazy Saturday, I finally decided to go for it. Waiting a week allowed me to spice up a few things too. I undressed and then put on a skimpy red mini dress I bought off Amazon. And then I put on thigh high stockings and high heels. For some reason I always got off from the idea of being caught dressed like this, and absolutely being absolutely humiliated. Just putting on these clothes had already gotten my dick hard, poking up the whole mini dress. 

I placed the chair in position in front of my laptop and begin locking my ankles into place. My legs now spread out pushed dress above my waist and my boner saluted the laptop in front of it. Almost forgetting I grabbed my tv remote, just barely in my reach and clicked Play. A collection of Sissy Caption videos I had saved to a USB disk over the years began playing.  I set the two electronic timer locks to an hour and attached them to the legs of the chair. Before cuffing my wrists to them I reach over to my laptop and began the program. It would now choose a random number in 60 seconds. I cuffed my wrists to the electronic locks and the waiting game began. I was now stuck in this embarrassing position for the next 60 minutes. How far my embarrassment would go depended entirely on the next minute.  There was only a 1% chance of the GRINDR outcome but the fact that it was there and in the realm of possibility for me had my heart pounding. I waited, I could do nothing else. 

The dialog box appeared on screen. The random number chosen was 100. My mouth hung open, my stomach dropped to the floor, my eyes stared unmoving, dumbfounded by the screen. My arms instinctively tried to reach for the laptop. I couldn’t move them more than a few inches in any direction. The program navigated to the application that my phone was connected to. NO NO NO.  Grindr was suddenly right in front of my face.  The program clicked the first profile on the page. OH MY FUCKING GOD. The man in it looked like some kind of middle aged jock. His face wasn’t in his profile pic. At least not some old creepy guy thank god for that at least.  It said he was 800 feet away from me, a short walk. The program navigated to the DM screen and it pasted my pre-written message into the box and hit enter. It all happened in less than 10 seconds. I sat there still dumbfounded, heart still racing as the entire world seemed to be at a standstill now. I calmed my breathing and realized I had completely lost my erection in my panic. I created this whole fucking idea to create my own sexual excitement and now I was the least horny man on earth while I contemplated how much of a fucking idiot I am. 

I consoled myself by realizing that nobody in their right mind would take that message my program sent seriously anyways. Literally has to be the dumbest shit ever to read. That message had a 1% chance of being sent. But someone  reading it, actually taking it seriously, and then even being interested? That has to be one tenth of a percent chance of happening.  

A Grindr notification sound went off.  Oh no……

“Sounds hot, I’ll stop over in a bit”, the message read.

This literally cannot be happening. WHO IN THEIR RIGHT MIND WOULD RESPOND LIKE THAT??!?! I shook violently in my chair but only managed to hurt my ankles and wrists and almost tip over which could have been bad. A broken or dislocated limb was the last thing I needed right now. I took slow methodical breaths to calm myself down. This was happening. There is nothing I can do to stop it. I had never had any gay experience in my entire life and this is going to be how I have my first one. Only I could do something like this. I laughed to myself.  I looked at my tv for the first time in awhile, noticing one of my more favorite porn videos was playing. I laughed to myself again. Whoever this man was, he was going to talk into here and see a guy dressed in a mini dress locked in a chair, watching sissy caption videos. I threw my head up in repressed laughter. Only me.

15 minutes had passed. This guy might not even show up or was just fucking with me. I got myself worked up for nothing. I allowed myself to relax and enjoy the videos on my screen. I was going to crank a big one out after I got out of here. My boner was back and I wanted  nothing more than to be able to furiously stroke it. The sound of a door knob rang throughout my entire universe. No… 

I wasn’t facing the door but I could turn my body just enough to watch the door open. The man walked in. He walked in as if it was his own apartment.  I turned away unable, un-wanting to make eye contact. My humiliation fantasy had become a reality. Here I was dressed in women's clothing and completely exposed, helpless, my cock pointing skywards, oozing precum.

“Well fuck me sideways, you weren’t kidding”, the man said walking into my living room and approaching me as a sissy caption video played on my television. 

I let out an instinctive chuckle without knowing I was about to. “Yeah.. this is uhh… embarrassing”, I managed to squeak out.

The man walked in front of me, and we looked at each other. He was not the least bit flustered while I knew my entire body was glowing red from humiliation. He looked about 35, he was gruff, he was well built, and he was everything I could ever have asked for. His eyes looked me up and down, lingering on my cock for more than a few seconds while I could do nothing to stop him. 

“It’s my god damn lucky day, god damn boy.”

I let out that same awkward chuckle again, unsure how to respond in this absurd situation. “I guess it is” I said, and then dumbly followed it up with  “What are you going to do?”

He looked as if he was genuinely considering my question as he continued to eye down my entire body, sparing no part of me. He reached into his pocket, pulling out his phone. He pointed it at me and I heard the camera shutter sound go off.  My body burned even hotter as the realization set in that this man now owned the most humiliating photo of me ever. He lowered the phone and looked at me again. “It’s like I won the goddamn lottery.”

I blushed and awkwardly looked down not sure how to handle anything anymore.

The man carefully positioned his phone on the table in front of me. I watched as he activated the front facing camera and carefully centered myself on the screen. Oh nooo, this just keeps getting worse… He clicked record.

He walked in front of me, less than a foot away. He towered over me, his crotch, directly in front of my face. “I am going to facefuck the living shit out of you”, he coolly said in a tone so firm it demanded no response, no argument. 

He unbuttoned his jeans and stepped out of them, tossing them to the corner of my living room. He then dropped his boxers unleashing in front of my face the first cock other than my own I have ever seen. It was absolutely mammoth and he wasn’t even hard. HOW THE FUCK IS IT THAT BIG. My own cocked hardened even harder than I even knew it could. But my cock was being ignored. Whoever this man was, it was clear it was his cock that was going to get the attention. 

“Don’t start being shy now, get to work”, the man said and I realized I had just been staring for probably a bit too long. 

“Wha…what do you want me to.. to do exactly”, I asked like an absolute dumbass.

The man answered simply without making me feel any dumber than I already felt, “start by licking it, get me hard boy”

The scent of his manhood had infiltrated my nose by now and the idea of licking it seemed like a good one. I wanted nothing more than see if it tasted like it smelled.  I got to work, for the first time in my life placing my tongue on the dick of another man. Electricity bolted through my body as I made contact. His cock was hotter than I figured it would be and yes it did taste as nice as it smelled. I bobbed my head up and down each side up his dick licking every inch of it. It rewarded me by growing even larger, giving me somehow even more cock to rub my tongue against. I glanced up at the man to see if he was enjoying it and and he stared back down into my eyes, I glanced back away too embarrassed by eye contact. I put my focus back on the only thing that mattered at this moment in time, pleasuring his cock.

The man grabbed me by the hair on the back of my head, pulling me away from his cock. “Let’s get to the real stuff now” He said and somehow instinctively, maybe it was the hair pulling, I knew to open my mouth.  The man pushed my head back forward onto his now fully erected cock. The head of his penis smashing against the back of my throat. Oh my god, a man’s cock has just entered my mouth. It tasted like heaven and was so unbearably HOT. He pulled my head back, his dick exiting my head, I gagged for a moment before his gigantic dick was back in my throat. He moved my head at his will back and forth on his cock for awhile while I could do nothing but accept it. Saliva was pouring out of my mouth, clinging to his dick with each thrust, flowing down my chin and onto my dress. I had no idea I could even make this much salvia. After, who knows how long, he relented and pulled his cock out of my head. I gasped for air, my chest rapidly expanding and contracting as my lungs tried desperately to get oxygen back into my system. Until now I didn’t even realize I needed air so badly. My face and chest was covered in my own spit. 

He wiped my face off showing an almost endearing display of care for me before I realized what the real purpose behind it was. He grabbed my cock with his spit soaked hand and began to furiously stroke it. OH MY GOD.

I threw my head back in pure ecstasy and this random stranger jerked me off in a way so violent that I thought my head was going to explode. My arms and legs pushed viciously against the cuffs holding them in place.  Right when I thought I was about to cum the man suddenly stopped stroking me. Allowing to momentarily think again, though the only thing I could think about was HOW I NEEDED TO CUM!

“NO, DONT STOP! PLEASE”, I PLEADED WANTING THE CLIMAX TO MY ECSTASY.

The man smirked, “you will get what you want but not before I get what I want” He put His mammoth cock back in front of my face.

I wasted not one second. I lunged my head onto his cock and began sucking the absolute fuck out it. My lips clung to his girth as if my life depended on it. My tongue massaged every centimeter of his shaft as my head bobbed back and forth like a jackhammer on meth. Finally after God knows how long, I felt an eruption of fluid entering the back of my throat and I realized that I had just swallowed this stranger's cum without a second thought. I could feel his body convulsing as it happened and for the first time today it felt like I was the one with all the control. I sucked him completely dry until well after his convulsions stopped, and then I sucked some more, not wanting it to be over, but he eventually pulled his manhood out of my mouth. 

“God that was some good head”, the man said, walking over to his boxers and jeans, He began putting them on. 

I was once again trying to catch my breath, but I still needed to cum in the worst way.  “Are you going to.. To finish me off?” I asked dumbly, not sure how to actually ask or demand that he did. 

The man laughed and walked over to me. He knelt down next to me and reached for the electronic timer and I heard the subtle beeping of buttons being pushed. “In 4 hours and 15 minutes, you’ll be able to handle that yourself”.

I shook violently in my chair as the realization set in that he just increased the time until my locks would release, but he just smiled, grabbed his phone from the table in front of me and began walking to the door. 

“YOURE A FUCKING DICK!!” I blurted out in unmitigated rage. 

The man turned back at me, “I would be a little bit nicer moving forward if I was you” and he shook his phone lackadaisically towards me. “I’ll be in touch” he said as he opened the door and walked out, leaving the door a few inches ajar as I sat locked in my chair with porn videos playing on my tv, dressed like a dumb fucking slut covered in bodily fluids for the next 4 hours.