A Late Night Stroll · Part 1 (1/2)
Next
I am by nature a very private person. I had kept my taste for bondage and pain to myself for my entire life until I met Cheryl, or as I call her now mistress. Now my tastes and my life are anything but private.
With no one to live out my fantasies with me, I do my self bondage and self torture in my basement. I have it all stocked with everything I need to bind and torture myself. I have a dedicated computer that I only used for connecting with women online and that runs punishment programs. I spend a lot of time down in the basement. I’ve had several custom videos made where the mistresses would lead me in torturing myself, but never had I ever played with a woman in real life. I had tried several times to gather the courage to ask my assorted girlfriends and one nightstands to indulge me in my fantasies but I always chickened out at the last moment.
Anyway, one night after a recent failure to ask for what I needed I decided to go for it. I contacted a woman that I had been emailing back and forth for years. She had done several custom femdom videos for me. Having never thought we would meet, I shared with her all of my fantasies, she knew everything about how I wanted to suffer. So I logged on to the kinky hookup site we had been using and rolled the dice.
Slavedan: Hello MistressC. We have been friends here for a long time and I would like to meet you in person. Since you know all of my kinks and you seem to share my tastes I thought you could come to my dungeon and we could play. What do you think?
MistressC: WOW! That sounds great. I would love to make you scream, beg and humiliate you.
Slavedan: Oh God, that made me so horny! I am so glad. When can you come?
MistressC: How about Saturday in three weeks? That will give you time to prepare.
Slavedan: Prepare? What do I need to do?
MistressC: For the first week I want you to jerk off into a jar three times a day. Save every drop. Then for the next week I want you to edge three times a day and you better not cum. Save as much of the precum as you can as well. I want you frustrated and horny. Then for the last week I want you to put on your smallest metal chastity device and lock it on. Mail the keys to me tomorrow so I have them when I arrive and you have no way to free your cock. That’s a whole week with your cock and balls locked up.
Slavedan: Yes mistress. I will do everything you demand.
And that was how it started, the most painful and humiliating night of my life.
So for the first week I did like I was told and a bit more, not knowing why I was doing it. I jerked off everyday to my favorite bondage porn while I had gagged myself as severely as I could stand. I love being gagged so much, the more cruel the better. After a week of milking my cock I had almost a cup of my own cum sealed in a jar that I kept in the fridge.
Then came the hardest part, edging for a week. MistressC had asked for three times a day but I did it four times a day at least. I made myself crazy. I would gag myself and hook up my estim and stroke and tease myself right up until the point of cumming and then suddenly I would whip my balls until the need to cum stopped. My cock would be dripping precum which would drip into the cum jar as MistressC had told me to do. I did this over and over often seven or eight times a day. By the end of the week I had more than a cup in my cum jar.
Masturbating and edging complete I took my smallest metal chastity device and put it on my cock and balls. I pulled my poor now black and blue balls through the ring that would surround and trap my cock and balls. Then I shoved my rapidly stiffening cock into the rigid metal penis sheath and quickly attached the sheath to the ring and fit the lock into the receiver connecting the sheath to the ring. I took the lock, whose key I had mailed to MistressC, and snapped it into place trapping my cock and balls for a week. I had never given total control of my cock and balls to anyone before. I had always used chastity devices for bondage, but I always had the key available. I was scared and excited and my cock was now as hard as it could get being crammed into the now painful chastity device.
I suffered the full week in the chastity device. I urinated with it on. I showered with it on. I had to go to work with it on. I slept with it on and suffered through the painful hardons my dry wet dreams induced. Then finally MistressC arrived. She knocked on my door and I stood gaping. She was every fantasy I ever had come true. She was absolutely beautiful. I knew what she looked like from the internet and she was stunning but in person, she was truly breathtaking.
She was dressed head to toe in shiny black leather carrying a large black leather bag. A tight long pencil skirt and a corset were the first things that caught my eye, her figure was perfect. The corset was tight but just enough to accentuate her curves in just the right way. A tailored leather top draped over her shapely breasts, thin enough to see her stiff nipple show through. Black nylons led down to her knee high stiletto heeled lace up boots.
Her wavy dark hair had a tightly cropped haircut that framed her angular face. Pale clear skin and full dark lips painted dark crimson were brought to life by her deep blue radiant eyes. I just stood and stared, my head filled with images of how I would suffer for her.
After a very long moment of me just standing there staring she spoke, “May I come in?” she said clearly and without emotion.
“Oh yes please MistressC! I am so sorry. Please come in,” I said apologetically.
“From now on call me mistress. And only speak when directly spoken to. Take me to your dungeon. I want to see you bound and gagged.”
I assumed since we had been in contact for so long she knew what I liked and what my limits were but to be honest I didn’t even give safe play a thought. I would do anything she wanted. I was hers to do with as she wished for as long as she wanted.
I took her directly to my dungeon and showed her where everything was. Bondage furniture I had built and bought over the years. All of my bondage equipment, leather, latex, gags, straps and rope. All of my pain toys, clamps, and my various CBT devices. Once she was acquainted with my dungeon she said “Strip, slave!”
I quickly took off all my clothes. I was left totally naked except for the metal chastity device which was now drooling precum and crushing my erection painfully.
“I assume you did everything you were told. I can see your cock is drooling already,” she laughed. “Let’s get to it then. I want you bound and gagged as tight as I can make it. I want this binding to really be painful and one you will never forget. Let’s start with a tight corset. I brought several things of my own in case you didn’t have the right thing.”
She went to her bag and removed a tall stiff black leather corset. I had never worn a corset before but I was excited to be bound wearing one.
“Turn around slave.” she said as she began to fit the stiff corset.
As she reached around me to bring the corset around the front of me her leather clad body pressed against me and I moaned out loud with the pleasure of her touch. She was warm and soft as birds but cold and hard as nails.
“I did not give you permission to moan slave. You will pay for that with an extra cruel gag. You better keep your mouth shut.” Her tone and attitude of control made my cock throb.
Once the corset was in place she began the long process of making it as tight as she could. She would tug all the laces tight starting from the top and work her way down. After the second pass my breathing began to get a bit labored. But she was far from done. She made three more passes of tightening the laces and grunting with exertion with every pull. The final pass she brought her knee up to the small of my back to use as leverage to get the corset even tighter. Now not only could I not draw a full breath, just breathing was painful.
She tied off the laces and said “Now that is a tight corset. I bet it is hard to breathe, aye slave?
“Yes mistress,” I gasped.
She grabbed my balls and gave them a vicious twist and she squeezed. “That was a rhetorical question, slave. It looks like I need to gag you now.”
I stood in quiet agony trying to breathe through the slowly fading pain in my balls. The gag was my favorite part. I couldn’t wait to be gagged by her. I had dreamed for three weeks of the cruel ways she might gag me.
“Where do you have the cum you were told to save? You may answer.”
“In the fridge, mistress.”
“Go get it while I get the first part of your gag ready. And bring me a large bowl as well.”
I made my way to the kitchen to retrieve the jar of cum. Even though I was not bound, moving in the excruciatingly tight corset was difficult and painful. I was in heaven. MistressC was so far everything I had hoped for and more. By the time I made my way back to the dungeon she had several things laid out on a nearby table.
Without speaking I put my head down and held out the bowl and the jar for her to take.
As she accepted the bowl and the nearly full jar of cum she said, “Looks like you were quite a busy slave,” she laughed, “good, all the more humiliating for you.” She smiled, cruelly.
She went to the table and set the bowl down and picked up a ziplock bag. “I brought you a treat slave. I know you’ll just love it.”
She opened the bag and took out four pairs of black lace panties. As she held them up to my face she informed me that the panties were her panties and they were all filthy. She had worn them each for days. She had wiped her ass with them. She had cleaned her toilet with them and she had pissed on them as well. She placed the disgusting panties in the bowl and twisted the lid off the cum jar and dumped my thick cum into the bowl on top of the panties.
She picked up a pair of disposable black latex gloves and stretched them over her hands. She began to mix the cum into the panties like a chef making a salad. She even wiped out the cum jar with a pair of her panties to make sure she got every drop. Once she was satisfied that she had all the cum and the cum had fully soaked the panties she said, “Open wide slave.”
Oh my God she was going to gag me with that disgusting mess! I thought I might throw up just thinking about it. I thought the gag was disgusting but at the same time I was getting more and more turned on at the idea of having that mess stuffed in my mouth.
She picked one cum soaked panty and stuffed it into my mouth. I immediately tasted my own cum mixed with urine. I retched violently as she laughed.
“Better get used to the taste slave you’re going to be gagged with these panties for a long, long time.”
She took the second pair and pushed into my mouth on top of the first pair filling my mouth with cum panties. Before she put the next pair in my mouth she said “Now the gag gets serious cum slut.”
She took the third pair of panties and sopped up a bit more cum leaving the last pair in the bowl. Then she began to force the cum soaked panty into my mouth. She had to pull my lips to the sides to get them all in. After much pushing and shoving they were finally all in. My mouth was literally stuffed with cummy panties. My own cum was slowly dripping down my throat. My gag reflex was kicking in worse and worse. I stood there trying not to vomit and my dick dripping.
“Now just one more thing and I’ll help you hold all those tasty panties in.”
She peeled off the latex gloves and pushed both of them on top of all the rest. She grabbed a roll of electrical tape and placed the end of the roll on my cheek. She began to wind the stretchy tape around my head right over the great wad of cum panties. Each turn went over the wad and was pulled tight forcing the mouth packing deeper into my mouth. When she had nearly a dozen turns she broke the tape and burnished the end flat against the side of my head. My lips were white and stretched to their limit with the cruel tension of the tight cleave gag.
“Aren’t I nice to help you hold all that in?”
I was too focused on trying to breathe and not to throw up to hear her question. The next thing I felt was my balls being squeezed and twisted once again. The pain tore through my body like a train wreck. I screamed wildly into the awful gag until finally she stopped crushing my poor balls.
“ I said, aren't I nice to help you hold all that in?”
I nodded wildly in agreement that she was indeed nice to help me out like that. Oh my God that hurt so much.
“So nice of you to say slave. As a reward I’ll cover all that tape with some more tape, I wouldn’t want you drooling and dripping cum all over can I?”
MistressC then took a roll of duct tape and covered my face from just below my nose to the tip of my chin in layer after layer of duct tape, each layer pulled as tight as she could make it. The tape dug deeply into my face causing quite a distortion of my face. My eyes were red and watering.
“Now for your ballet boots. Oh you are going to suffer with these but I know you love it.” she snickered evilly. I had told her several times how much I loved the painful restrictiveness of ballet boots.
I had a pair of ballet boots that I had bought to make walking more difficult during self bondage sessions which required key retrieval. They could be locked on so I would not be able to remove them once they started to get too painful. I had tied myself while wearing the cruel boots and forced myself to walk many times so I was very good at walking in ballet boots. Mistress C put the terrible ballet boots on me but not before she went to her bag again and came back with a small handful of uncooked rice which she sprinkled in each boot. The rice I knew would instanly become a torture to my poor toes. Boots all laced up tight, the finishing touch was a small padlock on each strap at the top of the boots. The boots were not coming off without the key.
She went about the task of collecting the necessary items to keep me standing and immobile while she continued my bondage. She set up my hoist and attached a noose she retrieved from her bag to the hook to the end of the hoist.
“Stand up slave.”
I stood up as best I could. Once standing my toes were instantly in agony. Sharp jolts of pain shot into my toes. All of my weight was now on the hard grains of rice. A small high pitched squeal escaped past my horrible gag. I heard a small laugh from MistressC. Somewhat wobbly, I was able to stand without falling but it took a lot of effort.
“Looks like you’re having trouble balancing. Here let me help…” she said with mock sympathy
To “help”, she pulled the noose over my head and pulled it tight around my neck. Then she took out the slack in the rope by cranking the winch. Neck stretched, I could stand without choking if I stood upright and didn’t move too much. Being unstable, I would lean to one side and strangle myself and I had to leverage my neck to right myself. This was scary but I trusted her.
Next she strapped wide leather ankle cuffs over the ballet boots and locked them on with two more padlocks. The short chain made standing without leaning even more difficult. With the ballet boots and my ankles so close together my balance was severely impared. Now I was choking myself almost constantly. I had to get control of my balance or I was in trouble.
As if reading my mind, MistressC said, “ You better figure out how to stand in those boots quickly or you are going to be in deep trouble. I know your toes must be killing you. Too bad. I am not going to take you down until I’m done and I’ve just started.”
I was beginning to worry. I didn’t really know her. What if she went too far. OH fuck! We didn’t agree on a safe signal.
She went to my closet of bondage items and returned with my waist cincher. This was basically a six inch wide strap that was designed to crush my waist. It had two long straps that went on either side of my cock and balls and the two straps merged into one at the back and buckled in the back. It’s purpose was to keep a buttplug securely in my asshole. MistressC fastened the cincher around my waist and pulled it tight. I grunted in pain as she did. Not satisfied, she again raised her knee to the middle of my back for leverage and tightened the cincher two more notches. Now my tiny waist already being crushed by the stiff corset was in severe pain. Happy with the severity of the cincher she secured it with more padlocks. She left the long straps dangle for the moment.
From her bag she produced a huge black buttplug. My eyes flew open wide. I had never had anything near that large in my ass before. I knew it was going to hurt really bad. But it was about to get worse.
“By the look in your eyes this is a little bigger than you’re used to. Good! I want this to hurt. Oh and did I mention it can be electrified? Yeah, it will be hooked up to the most powerful remote controlled estim on the market. It’s actually a large dog shock collar, the most powerful one on the market. I had another slave modify it for me. He made it deliver a much more powerful shock and added more switches to shock more devices. You’re gonna love you bondage slut.” she said with real joy in her voice.
“Gonna need a LOT of lube I think…”
Once she had slathered my asshole and the giant plug liberally with lube, she knelt down and placed the tip of the fearsome plug right on my butthole. I was shaking with fear.
“Would you like to beg me to not shove this thing up your asshole? It’s okay, you can beg me. I’d like to hear you beg.”
Instantly I began to beg and plead with her from behind my enormous gag. With unintelligible words I pleaded with her to not do it. I whimpered and cried my muffled pleadings. As I begged I could hear her giggling.
“Not a fucking chance slave, this is going up your tiny little asshole. Get ready, here it comes!”
OH PLEASE GOD NO!
With one hard shove she forced the buttplug into my ass. The pain was intense. The first push only made it about half way. She pulled it back out a tiny bit and shoved again. My scream made my throat feel as if I had torn something. The agony. But still it was not all the way in. So she backed it out a bit once more and gave such a hard push that it nearly lifted me off my feet. My head began to spin and I felt dizzy, the pain was so great. The pain took my breath away and I realized that I had to breathe or I would pass out. I sucked in air as hard as I could and began crying. The thing was finally in. It was huge. I felt so full and it hurt so bad.
She quickly grabbed the crotch strap and fed them on either side of my balls and then between my buttocks. She fed the end of the strap through the buckle in the back and pulled up sharply on the strap. This did two things, it forced the giant buttplug deeper into my ass and it also started my screaming again. The pain seemed to double. She went in front of me and did the same with the straps in the front of the cincher with the same reaction from me. She placed a padlock on each of the straps as well.
“Next time I’ll use the big one.” She laughed wildly.
I was in so much pain. I couldn’t believe she was doing this to me. I was scared, not role playing, I was really scared.
“Have you ever worn an armbinder before?” Before I could answer she continued, “I don't really care, you’re going to wear one now,” she laughed, “I brought one special for you. Lots of straps… Nice shiny black leather… mmmmmm… Just how you like it.” she teased “You are so stupid to not set up a safeword or negotiate what was going to happen. Oh, I guess you were just too excited to play with me weren’t you? Too bad. You’re at my mercy now and I am fresh out.”
“Put your hands together behind you, slave, and make fists.”
She took the roll of duct tape and taped each of my fists into useless stumps. Then she wrapped my fists together and continued wrapping all the way up to my mid-forearm. When she was done my hands were one useless taped package. She quickly fed the open end of the armbinder over my useless taped hands and pulled the armbinder all the way up my arms. To keep the armbinder in place she fed the shoulder straps up over my shoulders and fastened them tight. She now pulled the sides together as she began to lace the armbinder up. Just like the corset she tightened and re-tightened the laces until they were as tight as she could get them.
Laces tight and double knotted she secured the strap at the wrist and finished with a padlock. The elbow strap was next. This strap she gave it her all to get as tight as possible. I was pretty flexible for a man, but my elbows never came close to touching. When she was done my elbows were just touching. It felt like my shoulders were being dislocated. Of course she finished the strap with a little padlock.
Next she applied my leather body harness to secure my arms to my body. The harness went around my upper chest and my lower chest and around my waist. To keep the straps from slipping down all the straps were connected by a center strap that split at the top and went over my shoulders to connect in the back. She outdid herself with the cruelty of these straps. When tightened to her liking my arms were crushed against my body painfully. Breathing was very difficult, everything hurt and my chest was so compressed I c
A Late Night Stroll · Part 1 (1/2)
Next
