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Author's Note: Here is the continuation from my last story. I have included the first part again as well.
Part 1 & 2
Before I begin here's a little about me. I am an 18 year old teenage boy recently venturing into the world of kink. I am 6'4, 185 pounds, and athletically built. Recently I met a Mistress online who said she could introduce to this Kink world via submission to her. I told her I am an anal virgin, but have wanted to possibly try strap-on submission with some light bondage, as well as trying out some toys and equipment. I sent her a list of my desires, and limits, however it was very short with my little experience. The list was as follows:
Stuff I want to try:
* Bondage
* Collars
* Butt plugs
* Chastity devices
* Mild breath play
Hard limits:
* Anal stretching
* Impact play
Within minutes of initial contact, she responded that she would love to meet me that day. She told me to come over in an hour and we could discuss fetishes and maybe try a few.
I arrive at the destination texted to me and proceed inside as instructed. I enter into a dark hallway, but Mistress is nowhere to be found. There is a note with instructions on the floor. It reads:
Strip naked and place your clothes in the empty basket. Read the instructions thoroughly, and after completion I will come and get you. There is a basket of toys to your left.
1. Each item will lock automatically upon application with a beep. Complete steps exactly as below.
2. Put on the chastity device by inserting your dick into the cage tube, and closing the ring around the base of your cock, as well as one ring around each ball.
- If your dick is too hard, drink the liquid in the bottle, it will make you soft. Proceed and return to the cage before Step 9.
3. Insert the spider gag behind your teeth, tighten it around your head as tight as possible, and shut the clasp
4. Using the spreader bar, fasten the end loops around each ankle
5. Pull the hood over your head, and zip it closed. Then press the zipper into the clasp on the hood
6. Insert the dildo gag through the spider gag, twist it 90 degrees, locking it into the spider gag.
7. Place the collar around your neck, snapping the ends together, it will adjust automatically.
8. Connect the tube from the dildo gag to the nipple on the collar.
9. Place the second spreader bar around your wrists, with your hands behind your back.
10. Pull the leash from the ankle spreader bar, and attach it to the wrist bar. Then lay on your stomach.
11. Failure to follow instructions will result in punishment and/or inability to submit to Mistress.
12. If you chose to have a safe word, write it down below. If you choose to not have one, Mistress will base scenarios on perceived comfort levels.
I take the chastity device from the basket and turn it over in my hands. I slide it over my cock, but am too hard to lock it. I drink the liquid and proceed. Next I pull out the spider gag. It's rather large, but I force it behind my teeth and strap it on tight. Once the clasp is shut it seems to tighten more. This frightens me slightly, but only makes me hornier. I grab the spreader bar, and fasten the end loops around my ankles. It was at this point I realized that as stated, all clasps would not re-open. When locked a LED simply went from green to red on each item. It's a rather short bar, only a foot long. I grab the hood, and pull it over my head. It completely blocks out all light and noise, with holes over the mouth and nostrils for air. I fumble around blindly in the basket until I find the dildo gag. It is only three inches long, but the air tube on it frightens me. I then grab the collar. It is a metal band with 4 rings on it and air connection nipple on the front. I grab the collar and lock it around my neck. It tightens until the rubber liner barely touches all sides of my neck. I connect the plastic tube from the gag to the collar. With my dick now limp, I grab the chastity device. I slide my cock into the tube, and lock the rings around each testicle. I lock the second spreader to my wrists, and attach the hook from the first spreader bar. I lay on my stomach, which presses the chastity cage into me. At this point I realize I never wrote down a safe word, and in my current state I was unable to do so. I could only hope Mistress was being honest online and wouldn't take things too far. I start to roll to my side to relieve the pressure from the chastity device. Before I can do so, I feel both spreader bars extend until I am laying spread eagle on the ground. The cord between the spreader bars retracts pulling my feet up towards my wrists, leaving me in an eagle-hogtied position. Feeling a vibration from the collar, I realize that the dildo gag is expanding in my mouth. It completely fills my mouth making any noises from me unintelligible. I begin to panic but there is nothing I can do. After my mouth is stretched to the max, the dildo continues expanding down my throat at an impossibly slow rate. I begin to gag but it is no use, it continues until it is 6 inches from my teeth to its tip. Now unable to breath from my mouth, I feel the collar buzz to life again. This time however, the gag doesn't inflate, but I feel the inner liner of my collar inflating. It slowly chokes me more and more til even the smallest breath is difficult. I lay on the floor squirming awaiting my fate.
After what felt like an hour, but was probably only 30 minutes, I feel movement near me. I cannot see or hear anything. I feel the hook between the spreader bars release, and a leash attached to my collar. I am pulled upward by my leash and am led down the hallway into another room. Still spread eagle, it was a difficult walk. Mistress unhooks the leash, and my wrist bar is removed. I feel the collar deflate, but the gag remains at max. The collar is removed and I'm able to somewhat breathe again, as long as I use my nose. The freedom is short lived however, as I find myself quickly locked into medieval stocks. The liner of the neck portion of the stocks inflates, holding my neck in place. My dick is straining in my cage as the realization of my predicament sinks in. While terrified at what could happen, I was still extremely turned on. I feel the gag deflate and it is removed from my mouth. Next I feel the hood unzip and come off, and I am able to gather my surroundings, which appeared to be a dimly lit dungeon of sorts. The spider gag remains, keeping my mouth open wide as drool begins to leak from my mouth onto the floor. In front of me I see a seemingly endless wall of toys. Everything from whips and flogs to dildos and plugs ranging from the size of my thumb to some thicker than my thigh. There were entire shelves however, of items I had either never seen before, or only briefly in porn. I watch mistress remove a flog from the wall. She walks behind me and drags the flogger across my back as she passes. I have never had more than a spanking before, and I feared for what was about to happen. She proceeds to lash each butt cheek 5 times. I cry out in pain with each strike, the spider gag doing little to quiet me. I hear Mistress's laugh growing louder with each strike. Suddenly I hear male voices behind me. I panic, as nobody else was supposed to be here, we had agreed to a discrete session. She walks back in front of me and calls for her friends to join her. My fear for my predicament only worsens as three extremely hung men appear in front of me. Mistress walks to the wall, and grabs a few items, but I am unable to see what she grabbed. She turns around and places the items on the ground in front of me. I see nipple clamps, a massive butt plug at least 8 inches long and 4.5 inches in diameter, an anal speculum, and another dildo, this one 24 inches long, and only an inch in diameter. She is also holding a remote in her hands. She explains to her friends that I had not requested a safe word, and as a result, by the time I left I would fit the 8 inch dildo in my ass, and the 24 inch dildo down my throat with ease. I hear them laugh as one of them grabs my ass. Lightly pressing a finger to my sphincter in the process.
Mistress asks me to confirm to our guests that my ass was virgin. I remain staring at the ground when I hear a beep from the remote, followed by a shock from my chastity cage, and I quickly nod my head. The speculum is inserted into my ass and results in a sudden wave of pleasure at the new sensation. Slowly the speculum expands, straining my ass. As the pain begins to become unbearable, it is pulled from my ass. The speculum is held in front of me, and I see that she managed to open it almost an inch. I hear one of the guys laugh and mention how much tearing was in store for me, being the smallest of the guys was an inch and a half thick. He then gets on his knees and pinches my nipples between his fingers. The pain is immense and I cry out. Mistress holds the remote in front of me and presses a button. The neck liner of the stocks expands, nearly cutting off my air. It is enough to silence me immediately. I feel the nipple clamps being applied, followed by a sharp tug on their connecting chain as they are connected to a loop on the floor. I squirm in the stocks and my chastity device twitches. I hear Mistress say to her friends that I seem to be enjoying this too much, and something needs to be done about it. She then stands in front of me holding the 24" dildo. She inserts it down my throat inch by inch until I gag on it. She slaps my face and shoves it down until she gets about a third of it down my throat. My chastity twitches again and she pulls the dildo out. She instructs the men to remove me from the stocks, remove the nipple clamps, and hang me upside down by the spreader bar from the chain hanging from the ceiling. Once I am hanging, the chain retracts into the ceiling until my finger tips are two feet above the ground. I feel the collar placed around my neck. Mistress then slides an arm binder up my arms, fastening it as tight as she could. I feel a tennis ball placed in each hand, and am told to hold them. Next, latex mittens are stretched over each hand, followed by one more enveloping them both. I am unable to move my arms or fingers in the slightest. I am lowered to the ground and carried over to the bench. They lay me on my back and place a foam block under my head so that I'm stuck staring down at my body, chin to chest. They remove the spider gag, and replace it with a large ball gag. My jaw immediately cramps as the 3" ball was far too large for my mouth. After being forced behind my teeth, the straps to the gag are run under the bench before fastening so that my head is now completely immobile, the ball forced deeper into my mouth. Next straps go across my chest and stomach, and my spreader bar is clipped to a ring in the floor. I feel my arm binder secured to the underside of the bench. I was now completely immobile and at the mercy of Mistress and her three friends. She lays a tangle of tubes and some thin metal rods on my chest. I knew the thicker tube was more than likely an enema, but had no idea what the metal rods or small tubes were for. I feel a lubed finger at my sphincter that quickly enters my ass. Thankfully, it is removed quickly, but the thicker tube quickly replaces it. One of the men squeezes the pump and I feel the end of the tube growing inside me, making it impossible to expel. The other end of the tube is attached to a large bag, and I feel the contents being emptied into my ass. I had never received an enema but I knew from porn I had watched that they weren't supposed to hurt like this. Mistress notices my discomfort and explains how she added peppermint to the water to increase cramping. As the enema bag reaches the halfway point, about 2 liters left, the flow slows to a stop. The bag is then squeezed forcing the remaining two liters inside me. I can see my stomach expand as the cramps become unbearable. Once the bag is fully empty, a valve stops any liquid from flowing back up the tube. Mistress climbs on me and sits on my stomach, making the pressure even greater. She removes the chastity device and begins stroking my cock until it is hard. I watch as she then grabs the tip of my cock, and squirts lube over the tip, making sure to stretch my pee hole and squirting more lube inside. She grabs the thinnest metal rod and begins to rub it around the tip of my cock. I now realized the purpose of the sticks: cock sounding. Slowly she inserts the sound and I'm hit with a wave of pain and pleasure. She proceeds to slide the sound in and out, sliding deep enough to touch my bladder, but not enter it. After about two minutes, she grabs another sound. Skipping the three middle sizes, she grabs the thickest one and starts to stretch the inside of my cock. This time, she doesn't go slow. The sound was half a centimeter thick and she continued to fuck my penis harder and faster. I scream in pain but only a muffled moan escapes the ball gag. While she's doing this, the enema tube is detached from the bag, and put into a drain in the ground. The valve remained closed however holding the four liters inside me. My attention was quickly brought back to Mistress however as she yanks the rod out of my cock. She grabs the smaller tube, a catheter with an inflating bulb on the end. The catheter is thicker than the sound, but is forced down my cock anyways, into my bladder. I feel the bulb expand inside my bladder, and watch as my piss fills the tube. As it reaches the end, Mistress twists the valve to stop the pee from spilling out the end of the tube. I see movement above me but am unable to tilt my head back to see. The ball gag is removed and I close my aching mouth. I feel a slap on my balls and when I open my mouth to yell, a dildo gag is shoved in my mouth, this one making a complete seal around my lips. Again the straps are ran under the bench locking my head into place. It is inflated and seals my mouth off completely. I can feel with my tongue that this gag has a hole down the middle, assumedly to allow me to breathe. I watch as Mistress attaches the catheter to the hole in the gag. She turns the valve and the contents of my bladder are emptied into my mouth. I have no choice but to swallow every drop or choke. I feel the contents of my ass emptying as well and glance down to make sure the enema tube was still pointed down the drain. My bladder now empty, and my ass clean, the catheter and enema tube are removed, but the gag remains.
I watch in horror as a cattle prod is used on my cock and it quickly shrinks down. I am placed into a new chastity device. This one however, is lined with spikes and included a curved 2 inch sound that was inserted down inside my cock. My balls were not locked in this version of the device though. Mistress then takes my caged cock in her mouth and begins licking the cage. Every twitch from my cock trying to grow resulted in immense pain from the spikes, as well as the curved sound. I am unstrapped from the bench and the spreader bar is removed, followed by the gag. I am carried and placed onto a table, again on my back. At the end of the table are two metal poles protruding into the air. Along the pole are cuffs. My ankles and legs are locked into them leaving my ass exposed at the end of the table. Straps are again ran down my body binding me to the table. This time however, instead of a foam block for my head, the section of the table under my head is tilted down, leaving my head slightly upside down and staring at the wall of toys. The spider gag is installed, with the straps ran under the headrest as done with the bench. I watch as Mistress puts on a strap-on, a small one thankfully, about 6 inches in length and an inch in diameter. She also grabs a wooden humbler. The humbler is attached to my balls, and then stretched until resting on top of my thighs. Any movement results in a sharp pain from my balls. She leans into my ear and explains how I am expected to suck off her friends and swallow every drop of cum that enters my mouth, or I will be punished severely. She then holds a metal butt plug in my face. It was 4 inches in diameter and appeared to be able to expand further and lock into the users ass. I watch as she twists the knob expanding it to a 7 inch diameter. She tells me that I will leave with it locked in my ass, so my ass doesn't shrink back after all her hard work, and I'd be forced to return in the future if I wanted it removed. I watch as she brings her strap-on level with my ass. She plunges in and I yelp. As soon as I yelp however my head rest is lowered further, leaving my head completely upside down, and a massive cock fills my mouth. He grabs the sides of the table and pushes the entire length of his cock into my throat. I gag and he slaps me. He proceeds to viciously face fuck me as I am able to offer no resistance with the spider gag. Thankfully he was the smallest of the group at only 7 inches long. However, it was enough to gag me with each thrust. I feel the strap-on make one final thrust and then remove from my ass, and thankfully nobody took her spot. She then sits on my chest and places a clamp over my nose. The man fucking my mouth then deep throats me, and I find I am unable to breathe with every thrust. I feel his cock tense as cum gushes down my throat. He removes his cock and I swallow, out of fear of punishment if I don't. He spits in my mouth and demands I swallow that too. I take a deep breath as another cock is placed at my lips. This guy was the longest of the three at a staggering thirteen inches. I gag and feel myself on the verge of puking as he ever slowly moves inch by inch down my throat. He gets it all in, and holds it there for 30 seconds while I gag and start to vomit. He tilts my head and lets the mix of saliva and vomit fall to the floor. I hear a beep as the rubber liner expands, this time greater than before, I had to breathe my absolute hardest to get even the smallest amount of air, even without a cock in my mouth. I feel somebody at my ass but my head is held down by the gag and I can't see who. I quickly realize it is the third guy. He was 11 inches long but what worried me the most was his girth. Fully erect his dick was over 2 inches in diameter. He squirted lube on my ass and slowly penetrated me, doing as his friend did to my mouth and going inch by inch slow as ever. Once all 11 inches were inside me, he began thrusting in and out, faster each time The pain was immense, however I was quickly distracted by the return of the thirteen inch cock down my throat. Barely able to breathe from the collar, I was being spit roasted by two massive cocks. I immediately tasted vomit in my mouth, but this time he didn't care. Both cocks continued thrusting away as I desperately tried to spit the vomit from the gag between deep throats. I felt the cock in my mouth pulse as he reached his climax. He too shot his load down my throat and watched as I swallowed. He wiped his cock across my forehead and slapped me across the face. The cock in my ass withdrew, as he walked over to my mouth to finish in it as well. He attempted to slide his large cock down my throat, but was too large for the spider gag. I was relieved until I felt the spider gag being removed. I didn't even have time to close my mouth as he rammed his cock in. I felt my throat expanding to its max as he pushed his way in and all the way down. Each thrust completely blocked my already limited airway. This must've entertained him as he then proceeded to hold his dick balls deep in my mouth as I struggled for air. He continued this cycle, removing his cock for 2 seconds for me to take a breath. Then holding balls deep down my throat for what felt like minutes. After ten or so painful minutes he shot his load down my throat and watched me swallow.
Mistress told her friends they were free to leave after they helped her reposition me. The arm binder is removed, followed by the mitt holding my hands together. The collar deflates and is removed, as I am placed back into the stocks. The lining of the stocks quickly expands limiting my air once again. I felt the spreader bar placed back on my ankles, and locked in place to the ground. A anal hook with a 2.5 inch ball at the end was then forcibly squeezed into my ass, and a connected rope was ran through a loop on top of the stocks and laid by my head. The men left the room and I returned my attention to my Mistress. In her hand was a bit gag. I opened my mouth knowing a chastity zap would follow if I didn't. She placed the bit between my teeth, and loosely strapped it around my head. Before I even had time to process how loose it was, I feel her loop the cord attached to my anal hook through the bit gag strap and pull hard. Immediately pain shot through my ass and mouth. The rope was then tied taut to the stocks. Any movement of my head resulted in a sharp tug on my anal hook, and any movement of my ass resulted in the gag digging into my cheeks. I feel the nipple clamps being applied, ran through a loop in the floor, keeping them pulled harshly downward. She walks over to her wall and grabs a few more items, hiding them from my view. She puts a blindfold over my eyes, and ties it around my head. I feel a small hook going into each nostril. She runs the string from the hooks over my head and ties it to the stocks, keeping my head straining upward. Next I feel her remove the chastity cage. My cock immediately hardens. She locks metal cuffs around my balls, and adds metal weights until I squirm. I feel something being slid over my cock, and then hear a small motor humming. Mistress explains that she needed to go get some more supplies, and while she was gone the device was going to drain my cock of cum. I realized the stored cum was probably gonna end up inside me by the days end. She then returns to the wall and grabs a paddle and a funnel attached to a gag. I am presented with a choice, she will fill the funnel with my vomit and saliva on the ground and make me consume it, or I can refuse, and accept my punishment. The thought of eating my own vomit from the floor seemed worse than a few hits from the paddle, so I refused. She sets the funnel on the ground, and proceeds to hit me with the paddle 50 times. My ass felt as if it were on fire. Every hit sent me lurching forward, and as a result of my bondage, I was met with the yank of the nipple clips, my head forced upwards by my nostrils, as well as the bit gag and anal hook forced deeper inside me. She returns the paddle to the wall, but picks up the funnel and returns in front of me. The bit gag was removed, and the funnel gag locked in place. Mistress looks me in the eyes, and asks if I'm thirsty. Without caring for the response, she holds the funnel below her, and proceeds to fill it with her piss. Holding the funnel above my head, I was forced to swallow every sip. She then quickly removed the funnel gag, reinstalled the bit gag, and tightened the connecting rope. As she walked out the door she yells back to me that she will return in two hours, and that she had a special prize in store for me.
What felt like an eternity later, I heard footsteps behind me. I hear my Mistress laughing at my obvious pain from the bondage. She grabs the flogger from the wall and circles me with it. I hear the penis pump turn off as Mistress holds a bottle of my cum in front of me and removes the blindfold. She circles me again, this time using the flogger on my ass, back, cock, and face as she walked. She says to me that before I'm sent away for the night I will be able to fit the locking plug in my ass, expanded to at least 6 inches internally, as well as taking the 4.5" thick plug with ease. Removing the bit gag, she tells me if I make a sound I'm getting a 12 inch dildo gag locked down my throat. She starts untying me and removes my penetrators. When she's done removing everything, I remain bound in the stocks with the spreader bar, nothing else. The stocks' liner is deflated, and they are unlocked. As I struggle to stand, I glance towards the door, wondering if I could make a run for it. No sooner had I looked I felt an immense shock coming from my cock as mistress kicks it. I quickly returned my focus to my Mistress who places the collar back on me. I am told to lay back on the table and cuff my ankles and legs to the metal poles. When she approaches me I immediately see that she had put on a strap-on. This one twelve inches long and three inches in diameter. She runs the straps across my body, pinning my arms at my side, once again binding me immobile to the table. The head rest remained level with the table. She lubes up my ass, this time sliding 4 fingers inside me in the process. She barely gets the massive strap-on past my sphincter when I yelp. She withdraws immediately and disappears out of sight. As she approaches she is holding something behind her back. She grabs my hair and yells for me to open wide. I can only quickly see what she was holding before she shoves a 12 inch dildo gag down my throat. Gagging immediately, my Mistress didn't seem to care. She ran the straps under the headrest locking the massive dildo down my throat. I start to squirm as I am barely able to breathe. She pinches my nose and says she will let go when I am still. I freeze immediately and she lets go of my nose. She returns to the end of the table, and lines up her strap-on with my ass. She slams it in and doesn't stop til all 12 inches are buried in me. I scream into my gag but no sound came out. She continued to pump and pump my ass. The pain was so immense I was on the verge of blacking out. When she is satisfied my ass is thoroughly stretched to accommodate the 3 inch thick strap-on, she pulls out. She walks out of view again and returns holding a flared butt plug, also 3 inches thick. She shoves it in my ass and it stays put. She makes a comment about me not closing back up but the pain is too great for me to even notice. By this point I am no longer gagging on the dildo locked in my mouth so she removes the gag and wipes my spit across my face. Again, I'm presented with an ultimatum. If I make her cum before she makes me cum, I will be allowed one hour with one of her female slaves to do as I wish, but if I cum first, then someone I know would be joining her as mistress for the remainder of the night, and maybe even forever. I ask if I may have my hands free to assist me and an immediately met with a slap on the face. I am told a slave does not make requests. She climbs onto the table and rests her pussy in my face. I immediately begin licking, trying my hardest to make her cum. She begins to lick my cage resulting in the spikes digging into my hardening penis. The chastity device is removed and Mistress begins sucking my cock. I soon realized I was on the brink of orgasm and would surely lose. As I felt the pressure build and build I tried my best to not cum. My Mistress sensed this however. She then grabbed the base of the butt plug, and ripped it from my ass. The extra stimulation sent me over the edge and I came into Mistress's mouth. Due to the milking only a few drops came out, but it was enough. I had lost. Mistress got up and retrieved the funnel gag from the wall. Locking it on me, she spit the cum down the funnel and into my mouth. She then grabbed my cum bottle from the floor, and poured its contents into the gag, choking me with her hand to ensure I swallowed. Removing the funnel gag, Mistress disappears to the wall again. This time when she returns she has the nose hooks, nipple clamps, and a new weird metal device in her hand. She presses a button on the remote and the collar stirs to life. The rubber expands and begins to constrict my breathing once again. This time it didn't stop like it had before. The rubber inflated more and more until I was completely unable to breathe. As I began to panic and thrash around Mistress lowered the section of the table beneath my head so that I was facing the wall again, assumedly for more throat fucking. She grabbed two chains from the head rest, and attached them to the collar. Removing the slack, my head was now stuck downward pressed to the headrest. She inserts the nose clips and pulls them towards the ground, tying them to a loop beneath the table. I could not even move my head in the slightest without tearing my nostrils. With less than a minute til I blacked out, I hoped Mistress would deflate the collar. Instead she grabbed the metal contraption I had seen earlier. It appeared to be a gag is laid across my mouth. She begins to turn the screw on the side of the device and it opens up in my mouth. She twisted it open until my mouth was as wide as it could go, then made one more turn to add to the suffering. She stood there admiring her handy-work for several seconds, finally deflating the collar as my vision began to blur. She looks down at me and says just one more thing before I let our guest in. I watch her grab a handful of wires and a blackbox from the shelf and lock in onto me. She sets the box on my stomach and I see it is a electro-stem machine. She slides a rod down inside my cock, and connects it to the machine. I then watch as she sticks pads to my ass, chest, and balls, connecting wires to them as well. She presses a button and I am shocked by the devices. I hear a doorbell and my Mistress looks at me. She says the shock program will last thirty minutes while she gives our guest the tour. She then leaves the room.
As Mistress and the guest enter the room I recognize the voice of the guest. It was my ex girlfriend Kenzie whom I cheated on. The one girl who hated me most in this world. They walk into view and Kenzie smiles. Mistress explains how she did some research while she left me bound for two hours. Once she realized I had an ex who hated me deeply, she knew she just had to invite her over. I try to form words but only sounds come out. I watch as my mistress gives her remote to Kenzie and tells her to push the red button. Immediately the collar inflated leaving me with minimal air. She presses another button and the rod inside my cock zaps me. While I laid there asphyxiating and in pain, Mistress gave Kenzie a tour of the equipment, and toy wall, as well as letting her pick out a strap-on. After learning I had been stretched to three inches so far, Kenzie picks a massive strap-on from the wall. It was most certainly not going to fit. From what I could see its diameter was 4 inches, with a length of at least 16 inches. I watch as my mistress picks out a strap-on for herself. Hers was only 3 inches thick, but at least 24 inches in length. I hear a beep as my collar deflates. I listen as Mistress explains to Kenzie that I have no safe word, so she was allowed to do anything she wanted to me. Kenzie lit up as she ran and grabbed a paddle from the wall. Thankfully, mistress stopped her, but shortly followed it with a promise she could use it later, when I was bound in a better position. The two girls took their positions at both ends of me, Kenzie choosing my ass as her strap-on would surely destroy me. Mistress hands a bottle of lube to her, who laughs and sets it on the ground. She wanted this as painful as possible for me. I am so focused on relaxing my ass I don't even notice Mistress's dildo at my lips. I see it just as Mistress slides it down my throat. Kenzie watches in aw as Mistress forces every inch of her strap-on down my throat. I start gagging and immediately throw up. But Mistress just stands there without pulling out even an inch as Kenzie laughs. There is nothing I can do except breathe as mistress begins thrusting in and out, making sure to keep at least 12 inches in my mouth at all time. With this, Kenzie begins to force her strap-on into my ass. Before it was even in, I began moaning in pain. Kenzie proceeds to slap my balls until I get quiet. Seeing as I was not going to get quiet, I watch Mistress click her remote inflating my collar to the point of no airflow. Now completely silenced, Kenzie thrusts forward hard, not only destroying my sphincter as it is stretched to 4 inches, but also getting all 16 inches deep inside me. Both girls continued to thrust in and out for two minutes, before deflating my collar and allowing me to breath. Even then, mistress only deflated the collar while holding all 24 inches of her strap-on down my throat. The next twenty minutes was a vicious cycle of being destroyed in both ends, while the collar blocked all air for two minutes, deflated for thirty seconds, then repeated the cycle. When Kenzie finally pulled out, my ass was ruined, stretched to take a girth of 4 inches, I knew it would never be the same. My collar was left deflated and I gasped for breath as the girls removed their strap-ons. My break was short lived forever, as I watched as both Kenzie and mistress grabbed new strap-ons from the wall. Kenzie, now equipped with a 24 inch long strap-on positioned herself at my face. As she smacked my face with it a few times, I could see it was 3.5 inches thick. Way too thick for my throat, I knew that, like my ass, it was going in no matter what. I hadn't even realized Mistress positioning herself at my ass. As she held her strap-on up to my ass, I heard her joke to Kenzie that if her 4 inch cock could fit, then my Mistress's 5 inch thick could fit as well. I heard the collar beep again, this time restricting my air flow to about 25%. The girls decided they would make their first thrusts at the same time, tearing both openings as they went. Being that my ass had already been torn 4 inches today, I felt Mistress lube my ass with a numbing gel, as well as sliding her fist in me a few times. With both extreme strap-ons positioned at my openings, I listened as they counted down from 3 and thrusted hard. I don't know what hurt worse. Both girls had buried every inch of their strap-ons harness deep, and were just standing there holding them in while I bucked and squirmed. As before, both girls made sure to get every inch inside me with every thrust. After ten minutes of me writhing in pain as both girls fucked me as hard and fast as they can, Kenzie finally pulled out of my mouth. She asked my Mistress to use the bathroom but my Mistress had a better idea. I heard a beep as once again the collar restricted my breathing to zero. Already out of breath I became light headed immediately. I lied there as my Mistress removed my mouth stretcher, and quickly strapped on the funnel gag. As the collar deflated, my first clear vision was Kenzie standing in front of me filling the funnel with her piss. She then proceeded to hold the funnel above me, and opened the valve, watching as I struggled to swallow it all. Kenzie asked again if she could try the paddle and my mistress happily agreed. She began unstrapping me from the table as Kenzie grabbed her items of choice from the wall. I was half carried, half drug back to the stocks. My collar was again removed. After I was locked in the stocks, and the spreader bar locked to my ankles and the ground, Kenzie placed her items on the floor in front of me. She had chosen the paddle as well as a leather belt. Mistress then grabbed three more items and laid them on my back. I had no idea what she grabbed, only realizing what they were as they were applied. Mistress inserted the expanding butt plug, expanding it to 6 inches so that even my 5 inch ass couldn't expel it, then locked it in place. Kenzie grabbed the next item, and held it in front of me to see. It was another strap-on, this one 18 inches in length and three inches in diameter. She then slid it down my throat, and flipped the harness over my head, using it as a massive dildo gag. The third device was nipple clamps. These ones had a shorter chain however, with a large loop in the middle. I felt weights being added to the loops, stretching my nipples downward. Mistress tells Kenzie she will be back in half an hour to teach her more tricks, and that she could do whatever she wanted to me as long as I wasn't removed from the stocks.
Kenzie circled me a few times swinging the belt in the air before finally stopping behind me. She lashes me, bringing the belt down hard across my back. She continues this for another thirty or so strokes before getting bored. I hear the belt fall to the ground as Kenzie picks up the paddle. My ass still stung from earlier but Kenzie didn't care. She proceeds to beat my ass with the paddle until I feel blood dripping down it. I watch her grab the blindfold and put it on me. She returns to the toy wall, and begins placing items on the ground in front of me. I can't see what she is grabbing, but can hear her excitement as she looks through the items. She removes the blindfold and I see a pile of toys on the ground. She picks up a horse tail plug and walks behind me. Without even bothering to shrink it back down, she rips the locked plug from my ass, and replaces it with the tail. She explains to me that she always wanted a pet horse, and was going to make me hers. Next she grabs a pair of boots that look like hooves. The spreader bar is removed, only to be refastened above my knees. She slides my feet into each boot. The boots keep me in a permanent tippy-toe, and place all my weight on my toes. The dildo gag is removed and I begin to speak only to be slapped across the face. She holds the bit gag in front of me and I open my mouth. She attaches reins to the bit and ties them to stocks, forcing the bit deep into my mouth, and my head looking forward. She removes my chastity belt and I begin to get hard. She kicks it hard and I go limp. She stands back admiring her handy work when Mistress walks back in. She compliments Kenzie, and recommends a final touch. Mistress grabs what appears to be a leather horse head off a shelf and hands it to Kenzie. Mistress explains that is a hood, and allows the wearer to be blinded and deafened with the remote. My bit gag is removed and the hood pulled over my head. Inside the hood is a built in bit, this one wider with a curve in it that went to the back of my throat. It sat lower in my mouth keeping my tongue pressed down. Mistress presses a button on her remote and I'm unable to hear. I watch as she grabs a saddle out of the corner of the room. It's placed on my back, and tightened around me. I feel Kenzie climb onto the saddle and it takes all my strength to not collapse. Mistress clips the reins to my hood, and demonstrates to Kenzie that pulling the left rein causes the bit to shock me, and pulling the right shocks me via the tail plug. I stood there as Kenzie pulled both reins, over and over again. Kenzie hops off and tells Mistress she would love to learn more about being a Mistress. She presses a button on the remote and I am blinded. I feel Kenzie get off my back and rip the tail from my ass. My ass had begun to tighten again from the shocks, but quickly returned to a gaping hole.
For the next ten minutes I felt, saw, and heard nothing. Eventually I feel the saddle being removed, followed by everything else. When Mistress and Kenzie finished I had nothing on or in me, not even the chastity or spreader bar. I still remained locked in the stocks though. They stand in front of me and I notice that Kenzie had changed. She was now dressed in all leather as a Mistress. My Mistress explains to me that Kenzie has shown great interest in becoming a Mistress as well. As a result, it was decided that Mistress would train Kenzie using me as the submissive. At the end of the training, Kenzie would become my Mistress and that I would be serving as her slave for the remainder of my life. Before I even have a chance to respond, I see the remote in Kenzies hand. I stay quiet out of fear she'd suffocate me with the stocks. Kenzie opens the stocks and tells me to stand with my back to the bondage cross. I lean up against it and my two mistresses secure my arms, legs, and body to the cross. Next Mistress removes the pin from the cross, and tips it backwards until my body is parallel to the floor. I hear Mistress tell Kenzie that a custom crate had been ordered for me to sleep in, but for tonight, I would sleep bound to the cross. Mistress then tells Kenzie to chose what toys I needed in or on me for the night. Her face lights up as she grabs several items from the shelf and sets them below me. She picks up a new chastity device I hadn't seen before. Mistress explains it was like the other chastity devices, but more painful. This one requires the user's penis head to be pierced, and the cage locks through the hole. Mistress offers to perform the piercing and Kenzie happily agrees. I watch in horror as Mistress pierces a hole through my penis. The cage is applied, and I notice that even with the piercing, it still allowed for me to be sounded. With my dick now squished down into a tiny ball, mistress slides a catheter into my cock, inflating the bulb. She grabs a weird shaped dildo with several valves at the end. She puts it in my ass and both the parts inside me and outside me inflate, making a seal in my ass. The catheter is connected to the dildo, as well as two tubes from the floor. Mistress explains that my piss during the night will automatically flow into my ass. At 4AM, I could expect the hoses to turn on and until 6 AM, the enemas would fill my ass and bladder to the max, drain them, and repeat. She picks up the piercing gun one last time, and places small bars in each of my nipples. She walks out the door and tells Kenzie to follow. Kenzie places a blindfold on me and walk out the door. I try and sleep knowing I was in for a long day tomorrow.