Author's Note: Here is part 1 to a little story I came up with. Part 2 coming in the next week. I'd love feedback and ideas for part 2. I will leave my email unmasked for readers to respond.


Part 1

Background: I am a 18 year old boy, tight virgin ass, 6'4, exploring my kinks. I met a mistress online who said she is willing to introduce me to the world of kink.

I arrive at the destination and proceed inside. Mistress is nowhere to be found. There is a note with instructions on the floor. It reads:

1. Strip naked

2. Put on the chastity device and apply the lock

3. Insert the spider gag and tighten it, locking it after

4. Place both ankles in the spreader bar, and lock it in place

5. Place the hood on yourself, locking the zipper after

6. Insert the dildo gag, and lock it around the hood

7. Place the collar around your neck, it will lock automatically

8. Attach the leash to the collar and let it hang down your back

9. Handcuff your hands behind you and wait on your knees

10. Failure to follow instructions will result in punishment

11. If you chose to have a safe word, write it down below.

I take the chastity device and lock it on myself. Next I pull out the spider gag. It's rather large, but I force it behind my teeth and strap it on tight. I grab the spreader bar, and lock my ankles into it. It's rather long and keeps my feet 36 inches apart. 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. I grab the dildo gag next. It is only three inches long, but I notice it has a port on it so that it can be inflated. I then grab the collar. It is a metal band with 4 rings on it and air connection on the front. I hook the leash to the rear loop and lock it around my neck. It is a snug fit, but not tight. I handcuff my hands behind my back and drop to my knees. At this point I realize I never wrote down a safe word. I could only hope Mistress wouldn't take things too far.

After what felt like an hour, but was probably only 30 minutes, I feel a tug at my collar. I cannot see or hear anything. Mistress runs a small tube from the collar to a dildo gag. She presses a button on her phone and I feel the dildo gag expanding. It fills my mouth making any chance of speaking or squealing impossible. Mistress presses another button and I feel the gag grow down my throat. It reaches a length of eight inches and I find myself struggling to breath. Suddenly I feel the inner liner of the collar starting to expand. The collar gets tighter and tighter until I am barely able to breeze. I am pulled upward by my leash and am led down the hallway into another room. I am bent over, and my handcuffs are removed. Mistress also removes the collar. The freedom is short lived however, as I find myself quickly locked into medieval stocks. My dick is straining in my cage as the realization of my predicament sinks in. I feel the gag deflate and is removed. Next Mistress removes the hood and I am able to gather my surroundings. In front of me I see a wall of toys. Everything from floggers, to dildos and plugs. She drags the flogger cross my back as she walks around me. She then hits me 5 times across the ass with the flogger. I cry out in pain with each strike. I hear Mistress laughing behind me. I hear her speaking to someone and I freeze. Nobody else was supposed to be here. She walks back in front of me and calls for her friends to join her. I watch as two women equipped with massive strap-ons walk in front of me. I know one of them is Mistress but can't tell which. All I knew was my virgin ass was about to be ruined. My fear only worsens as three extremely hung men also 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 in front of me. I see nipple clamps, a massive dildo at least 12 inches long and 6 inches in diameter, a speculum, and another dildo, this one 24 inches long, and only an inch in diameter. She is also holding a cattle prod in her hands. She explains to her friends that I had not requested a safe word, and by the time I left I would be able to fit the 12 inch dildo in my ass, and the 24 inch dildo down my throat. I hear them laugh as one of them smacks my ass.

Mistress decides she wants to take my initial measurements first. The speculum is inserted into my ass and opened up to about an inch. I hear one of the guys laugh and mention how much stretching was in store for me. He then gets on his knees and pinches my nipples between his fingers. The pain is immense and I cry out. Immediately I feel the cattle prod zap my balls. It is enough to silence me immediately. I feel the nipple clamps being applied, followed by a sharp tug. I squirm in the stocks and my chastity twitches. I hear Mistress say to her friends that I seem to be enjoying this too much. She then stands in front of me holding the 24" dildo. She inserts it down my throat and makes it 8 inches before I gag. My chastity twitches again and she pulls it out. She instructs the men to rebind me to to the bench. The stocks open and I am carried over to the bench. They lay me on my back with my head hanging off the top of the bench. They run straps across my chest and bind me immobile to the bench. She lays a rubber hose and some weird metal rods on my chest. I feel a probing at my ass as a tube is rammed up it. The tube is attached to a large basin, and I feel the contents being emptied into my ass. I had never received an enema but I knew they weren't supposed to hurt like this. I notice that the basin was filled to the 2 gallon mark, and was filled with a pink liquid. Mistress must've added some cramping elements to the enema. She then removes the chastity device and I'm immediately erect. I watch as she grabs my cock, and squirts lube over the tip and down into my pee hole. She grabs the metal rod and begins to sound my cock with it. Im hit with a wave of pain and pleasure. While she's doing this, the tube is removed from the basin, and put into a drain in the ground. I feel the contents quickly drain from my ass. My attention was quickly brought back to Mistress however as she yanked the rod out of my cock. She goes over to the wall and grabs a catheter with an inflating bulb on the end. The catheter is extremely thick but is forced down my cock into my bladder. I feel the bulb expand and watch as my piss fills the tube. As it reaches the end Mistress twists a knob to stop the flow. I see movement above me and tilt my head back to see. Before I can even see it, a 6 inch dildo is slid into the spider gag. It is inflated and seals my mouth off completely. I watch as Mistress attaches the catheter to the dildo. She turns the knob and the contents of my bladder are emptied into my mouth. I have no choice but to swallow every drop. My bladder now empty, and my ass clean, the catheter and enema tube are removed.

I feel a cattle prod on my dick and it quickly shrinks down. I am placed into a new chastity device. This one however, is lined with spikes and included a two inch center piece that inserted down inside my cock. I am unstrapped from the table and the spreader bar is removed. I am carried and placed onto a table on my back. At the end of the table are two metal poles protruding into the air. At the top of the poles are ankle cuffs. My ankles are locked into them leaving my ass exposed. I hear Mistress put on her strap-on. She leans into my ear and explains how I am expected to swallow every drop of cum that enters my mouth, and that after tonight my ass would be plugged and locked so that it does not shrink back down. She holds the 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 brings her strap-on level with my ass. She plunges in and I yelp. As soon as I yelp however my head is tilted back and a massive cock fills my mouth. He grabs the sides of my head and pushes the entire length of his cock into my throat. I gag and he just laughs. He proceeds to viciously face fuck me as I am able to offer no resistance. He was the smallest of the group at only 7 inches. However, it was enough to gag me with each thrust. Mistress removes her strap-on from my ass, and thankfully nobody took her spot. She sits on my chest and places a clothes pin over my nose. The man fucking my mouth holds himself balls deep in my mouth and I am unable to breath. I feel him tense as he cums down my throat. He removes his cock and I swallow. I take a deep breath as another cock is placed at my lips. This guy was the longest of the three. I gag and feel myself on the verge of puking as all thirteen inches of him are rammed down my throat. He continues thrusting and thrusting as vomit fills my mouth. He tilts my head and lets the mix of saliva and vomit fall to the floor. Mistress points at something but I cant see what. I feel the collar being placed back on me. Mistress pushes a button on her phone and the collar tightens til I'm barely able to breath. I feel somebody at my ass again so I glance down. Its the third guy. He was 11 inches long but what worried me the most was his girth. Fully erect his dick was 2 inches in diameter. He squirted lube on my ass and slowly penetrated me. 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 nobody cared. Both cocks continued thrusting away. 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. The cock in my ass withdrew, as he walked over to my mouth to deposit his load. He attempted to fuck my face as well but was too large for the spider gag. I was relieved until I felt the spider gag 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. Each thrust completely blocked my airway. This must've entertained him as he then proceeded to hold his dick balls deep in my mouth as I struggled. He continued this cycle, removing his cock for me to take a breath. Then holding it all the way down until for over a minute. After ten painful minutes he shot his load down my throat and watched me swallow.

I was then placed back into the stocks. I felt the spreader bar placed back on my ankles. A anal hook was then placed in my ass, and ran through a loop on top of the stocks where it was connected to a bit gag. The bit is placed in my mouth and the rope tightened. Any movement of my head results in a sharp tug on my anal hook. I feel the nipple clips re applied, and this time weights are added to them. I hear Mistress say to me she will be back in two hours to continue to torment. Their dicks might not be able to get larger, but her strap-ons definitely could. The hood is then locked back on and I'm completely blind and deaf. All I could do now was try not to move too much as I awaited Mistress's return.