Down the Sissy Rabbit Hole

I nodded, and gulped nervously. Here I was dressed like a total slut, I'm sure my make-up was a complete mess, probably looking like a used whore with cum smeared on my face, and now I was going to pick-up condoms? And go somewhere else? My heart hammered with fear, but my clit was rock hard in my cage.

I stood and adjusted my clothes to try and look somewhat presentable. I turned, grabbed my purse and was about leave when Master Carrol said, "Are you leaving, cunt?"

"Yes, Sir. You told me to go," I said, a little confused.

"Is there anything you think you should say, first?" he looked at me sternly.

Why did that look scare me but make my clit throb more?

"I-I-I.. I'm not sure, Sir," I managed to stammer.

"Since you're new, this will be your lesson. After you service a guy, you thank him for him for using you like a proper sissy and ask for his permission to leave. Make sure you're on your knees when you do it."

"Yes, Sir. Sorry, Sir," I knelt down feeling like a chastised child.

"You're just a sissy, I understand."

My cheeks flushed with shame, and I looked up, "Thank you letting me worship your wonderful cock, Sir. May this sissy leave?"

Master Carrol ran his hand along my face tenderly then said, "You're welcome, I look forward to you being back here. You may go, slut."

I stood and tottered my way back down the steps. I made sure to use the handrail for that trip down the steps. I stepped back out into the store and the bright lights made me realize my sluttiness was really on display. I look down and realized there was spit and cum all down the front of my dress. I just took a breath, wiped off as much as I could and started to make my way out.

I wandered back to the personal hygiene aisle. I got a few sideways glances from some patrons, but no one really stared too much, or at least not that I noticed. I was trying to find the condoms so I could get to my next stop.

I found the rubbers and grabbed a pack. I then made my way to the checkout. I had hoped they would have some of those self checkouts, but it was just rows of cashiers. Thankfully this time of night there were only a few working. I picked one cashier that was kind of by themselves. The cashier barely glanced at me as she rang up the box and looked as I handed her the payment. She processed it and handed me my receipt. I guess she finally got a good look and smiled, laughing slightly with a smirk and soft snort.

For some reason her laughing thrilled me so that I was dripping in my cage, but it also made me blush bright red.

"Have fun, don't do anything I wouldn't do," she called as I scurried out of the store, my cheeks flushed red with embarrassment.

I eventually hopped back into my car and sat there for a few minutes catching my breath. I tossed the box of prophylactics into my purse and fished out my phone. I saw the address of my next destination and started driving.

I realized I was heading slightly out of town. Was I going to someone's house? It looked like a shopping center or something on the map, so it was hard to say.

As I drove my mind wandered to where all of this was going and why being forced to do all of this was turning me on so much. I ran through the possible scenarios where I was heading, but pulling into the parking lot of an adult bookstore was not what I was expecting.

My heart sank as my clitty throbbed in its cage with my excitement. I'd always fantasized about going dressed to a bookstore, but this was a bit more than I was ready for. I looked around and was surprised to see a number of cars in the parking lot. I figured since it was midweek and later in the evening, things would be quiet.

I checked my phone, I was to meet Master Leveret and he was going to show me how a proper sissy slut was handled. That phrase terrified me and had me so hard my clit was straining the limits of the cage.

I took a deep breath and stepped out of the car. The sound of my heels clicking on the parking lot again instilled me with feeling of being a super sexy slut. I started strutting and feeling really good about being a proper sissy slut. I opened the door and entered the rather seedy looking place. I have to say, the fact that the place was so seedy kind of thrilled me even more. Something about being a proper sissy meant you would be on your knees on the sticky floor of a seedy establishment.

I looked around and saw a few racks of porn DVDs, some toys and magazines. There were also a number of guys milling about and all of them noticed me. I got several appreciative looks and even more hungry stares. My clitty throbbed as I realized this was going to be the next part of my night.

I looked and saw the clerk behind the counter giving me a half-smile. I strode over and smiled seductively, "I'm looking for Master Leveret."

"I know, sissy girl," he said still with that wan smile. "Do you have a box of condoms for me?"

I handed over the box from my purse and he just nodded, "Good girl. Follow me."

He stepped from behind the counter and walked to the back of the store. As we went back, the lights were much dimmer and I saw there were a number of doors leading into booths. I could hear the sounds of porn music and women screaming in the throes of passion, or at least faking it really well.

I could see a few of the booths had the doors open and it looked like it was basically just a booth with a bench and TV in it. I saw a few that had holes in them and realized these must have been glory holes. Was I going to be working a glory hole? That idea was kind of exciting.

We went down a hallway into a door labeled 'Theater'. We went through the door and came into an area with several hallways and I could hear more porn playing. I scurried along on my heels trying to keep up in the dim light while trying to take everything in.

I saw there were actually several theaters, each had couches, benches, chairs and even some tables. I could see a few people seated in the theaters, they followed our passing with interest. Oddly, the last theater was empty and there was nothing playing on the TVs there.

We turned just past the last theater and went into a small hallway that opened into a small room that looked like a larger version of one of the booths. I saw a picture of me on the wall! It was from earlier, I guess from the Mart? I was really confused what was going on.

Master Leveret did something and pushed the wall so it opened into the theater we had just passed. There was a small padded section where the wall opened.

Master Leveret turned and gestured me over to him, "Bend over here, sissy girl."

I walked up a little nervously, but I obediently bent over the small bench. Master Leveret grabbed my arms and held them up a little. A moment later, he did something and the wall closed back around my waist and trapped my wrists in there as well.

In this position, I was stuck halfway through the wall with my ass and mouth on either side, right at waist height. Oh my, I was going to be a through-the-wall public use slut. I could feel Master Leveret do something with my legs and then he pulled my legs to the side. He must have hooked the cuffs I still had on, and hooked my ankles to something since I couldn't close my legs any more.

A moment later he appeared around front, smiling at me. He reached down and ran his fingers gently across my face, "Oh yeah, you're going to be a popular little cock sleeve."

I shuddered with excitement and fear as he reached up and held a gag to my mouth. I opened wide and he shoved the large O-ring gag into my mouth.

He buckled the gag behind my head and said, "Its great that you wore that backless dress, I didn't even have to strip you down or hike up your dress. The good news for you is that its pretty late on a weeknight, so there will probably be a smaller number of guys to use you. On the weekends, you pretty little things get railed for hours until you're just a puddle of cum."

This statement had me throbbing in my cage. The idea of having multiple trains run on both ends was exciting me beyond belief. It also scared the hell out of me, as you could probably guess.

He stepped into the room and did something so that the TV came on. It was just a shot of a semi-dark room. I realized there was an ass and legs in thigh high boots showing on the TV. Oh shit! It was a video of my ass in the other room. I wiggled my ass and sure enough the ass sticking out of the backless dress shook, too.

Master Leveret did something and I realized there was a TV next to me, too. That one started playing porn and I could sort of see the gorgeous trans girl on the screen sucking passionately on two cocks. As you can guess, I was already dripping. Seeing this trans porn was driving me wild.

A moment later I saw something on the TV showing my ass and realized Master Leveret had walked in. He went over to my exposed ass and smacked me on the cheek with his hand. I could hear the smack muffled through the wall and felt the sting a moment later.

He then smacked my other cheek. I could see the red hand print on my ass as he made several more swats. This also had the effect of me clenching and releasing on the plug in my ass, so I was basically fucking myself with my butt plug. The combination of the bondage, the spanking and the plug had me buzzing and I felt like I was going to cum just from the spanking,

I didn't cum even though he spanked me for several minutes, getting my ass nice and red. He then pulled my thong down as low as it would go, which was really only down to just above my knees. He then ripped my plug out unceremoniously. I groaned into the gag as I watched him line his cock up with my asshole. He plunged all the way into me with one stroke.

My head swam with the pleasure and pain mix as my ass felt like it was torn open. He gave me a moment to adjust, then he started fucking me, slowly at first, but after a few minutes, he built to a speed where he was just slamming into my ass and I could feel his balls slapping on my ass cheeks, his hands gripped tightly around my hips. He was pulling my hips back as he slammed his cock deep in my ass, just relentlessly pounding my tight little hole.

This wasn't my first time being fucked, and since I used my dildos pretty regularly I was well used to having things up my ass. The pounding was starting to have the effect and I could feel a sissygasm starting to swell.

Before I could get off, Master Leveret pulled me back and thrust one last time, burying himself as far he could in. I could feel jet after jet of his cum shoot up my asshole. The feeling of being filled making me feel so much like a true sissy.

Master Leveret stood for several moments catching his breath. He eventually pulled out and a fair amount of cum spilled out of my ass and ran down my legs. I could actually feel it pooling in my panties down around my knees.

A moment later he came around front and stepped up to my helpless mouth. He put his deflating cock into my mouth and used my mouth to clean the last of the cum, lube and my ass from his cock.

"Good little sissy slut, I hope you're ready to get covered in the jizz of real men," he then pulled out and wiped his cock on my cheek before putting it back into his pants. "Enjoy your session, sissy."

I saw on the monitor that another guy was stepping up to my still dripping ass. He lined up and plunged into my wide open hole and started going to town on me. I could see several guys lined up waiting their turn. Then another guy stepped up to my ring gagged mouth.

My moaning from the ass fucking I was taking was cut off by the cock in my mouth. It only took a few moments for my oral lover to start pushing hard and getting into my throat. It took several tries and lots of gagging before he pushed my nose into his pubes and his full-length down my gullet.

As he held on, I started getting desperate for air. When he pulled out, I grabbed a big breath and he plunged back into my mouth. While this was going on my anal lover was steady plugging away at my backside, giving me a light swat every few strokes. It took a few minutes but eventually he blew his load in me, too.

Meanwhile, my oral lover was finding a nice pace where they were hitting my throat deep each time but I was still able to get a quick breath. The lack of air was giving me a weird high and I was starting to feel weird. Not exactly dizzy per se, just kind of spacey. This was taking the thrill of being bound and used to a new level and I could feel it building up in me like a fire burning slowly.

My oral lover slammed home, holding the back of my head in a tight grip and cumming deep down my throat as he kept pumping his hips unloading a huge load. He pulled out after a few moments and cum and drool spilled out of my gagged mouth, trailing down my chin and dripping down the wall below me.

I only had a few moments to catch my breath before another gentlemen caller stepped up, hard cock in their hand. They used the cum and spit dripping down my chin to lube up their cock and plunged it deep into my gagged-open mouth.

As he started working on my mouth, my anal lover suddenly grabbed my hips cumming in my ass. I couldn't feel any cum shooting in me, so I wasn't sure what was going on. I tried to get a look at the TV screen, but couldn't tell what was going on since there was the guy in front of me. I did realize there were three guys waiting after him.

I felt my anal lover pull out after a few moments. They then did something to my stocking top, I could feel something wet and warm against my leg. What the hell? I didn't have any time further to consider it before another cock was sliding into my now well-used ass.

After a few minutes of both guys using me, the build up I'd been experiencing crested and I had a sissygasm that made my head and clit both feel like they were exploding. The good news was, my reactions apparently set both men off and both off them filled me with more cum. Two more times my mouth and ass were each used as a cum dump before the line of guys was gone. Two more of the gentlemen also did something to my stocking tops. The last man also replaced my butt plug.

After the last guy finished in my mouth, he stepped away and I could see my ass and my face on the two screens. There was cum literally dripping off my chin and out of my ass. I felt like such a well-used sissy whore, but I was glad we were done.

Master Leveret stepped into the video of my ass, I thought for a moment he was going to use me again, but instead he opened the wall and unhooked my ankles and hands. I half-slid, half climbed off the bench I had been laying on. I was covered in a light sweat all over from the exhaustive workout I'd just had.

As I stood the cum felt like it was pouring out of my ass. My panties were still down around my knees, so I puled those up and realized a lot of the cum had pooled in them. They were drenched in semen, but so was the rest of me, so I slid them up. The puddle squishing against my cage and ass.

"How are you sissy?" he asked as he removed my ring gag.

"Full, Sir," I panted, suddenly feeling very tired. After I wiped my chin, I reached back and felt at my stocking tops. I realized they were condoms that had been tucked into my stocking tops.

"Yes, those are your treats, sissy girl. Drink up," he put the wall back the way it was originally.

He wanted me to drink three full condoms? I'd already swallowed multiple loads and I felt full. I couldn't imagine sucking down all that.

Master Leveret stepped in with his phone out, clearly ready to take pictures, "Once you drink those, you're done and can go home."

Well, that was an incentive. I reached back and pulled up the first condom, holding it over my mouth, the cum started dripping out slowly, so I turned it inside out and the cum poured out into my willing mouth. I swallowed all three condoms down and I actually burped up cum. That was a weird taste and feeling.

"Good girl," Master Leveret said. He pointed to the puddle on the floor and all the cum that ran down the wall. "Normally our sissies have to clean up every last bit of jizz, but since you were such a good girl, I'll let you go tonight. I imagine you're pretty full. Next time you'll lick it all up."

Master Leveret took pictures and offered me his arm, I leaned on him as we walked back out. More cum dripped out of my ass and full panties as we walked. Several guys laughed and cat-called me as we walked by. My face turning beet red with shame, but my clit also throbbed in its cage. How could something so humiliating also turn me on so much?

I trudged out to my car, looking forward to getting home and cleaning up. As I sat in the puddle of cum that my panties had become, my phone dinged.

I looked and saw a message from Master Clancy. It had several stills from the video of me in the wall and it just said, "Love the pics and video. Good girl. Rest up tomorrow and we'll see you Friday."

My heart raced with fear while my clit squirted into my drenched panties. I was so scared but also excited beyond belief. How far down this rabbit hole was I going?