Down the Sissy Rabbit Hole

I hated to actually do it, but I did a nice trace of eye liner on each eye. Holding my eye that way was really uncomfortable, but the look was totally worth the discomfort, especially when I was able to get the wing on the outside of my eye to really accent my eye shadow. I couldn't always get my liner right, but this time it turned out well.

I then did some color on my cheeks, not a lot, just enough to give me a little highlight. I moved finally to the lips and I went with a bright, scarlet red. I filled in the outside of my lip, tracing to fill in the whole lip, and blotting off the excess. I admired myself in the mirror. Yeah, I looked like a super sexy slut. I would have started getting aroused if not for the chastity cage holding my nub down.

I went through my clothes looking for something in black and red. Then I saw my red and black corset and figured that was it. I pulled out the heavy PVC number with the steel boning. Not only was it restrictive, it was a glossy red and black striped PVC, so it looked amazing.

I wrapped the corset around my midsection, thrilling at the cool and slick feeling of the PVC on my skin. I loved my PVC clothes and the texture always got me feeling so sexy and feminine. I buckled the fasteners on the front, then reached around to pull the laces tight. I used my old trick of tying them off to my door handle, then pulling forward to get them nice and tight with the heavy stays pushing me in and giving me a nice hourglass figure. I grabbed a pair of falsies that gave me about a C cup set of tits. Not huge, but definitely way more than just the bit of cleavage that the corset gave me.

As I grabbed a red PVC thong and slid that up hold in my chastity cage, I looked through the dresses. I had several red colored and black colored PVC dresses, but I really wanted something that was super sexy. I pulled out a black dress that was completely open in the back. It looked like a normal mini-dress from the front and sides, then from the back it was completely open. It was one of the sluttiest things I owned. I actually felt my locked up clit dripping into my panties. At this rate, my panties were going to be soaked before I even left the house.

I slid the dress on and adjusted the straps in the back. There were four straps that connected across the back to keep the dress from slipping off. I looked in the mirror and I was amazed how the dress looked shiny and sexy from the front. As I looked over my shoulder at the back, I couldn't believe how trashy it looked. You could clearly see my corset, garters and even the thong in my ass crack. I can't believe I was even considering going out in this. I debated changing, but I knew I was in big trouble with this whole blackmail thing. I was hoping that if I showed I was all in, maybe they'd ease off and just play along with everything.

I looked through my wigs and remembered I'd been instructed to wear my blonde wig. I loved my black hair options and I had a red wig that actually looked very natural on me, but the guys always seemed to love a slutty blonde. I took the longest blonde wig I had that was about shoulder length. I brushed it out and tried to get it looking stylish. I fixed the hair piece on the wig and used my hairpins to attach it to my natural hair. The hair fell over my bare shoulders giving a very dramatic look, especially with the black of the dress.

I looked over my jewelry and decided to get some items out. First, I clipped a pair of large hoop earrings to my ear lobes. The dangling of the hoops was fun and felt very sissy. I next pulled out some of my necklaces. I had some chokers that were nice, but I decided to put on my silver jeweled necklace and pair that with my gold necklace that had a pendant that read 'CUM DUMP' on it. It was in very stylized letters, so unless you actually stopped to read it, you might not realize what it said. I pulled a few bracelets and rings out, but held off on them until later.

I looked over my footwear, but I knew there was really only one way I was going. It had to be my thigh high boots, I just wasn't sure which pair to go with. I had the stylish pair the were meant to be folded down at the top to show off the silver lining. They were a little too nice for this, besides I had a feeling I was going to want the covering on my knees. One nice things about thigh high boots, they act like built in knee pads.

So, I grabbed the pair of thigh high boots with the lacing up the back. The nice thing about these were the laces let them adjust to the size of my legs. I relished slipping my stockinged legs into the one and zipping it up. The soft and sturdy material hugging my legs. I squirted a bit with excitement as I zipped up the other boot, amazed at how sexy and slutty I felt. I was certainly getting excited about my coming adventure. I was scared sure, but horny was starting to take over.

I kind of wanted to paint my nails since there were few things that paired quite as well with bright red cock-sucking lips quite like bright red slutty nails. However, I didn't think I had time to actually do that, so I opted for some gloves instead. I decided to go with the cute PVC gloves with the lacy accents at the wrist. I love the look of elbow length gloves, but as over-the-top as this outfit was I figured I should go for a cute look with some part of it.

I put a few bracelets on one wrist so that when I moved my hand they bangled together. I slid on a few rings, most didn't fit with the gloves on, so I wore a few that were big and only fit with gloves on.

I then took a look at the sexy sissy slut in the mirror and was amazed at how much I was turning myself on. I considered unwrapping the keys and unlocking myself, but then I realized I'd probably never be able to match back up to the writing on the tape, which I guess was the point. I was pretty well fucked, or at least I assumed I was going to be.

I remembered to plug myself and see if that helped cool my fire. If anything, being so full just made me even hornier. I considered using one of my dildos and trying to scratch my itch that way, but I also figured I couldn't take too long.

I texted Master Clancy to let him know I was done slutting myself up. Naturally he wanted a photo and was very impressed with how slutty I looked.

"Very good, girl," came his message. "Since you were so good at getting ready, I'm just going to have you make two stops tonight instead of the five I was originally planning."

Well, I guess that was better than nothing, but still... two stops? Where the hell was I going?

"Thank you, Master. What do I do now?" I messaged back.

"Go to this address and message me when you get there. Make sure you bring your purse with your ID and your chastity keys," came the reply.

I had a real bad feeling in the pit of my stomach, but the throbbing in my locked up clitty won out of any terror I was feeling. I looked at the address and thought it looked familiar.

I hopped in my car. Thankfully I had a garage attached to my house, so I was covered from my neighbors seeing me all femmed up. I punched the address in the GPS and started driving, bopping along to the radio and trying to not panic too much. After a few minutes I realized I was heading to the main shopping center where the local Mart Store was located. I had a feeling I was going into the Mart, but with the way I was dressed, I was probably only going to be the third or fourth wildest person there.

Sure enough, I pulled into the parking lot. It was getting close to 9 pm, so the place was starting to clear out, but it was still pretty busy. I parked and shot Master a message that I was here.

"Go in, you'll be met by Master Carrol. Give him your chastity keys and do as he says," was the message back.

I knew I was heading in, but what was this about giving away my keys? Was I really ready for that? I guess it didn't matter if I was. If I was going to play this game, I guess I had to be prepared to give up control. It scared the hell out of me, but it really excited me, too.

Finally my arousal won out over my fear and I took the big step out of the car. I took a deep breath as I slid my booted legs out and stepped out of the car. I took a few hesitant steps on the parking lot. At some point, my heart stopped hammering in my chest and instead I could feel my clitty dripping steadily into my panties. The clicking of my heels on the parking lot thrilled me. To be out and doing a slut walk all done up was definitely a dream come true.

I was about as aroused as I could possibly be and still be caged. When I got to the front of the store and a few customers came out, I squirted into my cage I was so excited. I tried to keep my breathing and everything under control and just act casual. Y'know, act like I sashayed into the local Mart store in the sluttiest outfit possible all the damn time.

The couple going the other way gave me a quick look, but then continued on their way like I was just another freak at the Mart. That helped my confidence a lot and I settled into a nice slut strut into the store.

I looked around wondering where I should go. I strolled over to the clothes and browsed through them for a few minutes. The bracelets on my wrists bangling together pretty much every time I moved, drawing all kinds of attention from the people around me. I enjoyed looking through the clothes, but I didn't see anything that fit my style, so I moved on after a few minutes. If my bangles didn't draw attention the click of my heels on the floor certainly did.

I received lots of appreciative looks from the guys around, and even got a few smiles and whistles. That really had me feeling good and dripping into my panties just about every time. I was going to head over to the jewelry area and cut through an aisle where the personal hygiene items were. As I walked in, a staff member came around the corner and leaned against the end of the aisle.

He shook his head and smiled brightly at me. I guessed this was Carrol... I mean, Master Carrol!

I strolled over to him, smiling seductively, "Hello... Sir."

He smiled brighter at my femme voice. It wasn't great, but it was better than a lisp, he laughed a little, "Damn girl, you may be the sexiest sissy we've ever had."

I blushed a little, feeling the heat in my cheeks and I looked down and said, "Thank you, Sir."

"You really did go all out, didn't you? You look like a sissy hooker," he walked around and saw the back. "Or just a complete sissy fuck toy, whatever."

I nodded, "Yes, Sir. I wanted to be a good girl."

"Really? Because this outfit screams 'bad girl'," he laughed.

"Well, when I'm good, I'm good, but when I'm bad, I'm even better," I giggled nervously.

"Well, let's go see," he took me by the hand and led me to the side of the store. We went through a side door with a sign reading 'Authorized Personnel Only'. We came into a small hallway and went up a flight of steps. He used a badge of some kind and opened a heavy door. We entered a large area with a dozen or so TVs set-up. It took me a moment to realize these were cameras and this must have been the security room, or whatever they called it.

Master Carrol took me by the arm and walked me over by a desk, he set down some of the stuff he was holding on the desk with a loud thunk, that made me start a bit. He smiled at me, but it wasn't a nice smile, it was a predatory smile and heaven help me, it aroused me more than a little. I squirted from a mix of excitement and fear.

"First, I think you have something for me?" he held out his hand expectantly.

I looked confused for a moment.

"Wow, you must really be a blonde. The keys?" He insisted.

My heart sank. I had hoped somehow this was part of a game and that I'd be allowed to keep the keys. I knew damn well, they were going to someone else, but I still hoped. I reluctantly pulled the keys out of my purse and handed them over. And so help me, handing them over made my clitty absolutely throb in its cage. Was I really excited at the idea of handing my destiny over? Apparently I was since I could feel myself dripping in my panties.

"Good girl," he said softly and that made my heart race a little. "Now, show off for me. Walk that way and make some turns. Make it a sexy show."

I felt more than a little silly, but I wanted to be good, or bad, or good at being bad? Something like that. So, I turned giving him a good view of my ass in the dress. I shook my ass, making sure to take long slow steps with lots of hip movement on my heels.

"Nice, good one slut," he said, making me thrill with the praise. I did a few turns and stalked back on my heels, putting on as good a show as I could.

Master Carrol gestured me over and I walked up to him. He took my hand, putting his hand on my shoulders and pushing me down. I took the hint and got on my knees in front of him. This was far from my first time sucking a cock, but I was probably more nervous than I had ever been.

"Well, get my dick out, sissy girl. Show me what you got," Carrol smiled down at me.

I undid his pants and fished his hard cock out of his boxers. I gasped slightly and looked up at him in surprise. This thing was big! It had to be at least 9 probably more like 10 inches long and was very thick around. I wasn't sure this beast was even going to fit in my mouth.

"Yeah, I get that reaction a lot," he grinned down at me.

I swallowed nervously and wrapped my hand around him and started stroking with my gloves. I got my hand working as I gently reached out and began licking around his head with my tongue. I teased my tongue into his slit and tasted the pre-cum already dripping out.

"Make sure to look up at the Master you're serving, sissy girl," Master Carrol explained gently. "Remember you're pleasing your man. Its no longer about that little locked up nub between your legs." He held up my keys as he said this, shaking them teasingly. I squirted into my cage. Why did him belittling me get me so excited?

I looked up at him as I licked up and down his length, making sure to spend plenty of time tonguing his balls, licking along the sensitive underside back to lick and suck on the head. I made sure to get my hand working on his balls while I wrapped my lips around his head and sucked gently.

"Oh yeah, you are a natural cocksucker aren't you? Just made to pleasure cocks and take cum," he smiled down at me as he ran his fingers along my cheek. "You really are a pretty little slut. We will definitely keep you busy."

My clit throbbed with his words, but my heart hammered with fear. What else did they have planned for me? I tried to work past the fear and focus on pleasuring his cock. I took him in my mouth, working up as much spit as I could, getting him nice and wet, and taking more on each down stroke.

As I bobbed deep on his large cock, it didn't take long for me to bottom out and hit my gag reflex. Thankfully I'd spent lots of time practicing on my dildos, so I was able to focus and come back, hitting it a few times since he was almost as big as my largest dildo.

"Let me help you, slut," Master Carrol said grabbing the back of my head and shoving me onto his dick.

The extra force pushed him deep into my throat, and I flailed a bit as he went most of the way in my throat, but then tried to relax and enjoy the fullness. He pulled back, let me grab a quick breath, then pulled me back onto him. The sheer size of his meat filled my throat fully and with a slight push, he went balls deep, grinding on my mouth, using me for his pleasure.

He groaned as he pulled back. He controlled the action and worked his monster cock in and out of my mouth, my spit dripping all down my chin and onto my tits. As I rubbed my hands along his ass and legs, my bracelets would bangle.

He laughed at the noise at one point, "You certainly went out of your way to draw attention didn't you, sissy girl? Let me see your wrists."

As I kept working on his cock with my mouth and tongue, he took my wrists and did something with them. I thought he was putting more bracelets on. It took me a moment to realize he was buckling leather cuffs on my wrists. The metal D-rings were the real giveaway.

Suddenly Master Carrol pushed me back. I looked up panting, hungry for more of his cock. I was really getting into my sissy mind-state and I could get kind of cock drunk that way. He smiled and said, "Crawl this way, my little cock-sucker."

He led me over to a desk and pointed underneath, "Get in your new home, bitch." I looked up a little confused and he pointed under the desk and snapped, "Now!"

I jumped forward and crawled under the desk. I turned around and there wasn't a lot of space for me under there. He looked under the desk and smiled. He reached in and pulled my left arm up behind me, he did something and the cuff was hooked to the bottom of the desk. He then fastened my other wrist and I was stuck with my arms uncomfortably behind me. The angle did leave me hanging with my head perfectly available so that when he sat down and rolled his chair to the desk, I was at the perfect cock-sucking height.

It dawned on me that I probably wasn't the first sissy chained up under his desk, but the cock in my face got me back into my cocklust and I automatically started working on his member. He must have started doing something and was just letting me hang there and work on his manhood. I did hear him get on the phone at some point and I thought I heard the words sissy, so I tried to listen, but since I slowed down, that earned me a light smack in the face with his dick and "Did I tell you to stop, slut? You better suck like getting out of there depends on it."

Needless to say, I went back to happily working him over with my mouth. I'm not sure how long he kept me there, but I tried to mix up my speed and style, sometimes using just my lips and tongue, other times taking him all the way into my throat. At some point, he reached under and grabbed my head and took control, fucking my throat hard and fast. He was just using me as a pleasure tool and then he grabbed the back of my head and pushed all the way in, thrusting hard against my face, I could feel his huge cock pulsing shooting his seed straight down my throat.

Once he finished cumming, I tried to pull back, but he held me there and with my hands back at the angle they were I couldn't do much but hang there with his cock blocking my airway. I started to panic a bit, but then he pulled back enough to let me get some air.

I gasped and panted around his cock as he pumped his cock a few more times, wiping the last bits of cum across my face. I hung there, a bit winded, but also incredibly turned on. I really wanted to play with myself or do something to relieve the sexual build-up I had. Having just been used as a sex toy was really hitting my buttons. Oddly, I did hope my make-up still looked okay, but I doubted it.

"Clean me up, sissy," Master Carrol ordered and I happily licked the last traces of cum and spit from his still hard cock. Was it weird that I wanted him to fuck me? Of course, I was also nervous he was going to fuck me, but I also wanted it. I guess that's a good summary of how I felt about all of this. I wanted it, but I was scared it was going to actually happen.

He slapped my face a few times with his cock, laughing, "Good girl. Damn you really are a natural little sissy slut. You're going to be popular."

That statement thrilled and scared me. Master Carrol did something to my cuffs and released them. I took a moment, then I saw his fingers beckoning me and I crawled out. I knelt before him.

"As much as I'd love to keep you here and abuse you for a few more hours," I shuddered in a mix of fear and excitement. "Master Clancy has other plans for you. So, you're to go to the address he just sent to you and meet with Master Leveret. Master Leveret will have your next instructions. Oh, and stop and pick up some condoms on your way out."