From Craving Cigs To Craving Cock Ch 04

Anal Fixation

The day of my tenth session with Mister Anderson was completely ordinary.

I got up, ate my breakfast of plain oats with the protein shake from my special bottle Willa had got me (it has a nozzle like the head of a cock!), and went to the gym for early yoga.

After yoga, I went to the bathroom and sucked a pair of cocks. I would have done more but I needed to go to work. Willa did come out and feed me a load she'd sucked right before I had to leave, she is so nice.

At work, Mister Haffner brought by two of his guys and I sucked off all three of them. Well, two, since Mister Haffner still likes to fuck my face. I had a lunch of more shake from my bottle, got all my work done early, and spent a few hours watching some videos and grinding my cage against my panties.

I was up to being able to walk in five inch heels, my corset training was going so well, and I loved my new tight butt! I was still working up the courage to wear a skirt to work, but I'd already started wearing a blouse. I just really wanted to show off my legs and the stockings that covered them.

After that Mister Haffner and another of his guys came by, and once I'd made them cum it was time to go lick Mrs Brown's pussy. I didn't even go home, just went right to the gym for pole class. I really wanted to fit in some time in room 4 before my appointment, but another slut was in there. He looked so surprised and cute, green eyes framed by curly brown hair, but I told him not to worry. He looked so embarrassed with that cock in his mouth, but I couldn't understand why. It was a big cock, it's hard to take one of those for a newbie.

I waved at Rebecca who was helping a nice young woman pick out a crystal necklace, and she waved back. The customer looked confused at me, and I understood. I was wearing my pole dancing clothes, all tight and pink with knee length boots and the word juicy across my ass. I didn't look like someone who needed Mister Anderson's hypnosis to be happy.

Mister Anderson was waiting, a broad smile on his face. "Welcome back," he said, "how are you feeling?"

"Great," I exclaimed, but then cocked my head. I needed to be honest with Mister Anderson. "Well, not perfect," I admitted. "I still feel, well, unfulfilled. Messy, I guess."

He nodded. "I thought as much. You've made a lot of changes in a short time, so there's certainly things you need to let go off. How about your work?"

I shrugged. "Well, Mister Haffner is bringing by some nice cocks to suck, including Henry, who's almost as big as you. But I guess otherwise I sort of feel unfulfilled."

He nodded, as if it made perfect sense. "But you like your time at the gym?"

I nodded eagerly.

"Good, good," he said. "There's a special sort of exercise I expect you will be a natural at. It's related to that unfilled, well, unfulfilled feeling you're complaining about. Everything will be waiting for you at home."

I nodded again, smiling.

"Now, let's begin," he said, and stood, removing his massive cock from his slacks. My eyes followed it as it swung back and forth, and my vision grew unfocused. I started to wish I could remember sucking his cock more clearly, but whatever Mister Anderson wants is what's right.

I snapped out of it with his cum drying on my chin and my jaw aching.

"Good, now, there are some new videos you will need to watch as well," he explained. "Put in your notice at work and clear your desk tomorrow. It's over the weekend but Mrs Brown will have someone waiting there to help you."

I nodded, and left without bothering to wipe up my face. As I walked out I saw a young man staring at me, and nearly drop the geode he'd been holding. I could hear Rebecca scolding him on the way out.

I found the package waiting for me at home, but not on the front door.

The package was inside, along with Willa. She was wearing a pink crop top and white booty shorts, and exploded into a hug as I entered.

"Oh, it's so good you're taking this step!" She cried as she embraced me.

She revealed the plain brown paper package, unopened. "You have to be the one to open it," she said seriously, with the most serious expression I'd ever seen on her.

I did. Inside was a tube of clear lube and a metal butt plug, the flared base covered in odd runes. But the symbol at the bottom reminded me of the one in Rebecca's altar, the one besides the venus and Mars symbols. Despite not knowing a single marking on it I knew it belonged to me, just as I had known the cage belonged to me.

Willa clapped. "Oh, perfect! It means you're like me! I knew we would become sissy sisters!"

Willa guided me by the hand to the bathroom, where she had a red bag and a long white tube set up. "This is an enema," she explained brightly, "you can do a little play without one, especially since your diet is better now. But for obvious reasons its always better to clean yourself out, I'll show you how."

Willa took the bag and showed me how to fill it, chattering as she did so. "Now, you can use all kinds of other stuff to change the sensation of the enema," she went in as the bag filled. "But normally you'll be just using body temperature water. Definitely not too hot, and too cold can be almost as dangerous."

She shot a little water into the bathtub, then fed the nozzle into her butt. I was entranced, her ass was pert and perfect, and it was so weird to see the bag slowly empty as she went into downward facing dog to give the water the easiest route down.

She danced around for a minute, "once you're feeling full, it's good to move a bit. You know, really get it going."

Then she expelled the waste. There was less brown in it than I expected, and I told her that "like I said, the diet and the shakes make us pretty clean anyway," she said brightly. "Now, it's your turn!"

I found at once the feeling of being filled up completely strange, but somehow perfect. I danced around a bit as Willa encouraged me, and then we both went again.

Once we were both completely clean, Willa took me to the main room and set my plug on the table. Next to it she placed her own plug.

"Now, once this goes in, you're going to keep it in almost full time," she said, pointing a finger in my face. "Not because it feels good, though it does. Because it's a sign from Master Anderson that we're his sissies, ok?"

She finished earnestly.

I nodded, bobbing my head, without a single conscious idea what any of that meant.

The metal plug didn't go in easy, and I endured several comments from Willa about being a tight ass. But after a few of my fingers and a few of hers, not to mention a lot of lube, I felt the plug slip past my inner ring of muscle and my asshole closed around the narrow tube.

Willa laughed, pulled a bit on the base, then spanked my ass. "You look perfect babe!"

Then I helped her, but I got the feeling that she didn't need the help and was humoring me. That was fine, I loved playing with her ass.

Once we were both in, Willa sat us on the couch, legs crossed. I got out a couple of my toys and found Willa had brought a two foot long double ended dildo. She clicked on the TV and we began to watch as we mindlessly practiced our blowjobs.

These videos were different, I realized at once. Before it had been more mainstream porn, now it was unmistakably amateur. Relatively well lit and well shot, but still amateur.

Also, rather than a man and a woman, or multiple men and a woman, or multiple women, or multiple of each, this time the girl getting fucked by a big black cock had a chastity cage swinging between her thighs that looked very much like the ones me and Willa had.

It took til the third video, where two guys were taking turns on a blonde bimbo with a fat ass and the tiniest cage I'd ever seen til I realized it.

"Hey, that's our pole teacher, Marcia Robinson," I said, taking my dildo out of my mouth with a pop.

"Mhmmhmmm," Willa said, clearly not thinking a confirmation required her to stop her task.

The next few videos proved it. The guys I started to recognize from the gym, and even when cis girls started to appear, I recognized them too.

When Willa's video appeared, we were both barely watching, each of us with a good eight inches of dildo down our throats as we worked on that double ended one Willa brought.

I pushed my mouth off the toy. "Wow, is that you?" I asked

On screen Willa, a little flatter in chest and ass than the sissy in front of me, was waltzing into a principal's office. She wore a school uniform that would have immediately given any catholic nun a heart attack, and bounced along in entirely impractical high heels. The camera was set in an upper corner of the room, unmoving, giving the video the air of a security tape.

After a short exchange between her and the older, balding man behind the desk, she got on her knees. He fished out a cock that was entirely unimpressive but Willa cooed and gasped over it like the professional slut she is.

I looked around the set and was impressed. I'd only ever been in a single principal's office in my life, and it had nailed the look down to the last detail. It wasn't until Willa had got on the old man's lap and he started to spank her that I realized why it seemed so familiar. It was the office of the local high school principal, and the old man...

"Wait a second," I said. "That is the real Principal Edwards!"

"Yup!" Willa said, removing the dildo with a pop. "Not a great cock, and not a real strong arm, but it was plenty kinky. He called me by the name of the current valedictorian, did you catch that?" She giggled.

I licked my lips. On screen Willa was begging the principal for something, then she rose and sat on his cock. After only a minute of bouncing on the old man's lap, he let out a sound half grunt and half yell. Video Willa immediately stood, turned and took the still jerking cock in her mouth.

I should have expected the next video, but it blew me away.

It was another tape, only this one of the locker rooms at the gym. As I watched, a very familiar sissy walked up to three handsome hunks, flashed her cage, and got on her knees.

"Oh, you're such a natural!" Willa said.

I was entranced at the candid video of me continuing through what I knew was my first blowbang. Not that a causal viewer would have guessed an inexperienced sissy could be sucking cocks like that with such gusto.

"Oh wow," I said, gazing at the screen as a fourth man joined in, nearly obscuring me. "I didn't even realize that other guys slipped in there."

Willa giggled. "I might have told him that if he cut his workout short, he could get head from a new sissy."

I looked over at her. "Oh, I can see all the cameras," she explained.

I nodded, taking that revelation in stride.

Once that video ended I was ready for some fresh revelation that would blow my mind, but instead there was just a prompt asking if we were ready to continue.

"Oh, and now, we train our cute little butts!" Willa exclaimed, reaching behind her and removing her butt plug with a wet plop.

"That's why I wanted to get all your toys nice and wet," she grinned at me. "Don't worry, we start slow."

Being an anal Virgin, I could hard believe it when Willa took an eight inch dildo with seemingly very little prep. I was trying with my smallest, the six incher, and I was gasping.

When we ended, me and Willa showered together and she assured me I would be a 'dirty little butt slut' like her soon.

We ended the night cuddling on the sofa as the videos looped.

The next day I went in to remove my stuff from the office. It was really just a single box, but Mrs Brown had been nice enough to send Henry to help me out. I sucked his cock once more in the office for old times sake and gave him the card for the gym, and asked him to swing by.

I hadn't realized it at the time, but over that weekend Willa moved in with me. I had a few minutes of worry about it, but she mentioned something about Master Anderson telling her to, and the worry faded at once. And it was fun!

My next week was a blur between spending half my time at the gym, where I found myself even more excited than before knowing that my antics were being recorded, and home, where several days of anal training assisted by Willa stretched me out.

I only understood why Willa seemed to love it so much once we got to the larger dildos, but the first time a big toy touched my sissy button in my ass I was in heaven! I almost passed out humping my toy on the couch. And Willa assured me a real cock, with a man holding me down as he pounded my ass, was much much better!

The day of my eleventh appointment with Master Anderson was completely normal. I still couldn't take all of the toy Willa described as 'big boy', but I could manage most of it. Willa told me I was an ass natural, and she said she couldn't wait to go out to parties and get fucked together.

I climbed the stairs with a wave to Rebecca. That day I wore my best slut gear, and Willa had helped with my makeup. I had a sharp, smoky look with a tight lycra crop top, a latex skirt that rode up to show off my plug and my cage if I stepped too fast, and six inch booted heels. And fishnets, of course, how else would guys know I was a bona-fide slut?

I made it the top of the stairs and saw Master standing there in his office, already naked and his cock erect and waiting.

"Now, before we begin," he said, holding up a hand, "there's something you need to know. You've done what you've came to do, isn't that right?"

I cocked my head in confusion.

"When was the last time you had a cigarette?" He asked.

"The day I first came to you," I answered at once.

"And you're healthy now?" He said.

"Oh, yes!" I said happily. I was down over forty pounds, my cardio endurance was much much better, the pole classes had strengthened my core.

"And your social life?" He asked.

"Oh, my God, living with Willa is a blast. And I've loved getting to know the other girls at the gym, Marcia and Dylan and Cherish, and and all the rest. And the guys too, I've even got Henry to start coming!"

He nodded. "So, then, to be clear," he shook his massive cock, and it hardened a bit more. "You've accomplished all you set out to do. If you come here, hand your ass to me and submit as my little sissy slut, that's all you."

I shook my head. He was right; I didn't need to do it. I didn't need to...

But I wanted to. Oh, I knew it would hurt and I'd waddle down those stairs, but I wanted that cock in me more than I'd ever thought.

"Please, please, please Master," I begged, carefully lowering myself to my knees. "Please give this slut your cock. Please fill my tight ass and fuck me, fuck me like a rag doll, fuck me like a wet hole for your pleasure. I'm a whore for you sir, I'm a cumrag, I'm whatever you need this pathetic sissy to be."

That seemed to satisfy him. It certainly stirred his cock, and for the first time as it swung back and forth I didn't feel a warm sleepy trance overcome me.

If anything, it just drove me wilder with lust, my cage agonizingly tight and my butt unconsciously clenching around my plug. Around the plug that marked me as his.

"Then come over here," he said, voice low. "And worship this cock properly. Maybe after that I'll fill your slutty ass."

I launched myself at his crotch, and began slobbering on his meat. I kissed and licked and sucked, I massaged both testicles with my lips, I got his entire, girthy nine inches down my throat and held it there, nose buried in his musty pubes and tongue madly lashing his shaft.

"Fuuuuuuck, I knew you'd be a natural cocksucker the second you walked into my office," he groaned as I swallowed around his shaft. "The smokers always have such a great craving to fill. Now present that ass."

I didn't need to be told twice, turning around and pulling up my black latex skirt so he could see my plug. He chuckled, popped it out and I heard a schlorp as he squirted a load of lube onto his cock.

"I am going to ruin you. Slut," he said. "I am going to fuck your asshole inside out. When I'm done you're going to be broken in body and in mind, waddling out of here with my cum dripping down your legs like the shameless whore you are. Your body will recover and you'll make that hole tight for me, but your mind will never forget my cock."

"Please," I gasped breathlessly, "please Master. Destroy me. Shatter me. Enslave me to your cock, fuck everything out of me but the desire to serve you, to worship you."

"Here it comes bitch," Master said, and he eased his cockhead into me.

For all his taunting, he did go slow at first. I was beyond thankful for that, as I was for every single second of anal training Willa had demanded do. It pushed me to the limit and beyond, and after the first time his shaft scraped my sissy button, the P spot, I stopped trying to make sense. I just moaned and gasped and yelled in equal measure, and when he began to fuck me for real it just became a single shriek.

For all the avalanche of sensation buried me, I was just present enough to feel him bury his cock to the hilt in my ass and throb as he shot his load into me. It seemed to go on for a long long time.

Eventually, I was aware of the empty feeling as his cock was pulled out of me. I whined and clenched my muscle against it, but he laughed and slapped my ass. "Hungry sissy are we?" He said. Once it was out I turned on shaky legs, almost fell as I tried to kneel, compromised on sitting on one leg, and slowly licked his cock clean.

"Aren't you glad Willa showed you how to really clean that ass out, huh?" He said, one hand gently guiding my head up and down his half hard cock.

"Yes Master," I said.

Once he was sure I'd tongued every inch of his cock and his balls, Master grabbed me and pulled me to my feet.

"Now, sissy, things are about to change," he said seriously. "Rebecca will explain some of it. Willa will explain the rest. You're about to embark on a whorish journey, a quest of sex and kink that will shock even you. But always remember, you belong to Master."

"I belong to Master," I nodded.

"Good sissy," he said, and then he slapped my ass. "Now, go on."

I made my way down the stairs with difficulty and the help of the railing. I still had some trouble with the six inch boots, and the rough fucking had left me weak and sore. At least I wasn't literally leaking cum, as Master had reinserted my plug.

Rebecca waited at the bottom of the stairs. "Are you ready to pay now, sissy?" She asked.

I blinked at her in confusion.

She laughed, a little unkindly. "Your sessions! I told you that you would pay for them once you were done. You're done! You surrendered yourself, Master Anderson has marked you and bred your ass, and now you pay."

I blinked again. "With money?" I asked, knowing that wasn't the answer.

Rebecca shook her head in the manner of a teacher with a very stupid pupil. "No. It's quite simple sissy. First, you will attend an appointment with a particular friend of ours, who does tattoos and piercings. You'll spend a few weeks between healing and going back for more ink, until I'm satisfied with your look. We own a few clubs in the city, and then you'll start working there. Not the lesbian club, for obvious reasons, and you don't really have the bodytype for the changes we'd need to truly bimbofy you. But our 'alternative' club always needs willing sissy sluts. I think I'll even be very nice and send your friend Willa off too. We like to have new faces in the gym and Dylan has been performing admirably as a receptionist."

I could only nod. "And your favor?" I said.

She laughed again, this time with actual mirth, her black braids thrown back and her charms clacking. "Oh you poor stupid sissy! I've been taking my favor ever since you came on the altar. Let's see the progress."