Cherry Ch. 05: Starting my New Life

During the subsequent days, Sir set me up with a routine. Awake at 6:00 am, ass lifting workouts until 6:30 am, the spin machine until 7:00 am, shower and ready by 8:00 am, and breakfast for Sir by 9:00 am. The rest of the day was more variable. Depending on Sir's work schedule, I could be dusting his expensive furniture, servicing his cock while he emailed clients, or assuming some humiliating position to entertain him.

By the second week, my body underwent noticeable changes. My skin seemed smoother, my waist seemed thinner, and my weight (or what little I carried) began to distribute toward my ass and hips. I already had a soft jawline with wide eyes, so feminizing my face was not difficult. I was certainly "passing" by the second week.

After a session of bobbing up and down on Sir's cock during a video conference with clients, Sir reached under his desk and stroked his thumb across my lower lip. "Your cosmetic skills are certainly improving." A warm glow filled my chest and the praise. "But that just makes those lips look fuller, these blowjobs will feel much better when we pump those up."

My breath hastened as a cocktail of emotions replaced the warm gratitude at the praise. From my cognitive reconditioning, I felt anxiety about being any less than a perfect fuck toy for Sir. I felt further angst at Sir's use of the word, "when." I had always been a coward about medical procedures. For example, I've been a blood donor since I was old enough to donate, but I nearly cry every time they brandish the needle.

I tried to ask Sir when he planned to augment my lips, but my conditioning prevented the words from leaving my mouth. Seeing my cum-coated face on his lap vainly attempting to move my lips, Sir laughed, "you may speak."

"Sir, when will I be getting my lips filled? And how big will you make them?"

THWACK. Sir slapped me across the face. "That's a bad girl. You never address Sir in the second person with 'you.'"

I began hyperventilating as dread, guilt, and shame welled up inside of me. Sir patted me on the head, "it's okay now, just do better next time." I sighed in relief. "Now try again."

"Sir, when will I be getting my lips filled? And how big will Sir make them?"

Sir completely ignored my question. "That wasn't a very sexy way to ask." Sir stared into space for a moment, contemplative. "I know what'll make it better. My first girlfriend had a lisp. And it was profoundly sexy. For the rest of the day, you'll be speaking with a lisp. You can pronounce your 'S's properly again tomorrow. Try again."

"Thir, when will I be getting my lipth filled? And how big will Thir make them?"

"Oooh that's much better. But try again with a higher voice. And smile for me when you're talking, it will add a more singsong flavor."

Compliantly, I grinned like an idiot and raised my inner eyebrows submissively. "Thir, when will I be getting my lipth filled? And how big will Thir make them?"

Sir looked away for a moment longer. "I feel like it could still be better. Something about you referring to yourself in the first person is turning me off. Try again, but you're not to address yourself in the first person. In case you're too stupid to know what I mean by that, no more "I," "my," or "me." And you shouldn't be using possessive articles when referring to yourself anyway. Those aren't your lips. Those lips, every other part of that little body, are mine. You can say things like, 'please cum in this mouth,' or 'fuck this fat ass,' but you're not to refer to them as your lips, your mouth, or your ass."

"Yeth, Thir."

"Good. Now try again."

"Thir, when will Thir be filling thethe lipth?" I was disgusted by my own singsong, childlike voice. "And how big will Thir make them?"

Sir was pleased. "Much better. I am the subject, you are the object. Never forget that." Sir patted the side of my face, but didn't bother answering my question. I gushed, my smile growing to show all of my teeth, my shoulders coming together and up, my inner eyebrows raised as I looked up at Sir in warm gratitude for the praise.

But at a deeper level, I hated that his praise invoked this feeling in me. I hated what he turned me into. I hated what I had become. I hated myself for ever agreeing to meet with him. And I hated him.

Several more days passed in this new routine. On one particular day, Sir had me dusting the extravagant furniture in his home. My "uniform" for this task was a French-maid-style lingerie set. White ruffled fabric pushed out my black skirt, barely covering my developing ass cheeks. My 4-inch black heels clicked as I walked along the dark wood flooring. My midriff was exposed up to my chest, which was adorned with a sheer, white top. What little chest muscles I started with had shriveled down, exposing my ribs. I could much more easily pass for a flat-chested girl than a male.

I heard the familiar thump of Sir's footsteps approaching me. I often fantasized about running away from those footsteps. But some explicit commands early in my training vanquished any such thoughts. "You are never to leave the house unless I accompany you and you have my stated permission to do so," I remembered Sir instructing, "you are never to think about leaving the property without me and without my stated permission to do so. You are never to attempt to escape. You are never to plan any escape. You are never to attempt to circumvent your conditioning. If you ever have thoughts of circumventing your conditioning, you will stop thinking those thoughts and report what you thought to me. When I approach you, you are to stop what you're doing, face me, get on your knees and put your palms on the ground in front of you."

My mind snapped back to the present as Sir entered the room I was presently dusting. I immediately dropped to my knees, faced sir, and put my palms on the ground, holding the feather duster under my palm with my thumb.

Sir tossed a pair of black panties, black yoga pants, and a black, sporty halter top onto the floor in front of me. "Take off the uniform and put it away along with the duster. Put these on and meet me by the front door."

Was Sir taking me somewhere? Was I about to leave? I hadn't been outside of the house in over two weeks. My heart raced in anticipation of seeing the sun and breathing the fresh air again. Sir's house was on the coast of a lake on the edge of the city, so I could occasionally smell the sweet air when I was near an open window.

After I'd put on my outfit, I considered the implications of going outside. Where was Sir taking me? Could he be allowing me to leave? Unlikely. Would I have a chance to run for it?

A sharp pain filled my chest. The familiar guilt and dread filled my thoughts. I had the thought of running away. That was bad. That was terrible. That was unacceptable. Sir had instructed me not to do that. I couldn't disobey Sir. My hands went to the sides of my face as I started hyperventilating.

"What's going on?" Sir noticed what was going on as he approached. My programming kicked in and I spilled the beans. "I'm so sorry, Sir! I thought about running away if you took me outside!" I fell to my knees and placed my palms far out in front of me as if prostrating and begging for forgiveness.

Sir clicked his tongue. "Tsk tsk tsk. That's a bad girl." I could feel the dread creeping into my limbs at his words. "But I'm glad you told me. And I suppose it's to be expected." The dread began to subside. "I'm keeping you here, a prisoner against your will. I've broken your mind. I'm molding your body. I've made you into something less than a slave. I wouldn't be surprised if you hated me as deeply as one could hate another person." I couldn't bring myself to look up at him as he spoke. "I've thought about destroying your ego completely. And I could do that. You've seen what I can do with our 'happy girl' and 'cock worship' commands. I could make that feeling permanent. I could make you the happiest person in the world, prancing around and serving me. But I enjoy your shame. I relish your humiliation. I want there to be something inside of you that wants to resist. I want to break you and make you do anything I want, but I don't want you to consent--or think that you're consenting--to any of it."

Despite myself, I could feel my little member getting hard.

"So, I'm going to leave you in there, Caleb. Every time you suck my cock, every time you bow to me, every time you eat on the floor, every time I fuck you. I want there to be a little Caleb in the back of your mind screaming at you that this is wrong. That you shouldn't be doing this. And I want that Caleb to be helpless to stop any of this."

I could see the fabric on the front of Sir's pants moving as he spoke. "Damn, I'm turning myself on." Master pointed to a small table in the corner. "Go to that table, pull down your yoga pants, and bend over. I'm going to fuck you now. And I'm going to make you cum while I'm fucking you. I'm also going to turn off some of your 'silence' commands, so you're welcome to cry, scream, and beg me to stop while I'm fucking you. But I'm going to keep fucking you until I explode inside that tight little asshole."

"After I've finished, you have an appointment to get those lips filled," Sir continued, "I'm thinking I'll inflate them to something bigger than a teen social media influencer, but not quite as big as a blowup doll. For now. And I hope that Caleb is in there, lamenting that there's nothing he can do about it."

With the silencing commands turned off, tears filled my eyes as I bent over with my stomach on the table. "PLEASE! Please stop this! I'll give you anything you want!"

Sir chuckled as he approached me, unbuckling his belt. "We're well past you giving me 'anything I want.'"

"PLEASE stop! I don't want this! I didn't want any of this!" My voice raised to a shriek.

I felt Sir's hands press into my ass cheeks, spreading them and kneading them with his fingers.

I had given up begging at this point and just lowered my head onto the table, tears covering my face.

"Done begging already?" Sir sounded bemused. "If you're not going to beg me to stop, then you're going to beg me to fuck you. Now beg me to fuck you. And you'll refer to me as 'Daddy' until I say otherwise."

"Oh please, Daddy," I moaned through my wet lips and face, "please fuck this tight hole. PLEASE fuck this tight hole with Daddy's big cock."

Daddy reached his hand toward my face and put his thumb and index finger into my mouth. Instinctively--or more accurately, as 'conditioned'--I sucked on his thumb and finger like my life depended on it. Daddy pulled his hands from my face and circled his now-wet thumb and index finger around my anus. I arched my back and relaxed to let his finger in to rub saliva around my hole. He then reached deeper, circling the inside of my anus with his finger. My breathing deepened as I continued begging like a slut.

Daddy removed his finger, and I felt the big, plushy head of his cock position against my anus. Daddy's hands gripped my fleshy ass cheeks. I knew from experience that I would have red hand prints on my ass for the rest of the day from Daddy's powerful grip. I arched my back, lowered my chest deeper against the table, and exhaled.

**TO BE CONTINUED**