James had insisted that I come over mid-week, so that he could lock me into chastity. I did so, and had been locked in for three days. I’d woken up several times each night with the pain of my dick getting hard in the restraining device. To say that I itched for some playtime and a possible release would be an understatement. He used another CB 6000, like the one Sebastian had worn, but this one he’d bought just for me. Slightly more comfortable for long-term wear than the older models, its style and fit enabled easier cleaning and urinating.
I hadn't seen Sebastian since the past weekend and I missed him. A lot. I told him so and he told me there was no point in getting together when I was under the control of another man, and that it had been my decision to see James this weekend. He didn't seem upset about it but he wouldn't hang out with me until after, because he wanted me to have a clear head when I got to James' place, so that I could figure out what I really wanted, or who. We had arranged for him to stay over Monday night since I planned to be with James from early Saturday to Monday morning.
I had started the cleansing ritual when I heard the door of the bathroom open and realized that my ordeal had begun. I faced away from the bathroom door in my compromising position waiting for the water to fill me properly, and there was nothing to do but continue while James stood and watched. Our eyes met in the mirror as we shared this intimate moment, and I knew he was putting me in my place, showing me that I was his and he could do as he pleased. If he wanted to watch me give myself an enema, he would do it, and it was my job to tolerate it.
He sat down on the vinyl chair and watched me complete the whole process. I think my cheeks were as red as Sebastian’s and my heart was beating frantically with embarrassment and shame. He didn’t lift a finger to help me and I couldn’t decide if that bothered me or if I’d rather he just watched. It was very confusing and profoundly humiliating.
When I’d done I turned on the shower and cleaned up in front of him, deliberately giving him a bit of a show, if only to demonstrate that I still had some power here. Of course, the bored expression on his face when I glanced over a couple of times was enough to convince me that perhaps I was mistaken.
Finally, I shut off the shower and dried off, standing naked before him and awaiting further instructions.
He let me stand there, not saying a word, for a long time. He looked me over slowly, his hands in his pockets like he was watching an accounting presentation, until I really started to wonder what he was doing. Or what he was going to do.
Finally he said, “Get down on your hands and knees.”
I did so.
He stood and walked out of the room, snapping his fingers for me to follow, which I did. So this is how he would play the game. Most men would try to seduce another man by being extremely charming and sweet. Not James. He knew that his best bet would be to treat me like the submissive I craved to be. He would lure me with humiliation and harshness, giving me a glimpse into a way of being that I could enjoy with him much more if we were to get together.
I followed him to the loft on my hands and knees, giving myself over to his wishes and trying to absorb the emotions that coursed through me. I was his until tomorrow to do with as he pleased and I would give myself to that reality, no matter how difficult.
He left me standing in the middle of the loft for what seemed a rather long time. When he came through the door finally I felt my cock swell at the sight. He looked delicious in his jeans and t-shirt. He held something very small and shiny in his hand but I couldn’t see what it was.
“Spread you legs and hold out your arms, please,” he ordered.
I obeyed, wondering what he was up to. He didn’t have any rope or cuffs on him. As he stepped back and looked me over, he showed me what he held in his hand.
“It’s red lipstick, Tate.”
Okay…
“Yes, Sir.”
“No, we’re not going to the ball, Cinderella,.” He chuckled at his joke. I didn’t dare. “I’m going to write on you with it. Words that will show you what you are to me.” He licked his lips, rolling up the lipstick so that the tip emerged, red and glistening in the sunlight that streamed in through the skylight. “Stay perfectly still until I tell you to move.”
“Yes, Sir.” This wouldn’t be so bad. I relaxed somewhat but made sure to remain perfectly positioned as he ran his hand along my back and over my buttocks.
“Hmm, where to start on such an alluring canvas…” he murmured. “How is this feeling right now?” he asked, his hand moving around to cup my enclosed cock, fingers tickling my ballsack.
“Good, Sir.” I gasped as I swelled inside the cage.
“Do you like being at my mercy, young man?” he whispered in my ear, the hairs of his goatee sending shivers through my skin.
“Yes, Sir. I love it.”
“Really?”
“I’m yours, Sir. I’ll do anything you ask.”
“Yes, you will. And I’m going to ask you to do a lot today. Because I don’t think you realize the lengths to which I will go to give you what you crave.”
I felt a wave of desire course through me from my groin to my fingertips at those words. Well, that was what I was here for.
“Thank you, Sir.”
He nodded and then got to work. For the next twenty minutes he applied to my body all the words he wanted me to remember, telling them to me as he wrote: Slut, boy, slave, whore, bad, pig, dog, bitch, cocksucker, pussy. Although what he wrote was intended to degrade me, the sensation of the slippery lipstick on my skin felt sensual and pleasant, and I felt my cock fight its confines over and over as he wrote with delicate strokes on my calf, my forehead, my buttocks, and the sensitive insides of my thighs and elsewhere. It tickled and the strain of holding my arms up began to tell.
“Stay still,” he told me when one of my arms began to lower.
“Yes, Sir.” I moved it back into position, biting my lip from the strain.
He wrote “disobedient” on my chest then and “weak” on my belly. I’m sure I looked a sight.
Finally, he seemed satisfied. He stepped back to admire his work, nodding and smiling. “That’s better. Now you look like you’re ready to serve me.”
“Yes, Sir. Thank you, Sir.”
“You may put your arms down and follow me.”
I lowered my arms with relief, following him over to the wooden armoire. He opened one of the drawers and pulled out a very large stainless steel plug, bigger than the ones he’d used on Sebastian and I previously.
“Hold onto the armoire with one hand and hold your right leg up under the knee.”
I did so, knowing it would take a little while to get that enormous plug into me. It did take awhile, and not a little effort from both James and myself, but finally it was in. My leg trembled from the effort of holding and balancing my weight during the ordeal, and my rectum felt stretched and extremely full. James attached a harness to keep the plug in place and instructed me to lower my leg.
“Excellent. How does that feel?”
“Big, Sir.” I winced. With my legs straight, the feeling of fullness doubled and I wondered if I would be able to walk.
“Good. That will prepare you for me while you work.”
“Yes, Sir.”
“You want to be ready for me when I decide to reward you, don’t you?”
“Yes, Sir. Of course.”
He laughed. “Then follow me.”
He led me from the loft. I followed as best I could, the plug feeling like a goddamn torpedo in me as I waddled behind. I couldn’t help making little noises of discomfort as I walked and James glanced back at me with an indulgent look. “Poor boy. Is it too much?”
I shook my head quickly. “No, Sir. It’s perfect, Sir.” And tried to be quiet.
“Excellent.” He led me to the kitchen and sat down in one of the chairs, picking up the Entertainment section of the Globe and Mail. “Make me some coffee, please. And then a Western omelette. Ingredients are in the fridge.”
“Yes, Sir,” I murmured, turning beet red. Why hadn’t I anticipated this? Of course he would put me to use in the most menial way he could imagine.
I bit my tongue to keep from complaining, remembering that it was my duty to please my Master. If he wanted to have me wait on him hand and foot while caged and plugged and scrawled on, then I would do it.
I made him breakfast and served him, after which he made me clean the kitchen floor on my hands and knees and then wash the dishes by hand.
Afterwards he took me up to his massive bathroom and had me clean it from top to bottom. As I worked I kept glancing at myself in the mirror, seeing the red words on my skin and feeling humiliated and abused. At the same time I thrilled to know that I was pleasing James and accomplishing my tasks with competence and enthusiasm. Because I knew if I pleased him, the quality of the eventual reward would equal the intensity of my debasement. And as he watched me work, I knew that his cock grew hard from the sight of me, plugged and caged at his hand, serving him with all of my being.
When I’d done he inspected my work. I was proud of how well I’d cleaned the room, but had no doubt that he’d find something to allow him to deal out a punishment. My hunch proved correct. Apparently, I’d cleaned the room in the wrong order—he’d gone over it with me and I guess I’d forgotten. He took me to the loft and attached me to the spanking bench.
For longer than I really wanted I suffered under the assault of the wooden paddle, until my ass grew pink and hot and the plug tormented my prostate terribly. I was so horny.
When he finished he let me rest in the spare room, but not before gagging me and tying my hands together behind my back with a length of rough rope.
“That should keep you out of trouble,” he said. “I’ll be in my office. I’ll come get you when I need you.”
I nodded and heard the door shut. I dozed then, drifting in and out through a haze of arousal and fatigue, while my body relaxed and rested. The huge plug in my ass was a reminder of what was to come, and its substantial mass now felt pleasant and comforting. I think I slept, because suddenly I woke to that soothing plug rocking and jostling inside me. I groaned and opened my eyes. The clock said 4:39 pm.
“Wake up, boy. I need you again,” James said, giving the plug a final twist to get my attention.
I grunted against the gag and tried to get up.
“Wait a moment.”
He untied my hands and removed the gag. I stood and followed him to the bathroom, where he came into the shower with me and very gently and meticulously cleaned all of the lipstick off my body. The sight of him so near and wet, his beautiful cock erect and eager, made me wish he’d fuck me or make me suck him or something. When he finished cleaning me of lipstick, he gave me a new washcloth and told me to clean him. I did so slowly and carefully, taking time to enjoy the freedom of being allowed to touch him. He watched me the whole time, and I could see how aroused it made him.
After we dried off he took me to his room, where I watched him dress in a pair of black jeans and a nice black button up, as if he were going out to dinner.
I stood by the bed, awaiting instruction, as he opened another drawer and pulled something out.
“Here, put these on.” He tossed me something pink and lacy.
I held them out to see what they were, my heart dropping into my stomach. I was no cross dresser and he knew that. Again, this was to humiliate and degrade me. With a red face I put on the pink lacy panties over the cock cage and plug harness, adjusting them so that they’d look somewhat decent.
“Mmm, that looks nice,” he said. “Now this.” He handed me a ridiculous short Lycra skirt in a hideous shade of purple that, once I’d pulled it on, felt absurdly tight. The final piece to my embarrassing outfit was a black bustier that he helped me put on. “You’re lucky I didn’t have time to get fishnets and a garter belt.”
“Yes, Sir.”
Thank God.
I already felt like a two-bit whore in this getup.
As a final insult he made me sit in a chair while he applied eyeliner and eye shadow, blusher and lipstick to my face. The entire procedure, although intensely humiliating and strange, completed my transformation from boy to tranny and I couldn’t help but be affected by my Master’s closeness. He obviously got off on this whole thing as the firm bulge in his jeans pressed against me while he worked with concentration and delicacy.
“Ta da,” he said as he finished. “All done. Look in the mirror, Tate. Or should I call you Tatiana?”
“As you wish, Sir,” I murmured, standing and moving in front of the full-length mirror where he directed me.
Jesus Christ.
Who was this person looking back at me? James had turned me into a caricature of myself. It was a vision of a lost and confused boy/man/girl/woman with wide smoky eyes, full red lips, and the ghost of a beard beginning to show. I couldn’t stop staring.
James laughed and clapped his hands like a delighted child. “Wonderful! Now you’re ready for our evening. Come with me.”
He took my hand and led me from the room. He led me down the staircase and, to my horror, walked to the front door and handed me my jacket and my Docs. “Let’s go.”
I stared at him, horrified.
What? Outside?
I wanted to protest but I daren’t. But I couldn’t be seen like this! I stood rooted to the spot, paralyzed by indecision.
“Put on the boots and the jacket, Tatiana, and come with me,” he said firmly, and my knees went weak. Could I do this? I had to, didn’t I? I started to panic, the breaths coming quick and hard. It seemed like I might cry.
Suddenly, his arm went around me and he pulled me tight against him, pressing that firm reminder of his desire against me and speaking softly in my ear. “It’s all right. I’ll look after you.” He stroked my hair and held me close. “Do you trust me?”
I felt my breath calm and a tranquility come over me from his closeness. I did trust him. I could do this. I
would
do this for him.
I nodded.
He stepped back and watched me put on the boots and the jacket. When I was ready he took my hand in his. “Remember, just experience without judgment. And trust me,” he said again.