The Lady of the House Pt. 02

I opened the top drawer of the dresser, and pulled out a set of powder blue pajamas. On top was a pair of white cotton panties with a little powder blue bow--I assumed I was to put these on as well. I changed out of my new clothes and started with the panties, tucking my cock inside. Then, I unbuttoned the collared pajama shirt, buttoning up the large powder blue buttons. Finally, I slipped on the pajama bottoms and tied the little ribbon at the waist in a neat bow--I wasn't planning on messing up any part of my appearance again.

I checked myself out in the mirror, making sure there were no mistakes. My nipples were quite visible through the soft, sheer fabric of the pajama shirt.

Then, barefoot, I padded down the carpeted hall to Miss Orwell's bedroom. I was filled with trepidation as I raised my fist to knock on the door--what was she going to do to me in there? But she had ordered me to come to her bedroom, and as her servant I must obey. I knocked lightly.

"Come in, darling."

I opened the door, and to my surprise I saw my Mistress reclining on the king sized bed, fully nude aside from a garter belt and thigh highs. Her breasts were full, her hips were wide and round, and her vagina was shaved. I averted my eyes shyly. I hadn't had sex in four years, before my transition, so this was a lot for me.

"Look at me, Kaitlin," she ordered. I met her intense gaze. "I want you to lay on the bed where I'm sitting, face up." She moved to the side, and I did as I was told. Miss Orwell bent over me, untying my bun and letting my hair splay out on the bed. Then, she straddled me, reaching down to play with my boobs through my pajamas as she sat down on my crotch. It felt good, and I was soon hard again. My penis pressed against her vagina through two thin layers of fabric. She began rocking her hips back and forth, her vagina rubbing along my shaft. I stifled a moan.

"It feels good, doesn't it Katie. This is your reward for taking your punishment so well. If you can manage to be an obedient servant then you're going to feel like this every night." She leaned down and kissed me, our lips interlocking. I moaned into her mouth. She pulled away and said, "You must ask permission before you cum. I will give you your orgasm when I see fit."

"Yes Miss," I said breathlessly. Her grinding had never abated, and now she pulled her hips forward slightly, grinding her clit against the head of my penis. I moaned, putting my hands up above my head. She pinned my wrists to the bed, grinding hard. This was almost too much for me. She was completely in control, I couldn't move if I wanted to. "Mistress, may I--" I started to ask, but I was cut off by my own moan. The tip of my cock exploded with pleasure, and I felt myself soak my pajamas and panties with clear warm cum.

When I came to my senses, I said "Miss Orwell, I am so sorry, I tried to keep it in. Please don't punish me." But there was a part of me that wanted to be punished. After all, I had disobeyed.

"Don't beg," she said sternly. "Flip over."

I did as I was told. She put a pillow under my hips so my butt was sticking up in the air, and she pulled down my panties and pajama bottoms, just enough to expose my butt. Then, she brought a hand down hard against my left cheek, stinging me with pain. I cried out.

"I shouldn't have to remind you to count, Kaitlin," said Miss Orwell.

"One," I said weakly.

"That's a good girl." She brought her hand down again, with the same force as last time.

"Two."

We continued like this until she reached fifteen. My butt was sore and red by the time she finished, and I lay slumped down, my cheek buried in the bed.

"Fifteen's a lot, isn't it sweetheart?"

"Yes Miss, it is," I said quietly.

She pet my tender cheeks with the hand she had just spanked me with. "Hopefully that will teach you to control yourself." She paused. "I want to do a little exercise with you so you can practice self control. Pull your pajamas up and put that pillow between your legs--just like that, good girl. I want you to hump the pillow for me. Ask permission when you're about to cum."

A bit embarrassed, I began grinding into the pillow. It felt good. I continued like this for some time, my pleasure building. Then, Miss Orwell put her hand under the pillow and applied upward pressure. My thrusts were grinding into her hand through the pillow. It didn't take long in this arrangement for me to get close to orgasm. "May I please cum, Miss?" I asked at last?

"Not yet, darling." I stopped humping so as not to cum without meaning to. "I didn't say to stop, now did I love? Keep going."

"Yes Miss." I continued humping, and I felt my orgasm building once again, but I gritted my teeth. I knew it probably wouldn't do to ask again right away. After a few more moments of struggling to keep myself contained, I asked "Miss Orwell, may I?"

"Not quite yet, Katie. Soon."

But as she said it I lost control, coming hard into the pillow, moaning loudly.

"Better," said Miss Orwell, "But still not good enough." She removed her hand from beneath the pillow and pet my back with it, up under my pajama shirt. "I think you need a punishment that will remind you to control yourself. Tomorrow morning I want you to wear a set of nipple clamps under your clothes. You may take them off when I say so."

"Yes, Mistress," I said, resigned to my punishment.

She got up off the bed and rummaged around in her nightstand before drawing out a silver chain with rubber covered clips at the ends. "Take this from me, lovely." I sat up and took it. The metal was cool on my hands. "I want you to go back to your room and change into a fresh pair of pajamas. The rest of your night is free time, you may do what you like, provided you stay in your room. In the morning you will get ready according to the instructions I left for you in the bathroom. I want you up at 6:30 sharp to get ready. You will meet me at 8:00 in the dining room for breakfast. Do not be late. Understood?"

"Yes, Miss Orwell."

I padded back down the hall, my pajamas still soaked with my wetness, and returned to my room. I changed into a fresh set of pajamas after cleaning myself off with a washcloth, and I climbed into bed. Within moments I was asleep.