Inspection

I walked into the room quietly, lifted the hem of my nightie, gave a curtsey. I kept my eyes downcast, horrified to imagine what the co-ed from the local state college must think of me. I heard her uncross and recross her legs, heard nylon rub against nylon. The sound drew my eyes up, to her legs, and I saw her skirt ride up.

"Well this is easily the strangest babysitting job I've ever had," she said, "your wife said your nighttime outfit was irregular but I never imagined this."

"I'm sorry, Miss," I managed to say.

She chuckled. "She said I'd understand why she has a boyfriend," she said, "I didn't know what she meant but I get it now. This really isn't what a girl grows up dreaming about, marrying a sissy."

I blushed deeper, her words stung, accurate as they were. "It...it wasn't always like this," I said, foolishly trying to defend myself.

I saw her shrug. "That's now what your wife said," she retorted. "Well let's get the other part over with so you can get to bed."

"You...you don't have to, Miss," I all but begged, "it...it's not really necessary."

She looked at the list my wife had taken the time to prepare, read from it. "Bedtime. Sissy will be in her room by 8:30 but is permitted to read fashion magazines until 9. Sissy will dress for bed in the panties, peignoir, pantyhose, and heels I set out. She may beg, but she's required to dress in these for bed. Before sending her to her room, please check to make sure her chastity cage is installed and locked. She may beg, but cage inspection is required every evening before bed."

"Miss, I..."

She smirked, stood, removed her sweater, undid her tie. I could see the curve of her breasts through her shirt, immediately felt my penis jump, tighten in the small cage. "No, no, I'm not missing this for anything," she said. "Lift up the hem of your negligee," she said.

I hated myself in the moment, but did it anyways, lifted the hem up, exposed myself, knowing the small, pink chastity cage was easily visible through the sheer pantyhose and my sheer panties.

She laughed. "Sorry," she said, "I...I didn't expect...it's so small."

"Miss, I..."

"You have no room to grow."

"I...it...it's more comfortable this way," I said.

I saw her staring, shake her head. "She let you put that inside her? I mean...she used to?"

"She...when we first started dating," I whispered.

She motioned me towards her. "I'm supposed to make sure it's locked," she said.

There was little question it was locked; my wife was doing this simply to have her tease me. I walked forward, stopped just short of her. She reached for me, touched the front of the cage. "How often does she undo it?" she asked.

"She...she didn't tell you?" I asked.

She shook her head. "No."

I swallowed. "It...she started it two...two years ago..."

"She said that," she said, "my question was how often does she unlock it?"

My voice barely made a sound. "She...n...never," I said.

She laughed. "Never? Seriously?"

I shook my head. "N...no, Miss," I said.

"You can't...she doesn't let you cum?"

"Not like a..." I stopped myself. "I mean..."

"Not like a what?"

"Please, Miss..."

"Not like what?"

"Not...not like a boy," I said.

"Like what then?"

"Like...like a girl," I said, half groaning.

"What?"

"It...nothing."

"What?" she asked again.

"It...when I get excited, it...I try to...to swell and I can't and...and it can hurt."

"Excited? Why would you...oh," she said, realizing she was still holding the cage, that her hand was pressed against me. "Ewwww, what is that?"

I looked down, was horrified to see a wet spot, precum, a fair amount, leaking from the tip of the cage. 

"What. Is. That?"

"I...I leak sometimes," I said.

"That's disgusting," she said, hand still on my swollen balls. "Disgusting." She finally let go, shook her head. "Well off to bed with you then," she said.

I signed a sigh of relief, started to lower the hem of my garment when she spoke loudly, startled me. She looked at the note from my wife, chuckled. "Whatever," she said. She reached for me again, rubbed her finger over my panties, gathered up a glob of precum on her finger, lifted it towards me. "Go on," she said.

Horrified, I opened my mouth, stuck out my tongue, and licked my precum off her finger. "Thank you, Miss," I said as I tasted the salty cum.

"This is the weirdest babysitting gig ever." she said. "Well, off to bed. I understand you have a list of chores for tomorrow?"

"Yes, Miss," I said, dreading dressing in a maid's uniform and cleaning under her watching eye.