Katie’s first orgasm had come quickly and was followed by a second within minutes. Her third orgasm took me nearly ten minutes of licking and sucking to bring her off. When she came the third time she pulled my face hard against her crotch and partially enveloped my head between her thighs which squeezed tightly. Her legs were shaking when she let me go and pushed me away from her. She leaned backward on the vanity.

“Damn, girl,” she said. “You weren’t lying about eating pussy! I haven’t come that hard in a long time. Mmm, I can see this becoming our regular thing, Stacey.”

“Katie, I don’t think —.“

“Stop,” she interrupted me. “You got that right, you don’t think. You’re a sissy. Sissies do what they’re told.” She took a few more pictures with her phone. I wondered how disheveled I must look after fifteen minutes between her thighs. “And these pictures will ensure just that — that you do what you’re told.”

“Look, if it’s money you want —,” I said. She stopped me again.

“Stacey, girl, you’ve seen and tasted my pussy. If I want money I can get money anytime I want. I need you to be quiet while I think about this. Here.”

She picked up my new dildo again, this time rubbing it against her wet slit a few times before inserting it into her pussy. She pulled it from her sex, still dripping with her juices. She leaned forward and presented it at my mouth. Wordlessly, I opened my mouth as she shoved it inside.

“You practice with that for a while, I mean since you were going to use it for that anyway. Show me what you got, Stacey. Let’s see those cock sucking skills.” She let go of the dildo and I grabbed it and continued pushing it between my lips. She idly stroked her clit as she watched me.

I did everything with the dildo that I liked done to my cock. I slurped and slathered my tongue up and down the shaft. I took it into my mouth until I gagged on it. I fucked my mouth with it, the familiar gluck-gluck sounds noisy in the quiet bathroom. I heard the shutter sounds as she took more pictures.

After ten minutes of working the dildo with my mouth, she broke the silence.

“Okay, I can’t get any thinking done here. I could stay here all night and rub my pussy while you suck that rubber dick.” She tugged her panties back in place and shimmied back into her jeans. “I got too much work left to do.” She shoved her phone into her back pocket and walked for the door.

“Katie, wait —.”

“That’s Miss Katie while we’re in here, sissy,” she said.

“Miss Katie, you still have the keys to my cage,” I said as I looked at her imploringly.

“So glad you noticed. Meet me here tomorrow right after work. Wear something suitably slutty; I want to see the whole package — everything you got. Heels, makeup, wig, whatever — I want to see your whole sissy self.” She walked through the door but stuck her head back in before letting it close.

“Oh, and don’t forget to practice with your dildo when you get home.”

I stayed there on my knees for a few minutes digesting what had just happened. I crawled to the vanity and held on to it as I pulled myself up. I washed the dildo in the sink and boxed it up. I started to strip out of my lingerie but then thought better of it. Who was I disrobing for? My wife was away and the building was empty. I pulled my mundane clothes on over my chemise, panties, and stockings. As I pulled my suit coat on and checked myself in the mirror I knew it would take a very trained eye to spy anything amiss. All the hallway cameras would see was a man leaving the men’s room.

I felt my cock leaking in my panties all the way home, and I was so horny when I got home. No matter how horny I was, however, I wouldn’t be able to masturbate like I otherwise would have. My mind was still numb from the thought that another person now knew I was a cross-dressing sissy and that same person held the keys to my chastity cage.

I spent the evening with my new toy and stayed dressed in the pink lingerie. I discarded the panties as they were soaked anyway. I picked up my five-inch penis-shaped buttplug and filled my sissy ass with it.

I practiced sucking all of my dildos. I deep-throated the ones I could and gagged myself repeatedly on the ones I could not. I pulled the plug from my ass and used several of my smaller dildos on myself, sticking them to the shower wall and slamming myself back onto them, using them all from smallest to largest. Finally, after breaking my hole in with the other dildos, I lubed up my new black dildo and lined my hole up against it.

It stretched me with its two-inch width as it penetrated me. I felt absolutely violated as I pushed it deeper inside of me. When I felt the balls of the dildo pressed against mine I gasped, realizing that I had it as deep in my ass as it could go. I rotated my hips, enjoying the sensation of it moving inside of me. I reached for my cock to stroke it and then remembered that I was still locked in chastity.

It was so easy to forget that I was locked up while there was a cock in my ass!

After cleaning myself up I dug through my things and laid out all of my lingerie, heels, anal toys, and the few sets of clothes I had. I quickly selected a pair of black patent five-inch heels with an ankle strap. I put my pair of breast forms with the shoes and then picked through the lingerie.

I selected a set of burgundy lingerie — a lacy half-cup satin bra with the cups covered with two lines of lace leaving them “open” for fun. A burgundy satin ribbon was nestled between the cups. The back of the bra was sexy as well, with the band made of the same black lace along with a second set of lace that crossed the back at the shoulder blades. The panties had a panel of satin in the front, trimmed with a smaller bow where the lace sides met. The lace sides wrapped to a lace back that was split completely open with another small burgundy bow at the center of the waistband. These panties — worn by a woman — would have provided easy access to both of her holes, but worn by a sissy would allow access to her ass while keeping the clittie tucked away in the front.

I picked a completely sheer white long-sleeved blouse and paired it with an A-line pleated mini skirt that looked schoolgirl-ish. It was plaid with a pink and gray tartan pattern and only just reached below my ass cheeks. I added a pair of black Cuban heel seamed stockings to the pile and then added my makeup bag. I did not yet have a wig, though I had been meaning to get one someday.

I went to bed in the same pink lingerie. I barely slept — I seldom wore my cage this long and I kept waking up to feel it before drifting back off to sleep. In the shower the next morning my stomach was doing flip-flops. I knew I could muddle through the workday with few problems, but I was really worried about what the evening would bring.

I dressed like normal, choosing a black suit so that any leakage from the cage would be less noticeable. As expected the day of work just flew by. As I watched the clock tick past 3:30 I began to feel queasy. Katie came in, as usual, making her rounds. When she got to my office I wondered what, if anything, she might say about yesterday.

“Hey, how’s it going?” she said, her usually chatty self.

“Umm, great,” I said. “You?”

“Couldn’t be better,” she said brightly. As she bent over to empty my trash I saw one key to my cage on a chain around her neck. I immediately wondered where the other key might be. She noticed me noticing.

“Like my new necklace?” she asked. She twisted the narrow tip of the key between her thumb and forefinger with a mischievous glint in her eye. I shifted uncomfortably in my seat and I felt my cock swelling in my cage.

“Very interesting,” I replied.

“So, any big plans for this evening?” she asked. “Anything fun on the horizon?” I felt my face flushing a bit.

“Probably just staying in, you know. Old boring married guy.”

“Oh, I understand,” she said. I saw a flash of green as she quickly pulled something from her front pocket and dropped it in my lap. She lowered her voice. “You left me with some nasty thoughts last night. I had to stop working for a little Jilling. Made quite the mess of these.”

“Catch ya later,” she said aloud as she left my office to continue her work.

I knew without looking that it was her satin panties from last night; I could still smell her sex on them. I quickly held them up to my nose and inhaled, reveling in her womanly scent and reliving last night. I stashed them in my bag.

The thought of what Katie might ask me to do tonight both thrilled and terrified me. At 4:45 I excused myself and told everyone I was ducking into the bathroom before it was time to leave. I wanted to give myself enough time to be ready for her. I did not know what time she would arrive or what her plans were, but as long as she held the keys to my cage I did not want to disappoint her. I made sure the door was locked this time!

I started with the panties since they were crotchless. I pushed my caged cock out the front and checked my ass in the mirror, making sure they were situated to best display my assets. I was already leaking pre-cum, so as I continued getting dressed I periodically wiped the tip of my cage with my index finger and licked the juice from it.

The stockings came next. Although I had been dressing for more than a decade, I still thrilled at the way stockings tugged at my garters when I wore them — it made me feel so damn sexy! I checked my seams and made sure they were straight as well. I placed my arms through the bra straps and fastened them behind me before reaching behind my neck to fasten the cross-shoulder lace strap.

I inserted my breast forms into the bra’s half-cups and adjusted the lace openings to display the nipples and areola properly. I checked myself in the mirror, liking what I saw so far. I quickly spread some foundation and applied concealer. My eye makeup was next — eyeliner, a blush pink eye shadow, and mascara. I applied some blush and then did my lip liner. I checked my phone for the time. It was just a few minutes after five.

I pulled the blouse on, and struggled just a little with the backward buttons, getting the job done. Then I stepped into my skirt and zipped it up, checking the mirror again to be sure it settled on my hips just so. My heels were last. I stepped into the shoes and knelt to secure the ankle straps. I normally didn’t do a lot of walking in my heels, but the sounds they made on the tile floor made me stand almost completely still.

I checked my phone again, 5:15. It was time for the final piece. She wanted to see my “whole sissy self” and I was going to give it to her! I pulled my medium metal jeweled buttplug from my bag. I lubed it with a small amount of liquid soap, rubbed it around my sensitive asshole, and then shoved it home; relishing the semi-full feeling it provided. The jewel in the plug was pink, of course.

I reviewed myself in the mirror. The dark burgundy and black lace of the bra showed clearly through the sheer blouse. The skirt was pink, the cage was pink, and the buttplug was pink. The panties were open-crotch with attached garters and stockings, and I stood in black patent five-inch heels strapped to my ankles. If THIS didn’t say “complete sissy” I didn’t know what would!

I minced over to the door, listening to be sure my coworkers had all left the building. I opened the door, unlocking it as I did so. I peeked out, happy to see all the lights off. That meant that there shouldn’t be anyone left on the floor. I listened intently and did not hear any signs of habitation. Then I heard the elevator ding. I heard Katie’s cleaning cart rolling down the hallway and ducked back inside, leaving the door unlocked.

I briefly pondered how she might like to find me. I thought about our interaction that afternoon and made a snap decision. I knelt on the floor, sitting back on my calves like I had last night — my “pussy-eating” position. I pulled her green satin panties from my bag and held them up to my nose again. The smell of her pussy in them was intoxicating! There was a light knocking on the door.

“Stacey?” she inquired. “You in there?”

“Yes, Miss Katie,” I said obediently. The door opened.