[TG] Lady of the Hour

Commissioned by George Washington

A man goes to sleep one night only to wake up in an entirely new reality where he is a woman of nobility and men don’t seem to exist. 

~

Chapter 1

The veil of sleep slowly lifted and immediately I realised something was wrong. I was far too comfortable. I rolled onto my side and listened for the telltale creek of the rusty spring that always woke me up in the night but instead there was nothing but silence and plush comfort. The cheap sheets I’d gotten from Walmart were like satin against my skin and no longer smelt of artificial lemons. It was nice really, a comfortable dream maybe. I snuggled in deeper, trying to savour the experience a bit before I woke properly but then a blinking light flashed beyond my lids and all remnants of sleep were washed away in an instant. 

“Morning, Milady.”

I blinked rapidly to clear my vision and saw a huge mattress with satin sheets and velvet blanks stretching out before me. There was a woman shuffling around the giant bed wearing an apron and opening the grand windows to let in the morning light. 

“...Huh?”

“I’ll give you time to wake and then be back with your breakfast.” She smiled before giving me a curtsey and disappearing out the grand looking white double doors. 

The closed with a quiet click and I was left alone, looking around a room that looked like something right out of Downtown Abbey. Considering I’d gone to sleep in my Manhattan apartment; complete with shitty pipes and sirens are a constant companion I was a little confused to put it mildly. Was this a dream? I reached down and pinched my arm.

“Ow! Okay, nope, not a dream-hey what are those??”

I’d gone to sleep in my boxers but I wasn't wearing them anymore. Instead, I seemed to be wearing some sort of satin nightgown with little puffy sleeves laced with ribbon that showed off my clavicle. If the fact that it was a dress didn't give it away, the cut made it obvious. This was a woman’s outfit and yet it was perfectly tailored to my male frame. 

Feeling completely befuddled I stood up and felt the soft carpet beneath my feet. Outside the windows was an immaculate looking garden, complete with fountains, rose bushes and…was that a hedge maze? 

“This has to be a prank, is this some new reality show?” I called out to the walls. “Hello? You got me, very funny. Can I have some pants now?”

Silence. 

“Okay then.”

I shrugged; this had to be some sort of prank so my best option was to just go along with it and preserve as much of my dignity as possible. I opened the gilded wardrobe and was met with a forest of frills, skirts and all manner of weird items I couldn’t begin to understand how to wear. I picked up a corset between my thumb and forefinger and sneered; it looked like something from Renfaire, no woman would need that much support surely…

It took some time but the most masculine clothing I could find was a pair of jodhpurs and women’s riding boots, along with a white blouse and vest. The latter two had far too much room in the chest but somehow, when I put them on, they seemed to fit perfectly. 

Once I was dressed, I peeked out the bedroom door and found more vaulting ceilings and expensive looking furniture in the hallway. One end of the hall was a dead end, the other seemed to lead to several more rooms and a curving staircase. I walked along toward the staircase and gazed at the magnificent paintings on display in the hall. They looked like something out of a film; all austere and classical. 

Then, I saw one that made me stop dead; it was me, standing in the most glorious ballgown I had ever seen. All bright blue with an open front to show off my non-existent cleavage and a huge hoop skirt. I had the same serious, half smile on my face that the other woman sitting next to be did. She was dressed much the same, with her blonde hair all styled up on top of her head and an emerald necklace resting just above her own ample bosom. 

“Milady!”

I saw the same woman from before holding a tray in her arms.

“Did you intend to go riding today?” She asked with a cocked head. “Surely you will want your breakfast first.”

“I’m fine, who is this?” I asked, pointing to the woman from the painting.

The maid blushed, looking embarrassed and shuffled slightly.

“Your wife, milady. I know I am new but I swear I know the household well enough. Nobody informed me of the change in your schedule.”

She thought I was…mocking her? 

“No, it’s not-never mind. Where is my wife now?”

“She is in the dining room, waiting for the car to come around so that she can visit Lady Sybill. Did you wish to go with her?”

“Uh maybe?”

I had no idea what I was supposed to do in this situation. The idea that this was some sort of prank show was starting to seem less plausible. Everything here seemed too real. 

“Come, I shall take your tray to her and you may eat together.”

I nodded and followed the maid down the stairs, taking in all the details of the huge mansion I found myself in. It all seemed so fantastical, yet modern at the same time. I spotted a phone by the wall and another servant rushed past us with what looked like a steam powered vacuum. When we reached the dining room the doors opened to reveal a large television that took up half the wall. The morning news anchor was discussing the latest innovations in zeppelin flight across the Atlantic; I felt like I had stepped into a fairytale. 

“Darling!”

I turned from the TV to see the woman from the painting, wearing a much less adorned dress this time but no less royal in appearance. She smiled sweetly as the maid put down the tray and curtsied before pouring tea into a gold painted china cup for me and pulling out a chair.

“Oh, if I had known I would have waited to eat my own breakfast.” My wife smiled fondly. “It’s not often you wake up so early. Margaret is usually still trying to coax you out of bed at this time.”

“...Sorry?”

“Oh darling, you know I don’t mind.” 

She patted my hand lovingly. 

“Milady was wanting to join you for tea at Lady Sybils.” The maid, Margaret, said quietly and my wife looked me up and down.

“You’re not really dressed for tea though.” She said, “And we will need to get going soon, you don’t normally like talking about business.”

Business. Okay, so my wife was in charge of whatever made us all this money then. If I was going to figure out what was going on here, I was going to have to learn as much as I could about this world as possible. Without letting on that I had no idea. Everybody seemed to be treating me like I was a normal part of this place and if I let on that I wasn’t…I’d seen enough historical fiction to know a sanatorium visit would probably be in my future and that seemed unpleasant. 

“I want to learn more about it, be involved.” I insisted and my wife beamed.

“Oh, that’s wonderful! You’re such a wallflower all the time. I am sure getting more involved in the process will help you enjoy the night more.”

I nodded as if I knew exactly what she was talking about and filed everything away in my brain bank before taking a sip of the tea. It was rich, milky and delicious; I couldn't help but sigh happily, then blush when I realised my pinkie finger was extended. 

“First things first though.” My wife said, “You need to get changed, Margaret, take my darling up to her room and get her dress in something appropriate for a morning tea. I’ll tell the driver to wait an extra few minutes.”

  “But what about breakfast?” I asked, looking a little forlornly at the plate of toast as my stomach growled.

“Sybil always puts out too much for tea anyway, you can eat there.”

Margaret pulled my chair out and I got to my feet reluctantly and followed her back up to my room where she stood me on a little stand right before a fold out mirror with three panes so I could see myself from multiple angles. 

“The pink or the green, Milady?” Margarette asked, offering me too pale pieces of ribbon.

“The green?” I tried, “Why do you keep calling me that?”

“Milady?”

“Yes.”

Margarette looked uncomfortable.

“...What else would I call you?”

“Sir?”

Margarets face screwed up in confusion.

“I’m sorry, I don't know that word Milady.” She said, looking embarrassed for a moment before hurriedly gathering things from the cupboard and helping me out of the clothes I’d so carefully picked out to try and feel more masculine. 

“You know, it’s like a respectful term to call a man of my…station.”

God that felt weird to say. Not as weird as Maragret’s reply though.

“What’s a man?”

“I am.” I blinked, “You know, there are men and women, Adam and Eve…”

“I’ve never heard of anybody with the name Adam before.” Admitted, “I’m sorry but is a man a position I am unaware of?”

Okay, this was getting us nowhere.

“Never mind.”

Margaret seemed happy I dropped the subject and went about fussing over my outfit. I felt my face burning with embarrassment as she slipped me into a pale green dress with a fitted bodice and a long flowing skirt. The edges were embroidered with gold and she even made a show of brushing my hair.

“A natural look today perhaps?” She suggested, as she ran the soft brush bristles over my cropped hair. 

As she continued to brush though I couldn't help but notice my hair starting to tug a little more with each pass over. I looked in the mirror and felt my mouth part in surprise; my hair was always short so why was it brushing my chin now? When did that happen? 

“The car is ready and Lady Anna is waiting.” Another servant announced with a quick knock at the door.

“Just in time.” Margaret smiled, “Come Milady, you know how short Lady Sybil gets when people aren’t on time.”

“Oh yes.” I lied smoothly.

I felt so strange, walking through the glorious house in a dress of all things. I could feel the soft fabric brushing against my ankles and the morning breeze moving between my legs. I felt so…exposed. I couldn’t deny the outfit was comfortable though. It felt oddly freeing walking around in it. 

I walked out the huge front doors to be greeted with a sweeping stone staircase, at the base of which was a limo, complete with a doorwoman waiting for us. 

“Hurry, darling!” Called my wife, who I assume had to be Lady Anne.

Thank God somebody mentioned her name so I didn’t have to ask. I slipped into the limousine feeling out of place amongst all the expensive leather and tinted windows. There was even a champagne bucket with fresh ice; but Anna didn’t reach for it so neither did I. I had no idea what the social norms were here and I didn't want to risk doing anything to tip my new wife off. 

“I’m so glad you’re coming with me; I love you darling but you do need to get out more.” 

“You’re right, just be patient with me?” I asked and without warning Anna leaned over and placed a delicate kiss against my lips.

I stiffened out of shock and she pulled back with her brow furrowed.

“What’s wrong darling?”

What’s wrong? What was wrong was a guy like me being with anybody as beautiful as her. Anna looked like a princess from a fairytale, albeit with a more ample chest. A woman like her would never give me a second glance, yet here she was, almost in my lap with her lips shining from our kiss. What the hell; why not enjoy myself a little.

I reached up and gently cupped her face, still amazed when she leaned into the touch rather than away, then pulled her in close. I could feel that large chest crushing against my own, the fullness of her lips pressing against my teeth. Arousal swam within me and yet, I didn't get hard. It was probably a good thing and after all the other weird stuff this morning that was the least of it. 

“Sorry, I was still just waking up.” I said as I pulled back, Anna smiled at me coyly.

“When we get home from morning tea perhaps, we could take things further…”

The driver cleared her throat.

“We’re here Miladies.”

Anna gave me a flirtatious laugh before hopping out the car door before the doorwoman could even reach it. I chuckled, watching her fluster and bow to me several times as if that would make up for her ‘mistake’. A serving woman greeted us both and escorted us up into a lavish house then through it to the most overly perfumed rose garden I had ever seen. 

“There you are! I was wondering if I’d been stood up!”

A red-haired woman with fiery eyes was sitting at a table, plates with sandwiches, pastries and cakes sat before her and my stomach rumbled. 

“Sorry, my darling decided to come with me today to talk business!” Anna smiled and I did my best to return the gesture.

It felt so weird plieing my legs and holding the edge of a skirt. I don’t think I’d ever bowed before in my life let alone done a curtsy. I smiled at Anna but in my mind, I couldn’t stop feeling slightly irritated at her constant pet names. It felt lovely having a hot woman doting on me but I really needed to know my name! Something told me it wasn't Henry anymore. 

“Lovely to see you as always, Sybil.” I greeted and took my seat. “May I try one of these?”

Sybil nodded and I helped myself to the food, doing my best not to moan with delight. The little treats were the best tasting things I’d ever eaten! Certainly, better than dollar store pasta and sauce from a tin. 

All around us servants poured tea and offered us further treats, one even bought us a parasol as the morning sun began to rise. I’d never experienced such luxury; I didn't even care that I was in a dress!

“Right, we should get down to business.” Symbol said after a few minutes of pleasantries. 

Yes! Finally!

“Do we want gardenias or tulips as the centrepieces? Which do you think sells the mood more?”

…what?

“Gardenias, oh and then we can get those little edible flowers to go on the cakes in a similar shape! It’s a little twee but I think it’s exactly the sort of little touches that make the opening balls special.”

“Oh, I agree.” Sybil took a sip of her tea. “The season's first ball is the most important one after all, it sets the tone for the entire season itself. For it to be a flop is such an ill omen.”

“What are you two talking about, I thought we were going to discuss business?” I blurted out.

The two women stared at me then burst into giggles.

“Oh darling, you’re so funny.” Anna smiled. “This is business, the spring ball is the season starter, it has to be taken seriously. Everything must be perfect, right down to the tiniest detail”

The utter insanity of my situation seemed to crash down on me as Anna and Sybil continued to chat about flowers and table arrangements. I’d gone to sleep a middle manager in a crappy apartment and now I was wearing a tea dress and planning a ball while sitting in a damn rose garden. How had my life gotten so completely turned upside down? 

“Are you alright?” Anna asked me, breaking me out of my reverie. “You wanted to join us but you haven’t joined the discussion at all.”

“Oh uh…”

I didn't know jack about planning a party, let alone a fancy party like this.

“Cucumber sandwiches?” I tried meekly, that was something people had at those fancy high tea cafes downtown sometimes hosted right? Not that I’d ever been to one. 

Anna gave me a smile but her eyes were filled with pity, like I was a child who’d said something obviously stupid. 

“Cucumber sandwiches are more a summer treat, darling.” She said, patting my arm gently. 

“I’m sure that was fine for your little minor house soirees but we do try to keep our theming a little more on point at the top.” Sybil said sweetly.

I grit my teeth; screw whatever relationship we were supposed to have, I decided then and there I didn't like this bitch. If I was going to have to deal with being in her presence, I was going to make sure to enjoy as many little cakes as I could on her dime.