Maid to Serve

Hey Everyone -- I haven't written much from my bisexual and crossdressing points of view, but this story includes both of those here. So if that's not your thing, this one might not be for you, just FYI.

Everyone here is over 18 years old, as always. And of course, this is all just fantasy, as it always is. But also like always, let's hope it's filthy fucking hot fantasy.

***

Mr. Andre Bythesea was kind enough to keep me on at his law firm even after I'd failed the bar.

The only catch was that he turned me into his office's free use sissy maid.

It wasn't really supposed to work out like that. It wasn't what I had in mind. He'd hired both Pristina MacCaa and myself straight out of law school, back in May. Our employment, of course, was contingent on passing the bar that summer: if we failed, we could be fired. That wasn't an Andre Bythesea thing, that was an industry thing.

I didn't think anything of it, and, truth be told, I don't think Pristina did either. We'd both planned on passing the test and -- if you had really shot me full of truth serum and made me answer the question -- I would have thought, if one of us was going to fail the thing, it would have been Pristina.

That's not what happened though: come that fall, Pristina was Bythesea & Pusset's newest attorney and I was pretty sure I was out of a job.

"You might be out of work no matter where you go in Acidalia," Mr. Bythesea had told me when he'd pitched his plan to me in mid-September. "A lot of places require bar passage before they'll hire you, and failing once is already a mark against you."

So he'd reached a deal with me. He said he needed more staff around the office anyway -- someone to do the more base-level tasks he didn't want to ask of secretaries. He could pay me for that, keep me on until I could take the test again in February. He told me not to thank him.

It had been Pristina's idea, he said.

Whether or not Pristina came up with the free-use part of the deal and the uniform, I don't actually know. I just know they were required of me.

It's how I came to be making my way past the door to Mr. Bythesea's suite late one October afternoon, hands raw from scrubbing the toilets and floors of the office bathroom, knees aching from kneeling there for too long. It wasn't that it was an especially big bathroom. But you try scrubbing even a single toilet down with a toothbrush -- and getting it actually clean -- and see how long it takes you.

I don't know if the toothbrush thing was Pristina's idea as well, but I have my suspicions.

I was tired, but I knew I still had a few long hours left in the day. The clock on the wall read 5:30 p.m., but I'd fucked up on sending some thank-you emails for Mr. Bythesea's clients earlier in the day. He'd told me he wanted to punish me later tonight, and I knew what that meant.

I'd gotten more than well-acquainted with his belt over the last few weeks.

It being after 5 p.m. meant -- mercifully -- that Mindy, his secretary, was gone from her perpetual post outside his office door. Maybe they'd always been kind of mean to Mindy and she was just glad for someone to punch down at, or maybe she was just mean in general, but I don't ever think I'd heard her speak to me with anything other than mocking derision.

I'd guess the uniform helped with that. Maybe it was easier to make fun of me dressed in a miniscule, pink maid's uniform, the kind with a skirt so short and wide that I couldn't so much as bend over slightly without exposing my ass to whoever happened to be behind me. They had a perfect view of the panties and the garter belt I had to wear, the tops of the stockings as well. Depending on the angle, they might even see the chastity cage I wore at all times as well, the one with the key Mr. Bythesea had taken the day I'd accepted his offer. It made scrubbing the floors on my knees -- a favorite of Mr. Bythesea's assignments -- especially humiliating.

And, if they were so inclined, any random bystander could do whatever they liked to me after taking in that view.

That was part of the deal too.

Today though -- alone in the hallway outside Mr. Bythesea's office after 5 p.m. -- I paused, cocked my head, and listened.

The office had largely gone silent. It was a beautiful space -- it must have been 80 years old by then, all marble and hardwood, on the 30th floor of one of Acidalia's ancient skyscrapers -- but one feature of so many smaller offices fitting so close together was that you could pretty much always tell if you were alone in the suite. There was a small sound from Pristina's office -- maybe the click-clacking of a computer keyboard -- but that was all.

I sighed. On the one hand, Mr. Bythesea hated interruptions of any sort, especially from me. I was to be seen and not heard. On the other hand, I was already in trouble because of the emails from earlier today. I had already earned myself a spanking, and I didn't have any illusions about the fact that it was going to hurt. A lot. Mr. Bythesea's spankings always did.

I couldn't really make it any worse for myself. Or at least, I didn't think I could.

I checked myself in the hallway mirror near Mindy's desk. I adjusted the pink ribbon in my hair, but my makeup still looked good, even after a long day like today. It didn't hurt that I'd touched it up some too. I'd remembered to take the ribbon bracelet off my wrist this time before I'd started scrubbing the bathroom, and I slipped it back over my wrist now, knowing it was something Mr. Bythesea liked. Just like the lace choker at my throat. I'd kept my dress fairly clean, although you could see the red marks on my knees from where I'd knelt on the bathroom tile. In truth that was probably a point in my favor though; it always turned Mr. Bythesea on to see me on my knees.

I toyed with the idea of slipping out of my heels, and not just because my feet were aching at the moment. The heels had definitely been Pristina's idea; she'd told me she liked the idea of me having to experience what it was like to wear heels all day every day. It took me about six hours to see what she'd meant.

But taking them off would make me look shorter, maybe more vulnerable, wouldn't it? Or would it just annoy Mr. Bythesea, the fact that his free use sissy maid couldn't even keep her clothes on right -- even if someone else was just going to rip them off?

I almost pursed my lips thinking about it, but caught myself in the mirror at the last moment, preserved my lipstick.

I'd keep the shoes on.

I sighed and set the cleaning bucket with the toothbrush -- now black with grime from the bathroom -- on the floor next to Mindy's desk, very glad that, for once, no one was behind me to snag the view up my skirt. Then I crossed the plush carpet to the door of Mr. Bythesea's enormous office. I held my breath and listened a moment, hands clasped in front of me.

Then I took a breath, and gave a light rap on the door.

If he didn't answer, I promised myself, I'd just leave. I'd go take out the trash in Pristina's office and ask her if there was anything else she needed from me, anything for court the next --

"Come in," Mr. Bythesea said, sonorous voice only slightly muffled by the heavy dark wood of the office door.

I turned the doorknob and stepped inside.

Mr. Bythesea's office was gorgeous, always had been maybe one of the most beautiful rooms in the whole suite. The walls were lined with mahogany cabinets and bookshelves; a plush burgundy carpet filled the space beneath my shoes; and a massive, antique desk held sway over all. Behind that desk, enormous floor-to-ceiling windows offered a commanding view of Acidalia's distinctive skyline, all of it gleaming like liquid gold in the dying light of an October's early evening. I had spent hours on my knees in this beautiful room, scrubbing and dusting and polishing every inch of it.

And doing other things as well.

Mr. Bythesea himself had his expensive Italian shoes up on that colossal desk, his laptop in his lap, and he was leaning back in the plush leather chair as well. He still had his tie on, but had his sleeves rolled up to the elbow, displaying muscular forearms and one thin snake of a tattoo stretching from his right wrist to elbow. Most people didn't know about the tattoo; you would never have seen it in court.

He ran a hand over the light stubble on his jaw and surveyed me with dark eyes.

"Aysha," he said, using the new name he and Pristina had picked out for me. "What a surprise."

"Hello, sir," I said. "I just wanted to see if...if there was anything you needed before I check with Pristina."

The ghost of a smile tugged at his lips. He knew what I was trying to do, what my real aim was here. He shrugged and returned his eyes to his laptop, began typing again as if I wasn't there.

"Not that I can think of," he said. "I'll let you know when I'm ready for you later."

Ready for you later, I thought. I knew what that meant.

I took a hesitant step toward the desk, where he had his feet up, crossed at the ankles. Then I took another. He'd been in court all day, the first of a big trial, playing defense in a guns-and-drugs case. The Acidalia Times and the Galena City News and the Confluence Press had all been there, as well as just about every TV station within 100 miles of here. It had been a long, stressful day; he and Pristina had put in a ton of work on this case.

I knelt in front of the desk -- the plush carpet here felt better on my knees than the bathroom tile -- and reached up to one of his shoes. Then I began to untie it, slipped it off.

He didn't say anything at first, just rolled his ankle and scrunched his toes. I put my hands onto his socked foot -- still damp -- and began to rub.

"Mmmm," he said, and snickered. "Are you trying to get out of our little discipline session later?"

"No sir," I said, rubbing harder now.

He laughed again, but still didn't look up from his laptop. "In that case, then, why don't you take off the other one as well?"

He moved his feet, put the other one on top, and I undid the laces there too and slipped that shoe off as well. As I rubbed his foot, I bent to kiss it, careful not to smear my lipstick on his sock as I did.

I hated the fact that I could feel my chastity cage tighten in my panties as I did it.

"You looked great in court today," I said, and I meant it.

Mr. Bythesea -- famous in his dislike for opening statements -- had turned this one into a tour de force, a show in and of itself, and a perfect front page picture.

"Flattery's not going to get you anywhere either, Aysha," he said, without looking up. "You're getting spanked, and it's not going to be an especially easy spanking."

I nodded and kept my head down and stayed on my knees as I kept rubbing his feet. I kissed his toes again, then a few more times. He would never admit it, but I knew he liked this, from me. And not just for the humiliation it caused me either.

I slipped off his socks, put a kiss or two on his bare soles, and then kept rubbing, running my thumbs along the arches of his feet, heel-to-toe and back.

Above me, he snapped the laptop shut.

"All right," he said, and slid his feet off the desk. "As great as that feels, it doesn't get you out of the fact that you messed up pretty bad on a pretty basic task earlier today, does it?"

I glanced down at the carpet beneath my knees. Beneath the blush on my cheeks, I felt the blood rush to my face. "No, sir, I guess it doesn't."

Mr. Bythesea nodded. "And I know you know how you're going to be punished."

I nodded. "Yes sir I...I do."

"All right," he said. "Let's get you over my knee then. Come here."

I made my way around the immense desk to where Mr. Bythesea had slid his chair back some, away from the desk and his computer a bit. He gestured to his lap, the creased surfaces of his slacks across his knees.

I sighed and bent over them. The skirt of my dress didn't offer much protection in the best of times, but bent over like this, at this angle, it didn't do me any good: Mr. Bythesea pretty much had a view of my ass clad only in the skimpy panties he required me to wear.

He kneaded my ass with one strong hand now, then gave it a pat.

"You know, Aysha," he said, a contemplative note in his voice as he rested a hand on my ass, "maybe you failing the bar really all worked out for the best. I think you pull this look off. It's good for you."

I blinked, looked at the thick burgundy carpet beneath his chair and now my hands.

"Thank you, sir," I said, feeling ridiculous saying it, but not sure what else to say.

He gave a soft laugh at that.

"Untie that ribbon bracelet of yours and hand it to me," he said.

I paused a moment, unsure where this was going, and then did as he told me to. I handed him the ribbon.

"Good," he said. "Hands up, and behind your back."

I swallowed hard and then complied, put my hands behind my back.

He tied them together at the wrists using the ribbon, one hand on top of the other. It wasn't tight enough to cut off circulation, but I couldn't have slipped out of it even if I'd wanted to.

"Good," he said, and ran a hand through my hair again. "Now tell me, in your own words, why you're getting this spanking."

I blinked, felt the blood rush to my face, but I wasn't surprised.

"I...I screwed up the names on the thank-you emails for the day," I said. "I got the names all messed up and then I sent them out too early."

Mr. Bythesea kept his hand on my ass, seemed to nod above me.

"That's right," he said. "Aysha, I built this firm on nothing but a reputation. And in a place as relatively small as Acidalia -- a place with as relatively few attorneys as this -- reputation is everything. I didn't get here, to where I am now, by making these kinds of mistakes. These are the sorts of mistakes our clients expect us to avoid. Because if my firm can't even send out an email correctly, then how can clients expect it to represent them adequately in court. Do you see what I mean?"

I did. I closed my eyes and pursed my lips, resisted the urge to remind him that I'd almost been a licensed attorney at his firm, almost provided that adequate representation in court he'd just mentioned.

Key word there, of course, being almost.

"And I know you know this," he said, grabbing another handful of my ass and pinching it hard. "But clearly you need a reminder. And I hold my business in high enough regard to give you that reminder."

I sighed, shifted against his thighs, and said nothing. I tried to see if there was any play in the ribbon binding my wrists; there wasn't. Or not much.

He put his right hand beneath my chin, cupped it with a strong grip, just above my throat. If I swallowed, he'd feel it.

"OK," he said. "Count these off for me. And I want to hear 'thank you' after each one. And each time, I want you to think about how you can be more professional in the future."

"Yes sir," I said.

He pulled back and spanked me hard, very hard. I gritted my teeth and winced. No warmup then.

"One, thank you sir," I said.

His hand landed on my ass again, just as hard, and again I caught my breath.

"Two, thank you sir."

He spanked me a third time, hitting me on the upstroke in a way that always seemed to sting more than it should have. I winced, screwed up my eyes, and his grip on my jaw tightened.

"Three, thank you sir."

He hit me several more times, always aiming for the same places he'd already spanked me, wanting, apparently, to make a point, to drive that message home. I thanked him after each spank, just as he'd asked. He stopped at 20 blows, gave my ass a pat.

"On the floor," he said, and I knew what this meant. "And you don't have permission to touch your bottom."

I slipped to the floor, on my knees. My ass stung, but I resisted the urge to try to touch it. My hands were still tied at the wrists behind my back anyway.

I sat back on my heels before I could stop myself, then winced and took my stinging butt from the backs of my shoes.

I looked up at Mr. Bythesea. As I watched, he slid his belt off, meticulous, through one loop at a time.

He looked down as he did it, a single stray lock of dark hair falling across his sharp features, forearms working against his rolled-up sleeves as he freed the belt from its final loop and folded it in half.

"All right, Aysha," he said. "You know how this works. Stand up, and over the desk."

I did know how this worked. I gulped, stood, and bent over the desk's dark mahogany surface. I somehow felt even more exposed like this than when I'd been bent over his knee. Having my hands tied must have contributed to that, I thought. Normally, he made me put my elbows on the desk, and clasp my hands in front of me. This time, though, I just leaned over it, my wrists still bound and useless behind me.

I felt the belt's supple form against my ass, lower down, toward my thighs.

"Count these off again," he said. "And I want to hear that you're thankful after each one. You need this correction, Aysha."

I nodded and dropped my eyes to the carpet on the other side of the desk.

Then there was only the hiss of the belt through the air before it landed with a CRACK! against my upturned ass.

I gritted my teeth and winced, glad Mr. Bythesea couldn't see that.

"One, thank you, sir," I said.

He didn't wait long before the next blow, not nearly as long as I would have liked.

CRACK!

"Two, thank you, sir."

CRACK!

"Three, thank you, sir."

It went on and on, and then it seemed to go on and on and on after that, his hand on the small of my back. Normally he didn't spank me this fast. He seemed to want to make a point this time though. The carpet blurred before my eyes.

He paused and I blinked, thought about my mascara running. Not that that had ever been a problem. Half the reason Mr. Bythesea seemed to want me dolled up was so that he could smear my makeup like this, leave his mark.

I breathed out, then took a long breath, held it, and exhaled again.

"How many was that, Aysha?" He asked.

"I counted 20, sir," I said.

"Good," he said, hand still on my back, just above my tailbone.

He wasn't pressing down hard, but I knew he could. It kept me riveted to the desk sure as if he'd tied me there.

"Do you think you need more?" He asked.

He enjoyed these kinds of trick questions. No matter what I told him, I'd be getting more. I knew that.

"Only if you think I need it, sir," I said, and blinked away tears and mascara. "I know...I know I messed up."

"You did," Mr. Bythesea said, and put a hand on my stinging ass again. I winced. "You definitely did."

He moved his hand further in, between my legs. I jumped at that, hadn't expected it. He could, of course, do whatever he wanted to me though. He had before.

"I'm going to give you five more hard hits," he said. "With the buckle."

I closed my eyes and my heart sank. He really did mean business tonight. The buckle *hurt.*

He brought it down hard in the same spot he'd just hit me.

I sucked in my breath, sharp and fast.

"Twenty-one, thank you sir," I said.

He didn't let up, brought the buckle down again.

"Twenty-two, thank you sir," I said, slamming my eyes shut against the tears, feeling them run in twin mascara-stained streams down my cheeks.

He hit me again, with the same characteristic jingle and SNAP I'd come to hate from the buckle.

"Twenty-three, thank you sir," I managed.

"Two more," he said, giving me a slight respite. He pressed harder against my back, held me firmer against the surface of the desk. "They'll be quick."

They were quick. They were also hard, hard enough to make stars dance in front of my eyes. They landed in the same place on my ass, and I could all but feel the bruise forming in real time.

I yelped, couldn't hold it in, but then bit the sound back and gritted my teeth against the pain.