The Sissy Maid Ch. 01

When the ad leads with "Work from home dad seeks sissy maid" I simply had to click on it.

I'm a sissy, I thought, as I sat on the couch scrolling through the personals on my phone. I was wearing a short denim skirt that highlighted my smooth slim legs, and a white singlet with the word "Princess" printed across the chest in hot pink. I brought my feet up onto the couch and rested my chin on my knees. My little cock twitched inside the pink lace panties I wore. Yeah, I'm definitely a sissy.

And I like maids. Or rather, I like being a maid. Or maybe just dressing as one. I've got a cute little French maid outfit that I enjoy wearing around the apartment even if I end up not really doing much cleaning while wearing it. I suppose I do have to clean up some cum afterwards so maybe that counts. Anyway, I like maids.

I like dads, too, I thought. Well, to be precise, I'd say I like daddies. I've always had a thing for older men: my 45 year old neighbour, Robert, who makes me feel lightheaded whenever I say hi as we pass in the hall; Max, the 50-something owner of the coffee shop on the corner, who accidentally upgrades my small for a large every time I visit then cracks the same joke about preferring them big and black; several of my old high school teachers, and at least one university tutor; and of course my own dad, whose cock I would always steal a glimpse of whenever he was naked around the house, before retreating to my bedroom to jerk off. Yeah, I like dads.

The ad seemed targeted directly at me. Clicking through, I was not disappointed. A 54 year old man, running his business out of a home office located only a suburb away from me, looking for a young (but of legal age, of course) sissyboy to help him out around the office one day per week. Duties include cleaning, tidying, making coffee and "attending to certain needs". It even says a maid outfit is required to be worn at all times and will be supplied if necessary.

I couldn't believe what I was reading. It was perfect. I slid my hand under my skirt and felt my little cock. There was a damp spot right at the tip soaking into my panties. Opening my thighs, I pulled my panties aside to free my cock and scooped up the pre-cum on my finger before licking it clean and tucking my cock away again.

Hitting reply on the ad, I typed out a quick message to describe myself (21yo, 165cm, 62kg, 4" cock, smooth all over) and emphasise my submissive nature. Luckily, I already had a photo of myself dressed in my maid outfit (my phone is full of pics of me all dolled up, since you just never know when one will come in handy) so I attached it to my message and hit send.

Three days later and I'm standing outside an imposing security gate flanked on both sides by a two-metre stone wall. Beyond the gate, a gravel driveway disappears behind thick rows of tall trees and hedges, the upper floors of the house itself barely visible. Although clearly the biggest house on the street, it doesn't look out of place. The vast neighbouring lots are similarly appointed with locked gates and security cameras dissuading anyone who might mistake the yards for public parks. I, on the other hand, felt very out of place, standing awkwardly in my shorts and t-shirt, the bag containing my outfit slung over my shoulder.

Next to the gate, there seemed to be some kind of panel with a screen and buttons. Before I could take a closer look, a voice spoke from the panel: "Good morning. I see you are not in uniform. Please step through the gate and change in the guardhouse before proceeding to the front door."

"Hi?" I replied. "Mr Malone?" But the panel was now silent.

I heard a click and the gate swung inward. On the left was the guardhouse, a small room containing with a desk and several monitors feeding live footage from an assortment of cameras around the property. It did not currently house a guard. I dropped my bag on the desk and shrugged off my boy clothes. Time to suit up.

I stepped into the pair of panties I'd brought. They were a boyshort cut, sheer black lace with a white lace trim that felt amazing at the point it disappeared between my cheeks. Next I rolled the stockings up each of my slim legs in turn, thrilling at how they felt on my smooth, sensitive calves and thighs. I straightened the ruffled white lace band around my mid-thigh and admired how the otherwise dark stockings accentuated the curves of my hips.

The dress was the next item out of my bag. I slipped it over my head and wriggled inside before fastening the zip at the back. The shoulders were white satin with black lace trim that made my upper arms look so wonderfully slender as they extended from the short puffy sleeves. The black dress pinched tight at the waist then flared wide from the hips and ended maybe an inch below my ass, leaving a good couple of inches of bare, pale skin between its white lace frill and the tops of my stockings. Under the skirt was attached a white petticoat designed to fill out the lower half of the dress with greater shape. Over the top I attached a white stain apron with a black ribbon tied into a cute bow on the chest and a larger one serving as a belt at the waist.

Finally, I attached the black and white frilled hairband, slipped on my favourite two-inch black stiletto heels (well, they were the only ones I owned) and touched up my makeup using my phone camera as a mirror. I wondered if Mr Malone had been watching me through one of his security cameras. Looking more closely around the room, sure enough I spied a tiny camera in the ceiling. I blew it a kiss and twirled extravagantly before stepping out of the guardhouse.

Navigating the long gravel driveway in these heels was tricky, but soon the house loomed ahead. It was even bigger than I expected, sprawling away in all directions and rising to three storeys. Surely I wouldn't be expected to clean the whole house? It'd be a full-time job in itself. I wondered how big Mr Malone's home office really was, what sort of business he ran, and why he needed such an enormous home if he lived all alone?

The double front door was absent any obvious bell or knocker, so I decided to wait in front of it, feeling only slightly less awkward than I had outside on the street. Soon the doors opened and a middle-aged man wearing only a burgundy bathrobe ushered me inside.

"Hello, Amy," he said, gesturing for me to step inside. "That's what you want me to call you, yes?"

I tottered past him into the expansive foyer. "Yes, Amy, please. And should I call you...?"

"Mr Malone is fine. Or simply Sir, if you prefer. Please come through to my office and let me get a good look at you."

He swept through a chamber on the left, down a hall, through another room and eventually opened a further double-door leading to what was clearly an office designed for a wealthy man performing higher functions of industry. Mr Malone turned to face me and spread his arms.

"This is where I work," he said, smiling broadly. "When I work, that is. Wednesday is my designated work day, as it is yours. And as today is Wednesday, I shall be working and you shall be assisting me, Amy."

I stifled a giggle. He looked at me curiously, and for a brief moment I thought he might be irritated that I had laughed, but then he smiled again. He had a genuine smile and a friendly face, even he seemed slightly eccentric. I realised he was taking a moment to study me. I could feel his eyes wandering up and down my body.

"Turn around for me," he ordered. So I did. Slowly turning so he could enjoy the rear view. Then I spun around quicker, letting the air lift my skirt and teasing him with what was hidden beneath. When I was facing him once more I met his gaze and instantly sensed a flash of lust in his eyes that made my little cock throb with pleasure. He smiled again.

Balding, overweight but not obese, no more than average height, few would describe him as good-looking, but he had a certain rugged appeal. Very much a Daddy figure, with thick hairy arms and plenty of belly. He had the look of a man who had lived well all his life. I didn't find him unattractive.

"Please, put your things over there and we'll get started," he said. "I'm very much looking forward to working with you, Amy."

Mr Malone sat in a very expensive leather chair behind a very expensive wooden desk and recited the list of tasks he expected me to perform every Wednesday. Knees together, I sat on the small chair in front of the desk, taking notes with the pen and paper he had provided. My explicit duties, it seemed, were straightforward: when Mr Malone was present and working I would be expected to clean the office, dusting the considerable number of surfaces with the featherduster he had presented to me and wiping the numerous windows that filled the walls in the few spots there weren't bookshelves to dust; and when Mr Malone was not present, I could do as I pleased, reading while reclined on one of the several leather couches, perhaps, or trying not to fry my delicate skin while sunning myself on the deck adjacent to the office.

My implicit duties were another matter. Mr Malone offhandedly mentioned "other tasks as necessary" or "whatever else may arise" and remained coy about the precise details. I didn't press him on it, as much as I found myself increasingly wanting to, preferring instead to let the suspense accumulate. I would find out soon enough, I assumed.

"Did you have any questions, Amy?" Mr Malone asked, propping his elbows on the desk and steepling his fingers. "Oh, and would you mind fetching me a coffee? Black please."

Obviously, quite a few questions popped into my head as I walked over to the side table where Mr Malone had indicated I would find the coffee. "Um..." I delayed, placing a pod into the machine and one of the tiny cups under the spout, before pressing the button. I looked back over my shoulder in a manner I hoped looked cheeky in a sexy, playful way.

"So, do you always wear a dressing gown to work?"

Mr Malone barked a loud laugh. "I can see we're going to get along very well indeed, my dear Amy," he said. "I do prefer the comfort of a robe when I'm at home, in fact. My work can be... quite stressful... and I find it more enjoyable when I am completely relaxed."

I watched his eyes crawling all over my body as I walked back to the desk and placed the coffee before him.

"Thank you, Amy, and please, help yourself, too. There's tea, water and juice as well. At 1pm I'll send you to fetch lunch for us, but if you are hungry before then there are plenty of snacks next to the coffee machine. Now, how about you pick up that duster and get to it. I've got a phone call to make."

With that, my life as a part-time sissy maid began in earnest. I started dusting near the door, working my way around the room and making sure I attended to every shelf, table and other dustable surface. Even in heels I had to stretch up on tippy-toes to reach the top shelves. When it came to the lower shelves and coffee tables, I made a point of bending over provocatively, my ass always point towards Mr Malone and his desk.

Now and again I'd look his way and try to catch him checking me out. I caught him every time without fail, even when he was mid-sentence on what was undoubtedly a vital business call. I'd catch his eye and smile. What he didn't notice was how my little cock would stiffen each time, its excitement hidden beneath petticoat ruffles and black lace.

Soon it was nearly 1pm and Mr Malone looked up from his desk and announced he would like to eat. "Amy, can you please go to the front door and buzz in the lunch delivery? He should be here any moment now."

"Um ok?" I stuttered. Did Mr Malone somehow order in when I wasn't paying attention? Was there actually a delivery man at the front door? And was I expected to let him in to collect the food? Would he see me dressed like this? All these worries bounced through my mind on the hesitant walk to the front door. What would I say to him?

The buzzer sounded just as I noticed the panel near the front door. On it, a small screen showed a man standing at the gate, several boxes in his arm and a conspicuously budget car half-parked in the driveaway. I pressed a button and tried not to sound as nervous as I most certainly was.

"Hi? Uh... come in? I guess?"

"Thanks," he said, and walked through the slowly opening gate. I steadied myself with a few deep breaths and gently opened the front door just a few inches. He was walking up the drive, looking all around, clearly amused by where he'd briefly found himself. He saw my head peeking through the doorway and collected himself, quickly putting on a more appropriately serious face.

"Amy?" he said, now standing at the entrance.

"Um... yeah?"

"Your lunch," he said, holding the boxes out for me to take.

I had no choice. I couldn't stay hidden behind the door and take the boxes at the same time. I just had to accept that this random food delivery guy was going to see me--a guy probably about the same age as him--all dolled and dressed up in a slutty French maid uniform. And there was nothing I could do about it. Oh well, I realised, I may as well give him a good story to tell his mates.

"Oh thank you, sweetie," I said, putting on my most ridiculously over-the-top little girl voice. I opened the door fully and stepped out, accepting the boxes from him with a cute little curtsy and deliberately running my fingers across his hands before grabbing the boxes. His eyes widened and his cheeks turned red. Now it was his turn to stammer.

"Oh... uh... no worries, Miss... uh, Ma'am... um... enjoy your... meal."

After elbowing the door closed, I watched from behind the curtain as he walked back down the driveway seemingly in a daze. He stopped once, and looked back, as if he couldn't believe what had just happened. I kept watching via the screen on the panel and saw him close the gate behind him, shake his head once last time and jump into his car. Walking back to Mr Malone's office, laughing to myself, I could feel an extra strut in my step.

After lunch, I continued to clean as Mr Malone worked. His work seemed to largely consist of long phone conversations that, to my ear at least, only rarely detoured onto the topic of business. Still, I was here to dust and look pretty, so I remained focused on that. At one point, pretending to find something utterly fascinating underneath the coffee table in the centre of the room, I proceeded to get on my hands and knees and wiggle my thoroughly exposed ass in Mr Malone's direction for a good few minutes. Later, I reached the bookcase behind his desk and made a fuss of squeezing past him, greatly exaggerating the contact of my bare thighs brushing against his arm.

Around 3pm, Mr Malone excused himself from the office, saying he had "other business to take care of" and that he would "return later." Meanwhile, I was welcome to "do as I pleased." I decided to give my feet some rest and sit down in the sun outside. I had no idea where he had gone or when he would return, so I killed time on my phone and looked out on the garden. It had been a very weird day so far, but a fun one. Mr Malone was a complete gentleman and I'd enjoyed teasing him for much of the day. Even the anxious moment with the delivery guy had turned out to be quite funny in the end.

Still, two things left me slightly concerned. One, Mr Malone had wanted someone to visit every week, but I didn't know how many more times I could pretend to dust his shelves. I'd get bored soon, surely? The other concern was a larger unknown: What else would Mr Malone expect from me? Clearly, he found me attractive, but he hadn't made any moves on me. In fact, he hadn't touched me at all, except when I rubbed my thigh against his arm. Maybe he just wanted something pretty to look at, something that did indeed, as he claimed, help him relax? It didn't make sense to me. No man invites a "sissy maid" into their home for purely innocent reasons. Or so I had assumed.

It was nearly 5pm when Mr Malone returned. I was curled up on the couch next to the window, having briefly dozed off trying to read one of the very boring history books I'd picked at random from the shelf. While he returned to sitting at his desk, I quickly stood up, adjusted my dress and headband and went to resume my duties.

"Come here, Amy," Mr Malone said, the first words he'd spoken since returning to the room. He tapped the arm of the leather chair, indicating I could approach his side of the desk.

"You have performed your duties well today, with a grace and humour that did not go unnoticed. Very impressive for your first day on the job."

"Thank you, sir," I replied, now standing just to the side of his desk.

"Come closer," he said, that now familiar broad smile on his face. He swivelled the chair to face me. He was leaning back, sitting low in the chair, his belly filling the robe, his knees wide apart in the classic manspread position, the robe parting to reveal a surprising amount of hairy thigh. He looked extremely relaxed. I guess I had done a good job, after all.

"You'll find your day's wages in there," he said, pointing to an envelope on the desk. I picked it up, opened it and audibly gasped. It was five times what he had promised. He smiled again.

"But before I let you go," he said. "I wanted to show my appreciation for everything you've done today. Think of it as a special treat for a deserving girl. Kneel down."

Still stunned at the amount of money he'd put in the envelope, I nodded dumbly and knelt before him. He was already undoing the rope that held his robe closed. He edged the chair forward so his feet were either side of me and my head was basically between his knees. Then he opened his robe.

His chest was covered in fine black and grey hair, with slightly thicker curls down in the centre and ringing his nipples. The hair continued down over his round belly, forming into a thinner trail that ran over a roll of flesh and down from his belly button to his crotch. There, the hair flourished again, a darker nest of curls around the base of his large and very fat cock. Below, his hairy balls hung low, now spilling over the edge of the seat and dangling between his large, meaty thighs.

I found myself transfixed by his cock. He wasn't yet fully hard, it still draped slightly down over his sack, but I could see it rising slowly. It wasn't a huge cock; it was certainly much bigger than my own, and significantly longer. But what was truly impressive was its girth. It was comfortably the thickest cock I'd ever seen in the flesh. So much flesh. He wasn't circumcised, but the huge head was already emerging from its sheath and I could see a droplet on the tip glistening in the late afternoon light.

Mr Malone placed a hand under my chin and tilted my head up to look him in the eye. "Do you like your present, Amy?"

I nodded again, my tongue quickly darting out to wet my lips. I wanted his cock so badly. The sight of it had wiped everything from my mind. All I could think about now was this deliciously fat cock in front of me, this mouth-watering, manly dick being offered to me. This huge, hairy cock had already filled me up completely and I had even touched it yet.

I reached out and wrapped my right hand around the shaft. It was so thick my hand couldn't wrap all the way around. I took the head to my mouth, kissing it first then taking it inside, rolling the foreskin back past the head as I took more inside my mouth. He was completely hard now and leaning even further back into his chair. I held the shaft of his massive cock in two hands now, massaging his foreskin up and down in a rhythm to match the bobbing of my head, my lips and tongue lapping at the fat head like the world's biggest lollipop.

I wasn't sure if he had any other plans to reward me today. Was he just going to let me suck him? Was he planning to fuck me too? Did he want me to make him cum now? Or should I slow down and make it last? Right now, all I knew is that I wanted nothing else but his cock. My entire world was reduced to this: My hands and lips and tongue wrapped around the hard dick of a old, fat man I'd met today for the very first time. I didn't want to leave.