Worlds First Futa - Sissy Maid

Note to readers: This story and all its connected chapters contain depictions of somewhat unrealistic proportions, body sizes, bodily fluids and sex acts, though not enough to be considered "Hyper".

If you do not like that sort of thing, no judgment, but please go elsewhere and there is no need for pointlessly negative comments. Constructive criticism is extremely welcome however.

All of my WFF stories take place at different times during the life of the titular character. They are intended to be mostly standalone and will never be more than tangentially connected so that they can be individually enjoyed.

However, I would highly recommend starting with the prologue as this gives a lengthy introduction to the main character, Sam, and gives important insight into her personality moving forward.

Having said all that, please enjoy the story.

T.

World's First Futa -- The Sissy Maid

My name is Samantha Stevens and as far as I know, I am the first true futa to ever be born, a perfect mix of both genders.

The story I'm about to tell you about my life takes place not long after my 22^nd birthday. I had finished my time at university and earned a degree in Molecular Biology, and had just started working as a Lab Assistant at Synth Gen, a local biotech firm that specialized in melding the biological with the mechanical, such as advanced prosthetics for amputees.

Given the unique nature of my own biology combined with the amount of time I had spent in the presence of doctors, scientists and other medical professionals during my childhood, it probably came as no surprise to anyone that I had gained a keen interest in this field, and chose to pursue it as a career.

The other side effect of all the time I spent in medical care as a child, was that my family was given a considerable stipend in recompense for the testing and studying that was conducted upon me. Don't worry, it was all above board and nothing heinous took place but there was a lot of interest in my unique situation.

That interest eventually waned as I entered my teens, and testing had shown that my birth was an almost impossible statistical probability that could not be replicated. Consequently, I was able to enjoy my teens in relative normality and my family was more or less set up for life.

We were never ultra rich but always lived comfortable in a nice house, I attended a good school and I never lacked for anything. I could have turned out a spoiled brat, but my parents are awesome and managed to keep me well grounded.

The money also paid for most of my education, and was now allowing me to live near to where I worked in a fairly spacious two bedroom flat. It was honestly a fantastic place to live, free parking, ten minute drive to work, and within walking distance of the city's nightlife but not close enough that it kept me up every weekend.

I had been living there for around three months, just about managing to balance work, free time, and a social life. The only problem I encountered, especially as I am a naturally fairly messy person, is that keeping the place clean was really starting to get on my nerves.

I glanced around and could see a sink piling up with unwashed dishes, my laundry hamper overflowing, dusty shelves, old coffee cups and wait, was that a pair of panties hanging off a curtain rail? They weren't even mine. How did they get up there? I shook my head and sighed, this place really needed a good clean. Unfortunately I was already on my way out the door for work. I would have to come up with a better solution.

When I got home that evening, I made a halfhearted attempt to tidy up but was already pretty tired so I didn't get very far. As I slumped onto the couch, a thought struck me, why am I doing this myself? I have a good job so why not just hire a maid?

The more I thought about it, the more it seemed like a perfect solution. I could come home to a clean house! I won't lie and pretend that I didn't have any ulterior motives either. The thought of a sexy little thing cleaning up after me, in a perfect position for me to seduce was an exciting proposition. It wasn't like I was ever lacking in female companionship, quite the opposite, but my hefty cock had a mind of it's own and was always on the hunt for a new hole to breed.

I immediately fired up my laptop and started searching for a company that was hiring. The few that I could easily find ended being too expensive, or didn't have anyone available at the moment. I decided to put out a personal ad through various sites, and see if I could find someone looking for some extra cash. I also rationalized that if I did end up fucking my maid and lets face it, I would, then it would probably cause less problems if she wasn't employed by a separate company.

The ad that I ended up putting out was short, to the point and wasn't sleazy. I did actually want a proper maid after all. Of course the plan was to fuck her, and that way I had a cleaner plus another cocksleeve I could use at my leisure. You can't just advertise for that though!

I set the interviews for the next weekend and went to sleep.

Unfortunately, I got an extremely limited response to my ad. The only candidate of any real potential was a girl called Jamie. Her email response was very timid, and claimed that she was only 18, hadn't had a real job before but was very eager to prove herself. She seemed almost too perfect, breaking a shy teenager on my cock was one of my favorite pastimes after all. I responded in the affirmative, told her to come in clothes she felt would be appropriate wear for a maid, and be prepared for questioning and a hands on interview. She responded quickly, and told me she would be there at 9 o'clock sharp.

I was already stroking my cock in anticipation.

DAY 1

I woke up early on Saturday morning, eager for my interviewee to arrive. I dressed casually, but still a little provocative. I wore a long, loose sweater without a bra, and some cute leggings that I use for yoga. The sweater was way too big, and fell down past my ass. It also conveniently covered my bulge, didn't want to scare her with that right away! I looked good, but not too obvious.

I made a hearty breakfast, and deliberately left the kitchen messy for her practical test. I had just finished clearing off the table to make space when the doorbell rang.

I composed myself and opened it. What I saw was not what I was expecting. Before me stood a boy, an effeminate boy but a boy nonetheless. He was around 5 and half feet, so quite a bit shorter than me, had slightly wavy light brown hair that came down to his shoulders, thin arms and a surprisingly skinny waist that quickly widened into very womanly hips.

He was staring at me the same way I was at him, though perhaps a bit more awestruck. I know I'm damn gorgeous, even without putting much effort into my appearance. I let him stare, taking a few more seconds to analyze him in return.

He was wearing skinny jeans that very closely hugged every curve and a plain black t-shirt that was tight around his chest. I could see the barest hint of his nipples protruding through.

I focused on his face, which was just as cute and androgynous as the rest of him. It was slightly round, with high cheekbones and a small nose. He was clean shaven, but as I looked closer I realized it wasn't just shaved this morning but actually looked like he didn't grow facial hair at all.

Overall, he was quite a mystifying package. I wasn't usually very attracted to guys, but he was already so girly and curvy that I could feel a slight swelling in my cock. I wondered what it would be like to top a boy like him, and if I could dominate him the say way I had so many women.

"Ex...excuse me?" he asked, his voice soft and meek. "Are you Miss Stevens? I'm here about the cleaning job."

Fuck, I'd been staring a little too long. Well, time to turn on the Dom and put him in his place right from the start.

"My ad specifically requested a woman" I said bluntly.

He nervously took a half-step back and looked down at the ground. I watched as he mustered the courage to speak.

"I'm sorry Miss Stevens, I know that. I'm just really desperate for a job, any job. I'm really hard working, available immediately, and I'll do anything you want. Please give me a chance."

Oh my god this boy was just too cute.

"Ok, Ok, no need to beg. Come in."

I stood to the side and let him enter my apartment.

"Take a seat" I said, pointing to the kitchen table.

We sat opposite down opposite each other. I simply watched him in silence for a minute, letting him stew.

"So Jamie, why should I hire you?"

"Like I said before, I-"

"Yeah, you said that before. That got you in for an interview. Give me a reason to hire you."

"I've got a lot more pretty women lined up to interview after you."

I didn't, but he didn't need to know that.

"I can't, but please give me a chance, just for a few days to prove myself. You won't be disappointed."

God this boy was kinda pathetic, but cute though, I could work with that.

"Why are you so desperate for this job Jamie? It's only part time cleaning work."

"I need the money, because I need to impress my girlfriend."

"Oh?"

"Yeah, her name's Maria, she's a little older than me and probably out of my league."

"She has a good job at the gym, rents the apartment we live in and is doing really well for herself. I'm really lucky to have met her when I did but I know she can do better and I don't want to lose her. Even a part time job would at least allow me to pay rent and stuff."

"Here" he said, flicking on his phone and showing me the background photo.

It showed a young Latino woman in a very tight fitting gym uniform, slightly bent over in front of a changing room mirror, looking back over her shoulder and blowing a kiss at the camera. Her absolutely gigantic ass featured very prominently.

"I think you might be right, she is out of your league!" I teased him gently.

He smiled coquettishly and looked away from me, blushing.

"How did you manage to land a girl like her?" I asked.

"I was so lucky. I was almost homeless at the time. I'm an orphan you see, can't even remember my parents and I've lived in an orphanage my whole life. Thing is, you aren't allowed to stay once you turn 18."

"They gave me some money when I left but that quickly went, I never got much of an education and I've been really struggling to get a job."

"I'd been sneaking into the gym when it was late to use their showers and one day she caught me. I think she took pity on me because she bought me dinner and said I could stay at hers for the night. I stayed on the couch at first but she kept looking after me and we spent more and more time together. I think she liked taking care of me."

"Somehow, we ended up together and I've kinda been living with her ever since."

"I think it's called the Nightingale effect, have you heard of it?"

"No, but I think I get the idea."

"She's been so good to me but I think the novelty of looking after me is wearing off. So that's why I really need this job."

I wasn't exactly sure how much of his little sob story was made up, but he did seem sincere. I decided to give him a chance.

"Ok, I get it. Let's move onto the practical aspect of the interview. If you do well enough at that, I'll consider you for the position."

His eyes lit up at my words. He clearly was very eager.

"Of course, what would you like me to do?" he asked.

I pointed at the pile of unwashed dishes and general mess of my kitchen.

"Clean everything in the kitchen to my satisfaction within 30 minutes and the job is yours."

"No problem Miss Stevens, I'll get right on it."

He spun around and turned on the tap, then started maneuvering the dishes into position.

"Aren't you forgetting something?"

He turned back to face me. I smirked and pointed at the pinafore hanging from a hook nearby. For those of you who don't know, a pinafore or 'pinny' is the white piece found on the front of the classic french maid outfit that has it's routes in traditional maid attire. It used to contain a large pocket and was meant to help avoid staining the uniform underneath but these days they are normally a frilly show piece more than anything else.

The one on the wall was exactly this, a pure white piece of silk with tasteful frills lining the underside of its oval shape. It hangs off the shoulders and ties up in a cute little bow round the back. It was actually part of decidedly sexual french maid outfit I had bought for the girl I hired to wear, but this was close enough.

Jamie visibly gulped, and I could see his internal monologue playing out on his face. After a few seconds, he clearly decided that this minor humiliation was worth it, and slipped the pinny over his head before tying it behind his back.

"Good boy" I said. He blushed furiously, looking very cute.

He turned back around and began working. I was content to sit and watch patiently. After a minute, he asked where the dish soap was kept. I told him to look under the sink, at the back. He bent down, pulled open the cupboard and began rummaging around.

To be frank, I had engineered this exact scenario, hiding the bottle right at the very back of the lowest shelf. Jamie had to get down onto all fours to be able to reach inside. His fat, bubbly ass was pointed right at me. The tight jeans he was wearing hugged every delectable curve perfectly and there was no discernible bulge between his thighs. You could have easily convinced me I was looking at a woman, and a fit one at that.

My own cock began to swell, inching its way down my thigh inside my leggings. Ok, I was officially interested now. I surreptitiously began to rub myself, enjoying the show.

Jamie stood back up, clutching the bottle. He flashed me a quick smile and got back to work.

Over the next half an hour or so, he worked diligently to clean away the mess. I paid that no attention, and simply fantasied about him. I imagined this girly boy wearing the full french maid outfit, tottering around in stiletto heels, bending over to dust, his cute panties peeking out from under his skirt...

"Miss Stevens?"

"Hmm? Oh, what is it Jamie?"

"I said I'm finished."

I shook away those thoughts and examined the kitchen. It was spotless, he had actually done an exceptional job.

"Very good Jamie. I really like what I've seen today."

His face broke out into a huge smile.

"Does that mean..."

"Oh yes Jamie, you're going to be my maid from now on."

"Thank you, thank you, this mean so much."

"Ok, Ok, no need for all that. We'll start at a few hours per day. Be here at the same time tomorrow morning. We can discuss the other...details of our arrangement then."

"Of course, Miss Stevens, no problem at all."

The little thing was so excited, he really was very cute. He kept rambling on as I showed him to the door. As he made to leave I grabbed him gently by the shoulder and pointed down. He was still wearing the pinny.

He blushed furiously and untied it.

"Guess I got used to wearing it."

"Of course. See you tomorrow Jamie."

DAY 2

Jamie arrived right on time the next day. I let him in and told him to get started.

I left him to it and retired to my bedroom to think. How was I going to go about feminizing him and seducing him? It would have to be slow, too much too fast and he would flee. I needed him to feel that what he was doing was alright, and even what he actually wants.

He was already very girly body wise, and had quite the submissive attitude, so with the right amount of pressure he should crack easily enough.

I also knew his weakness, he desperately wants this job to impress that girl and he already admitted doing anything to keep it. So that was where I would need to apply the pressure, but how to begin?

I was broken out of my thoughts by a loud bang from the kitchen.

I rushed out to find Jamie on his knees by the sink, a bottle of bleach leaking onto the floor, most of its contents clearly having splashed all over him.

"Shit, crap, fuck..." he mumbled, desperately trying to clean himself and the mess he made.

He panicked when I walked over, standing up too fast with the bottle in his hand and spilling even more all over himself.

"I'm so, so sorry Miss Stevens. The top was stuck so I tried to twist it...and then it...and then I...I'm sorry."

"It's alright Jamie" I said soothingly. "It won't stain the tiles."

"Your clothes on the other hand..."

His jeans and t-shirt were already ruined, big white stains covering them both.

"Oh no, what a disaster..."

Jamie stood there, looking dejectedly down at his feet.

God, what an absolutely golden opportunity this was. I was just wondering how to start imposing my influence on him and this happens. It was perfect!

I strode confidently over to him, a deftly grabbed the bottom of his t-shirt, pulling it up and off his head.

"Wha-"

"Quiet, I can't have my maid looking like a complete mess."

I worked quickly, before his brain could catch up to what was happening. I soon had his trainers off, then his jeans as well. He stood before me in naught but his boxers.

"Bathroom's down there, first on the left" I said pointing down the hall.

He blushed furiously under my gaze for a moment and then scarpered.

"Use any towel you like!" I called after him, grinning to myself.

I heard the shower start up. I grabbed an old tea towel, roughly mopped up the spilled bleach with it, then threw it, his clothes and the empty bottle into a garbage bag which itself went straight into the chute outside.

That's his clothes gone I mused. I went into my bedroom and pulled open the bottom drawer of my large dresser. The drawer itself had a small engraving of E.G on the front and was where my best friend/lover/favorite cock socket Emily kept some of her things, including spare clothes.

Any of mine would be too big for him, but at 5'3" Emily was only a bit smaller than Jamie and her clothes would likely be the perfect fit of just too tight. I picked out a cute pink crop top and some thick, black leggings. Girly, but not ridiculously so. Just the right amount of humiliating I had in mind.

I was carrying everything back into the living room when I heard the shower shut off.

I crept down the hall and noticed the door was ajar, he must have been in a hurry to get away in his semi nakedness and forgot to shut it. Excellent. I peeked inside and saw he was currently drying himself. His body was pretty much what I had expected.

There was no muscle or fat to him at all, all soft and smooth curves. He was almost completely hairless too, a few fine hairs in his armpits and above his crotch were the sum total. As he lowered the towel to his legs and revealed himself to me fully, I had to try very hard to stifle my laughter.

His cock, well his penis, was tiny! It was an inch or two long and sat above a pair of balls each about the size of a grape. I could have cupped the entire package easily in one hand. Seeing this brought a flood of endorphins to my hind brain, the dark little voice that I let take over in full Dom mode was exultant to see my superiority confirmed.

He finished drying himself and hung up the towel, then pulled his boxers back on. I was about to duck away when I saw him stop, his gaze fixated on the open laundry basket. Sitting on top was yesterdays thong.

I have to wear special underwear to keep my cock contained and used to wear a brand designed for well hung men that was essentially a kind of jock-strap. As you can imagine the design was exceedingly masculine and I really didn't like it, but simply couldn't wear normal panties as my cock refused to be contained. I eventually reached out to the company that designed them and after I sent a few choice photos, they custom designed me a much more lacy, feminine version I've been happily ordering from them ever since.