My Life as a Maid Pt. 01

Outcast

My mom bailed me from the county jail after my DUI arrest. I had only been inside for a few hours, but I'd never been more worried or bored in my life.

When we got home, my rucksack was waiting by the door, all my worldly possessions were packed in it, my father picked it up, threw it at me, and invited me to leave his house.

That sucked.

I was what he termed a problem kid. I smoked, I drank, I didn't do very well in school, and trouble with the law was the limit his fundamentalist Christian values could endure.

My mom did me one last favor, she let me use our home address for my court appearance. I received a small fine, which she paid, and a one year suspended sentence.

I found that funny, I didn't have a home now, never mind a car, so it wasn't like I was going to be picking up any traffic tickets anytime soon.

In the meantime, I had crashed with acquaintances here and there, but I moved on from each after a few nights so as not to wear out my welcome, within a few weeks I had nowhere left to go.

With no job and no money, I ended up sleeping rough and begging around town for what little I could raise.

Caroline McDonald was an acquaintance in school, good student, cheerleader, very pretty, she had always been nice to me in a solid "Friend zone," sort of way.

I was sitting shivering in the rain begging for spare change when she passed me.

"Gerry, is that you?"

I looked up startled to hear my name, "Oh, hey, Caroline," I smiled at her, she told much later on, that I looked like a soaked puppy and that's one reason why she took pity on me.

"What the hell's going on Gerry?"

She looked over to the Starbucks on the corner, "Want a coffee?"

"Sure, right now, I'd die for a coffee."

I followed her over the road, a hot drink would be revitalizing after a miserable morning sitting on wet and cold concrete, we settled into a table in the corner, and I told her my tale of woe.

"Your Dad always was a hard ass," she said after I had finished.

"I didn't help matters much," at least I could be honest, "doesn't matter now, no going back, the prodigal son has outstayed his welcome."

I went silent for a while, "I do sort of my miss mom though."

"So you're sleeping on the streets?

"What about a job?" She asked me.

"The streets aren't so bad, as long as you can find somewhere safe to hide at night."

I paused to take a drink, the coffee was warming me from the inside.

"A jobs almost impossible to get, even at Mickey Ds, without a home address."

She was thinking, "I know the hostel where I live is looking for a cleaner.

"It's room and board, not much, but it's got to be better than begging outside a bank, right?"

A New Beginning

I found myself standing outside the hostel while Caroline went into talk to its matron.

Twenty minutes had passed, maybe, I didn't really know, my watch had been pawned long ago, then the door opened and Caroline beckoned me up the stairs and into a sitting room on the right.

A middle aged woman was its sole occupant. She was sitting on a plushly cushioned high backed arm chair, her well-dressed figure was trim, and she didn't have much makeup on. She was obviously comfortable and gave off an air of complete self-possession and control. The whole effect made her look very attractive to my eyes.

Caroline introduced us, "This is Ms. Graham, she runs the hostel."

"Sit Gerard, please," she pointed to a chair beside her, "Caroline has told me your story, she's even given you a reference for a job here, there is just one small problem."

I nodded and she continued, "This hostel is for women only, and that includes the staff."

I stammered a thank you and started to rise.

"Wait," she said, "I would like to help you, but it will be a little difficult, and I will need your full cooperation."

I had no idea where this was going, so I sat down again.

"I can give you a job, it comes with Room, Board, Uniforms, and a small allowance.

"However the job opening I have is for a maid, and all my maids have to be female, you will need to dress in a maid's uniform, you will need to learn to walk, talk, and act like a girl to pull that off."

I didn't have anything to say, so I nodded and Ms. Graham continued.

"It will not be a problem with the ladies here, I will inform them of your situation, and I know I will have their complete discretion.

"But they do have visitors, and it would be a significant problem if an outsider was to discover your real sex, we would both be in a bit of trouble then."

"How?" I managed to mumble.

"As I said, the job comes with uniforms, I am sure we have the right sizes for you, once you are dressed up, that is the biggest part of the problem solved, well as long no one gets too close to you, too soon.

"Longer term, I can work with you on developing your feminine side, it is lucky you are so short and have a thin build that will make the job easier."

I wasn't sure about long term, but this morning my long term plans consisted of getting through the day fed and finding somewhere safe to sleep.

"Can I ask why you're doing this?"

"I have been in your situation, I know what it is like to be cast out from your family.

"I was helped along the way when it happened to me, and although this may seem like it is an unusual way of repaying that debt, I think it is something I should do."

She could see I was still hesitant.

"Try it for a little while, it will give me time to see if I can find something more suitable in the meantime.

"If it does not work out, you will at least have had a warm bed and some good food for a few days, and you will not be hiding in a culvert from the vultures."

Well, she did have a point, right now I was feeling very worn down, a few decent nights' sleep, even at the price of dressing in a maid's uniform didn't sound too bad a price to pay.

"Ok, why not!"

"You must call me Ms. Graham, come, I will show you to your room."

Maid

She led me to the rear of the hostel, where we climbed three flights of narrow stairs. She opened a door with 3B in brass letters on it, into a narrow room.

There was a single bed, a narrow three high chest of drawers at its side, and beside that a narrow closet. There was no window, but at least it had a fan on the light to circulate the air around.

The room was comfortably warm after my nights on the streets. It wasn't the Hilton, but it would certainly do for now.

"This was Mary's room, she was about the same size as you, so the clothes she left behind should fit, and if they need a little tailoring, I can do that for you."

She gave me a few more instructions and left me to my thoughts, they were mostly confused, but I was too tired to worry about that.

I stripped down to my boxers and t-shirt and fell asleep as soon as my head hit the pillow.

In the morning Ms. Graham knocked and entered my room to find me sitting on the bed.

"Good you are already up, it is going to be a long day, best get started."

She opened the drawers and quickly laid out matt pumps, stocking and suspenders, and a plain bra and panty set, all in Black, from the closet she took an old fashioned maids uniforms and placed it on the bed

"That should do for now."

The reality was setting in, and I was getting somewhat apprehensive about this arrangement now.

Ms. Graham looked at me, "Grab those clothes and come with me please."

She led me down the narrow hallway to a set of bathrooms at the end of the corridor, she opened the last door and once inside ran a bubble bath, it smelled of Lavender.

"Strip dear, quickly now."

I hesitated, "Err Ms. Graham, it's just that I've never, em, well..." I trailed off with embarrassment.

"You have never been naked in front of a stranger before?" She queried me, there was a hint of disbelief in her voice.

I think she was a little surprised when I answered, "Yes, Ma'am."

"Strip Geraldine, there is little privacy in a house like this, as you will soon see, you will get used to it, I promise."

She hadn't called me Gerry that time, she had feminized my name, I wasn't sure how I felt about that, but then I looked at the women's clothes in my hands, and laughed at myself as if a name was the biggest problem I had to deal with right now.

I took off my clothes and rolled them into a bundle.

Ms. Graham took it from me, "I think these need cleaned," she sniffed at them, "or burned, into the bath dear."

I lay down in the bath, after weeks on the street the experience was absolutely fantastic, I wasn't sure of the last time I felt warm or relaxed.

Ms. Graham gave me a few minutes to soak while she prepared some things, then she handed me shampoo, soap, and gave me some foam and a razor.

I shaved my thin scraggly beard while she looked on.

"Now your legs dear, girls shave their legs."

She gave me instruction on how to accomplish the task efficiently without cutting my legs to pieces.

"You do not need to shave your pubic hair off dear, but a little trim would be nice and remember to shave under your arms too."

I blushed as I applied the soap to my pubic area, I wasn't sure I was capable of doing 'a little trim' and so I decided to just shave it off then and there.

"Oh good girl, you may as well embrace this, plus, it will make your penis look bigger if any girl is lucky to get close enough to see it."

I was blushing again as I got out of the bath and towel dried.

After a little more instruction, I stepped into the panties, they were just plain black cotton not very sexy or showy, but the feel of them against my now hairless cock was new and thrilling. I tucked my cock between my legs before it could swell, and put the bra on, then Ms. Graham gave me a couple of small falsies to stuff it with.

"Roll the stockings into a ball with the seam on the bottom of the foot, then slowly roll the stockings up your legs and attach to the suspender belt."

I did as I was told. Ms. Graham made a few small corrections, and then when she was satisfied, I stepped into the maids dress.

"We will work on hair and makeup later, just now, unless someone gets close to you, you look feminine enough to pass."

We went back to Ms. Graham's sitting room where she took a plan of the house from a drawer and highlighted eight rooms.

"The girls are normally out of the house by seven thirty, Monday through Friday these rooms will be your responsibility.

"You will start at eight in the morning and work until twelve, at two you will report to the kitchen, where you will work with the chef until six."

None of that seemed too burdensome.

"At first, it would probably be best if you kept yourself to yourself, lights out at ten."

I nodded and she continued.

"The girls are allowed to bring both male and female friends into the house, they are meant to leave by ten, but this is a hostel, not a convent, we leave the back door open to allow any guest who may have overstayed a little to leave discretely.

"Discretion is very important Geraldine, you see nothing, you hear nothing, and you say nothing.

"If there is a problem, you bring it to my attention, and only to my attention, and do you understand?"

"Yes, Ms. Graham."

"Good, follow me," she took me to the first bedroom on the list and took me through the routine.

Every day strip the sheets and pillow cases, once a week replace the pillows and the comforter, make the bed, hoover the carpets, wipe the surfaces down, clean the inside of the window, once a week clean the outside, empty the trash.

The list of chores went on and on until finally, we were in the bathroom.

Each girl had a black wicker basket lined with a small green canvas sack into which dirty laundry was placed. If I found any loose clothing lying around the room I was to put it in the sack, the laundry was done twice a week.

Clean the bath, the mirrors, the toilet, the upper and under sides of the seat, and the wash hand basin. Empty any trash, replace the toilet paper and restock with shampoo, tampons, and pads as required.

Ms. Graham did the first room in fifteen minutes.

I did the second in close to an hour.

"Do not worry dear," she told me, "you will find that the work comes very quickly to you, and you will end up with more free time than you think is possible just now."

I did the remaining six rooms with Ms. Graham popping in and out to make suggestions.

In between, I ate a quick lunch in the kitchen and was introduced to the chef, a middle age Latina woman named Luz.

Luz obviously liked to taste her food as she went along as she was quite stocky, but she was friendly, and never blinked an eye at the boy sitting at her kitchen table, dressed in a maid's uniform, eating a chicken salad.

I peeled vegetables, boiled water, set tables, anything the chef wanted to be done, I dogsbodied around getting it done.

As the day drew on, I saw less of Chef as she moved around the room, supervising her assistants as they set up their serving stations for the communal meal.

The girls started to congregate in the dining room around five-thirty loudly discussing their day.

Chef gave me a tray with a full meal, roast chicken this time, and a small glass of white wine.

I ate quickly and went up the back steps to my room without anyone noticing me.

A Night Visit

I was lying in bed reading my employee hand book when there was a quiet knock at the door.

I was naked so I got up and opened the door, peering around the edge to see Ms. Graham standing there, I blushed and opened the door to let her in.

I seemed to be doing a lot of blushing today.

"No, no, no, dear, this will not do at all, my ladies do not sleep in the nude."

She opened a drawer and brought out a pair of white panties and a matching nighty, diaphanous and long enough to reach down to mid-thigh, she handed to them to me.

While I was dressing she told me, "You did well today Geraldine, very well, in fact, I am very happy with your work ethic, I feel you will do well here."

I was sitting on the bed in my panties and nighty, "Thanks, Ms. Graham, I'm trying hard."

"I know you are," she smiled at me, "you were very nervous in the bathroom this morning Geraldine, do you mind if I ask if you have much experience with the opposite sex?"

"No, I don't mind, and no, I don't have much experience, any experience really."

"I thought so."

She leaned close to me, and her fingers lightly brushed the front of my panties, I could feel my cock begin to harden at her touch, and the head popped up over the waist band.

Ms. Graham voice was soft, "Excellent."

I didn't know what to do, I was sitting there in girls clothes while this older woman was giving me a raging hard on. Her hands slipped the front of my panties down, freeing my cock, and at her instructions, I lifted my hips and she continued to roll them down to my knees.

My cock was now tenting the front of my nighty, and she leaned in even closer to me.

She kissed me on the lips as her hand began to softly move up and down my shaft. She rolled the foreskin back and forth with each repetition, I'd gasp a little with the pain of it, and the pleasure. She didn't say anything, just kept eye contact with me while her hand slid up and down my cock.

I suspected that it had never been as hard before, certainly not when I was wanking myself off.

Her speed began to pick up, and little slapping sounds echoed around the room as she sometimes hit my balls on the descent.

I knew I couldn't take this for long, "Ms. Graham, I'm going to come."

"Good dear, very good."

She moved her hand more rapidly and I immediately exploded from my cocks' eye into my nighty. She lifted her hand, I could see my semen covering the tips of her fingers, then she slipped them into her mouth and eagerly cleaned them off.

"Ms. Graham. What's going on?"

"I am not looking for a boyfriend dear if that is what you are wondering about," she handed me a wipe to clean myself up.

"You need to relax Geraldine, right now you are just too tense, trying too hard, and that makes teaching you much more difficult."

She left me on the bed to get me a pair of high heels from the closet, shiny patent leather, the heels looked like mountains to me, although they were actually not much more than three inches high.

"Your uniform requires you to wear pumps dear, but a girl needs more ammunition in her locker than flats.

"Each night, for one hour, I want you to walk up and down the corridor in these heels.

"At first, you will be unsteady and it will hurt, but that will pass quickly, later, I will ask you to show me your progress."

"I don't have a watch, Ms. Graham."

"I will take care of that tomorrow.

"For now, there is a clock on the wall outside, use that, remember I do not want you overdoing it and hurting yourself, a sick maid cleans no rooms."

I nodded, put on the heels, and hobbled to the door.

I was walking very slowly, I could feel my ankles ready to turn at any moment, and I had not found my balance yet, but I managed to walk unsteadily up and down the hall for the required amount of time.

I wasn't really focused on the exercise, it had been a strange day. I'd spent it dressed as a girl, and yet I had just finished my first real sex act with a person of the opposite sex. I wasn't exactly sure of what had happened, or why, or what was to come, but I was looking forward to the next day.

Ms. Graham was right, I did learn to clean the rooms much more rapidly, and by the end of the first week, it was only taking me two hours to complete all eight rooms.

Ms. Graham inspected my work and after I had corrected any deficiencies she noted, I made my way to her parlor for further instructions.

"There are many men coming and going around this house Geraldine, if you do not want to be stuck in your room at night, you need to be able to fool them and pass for a girl.

"My other ladies do not need to do that of course, they act instinctively and I just polish their rough edges, but you will need to learn everything from scratch."

She taught me how to sit and how to get up from a chair, how to smoke, how to drink, how to walk.

Everything I did was wrong, masculine, so I watched her, and then repeated her movements many times over.

The most difficult lesson was how to appear relaxed. The idea that I would ever be able to fool anyone about my sex was laughable, but with Ms. Graham's gentle instruction I gradually began to believe in myself, and as I did, the lessons became easier.

Ms. Graham was very much into something called Active listening.

"Men like to think they are the center of a woman's world, active listening helps you to convince him he is.

"If you ask him an intelligent question about the things he is speaking about, he will be drawn to you like a moth to a flame."

I wasn't sure I wanted to draw a man anywhere, but it all seemed to be part of my on the job training, and I assumed her curriculum was directed towards girls. She was a busy woman, she didn't have to teach me these things, and I didn't think she needed to waste time tailoring her course to me, so I kept my mouth shut and showed my gratitude by being an attentive student.

Charlie

The first week had flown by, and then on Saturday night, Caroline stopped by my room. I hadn't seen her all week and I felt a wave of happiness hit me as she came through the door.

"How's it going?"

I was sitting on the bed reading. Ms. Graham had given me a yellow dress that morning as a reward for my first-week successes. My street clothes had not been returned to me so I had decided to wear it tonight, and I stood up and twirled.