My Life as a Maid Pt. 01

"I'm feeling very strange, I mean, I look good in this, and I feel good in it too, but it's not quite right, is it?"

She laughed, "To be honest Gerry, I'm glad to see you, I thought you'd last a couple of nights at most, get some sleep and some food, then bail out the back door.

"No one would have stopped you."

"Maybe that's why Ms. Graham hasn't given me my old clothes back."

"I doubt it," Caroline sounded a little hurt, "Ms. Graham is very straightforward, why don't you ask her?

"I hope she burned them, they were disgusting you know?"

"Oh I know," I paused for a while.

"I don't need them anyway, I'm going to stick this out for a while, I've not felt very safe recently, I've nowhere else to go, and this," I said holding up the hem of my dress, "is a small price to pay."

She sat on the bed beside me and gave me an odd look, she leaned in close to me, her hand resting on my leg

"Kiss me."

"What!"

"Kiss me you moron, you should have done it in high school, years ago, I don't know how many signs I gave you that you didn't notice or you ignored, it was all very frustrating."

I was staring at her google eyed.

"Are you kidding?"

"Nope, so did you want to, kiss me that is, back then?"

I giggled internally, "Yes, but I thought I was just friend material.

"I was too nervous of rejection if I crossed the line and you didn't respond to me."

"Dolt," she sounded just a little sarcastic, "now's your chance, kiss me."

I leaned in close to her, I'd never really made out with a girl before and I didn't have a clue about what I was supposed to do, but she helped me over the initial hump of insecurity and we started to kiss.

Kissing came naturally, who knew?

I decide to be a little more adventurous, and my hands brushed across her ass, she didn't stop me, it was rounded and firm to the touch. I let my fingers wander up her back, then around to lightly brush the material of her bra, over her blouse.

She undid her blouses top buttons, and I felt skin under my fingers.

I wanted to undo her bra, see her boobs, feel them, kiss them, but I didn't want to break the mood by trying, struggling to undo it, and ultimately failing.

Sometime later she broke the spell, "That's enough," she said breathlessly.

She had ended on top of me as we rolled around the bed, she must have felt my hard on under my dress as it pushed against her, and as we sat up, I blushed.

"It's OK," she said taking my hand, "let's not rush things."

I nodded as she got up.

She gave me a quick peck on the cheek and with a cheery, "Later," left the room.

I was sitting there in a yellow dress, having just had my first make out session with a real live girl, so what was I going to do with this hard on? I slipped my panties off, pushed my dress up and let my hand do its work on my cock.

My fantasies were a mixed bunch as I worked away on it.

I was in the man's position, then I was in the woman's, it was all confusing, but sexy as hell, and I soon shot a stream of hot spunk onto my belly. I lifted my fingers to my mouth and cleaned them in the same fashion as I had watched Ms. Graham do, the taste wasn't that bad and I wondered why I had never tried it before.

Caroline came back on Sunday morning to ask if I wanted to have tea on the patio. She said she had cleared it with Ms. Graham, who thought it a great idea, as she was pleased with my progress and thought I was confident enough to start being seen around the house.

We sipped our tea and held hands under the table.

Caroline explained that all the girls in the house worked in the secretarial pool for a large finance company.

"Do they still have those?" I asked.

"Not in most places, but this company has a CEO with some strange ideas.

"It's all very sexist in a modern context, but he wanted not only efficient secretaries and PAs but ladies steeped in company culture, who have potential as wives for his younger executives.

"We're all here by our own choice, but it feels like a shark tank at times.

"Some of the girls are very ambitious and have their eyes set on this or that man, and Hell mind the girl who gets in their way.

"All the girls in the pool live in the hostel, it's a condition of our contract, one of the reasons for that is contact with Ms. Graham who teaches us life skills, work skills, other stuff."

She paused for quite a long time.

"You know, in bed."

I was staring at her, her revelations were unsettling, not so much because of their content, but because I'd been here a week, and never really asked any questions about the place.

"Does it work?" I asked.

She nodded, "It seems to, in the last year, quite a few girls have married into the company, only two have left the hostel to find employment elsewhere."

Damn, I thought my life had become strange, but Caroline's sounded even stranger.

"Do you have your eye on anyone Caroline?"

"Call me Charlie, all my close friends do, and no, not at the moment.

"I did like one guy, but it didn't work out."

She went quiet and I didn't want to break the silence, so I simply squeezed her hand.

That night I dreamt I was a high powered executive, with Charlie sitting on my knees taking shorthand, her panties at her ankles while I fingered her pussy. I definitely needed a shower before work that morning.

Training

I finished my rounds at ten thirty, changed into a tight tweed skirt, and sheer white blouse under which my black bra was visible, put on six-inch heels, then proceeded to walk up and down Ms. Graham parlor floor as she gave me instructions on how to feminize my gait.

"Swish your hips a little more."

"Point your toes."

"Lengthen your neck, chin up dear."

"Turn smoothly, do not rush it."

After my lessons I was invited to sit, leg crossed at the ankles, knees bent away from where Ms. Graham was sitting, a cup of tea on a saucer before me.

"Did you and Caroline have a nice afternoon dear?"

"Yes Ms. Graham, I must admit I was a little worried at first, but no one seemed to notice I'm a guy, or if they did, no one said anything."

"And did she explain the purpose of the hostel to you?"

"Yes, Ms. Graham."

"The things I am teaching you, I have taught all of them, but there are other things I teach them too, did Caroline explain that?"

"Bed Skills?" I inquired.

"That is one way of phrasing it, you are very inexperienced in that area Geraldine, I can help you with that if you would like.

If you really want to learn more, be at my bedroom door at seven tonight."

I answered, "Thank you, Ms. Graham," rose, settled my skirt with a quick draw of my hand across my ass and left.

Sex education!

After my fears, and my failure to at least attempt to undo Charlie's bra, that sounded like a great idea.

I couldn't concentrate very much during the rest of the day, and the hands of the clock dragged their way around the face until it was seven. I was waiting outside her door exactly at the appointed time, actually, I had been hiding in the stairwell for at least fifteen minutes before it to be sure I wasn't late.

Ms. Graham opened her door, she was wearing a striking red silk kimono, the hem of which hardly reached to the end of her butt, flashing me just a little of its naked flesh.

"Come in dear."

Her bedroom was entirely different to the parlor where I usually met her. It was very modern, the furnishing, the art, the accessories. I assumed the parlor was furnished by who ever owned the hostel, but this room was to her taste. The furniture was a dark wood, Espresso, the hardwood floor was much lighter, and the walls and rugs a silver/gray color. It was very well done, and obviously expensive.

Behind me, I heard a soft rustle of material.

"Turn around," I heard from behind me.

Ms. Graham stood there totally naked, the kimono pooled at her feet.

"Look at me," she said as she raised her arms and slowly turned in a circle before me.

I'd say she was around forty-five, but her body was still slim and taught, she had alabaster skin which made the dark hair which rolled down her back seem even blacker. The mounds of her breast were a perfect complement to the mounds of her ass, she had a small runway of black hair pointing to her pussy, and not a single hair elsewhere on her body.

She was the first real woman I had seen naked, and she was specular, my cock sprung to life, hard from the sight of her.

She looked at me, obviously staring at my groin and the tent in the front of my dress.

"That is quite a compliment, Geraldine, undress please."

I was excited, but I remembered my lesson and undressed in the proper order, folding my clothes neatly over one of her chairs, soon I stood totally naked. My cock was pushing out from my body with excitement, the purple head glistened with the wetness of my precum, and my foreskin had already rolled back, the purple veins which littered its length where a junkies dream, pulsating, high and obvious, it was quivering like a strummed guitar string.

Ms. Graham took my hand and led me to the King Size bed which dominated the room, I sat on it as she lay back on some pillows.

"We will get to the practical demonstration soon dear, but the first lesson is nomenclature."

She started from her head, pointing out the erogenous zones and pleasure point on a woman's body. She named the parts of her breast, made me repeat it, then I was allowed to touch them as I repeated the name again. She spread her legs bringing her knees back as she fully displayed her sex, then she did the same with her pussy.

My fingers trembled as they lightly lay on her clitty and she softly sighed. I touched her lips, her vaginal opening, her ass, satisfied that I could identify each of the parts properly, she announced the start of our practical lesson.

Everything I did, she told me to do, and I did it exactly how and when she told me to do it, that only added to my excitement.

I placed a little lube in the pool of my hand, rubbed it to warm it up, then let my fingers lightly drift over the hood of her clitoris. At her nod I exposed the glans and began to massage the button, I varied my stroke, fore, and aft, round and round, she was beginning to breathe a little harder, I could see some sweat form on the inside of her thighs, and her vaginal opening was getting wetter.

I practiced fingering her clitty for perhaps fifteen minutes, then I began to work her nipples, all the while her soft voice instructed me, telling me when to apply more pressure and when to slow down.

My own cock was rigid through the entire process, I was sure I'd never had a hard on last that long before.

I then started to mouth her tits, first the left, then the right, work the nipple, work the mass, use my hand on the other, coordination didn't come easy at first, and often I had to stop one action while working on another.

I started on her beautiful body, kissing and licking all the way down until my head was between her legs and I was once again starting at the lovely pinkness of her pussy.

I let my tongue dart out to touch it, lightly, very lightly, then I moved closer. At her instructions my tongue mimicked the actions of my fingers, her pubic mound began to buck into my face very gently, and her hands grasped my hair pushing me closer to her.

I worked her sweetness for perhaps five minutes before she groaned into orgasm. I closed my eyes as she squirted covering my face, then I licked my tongue around my lips, savoring the various new flavors I was being treated to.

"That was very good for the first time dear," she told me as her hand wrapped itself around my cock, she slipped me onto my back and began to masturbate me.

My cock was exceedingly sensitive, it had remained hard through the whole session and it only took a few strokes to make me come.

Somewhat embarrassed I opened my eyes.

"Premature ejaculation is nothing to be worried about Geraldine, it is easily cured, but always remember to tell a girl when you are about to come, especially if you are having oral sex, some like the taste of cum, some do not, some like its feel on their face, some do not, but it is always their choice on how they will receive your load."

"Yes Ma'am."

"Get dressed Geraldine, that is enough for tonight, come back tomorrow."

Pleasing Charlie

My days were passing quickly now, I spent my morning doing maid work, my afternoons in the kitchen, and every free moment reading about and being instructed on the proper mannerisms of a lady.

Oh, and learning more and more about sex.

Ms. Graham had an encyclopedic knowledge on the subject and an easy way of instruction.

Our home didn't have the internet, Dad didn't believe in it, "Satan's Trap," he called it, and so unlike most of my class mates, I hadn't grown up watching porn and I didn't really know much it.

I certainly I had no idea about fetishes.

Ms. Graham broached the subject of cross dressing with great sensitivity.

I wasn't really going to deny my feelings on that subject now, no matter what happened in the future, I had worn my last pair of boxers, I was a panties guy from now on, they just felt better.

I wondered what Dad would have said to that.

Ms. Graham taught me how to put a condom on, and how to take one off properly after it had been used.

At first, I didn't mind the feel of it, it was different, exciting, but as we were still restricted to masturbating during my lessons, it seemed a bit of a waste of material.

One night I wrapped my panties around my cock, those felt much better than the condom.

After I finished, I considered getting a fresh pair to wear, considering Ms. Grahams rule about sleeping naked, but after I came, I decided to put them back on. Their wet and sticky feel felt deliciously dirty as it wrapped itself around my body, and I was hard again almost immediately.

Charlie visited again that Saturday, we were lying on my bed talking about each other's week in between bouts of breathless making out.

I was telling her about my sex lessons when she lifted her hips and pulled her panties down and off her legs. She began to roll the waist band of her skirt around itself, and soon, her short skirt had been drawn high enough that I could see her pussy. Her blonde hair was very light so she looked almost hairless, but there was indeed a well-shaped triangle of pubic hair just above her pussy.

She lay back and spread her legs, "Show me," she ordered.

I didn't have any lube in the room, so I spit into my hand and wet my fingers, then as Ms. Graham had taught me, I teased her clit and began to play with it.

Her breath began to deepen I allowed my fingers to become a bit more forceful, a little harder action brought her first sighs of pleasure, I had worked her for only a few minutes when in a husky voice she commanded me to use my tongue.

I put my head eagerly between her legs. I could see the flesh of her thighs strain as she pushed her legs open to their widest extent to accommodate me. I sucked on her clit for a while then made her back arch as I gently let my teeth nibble on the nub. I let my tongue slide down some more, two fingers slipped into her wet opening and my tongue slid in between them.

She was thrusting her hips forward in an easy rhythm, and her hands rolled my hair around her fingers. She dropped her blouse to the floor, and thankfully undid the clasp at the front of her bra, allowing both cups to fall to the sides.

I slid up her body to take her tits in my mouth. I had my thumb on her clit, two fingers in her pussy, and as I bit down on her nipple, I let my pinky slide into her ass.

She cried out, "Don't stop, don't stop, you're going to make me come."

I let my hand work her furiously while my mouth covered hers and our tongues met, soon I felt her body tremble, then as she came, she pulled my hand away and rolled over on her side gasping.

She was facing away from me, so I lay alongside her and pulled her body closer to mine.

"Thanks, honey," she said as I wrapped my arms around her.

In a few minutes, her breathing returned to normal, her body cooled and I could see her shiver.

"You're cold, get under the sheets."

"I'm not cold," she told me, "it's just the way I come down," her hand had wrapped itself around my cock and she was slowly playing with it.

She kissed me on the cheek, "Thanks, Gerry that was good, very, very good."

I smiled at her, "My pleasure, it really was Charlie, I thought I was going to come just watching you come."

"Stand up," she told me.

I did and she slipped off the bed on to her knees, her hands grasped the band of my panties and they ended up thrown on top of the bed, I dropped my dress to the floor and stepped out of it, totally naked.

"A lady never leaves her partner unsatisfied," she told me.

Her tongue flicked out, snake like to touch the throbbing purple head of my cock, she traced the veins which stood out on it, then sinking farther back on her knees she tongued the underside of my balls.

I could see my cock quiver as her mouth moved around it, she blew soft slow breaths on to it, she let her moist tongue dart in and out, her hands grasped the width of my shaft, then she opened her mouth and stuffed the head inside.

She didn't move at first, just kept my cock steady within her mouth while her tongue worked every square inch of the head.

She took a deep breath through her nose and bobbed her head to take half my shaft in, she withdrew, took another deep breath and dove down on my shaft again. She had almost my entire length inside, she drew back again, and then I could see her apply a little extra force as her lips finally touched the base of my cock.

I had never even kissed a girl before Charlie, now I was receiving my very first blow job.

Charlie was working my cock with gusto, and her hands caressed my ass pushing me towards her open mouth as she sucked on me.

"I'm coming, Charlie."

She brought her mouth off and her hand quickly finished me.

My cock was pointing at her exposed tits as a thick river of come shot out and landed on them, I spasmed another few times, smaller amounts of cum flowing out each time, there was little force left by at the end and some of my shot landed on the floor.

"We'd better clean up," she said.

I handed her some wet wipes to take care of my come covering her tits, while I worked on cleaning the floor.

She asked for some more wipes and cleaned her pussy, then leaned over and started to clean my cock, she noticed it stir in her hand.

"Not a good idea right now, I have to go," she said, "perhaps you should clean yourself up."

"When will I see you?" I asked.

"Wednesday maybe, if not, we can spend all day Saturday together."

She left behind the scent of her pussy, mixed with our come and our passion, I lay back luxuriating in it, dressed for bed and fell into a deep sleep.

An Offer

Some weeks had passed and I had no problem with my maid duties now, I was fairly confident that most people who looked my way, would only see a girl busy at her work.

Ms. Graham agreed and took the time to introduce me to the other girls who worked around the house, later I was invited to her study for afternoon tea.

I was sitting on a comfortable arm chair facing her, she explained some more about the unique features of the hostel, and why she had decided to introduce me to the other girls that morning.

The girls who worked as maids were waiting for a position to open up at the insurance company, as one of the senior girls got married they would leave the hostel, and then the senior maid would be promoted to junior secretary.