My Life as a Maid Pt. 01

She gave me a blue pill to swallow, "Viagra, it should see us through the next few hours."

I wondered if many peoples "First time" was a day's solid instruction in fucking. My cock was swollen and hurting from battering her pussy for so long at the end. Finally, with a lusty laugh, she told me I had two days rest before our next session, but she did not mark my book, so I couldn't surrender my virginity to Charlie just yet.

Learning the Rules

Charlie did join me in bed that evening, but only to hold me and kiss me and just let her love flow over me, was there a better healing potion than that.

I had been warned that my training would be intense, but it was ridiculous.

The maid work was fine, the school work was fine, sex education was fine, each in isolation, but put all three together, and I was running tired.

Charlie came over as many nights as she could, she had been through the process before me and was very understanding of how trying it was.

"Charlie," I asked one night, "why do we never sleep together through the night, and why are we never in your room?"

"It's not allowed Ger when you're promoted to the secretarial pool it will be fine, but Ms. Graham would find it unseemly for me to have a maid in my room or to stay over.

"I don't like it, but that's just the way it is."

I kissed her and let my fingers roll under the edge of her panties to play with her pussy.

"I thought you were tired," she wasn't complaining, just the opposite.

I put my hand under my pillow and brought out my instruction manual.

"She gave me an A," I said.

Charlie let the straps on her teddy fall off her shoulders to either side, she gently rolled it past her tits, down over her hips, her ankles, and handed it to me.

"Like the teddy," she said, "I'm all yours."

I will always remember that night clearly and with great fondness. We made love multiple times, and I grew to understand the difference between using my cock as a tool under Ms. Graham's instruction, and as a vehicle to bring me closer to the woman I loved. Having sex, and making love, two similar, but very different realities.

A New Life

The weeks passed, I grew more confident in my girlhood, and Charlie and I grew more confident with our relationship and each other's bodies.

I was happy, I wasn't sure if I had ever been happy before, but I knew I was now.

Charlie was a senior girl now, she went on dates at least few times a week, but she thought it better that I didn't know anything about them, and I didn't ask.

I was sure I'd be insanely jealous if I knew someone else was sharing those wonderful tits, that juicy pussy. It was probable, but as long as I didn't actually have confirmation, I could fool myself. I knew why Charlie was here, and I knew why I was here, and I knew I had to learn to accept both.

During the days Ms. Graham continued to guide me through my manual.

I was doing well, everything was a flavor of regular sex, with a little light role-playing, and some dominance and submission as the only real deviation to learning to fuck in various positions.

One day I entered her bedroom to find James lying naked on the bed.

I knew this day was coming, but I was still a little startled and even scared when I saw him.

Ms. Graham beckoned me over.

"It is time you learned to please a man, we will start with masturbation."

I complained that I was already expert at that, Ms. Graham laughed at me and then spent the next two hours proving me wrong.

I found myself admiring James' cock as I worked on it, it was really quite attractive, circumcised, large, the skin a few shades darker than his body, it felt soft in my hand, even as he stayed rigidly hard for our entire session.

His control was something I could only hope to emulate someday, he didn't look close to coming as Ms. Graham and I worked on his swollen mass, finally with a word from Ms. Graham, he let a river of white sticky spunk shoot over his belly and chest.

He paused for a breath, grabbed me by the hair and simply commanded me to clean him.

I leaned over his body and let my tongue work its way from the bottom of the stream up.

I had eaten my own spunk from Charlie's pussy many times and I had no trepidation as I started to lick his from his firm muscles.

I had cleaned everything I could see and moved hesitantly towards his cock.

"No," Ms. Graham said, "you are not ready for that young lady."

She handed James a wipe, and he quickly cleaned up, dressed and left.

After James was dismissed we sat in the arm chairs which filled the space in the rooms' bay windows.

Ms. Graham handed me a cup of tea, "So dear, what are your thoughts?"

"I thought I'd be more awkward, more scared, unsure of myself," I replied, "it helped that I'd seen James naked before, and it was just a flash of panic when I walked through the door, no urge to flee."

I took a sip of my tea, "Once we started to work on his cock, and I could see the pleasure on his face, it was rather exciting, powerful, I was surprised at how quickly I was fully committed, but I was fully committed."

Ms. Graham smiled at me, "People say woman are the weaker sex, and perhaps in many ways we are, but a woman who knows how to bring pleasure to a man in bed, always has the upper hand, she has the control, she has the power.

"Do you remember our lessons on dominance and submission?"

"Yes, Ma'am."

"It does not seem so, but the submissive has as much power, maybe even more than the dominant.

"She can end any session with the simple use of a safe word, his dominance is only at the limits of her forbearance.

"It is the same with regular sex, even when lying under him with your legs spread wide, you control the situation as long as you have the will power to do so.

"It is an important lesson Geraldine, do not forget it."

Commitment

Charlie was sitting on my bed when I returned to my room, she looked delightful, she wore a yellow summer dress, a sunflower pattern, her favorite flower.

I knew the flow of her body well now, and I was fairly sure she had decided underwear was superfluous today.

"Hi, Love," I said cheerfully.

A bridge had been crossed as I played with James cock, as I fully committed myself to a sex act with another man, I knew I had fully committed myself to Charlie too.

She got up and pulled me close, kissing me, then pulled me down on to the bed with her, "I need to tell you something," she murmured.

That sounded a little worrying, I only nodded.

"You know I've been dating," she continued, "well one of the guys has asked me to be his girlfriend, exclusive.

"He's nice, I like him, not the way I love you, but I want to say yes to him."

I smiled at her, as wide as I could.

"I knew this time was coming Charlie, say 'Yes,' it's the right thing to do for us."

I thought this was the bravest thing I had ever done, my stomach was turning as I set my heels against a wave of jealousy.

"I'd like to meet him sometime."

She leaned in to kiss me, "Thanks, love."

Her hand reached my cock and freed it from my panties, my hand found her pussy, as I expected, naked under her dress.

In minutes we were naked, I bent her in front of me and entered her from behind, my initial thrust was deep, angry, and she moaned in surprise and pain as I threw my cock into the depths of her pussy.

I didn't hesitate, I withdrew almost the entire length and quickly battered it back into her. Her pussy grasped my cock when I was inside her, not to slow it, but to show her love by adding to my pleasure. I'd never fucked her angry before, but I couldn't help myself this time.

She leaned forward, pushing her head into the pillows giving me a better angle to fuck my frustration away.

She took everything I had, the room resounded to the sound of her ass being slapped by my thrusts, I never said a word as she lay under me panting with exertion.

"Jesus hon, I'm coming," I moaned as I filled her.

She slid out from under me and I collapsed onto the bed, her hands played lightly with my neck, and I turned to face her.

"I'm sorry," I said, "I guess I wasn't as free of jealousy as I thought, but I shouldn't take it out on you."

She smiled at me, "I know, I really didn't mind, I know we'll be fine, anyway, I liked it.

"You should be more forceful more often.

"You might wear panties around here, but you're still the man in my life, I like it when you take charge."

Afterward, we made love well into the small hours of the morning, it was against the rules, but I woke to her in my arms for the first time, she kissed me, dressed and walked back to her room.

There was no point hiding her over stay, the house was already awake, and Ms. Grahams network would soon let her know of our transgressions, it was against the rules, we might get punished, by damn it, it was worth it.

Punishment

I didn't know if this was my regularly scheduled lessons or punishment for spending the night with Charlie, but the next morning I gave my first blow job, and then so much more.

I spent hours sucking on James cock, he came so often, I was sure my full stomach would reject the next load of spunk I had to swallow.

I spent four hours pleasing him, at the end I was a mess, covered in sweat, his spunk, my own spunk, my jaw was agony, and my tongue felt like it had been sandpapered down to the taste buds.

"Good girl Geraldine," Ms. Graham said from behind me, "You have an hour to clean up, eat lunch, then meet back at my study."

Charlie was waiting in the hall outside the study door when I arrived, her finger went over her lips, and she pointed for me to stand beside her.

We waited for at least ten minutes, the hallway seemed colder than normal.

I wanted to ask her why she wasn't at work, what was going on, I wanted to hold her hand, but her eyes flashed me a warning and we waited beside each other.

It was isolating, lonely.

Ms. Graham opened her study door and invited us in, "Stand at the line, no talking."

She had taped a line in front of her desk with yellow masking tape, I'd never seen that before, and I was certain it had been done very recently.

"You broke house rules last night, Caroline, you know as a senior girl you cannot overnight with a girl whose status is not equal to your own."

"Yes, Ms. Graham," she answered.

Ms. Graham pointed to her desk.

Charlie leaned closer to it, grasped the edge with her hands, and bent over, her back at ninety degrees to her legs and parallel to the floor.

Ms. Graham lifted her skirt and pinned it to the back of her shirt, she then pulled her panties down to her knees displaying her lovely ass.

Ms. Graham lifted a cane from her seat and without warning it swished through the air, landing on Charles beautiful ass, leaving a thin red welt to form across both cheeks.

"One, Miss," Charlie said.

The cane landed again, "Two, Miss."

When she cried out, "Six, Miss," her tears were in full flow, and she could no longer contain her sobs.

"Stand in the corner until you have yourself under control Caroline."

With her panties still at her knees and her skirt pinned up, she waddled over to stand in the corner.

I could see the six distinct red lines decorating her ass as she struggled to contain her tears.

Ms. Graham looked at me, shit my turn.

"You are not innocent in this Geraldine, but you are not fully culpable either," she gave me a stern look, I'd never seen this side of her, "you will not be canned today, but you must be punished."

I waited apprehensively, "You and Caroline and forbidden to keep company for seven nights, you may leave."

I left with Charlie still standing bare assed in the corner.

I so wanted to speak to her, but Ms. Graham had scared me silly, seven nights, it would feel like seven years.

Charlie and I had started back without a pause, we never spoke about her punishment, and the lines on her ass had almost completely faded by the time I got to inspect it.

My book of instruction was quietly filling, and it was a few weeks later when Ms. Graham invited me over to afternoon tea again.

"Well Geraldine, the pool received a resignation today, another marriage made in heaven."

Although her tone of voice was light I could tell Ms. Graham was serious.

"In two months' time there will be an open secretarial position, the job is yours if you want it?"

I considered that.

This is what all the training had been leading up to, what all that hard work had been for, would I turn my back on it, or accept my fate?

Ms. Graham continued, "We have reached the Rubicon, it is time for your final decision, you must give yourself to a man, willingly, fully, or you must leave the hostel."

I knew this day was coming, I was, of course, worried about it. I'd spent working weeks on James' cock, but I still didn't consider myself as in anyway gay.

I dressed like a girl, I acted like a girl, that is what girls did, tease men's cocks, but I didn't have a pussy, the only thing I had was my ass, and once that was full of cock, I knew I couldn't fool myself any longer.

Charlie and I had many long talks about this question and what my answer would be, it was the turning point not only for my time here but for our relationship, the issue really wasn't in doubt, not considering our other circumstances.

Her boyfriend's name was Dave, he was a little older than her, maybe in his late twenties. He wasn't handsome as such, but he was pleasant to look at, he dressed well, he was going places in the company, and most importantly he treated Charlie well.

He had stayed overnight the previous weekend, and I cried myself to sleep knowing my Charlie was giving herself to him so very close to me.

"I'm ready Ms. Graham, I've been ready for a while, to be honest."

Getting ready

She laughed, "You will need to wait a little longer Geraldine, while I am glad you have made this choice, you are not quite ready yet."

She took a butt plug from her desk, it was about half the size and width of my own very average cock, "Bend over the desk, step out of your panties, and spread your legs wide dear."

She poured a generous dollop of lube onto her hands, and I felt the wet warmth as she slipped a finger inside my tightness. She worked the finger gently in and out, applying more lube as she went. I'd never been finger fucked before, the sensation was driving me wild, although her finger was slim the feel of it as it slipped to and fro was like nothing I had ever experienced before. Soon a second finger joined the first, I felt my hole widen to accept it, and then it did the same as a third finger joined in the action.

I was very pleasant, my cock hardened underneath the action of her hands.

"Breath in dear," she told me, as I did, she slipped the butt plug into to my ass, seated it, then wiped me clean.

I stood and redressed myself at her command.

"You will wear this for a week, it will stretch you a little way. Each week we will increase the length and girth until I think you are ready for a real cock. That way, when the time comes for you, losing your virginity will not be unpleasant or painful."

Ms. Graham pointed to an armchair, and I sat as she poured another cup of tea for each of us.

"Losing your virginity, allowing a man to penetrate you, is a momentous occasion in a girl life. There are some choices available to you."

I went to speak, she must have read my mind because she quickly interrupted me.

"No Geraldine, it cannot be Charlie, it must be a real man, with a real cock.

"You girls will have plenty of strap-on fun with each other after I'm sure, but only after I have decided you are advanced enough in your training."

She continued, "First, many men will pay handsomely to be your first, I can arrange it, and all the money would go into your savings account."

"That sounds very tawdry Ma'am, no, thank you."

"I would have been disappointed if you had chosen that option, money is not everything.

"Next, you have been isolated here and have not made any new male friends, so that does not add to your options, but is there anyone from your old life who interested you?"

"No, Ma'am."

"Hmmm, then the girls could take you to a particular club we know well, dancing, drinking, over the course of a few nights, I am sure you would find someone acceptable."

"I've never been very good in clubs Ma'am, being a girl has liberated me, liberated my libido, but I'm not sure by that much."

"Well," Ms. Graham said, "The last choice, I could pick someone for you."

"Is James allowable Ma'am, I'm sort of used to him and his cock by now."

She laughed, lightly, but very pleased.

"An excellent choice Geraldine, he is allowable, and he will be very pleased that you have chosen him."

Ms. Graham spent the next hour giving me advice on how to act during the occasion.

I listened intently and then left.

The feel of the plug inside my ass was strange, and while I had gotten used to walking in heels by now, I found making my way to my room a little bit of a struggle.

Charlie had my panties down and bent me over the bed as soon as I told her I had been plugged.

She squealed with delight, and let her fingers lightly tap the end of it, sending a new and pleasant feeling through my ass.

"Oh Gerry, not long now, not long, for both of us."

She insisted on being on top when we made love that night, as her hips met mine, the butt plug moved.

I had the always lovely feeling on my cock in her pussy, and the new, and strangely warm feeling of a plastic cock in my ass only added to the pleasure, I couldn't contain myself that night and I came fast and frequently.

She left me in bed some hours later too exhausted to murmur anything except, "Night love," as she gently closed my door.

Ms. Graham was true to her word, each week a larger plug replaced my current issue, I quickly got used to it, and she was delighted with my progress.

The one strange thing was I hadn't seen James at any of my lessons since I had requested his services for my defloration, I assumed this was to build my anticipation for the big night.

Once, and for the only time ever at the house with her, I sat naked in bed with Ms. Graham watching porn, gay porn.

She was playing with my cock the whole time, but I knew it wasn't necessary, I had accepted my dual nature, and I was excited watching it, I would have been hard the entire time anyway.

When it was over, she turned her ass towards me, wiggled it, and spread her pussy lips wide.

I slipped inside her and vigorously fucked her doggy style for a few minutes, after I exploded inside her she smiled at me, "I think you are ready dear."

Virgin

The guest suite at the Hostel was lovely, on the top floor, one wall was a huge bay window, which overlooked the park.

The décor was tasteful and understated, I didn't know any of the pictures hanging on the wall, but after closely inspecting one, I realized they were all originals.

There was an oversized king size four poster bed, a matching couch and love seat in a matching dark blue brushed sued, a large dining table, a sturdy coffee table. Plenty of opportune places for a little judicious fucking I thought.

I was standing at the window, a white silk robe covered a white lace baby doll and matching G-string, white hold up stocking and white patent leather six-inch heels completed the ensemble. I wondered if I had over done it with the virgin metaphor.

I was drinking a glass of champagne when the door opened behind me.