My Life as a Maid Pt. 01

I understood the pattern, Charlie had already told me about her time working as a maid. For some reason, I felt better knowing that she had been in the same position I was now in, well almost the same position.

"Where does that leave me, Ms. Graham?"

"Tell me Geraldine, have you ever been with a man, ever thought about being with a man, wanted to be with a man?"

"No Ma'am."

I was shocked that she had asked me that question, I was sure she knew what Charlie and I were up to, so I thought that came from left field.

I hadn't been one hundred percent honest with her, I knew that, but I didn't feel like correcting myself either.

"There is a certain mystique to being a girl Geraldine, even when only role playing one, you can get caught up in those feelings.

"It is deeper here, more reinforced.

"My girls want a man, it is a product of their training, sure some girls still like other girls, but we all feel the need for a man at some point in time.

"I watch you grow more like a girl by the day.

"You look like a girl, you walk like a girl, you act like a girl, you even sound like a girl, it is absolutely captivating to watch.

"But if you immerse yourself much further into this role, you will want to be with a man one day, you will not be able to help yourself, and you will either need to quit the hostel, or prepare yourself for that eventuality."

"I'm not gay Ma'am," I spluttered.

"How do you know?

"You were sexually repressed when you arrived here, you had never been with a girl, never been with a man, so you cannot really know the totality of your sexuality desires yet, can you?"

She poured more tea as she continued.

"You have not even asked me for your men's clothing back."

I looked at her inquisitively.

"They are in the cabinet beside the back door, if you decided to leave you will be able to walk out as a man if you choose.

"There is also a small bonus, in cash, which should help you through the first weeks outside, although I do hope you would come and see me before you leave us."

I was thinking of Charlie, "I don't want to leave, not now."

"And you do not have to dear," she told me, "your choice will only have to be made, once you are a senior maid and a secretarial position opens up, and that will be some months from now."

She was looking at me intently, "Unless of course, you choose to advance things early."

"I still don't understand miss, if the secretaries are looking for husbands, and the executives are looking for wives, how I could fit into that environment?"

Her laugh was friendly, "You are still terribly naive dear.

"There are men who have little interest in girls, you know that of course, but a senior executive must have a wife.

"Most women are not willing to commit to a life of celibacy, to a gay husband who has no real interest in them as a sexual being, even in exchange for a life of luxury.

"And that is what would be required from them, celibacy, there can be no gossip, ever, such a woman would never be allowed to take a male lover."

"Are you telling me that?"

"Yes Geraldine, a few 'girls' who have graduated from this hostel have a little more under their skirts than most people would guess.

"Although normally the situation has occurred when a gay couple has been sent to me for help."

I waited while she took a sip of tea.

"I can train you in that way of love making too dear, but I want you to think about something very carefully.

"In our environment, there is no gossip around a married woman and her female social circle, you see, it does not threaten the men's masculinity, and therefore it does not matter to them.

"That means your relationship with Charlie would not draw any attention, as far as our world is concerned, it would just be two female companions who like spending time together.

"Think about it dear, and if you ever want my help, let me know."

I wondered if our conversation was a catalyst to her thoughts because the next day I was excused duties, and Ms. Graham escorted me to the company salon.

After a brief discussion with the stylist we agreed on a long Paige Boy haircut, we kept the color dark but added a little red highlight.

I had my first manicure and pedicure, I choose to have my nail polish match my hairs highlights. I really liked how nice they looked, feminine, pretty, and the total opposite to the grungy mess they had been when I had walked through the hostels front door.

I didn't enjoy the waxing, although every pore of my skin felt a little sexier when it was over.

The technician didn't blink an eye lid as I took my panties off, just smiled at me.

"First Time," she said, "don't worry, I'll be gentle."

After it was over, I concluded that she lied to me, sadist.

Ms. Graham did not agree with sunbeds, so after a one hour massage, we ended the day relaxing on loungers by the pool, sipping on long mixed drinks.

"You look absolutely ravishing Geraldine," she told me.

The Shopping Trip

It was Saturday morning and I was standing outside Ms. Graham's study, the door opened and Charlie stood smiling at me and invited me in.

"You are doing very well Geraldine, you have earned a little credit," she handed me a plastic card, "this is a corporate credit card, Charlie will take you shopping."

She turned to Charlie, "Macy's, Abercrombie, Victoria's Secret, I think, clothes, lingerie, some perfume, body wash, makeup, you know what she needs."

"Yes, Ma'am," we said in uniform and smiled at each other.

"If you think you will go over three thousand, please call me, it is not a problem, but I will need to call Visa to authorize it."

Charlie responded as I was stunned.

Three thousand, my family had maybe spent a tenth of that on me at one time, and then only at Christmas.

"Now ladies, scoot, I have work to do."

We took a taxi to the mall and started at the North end.

As we walked, we talked.

"Why were you waiting for me in Ms. Graham's study?" I asked.

She held my hand, "Let's talk about that over lunch, shopping first."

We were like kids in a candy shop.

I loved Macy's. Jacket, Dresses, Skirts, Blouses, sexy but classy, I went with Bulgari for my perfumes and Macc for makeup.

The bill was toting up rapidly, but Charlie kept a sub total on her phones calculator, and we still didn't have to call home yet.

We did more shopping in Victoria's Secret, Charlie bought me a few items from Fredericks of Hollywood.

"Keep them wrapped for now," she told me.

I nodded and added them to my loot.

We were in Rue 21 when Charlie's hand held a blue denim skirt over the top of the dressing room door.

I tried it on, when I looked in the mirror I squealed, I opened the door and peeked through.

"I can't wear this Charlie, you can see my panties."

She laughed, "That's the point Ger, that skirt will come in useful one day, trust me," she gave me an outrageous wink and we both laughed.

Our shopping list had every item checked off and we were still below our limit, so we headed to lunch.

After our main course arrived I leaned into Charlie.

"So," I said, "you have something to tell me?"

She looked into the distance, composing herself.

"Ms. Graham wanted to know about our relationship," she looked at me, "she was setting the limits of what we can do with each other," there was a long pause, "in bed."

"Oh," I blushed.

"I'm not a Virgin Ger, I'm far from a virgin, but you are, and Ms. Graham doesn't want me causing any problems in your training by giving you bad information."

I squeezed her hand under the table.

"I loved a man once, I gave him everything, opened every inch of my body to him, but he wanted to go down a road I didn't trust him on."

"Can you tell me about it?" I asked her very softly.

"Bondage, Whips, Tattoos, ownership.

"I didn't like the sound of it, and somewhere in the back of my mind, I knew I couldn't trust him but I'd convinced myself I loved him, so I put off his demands, hoping he'd let the issue go.

"He didn't, and when I said no, he dumped me and left me a wreck.

"That's when Ms. Graham found me and brought some stability back into my life."

"Is that why you stopped that morning in front of the bank?" I asked her.

She laughed a little, "A bit, I suppose, but I did have a thing for you in high school, remember, and you never made a move on me, you still intrigued me."

I took a deep breath, "To be honest Charlie if I hadn't been wearing my nighty that night, I'm not sure I ever would have made that move, even after you asked me too."

I let my hands move up and down in front of me.

"There's something about this, which is incredibly liberating."

Her fingers made light circles on the inside of my thigh, it was under the table so no one could see her, and I opened my legs a little more for her.

"And sexy Ger, very sexy."

She leaned in to kiss me, and I returned her kiss.

"About those limits love?" I asked.

"Soon Ms. Graham will give you a book, in it, there will be a list of sex practices, positions, techniques when she is satisfied you have mastered each one, she'll mark it up.

"We can't do anything new until that mark is in the book, but once it is, we are free to run wild."

"Do you have a book, Charlie?"

She nodded, "Mine is complete," she took a drink.

"I'm about to become one of the senior girls, I'm getting noticed, more of the executives are giving me admiring little glances, and I'm already receiving invites to dinner.

"The way that works in the company, I'll probably be married within a year."

I looked at her shocked by the news and I thought I was going to cry.

"I told Ms. Graham, we are serious, we are, aren't we?" She asked me.

I had started to cry, just a little.

"Of course we're serious, I love you."

I had never told anyone that I loved them before, and she leaned over and kissed me again.

Charlie looked at me, her eyes very serious.

"If we both end up married to executives, we will still be able to be best friends if you know what I mean.

"Our only other choice if we want to stay together, is to leave Ms. Graham and the hostel.

"I remember the state I was in when she found me, frightened, an emotional wreck, and I'm too scared to go back there again.

"I'm sorry Ger, I love you too, but I can't leave, it's too scary out there."

I sat back, my thoughts were racing in every direction.

"Ger," she shook my shoulder very gently, "Ger."

I came back to the present.

"Sorry Charlie, it's a lot to take in."

She gave me time, holding my hands while I composed my thoughts.

"I want to be with you Charlie, forever, I love you.

"I've never loved anyone before, and I can't lose you, but do you know what it means, for me to stay, to eventually marry like you will, into the company."

I finished my drink and ordered another, "I'm not sure I can do it, but I'm willing to try."

She nodded, "I shouldn't ask you to do it, but I can't stop myself, I love you too much."

"Can we handle it?" I asked, "Can we be at peace with the thought of us with another lover?"

"I can handle the idea of you with Ms. Graham just now," she was very firm, "I know it's not exactly the same, but if we can compartmentalize our feelings like that, I think we can do it, I want to at least make the effort."

I kissed her, "I think I have an offer I need to discuss with Ms. Graham."

And So It Begins

When we arrived back at the Hostel I was informed I had a new room. No longer hidden at the back of the building, I was now in the same area as all the other maids. My room was much bigger, with a twin sized bed.

We emptied my packages and put them away, I asked Charlie to set up a meeting with Ms. Graham for me, then we spent the next few hours making out and sixty-nineing. Charlie snoozed in my arms, and I realized I had never been happier.

I had finished my chores, and yet again was standing outside Ms. Graham's study. I entered at her call, and she poured me a cup of tea.

She questioned me closely, and I was absolutely honest, about my fears, my motivations, and my willingness to succeed.

Ms. Graham was listing my new duties, "Shorthand and typing, of course, mixing drinks, a little cooking, some further education, and a full course of sex education.

"You will have a full roster, but do not worry too much about your work load, I am far from a monster, you will still have plenty of time for Charlie."

She continued, "I think we need to test your commitment, are you willing?"

After I mumbled my agreement, she picked up her phone, a few minutes later her driver entered the Salon.

"This is James," she laughed, "drivers are always called James are they not?"

"James will you strip please," he quickly did as she asked.

"Geraldine come here please, stand in front of him, kiss him."

His body was much more masculine than mine, he was tanned and well-muscled. I sneaked a peek at his cock, larger than mine. I'd never really been into men, but James was an exceptionally attractive one.

I wasn't ready, I thought I would have months to prepare myself, but I steeled my resolve and then reached up to touch his face and leaned forward to allow my lips to kiss his.

His hand went around my waist and he drew me into him, his tongue entered my mouth, and my hands went around his neck as his kiss depended.

"Very good Geraldine, now let your hand touch his penis, stroke it, get it hard."

I did as I was told, I could feel his cock stiffen under my light touch.

"Kneel in front of him, and kiss his penis," I looked at Ms. Graham, "I am not asking you to have oral sex with him, just kissing his penis will do for now."

I leaned in and pressed my lips against the shaft, soon his hands were lightly pulling my hair suggesting I move more, and so I pressed my kisses in his desired direction.

I was a little repelled by what I was doing, but even more excited.

I decided my feelings didn't really matter, I convinced myself this was all for my Charlie as I ended up kissing the ridges around the hole on top of the purple head.

"That is enough dear," Ms. Graham told me, "please stand."

I did and noticed my hard on was very obvious at the front of my maid's uniform.

"As I thought, I knew you had it in you."

She pointed to a seat against the wall, "sit there please."

"James," she said, "will you make love to me?"

I sat on the seat for the next hour, I'd hadn't seen much porn before, but if the live sex show occurring before my eyes was anything like it, I could understand why people got hooked on it.

I could see them, hear them, smell them, they were both obviously experts and they never spoke except for encouraging moans of passion.

I tried to concentrate on what I was watching, to take it all in, to educate myself, that didn't stop me coming in my panties twice, without touching myself.

I had a new schedule lying on my bed when I returned to my room. I was now excused kitchen duties, I still had maid duties to perform in the morning, but my afternoons were to be spent in a small class room at the back of the Hostel or in Ms. Graham's parlor, or sometimes her bedroom.

Ms. Graham taught me many things, my practical sex education had not restarted yet, but I was taught many other things, to listen, to flatter, to entice with the merest glimpse of flesh to a specifically selected target.

I was taught how to seduce a man, a woman, and importantly for our long term plan, how to recognize someone's true sexuality.

That was a bit of a revelation, I was genuinely bi-sexual, at least according to my sexual tells.

When I told Miss Graham she smiled.

"If you had been one hundred percent straight dear, I would have fed you, cleaned you, let you have nights rest, and then sadly I would have shown you the door."

"You are excused duties tomorrow.

"At eight you will be standing outside my door, choose something flattering to wear, your real sex education is about to start."

I choose a yellow baby doll nighty, with matching lacy panties, they curved around my ass, I felt very sexy and had difficulty tucking my cock as I dressed.

Charlie had set my hair and done a light make up before she headed out to work.

I finished the ensemble with six-inch heels, they further highlighted my ass, and my calves looked very nice in them, even if I was only saying so myself, I was a hot piece of ass.

Ms. Graham opened her door at the appointed time.

"I do like it when a girl tries to look her best when invited to do so, come in dear, you look very fetching."

She handed me a notebook with the title "Sex Education, 101," transcribed on the front. The first two chapters "Female Masturbation," and "Female Oral," had already been marked up as "Passed."

"Today, we will practice vaginal sex, this is a lesson, instruction, you may or may not consider it the loss of your virginity.

"Personally, I would wait until you and Charlie have consummated your relationship to consider that achievement accomplished."

She moved to her bed, and I joined her on it at her invitation.

We kissed, she was much more experienced than I, even after my many make-out sessions with Charlie, and she guided me to better technique by demonstration.

She would kiss me neck, I repeated on hers, she stroked my thighs, I repeated, I undressed her at least five times before I was given a pass mark and we were allowed to continue.

I was pretty confident I could ping Charlie's bra off without difficulty now.

She was lying on her back, her legs spread wide and I had been eating her pussy for at least fifteen minutes when she said, "I am ready dear."

I looked at her and she nodded.

"Sit on your knees and bring your penis close to me, make sure you can see my vagina, ask me to move if you need to, put the head close to the entrance of my vagina, I will guide you in if you need me to, lean forward, push with your hips, and then steady yourself."

I was trying to focus on the mechanics not the feeling of sex, I slipped easily past her vaginal opening, and with her help and encouragement, soon found that I had my entire shaft buried in her.

She was wet and warm, and my cock felt better than it ever had. I moved to her instructions enjoying every second, fucking really was something I should have taken up earlier.

I could feel myself sweating, as was she. We were both panting and moaning, but her stream of quiet instructions ensured my cock gave her as much pleasure as my inexperience would allow.

"I'm going to come," I moaned.

She laughed, "No, not yet."

She slipped her pussy off my cock and did something at the base of it with her hands which stemmed the rising stream of spunk.

I lay on my back as she straddled me. I gasped, her hands had spread her pussy lips, and she slid all the way down my shaft in one motion. I reached for her breasts and received instruction on how to fondle them properly.

I told her that I felt much more in control of my orgasm in this position, she kissed me, and holding my cock inside her, reversed her position, her pussy seemed to grip me harder and I swore as she rode me.

She leaned too far forward and my cock slipped from her, I needed no instruction, I gripped her hips and roughly thrust straight back inside her.

I couldn't contain myself, the noises we were making as her pussy interacted with my cock, the feel, the smell, everything overwhelmed me.

I warned her, then we simultaneously shuddered in orgasm as I dumped myself inside her.

"For your first time, that was very well done, A minus," Ms. Graham was sipping from a long glass of ice water, "but you have much more work to do today."