tagTransgender & CrossdressersLiving Doll Ch. 01

Living Doll Ch. 01


"Shit! What else can go wrong?" I asked myself. "I've got nothing else."

Talk about when things start to go from bad to worse and you need to hit rock bottom before you can climb back up. Lost my job. Car was repossessed. Employment Insurance running out. Girlfriend left. Refrigerator almost empty. Apartment rent increasing. If that wasn't rock bottom, I don't know what is.

I had a decent job as a company librarian which paid enough for my super small compact car and teeny apartment. After the company decided to go digital and after I helped them convert, I was unceremoniously let go with a severance package that was just barely over the minimum and wouldn't last very long. Finding employment in a dwindling market where digitization had taking over everything was impossible. Interview after interview equalled the same result. Even slave labour-odd jobs that paid barely enough for me to survive was difficult. Low on the totem pole was always first cut.

I woke up one morning just in time to see my car being towed away by the bank. The overdraft no longer covered the amount I needed to pay off the six months remaining on the car loan. With no refinancing as an option, well....

After I lost my job and the lack of extra funds caused my social activities to dramatically decrease, my girlfriend Vickie started going out more and more on her own. "Apparently" she met up with her Ex somewhere. She became pregnant and I knew it wasn't mine since she always insisted on making me wear a rubber when we had sex. She left me to be with him (although I heard that many years later, he was unfaithful and got another girl preggers).

Saturday morning. I brewed a cup of coffee reusing the grounds I had reused the morning before. With no milk or sugar... "Yuck! Tastes worse than dirty hot dish water."

I chewed on a stale piece of unbuttered day old bread toasted over the heating element of my stove and choked it down with my cup of joe. It was then I noticed a white envelop that was slipped under my door. I opened it up and read the pamphlet inside.

"Congratulations! As an existing tenant, you are on the ground floor to purchase one of the newly updated condominium apartments."

So apparently the owners boosted up the rents so high in order to get rid of renters and convert the apartments to condos. I could barely afford the rent never mind having enough to purchase a condo.

With no options, I knew what I had to do. Beg. Beg my step-sister for help.

My father was a high level, Japanese executive who moved to North America and through an arranged marriage, married my non-Japanese, Asian mother. After I was born, my mother couldn't handle the stress and left; never to be heard from again. I think she went back to live with her parents in Asia somewhere. My father remarried. Diana, my step mother was English. She was tall, blond and beautiful. Very elegant looking. Her daughter, Cheryl was almost a year older than I was. She was the more dominant of the two of us and because of this I think, she had very few friends; certainly no boyfriends. She scared all my possible friends away as well.

With no one else, we tended to play together a lot. Well, she played, I was forced to bend to her will. Any toys that I got were repossessed by Cheryl, I had to do what she ordered me to do before allowing me access to them.

Cheryl loved dolls. She had hundreds. After pressuring my father to buy a new doll, she would dress them up and play with them for a day before becoming bored with them and want another. Her favourite pastime came to be dress-up; not her or her dolls, me. She would dress me up as one of her dollies. I tried my best to protest but she was always so strong and forceful. Initially she would pin me down and literally crush my testicles with her hand. It hurt so much. After a while, all she had to do was hold up her hand palm up and make a crushing fist movement to make me obey.

I'd pretend I was one of her dollies. She'd strip me naked. Sometimes she would dress me as a baby doll in diapers but other times as one of her girl dolly. We'd have a tea party or play some other game.

After I graduated, I had a huge fight with my father about my Step-mother and sister. While he didn't disown me, I was pretty much banished from the household. He secretly helped me out for a while, then tragedy. My health father had a mysterious, massive heart attack and died. Autopsy found nothing.

As a rich executive, he accumulated much wealth and according to his last will, I was to get most of his estate. But funny thing about the provincial law, his pre-existing will before he remarried was no longer valid. Automatically, any wealth and estate goes to the surviving spouse unless a new will is drawn up which it was not. Because of the argument between us, my Step-mother gave me only a couple of thousand dollars out of the millions as compensation. I used it to consult with a huckster lawyer who took my cash and told me there wasn't much chance of me getting any more. While I kept track of my Step-mother and sister, I cut off any communications with them feeling that I could and would survive without them. Or so I thought.

Less than a year later, Diana died in a horrific car accident along with her new boyfriend. Of course all of her money went to Cheryl who used her inheritance to turn her doll fetish in to a multi-million dollar company.

Monday, I had an appointment to see and speak with Cheryl; the first time in almost twenty years. I was kind of surprised that she would even speak to me let alone meet with me. As I said, desperate times begets desperate measures.

I had rinsed out and hung up my best white polyester shirt so it would be clean enough for me to wear. Monday morning, I carefully ironed out the non-existing wrinkles and creases before putting it on along with my tired blue suit and worn shoes; my interview outfit.

I walked rather than taking the bus to save the fare that I couldn't afford. Fortunately it was cool enough that I didn't work up a sweat but my feet were sore from the trek and bad shoes. I was early enough so I rested a bit before I entered the building.

"Good morning. Welcome to The Doll House." Greeted Gretel the pretty, young receptionist behind the front counter.

"Hello. I'm Andrew Tanaka." I smiled back at her. "I have an appointment with Miss. Cheryl Windsor."

"Yes, I see your appointment." She confirmed on her PC. "Please take this elevator to the 12th floor and see Tanya, Miss. Windsor's executive assistant.

I thanked her and entered the elevator she indicated. There was no buttons to push as it moved automatically and I rode the car up to the 12th. The doors opened to a huge reception area. It was about fifteen steps for me to get to Tanya's desk.

"Hello Mr. Tanaka. Miss. Windsor asked if you can wait for a minute or so before she see you." Tanya asked not really expecting an answer from me. "Please take a seat."

I waited... And waited... And waited... Almost twenty-five minutes before Tanya looked at me and said. Miss. Windsor apologies for taking so long. She will be with you in a minute."

Five more minutes passed before from around the corner came the distinct sound of high heels clicking against the marble floor. I looked up towards the sound as a woman appeared. With the high heeled shoes she wore, she stood almost six feet in height. She was blond, buxom, and bodacious. Her painted red lips broke into a broad grin and exposed her perfect, white teeth. With familiarity she greeted me. "Andi!"

Cheryl always called me "Andi" rather than my preferred "Andrew" telling me back then that "a girlie doll can't have a boy's name."

"Hello, er... Miss. Windsor?" I wasn't sure how to address her in front of other staff.

"Oh you can call me Cheryl." Her smile seemed to be warm and genuine. "Tanya. This is my step-brother Andi... Andrew Tanaka. We haven't seen each other in years but I recognized him immediately."

"Hello Mr. Tanaka. Nice to meet you." Tanya's smile seemed a little less that sincere.

"Oh, call him Andi... With an 'I'. He prefers it." Cheryl corrected her EA. "Come. Let's talk."

I followed her to her office. It was huge. Three time bigger than Tanya's reception area and a zillion times bigger than my apartment. The view overlooked the city and the lake.

We sat down in a carpeted area. I sat in the plush leather wing back as Cheryl lowered herself on to the matching love seat. The hem of her cherry red skirt rode half-way up her thigh. I could hear the sounds of her nylons rub as she crossed her legs.

"So... how have you been?" She asked. We made a bit of small talk before she asked about why I was here. She unbuttoned her jacket and leaned forward. Beneath she wore a white silk chemise. Her large firm breasts pushed out the front. "Okay, Andi. Why after all these years..."

I explained to Cheryl all the mishaps that had befallen upon me. I was in desperate straits to find a job and a place to live.

"Well, unfortunately we aren't hiring here right now. And it wouldn't be right for me to just give you a job because you're related. Nepotism is greatly discouraged amongst the execs." Cheryl told me. "While we aren't really blood, you are my step-brother. It would appear cold if I just did nothing. So... My house is pretty big and I need someone to look after it as I travel."

My hopes brightened at the prospect. Although I tried not to show my enthusiasm, Cheryl noticed. I think she could smell my desperation.

"Tell you what. Come to my place tonight for dinner and we can discuss it more." Cheryl rose from her seat. Her skirt fell back down to above knee level. "Be sure to dress appropriately."

I was unsure of what she meant as she handed me a hand written note with her address on it.

I left the building and made my way home. I still didn't understand what she meant by "dress appropriately" but ecstatic by the chance of having some place to stay. The other issue was I didn't want to go empty handed. I really couldn't afford much. Plus getting there by foot would be difficult. I'd have to spend money on a cab.

I didn't think it would be a formal thing so I ended up dressed in a slightly worn blue dress shirt with the pants from the suit I wore today. I stopped by the corner store and purchased a small bouquet of flowers before hailing a cab. I told the driver where I was going. "The Doll Manor."

"Doll Manor" was in the most exclusive place in town. After verifying my appointment, the security guard allowed us passage to a private road to a gated private estate. It automatically opened as we approached. I paid the driver pretty much the last of my money I had in my pocket and got out from the car. Before I could find the bell or a knocker, the front door opened.

"Hello, Andi." Cheryl smiled but it quickly disappeared as I entered the grand hall. "I specifically said to dress appropriately."

Immediately I was on the defense and apologised profusely as I handed her the bouquet. "I'm sorry. I wasn't sure what you meant and really I don't have much else to wear."

Cheryl gave me a stern, untrusting look. "Well, we'll worry about that later."

We sat and chatted a bit more before the conversation turned a bit more serious.

"So I will offer you a room to stay in, but you must earn your keep." Cheryl told me. "Alishia is getting ready to retire so I'll need to replace her."

"Yes, of course. I understand. I wouldn't except to stay here for nothing." I quickly responded. Maybe a little too quickly.

Cheryl looked and studied me carefully. She told me what she expected of me; clean, cook, garden, etc. In exchange, not only would I get a place to sleep, but food, clothing and some allowance. Not really having much choice: live here or on the streets; I readily agreed.

"Good! Now let's get ready for dinner. It will be in about an hour." Cheryl arose from her seat. She guided me to where my room would be. It was a pretty big room with an ensuite and a view to the front. "First you need to be dressed appropriately. As the owner, President and CEO of The Doll House, I cannot be expected to have a male butler."

I didn't understand.

Laid out for me on the Queen sized bed was a blue dress, some women's underthings, white thigh high stockings and black buckle shoes.

I looked at Cheryl in a questioning manner. Her eyes darted towards the attire and then back to me before she walked out and closed the door.

"Well, I guess I did accept her generous offer. And I guess I can't expect to reside as a male in Doll Manor." I justified to myself. "Not like I haven't worn girl's clothes before. And they are all new. I haven't been able to afford new things in... a long while."

I stripped naked and realized I needed to pee. As I entered the bathroom, it was completely decorated in rosy pink. The smell of lilac came from the basket of fresh cut blooms.

I had time for a shower. I hopped under the stream of hot water. It felt great splashing against my skin. I still had to pee. A hot golden stream flow from my penis and swirled down the drain. I picked up the bottle of shampoo; a Doll House product. It tingled as I cleansed my hair. I rinsed out the suds and rubbed in some Doll House conditioner. It produced a different tingle. I left it in as I poured the DH body wash onto a scrubbie.

I let the shower spray rid me of the conditioner and soap suds. I ran my hands through my hair. It felt softer and thicker than before. I attributed it to the cheap shampoo I used to use. "This is going to be so much better than suffering in my dingy apartment."

I stepped from the shower and towelled off. It was then I noticed my pubic hair; or the lack of it. All my body hair was gone! Being Japanese, I didn't have a lot of hair anyways, but any sparse hairs that I had was gone. My skin was smooth, soft and supple. My nipples seemed to be pointed and excited. My penis remained soft and flaccid.

I emerged from the bathroom a little stunned. The male clothes I had stripped off were gone. Standing there waiting for me was a late sixty-ish woman. The still attractive female was dressed in a maid's outfit. Alishia spoke. "I am here to assist you and finish getting you ready for dinner. In the future, you will be expected to do it yourself. I will also teach you everything you will need to learn before I leave."

I put on the items as Alishia handed them to me. First were silky, pink boy short panties followed by a matching, snug fitting bralette. I felt the slickness of my pink undies rub the tip of my uncut penis. While I felt the sensation of pre-cum start to flow a bit, there seemed to be no associated hardening.

"The AAA cups are a little empty for now." Alishia supressed a smirk. She fingered my nipples through the gauzy bra material. "I think they will produce nicely."

I wasn't sure what she meant but I wasn't given time to think about it as she handed me the blue dress to put on. Reminded me of what Alice in Wonderland wore sans the white apron. As Alishia buttoned up the back, I noted how the short hem flared out due to the ample pink crinoline beneath.

I pulled the stay-up thigh high stocking onto my smooth, hairless legs. It caused a greater stir in my groin area but yet I was still unable to feel any type of erection. Alishia helped me buckle my shoes but as I stood, my stocking slipped down to almost my knees.

Alishia opened one of the drawers and pulled out some suspenders. She had me hold up my skirt as she pulled down my panties and hooked the suspenders around my waists. She fished the straps through the leg holes before pulling my panties back up. After attaching the straps to my stockings, she adjusted the length so they were very taut against the front of my thighs and my bum.

"You have a very nice ass." Alishia complimented me. "Round. Firm. Almost perfect... for a male... Ex-male."

Alishia had me sit in front of a make-up mirror. The table was filled with different items. She gave me a stern warning. "Learn carefully. You will have to do this on your own as well."

I watched and tried to learn as Alishia applied my foundation and make-up. Ample rosy blush on my cheeks, light eye make-up but big, long false eye lashes. With the heavy mascara, I looked like I was peering through jail bars. I thought "How ironic."

"I think this one will do for today." Alishia said as she placed a bob-cut, red with black streaked wig on my head. "Once your hair grows out, you probably won't need to wear wigs."

I looked at myself and couldn't believe how pretty I looked. As I admired myself, Alishia told me. "Dinner in five. Come down to the formal dining area then."

It gave me time to survey myself a bit more. I was no longer Andrew but the "Andi" doll that Cheryl had always made me when we were younger.

I managed to tear myself away from the mirror and made my way down the stairs careful not to trip and fall walking in the unfamiliar three inch heeled Mary Janes. I did enjoy the way they clicked as I crossed the bare stone floor to the dining area. My joy turned into fear as I suddenly realized Cheryl and I would not be dining alone. Sitting with her was Tanya, her Executive Assistant.

"Hello Andi! Don't you look pretty." Cheryl smiled. "Better than those inappropriate boy clothes you had on before. Don't you think, Tanya?"

Tanya gave me a wicked looking smile but agreed with her boss.

"You remember Tanya, don't you Andi?" Cheryl prompted. I acknowledged with a tepid nod. "Oh I forgot to mention, Tanya also lives here with us. She is kind of 'second-in-command' when I am not here. Do you understand?"

I responded with anther nod.

"I said 'Do you understand'!" Cheryl reiterated.

"Yes, I understand."

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