tagTransgender & CrossdressersLiving Doll Ch. 02

Living Doll Ch. 02


After taking desperate measures and contacting my Step-sister Cheryl, I agreed to accept a new position in her Doll Manor household and work to replace her existing maid, Alishia; as a maid. As the President, Owner and CEO of The Doll House, Cheryl c/would not hire a mere male and thus I was made to dress up looking like a female dolly. Problem was I'm not a female. My name is Andrew although Cheryl called me Andi.

So how did I get this desperate? Lost my job with no more Employment Insurance payments coming in. Couldn't find any decent paying job and couldn't afford rent that was just increased or pay the loan on my car which ended up being repossessed by the bank. Since direct eviction was illegal, the landlord boosted the rent to get rid of tenants. They wanted to rebuilt the apartments to sell as condos which I could afford even less. The bank would not extend my overdraft any more.

Not having much other choice, I agreed to be my Step-sister's maid and housekeeper. Alishia the current housekeeper was retiring. She was a very attractive late-60ish woman who could have passed for someone in their forties. She assisted me in getting dressed for dinner: bra, panties, garters with stockings, a blue dress with crinoline and heeled shoes. She did my make-up and gave me a wig to wear.

I thought I was very pretty as I admired myself in the mirror. I was floating on air as I descended the stairway and glided towards the dining area. My heart crash landed as I saw not only Cheryl sitting at the table but her Executive Assistant Tanya. Not just her EA, but Tanya also lived at Doll Manor.

"Sit! Sit, Andi! Tanya won't bite..." Cheryl grinned at my shock. "...Hard!"

"I guess this is all new for Andi." Tanya giggled. She looked directly at me. "You look very lovely and delicious. Good enough to eat!"

Alishia placed a bowl of consume in front of Cheryl, then Tanya then me. It was then I noticed a fourth setting. Alishia placed another bowl down and took a seat behind it. I guess I gave Cheryl a kind of questioning look.

"Oh, Alishia is a live-in. While she does work for me, you can't expect me to treat her as a subservient." Cheryl sipped her broth. "She's part of the family; like a mom."

Without prompting, it pleased Cheryl when I helped Alishia clear the table and bring out the next courses.

When dinner was finished, I helped again with the dishes. Alishia directed me to bring the bottle of VSOP cognac and glasses to the parlour. There I found Cheryl and Tanya relaxing together in the big chair. I poured four snifters and gave Cheryl and Tanya a glass each before handing one to Alishia who also joined us.

"Why does Cheryl call you Andi with an 'I'?" Asked Tanya.

Cheryl gave me a smirking look.

"As you know, Cheryl always loved dolls." I started. "When we were young, we attended a dress-up party. Diana, her mother and my step-mother thought it would be cute to go as Raggedy Ann and Andy."

"But Andy is with a 'y' not an 'i'!" Interrupted a smiling Alishia knowingly.

"Yes. We went as Raggedy Ann and Andy except I was Andy..." Cheryl quickly interjected. "He went as Ann all dress in a blue dress with a white pinny, bloomers, stripped stockings and black shoes. With the red raggy mop hair, Andi really looked the part! Almost the same as he's dressed now!"

I felt my face get hot with blush as the three others laughed.

"You know, if I would have thought of it before, I would have gotten you to dress as Ann." Cheryl mused.

After that and a few more brandies, the evening ended. I went to retire to my new bedroom. Alishia returned to hers on the main floor. Tanya walked towards her own when Cheryl called out to her. "Psst!" And gave Tanya a beckoning head nod. Tanya followed Cheryl behind the closed door.

In my room, I reluctantly removed my cute red wig and placed it on the stand. Again reluctantly, I went to my bathroom to remove my make-up. I stripped off my clothes. It was then I realized I had no night wear. I opened some of the other drawers and found some bras, panties and other women's attire. Hanging in the armoire was a beautiful pink peignoir. My fingers ran over the soft silk and delicate lace material. Pinned to it was an envelope addressed to "Andi". Anxiously I opened it and read the note inside.

"Dear Andi;

I am so happy you agreed to help me here at Doll Manor. I hope you will be as happy as I am. It is good to have family here.

I bought this nightie for you and hope you like it. Enjoy.

Good night.


P.S.: Again, Alishia will help you out for a little while, but you must learn your responsibilities quickly. See you in the morning."

I pulled the lingerie out from the wardrobe: still on its hanger I swung around letting it float through the air like I've seen other girls do in the movies. I laid it on the bed and carefully removed the hanger. I put on the silky, boy short panties first. It felt wonderfully sexy against my skin as I felt the excitement rush through my body and yet my penis remained more than semi-flaccid. The top was a little stretchy so I could pull it over my head and down my torso. The bodice was silk with spaghetti straps. Lacy material covered my belly and lower back. There was also a cape but not to sleep in. I put it on anyways.

I quietly pranced around my room for quite a while until I fell onto my bed exhausted. It was probably one of the most comfortable beds I have ever felt. It was like a warm hug. I fell asleep.

Next morning, I found myself still a top the bed dressed in my pretty pink outfit from the night before. There was a lump that had formed inside my panties. I reached inside my soft boy shorts and started to stroke myself. It didn't occur to me at the time but while I was rock hard, I didn't seem as big as I usually was.

I guess I was more horny than normal and came quickly; messing the inside my panties. A big mess.

"Ahem!" A voice came from the door way jolting me aback. It was Alishia. "Now that you are finished playing, you need to get ready. Did you shower yet?"

"I... Er... B..." I tried to stammer out an explanation of why I was caught jerking off.

"Never mind. Did you have your shower yet?" Alishia repeated. "It's five thirty. You need to get ready and help me. Now take off your nightie and get going."

I pulled off my lingerie and soaked with cum panties before I dashed off to the shower. Again, I used the Doll House products to cleanse myself especially since there wasn't anything else: shampoo/conditioner, face wash, body wash.

As I dried my hair, I found it felt even thicker than even yesterday. "At this rate, I'll need a haircut sooner than normal."

I patted my body with the big fluffy towel. Since almost all of it was gone yesterday, I wasn't surprised to see my hairless, smooth-skin body. But as the towel passed over my chest, my nipples tingled and sent a jolt to my groin.

I looked at them. Not only did the nipple part look more protruded, the surrounding brown areole area looked more swollen and puffed. As excited as I was becoming, my penis remained completely soft. The uncut foreskin was tight and shrivelled and made me look even smaller. I was normally about three inches when soft. Clear pre-cum leaked from the small opening.

Confused, I exited the bathroom. I looked to Alishia was there waiting for me. I wasn't even embarrassed to be naked in front of her anymore. I was a bit disappointed to see that Alishia was holding up a plain looking dark coloured dress which I assumed I was to wear. Disappointment quickly dissipated when her head motioned towards the underclothing she had laid out for me to put on first.

I picked up the panties first. They were baby blue soft cotton bikini panties. I was about to put them on when Alishia noticed my dripping pee hole. She dropped to her knees and proceeded to suck it all out. Her mouth was hot and wet, yet I remained totally soft.

When she was satisfied I would no longer leak, Alishia let me pull up my tight fitting undies. She smiled when I turned to show her my bum. It was nicely rounded. Then she stuck her hand down the front and showed me how to tuck myself in so there would be no unsightly bump.

Next she handed me some plain garters. As I hooked the eyelets she told me. "We always wear stockings; never pantyhose (which was fine with me). Normally the straps would go under your panties but because they are so small and tight the straps can hang over."

She handed me the matching baby blue bra and instructed me on how to put it on. I noted how nice it felt as I reached around my back to do the hooks. I snaked my arms through the loops and pulled the straps over my shoulders. My swollen breasts did not fill the AAA cups. The material rubbed and tickled my sensitive nipples. I felt more pre-cum trying to leak out, but the way Alishia showed me how to tuck myself in prevented it from staining my pretty panties.

The stocking were dark to match the plain dress which Alishia helped me on with. The front was a square cut that would show very little cleavage if I had any. The sleeves came halfway down my biceps and had white frilly trim on it. It was tight fitting around my waist and the skirt part fell loosely around my thighs. The hem stopped just over midway to my knees.

Since we were going to be busy, Alishia had me wear some low three inch black shoes so I would be easier for me to walk around in. She added. "Once you get more used to everything, you can wear the higher heeled pumps!"

Alishia supervised me as I put on the wig and applied my make-up. The tough part was gluing on the eye lashes and applying the mascara. Alishia correct a couple of things, but was overall pleased with how well I learned from the previous evening's lesson.

"Come! Seven o'clock." Alishia beckoned me with a finger. "Time to wake Cheryl."

It was still a bit difficult to walk with these new shoes on, but I followed Alishia as quickly as I could to Cheryl's bedroom. She instructed me to softly knock on the door before opening it and announce it is time to wake.

I gently rapped on the door and turned the knob to open it. "Cheryl. Good morning. It is time to..."

Was all I got out of my mouth as I saw Cheryl splayed naked on her back. Tanya was between her legs; her face was between Cheryl's thighs; her mouth slurped and munched at Cheryl's cunt.

"Uuuh! Uuuh! Uuuh...!" Moaned Cheryl. "Yes, Tanya. Right there! Oh god you eat me so well!"

I looked at Alishia for guidance. She motioned for me to remain there silently. I continued to observe the two women with my own excitement building. Still, I felt my penis remain soft.

Cheryl grabbed the back of Tanya's head and pulled Tanya's face into her pussy even more. Tanya doubled her effort. "Oooo... Fuck! I'm cumming...!"

Huge wet squirts washed Tanya's face as Cheryl orgasmed violently. Tanya kept her face against Cheryl's twat as she thrashed about.

Patiently, both Alishia and I waited until the panting Cheryl had recovered a bit. "Good morning, Alishia and Andi. Thank you for waking us. We'll have breakfast as normal."

Tanya sat back on her legs. Her face coated with shiny slime. The bed saturated with wet. I watched gaped mouth as Cheryl arose from her bed. She was just so beautiful to look at. Her long blond hair; her large firm breasts; her curvy Rubenesque body; her long shapely legs.

"Yes, Cheryl." Alishia responded. "Come, Andi!"

I turned to follow.

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