Chloe 03

Story Info
Embracing the change, going further down the rabbit hole.
4.9k words
4.74
9.3k
14

Part 3 of the 21 part series

Updated 06/11/2023
Created 01/17/2022
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Chloe Development

It had been another busy day in the office so it was gone seven in the evening by the time I reached home. I retrieved my keys and opened my door. A dozen jiffy bags, small parcels and assorted envelopes greeted me. I gathered them and stepped inside.

"Hello," called a feminine accented voice from behind me.

I turned to find my neighbour at her door. Emma? Andora? I couldn't remember. We had met on the stairs a few times and had shared basic greetings.

"Hello," I replied.

"Sorry to trouble you."

Again I heard the beautiful accent- Polish, Bulgarian may be Ukrainian?

"How can I help?" I asked sincerely.

Damsel in distress I thought, another scenario to be explored.

"The delivery man came earlier and I took in your parcel. You probably have a postcard in there somewhere," she indicated my collection of post.

"Oh, that's very kind of you. Give me a second and I will dump these."

I entered the apartment and placed the packages on the dining table. I returned to the hallway.

"I noticed you were working late recently. Don't worry I am not your stalker. I just didn't want you to have to go to the main office to collect it."

"I really appreciate your help. I am sorry I am having a complete mental block and I can't remember your name," I admitted.

"Aurora."

Sunrise: this beautiful lady was warm and sunny.

"Right," I nodded remembering.

"And you are Chris?" she tested.

"Yes." I almost never went by Chris, but perhaps that is how I had been introduced by Elena, my ex.

"It's that box there," she indicated a brown cardboard box eighty centimetres cubed.

I lifted it from the floor. It wasn't heavy, just large.

Aurora was slim, as tall as me, in her late twenties or early thirties I estimated, with long luscious dark brown glossy hair tied back in a pony-tail. She was athletic, but almost delicate like a ballet dancer, and I had an impression of strength, independence and self-reliance.

"Thanks again. I will get out of your way. Enjoy your evening."

"No problem, may be you can do me a favour sometime?"

"Absolutely, you know where I am. Let's have coffee sometime. Let's make it my shout as a thank you."

She smiled and it was as if the sun came out. Was it too soon to consider a new relationship?

"I would like that," she asserted as she closed her door.

I returned to my apartment and placed the box on the table. I returned to the front door and locked it.

I opened the many packages: satin panties, tights, holdups, stockings, suspender belt, and bras. I opened the large box: black patent block Mary Jane shoes, black patent three inch stiletto court shoes, a pale blue blouse, white blouse, navy pencil skirt, matching jacket, wig, breast forms and dance clothes. I placed everything back into the box and took them to the spare room. The wardrobes and cupboards were empty. I practically ran to the main bedroom and stripped. I quickly showered and dried myself. My body was still hair free, soft and smooth. Going forward I would need different shampoo, conditioner, body wash, more razors, deodorant and perfume. I made another mental list for the grocery store.

I returned to the spare room. I added the white bra and inserted the breast forms. These forms were slightly larger than the ones I had worn as Chloe the school girl, these were size C. They looked in proportion to my slim body. I decided this would become Chloe's room. I would need to purchase new curtains, and bed linen. I pulled on white satin panties and realised I had neither plug nor cage- maybe I would need to make further purchases. I decided on the suspender belt purely because I had never worn one before and then carefully rolled the light sheer stockings up my legs. I smoothed them: they felt amazing! I continued with the white satin slip, pale blue blouse and skirt. I took the wig to the bathroom and arranged it. Chloe was back. I slipped my feet into the heels and stood carefully admiring the vision in the mirrored wardrobe doors. I took one step and nearly fell. This would take much more practise. I replaced the heels with the block Mary Janes and tried again. It took concentration, but I could walk. These block heels were twice the height of the pair I had worn before, but being blocks they seemed easier to walk in- more surface area I concluded.

What if Aurora saw me now? I was both thrilled by the prospect and filled with dread that she would reject me as a freak.

I spent the evening in the apartment as Chloe: I cooked dinner, made a cup of tea, and watched some television. I lost interest in the television programme and shut it down.

I logged into the forum and located 'The Wendy House'

Me> Hello, anyone around?

Nothing for what seemed like an age.

>Hello, what's happening?

Me>>can we go to private?

We activated the private channel.

Me>>I bought some clothes and I'm wearing them now

>>Exciting! Tell me what you are wearing?

Me>>Satin panties, matching bra, suspender belt, stockings, slip, blue blouse, navy pencil skirt and block heels.

>> Wow :-) Lovely. You have been busy. Have you ventured out?

Me>> No way!

>>Why not?

Me>>Need make-up lessons for starters and I am not ready for anyone to see me.

>>I have seen you.

Me>>That's very different!!

>>So you would go out if you wore makeup?

Could I? Would I? Dare I? Images of exposure flashed through my thoughts. Humiliation in public, people laughing, abuse and the anger of the mob made me afraid.

Me>>I don't know. I don't think I could.

>>No pressure, no decisions, just seeing where you think you are.

Me>>How did you know I was in the forum?

>>Wow serious subject change LOL

Me>>Sorry.

>>Nothing to be sorry about. It's a fair question. As an administrator I have an app on my phone.

Me>>ok makes sense.

>>I didn't intend to make you uncomfortable. I would never do that and you know I don't judge. You can be as honest as you are comfortable with. Just no lies 

Me>>It's a lot to think about.

>>I know. How do you feel?

Me>>I am comfortable, contented and happy. So you can watch the app anywhere?

>> With the app I can access when someone is logged in. I never initiate a conversation: sometimes they visit, see nothing and leave. If they type I reply.

Me>>Then you see what they want to talk about?

>>That's it. Some people are content with the chat, others for me to tell them a story, a few want to meet to talk and the very few get the experience.

Me>>Like me.

>>Yes, like my pretty Chloe!

Me>>The first time we spoke you asked about Alice.

>>I remember the conversation fondly. You fell though the rabbit hole. LOL

I smiled at the memory.

Me>>I plummeted down that hole and into wonderland. Do you have the dress?

>>I do, and others.

Me>>I would like to try the dress, but still be Chloe.

>>We can do that.

Me>>I look forward to it.

>>As do I.

Me>>I feel lucky to have met you.

>>I feel fortunate to have shared time with you too. I like my boys to be pretty girls.

Me>>It's late, I will sign off and see you soon. Thank you. Good night.

>>Sweet dreams my pretty girl.

Me>>And you.

I retreated to what I now thought of as Chloe's room. I undressed and stood naked feeling a cool breeze on my smooth naked body. I put the clothes on hangers and the shoes in boxes inside the wardrobe, the clean underwear and hosiery in the cupboard. I removed the breast forms and placed them in the box. I found French knickers and slipped them over my bum, then the nightdress and adjusted it. The satin against my skin felt lovely. The panties and stockings I placed in the laundry box. Finally the wig came off and placed it on the stand. I slid between the sheets and was almost instantly asleep.

The next day was Saturday. I showered and returned to Chloe's room. Lycra panties and bra, breast forms, stirrup leggings, leotard and skirt: all in hot pink. Satin ballet shoes with satin ribbons. I considered the wig, but decided not to risk it. I looked at myself in the mirror and smiled. I tried to remember the dance moves I had learned. I replicated them in front of the wardrobe mirrors. I enjoyed the exertions and could feel muscles tightening, but also stretching. I curtsied to my reflection. I undressed and showered a second time.

The desire to be Chloe was strong, but I needed to be practical. I dressed in satin bikini styled panties, black opaque tights, bra, slip, but wore my man dark blue shirt, jumper and black trousers. I was hiding in plain sight. I couldn't wear the breast forms or the wig, but this felt like a happy compromise. I ventured out for the first time partially dressed. My first adventure into the world was to the supermarket for my usual supplies. Was everyone watching me? I didn't think so. I was just another shopper. I collected my usual groceries, but also added feminine shampoo, conditioner, body wash, deodorant and moisturising cream. Another large pack of razors and a multi pack of opaque black tights.

The checkout lady had made no comment, clearly assuming I was shopping for a girlfriend. I returned home. I entered Chloe's room and removed the trousers and shirt. I inserted the forms into the bra, buttoned up the blouse and zipped my skirt. The block shoes were strapped and the wig in place. I felt calm, and loved the feel of the feminine clothing.

I logged into my computer and setup a new email address for Chloe. I went to Amazon and ordered perfume (a scent I liked which I had bought for Elena some time back) foundation, lipstick, eye shadow, eye liner and mascara. I had no idea what to do with it, but I was due lessons soon. I looked at more underwear, shoes and dresses. I made further purchases. I then found a silicon chastity cage and a butt plug and purchased them ensuring they would be delivered in plain discreet packaging. It would be a disaster if the post office or a neighbour knew what I had ordered.

Sunday was appointment day. I dressed in panties, tights, camisole top, a man's shirt, trousers and shoes. I took the same route as before and arrived at the house.

I pressed the bell and the door opened. The Mistress was wearing a black knee length A-line dress with v-neck and half sleeves, sheer black hosiery and black patent heels: a vision of loveliness as I had come to anticipate.

"Good morning sir, how may I help you?" she asked exactly as she had on my previous visits

"I am here for my appointment," I replied with a smile.

"Please come in," she invited opening the door wider.

I stepped inside and she closed the door.

"It's good to see you Chris, how have you been?" she greeted me.

"I'm good, thank you, how are you?"

"I am very well. Thank you for asking. Shall we have coffee?"

"Please may I have tea," I requested.

"Sure no problem, English Breakfast ok?"

"That would be lovely," I confirmed.

"You have your envelope?" Stephanie prompted.

I retrieved the familiar pink envelope from my pocket and handed it over. Stephanie examined my manicured nails nodding her approval. She read the letter as we drank our tea. It was a comprehensive description of my request.

She nodded thoughtfully.

"Too much?" I asked.

"It's your experience."

"But it's your precious time. I wouldn't want to take advantage of your kindness."

"I enjoy this as much as you. That is why 'The Wendy House' exists."

"I don't wish to offend, and please don't reply if I do..."

"Chris, just say it," she instructed placing her warm soft hand on mine looking directly into my eyes.

"Do you...?"

I was trying desperately to find the right polite term for orgasm or climax.

"Orgasm?" she completed my thought.

I felt my face flush and nodded.

"You know the little black box?"

Oh did I know the black box! I loved the black box. I nodded again.

"Well it controls my devices too," she admitted.

Wait, her electronics? So it controlled my butt plug and the nipple pads and?

"You have devices?" I heard myself ask.

She smiled.

"My nipples like stimulation just like yours, my bum likes stimulus just like yours, but I have the benefit of an extra device."

"Oh," was all I could manage.

"So shall we begin?" she asked taking me by the hand.

I followed obediently. We entered the small room and I performed the now regular activity of undressing. I stood naked, smooth, expectant and a little anxious.

She knocked.

"Please come in," I invited.

"You are always so polite. I like that."

"I try to be," I mumbled.

"So, Chloe, it is time," she said with a smile, using my girl name.

We entered the pink room. We returned to the world of Chloe. I had been transported to a realm of pale pink walls, matching carpet and frilly curtains, the single bed with pink linen. I noticed the dressing table and two chairs. The large wardrobe of secrets and mirrors watching me approach.

She handed me the ear plugs and I inserted them.

"Can you hear me Chloe?"

"Yes, Mistress," I replied.

She handed me a condom, the chastity device and the butt plug. I was becoming accustomed to the process. She then handed me white satin knickers which I put on carefully. She handed me adhesive pads which I attached to my nipples. Then the small realistic breast forms which I fixed to my chest. The white satin bra held them in place. White tights encased my smooth legs. Bloomer like satin shorts went over the top, white frilly lacy topped ankle socks, a satin petticoat followed by a net petticoat and then the dress. It was pale blue with a peter pan collar. It zipped up the back.

"Would you like it locked?" she asked with a smile.

"Yes, please," I requested.

The padlock clicked in place holding the zip imprisoned between two metal rings. The white apron was wrapped around and tied behind me in a large bow. I was handed the block patent Mary Jane shoes. I slipped my feet into place and secured the straps. I was dressed. I stood and walked exhilarated by the clothing. From the neck down I was 'Alice'. I returned to my seat for the blonde wig to be fitted. I was complete.

"Ready for your treatment?" she queried.

"Yes, Mistress," I responded enthusiastically

She led me from the room, down the stairs to the ground floor and then down another set of stairs into the cellar. I stood in astonishment at the many interesting items of furniture and implements. This was a dungeon. The walls were painted a dark red.

I followed her to a padded bench.

"You are ready?"

"Yes, Mistress," I confirmed, both thrilled and afraid of what was to come.

"Place your body at the end of the bench and bend over."

I complied and submitted to her hands as they guided my body. I felt her hands guide my feet to where she needed them and leather padded cuffs secured me. My wrists were secured next so they were in front of me holding me tight. A strap was secured across my waist making movement nearly impossible. Another strap across the back of my knees completed the restraint. I had been spanked with a black leather strap while dressed as a school girl, but I had not been restrained. I felt I needed to do this, but couldn't really explain why. I felt my dress and petticoats being lifted exposing my bloomers. The bloomers were lowered leaving only my tights and the satin panties as protection. I felt my face burn knowing my underwear was on display.

"You sure you want twenty?"

"I am sure, please Mistress I have been a very naughty girl."

I heard the air move and the crash of the first hit. Pain exploded from my left bum cheek, before I could cry out a second arrived on the right side. I squirmed, but could not escape. She alternated between left cheek, right cheek, top of left thigh and top of right thigh. I cried out, but did not use my safety word. I felt tears burn my eyes. I generally didn't cry, the last time here in this house dressed as the schoolgirl I had been spanked and cried. Prior to that event I had not cried in years, in fact I couldn't remember the last time. May be as a child? I heard a sob escape my lips.

"That is twenty," breathed my Mistress from the exertions.

I wasn't sure why, but I heard myself make a further request.

"I think I need another ten please."

The spanking resumed and I was full on sobbing now. It felt like... a release.

The pounding ceased, the straps released and I was guided back up the stairs to the lounge.

Mistress sat me down and handed me a tissue. I wiped my eyes and my nose. She sat beside me on the sofa and pulled me close she wrapped her arm around me I leaned my head on her shoulder. We exchanged no words, but I could feel her warmth as she stroked my hair. I am not sure how long we sat like that and it didn't matter.

My sobbing ceased. She gently guided my head so I was lay with my head in her lap. I felt the nipple and plug wake and slowly increase their motions. I felt Mistress react to it too. We lay together in this position for quite a while.

"Ooooh," breathed Mistress as she shuddered.

I felt my own climax as a series of pleasurable explosions in both my bum and on my nipples. I closed my eyes and allowed the feeling to envelope my entire body. I sat up and opened my eyes. I watched as my Mistress slowly opened her eyes. She smiled and patted my exposed thigh.

"Would you like some tea?"

I laughed releasing the last of my tears.

"I would love some tea," I replied dabbing at my eyes.

We headed for the kitchen. I felt a little stiff, perhaps even a little bruised, but not really in pain. I rubbed my bottom, even through the many layers of the dress, petticoats and tights it felt warm compared to my hand.

"Take a warm bath when you get home."

I dabbed my eyes again.

"I must look a fright?" I volunteered.

"Not at all, there is a mirror in the hall, take a look."

I walked carefully in my shoes and inspected my reflection. I adjusted my hair and brushed the front of my dress. Surprisingly I looked ok. I returned to the kitchen and accepted the cup of tea.

"I was surprised that you asked for more," she said as I tried to emulate her feminine movements.

"I was surprised too. Thank you, I think I have needed that for a long time."

She smiled her usual knowing smile.

We drank our tea.

"I am very proud of you Chloe."

"Mistress?"

"Yes?"

"May I hug you?"

She held out her arms and we embraced.

"Shall we continue with lessons?" she prompted after a moment.

"I would love to have more lessons," I confirmed.

We returned to the bedroom.

"Come and sit at the table," instructed.

I sat and adjusted my dress.

"This how we look after our nails," advised my instructor. My nails were short and I kept them tidy and short.

"You will need to let them grow a little so you can have beautiful nails."

I looked at her immaculate black shiny almond shaped nails. I nodded my agreement. She filed them into a more feminine shape, not too much to stand out in real life, but enough to demonstrate the process.

"We could also use adhesive nails if you would like them longer?"

"No I am happy for this, for now," I allowed.

If they were too girly it would attract unwanted attention and would instigate too many questions. White undercoat nail polish was applied in two coats and then a pale blue top coat to match my dress.

"You might want to do paint your toenails for next time," she suggested.

"I hadn't thought of that," I admitted waving my fingers gently to dry them.

"It will give you chance to practise and wear nail polish and no-one will know, unless you go swimming," she laughed.

"No chance of that!"

"You are nicely shaved and moisturised," she complemented stroking my cheek and chin.

I love her gentle touch on my face and my body. It is always reassuring.

"I am going to shape your eye brows and thin them just a little."

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