Chloe 02

Story Info
A return to the house of dreams.
4.9k words
4.69
8.6k
12

Part 2 of the 21 part series

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

Two weeks had passed and I was back at the house. I had a serious case of déjà vu. I was dressed similar to last time: plain shirt, dark trousers, and outside coat. I had made the same preparations and travelled the same journey. My journey I had been anonymous and no-one had looked at me twice.

I pressed the bell and the door opened. The lady looked as beautiful as my previous visit- she was wearing a pink satin blouse, dark red skirt, light coloured hosiery and high heeled red patent court shoes with an ankle strap. She was a commanding and beautiful presence.

"Good morning sir, how may I help you?" she asked exactly as last time.

"I am here for my appointment," I replied providing the requisite password.

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

Did she recognise me from before? How many other boys had passed through this doorway into wonderland?

"You have been here before," she stated as she closed the door behind me.

"Yes, last time I was..." I was unsure quite what I was going to say.

"Indeed," she confirmed with a comforting smile.

Was she reading my mind? My mind had been chaotic recently. We walked through to the familiar kitchen. I revelled in the sound of her heels on the tile floor, her grace and her perfume. She thrilled all of my senses: sight, sound, touch and scent. She collected a coffee jug from a machine and poured.

"Coffee, white and two sugars," she stated placing a cup and saucer before me.

"You remembered?"

"Yes," she replied simply sipping from her own cup.

"How many... guests, do you have?"

"I do not discuss other guests with anyone," she chastised gently waving a finger at me.

"You just need a white cat and say 'you were expected' and add a little evil laugh," I jested.

Her laugh was cheerful in response.

"I'm not sure I can do an evil laugh," she replied.

I smiled. It had been a couple of weeks, but she remembered how I drank my coffee. It was really good coffee, freshly made and strong. It had taken me a while to come to terms with my experience. I had wrestled a multitude of conflicts, mental struggles, flashbacks and dreams. I battled guilt, embarrassment, pleasure, before I think finally reaching a form of acceptance. I was hurting no-one, I was doing nothing illegal, and we were consenting adults. I wanted more.

"Of course, my apologies," I replied sincerely.

I drank the coffee. We chatted about the recent news stories and a television series we had been following.

"Do you have your envelope?" she prompted when I returned my empty coffee cup.

It was the same as last time, but different. I felt more relaxed- this was a safe environment, but nervous at the same time. It was time. I reached into my inside jacket pocket and retrieved the required envelope. It was pale pink. I handed it over.

"I trust you have followed your instructions?"

I nodded.

"Then let us begin. Come with me," she instructed.

We ascended the stairs and entered the first room. It was the same small room, a solitary single bed and lonely wooden chair. It was exactly as it was last time.

"You will undress, then place your clothes in the bag provided and I will return in ten minutes."

She left and closed the door quietly. I followed the instructions quickly and waited for her return. There was a knock on the door my ten minutes were over.

"Please come in," I requested.

The door opened and the lady entered.

"Ready?" she asked simply.

"Yes."

"I have read your letter, from this point you will speak only when spoken to, unless you use your special word. Say it to me now."

I spoke the word. The setup was lightly different to last time, but then this was a different scenario.

She reached out to me and took me by the hand. Her touch was warm, soft, but firm. I allowed her to lead me to what I considered the pink room. The pale pink walls, matching carpet and frilly curtains were familiar. The curtains were closed to the outside world. The bed with matching linen, the, room length, wardrobe was closed hiding its mysteries.

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

I had repeated the task of removing all body hair except for my eyebrows and that on my head as I had on my previous venture. An enema had been completed just before I left my apartment. I could feel the adrenaline building.

"Yes, Miss," I replied.

"Good girl, Chloe."

She handed me the ear plugs and I inserted them.

"Can you hear me Chloe?"

"Yes, Miss," I replied.

She went to the second set of wardrobe doors and collected a number of items.

I heard the whisper in my ears- 'You are a good girl, and good girls are rewarded. Bad girls are punished. Good girls wear pretty clothes, frills and ribbons. You like wearing pretty lingerie and tights. Chloe loves her butt plug. Chloe loves bra and knickers and petticoats and tights and high heels.'

"Sit on the bed, please," she ordered sternly.

I obeyed instantly.

"You will follow my instructions!"

"Yes, Miss," I acquiesced.

"I will hand you the item and you will dress yourself."

She handed me a condom and a chastity device. Last time I had submitted to her as she had prepared and dressed me: this time I guessed I would be responsible for preparing myself.

"I think you know where this goes," she said playfully.

I rolled the condom over my penis and then attached the cage. I was aroused, but could not manage an erection. The small lock clicked in place. Then the butt plug. It looked bigger in my hand, but last time I had not seen it as closely as this and the lady had inserted it. She squeezed lube onto the plug.

"Slowly and gently," she suggested.

I nodded and guided it into my hole. It felt bigger and I was concerned it would damage me, but I breathed out and my bum embraced it drawing it quickly into place.

"Oh," I breathed. I sat for a second enjoying the fullness.

She then handed me white satin knickers which I put on carefully. I noticed there was a cute bow on the front waistband. She handed me the adhesive pads with which I attached to my nipples. I watched with astonishment as she stuck small realistic breast forms to my chest. The forms were flesh coloured and concealed the pads beneath. The adhesive was cool, but quickly warmed. This was followed by a white satin bra which my teacher had to assist with. I had never worn a bra before. I had never had breasts before. I had breasts! Before I could fully appreciate my predicament my thoughts were interrupted.

The voice continued to repeat- 'Bra and knickers and petticoats and tights and high heels.'

"So Chloe, what colour uniform would you like? Blue, grey, red or black?" asked my beautiful companion.

I was being given choices. While I considered the options she consulted the paper from my envelope. I guess she was checking my body dimensions to determine sizes and the other options I had selected.

"Please Miss, may I have blue?"

I had no idea what I was choosing.

I was handed white tights and shown how to put them on. The caress of tights on my smooth legs was bliss. I ran my hands down my legs smoothing out imagined creases. I liked the feel of stroking my hosed legs. I giggled with pleasure. My teacher handed me a white satin petticoat which I slipped over my head -- it whispered against my upper body with every move. From the wardrobe came a pale blue school blouse with a revere collar, knee length navy pleated skirt, and black Mary Jane shoes. I slipped the blouse on easily, but the buttons were the opposite way round forcing me to concentrate. I stepped into the skirt and adjusted it around my waist. Then I sat on the bed and put my feet into the shoes. I leaned forward to secure the straps feeling the bra brush my small breasts. I was dressed. I stood up in the low heeled shoes feeling the petticoat and tights swish together. The shoes were low heeled, but I had never stood in heels of any description before. I looked to my guide.

"Why don't you walk around and get used to the shoes?" she suggested.

The low heels were only an inch and block shaped, but initially I stumbled unused to the foot position. I quickly adjusted taking smaller steps.

"You need to walk like a girl, talk like a girl, be a girl."

I continued to practise as she watched me.

The voices continued too- 'Bra and knickers and petticoats and tights and high heels.'

"Not bad, but now we need to do something with your hair, come and sit on this chair."

I looked in the mirror. From the neck down I looked like a school girl, but my short-ish plain blonde hair made me look like a boy in a skirt.

I sat on the chair as instructed. Several different wigs were tested and rejected, until a shoulder length dark brown bob style was selected.

"Well don't you look pretty? I think this one, what do you think?"

I smiled and nodded. Chloe was back. Chloe seemed more real this time. I was Chloe.

"Ready for your treatment?" she asked.

"Yes, Miss."

We stepped into the hall. I heard the tapping of two pairs of shoes- the stiletto heels of my teacher and my own inch block heels. I was led into another new room. This was setup like a school room with three student desks in a single row and a larger teacher's desk at the front. I noticed the little black box was attached to her waistband.

"So Chloe, you are here for detention. Take your seat. Firstly you will watch the video and complete your homework."

I watched in awe as the video explained the various items of under clothes unique to a woman: knickers and panties in different styles, bras also with a dozen variations, corsets, bodies, teddies, suspender belts, and my favourite tights. I saw images of stockings, camisole tops, and various different types of petticoat. I also watched as demonstrations were performed on how to wear the various under clothes. The lady in the video wore a white leotard and was not embarrassed in the slightest as she demonstrated the feminine items. I was entranced- different underclothes worked on different body shapes: I had no idea it was so complicated. As a man you had a simple choice of shorts or pants as underwear. The video ended and my knowledge had multiplied. I had watched Elena dress many times, I had indeed undressed her many times, the catches, hook and eyes, and suspender clips, but I had not really appreciated the efforts that women went through every day.

My teacher placed an exam paper in front of me.

"Write your name on the top of the exam paper and you may begin. You have twenty minutes."

I read through all the questions as I had when at school. It was a long paper, none of it was multiple choices and there were one hundred questions. Basically all of the questions related to the video, but it would be impossible to complete in the time. I tried to remember all of the identifying names, the terminology, descriptions, and the differing styles. I wrote frantically.

"Time is up."

I had completed forty-one questions, but I was neither confident they were complete or correct. Teacher took her place at her desk and slowly marked my exam. I think saw ticks, but then it could quite easily be a line through meaning wrong. I had no idea of her marking scheme or even the pass mark.

I heard the voices again reciting.

'Bra, knickers, panties, teddies, corset, basque, suspender belt, stockings, petticoat, heels. You love to be dressed in pretty lingerie.'

The message repeated over and over. As I heard each word I matched a mental image in my mind. The message finally faded.

"This is very disappointing Chloe," reported my teacher as she stood.

"You will bend over my desk. You will lift your skirt and petticoat and submit to punishment," she commanded sternly.

I looked down at the floor feeling that I had really done something wrong. I could see her lovely legs and her red high heeled shoes. I stood and shuffled forward.

"You will receive a dozen strokes of the paddle and you will count them," commanded the strict voice of my teacher.

"Yes, Miss," I replied.

I saw the black leather paddle. It resembled a cricket bat, almost a foot long and four inches wide. What was I doing? This was getting out of hand protested part of my brain, but the other part complied with the request. I bent over my teacher's desk, lifting my skirt and petticoat to reveal my legs encased in white soft tights. At least I was not being spanked on my bare bum. I was not sure that knickers and tights would be an adequate barrier to pain. I placed my hands in front of me, and felt my breasts through the bra touch the desk top. I was not restrained and I could leave, but I was choosing this. I have never been spanked, not even by my parents. I wasn't into pain; at least I didn't think I was.

Smack! My brain registered the sound, but no impact. I had fleeting thoughts relating to light travelling faster than sound. May be it was a test slap? Then pain hit me like shockwave. Wow that hurt!

"One," I squeaked, desperately fighting the desire to rub my bum.

Eleven more strokes followed and I counted each breathlessly and as girly as I could after each one. I think I have a pretty good threshold of pain, but by the last I was twisting to avoid the hit. She could have hit me a lot harder, but she seemed to instinctively determine where my threshold was. She had clearly performed this task before. She had expertly applied the strap across both bum cheeks and I was sure it was glowing red, but not as red as my cheeks on my face. I felt her hand stroke my bottom pleased with the heat emanating from it.

"Stand up," instructed my teacher.

I stood and I straightened my skirt feeling hot tears roll down my cheeks. The strikes had been spread over my entire bottom and tops of my thighs. It was less about pain and more about humiliation. I had been a naughty girl.

"Now, return to your desk, and write out twenty lines."

She turned a blackboard to reveal the words I would need to write.

"I must be a good girl. Good girls are rewarded. Naughty girls are punished. I must do my homework. I love bra, knickers, suspender belt, stockings, petticoat."

I pulled out the chair, and sat as I instructed, feeling the punishment for a second time and feeling the plug penetrate further. My teacher handed me a pink tissue and I wiped my eyes. I picked up my pen and began to write my lines. I could hear the voice in my head reciting the lines. I tried to sit still, but my bum was glowing. I had disappointed my teacher and I had been punished. I was confused and disorientated. What had I done wrong? I couldn't remember. I felt the plug wake and stimulate deep within. My breasts were bathed in electrical energy. Teacher sat at her desk and observed me. I tried to concentrate on my lines, but I was aware I was breathing hard. I have no idea how long I persevered on my lines, but I completed my task. I felt my body surrender to a huge climax.

"Please Miss, I have finished."

The sensations in my knickers and bra slowly diminished. I missed it already. I noticed my teacher was flushed. Had she reached a climax of her own? How did that work?

"Very well, come with me."

I followed my teacher back to the dressing room. Walking brought its own rewards. The feel of tights brushing together, the addition of satin petticoats that whispered. I could hear my clothes moving together. Our shoes tapped out our progress. She held the secret black box in her hand.

"Strip naked," she ordered.

Was the session over already?

"Time for dance class!" she commanded enthusiastically clapping her hands twice.

I slowly undressed and laid the uniform on the bed neatly folded. Chloe was disappearing

I was handed a sports white bra- Lycra I think and matching panties. I quickly put them on. White ankle socks followed. No tights? My face must have betrayed me.

"It will be all better in a few minutes, Chloe," reassured my teacher.

She handing me pink Lycra stirrup foot dance leggings. I pulled them onto my legs. If tights were bliss then this was a delight. I took the next offered piece of pink clothing. I unfolded it to reveal a leotard. I was confused- how did you put it on? So many new clothing items, I was overwhelmed, but was soon rescued. I noticed the front and back had slightly different shapes.

"The wide part goes to your bum and smaller part covers your front. Step through the neck and slide your legs in, then feed your arms in."

I pulled it on and was aware that my cage was very visible.

A pink ballet tutu satin and net skirt completed my new look. My teacher knelt before me and guided my feet into flat satin dance ballet shoes. She wrapped the satin ribbons around my ankles and tied them in place. She ran her hands down my legs smoothing invisible creases.

I shivered at her wonderful caress.

"Well, how do you feel?" she asked looking into my surprised blue eyes.

"Lovely," I whispered.

"Now is my pretty Chloe going to be a good girl or a naughty girl?"

My mind raced, what trick was this? If I chose good girl would I miss out on some kinky ecstasy, or would I be rewarded for being a good girl. I didn't think I wanted or could take another spanking.

"Please Miss, I will be good," I promised with my girly voice.

She smiled, stood and took me by the hand and led me back down the stairs. Was she planning on taking me outside? She opened the first door on the ground floor and saw with some relief a small room with a large screen and a wall length mirror. The floor appeared to be laminated wood.

"This is the dance studio. You will watch the screen and follow the instructions. I will be watching."

She retreated, closed the door and left me alone. I noticed two cameras in the room. Would I be recorded? Would anyone recognise me? The screen came to life startling me. I watched as it displayed a young lady dressed in similar attire to me. I listened in awe as she introduced herself explaining that I would be learning ballet dance steps, posture and movements. I emulated the dance moves with less grace than my teacher, but I tried really hard. I wanted to succeed. Repeating the moves improved my poise. The time passed quickly as I mirrored the moves.

"This concludes this lesson. Thank you for your time. I hope you enjoyed this session and hope to see you next time. Happy dancing!"

The young lady curtsied and I replicated this new move. The screen finally blanked. I instantly felt the growing feeling of loss. A few moments later my teacher opened the door and entered the room. She approached me, embraced me and kissed me on the forehead.

"You did very well! A very good girl!"

She handed me a glass of water which I drank.

She took me by the hand and we returned to the dressing room. Did that mean the session was over? I didn't want this to end.

"Restraint time?" asked my teacher.

I nodded, only relieved that the session was not over.

"Take off your satin shoes."

I untied the silky ribbons and removed the cute little satin shoes. I watched as my teacher pulled a large black wooden box from beneath the bed. It was six foot long, two feet wide, maybe eighteen inches deep and shaped somewhat like a coffin. A series of hinged doors on the top were opened to reveal a padded inner area in the shape of a person with wooden separators at the neck, chest, waist, knees and ankles.

I watched as the wooden separators were removed and laid to one side.

"You will be locked in the box," she explained.

I stared at the box, frozen by the surprise. As I processed the idea, my teacher had collected items from the second wardrobe. She returned with the pink leather heeled ballet boots I had worn previously. She slipped my feet into place, pulled the laces slowly tighter and tighter before being tied off in large bows. Straps were secured around my ankles and I heard the click as she locked them in place.

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