50 Shades Of Pale Pink Sissy

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A girly boy finds her submissive place in life.
19.6k words
4.45
217.2k
145

Part 1 of the 3 part series

Updated 10/03/2022
Created 06/03/2013
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davine
davine
231 Followers

A warm spring breeze ruffles my short skirt and my long auburn hair. My white stilettos click on the pavement as I walk to work. Hearing them always makes me smile, as does the delicious feeling of my nylon clad thighs rubbing together as I walk. My pale pink skirt is flared and very short showing off my shapely legs. When clubbing or shopping I wear sexy stockings but for work skin toned panty hose is more practical. A light cream camisole covers my skimpy push up bra which creates a little cleavage between my small breasts. I use a little dark foundation in the cleavage which makes it look larger against my milky skin. I'm wearing a pair of gold hoop earrings and a pink hand made beaded necklace. My makeup is perfectly applied as I was taught during my cosmetics classes. Pale pink lipstick matches my nail polish.

How marvellous it is that I have come so far in the five years since I left school. I have my own flat near work. As a qualified hairdresser I work in a salon that caters almost exclusively to the gay community. The salon is part of a huge chain called "PINK" that has outlets in every part of the country. I have heard that the whole operation belongs to one man but is only a small part of his global empire.

Let me tell you a little about me. I'm a twenty one year old girl (almost) called Antoinette (Tony) Hazel. I was born a boy (Anthony Hazel) but have felt and looked (mostly) like a girl for as long as I can remember. Later in this tale I shall detail my childhood experiences that led me to these events. I have always been small for my age. I'm only five foot five high and weigh about ninety pounds. My shoulders are narrow, my hips are wide and my bottom is round and soft. After puberty I developed small breasts with large areolas and nipples. Unfortunately, instead of a vagina I have been cursed with a tiny penis and testis. Being so small they are easily hidden between my legs and held in place with a tight Lycra thong. My testosterone levels are so low that I grow very little body hair and no facial hair. As you can imagine, my school life was hell. I was bullied incessantly by the boys and often only the protection of some of the girls saved me from real damage.

Every one commented all through my childhood years on how pretty I was which pleased me even though I didn't really believe them. Knowing that I was really a girl from a very early age I never played with boys toys preferring to borrow my older sister's dolls. She is six years older than me and loved to dress me in her old clothes that she had grown out of. Dad died when I was very young and mum was quite happy to let me be a girl while at home.

Arriving at work early as it's my turn to open up I'm surprised to see the lights on. As I step inside the salon manager David minces out of the office. He is wearing his usual androgynous look of tight slacks, girly tee shirt and a little make up.

"The owner is waiting in the office and he wants to see you" he whispers. Hell what is this all about. My heart is beating hard and fast with panic. I have heard that Mr Black can be very hard on his employees.

"Miss Hazel, if that is you I want you here now". Mr Black shouts from the office. Walking as quickly as possible in the stilettos I trip as I pass through the door. Strong hands catch me and help me to stand upright. He steps back to look at me. In front of me is the most beautiful person of any sex that I have ever seen. He is tall (over six feet) with broad shoulders and narrow hips. Black jeans hug his legs above stylish loafers. His shirt is tailored so that it shows his chest and arm muscles. His face has perfect chiselled movie star features under an unkempt mop of blonde hair. He looks nothing like the mega rich tycoon that he is purported to be. Smiling, he looks me up and down. My heart beat rises again and I have a strange feeling in my tummy and between my legs. Hope I don't faint.

"Turn around" he orders. I comply of course. After what seems to be a long time. "Perfect" I think I hear him whisper to himself. "You may turn back". Pointing to a chair he says "sit".

I ease myself into the chair holding my skirt down and demurely cross my legs. "Do that again without touching the skirt" an order that I obey immediately. Now, I'm trying to sit demurely with my skirt barely covering my panties. I feel the blush spreading from my chest into my cheeks.

Smiling he says "Much better. You have great legs so don't hide them from me".

"Ok" I mumble. My eyes are gazing at the floor.

"NOT OK! Yes sir is the correct response to your boss". He snarls.

"Yes sir" I manage to whisper with my eyes averted. I'm both terrified and attracted to this man.

"Much better, I have a proposition that I would like you to consider. But before you hear the details I would like you to have dinner with me this evening". He is smiling wickedly as he says this. Fear wells up from my chest and bursting into tears I stumble from the room and lock myself in the toilet where I sit and sob my heart out.

A knock on the cubicle door is followed by David's voice. "What's the matter Tony?" he asks. "Mr Black wants me to have dinner with him. He thinks I'm a real girl and he'll hate me when he finds out the truth". I sob. "Don't be silly. He has seen your personnel file and knows what you are. He wouldn't want a real girl." He laughs. "Now get out here, dry your eyes, fix your make up and get back to him before he changes his mind"

My heart is pumping, legs are rubbery and there is a strange fluttering below my tummy. Quickly I dry my tears and repair my tear ruined make up. Wow this is exciting beyond anything I have ever imagined could happen to me. Shyly I enter the office. Mr Black looks up from his papers, smiles and points to the chair. I automatically hold my skirt as I sit. His smile disappears until I stand and sit again with the skirt riding up my legs.

The smile returns. "You must learn to stick to my rules if you wish to progress in my company. I have ways to ensure that my wishes are catered to. You will learn that there are consequences if I'm displeased. Do you understand?"

I don't' but I answer "yes". His eyes narrow. "Yes sir". I quickly correct myself. "Will you have dinner with me"? He asks sternly.

I say "yes please sir". And the smile returns. I feel an ache of desire welling deep inside me that is both disturbing and thrilling.

He gazes at me. "I have decided that you can have the day off to prepare for our date". Date! There is the flutter again. "You will go to this address "he passes me a card "they are expecting you and will supply your entire outfit for the evening. You will be picked up at precisely seven PM. Don't be late. Have you any questions?"

"No sir". I whisper as I stand. He ushers me to the door and slaps my bottom as I leave. I feel electricity flow from his hand to the depths of my soul.

Grabbing my bag I almost skip through the door and onto the street waving to the boys as I leave. I can't believe this is happening but shake any doubts as I head for my appointment which is only a block away. I find the place which is on the second floor of a new office block. It is called specialist outfitting. Through the door I find a receptionist behind a desk who ushers me through a door and into a spacious room occupied by a middle aged woman waiting on a lounge reading a fashion magazine. "Make sure we are not disturbed" she tells the receptionist who leaves us alone. To me she says "Go into the next room and remove every thing bar your panties." I hesitate until in a stern voice she tells me to hurry. "I will be with you in five minutes".

I scurry into the room and find a small change room. The rest of the room has racks of hanging clothes and lingerie. There are rows and rows of spectacular shoes lined up along shelves on one wall. I quickly strip off my clothes and hang everything on hooks in the change room. There is a chair which I sit upon waiting for the next part of this amazing day to start. I hear footsteps which I presume are from the woman as she crosses the room.

"Get your arse out here missy so I can see what I have to work with" she says sternly.

Sheepishly I walk out of the change room with my hands covering my breasts. I'm so embarrassed that I keep my eyes looking at the floor. I stop in front of the woman who is much bigger than I. Grabbing my wrists she pulls my hands away from my chest and places them on my head. My chest and cheeks are flushed red."Don't move: or I will spank you" she snarls. Slowly she circles me. I feel like I'm in a cattle market being inspected for sale. When she is back in front of me she reaches out and lightly touches my nipples which spring to attention. Although I try to hold still I flinch at her touch. Walking quickly behind me she slaps my bottom really hard. It's all I can do not to burst into tears.

My tormenter walks to the shoe rack and selects a pair of stiletto sandals with impossibly high heels. They are silver with platform souls which will make me at least six inches taller. They are the type of shoe that only a stripper or pole dancer would be seen in. I am led to a chair where I sit and try them on. Standing, I find them reasonably comfortable. The bitch indicates that I should walk around to try them out which I do and find that I can walk easily in them. She leaves me standing in the middle of the room while she selects a pale pink corset from a rack. Wrapping it around me she proceeds to do up the clips that close the garment from the front. It is very tight with only quartes cups which push my little boobs up but leave my nipples exposed. Next she passes me a matching Lycra thong of the same style as I am currently wearing indicating that I should put it on. Quickly I slide mo current one off and try to get into the new one before she spies my little things. Trying to get them on while still wearing the shoes I trip and flop on the floor. The bitch giggles as she sees how small I am. I blush a brilliant shade of crimson as I try to regain my dignity and pull the new panties up and tuck myself away. Next I'm allowed to sit while I take the shoes off and slip into a pair of shear seamed white stockings and fasten them to the suspenders attached to the corset. I step back into the heels and admire myself in the mirror. I look hot in a bridal kind of way.

Bitch is still laughing as she selects a tiny white dress for me. She passes it to me and I slip out of my shoes and daintily step into the dress. I slide it up over my hips, slip my arms through the spaghetti straps and settle it into place. It hugs my every curve like a second skin. The hem is barely an inch below my lacy stocking tops. The material is so light that it is almost transparent. My underclothes are clearly outlined for all to see. Over my breasts the material has a different texture which rubs and stimulates my nipples which become erect and push out provocatively. Now I really look hot in a tarty starlet sort of way. My inner minx is doing hand stands.

"That will do. Your boss will be happy with that look. You are a lucky girl. Take it all off and get back into your clothes." Bitch commands.

I quickly bolt to the change room and carefully remove my new outfit and dress back in my work clothes. The bitch takes my outfit and carefully packs it into a box which she hands to me. "There is some other stuff in there that you need to check out as soon as you get home. Make sure that your make up is a bit over done as he likes that. And carefully read the note he has included with your gifts. You should run along now and start your preparations. Trust me; you don't want to be late". She smirks as she ushers me to the door. She slaps me hard on the bottom as I pass through the door. What is all this bottom slapping and spanking all about, I wonder as I clatter down the stairs to the street.

As its only two blocks to home I decide to walk. Although I'm apprehensive of what the night will bring my heart is happy and my belly glows deep down with anticipation. I'm having dinner with the most handsome man in the world. Wow! At the local deli I buy a couple of sandwiches so I don't have to waste time preparing lunch. I want to spend the time preparing myself to perfection for Mr Black.

Into my flat I race and quickly open the box which I see contains two smaller boxes and an envelope with my new outfit. After hanging the clothes up I open one of the boxes. Packed in tissues to protect them are a small jewellery box and a bottle of Chanel Number 5. Inside the box are dangly silver earrings shaped like an S, a necklace with a large silver S hanging from it and three bracelets with Hanging Ss. I open the other box.

Inside is an enema kit with instructions. Hastily I put it to one side as I'm not sure I want to go there yet. I'm blushing. What does he want from me? My bottom has never been invaded by any thing larger than a finger. This is scary.

I open the letter and read. "Thank you for agreeing to have dinner with me. I hope you like the presents and the clothes. Using the enema kit is optional but recommended as it may make your evening more pleasant. I leave that decision up to you but I do like my girls clean both inside and out. If you have questions please ring me on the number provided. That perfume is a stop gap brand for now. If you decide to take up my offer this evening I'll buy some expensive stuff to replace it. I look forward to enjoying your company this evening." There is a mobile number at the end of his letter.

I can hardly breathe. My heart is pounding with fear but deep down I'm excited. I finally calm down enough to ring him. "Hello Antoinette". Sugar! He knows my number. "Thank you for all the gifts Sir" I say. "I'll even use the scary one if it pleases you. Please be gentle with me as I'm new to that kind of thing."

"I'll be careful. Pleasure often requires pain as a co-conspirator to reach fulfilment. I am so glad that you wish to please me in this way"

"I had better go sir as I have much to do for your pleasure" I hang up.

Having plenty of time I eat my lunch and drink some water. After stripping I examine every inch of my body looking for stray hairs. I find a few around my hated boy bits and near my bottom. Using wax strips I'm soon rid of them. I decide to leave the internal cleansing until just before my shower which will be late afternoon. After washing and drying my hair I have to decide how to style my long auburn hair. I could do a pony tail or pig tails to make myself look younger and more innocent. Or even girly ringlets. Maybe that would slow him down. Or it may just fire him up to ravish me. Anyway that look wouldn't fit in with the slutty outfit. How about I wear it all piled on top in a sophisticated evening style. No, I don't want to look too experienced. Perhaps I should ring him for advice. That may be too forward. I decide to curl it a little and wear it down around my shoulders like your typical normal girl about town. That shouldn't send too many messages to sir. By the time my hair is finished I have a couple of hours to be ready.

After reading the instructions I go about cleaning the inner woman. I won't go into details but just say that by the time I finish everything is flowing clear. Putting a shower cap on I wash myself thoroughly with scented body wash, dry myself and spray a little Chanel onto my neck, breasts, wrists and tummy. I smell heavenly. Taking the corset I wrap it round me and do up the hooks at the front. I have to breathe in to close it as it is very tight. I settle my little breasts into place and sit down to slide the stockings up my smooth legs. Standing, I make sure the seams are straight then hook the suspenders to each lacy stocking top. I slip into the matching thong and tuck my bits into place between my legs.

At my dressing table I do my make up. I go much heavier than usual with foundation, mascara, eyeliner and blusher. I finish with very bright glossy lipstick. As I am putting my jewellery on I realize it is nearly pick up time. I guess that the third bracelet must be for my ankle. I slide into the dress and slip into my stripper shoes. Even though I know I'm late I check myself in the mirror. I look so hot. Throwing my make up, brush, purse and perfume into my hand bag I scuttle through the door and down the stairs. I arrive on the footpath in the twilight at five past seven. Sir is waiting for me about fifty meters along the street standing next to a low slung black sports car. It looks like a racer to my non technical mind. My heels tap on the pavement as I sway along the street. Most of the people on the foot path stare at me and I hear some quiet whistles as I pass. He is frowning as I approach. I know I'm in trouble. Grabbing my wrists he bends me over the roof of the low car, hikes up the hem of my dress and plants a hard spank on each bare buttock. I gasp in shock and pain at the assault on my exposed bottom but I manage to hold back the tears.

Opening the door he pushes me backwards into the car. My still exposed bottom sinks into the seat. Many of the pedestrians are staring at me. Sir guides my head so that I don't hit it on the roof. I daintily slide my legs into the foot well. Sir passes the seat belt across me and clips in into place. After a quick kiss on my forehead he closes the door, walks around the car and settles into his seat. I glance at Sir as we drive off. He has a broad grin on his face. "Sir" I ask "why are you smiling". He laughs "you didn't run when I spanked you which tells me that there is a high chance that my after dinner offer will be accepted" he answers.

Although my bottom smarts I feel excited that he is happy with me. I wonder if I can put up with some pain if that is the price I pay for the pleasure I'm feeling just to be with him. He drive forcefully out of the city and heads towards the Eastern Suburbs where I know there are many big houses. Soon we pull into a driveway that takes us through manicured gardens to the forecourt of a huge mansion. Two limousines are parked there.

I wait until Sir helps me out of the car and I pull my skirt down over my bottom. He doesn't seem to mind. Taking my hand he leads me to the tall double doors set into a pillared entrance portico. The door is opened by a tall French maid of ambiguous sexuality. "Welcome Sir" she says and curtsies. "Thank you Suzy" he replies and leads me along a vast hall way, through a doorway and into a vast room furnished with comfortable chaise lounges, coffee tables and various single chairs. Fine painting adorned the walls and Persian rugs are scattered over the polished timber floor. There are four people in the room. Two are dressed in black and are seated at either end of a chaise. At their sides each had someone dressed in white kneeling on the floor holding a tray. As we approached the two seated figures place their glasses on their tray and stand to greet us. One is a tall woman dressed in black thigh high boots over tight black form fitting tights, a white silk blouse and leather jacket. Her tray holder who has stood up and holds the tray near the woman is about my age and size. She is very pretty with long auburn hair, lots of make up and wearing a long cloak tied at her throat with a chord which covered her completely apart from her wickedly high white stiletto pumps.

The other is a tall muscular, blond man in tall black riding boots, black jodhpurs, brown shirt and military style coat. His companion is a very pretty auburn haired boy who has also risen to keep the tray nearby. He too is wearing white stiletto pumps. Instead of a cloak he is wearing a white lace body stocking which hugged his body perfectly and a short skirt for modesty. Both of the companions keep their eyes looking at the floor. His face is made up in a similar manner to the girl and mine.

davine
davine
231 Followers