Andrea's Beginnings

by Candy Heels

 

Part 2

 

Andy hardly slept Friday night. The anticipation of visiting Ms. Robinson at her home was overwhelming. Why had she been so nice to him when she had caught him wearing her pumps? She had even taken time to help and teach him to walk nicely in high heels. She had not ridiculed him at all – not like his mother had done so many times when she had caught him wearing her shoes.

He had told his mother that he had to complete a school assignment and left the house about 8:30. As always she had been cruel in suggesting that had he completed his work during the week, his weekends might be his own. It was only a few blocks past the school to her home but many times he thought he should turn and run; to hide; anything to avoid the pain he would know and the shame he would feel when she told the world what he had done.

Nevertheless, at 9:00am he rang the doorbell of her home. She lived in a very upscale townhouse – not at all what he expected when she referred to her home as an apartment. He felt such deep panic but it got so much worse when he began to hear high heels clicking on tile floors and approaching the door.

He was mesmerized; never had he seen her like this. He long black hair was tied with a white ribbon in a pretty ponytail. She wore lipstick but little makeup otherwise but her face was as beautiful as he had ever seen. She wore a white halter-top showing her slim bare midriff and a white short skirt almost like those he had seen girls at school wear to play tennis. She wore no nylons, he could tell because the low cut U throat of her white patent pumps showed the base of her toes. The heels were stilettos as always and magnificently high. He could swear they were a little higher than those she wore to school everyday.

Her face lit up with a lovely smile and she said, "Oh I am so glad you came, I was afraid that you might not. We have so many things to do and I do hope you enjoy what I have in mind."

Andy just blushed and said, "Good morning Ms. Robinson. You look so pretty."

She opened the door wide and with a large warm smile, she invited him in. She asked him to the kitchen. Following her was so exciting. How could she walk so easily, so gracefully wearing heels so high?

She poured orange juice for two and made small talk about school. As he drank his juice he admired her beauty and then she shocked him somewhat. She just stopped and said, "Well we have a great deal to do today so I want you to go shower and wash your hair. Before you shower put this cream on your legs and arms. There is a robe and slippers in the bathroom for you to put on afterwards and then I will meet you. Please wear nothing but the robe and slippers and do not dry your hair please; just wrap it in a towel."

Andy just loved to do as she asked, "Yes Ms. Robinson – I won’t be long" and he went upstairs to the bathroom. He did not know why but visions of terry cloth robes and fuzzy slippers that make your feet look huge came to mind.

When he entered the bath it was so obviously her; so feminine in every way. The colors and her scents overwhelmed his senses. He saw neither robe nor slippers but he was in a hurry to do as she asked. He stripped naked and spread the cream on his legs and arms. It smelled so pretty and he wondered what it was for. The shower felt so nice. He washed his long and usually stringy hair with her shampoo and he noticed that what little hair he had on his arms and legs just washed away with the cream.

When he stepped from the shower to dry, he noticed that his clothes and running shoes were gone. Hanging on the door was a pink satin robe that was very short and standing on the floor was a pair of stiletto heel slippers – mules with 5" satin heels. The toes were open and were covered with huge pink marabou accents. The insoles looked like soft satin.

Andy dried his body and wrapped his long blonde hair in a towel. He put on the robe and tied the pink satin sash. God it was short. It barely covered his bare bottom and privates. Oh God he thought. Did she really want him to put on her slippers? He held the door for balance and slipped one foot into the toe of one slipper. They felt so soft and so high as he rose and slipped on the other. What heaven he felt – they fit so perfectly and the soft marabou and satin soles caressed his toes. And the heels – they were so high – there was that same wonderful feeling of being on tiptoe in beautiful heels. He could feel stirrings in his loins and the short robe was not helping his dignity.

She called "Andrea, are you dressed? Come here please – we have a lot to do"

He thought – Andrea????????? He was very embarrassed but he liked it. He simply said, "But….". She said, "Come here please – we have a lot to do yet." The walk to her room was difficult. The carpet was different than the tiled school floors upon which he had first worn heels this high and he also realized that mules provide far less support than her pumps. It was a heavenly feeling though. What wasn’t heavenly was now his very rigid member trying to poke out around the short robe. She again told him to hurry so he walked into her room trying to hold his hand in such a way as to hide his excitement.

She said, "You look so lovely and my slippers fit you perfectly. Do you think they look pretty?"

He said, "I love them. They are so high too. Do all your shoes have high heels?"

She said and shocked him with the "we", "Oh yes, we must never wear anything but high heels. They are so elegant. Now let me get some rollers in your hair. Sit here."

Thank God he could sit – not because his high heels were uncomfortable but she might not notice his thing. She stood beside him and deftly added rollers to his hair. She snapped some lovely pearl earrings on his earlobes and then said "I think I will do your nails before I do your makeup."

His fingernails took a little while. Acrylic nails were lovingly applied, shaped and then she painted them red. She then knelt to do his toenails and slipped off one of his high heeled slippers and said, "hold your slipper while I do your toes but be careful – your nails might not be completely dry." This was so exciting that without warning it just popped out. She said, "Oh goodness – you do like being pretty don’t you. But we cannot have this thing ruining the lines of your skirt later. I can help."

She knelt beside him. The pointed toes of her white patent pumps in the carpet. He could see the long white stiletto heels extending her slim ankles. She took the slipper her was holding and began to tease his thing with the soft marabou toes. God it felt so good – but she lowered her head and took all of him deep in her mouth. He almost died with pleasure. She only needed to suck him a few seconds and he exploded deep down her throat. She smiled and said, "There that’s better" and looked as his throbbing member slowly became quite small again. As if nothing had happened, she placed cotton between all of his toes and quickly painted them all a deep lovely red.

She said, "I will dress while your hair and nails are drying and then we can do your makeup."

He sat and watched as she combed out her hair and prepared her makeup with such beauty and ease. A few brush strokes to her skin and pencils to her eyes and she went from a beauty to a Goddess. He sat transfixed as she wiggled out of the halter-top and skirt. She was wearing neither bra nor panties. She walked naked in the white stiletto pumps to her chest of drawers and removed 2 black basques. One she lay upon the bed and the other she put on. It was gorgeous. It had garters and a lacy bodice that cradled her wonderful breasts. From her drawer she took some sheer stockings and almost carelessly kicked off her high heeled shoes. It was the first time ever that Andy had seen her tiny bare feet. Then he realized that they were the same size as his tiny feet.

She rolled her stockings up her legs and fastened them to her garters. She did not put on any panties so he could see her bare bottom when she bent to pick up her white high heeled pumps and she opened the door to another closet. My God he thought as she revealed in this closet hundreds of pairs of shoes. They all had very high stiletto heels, many of them much higher than he had ever seen her wear at school. She placed the white pumps in an open space on the shelves and selected a pair of black stiletto pumps with a burgundy spike heel. The toes were very pointed and had a toecap the same color as the heel. She set them on the floor and stepped into them with ease. She closed the closet of shoes and walked to another door, which turned out, to be a walk-in close full of colourful dresses, blouses, and skirts – seemingly endless lovely things. She selected a blouse the same color as the heels of her pumps and a black straight tailored skirt.

She pirouetted in from of a full-length mirror and said, "That will have to do." She smiled a huge warm smile and looked at him and said, "Your turn."

Without letting him see in the mirror, she combed and styled his hair and applied some cosmetics to his face. He could not see his hair but the normal strings of blonde seemed to be large soft and very sweet smelling curls. She helped him into his basque and placed some breast forms into the bodice. She then took a pair of very sheer stockings from her drawer, which she then rolled up his legs and fastened to his garters. It was a new feeling that he loved and his thing began to stir again. She smiled and stroked it as she said, "I will get something to hide that for the next time but today you’ll have to wear petticoats and a full skirt to hide that. I cannot be sucking it soft all day long."

She helped him step into a lacy petticoat and then had him slip his arms into the sleeves of what seemed to be another robe. It was like a slave girls dress in a lovely dark blue. It buttoned down the front and had a normal collar. She fastened a wide belt around his waist. The combination of the basque and the belt really gave him a lovely figure. She looked thoughtfully at him and then smiled as she tied a silky dark blue sash around his neck and styled it like a pretty bandana. She raised the collar of his dress and said, "Almost done, I just have to find the right pair of high heels for you to wear". He laughed to himself as he thought, "How could a pair of high heels not be right".

She walked to the closet and took a pair of high heeled slingbacks. They were very dark blue patent leather with a high stiletto heel seemingly higher than he had seen yet. They had a toe style much like her slippers with a large white rose attached to the open toe. Except for a very narrow strap that would go around the back of his foot they were totally open.

She had him sit as she slipped his toes into the soft insoles and he could see that the open toes were going to display his lovely red toenails. She raised the straps behind his ankles and said, "I apologize, these heels are higher than you are used to but I think you will find them very comfortable when you adjust to the heel height – and besides, they match your dress perfectly."

Andy said, "Oh God they are so pretty. The straps are snug but they feel so nice."

She said, "Alright, let’s go see what you think of your new look."

She rose as did he and she led him to another room. Walking with her in these heels was pure heaven. He could feel the tug of his garters; the sheerness of his stockings; but best of all was these high heels. He could feel the extra height of the heels – he did not know they were 5 ¼" but with every step he remembered her teachings and he felt that he was walking nicely. It was heavenly when she said, "You are starting to walk with a lot of grace in high heels. You are learning so well and so quickly, Andrea." She giggled, "You are actually wearing higher heels than me today."

They entered a room and he saw his reflection. Gone was the skinny little high school boy. Before him was a beautiful and fashionable young woman with a lovely figure, a very pretty face and lovely long legs with very slim ankles. He stood and looked at himself in shock! He was beautiful; even his stance and mannerisms reminded him of what he had admired in her.

She said, "I almost forgot." And she handed him a small clutch handbag that was a perfect match for his high heels. She explained how he should hold it. He saw his feet in the mirror. These high heels held his arches vertically and he thanked God for the full skirt and petticoats because they hid his excitement so well.

She looked and said, "Well Andrea, you look so lovely. I think you shall be my little sister so you better call me Sarah. We have to go out now. There are a lot of errands we must do together."

His mind went numb. Go Out??????? As a woman?????????

 

To be continued

 

 

 

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© 2002 by Candy Heels. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.