Andrea's Beginnings

by

Candy Heels

 

Part 5

 

"Andy, could you please try to pay attention."

Miss Robinson had awakened him from his day dreaming again. It was Thursday and it had been a particularly difficult week for him. All he could think about was his experiences with her that previous Saturday; what heaven it had been and why she had seemingly ignored him ever since.

"Andy, I would like you to stay after school."

He thought to himself if I am going to get punished, I may as well dream about what had made me happy.

After their trip to the pool, she had given him a lovely nightgown to wear with his slippers and they had shared a salad. Afterwards, she said that she felt the need for a short nap and that he should do the same in her guest room. He was so excited and happy that he did not think he could sleep but he did lie down upon the soft comforter and spread the nightgown so that he could see his pretty feet in the high heeled slippers.

He had drifted off to sleep and as 6:00 pm she awakened him gently.

"It's time to get ready for the party so I would like you to bath again so I can do your hair and makeup."

He showered and returned to her wearing his silk robe and high heeled slippers. She was waiting at her vanity wearing a lovely black robe but she was barefoot and had cotton between all of her toes. She laughed,

"My goodness, I cannot get you out of high heels for five minutes can I!"

"I am sorry. You know how wearing high heels makes me feel. It's so special. I want to wear them forever."

"It's quite alright. I think I know how you feel. Just sit here so that I can do your makeup and hair while my toenails dry. Then I can get myself ready."

She styled his hair and spent a lot of extra time around his eyes as she did his makeup. When he finally turned to look in the mirror he was shocked. Not only was he pretty but this makeup was so sexy. She had highlighted his eyes so that he looked very alluring and the way she had created large waves of his blonde hair curling onto his cheeks and brow, he had to admit that he could not only be very pretty but he could be very sexy as well.

He put on his very special panties and then a black tightly boned basque that shaped his waist. After inserting his breast forms, she helped him put on black seamed stockings. She was so careful to show him how to make sure the seams were straight. This was another new experience that was making him feel so special and he was thankful for the special panties because he was also very excited.

Then she brought the dress she had selected for him. It was black velvet and very tight. She helped him put it on and did the choker collar up for him. The skirt portion was very tight and ended three inches above the knee. The front was also tight and rose from the waist to show bare arms and was low backed – right to the top of the bra portion of his basque. His bodice was covered by the front of the dress and fastened at the neck with a choker style collar. She completed the dress with a single strand of white pearls. As he looked at himself in the full-length mirror, he felt so lovely; this was an evening dress. She giggled as he stood up on tiptoe to pirouette and admire his look.

"Why don't you go into that closet and choose a pair of black shoes while I get dressed."

His mind exploded. Never before had he been allowed to select his own high heels. As he stepped back into his slippers he said,

"Thank you for helping me do this. This is really a dream come true. I do not know how but I feel that I know that I want to live like this."

"We can talk about that later – go pick out some evening heels."

He had enjoyed glimpses of the inside of this walk-in closet but he was overwhelmed when he went in. There were hundreds of pairs of high heels of all colors and styles but with one common thread – they all had stiletto heels and they were all very high. But in the back, he found a table with high heeled pumps that were higher than he had ever seen. She had never worn any of these to school. He took a black patent pump and compared the heel against his high heeled slippers. The heel was at least an inch higher. These he thought must be six inch heels and she had many pairs of them. He looked through the table and found a pair of pointed toe black patent pumps with these magnificent heels. The also had large patent bows on both the toe and also on the back of the pump.

He was so excited about wearing these. There was a small silk covered chair in the closet and he sat to put them on. They were quite snug and it seemed hard to get his toes curled up and into the toes of the pumps but once he had them both on, they were very comfortable despite how much his toes had to rise in these high heels.

He was so excited about showing Sarah the heels that he had chosen. He stood to walk back to her bedroom and almost fell down. What could be wrong? He had worn her regular high heels very gracefully and while he could walk with very short steps, the extra inch of heel height he was wearing seemed to make being graceful very difficult. He was determined to wear these heels so with determination, he walked carefully into the bedroom to wait for her.

He was standing trying to make his feet and legs relax when she entered the bedroom and smiled at him in a scolding way,

"How did I know that you would choose a pair of my ultra-heels? You will adjust to those eventually with practice but they are far too high for what we are doing this evening. I do have to admit though that you do have the legs and arches for six inch heels. I will select a more suitable pair for you."

He felt a small pang of disappointment although he had to admit to himself that he did not feel at all at home in these heels. In the mirror, his arches looked so fabulous and he enjoyed posing but what good would that do if he looked clumsy? There were so many challenges yet to overcome to become the woman he was dreaming about.

She returned with a pair of black suede Dorsey pumps. They had very pointed toes and a thin stiletto much the same as the blue sandals he had worn downtown. They were only very slightly higher than his five inch slippers. What made them so sexy the absence of the sides on the pumps. She inserted the small pads into the toes and had him put them on. The backs had to be spread a bit to get the back of his foot into them.

"The backs of Dorsey Pumps are tight. Because the shoe has no sides, they have to be or they would slip when you walk."

These heels felt like heaven. They were wonderfully high but they were not so high that Andrea could not walk easily and gracefully and he loved how they matched his dress. She gave him a black velvet clutch handbag and said,

"You go downstairs and put all your identification and money in that bag while I finish getting ready."

Andrea was enjoying all the experiences and feelings when Sarah came downstairs. She was wearing a silver strapless evening dress that was very low cut and the tops of her breasts showed. It was almost floor length and very tight but it was also slit right up to her thigh. Andrea realized that every time Sarah took a step you could see almost all of her leg. She had worn no nylons, her toenails were painted crimson red, and on her bare feet, she wore silver open toe mules with high stiletto heels.

"The limo should be here now, I couldn't possibly walk those blocks to the school in this dress and these heels."

"You look gorgeous Sarah. I wish I had breasts so I could show them like that."

"You never know what the future may hold for you Andrea. It's time to go."

The dance was a dream for Andrea. All the people dressed so nicely and she had been allowed to help Sarah as the hostess of the reception. All her memories of this were so emotionally intense that they seemed to run into a kaleidoscope of feelings and joys.

That good-looking senior boy she met near the Mall had asked he to dance to a lovely slow tune. He was holding her firmly and nicely as they danced and was talking about things that young women and men share when he surprised her,

"You and your sister seem to always wear such high heels. They look so nice."

"Yes we prefer higher heels but we have many that are far higher than these."

Sarah appeared from nowhere and ruined everything,

"Andrea, its time we left. Your flight home is very early tomorrow and we need some rest."

The ride back to Sarah's home was quiet and sad but the hell for Andrea came when she had to return to Andy's life. Male clothes and running shoes for the walk home was so sad. Andy could not believe and could not accept that this day had ended. Andy cried almost all night.

"Andy, could you please not daydream!!!!!"

Suddenly it was Thursday again. Suddenly it was that mundane male life again and she was scolding him for losing track of class work.

"We really need to talk after school. You need to be focused on your work, Andy."

When everyone had left she closed the classroom door and locked it.

"It seems that our day last weekend had affected you to a large degree."

"Miss Robinson, that day was so special for me. I am so much happier as a girl. I love so much wearing pretty things and looking nice. I cannot stand being this way. I have been so sad this week wondering if I might ever get the chance again."

"You might feel better if you put these on."

She slipped off her beige stiletto heel pumps and handed them to Andy. He quickly kicked off his running shoes and socks and slipped on her high heels. Suddenly those wonderful feelings were back. He walked around the classroom enjoying those feminine sensations and the wonderful sound of his heels on the tile floor.

She smiled broadly,

"It seems that I will have to think of some arrangement for you. Do you still want to be Andrea and go that job you were offered at the Mall this Saturday?"

"Oh yes, I have dreamed about that. Please Miss Robinson, I really need to do that if you could help me."

"Well, you better be at my home about 7:30am to get ready for work and in the meantime, I will try to think of a way to help you achieve more time as a woman. It seems your time as a man is quite wasted."

 

To be continued

  

 

 

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