William and Harriet Complete

By Art Tole

The original book "William and Harriet" was just meant to be a "Walter Mitty" story of two sexually frustrated people. This book continues that to see what happens when they give freedom to their fantasies. It includes Dr. Kristin Braxton who appears in other stories that I have written. She helps two soul mates deal with the problems they created when they decided to switch genders in this lifetime.

• Language: English
• Publisher: Art Tole
• Release date: Aug 27, 2016
• ISBN: 9781370044108

Book preview

The sun was shining through the window when William was nudged awake by the movement of Harriet next to him in bed. When his eyes opened he saw her smiling and felt her hand on his cock. Weekends were great for sleeping late and other things. No pressure on either of them to get up and get ready for work. He smiled and stretched to hide the apprehension that he felt rising within him, what if I can’t get hard; it hasn’t been working lately? He slipped down and kissed her breasts; she purred with delight and he gave them his full attention. With his free hand he stroked the inside of her thighs and her pussy until he felt her getting wet. His cock slowly rose to the occasion but stopped short of a full erection and when he felt Harriet’s hand on it he knew that she knew there wouldn’t be any orgasm today. Not for her anyway. William apologized and turned away from her.

With a sigh Harriet said, It’s alright William. We have to get going anyway; I have a lot to do today. Sunday was her favorite day to shop and after looking at the ads in the Sunday paper she got dressed and was soon ready to go.

Come on William, hurry up, I have a lot of things to do today, Harriet kept looking back at her husband. Bloomingdales was having a sale and she could sense a bargain in the making.

William was struggling with the two bags of bargains she had found at other stores, but he smiled and said, I’m right behind you dear. Dutifully he stood by as she worked through the racks of clothes and shoes. She left him standing in the middle of the women’s department, holding her purse, while she went to the dressing room to try on several outfits that she had found. Left alone with nothing else to do, Billy was studying a manikin that had been placed on a low platform. It had been dressed with a short, sexy cocktail dress. He liked women’s clothing, he liked women, but he really liked wearing women’s clothes. For as long as he could remember there had been an attraction that he never understood. His earliest memory was around the age of three; playing with his mother’s shoes. She had laughed at him as he tried to stand in her high heels. He used to hang around her when she was getting dressed. Watching her put on her bra, girdle and hose was his favorite past time. When he could he wore his mother’s clothing; it became easier when he was old enough to be at home alone. As he grew older he realized that there was a boundary that he was not supposed to cross; so he only played with her clothes in secret.

Shopping with Harriet was something that he secretly enjoyed; it gave him a reason to hang around in the women’s department. She didn’t realize that of course. The cocktail dress on the stand in front of him was beautiful and he was imagining himself wearing it when he was surprised by the sound of a woman speaking to him.

Yes, it would look good on you.

He turned around to see a tall, middle aged woman standing behind him and to his right. I beg your pardon? he said, pretending that he hadn’t heard her the first time. He had heard her of course, but he didn’t understand how she knew what he had been thinking.

Would you like to try it on? We are busy today, no one will notice. Your wife will be busy for at least 20 minutes trying on all those clothes. Come on, I’ll put you in one of the fitting rooms, we can pretend you are with your wife. She turned and motioned for him to follow her.

He hesitated, looked around and then followed after her. She was dressed in a black, long sleeved dress with an extremely tight skirt that reached down to the middle of her thighs. The black, shiny, six inch high heels gave her a height that exceeded his by at least four inches. Her long straight, black hair was cut off square across her back and pulled back from the square cut bangs of her face. The four inch long, silver earrings with a matching necklace framed her face and her ice blue eyes gave her a cold authoritarian look. No one seemed to notice as she led him to a fitting room; one of the larger ones with a door, not a curtain. He looked around at the room that was empty except for two straight backed chairs with red padded seats and a full length mirror. Billy was nervous now, Maybe this isn’t such a good idea.

Ignoring what he was saying she said, I’ll be right back, then turned and walked out, closing the door behind her.

Billy stood where he was for a full minute and then said out loud, This is stupid. Harriet must be done by now. As he reached for the door knob, it turned in his hand and he stepped back.

Is something wrong Billy? She was back and she had the dress over her arm as well as some other items. Take your clothes off, she said with a smile. He hesitated which prompted her to step closer to him. Towering over him she commanded, NOW!

Billy jumped, Okay. He quickly peeled off his clothes and she began to dress him. She had brought a padded girdle and a padded bra with her and some nylons to go with the girdle. She helped him step into the cocktail dress and zipped him up. Amazingly it fit perfectly. She gave him some six inch high heels to wear and earrings to complement the dress.

You look great Billy; here let me help you with some makeup. He started to argue but his protest was cut short by her stern look. A blonde wig followed the makeup and she announced, You are ready.

Surprised he said, Ready for what? I have to get out of this; Harriet will be looking for me. He looked at himself in the mirror and liked what he saw. He rubbed his nylon covered thighs together and let his hand rub his cock through the dress and girdle.

The woman slapped his hand and said, Don’t you dare stain that dress. Get your hands away from there. I have work for you to do!

Even in his high heels he had to look up at her, Work! What work? I need to get out of here. He stopped talking when she grabbed his lower jaw in one hand and squeezed his cheeks.

You are going to model that dress, she said threateningly. I took it off of the manikin so you will replace the manikin. Come with me. She took his right arm and forced him to walk with her. Staggering in the high heels, he was pulled along beside her, and was amazed at how strong she was. She led him to a round table like platform that stood about four feet above the floor and forced him onto the platform using a small step stool next to it. He found himself looking out over a room filled with women who were all looking at him. Stand still, she said and he felt a pole penetrating an opening cut into the seat of the panty girdle and poking at the opening to his ass. He squirmed and started to try to evade the penetration that he knew was intended. Stand still, she snapped again. Billy felt the one inch diameter pole slide into him and he fought to keep his balance as it forced him to stand with his feet together and shoulders back.

Looking around from his vantage point above them, he saw that all of the women in the room were smiling at him. With the thick pole buried deep inside him, he felt helpless and embarrassed. This can’t be happening. I can’t believe it and my cock is rock hard. I can’t masturbate in front of all these women.

The tall dark haired woman grinned and said, Now strike a pose like the manikin next to you and don’t even think about touching that lump in your panties. Billy did as she ordered and she said, Excellent, I knew that you would look great in that dress. I’ll be back in an hour to let you down, she turned quickly and walked away.

Okay William, I am ready to go. Here is another package to carry. Seeing no response she snapped, William what is the matter with you?

Wha...? Harriet was looking at him. He was suddenly aware that he was standing next to the table that still held the manikin. The manikin had the dress on, not him. Oh, I’m sorry dear, I was just thinking of something I have to do at work. Are you ready to go? She ignored the question, turned to leave and he followed her. He was also aware of a very uncomfortable hard on. A tall, stunning woman in a long sleeved black dress glanced at his crotch and smiled at him and as he walked past her on his way out of the store.

Chapter 2

Harriet was hanging her new clothes in her closet and thinking about William. She loved him but wished that he could be a more aggressive and take charge kind of man; especially when it came to their love making. She refused to call him Billy because she felt it sounded too submissive and child like. He was always kind and considerate, but she felt the need to either be dominated by a man or he needed to be dominated by her. She had worked her way to the top in her company by being aggressive. Her preference was to have women working for her; that left no question in her mind as to who was in charge. Men were different, she always felt that they were challenging her authority and she resented it. She paused from putting away her new clothes. Maybe it was a mistake trying to get William to be the kind of man she wanted as a husband.

She saw the sexy maid’s uniform that she had bought for Halloween last year, hanging in the closet. It was very unlike her personality and she didn’t enjoy wearing it although she got a lot of male attention with it. William, come in here please.

Can I help you with something dear? William stopped next to her and saw that she was hanging up her latest purchases, Your new dresses look great. Is that what you wanted to show me?

No William, this is what I want to show you, she held up the maid’s uniform and said, Put this on right now.

William looked at the dress and said, What on earth for? Why would you want me to put this on?

Harriet looked at him as if he had just asked the dumbest question that she had ever heard, You are worthless as a man, I might as well get some use out of you as a maid. She handed the dress to him, Hurry it up; put it on. I have work for you to do.

William looked down unable to meet her gaze, he looked ashamed because of what she had just said. He sighed and took off his clothes.

Go get the hair removal cream and remove all of the hair on your body from the neck down. Go on, hurry it up. Do it in the shower and then dry yourself off. I’ll lay out a few other things for you to put on also. Move, don’t keep me waiting, Harriet was losing her patience with him.

Twenty minutes later William stood in front of her freshly shaved and without a hair on the rest of his body. Blushing, he put on the padded bra and garter belt. Then he stepped into the maid’s uniform. It had puffy sleeves, a low neck line and a short flared skirt with several layers of petticoats under it. The skirt was so short that it barely covered his butt. William looked but saw no panties to put on. He gave Harriet a questioning look and said, Where are my panties?

Harriet was approaching him with a tube in her hand, You don’t need them yet. I still have to get rid of that useless piece of meat between your legs. Lie down and spread your legs.

William didn’t hesitate; it didn’t do any good to argue with Harriet when she was in this kind of mood. Yes dear. Do you mean like this? he lay flat on his back with his legs spread out but straight.

Pull your knees up. She took the cap off of the tube and held it in her gloved hands. She was wearing latex gloves and used her right hand to pull his dick down until the head was almost touching his ass hole. While William held the tube, she used the other hand to pull the skin of his scrotum up on both sides of his dick, trapping his flaccid cock between the folds of skin. Holding it with one hand she took the tube of super glue and glued the folds of skin together. She worked her way up until his dick was completely covered except for the head that was trapped near his ass hole. When she was finished she said, Stand up.

William stood in front of the mirror and raised his skirt. There was nothing there; it looked like he had a pussy where his cock should be. Harriet what have you done? What happens if I get an erection? I could hurt myself.

"You won’t be getting any more erections. I have been feeding you female hormones for the last four months. You were worthless as a lover. I haven’t had an orgasm since I married you. From now on I am going to teach you how women pleasure each other. You can quit your worthless job too. There is plenty of work for you to do around here. Put your nylons on and I’ll give you some pansy panties to wear. She handed him a pair of pink satin panties with ruffles across the back.

William finished dressing and slipped on the shiny black shoes with six inch heels. He looked at himself in the mirror and liked what he saw. Harriet saw the smile on his face and said, "That’s what I thought; you are a Pansy, with a capital ‘P’. You never should have been born with a dick. Get your makeup on and this wig. I can’t wait to get you started with the cleaning.

Twenty minutes later William stood in front of her looking very much like a sexy French maid. The first thing you will learn to take care of is my pussy. She sat down and pulled up her skirt. Her panties were already off and she spread her legs wide, Well hurry up and get busy cleaning it with your tongue. Hurry up clean it. Clean it.

William, who had just walked into the room, gave her a puzzled look and said, You said, ‘clean it’, what is it that you want me to clean? asked William, This dress? I can take it in tomorrow on my way to work.

Harriet seemed surprised to see him next to her, she handed him the dress from the closet and said, Thank you, I may have a few other things here that need to go in also.

Chapter 3

On Monday morning when Billy walked into the office area he saw three of the prettiest women in the office standing at the copy machine talking. Arlene was an Asian beauty who stood barely five feet tall even with the high heels that she always wore. Brenda was an average height blonde, blue eyed bombshell with the best looking boobs in the office. Charlene on the other hand was an all around gorgeous woman with red hair and green eyes. Everything about her was perfectly proportioned, except her IQ. If she had been blonde no one would have been surprised, but her red hair mislead people into believing that she was capable of at least rational thought. The women were having a very animated discussion as he walked by, trying not to look at the mini-skirts with perfectly shaped legs under them. He quickly disappeared into his office and pulled out the file that he had been working on when he left on Friday. After reviewing the work that he had already completed, he sighed and started to work. The work was boring and it didn’t take much to distract him. His thoughts turned to the three women that he had just seen in the office.

He wished that he could wear the clothes that they wore every day. He wasn’t gay; he just liked women. He admired them. Seeing a well dressed, beautiful, young woman was the high point of his day. He tried not to stare at them. The sound of his office door opening prompted him to look up as Arelene led Brenda and Charlene into the room. Arlene was the organizer of the office and if something was happening she was involved in it. Billy we need to talk to you. This is extremely important. Arlene had stopped in front of his desk and stood as straight as she could with her shoulders back, so that her boobs were pushed out. Her voice sounded like a little girl of ten instead of the woman of twenty-five that she was.

Hello ladies, what is so important on a Monday morning? He was admiring the three women standing in front of him and was surprised they had come to him about something because none of them worked directly for him.

We need you to be the judge. We are having a contest and the winner gets to wear this tiara for the rest of the week. She held up a rhinestone studded plastic tiara that women wore for formal occasions.

That sounds important. What kind of contest? He set his papers aside and stood up.

We want you to decide which of us you think is the best. Let’s start with our underwear, who has the sexiest panties? She raised her skirt and the other two women followed her lead. Arlene was wearing white lace trimmed red satin bikini panties.

The sight of the three women with their skirts raised took him by surprise but he quickly recovered and said, Arlene your panties are very nice. He looked over the desk at Brenda’s panties. Her panties were pale pink with small blue flowers as a band around the legs and waist. Charlene held her skirt higher as he looked her way, she had on a transparent thong that barely covered her pussy and gave proof to the fact that she was a natural red head. Well, personally I like what Charlene is wearing.

Charlene jumped up and down; an activity which challenged her bra’s ability to keep everything contained. Arlene said, Well that is just the first round. Okay Billy, which one of us has the best looking breasts? She opened her blouse and displayed a surprisingly large pair for someone her size. Her breasts were small but appeared large on her small body. Brenda and Charlene followed her example and opened their blouses too. Brenda was on the small side for her size and Charlene was well past the size that would be comfortable to use as a pillow.

Billy moved around his desk to get a better view of the contested items. Aware of the responsibility entrusted to him he examined each girl carefully. Finally he had to admit that, Arlene has the best looking breasts, without a doubt.

Charlene was pouting now and Arlene had the smug, ‘I told you so’, look on her face as she expanded her chest to give him a good view of her breasts. She said excitedly, The next contest is to see who has the best looking legs. She pulled her skirt well up above her ass again and turned slowly for him. Brenda and Charlene did the same as he looked at each of them in turn.

Brenda’s legs were fantastic. They were perfectly straight and well proportioned for her voluptuous body. Enjoying the view, Billy delayed as long as he could but finally said, I have to pick Brenda for her legs, they are gorgeous. Billy thought what are they going to do next, they have each won once.

As if she had read his mind, Arlene said, "The last contest will determine who wins. Whoever makes you cum in her mouth is the winner. The person who was before her is in second place, and the other person is the loser. We each get one minute to suck your cock and then you get a thirty second break before the next person tries. No hands allowed, and you can’t move or help in any way. Are you ready Billy?

Thinking that he had died and gone to heaven Billy struggled to calm himself before he said, Yes I am. Who gets to start? He looked at Arlene who took out three toothpicks and held them in her right hand. She offered it to the other two women and in less than ten seconds they had arranged themselves in the order they would suck him. Charlene was first, followed by Brenda then Arlene.

Charlene eagerly undid his pants and pulled him out. He was already hard and she said, Oh Billy, it is beautiful.

Arlene placed a timer on his desk and said, Ready? Charlene nodded and Arlene said, Go, as she pressed the start button.

Charlene sucked him in like a hi-powered vacuum cleaner and began to work her tongue over his cock as she moved her head back and forth. Billy could barely keep from touching her as she worked. The bell rang and she stopped with a disappointed look on her face. You didn’t cum in my mouth Billy.

I’m sorry Charlene, maybe next time." The rest period was quickly over and Brenda was ready to start. The timer was started as the blonde took him into her mouth. She let her teeth tease his cock and her tongue tickle the tip of his cock when she pulled back. As soon as she started this Billy sucked in his breath and held it. The bell rang and he was ready to scream.

With a pout on her face Brenda said, Darn, that always worked on my boy friend.

Thirty seconds later Arlene was ready to go. Billy was surprised when she made very little effort to make him cum. Soon her time was up and his rest period started.

Charlene said, Oh boy, it is my turn to suck you again Billy. She applied herself with great enthusiasm but it wasn’t enough to win his cum.

Thirty seconds later Brenda was up and he almost came as the bell ended her turn. Billy felt sorry for her as she stood up with a disappointed look on her face.

Arlene smiled as she got ready for her turn. When the timer had started she sucked him in and started to hum as she slowly pulled back to the head of his cock. Thirty seconds of this and Billy came in her mouth. She sucked him dry. The other girls could tell by his face that Billy had cum and were disappointed, but Charlene was the most disappointed.

I’m sorry Charlene but Arlene won fair and square. Billy tried to console her but she was on the verge of tears.

Arlene and Brenda were bouncing with joy. Okay Charlene, bend over, it is time to get your ass spanked. Brenda couldn’t keep the glee out of her voice.

Spanked? asked Billy.

The winner gets the tiara, said Arlene as she placed it on her head. The loser gets a spanking from the two of us. Bend over the chair Charlene, your ass is already bare, that thong will offer no protection.

Gosh Charlene, I’m sorry, said Billy, "You can suck my cock while they are spanking you.