The Metamorphosis of Tiffany

Tom put the cap back on his beloved red lipstick and admired his latest masterpiece in his wife's vanity mirror. He blinked at his reflection which showed a semi-realistic looking woman, albeit a trashy one. His long false eyelashes setoff his smoky eye makeup perfectly. It was just the look he was going for. After years of surreptitious practice, he had cultivated a real talent for applying cosmetics. It had taken months but he now had the slutty Jessabelle look down pat.

His wife had decided to celebrate Thanksgiving at her sister's house and would be gone for the entire weekend. It worked well that his sister in-law didn't seem to like him, so Tom had elected to remain here at home and allow his wife some alone time with her sister. It would let him take advantage of her absence to live out his ultimate fantasy.

He stood and was a bit wobbly in his new red patent leather CFM's 6-inch stiletto high heels. They were, in is his opinion, the epitome of sex-appeal. He looked down and smoothed his micro mini red plaid tartan school girl skirt. He loved the fact it that it barely concealed his pretty Lycra panties that were chosen because they firmly held his tuck in place and gave him the illusion of a Venus mound. He had selected this length skirt because it showed the garter tabs from his waist cincher that held up his black seamed fishnet stockings. He reached for a hairbrush from the vanity and unsnarled his long wavy platinum blond wig, happy with the fact it came down to his shoulder blades. He attached his heavy extra-long drop earrings. The fact that they tugged on his ears and sensually brushed the top of his shoulders when he moved his head, created an almost orgasmic sensation.

The heels made walking on the bedroom's shag carpet an exhilarating adventure. He cautiously made his way to the queen-sized bed where he picked up his silicon double D breast forms with their perky nipples and slid them into his favorite sheer black brassiere. Once they were properly adjusted, he put on a white blouse and tucked it into his skirt. It was sheer enough to show his black bra and matching waist cincher.

He picked up his black purse and threw the strap over his shoulder. Then he cautiously made his way down the stairs to the basement family room with its hardwood floor. The click-clack of his heels only added to his fantasy. He reached the safety of the wet bar and poured himself four fingers of whiskey. He took a large swallow and couldn't but help notice how his lipstick marked the glass. He slowly sipped his drink and took an e-cigarette out of his purse. He didn't like smoking but thought a working woman would normally have one. He leaned against the bar and puffed between sips. The fantasy of the 'Pretty Woman' movie ran through his brain, he was Julia Roberts waiting in an upscale bar for her date, a handsome Richard Gere look alike.

@ @ @ @

When Tom started crossdressing, his goal was simply to be passable. Wearing his mother's bra, heels and her lipstick was enough. He still remembered his first wig, a yarn Halloween one from Walmart. It paled in comparison with his current human hair wig that had taken almost six months to save up for. He had discovered as the years moved on, it took more and more feminine enhancements to achieve the same euphoric feelings. It was now to the point where only the most outlandish and sexy outfits would feed his addiction. Standing there dressed as he was, in his mind's eye he only saw a sexy high priced escort. He had lived out the fantasy in his head a thousand times. Now he had the opportunity to play the part of a sexy call girl in the safety of his own home.

He had finished his highball, so he poured two more fingers of the amber liquid, and took a large swallow. He was halfway in the bag by this time, so he left the glass on the bar and stood back. He didn't want to lose control. He brought his faux cigarette with him and took an occasional puff. He skillfully conducted his streetwalker strut walking the length of the room. He pivoted on the balls of his feet and retraced his steps. His feminine voice needed a lot of work, so he limited it to a few well-rehearsed phrases. Each trip across the room he went into his falsetto voice repeating his pickup lines.

"Hey big boy would you like some company?"

"You look like you are ready to party, want a date?"

He reached the bar, threw down the last of his drink, did a well-practiced hair flip and demurely ask, "What? You want to know what I charge. If you have to ask you can't afford me!"

@ @ @ @

Helen had been suspicious for months that her husband was fooling around, a whiff of perfume every now and then, a slight trace of lipstick were unmistaken signs of a cheating husband. Nothing definitive but enough to make her suspicious. She had baited her trap, with a promise of visiting her sister for the weekend. She returned home after spending six long hours shopping to find his car where she expected in the driveway. If it hadn't been there, she had been prepared to cruise their small suburban neighborhood until she found it. It was parked in the drive way so she went with plan B.

She had left the sliding glass doors unlocked in the basement. She thought she would take her shoes off and sneak into the house, catching her husband with his hussy. She arrived at the glass door and was shocked. There was a busty tart smoking in her house. She was going to kill Tom when she got her hands on him. She had her hand on the door when the woman turned full on to face her. She thought she had been caught, but the whore's eyes didn't seem to focus. It was as if she was off someplace else.

It was then that Helen had an 'ah hah moment'. The tramp in her house was no one but her husband. He certainly had some explaining to do now. Cheating with another woman was one thing but what would she do when he was the other woman. The shock turned to disgust as she put her ear to the door to listen to what he was saying. It was muffled but she could make out enough that it appeared he was rehearsing for a night on the streets. When Tom had his back to her she quietly slipped into the room. She heard him dissing his price list for various sexual services. Her shock became pure abhorrence and she decided to teach her faggot husband a lesson. In as a deep a voice as she could muster she said, "Hey bitch want to fuck?"

Tom froze and slowly crumpled to the floor in a dead faint. His head bounced off the hardwood like a basketball. His skirt flopped up revealing his crotch. Helen gasped, there was no sign of his boy parts. She made a mental note to ask how he did that.

She knelt and checked on him. He was out cold. She could feel a large lump raising on the back of his head. Helen wasn't sure what to do. Her first impulse was to call 911. But looking down on her husband made up like a drag queen shelved that idea. The embarrassment of paramedics seeing him like this would be too much. She went with option two, she would nurse him herself. Her anger continued to grow as she ran upstairs for an ice bag.

@ @ @ @

She had not been happy in their marriage for some time. Tom was a real stuffed shirt. His idea of a good time was staying home and watching sports on TV. In addition, he was a bit authoritative; but a good provider. Overall not a bad husband, she realized she could have done a lot worst. Her discontent was partially her fault. She was the one who insisted that she wanted to be a stay at home wife. Her mother had taught her a wife's role was to help her husband with his career.

Thanks in large part to her efforts, Tom had risen to a mid-level management position in his conservative financial firm. She spent many long hours at the ironing board to guarantee he was always properly attired for work in clean starched shirts and pants with a sharp crease, but she drew the line at shining his shoes, after all she did have some pride. She had hosted numerous dinner parties always playing the dutiful wife, smiling at the inane comments by his partners and their wives.

She filled a towel with ice cubes as a devious idea formed in her brain. This situation was just too good not to take advantage of it. She hurried to the master bathroom and its medicine cabinet to retrieve smelling salts. She then went to her cedar hope chest, sitting at the foot of their bed. Buried on the bottom was a gag gift from her bachelorette party. It was a totally life-like double headed dildo. She took it and the ice pack down to her unconscious husband. She wrapped his fingers around the rubber phallic device and placed his hand on his chest so that the mushroom head rested on his painted lips. She thought about pushing the bulbous head into his mouth; but it was so large that she was afraid he might choke. She then used her cell phone to take a dozen pictures, the perfect blackmail material. She took the smelling salts and waved them under his nose. Then she stood back and took more pictures as he slowing regained consciousness.

As he became aware of his surroundings, Helen laughed when he recognized what he was holding. He dropped the dildo like it was molten lead. Helen helped Tom on to his feet. She then went and pored two water glasses of whiskey.

"Tom, what do you call yourself when you are playing dress up?" Tom blushed and meekly replied "Tammy."

Handing him a glass she said "Sit down Tammy, we need to have a talk. How many men has Tammy been with professionally?"

Tom stuttered at the accusation and answered. "None! How could you ask me that?"

Helen just smiled and said, "Well Miss Tammy, you look like you were about to spend the night trolling for customers. What other conclusion could I come too?"

"I am concerned about my health. I understand AIDs is a real problem among gay men. So it is a serious question."

Tom vehemently denied being gay. He insisted it was just play acting. He had never been out of the house en femme.

Helen wasn't sure whether to believe this; but decided to give him a chance to explain. The two sat dressed as they were. Helen was insistent that he remain in his feminine attire. It was a long night while Tom answered her every question.

Her obvious initial questions were 'Are you gay?', ' "Do you want to be a woman?', questions in that vein. He answered each with total honesty and Helen was shocked at what she learned. She had always thought of Tom as an uptight straight arrow. The fact he had a soft feminine side took her totally by surprise. He explained that he had been dressing in his mother's clothes since he was 10 years old. He told her how his compulsion to dress had gradually evolved into more feminine then into outrageous outfits. Helen was particularly interested in why he felt the need to imitate a whore. Tammy merely explained he didn't know why; but he needed to grasp the complete womanly experience.

As the first rays of the morning sun crept into the room, Helen wiped the sleep out of her eyes and told Tom she was going to bed for a nap. He followed her upstairs; but she barred him from entering their bedroom suite.

"But I need to wash up and change." he whined. Her response was to point to the couch and said, "You made your bed sleep in it!"

Noon found Tom with a hangover, red bloodshot eyes, still in Tammy mode and all cried out. He made his way to the kitchen and put on a pot of coffee. It was midafternoon before Tom saw his wife again. She came out carrying an overnight bag. "Tom, I don't know if we have a future or not." She stopped at the front door and said, "This time I am going to my sisters to think things over. Don't try and stop me or even contact me, it will only make it worse."

@ @ @ @

Helen drove to Betty's house; her husband was gone for two weeks on a business trip.

Helen wasn't sure what she was going to do as she arrived at her younger sister's front door. Betty instantly realized her sister was in crisis and pulled her out to the kitchen where she made hot tea for them both.

Betty was as shocked as Helen when her sister related her story and showed Betty the pictures of her perverted husband. Betty had never thought Tom was good enough for her sister, now she had proof. The two woman spent hours plotting on how they were going to punish Tom for his deceit. The most obvious thing they considered was exposing Tom. Helen pointed out that would only hurt her as Tom would obviously lose his job. Meaning there would be no way to pay the mortgage.

Betty wanted Helen to divorce him. Helen vetoed that idea. They had failed to acquire any financial resources. The only thing they had of value was their car and house; both heavily mortgaged. She could get the house, but with no income she would be put in a major bind.

It took all day to come up with a plan that would reward Hellen while punishing Tom.

Helen would return home and feign acceptance of his life style. She would slowly strip him of his manhood. Her ultimate goal was to have him become a true sissy wearing nothing but puffy dresses. She would break his spirit, within the confines of their home he would only be allowed to dress as an ultra-feminine woman. They discussed the idea of a chastity cage, but Helen thought it more appropriate to make him 'tuck' 24/7 and some internet exploration produced the perfect way. If he wasn't already, Tom would soon be denuded between his legs. By pushing his testes up into their man cave, the ball sack would be just loose skin. Helen saw a picture where a man can pull his snake back and pull the skin over it, creating the appearance of pussy lips. The question was how to keep it that way. Looking around the kitchen Helen saw the answer. A bottle of superglue would assure it stayed in place, with the added advantage Tom would forever be required to sit when he peed. He liked tall heels and tight fitting outfits, he would get his fill. Starting immediately, he would pass the Alpha baton to Helen. She would rule the roost, he would do the household chores and do them in stilettos and heavy makeup and always in full tuck. As far as she was concerned his boy parts will never see the light of day again.

They both agreed that was an adequate solution, the problem was breaking Tom's spirit to get him to agree. Helen was afraid if she merely threatened him with her pictures he would except the humiliation and just leave her. So they needed him to experience something major, even catastrophic to break him. The two woman decided to sleep on it and finish their plan in the morning.

Betty awoke to the aroma of brewing coffee. She hurriedly dressed and made her way to the kitchen. Where she surprising found her very upbeat sister devouring a plate of bacon and eggs with a steaming mug of coffee.

"Good morning sis, your breakfast is in the oven keeping warm. Sit down and eat we have a lot of shopping to do. Tom's credit cards are going to get a workout. I have come up with the perfect scheme. I'll explain on the way to the mall."

Both woman piled into Helens car, as they hit the freeway entrance Helen explained her plan.

"I'll go home and pretend to except Tom's lifestyle and even agree to help him fulfill his lifelong dream. He said he wants to undergo the ultimate womanly experience, of being objectified by a bunch of men. We will take him to the red light district. I'll tell him I will accompany him as he strolls the streets. My plan is we will dress alike, so he will be able to relax. Then once he is getting into it, we will drop the bomb on him. He will get his feminine experience in spades. When he gets home he'll be putty in my hands."

"That doesn't sound like it will destroy him."

"When I get home I will insist he call the office and take the next week off, for a family emergency. I will dress and train him nonstop in the fine art of femininity. Come next Saturday, he will be well prepared for his trip down Tinkerbell lane."

With a mischievous smirk on her face Helen went on, "I unearthed my two headed dildo. I might even insist that part of his preparation for being a whore involve experience in giving head. If we had more time I might even fix him up with a real date. But I want Tammy to be a virgin on his debut. Whether he returns a virgin will be completely up to him. Make a note to pick up K-Y Gel and lubricated condoms at the drug store. I want my Tammy ready for any contingency."

Betty lost it and laughed so hard her eyes were watering. "In that case, we must also get him a box of tampons."

"Alright you talked me into it. Tammy is going to have a full purse. She will need a comb, a compact, breath mints and lipstick. On second thought a tube of lubricant could come in handy. We will ensure has everything a working girl needs."

"That should do it."

"You haven't heard the ending for our night out. I plan on turning his excitement into degrading humiliation. I'll let you in on it later. Our first stop is a bit of a drive. I found it on the net. It specializes in selling to drag queens and cross dressers. Tom has DD breast forms, but a tranny whore needs something a lot larger to make heads turn. On their web page this store has a set they advertise as the Dolly specials, they are 1800g F cups and said to be very lifelike."

"My god Helen! Nothing that large can be lifelike. He'll have trouble standing in anything that large. How will you find a bra to fit?"

"That's easy, he won't be wearing one. I plan on gluing his bouncing Buddha's on. Imaging how they will wobble and jiggle. Guys will be lined up around the bock to titty-fuck my sexy Tammy."

"Tammy, is that his new name? That doesn't sound very hooker like."

"You are probably right. What do you think his professional name should be?"

"I haven't known any whores; but boom boom Tiffany would be good."

"Tom – Tiffany, I like that. I'll christen him as soon as I get home. We will need to find some jewelry with his new name on it."

"We must also find someplace that sells corsets. Tiffany currently has a 32-inch waist; I want something that will reduce that by six inches."

"OMG sis, you can't be serious! He wouldn't be able to breath."

"As long as he can swallow is all I care about."

Betty did a double take at that comment.

Helen didn't miss a beat as she continued. "He will have a spectacular figure. I bet a prostitute with 40 F, 26, 40 figure will have no problem getting johns. Once laced into a super tight corset, he will be forced to maintain the perfect feminine posture, back ramrod straight, ass out and boobs leading the way. Watching him struggle with those in 6-inch needle stilettos will be hilarious. I bet after a few blocks the reality of his fantasy will change his idea of what is sexy."

Helen though about how she could make the experience even more humiliating and came up the solution, "He doesn't know it yet but his cosmetics will all be switched out for the long lasting kind. Waterproof mascara so his potential tears or other bodily fluids won't ruin his lascivious appearance. Thick black eyeliner and kiss proof lipstick will be essential."

The two women spent the entire afternoon shopping. By the time they were done, Tom's credit card had been through a real workout. Helen was delighted the bill wouldn't arrive until after Tiffany's coming out party. He would have no way to know the types of shops she had visited.

She arrived home long after dark to find that there were no lights on in the house. She was momentarily concerned. She opened the front door and found her husband in boy mode sitting in the dark. The defeated look on his face spoke volumes. For just a moment, she had the urge to rush to him and give him a reassuring hug. After all she did still love him. She took a deep breath to compose herself and walked in the room and stood with her hands on her hips and her legs spread and glared at her husband. He was dressed in his normal weekend garb, baggy sweatpants and an old T-shirt.

Tom spoke first, "You're home. I wasn't sure you'd come back. Does this mean you're not leaving me?"

Helen forced a smile on her face and put her plan into action. "No dear, I seriously thought about leaving you. However, I have decided I love you and want to stay married. Under certain circumstances. If you won't agree to my rules, I'll pack my bags and the next thing you'll hear from me will be from my lawyer."

"I agree. I don't want to lose you."

"Not so fast. You don't even know what I want."

"I don't care; I'll do anything to keep you. I only want to make you happy."

Helen's smile became genuine as she said, "That's a coincidence that's what I want too. I also want you to be happy. No more sneaking around behind my back. If you want to dress, that's fine with me; but only under my conditions. From this point on. You will wear nothing but feminine clothes in the house. You may only wear your man outfits when you go to work. Is that acceptable?"

Tom's heart leapt in his chest. This was his dream coming true. "Of course honey, it would be my pleasure."

"Tom, there's more. You will become the de facto housewife while I will assume your vacated position as the head of the household. I expect you to perform 'ALL' of the womanly duties. I'll look upon you not as my husband rather as my wife. I'll be the one sitting watching TV and reading the paper while you cook and clean. As the Alpha dog, I'll make all the decisions regarding our lives. Tomorrow, I will transfer our joint bank accounts solely into my name. I will give you a small household allowance. You will not use your credit cards to charge anything without my prior approval."

"Yes dear, that's fine with me."

"Good we have the basics out of the way."

Helen went over and patted him on the top of his head as if he were a small child. "I know that this will be hard on your masculine pride so as a reward I have decided to cooperate in fulfilling your stated fantasy."

"I'm not sure what that means."

"It means you are to call your boss and tell him you are taking next week off because of a family emergency. I'm going to train Tiffany. By next weekend, you will be able to realistically pass as a street walker. Then Saturday night, Betty and I will drive you to the red light district where Tiffany will make her grand appearance as a hooker. One other thing, I will never again refer to you as Tom within the confines of my home. You will henceforth be known as Tiffany. So what say you?"

"I've no problem with the name change; but actually walking the streets by myself scares the hell out of me. It was only a fantasy, I never expected to do it for real."

"Well sometime dreams do come true. I plan on dressing you as a slutty prostitute with huge tits; but you won't be alone. I'll be with every step of the way similarly dressed. How does that sound?"

"Unbelievable. Why would you do that?"

"Because I love you and only want to make you happy. You must agree to do everything I say. No back talk or hesitation in your training regimen. If that is acceptable, go out to my car. There is a brown paper sack on the front seat. Bring it to me. Ignore the other things in my car."

Tom didn't even bother to put on his shoes and rushed to her car to retrieve the package. He was surprised to see the back seat of the compact car piled high with packages but didn't say anything about it.

Helen opened the bag and brought out a bottle of extra strength Nair. She handed it to her husband and instructed him to go to the bathroom and apply it all over his body. She would check on him in a few minutes.

While he was preoccupied, she brought the other packages in and hid them in the hall closet.

There were only two she needed for the time being. One had eight nanny cams. Helen set them up in every room except the bathroom she intended to document every minute of Tom's transformation. After hiding them she went to her lap top and ensured their Wi-Fi connection was working. She set everything to record and opened the other package; a leather riding crop. 'You never know when a little discipline will be needed', she thought.

Helen entered the bathroom to find her husband covered in the smelly lather. She walked around him with her hands behind her back ensuring he was completely covered.

She got to his front and found his pubic area had not been treated. Tom stood with his arms at his sides, Helen took her riding crop out from behind her and lightly tapped his man parts. "It seems you can't follow simple instructions. What part of your entire body didn't you understand?"

"Tom stuttered, buu…t the directions warned about avoiding sensitive areas."

Helen tapped the bottle and simply said, "I don't want to see any uncovered skin! It's my way or the highway!"

Tom groveled and said, "Yes dear. Sorry dear, it won't happen again."

She stood there tapping her riding crop in the palm of her hand and watched as he covered his entire pelvic region to include his ball sack and up his crack to his backdoor. She waited until he got happy feet and was squirming in discomfort. She finally allowed him to get into the shower to rinse off. She waited several minutes and then maliciously flushed the toilet and heard him scream. Satisfied she had established her position of dominance, she threw him a towel and said, "When you're dry, meet me in my bedroom."

He entered with the towel firmly secured around his waist. She had her hands behind her back obviously hiding something which made Tom nervous.

She commanded that he lose the towel and moved closer for a final inspection. Satisfied that he was completely denuded she demanded that he kneel at her feet.

He complied and looked at his wife with a mixture of fear and anticipation. Helen brought out her present, it was a necklace bejeweled with rhinestones that spelled out Tiffany. She attached the clip and let it fall into place, announcing, "As Lord of the manor I do hereby christen ye 'Tiffany'. Now give me a kiss to celebrate."

It was a tender and loving kiss, which sparked something inside of Helen. She started to have second thoughts about her scheme. After breaking the kiss, she managed to regain her determination and handed Tiffany a long silk nightgown. They climbed into bed and spent the night cuddling. She woke with his morning woody poking her in the ass. She was determined that he would be going celibate the rest of the week. She wanted his libido at its maximum for Saturday night. She woke him with, "Good morning Sissy sunshine get up." She ordered that he immediately tuck his thing away. She was amazed as she watched the procedure. From that point on, Helen starting grinding up Viagra pills and secretly putting them in his food.

The rest of the week was hell on earth for poor Tiffany. He was in six inch heels for 16 hours a day. He was through a strenuous training program.

Mornings were spent on feminine deportment and mannerisms. Helen made him spend hours practicing his hooker strut, with an exaggerated hip swing. Afternoons were devoted to housework. After dinner was exercise time. By Thursday, she had him doing aerobics in heels.

Once he was proficient in his feminine gestures, Helen had him listen to a CD on how a man could talk convincingly like a female. They worked long into the nights on his girlie voice. By limiting his vocabulary to a few select phrases he mastered a husky, sexy voice.

Much to Helen's surprise, he rapidly learned how to sit and cross his legs like a lady. He could do it now like it was a lifelong habit. It was Thursday evening during his aerobics when his tuck came undone. This was the excuse Helen had been waiting for. She had him recline on their bed while she snuggled up next to him and gently pushed his testicles up their path of descent so that they appeared to be undescended.

Pulling his penis back, she held it there while forming his wrinkly sack to cover his little man. The hairless sack was gathered just so and, made into a good facsimile of a woman's labia minora. She held everything in place while she used her open tube of superglue to run a bead of adhesive over the faux lips to ensure that they would remain firmly in place. The fact she also glued his sack to his penis was of no consequence to her.

Tom screamed like a banshee when he discovered what she had done. Helen merely shrugged and said she was just trying to help. Besides, it was too late to do anything about it now. Tom had no choice but to consider it a fait accompli. Helen left the room and rushed to her computer to see what he would do. He sat on the bed and spread his legs to get a good beaver shot of his crotch in the dresser mirror. He used the braille method to examine his new anatomy. The nanny cam captured every minute of his tactile pussy examination. Helen was bent over in laugher, as giddy as a school girl.

In his heart, Tom was delighted at the effect, but he could never admit it to his wife so he kept his glee inside.

Helen returned and had him model an assortment of panties. Everything from a Victoria's secret pink boy shorts to a sexy lace-trim thong. He grudgingly admitted that his current predicament opened up his selection of undergarments. When he was getting ready for bed he also found to pee that he not only had to sit; but had to push up on his toes to rotate his hips to aim the spray into the bowl.

Helen was delighted with his progress so she doubled up on his secret Viagra dosage.

Friday morning, Helen produced her double head dildo and insisted that Tiffany be experienced at giving head, like every good whore. Tom vehemently refused until Helen sat him down at her computer and showed him a quick sample of her recordings of his training exercises. She openly threatened to send a complete copy to all his family, friends and business associates.

In the end, it was a losing fight and Tom got on his knees in front of his wife with her sex toy.

She positioned herself to ensure the nanny cam captured every second of his humiliation. She talked him through the process, making him crawl to her and openly beg to suck her dong. She had him lovingly stroking her pole before licking it from the fake scrotum to mushroom head. She ordered him to repeatedly kiss the head and look up at her with a smile on his face. Eventually under her encouragement he took the head in his mouth. He managed to swallow the entire thing and he bobbed his head rhythmically. The first time his nose buried into her hair patch Helen lost it. She grabbed the back of his head a vigorously fucked his face until she came with an earth shattering orgasm. At which point she declared Tiffany fully trained.

@ @ @ @

Helen had them both up early Saturday morning. Tiffany was dressed in a conservative house dress and carried his blonde wig while Helen carried his corset. Helen drove them to her beautician and she made Tom walk through the mall house dress with his crewcut in full view. He was a beaten man by the time Helen introduced him to the entire salon that the sissy accompanying her was really her husband Tom. She calmly explained his appearance by saying he was the lead actor in an all-male stage production of 'Some like It Hot.' She told everyone in the crowded shop that Tom was playing Marilyn Monroe's part so she needed his makeup to be dramatic and stage heavy. The wig was handed off to the stylist for a good combing out. One girl opined that is was still rather early in the day and the makeup might wear off by curtain time.

This was opening Helen had orchestrated to allow her to request semi-permanent makeup. The shop owner mentioned a type of makeup that would last long for a single day. Helen explained he had a matinee and a second show on Sunday. She and the owner agreed upon a brand that would last for up to a week.

The entire crew of the salon pitched in. One went to work on his nails to apply long acrylics. She was a bit confused why Helen wanted his toenails done in the same dark red as his long acrylic fingernails and lips. Helen explained it away by saying that it would help him get into character.

With his makeup done, the mass of beauticians clustered around to admire their handiwork. Helen pushed her way to the middle of the circle and held up a beautiful vintage underbust maroon brocade corset which produced a gasp from the ladies. Helen requested volunteers to help lace her husband into the garment.

One of the women took a look at the size and commented that it was way too small for him. Helen challenged the assembly to not only get it on put to get it closed. It took four very strong ladies to get the corset on and laced down to a 26-inch waist. Tom could do nothing but go with the flow, as he rationalized that Helen was doing this all so he could live out his ultimate fantasy.

He was made to carry his coiffured wig rather than wear it back to the car. A man sporting a crew cut with the face of a movie star created a stir as they walked through the mall. He had the wig in one hand and was forced to grab his panties through his dress to keep them from sliding down over his hips. Helen took pity on him and they hid behind a large fern. He let the panties fall to the floor and Helen picked them up twirling the lace panties on her finger for the rest of their trek out of the mall.

Once home, Helen had him carefully place his hair piece on its Styrofoam mannequin head. She helped him remove his dress and he stood nervously at the foot of the bed wearing only his tightly-laced form creating corset. Its long garter tabs swung freely as he trembled in anticipation.

He was seated on the end of the bed where Helen removed his shoes and slowly and sensuously rolled on a pair of seamed fishnet stockings, then attached the garter tabs to ensure that his hosiery would stay in place. She followed up with a pair of sexy towering red paten stilettos with six-inch needle thin heels. The ankle straps were tightened firmly to provide her poor husband a little added support.

When she announced she was finished, Tom relaxed. That is when Helen brought him a glass of fruit juice. He greedily drank it down completely unaware that his wife had spiked it with bowel-cleaning liquids that are prescribed for a patient preparing for a colonoscopy. When its effects hit him 15 minutes later, Tom staggered to the toilet confused about his sudden urge to defecate. Helen allowed him some privacy before hit him with another surprise. Tom had finished wiping and was finishing up when she stopped him. "It smells terrible. I bet your ass is really stinky. But I have the perfect solution."

Tom glared at his wife and replied, "I didn't know they made asshole deodorant."

Helen flashed him a smile, "They don't. But what they do make is something every woman is familiar with… perfumed douche. Your ass will smell like a field of flowers. Trust me your customers will love it. Now bend over and point that cute tushy at me. This will only take a minute. Just remember that you wanted the total womanly experience. No woman would ever consider going on a date without properly preparing her lady bits. I am only trying to help you and there is so much you need to learn about being a woman. Now grab your knees and let's get this over with."

As he bent over he said, "Damn it Helen. I'll never let a man near my ass."

Helen chuckled and said, "We never can know what the future might bring."

Shoving the spout up his ass she said, "Now shut up and take this like a man."

Tom complied and after a brief wait went back to the toilet. Once his bowels were again clean he staggered back to the bedroom. He collapsed on the bed exhausted and closed his eyes for a quick catnap. It was a little early but Helen could not pass up on the opportunity to bring out his monstrous breast forms. She liberally coated them with superglue. Tom laid there with his eyes closed when he was startled with a cold slimy feeling on his chest. He opened his eyes and was greeted with a view of two mountains of quivering silicon topped with two prominent red nipples.

Tom was speechless as he examined his newest appendages. With the corset and the weight of his boobs he had to ask Helen for help to sit up. When he did he found his breast enhancements were firmly attached. He stood and found they weren't going anywhere. He turned to Helen and asked, "Why don't they fall off?"

"I added a little adhesive to hold them in place. Imagine what would happen if they fell off during your promenade."

"I take it that this is what you plan on me wearing tonight?"

Helen laughed and said, "Here I thought all blonds were dumb. I got those special for my working girl."

"But I already have a set of DD's. I have been wearing them all week. What's wrong with them?"

"You do have a short memory. I told you I was going to be your twin tonight. Those are what I will be wearing."

"These monsters must have cost a fortune. Just for one tonight they seem a bit extravagant."

"You are right they were rather pricy; but who said they were only for one night. Besides they are a tax deduction for a girl in your profession. Consider them advertising."

At that point, the front door bell rang. In a panic, Tom asked, "Who's that?"

Helen looked at her watch and said, "It must be our ride. Betty said she would be our chauffeur for the night. It's almost a 90-minute drive into the city. That's a big favour to ask anyone. I think you owe her a big thank you for giving up her evening to help you live your dream. Now go get the door while I get dressed."

Tom threw his hands to his exposed crotch, "But I don't have any clothes on."

"You're right I almost forgot. Here put these on."

She threw a pair of pink laced panties to Tom. He bent to put them on and almost tipped over. Helen took pity on him and kneeled and slid them into place. It was at that point Tom realised that they had an open crotch.

"Helen you can't be serious!"

"Of course I am. You want to experience what it is like to be a prostitute right? A girl in that profession would naturally not want to inconvenience her customers. After all, time is money. Those allow easy access with minimum effort. Now stop whining and go let Betty in."

Helen had to help Tom to his feet, between the corset and his new front porch, his centre of gravity had significantly change. Once he was on his feet, Helen gave him a gentle push to the door.

"Wait I have no blouse or skirt. I'm practically naked."

Helen had a belly laugh. "Tiffany it's only us girls here. I can assure you that you have nothing Betty hasn't seen before. Of course she probably has never seen it in such large quantities. Now stop dawdling and go let her in."

From the sound of her voice, Tom could tell there was no room for negotiation. His plan was to open the door and hide behind it as Betty entered. He walked to the living room and was shocked to see Betty had let herself in and was standing in the foyer. He did the only thing he could think of was to throw his hands out, take a step forward, and in a theatrical manner say, "ta-da what do you think?"

Betty took a step back and closely scrutinized her brother-in-law. She raised her hand and made a twirling gesture. Tom did his best dizzying imitation of a pirouette. He finished up facing Betty and, for some reason, dropped into a deep curtsey. Betty stood and applauded the performance.

Betty fanned herself with her hand. "Tom, Tammy or should I say Tiffany, I fully expected to see a caricature of a sissy 'girlie man' or a Milton Berle imitation of Tallulah Bankhead."

Betty reached out and poked one of his massive tits. "I'm overwhelmed at what I see standing before me. This is not hyperbole, looking at you, I don't see a man. All I see is a beautiful over-developed sexy female."

Betty reached out and put her hands on his petite waist. "How do you breathe in that thing?"

Tom was still seeing only what he wanted to and was blindly ignoring all the warning signs in order to live out his dream scenario. "To be honest, I breathe with a great deal of difficulty. I accept that as the price of beauty. It does make me look sexy don't you think?"

"Honey, if I was even in the least bit gay, I would jump your bones right here. I can assure you guys will be fighting to get into your panties. This is going to be a night to remember. Where is my sister?"

Tom blushed at the compliment and said, "Please have a seat. She's getting dressed and she should be down in a few minutes."

Betty patted the seat next to her and said, "Sit here and keep me company. I would love to get to know my newest sister."

Fifteen minutes later, Helen walked out looking like a million bucks. Her makeup was perfect and dramatic. She also wore fishnets, black stilettos and an exact replica of the short schoolgirl skirt Tom had worn. Her chest was impressive, with the breast forms stuffed into a bra over her real breasts. She was wearing a white blouse tucked into the skirt so it prominently displayed, not only her figure, but also her black bra. Tom couldn't help himself, he let out a wolf whistle. Helen blushed and said, "Thank you Tiffany. Just remember you are on the other side of the gender divide tonight. It's men that should excite you. Now come into the bedroom so we can get you dressed and get this show on the road."

In stunned silence, Betty fished her phone out of her purse and set it on record mode. She anxiously awaited Tiffany's grand entrance.

Once in their bedroom, Helen laid out his skirt, an exact duplicate of the one she was wearing. Once it was on and fastened, Helen handed Tiffany her blouse, a carbon copy of hers. Tom hesitated and said, "You're forgetting something, where is my bra?"

"No dear I haven't forgotten anything. Why in the world would a girl want to cover up her best assets?"

Tom was not amused and replied, "Aside from the aesthetics of exhibiting my chest puppies, the lack of support will have them bouncing all over!"

"Exactly, a working girl needs to stand out from her competition. What better way than to flaunt those magnificent melons."

Tom couldn't argue with her logic so he put on his blouse, his long acrylic nails made buttoning his blouse a struggle. The blouse was tight across his bust, and worried that one bounce too many and he could put someone's eye with a button. While he was lost in thought Helen took the wig off its stand and ran a bead of glue around the wig cap. Tom asked her why.

Her reply was straight forward, "You don't want your hair to come off in the throes of passion. It would destroy the illusion."

Helen finished his transformation by putting 4 gaudy rings on each hand, followed by 5 thin bracelets on one wrist and a thin woman's watch on the other. Then the pièce-de-résistance was his Tiffany necklace. She handed Tiffany his purse and the two strutted arm in arm to show Betty.

The two ladies paraded in front of Betty while she recorded the event for posterity.

At the car, Tiffany was told to sit in the front while Helen climbed in and sat right behind him. Betty took off and seamlessly merged into the highway traffic. Betty watched her speed to ensure they arrived at their destination after sunset.

The neighborhood began to get seedy fifteen minutes before they reached the location Helen had selected. Betty could tell Tom was getting nervous as he squirmed in his seat. She reached over and held his clammy hand. For the first time, Betty began to feel sorry for him. "Tiffany, can I give you some sisterly advice?"

"Sure, I'm scared to death I can use all the help I can get."

Betty looked into the rear view mirror and could see her sister had a grin that went from ear to ear.

"Tiff we only live once; but if we do it right, once is enough. Everyone has regrets in life just make sure your regrets are for the things you have done, not for the things we were too afraid to do."

Betty followed the GPS to the designated spot. She stopped the car and unlocked the doors, Helen got out first while Tiffany sat frozen in place. Helen opened his door and tried to pull him out with Betty pushing. Eventually, his body was out but his head was still in the car. Betty looked up at him and said, "Sis, you said that you wanted the total female experience. You will never feel more womanly than when you have some studs prick in your mouth or pumping away in your pussy. Carpe diem – get out there and seize the moment."

"I can't do that!"

"Sure you can, just be selective for your first time. Once you've had your cherry popped, throw caution to the wind and let yourself go. There is more than enough time tomorrow for regrets. I will meet you two at the end of the strip, now get out there and enjoy yourself."

With that she gave Tiffany a firm push. Helen quickly closed the door and Betty hit the power locks, leaving him with no alternative. Tiffany managed to get his balance and was overwhelmed by the smells that assaulted his senses. There was the stink of sweat and stale beer, cigarette smoke, all mingled with sweet clouds of flowery perfume from the other ladies circling for customers. Helen took him by the right hand and started up the block crowded with whores and their pimps. All encircled by a school of potential clients, making their selections from the merchandise on display.

Helen kept her husband on the street side as they began their promenade. With Tiffany's Jessica Rabbit physique, he was immediately in the limelight. Propositions and wolf whistles came flooding in from every direction.

Helen walked her husband up the street pulling him away from the flash mob that had formed in their wake. From the expression on Tom's face, she could tell he was having the time of his life. It was her job to ensure that he would look back on tonight with nothing but remorse. The first thing she did was open her purse and pull out a pack of cigarettes and a lighter. She put one in her mouth and offered a second one to Tiffany.

Tom stood stunned, "You don't smoke!"

"Take a look around, how many of your colleagues aren't smoking? Tonight we're both chain smokers. Now take it and puff away."

Helen was right once again, they were like stage props and helped them blend in. They alternated between cigarettes and breath mints. As they made their way up the street, the two were bombarded with catcalls and lewd comments from every passing car. Tom flinched at a number of the comments. One persistent suitor stepped in front of Tiffany and propositioned him with, "Hey baby, want to sit on my lap for a little slap and tickle. My van is right around the corner."

He politely said, "No, thank you." then pushed on. Tom thought the man was a bore but cherished the attention.

Helen turned to him, " Don't worry dear. We'll find you a more suitable companion before the night's over."

"Helen, why do you keep insinuating that I'm going to have sex with a man?"

"Don't be so sensitive. I'm just teasing. Besides, can you honestly tell me that, as a self-proclaimed lifelong transvestite, you haven't wondered what sex as a woman would be like?"

Tom was suddenly tongue tied, his mouth was dry as a desert. Helen stood there with a condescending smirk on her face.

Tom eventually managed to say, "There is a difference between curiosity and desire. I'm not gay!"

Helen shrugged off his comment. As they waited for the light to change at the next corner, they were accosted by three men. One pulled Tiffany aside and slurred drunkenly, "Hey sweetie, how much for a quickie? I've got 20 pounds of dynamite packed in my shorts. I promise you won't be disappointed."

Tom was repulsed and inspired at the same time. He realized that he could actually deliver a line that he had practiced many times. "What? You want to know what I charge. If you have to ask, you can't afford me! Besides I bet your package has a really short fuse. No one likes premature eruptions." His two friends howled in laughter at his putdown. He slunk away looking for a more amenable companion.

Helen turned to him, "What's the matter Tiffany? This isn't what you expected? Well suck it up. The night is just getting started."

They were nearing the end of the second block and Tom's feet were beginning to hurt. He stopped under a street lamp and leaned against it not realizing the picture he presented. Helen fought off her latest suitor and came up to Tom. "Tired?"

"No, not really. It's just that my feet hurt."

"Well dear, just stand there. We'll take a short break."

Helen took out with a pill bottle and shook out a small pill. "Open up Tiff. This is an upper, you'll be feeling no pain in a minute."

"Where did you get it?”

"From a guy back there. He wanted to barter them for a quick fuck. I took the bottle and gave him a peck on the check. When he complained I told him he had just been fucked. Then I walked off."

"But I don't do drugs!"

"Tonight you'll do as I say. Take a look around, notice how you're dressed. I control your way home. Do you want to challenge me?"

Tom did as he was ordered and admitted in a few minutes that his problems didn't seem so bad.

They were approaching the corner and the end to Tom's dream when a red Jaguar screeched to a stop next to them. A middle-aged man in a very expensive suit, hopped out and approached the two.

Tom braced himself for the expected come on. He thought back to what Betty had said, maybe it was the drugs; but he wondered if this might be the moment. Instead, the handsome stranger bypassed him and approached Helen, which did a lot for her ego as she had been treated as the ugly duckling all night. He introduced himself as Jeff, and asked Helen's name. He offered to take her away for a night of drinking and dancing. Helen was tempted until he added, "If the price is right."

Helen stepped into his private space and announced, "There seems to be a misunderstanding. If you had simply asked me on a date, I probably would have accepted. I'm not the working girl here."

Pointing to her husband, she went on to say, "I'm merely my husband's manager. I handle all of his bookings. Give him a spin, it's a ride you won't regret."

Jeff jumped back in disgust. "Never mind. You both disgust me. By the way, you're on the wrong street. This is south Broadway. The freaks are one block north on First Street. I'm not sure which of you is crazier. Him for dressing like that or you for collaborating in his perversion."

"Oh come on Jeff, give Tiffany a chance. If you aren't satisfied, I'll refund your money no questions asked."

With that, Jeff stalked back to his car and was away in a squeal of tires.

Tom turned to his wife and asked, "Would you have really gone with him?"

"Of course, he was a real stud. Don't try and tell me you wouldn't have. You were practically drooling."

Tom wondered if there might be some truth in what Helen said. At that moment, Betty pulled up at the curb and threw open the passenger door. Helen hopped in and had the door closed and locked behind her in an instant. Tom hurried over and tapped on the window. Helen lowered it enough to talk to her husband.

Bewildered at this turn of events, Tom could only ask, "What's going on?"

"I'm giving you the opportunity to experience your fantasy. If you check closely you will find that everything a pro needs for a night on the town is in your purse. Along with your house key. I checked and it's about $165 cab ride home. Of course you should also figure in a nice tip for the cabbie. I have a locksmith coming over at 7 AM. So…if you aren't home by then, your key won't work. It's almost midnight and the drive is 90 minutes, you do the math and set your prices accordingly. One more thing, if you look close enough in your purse you will find a morning after pill. I guess we'll put your 'I'm not gay' statement to the real test."

As Betty pulled away from the curb, Helen yelled back, "Tiffany, I'll leave the porch light on for you."

As they drove through the intersection, Betty slowed down and moved toward the curb. Helen asked her what she was doing.

Betty had to speak over the noise of police sirens, "Did you see the expression in his face it's like the life had been sucked out of him. Maybe we should go back. This is really a dangerous neighborhood. I think he has learned his lesson."

"Damn you Betty, just drive. Tiffany is a big girl; I'm sure he will be able to take care of himself. I need to get home and wash the stink off me."

They arrived home in a little over an hour. Helen took her shower and Betty opened an expensive bottle of wine. Betty was on her second glass when Helen joined her at the dining room table. Betty's first words were, "What now sis?"

"We wait on his arrival. I have Tom scheduled for a doctor's exam first thing tomorrow. I won't have him giving me any STDs. We will go from there to get him a prescription for female hormones."

"You want to turn him into a woman?"

"NO! I just want to watch his expression as I make him take his daily dose of estrogen. I plan on being the marionette around here. I'll pull all the strings and watch my husband dance. Tom is going to have to adapt to a new life style starting with a fashion update. I'll be nice at first and let him dress in androgynous styles. I will leave him one man's suit for work but other than that I'll gradually move him toward a complete sissy wardrobe. His closet will be full of nothing but frilly, lacy, and floral outfits."

Betty snarled at his sister's attitude. "I watched him out there tonight. Tiffany was definitely an outlier. My lord, he was more feminine than all those full time whores. Tom really isn't a bad person; he just has an unusual…let's call it a hobby. Don't you think your plans are a bit extreme?"

"No, I don't. You're my sister. You have to support me on this."

Helen's attitude bothered Betty more than a little. "Let me ask, are you doing this as a way to punish Tom, or is this more for your ego, trying to prove you can control him?"

Helen smugly smiled and said, "Is there a difference?"

Helen went to her bedroom and returned with a double armful of clothes. She threw all of Tom's male garments on the table. She found a couple pairs of scissors and they spent several hours converting everything he owned into rags.

With that chore accomplished, the two women moved to the couch with a second bottle of wine. They positioned themselves to get a view of the street. Neither woman wanted to miss Tiffany's homecoming. They even went to the bathroom in shifts to ensure Tiff would always have a proper reception.

By the time the sun was shining through the front window, they had finished their second bottle of wine and were starting to get nervous. Helen wore a path in the carpet checking up the street for her spouse and ensuring the porch light was still on. Betty kept trying to reassure her younger sister that everything would be fine. When the locksmith showed up, Helen sent him away.

Around lunch time, Betty volunteered to retrace their steps to try and find Tom. Helen stayed home to wait on Tom's return. She ignored the speed limit and arrived in the red light district in the early afternoon. Driving through that neighborhood in daylight scared the bejesus out of Betty, she double-checked to make sure all the doors were locked. She wouldn't walk there in broad daylight and she couldn't believe that not only had Helen and Tom walked through here at night, but they had abandoned him here.

Her imagination went wild. Her conscience tore at her over her part in this. What if Tom had been injured or arrested? She thought about going to the nearest hospital; but gave that up when she realized she had no idea what or who she would ask for. She settled on stopping by a convenience store and buying all the local papers.

She sat in her locked car and scanned them, finding several articles about overnight muggings. The truly disturbing item was a brief headline about the death of what was described as a working girl who had been so badly beaten that the body was unrecognizable. An empty purse had been found near the body with no identification, only a nondescript key.

The local area was being canvassed to see if the key would lead to an identification of the body. Betty noticed that the article failed to identify the gender of the victim. She threw the paper on the seat when a small article at the bottom of the page caught her eye. It announced that the new law-and-order Mayor had announced a crackdown on prostitution. Over twenty hookers and their johns had been rounded up in the past few nights. They were going to be prosecuted to the fullest extent of the law. He promised his office would fight their release on bail.

Helen was a nervous wreck when Betty walked in the front door. Betty related what she had read. Helen's smugness was a thing of the past, but her only comment was, "If Tom is dead how would I survive."

Betty got right up in her grill. "Damn it sister! He could be dead or in some hospital ward. Hell, he might be stuck in some jail cell. Doesn't that concern you? "

Helen shrugged. "Of course it does. Until he contacts me there is nothing I can do. If he was in a hospital they would call, after all I am the next of kin. If he was in jail, he is allowed one phone call why wouldn't he ask for help? "

Betty could not fathom her sister's attitude. "Sis, maybe he doesn't want to talk to you."

While Betty was freshening up, Helen thought about various scenarios. If Tom were dead, how would she go about claiming his life insurance? Maybe she should go to the police. Then she pictured the embarrassment of identifying her husband as the dead tranny hooker and decided the $10,000 life insurance wasn't worth the money.

Neither woman slept, they spent the night on a vigil. Betty hadn't prayed in years. She actually got down on her knees, asking for Tom's safe return and for forgiveness for her actions. Helen had her own regrets, realizing she was at least partially responsible for the current situation.

Betty stayed for a week. During that time, she had driven Helen to Tom's work place where Helen asked that Tom be put on leave by explaining the family emergency had gotten worse. Helen breathed a sigh of relief knowing a paycheck would continue for two more weeks.

The morning of her departure, Betty found an article on the last page of the local paper, saying the police had identified the body of the dead hooker. It was a load off her mind and made the drive home easier.

When Helen got Tom's last paycheck, she went to his boss and told him that Tom would have to be put on indefinite leave. She was informed that this would be unacceptable. If Tom wasn't there on Monday, his services would no longer be needed and he would be terminated. When they terminated Tom, Helen received his severance pay. When that ran out she emptied his 401 K account.

By the end of three months, she was forced to look for work. Her lack of experience in the workforce meant her only options were fast food or waitressing at a local IHOP.

@ @ @ @

It was one of her few days off from the pancake house. Steam curled out of the cup of hot tea she cradled in her hands as she tried to absorb more of its warmth. Her sweat suit only went so far to ward off the fall chill.

Even after all these months, she still looked frequently out her front window. She perked up at the sight of a black stretch limo with tinted windows pulling into the driveway. The uniformed driver hurried around to open the passenger door. Intrigued, Helen stood framed in the window, gawking.

A tall brunette woman stepped out of the car, wearing what appeared to be an expensive mid-length designer dress. Her face was hidden, pulled down in a fur wrap. Helen's heartbeat raced as the mystery woman made her way up the walk to her front door. Helen kicked off her fuzzy slippers and rushed to the door. She threw open the door as the doorbell sounded. The identity of the woman was still hidden as the woman’s long hair fell across her face.

Helen simply said, "Won't you come in?"

"Why yes thank you. It's colder than a witch's tit out here."

Helen led her caller to Tom's favorite chair, a well-worn recliner. The mystery lady sat and crossed her legs making herself comfortable.

"Where are my manners? Would you like something to drink? I have a pot of tea on the stove or I could find something stronger if you want. "

"Tea will be fine." Her guest observed, "It's a bit chilly in here."

Helen smiled apologetically. "I know I keep the thermostat low to save on money. I'll be right back with your drink."

While she was gone, the woman stood and toured the room. She paid particular attention to the display of family photos. Helen returned to see that she was holding a picture of Tom displaying a prize trout and smiling. Helen walked over to her and took the picture and handed her the tea saying, "That's my husband."

"I know him intimately," was the woman's reply.

"Really how so?" asked Helen

The woman turned to face Helen and glibly replied, "We share the same soul. Don't you recognize me Helen?"

Helen's knees began to buckle and she sat down on the coffee table before she fell down. "On my God, Tom. Have you come home to me?"

Tom slipped off his sable stole. Helen had never seen anything like it. The fur had been silverized to look as though it was continually bathed in moonlight.

Helen gasped at the luxuriousness of the wrap.

Tom picked it up and ran it across his check and said, "You like this? It's my favorite too. The full length minks are just too bulky and ostentatious to wear around. Don't you agree?

"Helen we need to talk and not about my wardrobe. A lot has happened in the last four months. How are you doing?"

"Me? I'm fine but I've been worried sick about you."

Tom waved his hand in a dismissive gesture. "I am better than alright. I wanted to stop by to thank you."

A bewildered Helen stared at him and, for the first time, she noticed his dress. It was low cut and displayed an extraordinary amount of cleavage. Pulling her attention back to their conversation she asked, "Thank me for what?"

"You changed my life."

Helen thought to herself, 'That was exactly my intention, I just never thought he would thank me for it.' She did manage to say, "Change how so?"

"When you deserted me that night and left me standing in the street. I felt betrayed, vulnerable and violated."

Helen interrupted, "I'm so sorry for what I did. Can you ever forgive me? My anger and embarrassment over you being a closet queen clouded my judgement."

Tom smirked at his wife's less than politically comment and addressed her directly. "Helen, I must insist you remain quiet and let me finish. As you drove off, I was lost and I thought my only choice was to do as you said. I started walking to the next street. After a couple of rejections, I managed to work up the courage to let a clean looking guy proposition me, I was getting desperate so when he said he wanted analingus I agreed without even not knowing what it was. I quickly found out it was oral sex followed by anal coupling. It was nothing like the stories I had read. There was no pleasure at all. The only good thing was I insisted we use protection and he did pay me rather well. I felt dirty but time was running out. So I went looking for another customer."

Tom paused to take a sip of his tea. Helen smiled on the inside imagining her husband getting butt fucked.

Tom put his cup down and went on, "After my second encounter with gay sex, I was disgusted with myself. I realized that I was degrading myself only so I could come home to you. It became crystal clear all that you did to me was vindictive and not out of love. I realized that life without love is not worth living and I decided to end it all.

"I stood on the curb and waited for a large car. At the last minute, I stepped out in front of a Lincoln town car. I stood there holding my breath and my closed, waiting for the impact. Imagine my surprise when I opened my eyes only to find the car's front bumper eight inches away from my knees. The shock made me faint dead away. When I opened my eyes, I found myself in the arms of the best looking man on earth. Fred had rushed out caught me in his arms and laid me in his back seat."

Helen was shocked at what she just heard. "Tom, it couldn't have been that bad. I only tried to provide you the ultimate fantasy experience."

Tom ignored the obvious lie and went back to describing his saga.

Fred started to dial 911 but I stopped him, telling him I was physically fine. He offered to drive me anywhere I wanted to go. When I wouldn't tell him where I lived and refused to seek medical help, he drove me to his penthouse."

Helen thought, 'I bet he did.' But trying to be polite she asked, "So what happened next?"

"He made a pot of coffee and tried to console me."

Helen couldn't hide her sneer, "And just how did he console you?"

Tom just stared into his teacup. "We just sat and he let me talk. He's a great listener. I told him everything. My life long experimentation with cross dressing, even about my feelings the day you caught me and, of course, how you treated me. I talked about my experiences on the streets.

"He wasn't judgmental, simply supportive. After I was all talked out, he let me take a shower and then led me to his bed. The dear man even brought me breakfast. When I was finished he sat with me until I fell asleep."

Helen couldn't help herself, "So you slept with him?"

"No he slept on the couch. He was the perfect gentleman."

Helen had her doubts but didn't say anything.

"The next morning, Fred had his doctor make a house call. He checked me over and declared me disease free. The doctor helped me to remove the wig and breast forms, I was too embarrassed to have him remove the glue from my groin. I had to wait that one out. I can't tell you how happy I was when my package worked itself free."

Helen maliciously thought, 'I bet this guy Fred was too.'

"Did he make you stay?"

"Quite the contrary. He offered to drive me home, but he offered some advice as well. He made it clear I didn't have to go back to you and your disdain.

"I seriously considered returning home. However, after reviewing your actions in the light of day, I realized that you never really loved me. I had the time to see your actions for what they really were. You only intended to humiliate and ultimately emasculate me. Yes, you were hurt by finding my secret, but the loving response would have been to figure out why I have this compulsion. Not to just demean me.

"Fred helped me realize I am not just a cross dresser. He accepted me for the person I am, flaws and phobias and all. He got me to a good psychologist who diagnosed me as being transgender."

Tom took a break to let his last comment sink in. After tucking a lock of hair behind his ear, he took a sip of his tea.

"The doctor and Fred showed me I still had choices in life and I can be loved for the person I am. Anyway, Fred invited me to stay with him until I could figure out what I wanted to do."

That comment knocked the smugness out of her. Trying to regain some control she asked, "He let you stay, he must have wanted something from you."

"Only my companionship, he even wouldn't let me help with the cooking or housework. He has a maid service and a personal chef that come in daily."

Helen made a face, not trying to hide her suspicions. She thought, 'Being picked up by a handsome rich man who asked nothing in return was purely fairytale material. It just doesn't happen in the real world.'

"Over the ensuing weeks we became close friends." Again Helen wondered how close.

I told Fred I want to live out my life as a woman. He contracted for a fitness expert to help me develop a womanly shape. He also hired a personal shopper who spent weeks selecting an appropriate wardrobe for the new me."

Tom saw his wife raise an eyebrow at that and said, "Suzy has molded my fashion sense and after a few drinks has even offered me advice on how to handle men."

"Advice, what kind of advice?"

"About Fred mostly. I have to hold him back, he is very generous and can be extravagant if I let him. All I have to do is say I like something and the next morning, there it is."

Tom put his hands under his breast and held them up. "Like these for example."

Helen smiled and said, "Yes, they are the most realistic breast forms I've ever seen."

Tom made a sound that was between a laugh and a schoolgirl giggle. "You misunderstand. These aren't forms they are the best implants money can buy. They actually were the only thing we have argued over."

"He forced you to get them?"

"Oh, quite the opposite. I have wanted my own breasts from the first time I put on my mother's bra."

Tom got a faraway look in his eye. "I admit that Fred considers himself to be a breast aficionado. When I told him my dream, he took me to the best plastic surgeon in the state. Our argument was about their size. He wanted them 'supersized.'

"Thanks to you, I learned that bigger is not always better. I told him 'large' was good enough. So we compromised and I got D cups."

Tom released them and they settled back on to his chest. "I'm quite proud of them. As you can see I prefer outfits that accentuate my décolletage. Fred accuses me of being a bit of an exhibitionist. Just because I wear only the flimsiest most translucent nightgowns to bed. Just between you and I, my psychologist has me on hormones, I haven't even told Fred that yet. The result is I think I'm growing, I know for a fact they are more sensitive and responsive. Suzy tells me I will need DD bras by the New Year. I'm not sure I believe her; she can be quite a tease."

Helen got up and excused herself saying she need something stronger than tea. She returned with a half empty bottle of Irish whiskey and poured a shot into her cup. She asked, "Tom, would you like some?"

He nodded an acceptance then said, "Just so you know, I'm no longer Tom. I had my name legally changed to Tiffany. I understand that was Betty's idea, I will have to thank her. The name fits me perfectly."

Helen asked, "Are you and friend still living together?"

Tom almost beamed. "Yes we are even sleeping together. I had to get him off that couch. It was destroying his back."

Helen looked devastated, "So you're having sex?"

"That's not what I said. We sleep in the same bed and just cuddle at night. Fred is rather old-fashioned. He insists we not have sex until after the ceremony."

Helen choked on her drink, "What kind of ceremony?"

"Why wedding of course! That is the main reason for my visit. Fred wants to do it right, so he had his lawyers draw up our divorce papers. I have them here in my purse. All you have to do is sign them."

Helen became pale. "I don't want a divorce and I won't sign them!"

Tom slowly stood and dramatically wrapped his stole around his shoulders and said, "Helen, one thing being married to you did was to test my mettle. I have found I do have a backbone. It's perfectly okay if you don't want a divorce. Fred is taking me to Denmark for my SRS. Once that is done, our marriage will be legally dissolved. With that impediment removed, we'll be able to have a real church wedding. Fred has booked us for a six-month honeymoon which we will spend touring Europe. The divorce will at least give you a small cash settlement. If you don't need it that's fine too."

"Wait a minute how small?"

Tom laughed and said, "It's good to see you haven't changed. My fiancée is an extremely generous man. He has agreed to a settlement in the low 6 figures."

Helen flew across the room. "Where do I sign?"

Tom tucked the papers back into his purse and skipped his way back to the limo. It didn't matter how big the check Fred wrote was, Helen would burn through the money in a year. He spent the ride home scheming on a way to get Fred to forget about waiting until after the wedding.

FIN