A NOTE REGARDING THIS STORY.

This is a fictional chronicle of a normal hardworking guy named Jack. The federal government made him an offer he couldn't refuse. All they asked was for Jack to go undercover to help the U.S. Government ensnare a terrorist.

Any resemblance of the characters depicted in the story to actual individuals is coincidental. All events are the sole responsibility of the author. None of the scenes in this story depict minors engaged in any sexual encounter.

This story has been previously posted on other sites. It is being posted here with a strong rewrite; some new chapters have been added. I had my BFF Monica Rose edit the material so it should be more readable. Marina

Marina: [email protected]

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Chapter 18 - Jack's Last Day at Work

"It's enjoyable to be a woman. It's fun to flirt and wear makeup and have boobs." Eve Mendes

Jack spent the dark hours silently weeping in his soul over this latest turn of events. He had to rationalize the motivation behind his decision. Why didn't he just say no? Why had he agreed to do this? The most likely reason is because he could never deny Rose anything or did he do it because it was the right thing or was he easily persuaded into it for some deeper reason?

Rose stared into the darkness, the only illumination being from their clock radio. The last conscious thoughts before falling into a troubled sleep were, 'I have my wants and needs, if my husband isn't man enough to stand up to me that's his problem. The total subjugation of my husband to my will is an untold delight and with any luck a precursor of many pleasant times to come.'

The week leading up to surgery had been especially difficult for Jack. Whenever Rose was displeased in any way, Jack's eyebrows were plucked like a chicken. Each hair removed was a bit more of Jack's masculinity disappearing.

As he was dressing for his last day at work, Jack noticed his unmanly thin brows. With a catch in his voice he grumbled to Rose. "I can't go to work looking like this. I have been trying to obscure my feminization, this I can't hide."

An unsympathetic Rose said, "Oh, nonsense, here with just a touch of eyebrow pencil I can fill them in for you. In a few weeks, they will have grown out."

Using her dark brown pencil, she expertly shaped Jack's brows with just a hint more of a feminine arch and colored them in a shade darker than his normal hair color.

"Stop being such a crybaby about everything. If you hadn't screwed up so much, you wouldn't have any problems. Now get dressed. We're going to be late for work."

In his haste to get dressed, Jack failed to notice his usual white brassiere had been exchanged for a padded beige one, that had he looked closely he would have noticed it clearly showed through his white dress shirt.

On their ride into work, Rose was particularly cheery. She could smell the perfume she had lavishly sprayed on Jack's jacket that morning. It was a lot heavier than she normally used on his clothes. Over the weeks, poor Jack had become desensitized to the smell. He wore so much of it at home the smell had become normal. But from the gossip floating around the office Jack was the only one that hadn't picked up on the aroma.

"Jack, please don't worry so much. Stop with the 'Miss Negativity', everything is going to be fine. Go into Mike's office and turn in your vacation request and then tomorrow Jack will go into a hiatus and Daisy will come fully into the daylight."

Just before arriving at their parking spot, Rose took out her lipstick and profusely applied an extra thick layer of the darkest red she owned. In addition to coating her lips, Rose surreptitiously applied a small amount to her thumbs. Riding up in the elevator, as the doors were about to open on their floor, Rose grabbed Jack by the back of his head, she pulled his face towards hers and kissed him with all her strength, grinding her lips to his and simultaneously wiping the red coloration onto his cheeks. Breaking the kiss she whispered in his ear, "Have a good day dear. No matter what happens remember I love you."

A befuddled Jack left the elevator and turned around and confronted Rose, "Honey I have not turned in a formal request for leave two weeks early like HR demands. What if Mike refuses to give me the time off?"

"Jack you are the stereotypical blond airhead. We decided you need some time off, for medical reasons, so everything is arranged."

"We? Who is we?"

"Oh, Mike and I had a long conversation about you. I have already cleared it with him. We had a long chat about you needing some time off, for 'personal reasons.' There'll be no problem. I have even given Mike my recommendation on your replacement."

"You did what?"

Grabbing Jack's head Rose pulled his face in close, wiping the remaining red residue on his cheeks. Nose to nose Rose firmly said, "Jack, I suggested Miriam Cohen, be promoted. She is more than qualified. Now, I don't like your tone. I don't have the energy, patience, or time for this hissy fit right now. As a company officer, I did what is best for the corporation, grow up and get to work."

Jack apologized for his angry outburst and headed for his office. Jill, one of the secretaries, met him as he was about to enter his office. She snickered and said, "My, my, don't we look elegant today, trying a new look are we? I love the new color you are wearing, where did you get it? I would love to get some for my grandmother."

Jack glanced down at his suit and responded, "Jill, what the devil are you talking about?"

With an embarrassing laugh, she said, "Never mind, it's not important. Mike wants to see you immediately."

Rose exited the elevator and trailed in her husband's wake. Waiting for Jack to enter Mike's office, she walked up to the Jill and, right on cue, started to cry.

"Jill did you see my husband? He is openly wearing makeup now. I could handle wearing woman's underwear to work, the dresses on the weekends, but makeup out in the open is more than I can take. Hell, he would come to work looking like Tammy Faye Bakker if I would let him. You want to see his latest photos? Come to my office at lunch and we can have a drink. I will show you the Daisy album."

"Daisy?" inquired Jill.

"Yes, just between us girls, when Jack is in his girlie mode he is quite narcissistic. He insists on being called Daisy and has turned one whole wall of our bedroom into a pictorial Daisy shrine. He has had me take hundreds of pictures."

Jill responded, "I would love to see the photos, but Mrs. Sokolov, I don't think Mike would approve of us drinking during working hours."

"Oh, you are a foolish girl, who do you think gave me the bottle I keep in my desk? Come on by and bring some friends we'll have a party. If you would feel more comfortable we could keep it to wine coolers."

A sympathetic Jill hugged Rose and tried to comfort her. "Yeah, Mrs. Sokolov, your husband, has always been a bit effeminate but the recent changes have everyone guessing. All of us girls have noticed the nylons, perfume, the plucked eyebrows, his mannerisms becoming so feminine, and then he started wear bras and the lipstick, but we all like both you guys. You have been great bosses. So we have kept quite. I am so sorry."

"Lipstick, that witch gave me his word it was only tinted lip balm."

"Mrs. Sokolov, it may have been lip balm it is hard to say.

"Why do you stay with him or is it, her now?"

"Jill, you are still young, as you get older you will find if you love someone you often have to overlook some minor quirks.

"I understand that, but this seems to be more than 'minor'. Is he into guys?"

"Oh, heavens no Jill, Jack lives in a cock free zone." Rose moved her hand to her crotch and extended her pinky and wiggled it about and said, "If you know what I mean."

"Excuse me for prying but I thought you and Mike were an item? The betting around the office is that it's only a matter of time until you left Jack for Mike."

"Yes, Mike is good for a few laughs, and other things, if you know what I mean? But Jack is the man I love. Pardon the cliché but Jack is my soul mate, Mike could never be anything but my boy toy."

Jill retreated to her cubicle grinning from ear to ear and bursting at the seams to tell everyone her latest gossip. Rose walked off sniffling and headed to her office. Sitting at her desk she rapidly converted her sniffles into humming, "I love it when a plan comes together". Rose was delighted at the way things were progressing; convinced Steve would be happy as well.

Within minutes, the story of Daisy had circulated throughout the building. Every secretary in the building was begging Jill for an invitation to the lunchtime party.

Entering Mike's office, a perplexed Jack stood before his boss. Mike glanced up from his desk and scrutinized his nervous employee. The bright color on his lips triggered an immediate reaction from Mike. He viciously attacked Jack's manhood. "You god-damn fairy, if you insist on wearing makeup, at least get lipstick that doesn't clash with your suit."

A bewildered Jack wiped his hand across his lips. He discovered the gift Rose has left him. A humiliated Jack started to explain, but Mike stopped him.

"Jack, you limpdick moron, just hand me your papers and get out! Get your ass back to pixie land or wherever fairies like you go. Lord, I can't for the life of me understand what that sexpot of a wife of yours sees in a twerp like you. If it wasn't for your wife and how let's say…accommodating, she has been in servicing the company's needs, I would have let you go a long time ago. I was going to let you go on medical leave but after your little fashion show this morning, consider yourself on 'unpaid leave status.' Don't call us. We'll call you when and if we need your services again. Maybe we can actually get a few new sales without the fairy leading our sales department! Now get out before I lose my temper and kick your sissy ass."

Jack returned to his office fuming. How did he become the bad guy in all this? He uses his hankie and exchanged his lipstick for a thick coat of colored Chap Stick. Rose stuck her head into his office during the early morning to check on Jack, but didn't give him the opportunity to say anything. Jack stood and followed her in an attempt to explain what Mike said. But Rose was gone before he could get the words out. During the day, Jack called Rose's office incessantly but she refused to take his call.

During her brief glimpse at her husband, Rose gleefully noticed he had removed the red from his lips but not from his cheeks. She also observed that without his suit coat Jack's bra was clearly visible through his white shirt.

The rest of her day was extremely tedious and Rose was only able to handle the most routine of actions. Her mind whirled at the possibilities that lay before her and Jack. She marveled at how close she was to her daydream.

During their ride home at the day's end, Jack complained to Rose about his embarrassing predicament. A disinterested Rose dismissed his concerns with contempt.

"Listen twinkle toes you are unbelievable, here you sit wearing a bra, a corset, stockings, and panties, and this time tomorrow you are going to be a man with tits and you are worried about a little lipstick residue. Get over it!"

After her harsh rebuke, Rose tried on several occasions to restart a conversation. Jack merely sulked and answered in monosyllable grunts. The ride home was filled with tension; it was so palatable you could cut it with a knife. They became embroiled in a huge traffic jam. Rose, normally calm and rational just lost it. She laid on the car horn and screamed obscenities out her window. Then spying an open ally, Rose drove the car up the curb onto the sidewalk and speed down the side street.

As they pulled into their garage, Jack ended his silence, "Rose, I am scared to death. I am having serious doubts about surgery. What will my life be like after this operation is over? Will I be able to go back to being Jack? Will I even have a job?"

In a cold authoritative tone Rose shrieked, "God damn you Jack, if you attempt to wimp out now I will never forgive you! You are delusional if you think I will let you renege on your promise!"

"Relax Rose, I will keep my word. It's just that the magnitude of my decision could have all kinds of unintended consequences. Hell, how will I ever get my old job back? No one is going to respect me, I will be a pariah. I will be known as the salesman with boobs. I will be laughed out of the business."

Rose could read her husband's facial micro expressions and knew he was under tremendous psychological stress, so she hugged him and teasingly whispered into his ear, "Jack, cheer up, you always hated that job anyway. When this is over we will find you something more suitable to you talents. I hear Lucy in accounting is pregnant so in eight months or so there is going to be an opening in the secretarial pool. Of course you will have to work on your typing and dictation skills, but maybe I can pull a few strings. Speaking of 'dicktation', let's get you into bed. We can start your training right now."

After coating his lips in her most expensive and long lasting lipstick, Rose led Jack to the bedroom and was like a wild animal. She first pulled Jack to her chest and had him nursing there until she couldn't stand it any longer. She pushed her husband's head down between her legs. Rose luxuriated in the red telltale marks ringing her nipples. As Jack worked his magic in her love garden Rose clearly visualized a similar residue on her vulva. After several satisfying organisms, Rose permitted Jack, for the first time in weeks to enter her Bermuda triangle – an area where Jack's prick went into never to be seen again. The two lovers kept at it until exhaustion overtook them both.

Luxuriating in the afterglow of sex, Rose continued to tease her husband. "Cheer up Jack; you have just exchanged a position in the boardroom for one in the bedroom and that is one position you are in no danger of ever being laid off."

The reason a dog has so many friends is that he wags his tail instead of his tongue.