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 17 - Boobs

"Scientists now believe that the primary function of breasts is to make men stupid."
Dave Barry

Monday started off with the ritual aerobic exercises, followed by a breakfast that wouldn't keep a bird alive. Jack was dressing for work and found Rose had replaced all his undershirts with white lace camisoles. Jack started to complain, but by now had learned the futility of such arguments. It was easier to just go with the flow.

Wearing his padded bra and camisole, the two entered the elevator at work. Rose smiled to herself as the lacy top to his new underwear was apparent through his white shirt, as were the two ever-so-small bulges in the front of his shirt. On the ride up, Rose rested her hand on Jack's shoulder and she absentmindedly played with his bra strap, much to the amusement of the two secretaries sharing the elevator.

As the door opened on their floor, Rose leaned in and kissed his ear and softly uttered, "Sweetie, you are looking particularly alluring this morning. But you really should think about getting those cute little ears of yours pierced. We could stop on the way home. Drop by my office later and let me know what you decide."

The comment from Rose earned her a bright red blush from her husband and muffled giggles from the two secretaries.

@ @ @ @

Steve had just had another formal counseling session with the director. He was encouraged to move the operation forward as rapidly as possible, intercepts indicated Ivan had a meeting set up with several Arab businessmen. HLS wanted to know what was going on.

Rose had a meeting with Steve, this time it was in a swank cocktail lounge out near the local airport. The place was crowded with travelers. The couple took a secluded table in a dark corner where they would have some privacy. Steve was in a dark coat and tie. Rose wore a tight fitting red dress that accentuated her buxom figure, which advertised her womanly charms.

Steve sat across from Rose and had to force his attention to the photographs he had brought along. Steve spread out seven 8 by 10 glossy pictures of Jack. Most of were of Jack coming and going from their home and work.

Rose was mildly upset, as some were of Jack inside the house. She had assumed those would remain private. They both studied the photos and agreed that Jack was not presenting a feminine enough image for their desired outcomes.

Steve pushed Rose to agree she needed to turn Jack over to him, while she vehemently disagreed. She had her image of success. She wanted Jack to present as an attractive woman, while the government was more interested in a sissified man.

"Damn it Rose, you are acting like a 'Pageant Mom' getting your daughter ready for her first pageant. We don't need a beauty queen. Jack merely has to appear to be a feminine cross dresser. I thought we agreed you were offering up your husband for patriotic reasons. Whatever you are trying to do must come second to our mission, don't lose sight of that. Your country needs him."

She rejected his comment with a dismissive wave of her hand. As such, they agreed to disagree upon Jack's ultimate end state, what would constitute mission accomplishment in his preparation. Rose was adamant she would continue with her womanization of Jack, she didn't want a sissy for a wife when this was all over. Rose was an up and coming woman in the local business community. As a lesbian, she could maintain that position as long as her partner was a classy lady, not some cartoonish caricature of a drag queen. She was determined Jack would become that perfect helpmate.

Steve launched into his prepared argument for Rose.

"Mrs. Sokolov, let me be very blunt with you. Our target is the lowest form of humanity. As you know, he has a thing for she-males. We have already determined your husband is the perfect guy for this operation. We would be devastated if he backed out of the program. Looking at your husband as he is right now, there is no way he is going to survive this plan. While our target likes she-males, he likes them curvy, almost a woman, just this side of the real thing. If we're going to go forward with your husband there will have to be changes."

Steve paused as he took a sip of his highball. Sue put down her Scotch and glared at the government agent. "Just what kind of changes are we talking about?"

"I am suggesting a few minor surgical procedures."

Rose stopped Steve, "Look here mister government man, Jack is my husband. I love him very much; I know he comes across as a spineless Little Miss Pissy Pants. But we're not cutting anything off!"

Steve chuckled, "Cool down Mrs. Sokolov, we don't agree with your assessment of your husband. You're being a bite disingenuous about your husband's abilities. Don't confuse his flexibility and adaptability with lack of backbone."

An obviously agitated Rose was breathing heavily as her anger was built up. Steve had to force his eyes up from Rose's chest; their rhythmic swell created a state of confusion in Steve's brain. He wasn't sure if he envied or lusted after the two globs of flesh that were overflowing form the taut fitting top.

Rose couldn't but notice where Steve's attention was focused; her choice to go without a bra for the nights entertainment was obviously the right decision. Her outfit gave her an advantage in this negotiation. She took another sip of her drink and arched her back so her boobs practically rested on the table.

He had to shake his head and swallow twice to force himself to refocus; he then went on with his discussion, "Aside from the superficial physical and behavioral traits that initially attracted us to your husband, our behavioral scientists have determined that with his engineering background Jack is adaptive and innovative. He has the intellect to understand complex situations, to think creatively, and to solve problems. The only unknown if he has the leadership ability to interact with co-workers and motivate them to a common goal. As we see him, his major flaw is that he shows too much empathy towards others."

Rose sat and thought about what the agent had said. Steve reached out and took one of Sue's hands in his, "I agree completely with you on the issue of cutting things off. I don't want to subtract, in fact, I think we need to add. Ivan likes his girls passable and attractive, but fully functional as males. I was thinking small breast implants, just enough to look like flabby pectoral muscles when dressed as a man. With an underwire bra and padding, we could create very realistic cleavage."

Rose pulled her hand back and immediately rejected Steve's plan, "That's totally unacceptable to me!"

Preparing himself for a fight, Steve was flabbergasted by Rose's counterproposal. "If we are going to the expense and trouble of surgery, I insist we do it right. I love my husband and want him to come home to me. It is obvious that the only way that is going to happen is if he is 100% presentable as a woman. I insisted that we give Jack a respectable pair of breasts."

A flabbergasted Steve stared at Rose's chest and inquired, "Just what would you consider respectable." Rose followed Steve's eyes to her full chest. "Nothing like mine, I was thinking somewhat less showy yet still tantalizing. With Jack's build I would think we need something at least a full B cup. I know I can convince my husband to consent to those options."

Steve swiftly agreed with her analysis. He pledged the government would pay for it all, the doctor, hospital, nurses everything. Steve would set the whole thing up. All Rose had to do was get Jack to sign the medical release. Rose assured him that would not be a problem. Both concluded that the breast enhancements would significantly add to the cover story.

Steve lit up a victory cigar and gloated, once Jack was exposed as a man with tits, it would be the easy to convince the world, that he was actually a transgender male and was being pushed out of the closet by a vengeful wife.

Copious amounts of liquor were consumed before the two conspirators finished their plan. In addition to the excellent Scotch, Rose was talked into trying a flavored cigarillo. High on the alcohol, Rose was lucky to navigate home without being arrested for DUI.

Entering the living room, Rose reeked heavily of cigar smoke and alcohol. Arrogantly sitting in her favorite recliner, Rose sipped on a glass of Vodka and smoked one of her new cigarillos. Rose put Jack through his nightly ritual, controlling him like a puppeteer. While she blow smoke rings, she had him perform his exercises again and again.

A drunk and haughty Rose was more disparaging than normal. Finally, an exasperated Rose grabbed Jack by the wrist and said, "Come with me." Jack dug his heels in and refused to move. Rose angrily demanded he follow her into the bedroom. After a brief tug-of-war that Jack lost he found himself positioned before the bedroom full length mirror.

"I want you to be completely honest with me, what do you see?"

Jack responded, "I see me, a man, in a dress."

Rose responded with a snarl, "Exactly! That is the problem. Your target does not associate with drag queens. He wants a romantic companion with masculine plumbing but the looks and mannerisms of a beauty contestant."

"Isn't it enough that I’m taking on a drag queen charade, and putting my life in danger? Now you are telling me I have to become some terrorist's bitch."

Rose grabbed Jack and shook him hard, "Knock off the melodramatics."

Finally, she said, "I can appreciate how hard this is for you."

"Really Rose, who is asking you to become a man?"

"Alright, I'll give you that one; I can't possibly know how you feel. But remember why you are doing this, the lives you will be saving."

"Don't you dare try to lay a guilt trip on me!"

"You sass me again and I'll lay more than a guilt trip on you young lady."

Jack instinctively covered his ass with his hands and started crying, "But Rose I have tried as hard as I could, please don't hurt me again."

"Relax we are not going there tonight, unless I really have too. I only want to talk. Steve and I have had a discussion on your lack of progress."

She softened her voice so that her next comments would not be rejected out of hand.

"Sweetheart, you have made tremendous strides in your womanly presentation and I love you for the effort you have put into it. But you still look too much like a dude in a dress. The time for refinements are well pass, if this is going to work we need to make a change, something drastic, something to up the ante. The onus of that change falls on you my dear husband."

With an aching heart Jack prompted, "Go on Rose."

A beaming Rose continued, "Steve and I have decided there is only one possible solution to correct your deficiencies. We have made a decision concerning your future."

Jack balked at the thought that someone else was making decisions for him.

"Now what one minute Rose, I love you and will do almost anything you ask, but rather than tell me what to do, shouldn't you ask and let me get a vote?"

"Of course you get a vote dear, but as the primary breadwinner and CEO of this partnership I get the final say."

"Oh", said Jack, as he packed curiosity and a request for more information into a seemingly noncommittal syllable.

Rose went into her prepared sales pitch.

"When you picture a woman, what are the most obvious visual clues she is a woman? The female breasts and buttocks! Both are extremely potent sexual symbols of feminine beauty. Firm but well-rounded and shapely breasts and buttocks are powerful signs of a woman's health, and youthfulness. We have done what we can with breast forms. Unfortunately, their use has some very serious limitations.

"I have a proposition for you. I am not asking you to blithely accept the fact that you need, certain 'enhancements', to succeed. Without them, everyone concerned is convinced there will be cataclysmic consequences. I will not force you. There will be no ultimatums. If I can't persuade you, we will forget the whole thing. Jack this is not a fairy tale, there are no magic wands. Any success you achieve will truthfully be fraught with danger and be hard earned. If things go badly, you could not only die, and, in all probability, it would be a hideous and painful death. But I am optimistic; if you consent to our idea there can be a triumphant finale. We will have our 'happily ever after' ending."

With as much zeal and enthusiasm as she could muster Rose proposed, "What we are suggesting may sound a bit extreme, but hear me out before you reject the idea. We both agree that breast implants are needed. It is a minor medical procedure and can be done as an outpatient. With your own breasts the clothing options become almost unlimited. You will be able to wear all sorts of womanly outfits and show off an actual set of Ta-tas, the twins, the girls -- whatever you want to call them. Nothing screams, 'I am woman, hear me roar' like cleavage."

Rose was startled with the bluntness of his response. Jack could taste the bile in his throat, "Me with tits. Rose that is the most cockamamie idea you've ever had. Damn it, I won't do it. I'm still a man! Please, I don't want to be a genuine woman with a real bosom. Women are…are…"

"Are what Inferior?" Rose suggested.

“No. No. That's not what I meant; stop trying to put words in my mouth."

"See? You're lying to me right now, trying to smooth over your mistake."

Jake always hated arguing with Rose. "Okay, you're right. I think men are better at most things than girls. To be all honest, I think being a woman would be a step down."

Rose paused, trying to control her anger. She continued, "You're right. Temporarily having a set of breasts would be demeaning to a real man like you."

"Why are you trying to make me the bad guy here?" Jack protested.

Then she quietly said, "Okay, maybe I am thinking more like a flag-waving patriot than your wife on this matter. I guess we have no choice but to tell Steve that since you feel having an authentic woman's figure is beneath you and violates your sense of ethics, he can forget about his plan.

"It's your body Jack, what you have now is nothing more than two bee stings, I was thinking something very limited, a small B cup. With a good pushup bra and some silicone padding we could create the illusion of a set of first class tits. We could skip the silicone pads if you want to go with something larger, after all you have always been a breast man.

"Of course you are a man and will always be one as evidenced by your frequent bathroom 'moisturizing visits.' Honey, I am not trying to embarrass you, I simply want to point out that you can enjoy being a man while temporarily undercover in the veneer of a woman. I am not indifferent to your concerns. But you must stop your myopic testosterone-based thinking. Start thinking with your head, not your balls. This is not some nefarious plot to take your manhood away from you. Think of these breasts as props, illusions of womanhood. Like a magician they are intended to redirect your audience's attention."

Then with a pleading expression Rose continued, "No phony platitudes Jack, I love you and freely admit you are without a doubt the finest gentleman, the most caring and sweetest person I have ever met. My last lover was hung like a horse, and boy did he know how to use that massive tool. Sex was always incredible, but I dropped him for you. I did that because I love you and want to spend the rest of my life with you. You won my heart because of your sweetness not your virility. You are the only man that I ever bedded that was more concerned about my needs than his own."

Then with a devilish grin she added, "That makes you stand out, even if it is only 5 inches."

"What are we asking you to give up? A little dignity!

"Shit, you lost that a long time ago. Even before this all started, how many times did I interrupt you during tradition intercourse, because what you were doing just wasn't doing it for me and I pushed your head between my legs? You demurely complied and never questioned my motivation.

"Just look at yourself. When I look at you I am not sure if my husband is still here, I certainly don't see a man.

"I truly don't want to be indelicate and hurt your feelings, but let's get this out in the open. Your personal appearance at the best of times is less than robust. You never portrayed the role of machismo masculinity most women sought. Your looks as a man were at best pedestrian. Your musculature build is slim and frail. You do not exude masculine physical prowess, your narrow shoulders, small hands and feet, your lack of facial hair all make you perfect candidate for this part. No woman has ever described you as rugged or handsome. Most of my friends refer to you as cute. Between your diet, exercises, and herbal supplements the majority of what manly muscles you had have already morphed into soft curves. When you try, your feminine persona is extremely realistic.

"Darling, let's be brutally honest. As a traditional 'man'", she used her fingers to make imaginary quotation marks around the word man, "you are a failure!"

Shocked by her candidness and disparaging description of his manhood, Jack openly wept.

Rose could see the hurt and anguish she caused. She felt just a small pang of regret, so she hugged her husband and tried to console him.

"I am sorry, much of what I have said is the alcohol speaking. But that doesn't change the facts you can't go into this thing half-cocked. It's either all in or get out while you can."

Rather than answer, he merely shrugged his shoulders. Jack felt himself losing control of his life. "Excuse me. I need a few minutes alone."

He ran to the bathroom and locked himself in and sobbed uncontrollably. Rose could hear his weeping through the door but nothing she said could get him to come out.

While waiting for her husband to get over his pity party, Rose took the opportunity for a couple more drinks, after a good 30 minutes a crestfallen Jack emerged and plopped on the couch and buried his face in his hands. It took him several additional minutes to compose himself enough to speak, "Rose, you can be really mean and cruel. I feel so emasculated when you talk like that. Why are you trying to hurt me?"

Rose made a pronouncement as if she were a Greek God atop Mt. Olympus, "If you are done acting like some angst-ridden teenage girl I will continue. All I have done is state the obvious."

Her voice trailed away as she seemed too focused on an object far away. "Hell Jack, we can agree that your less-than-impressive member is more a sense of shame than pride.

You haven't been able to give me a baby and you can't even financially support your family. You love going to the ballet, your only real talents lay in cooking and chess. These are hardly he-man endeavors are they? Let's face it Jack, if it wasn't for my salary we would be homeless. Aren't you tired of being a looser?

"You couldn't get a job as a computer programmer so you ended up in sales. That's not exactly worked out for you, has it? You aren't a people person and at the best of times you struggle selling. You're always under immense pleasure, just to make your minimum sales quotas. Your commissions aren't going to improve until there is a major turnaround in the economy."

Jack brook down and had another good cathartic cry right there on the couch. His tears streamed down his cheeks like the flow of hot lava from a volcano.

Rose waited for the weeping to let up, and mustered her supporting argument as she changed the tenor of her logic. Rose light heartedly proposed. "If you won't do this government project, then maybe you should investigate a career field change, something that would better fit your personality and natural talents." She was tempted to add such as interior decorator, hair stylist or manicurist, but felt she had already made her point.

An obviously inebriated Rose continued, "Darling, the nice government man has promised to take very good care of me in your absence. He ensured me of a very generous stipend while you are away. In addition to your government pay as a GS 11. So when you come home we will have a very nice nest egg. That way I can keep the house and even save a little. Aside from being the right thing to do, it will set us up financially.

"Please don't think of this as giving up your manhood, it's just a brief hiatus, a pleasant journey on the feminine side of the street. All we are asking is that you set aside your masculinity for the greater good. Excuse the pun, but Jack why don't you just 'man up' and agree to this procedure! When this is over we will still be husband and wife and will live happily ever after."

Jack wiped his nose with the back of his hand and said, "I suggest you go find yourself a real man, I am sure with the right enticements you could get Mike to volunteer. I suppose compared to Mike I am no man at all?"

"Don't go there, this is not about Mike."

"Answer me, is Mike a better man than me?"

"You are being stubborn, if you want to get into a juvenile cock measuring contest, I'll indulge you. In all honesty, Mike is twice the man you are. He is bigger, stronger, more self-confident, more virile and extremely well endowed." Then after a brief pause she added, "From what I hear."

Rose moved across the room and knelt in front of her husband. She took his hands in hers and stared deeply into his eyes, "Jack, you are testing my patience. Old wham, bam, thank you ma'am, Mike, may be a real stud and the biggest cock hound in town. But you are the only person for this job. Mike wouldn't and couldn't do it. It takes a better person, a better man than him, this job calls for an individual that has balls enough to be a woman. My love, I know that person is you."

"Just get it over with and call me a fucking queer!"

"Oh darling, don't be so sensitive. For heaven's sake, stop with the sad gloomy puppy dog eyes. I am not trying to usurp your masculinity. All I am doing is stating the obvious. Clothes, makeup and a set of small tits don't determine one's sexual orientation. It's what's between the ears and in your heart that's more important than what is between your legs or on your chest."

An emotionally distraught Jack inquired, "I still don't understand why we can't continue doing this using padding?"

"Fine, be like that!" She said with a bit of a scowl in her voice. "What we have done so far is nothing but window dressing. To carry this off you need to feel like a woman and there is nothing that makes a person feel more feminine than her own set of tits. So what say you?

"This is your chance to get rich in self-respect and pride. No one would ever be able to take that feeling of accomplishment away from us. In the grand scheme of things what are a couple pounds of quivering flesh compared to lifetime of self-esteem? The implants can always be removed."

"Let me lay it on the line, if you decide not to do this, then I am calling the whole thing off. I refuse to sacrifice you and send you on a fool's errand. Everything we have done the last few weeks will have been for naught. If you agree to this I won't lie to you, it will be a very tumultuous voyage. But I will be with you every step of the way. You are going to make me so proud. When you have completed this assignment you will be a true modern day hero. We have long lives ahead of us, won't it be wonderful to look back on this period and know we have made a difference! Look at it this way; everyone dies but only a few get a chance to truly live!"

Jack replied slowly, "I'm not looking for a medal, but if I get one I would just like to still have a manly chest to pin it on when this is all over."

Smiling Rose continued, "Oh, poor Jackie, don't you realize that when you are successful, Jack will never receive any public acclaim, all the glory will go to Daisy, so any medals will be draped on nice soft boobs not on some hairy manly chest."

"Can you guarantee me that if I do as you request, that if I, or should I say, when I, come home our relationship will return to the place we were at before this all started?"

Rose paused for a few moments and looked out at nothing, her eyes glazed over before returning her focus back to her husband. "Don't be a fool Jack, no one can do that. Every event we experience changes us in some way, we can never recreate the past. Only God knows what the future will hold. But that doesn't mean the future won't be just as good if not better than the past. The only thing I can guarantee is that I love you and nothing can ever change that."

Jack made a sour face and said, "I'll admit that there times I have enjoyed our little games, but this is such a big step. I'm not sure what I should do."

"Don't be a silly goose, using the term 'enjoyed' is not accurate. I have seen you, I would more appropriately use the terms giddy or even euphoric. Hell Jack be honest, you love getting all pretty in your feminine finery. When you are in Daisy mode you are the sweetest, most demur female on the planet. Jack, it just jumps out at me that Daisy is much closer to your true inner being than Jack."

Jack wore a smirk on his face, "Don't paint me with your emotions and expectations. I don't have a gender dysphoria; I'm a male and want to stay that way! But you are correct, there are times I love getting all dolled up, but I also love Disneyland that doesn't mean I want to live there. Rose, you are turning something that started out as a fun playful game into a sentence. If I have surgery, I can't just wash it off like my makeup. I'm condemned to live as a woman for the foreseeable future."

"Damn your eyes Jack, don't you dare imply being a woman or even living as one is a punishment. It's an honor! To follow up on your Disneyland metaphor look at it like this, over the past 4 weeks you have paid your entrance fee. You're now in line for Space Mountain. Just sit back and enjoy the ride. Please Jack do this for me, do it for us!"

"Rose you know I would sacrifice my life for you. If you needed a heart transplant I would be the first one in line to donate. I admit that female mannerisms, dress and makeup are now almost second nature to me. But what you are asking is for me to…to give up my masculinity."

Rose reached the crux of her agreement, the coup de grace – she played the guilt card. "Alright I know this can all be daunting, but if you don't love me enough to do this one simple thing I have asked of you, then just say so and we can move on. We will make Daisy disappear forever and you can go back to the old, plain, underachieving Jack."

A teary eyed Jack hugged his wife and she tenderly kissed his tears away.

"Damn you Rose you can be a hardheaded, stubborn, demanding SOB!"

"So what's your point Jack? You are correct I can be demanding, but you know what I am suggesting is the best course of action. Now my little, sexy husband just say yes and let's move this thing along."

Mortified that he was again crying like a school girl, Jack wobbled on his feet like a newborn fawn as he tried to push himself away from his wife. She clung to him and pulled his head to her shoulder. It was at this point being held in his loving wife's arms that Jack's resistance broke and he consented to the surgery. Surprisingly, now that the decision had been made, the demons were finally exorcised in his head.

Signing the medical release form, Jack quipped through clenched teeth, "Alright Rose, you win, I guess I am about to become the newest member of the mammary gang. I just hope the club initiation isn't too bad."

Her immediate response consisted only of a Cheshire cat grin. A jubilant Rose rushed off to fax in the forms so he couldn't change his mind then fixed them both a celebratory drink. She was delighted that Jack agreed to the procedure. At best, she had expected a protracted argument; his total capitulation was welcomed but surprising. Thinking, 'Perhaps, I should feel guilty about what we have planned for my poor unsuspecting husband. But, que sera, que sera, whatever will be, will be. The future's not ours to see.'

Getting in bed, Jack turned to Rose and said, "Honey, can we talk?"

"Jackie we talk all the time, now it's late, just go to sleep."

"No Rose you are wrong, we don't talk. You talk and I listen there is a difference."

"Jackie, stop being asinine, you are just tired. You have just made a monumental decision and are probably having second thoughts. Go to sleep, it will all look better in the morning. Now I am not going to tell you again, go to sleep!"

"Rose you can be a stubborn, bossy wife. There are times you can be a bit cavalier about my feelings. I love you more than life itself, I know you are infatuated with Daisy but I need to know, do you still love Jack?"

Rose hesitated, choosing her words carefully before she answered evasively, "You know I love you, you daft sod, now nighty night."

That night after they had retired, Jack laid in gloomy silence staring into the dark. Jack 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 can never deny Rose anything, or did he do it because it is the right thing, or was he easily persuaded into it for some deeper reason? Jack spent the night silently weeping in his soul over this latest turn of events.

While Jack was tormented by his decision, his wife lay next to him with her emotions likewise in fluctuation, bouncing back and forth between feeling actual remorse for her treachery of this poor gullible man and jubilation at being one step closer to her goal.

Rose's last thoughts before falling into a deep sleep were, 'I have my wants and needs, the government has their priorities, if my husband isn't man enough to stand up to me, then that is his problem.'

"Boobs just go to prove men CAN focus on two things at once."