Chapter 29 - Plans Are Hatched

Do your own thinking independently. Be the chess player, not the chess piece.

Daisy arrived back at the apartment and, as was normal, filled Linda in on everything she had observed during her shift. Today she was excited because a new player had shown up at the club: A dark-skinned bearded man, with long greasy hair who looked like he had just learned to walk upright. Ivan had greeted him like a long lost relative and even Ivan's bodyguards were deferential to this guy.

He and Ivan went off together and talked for several hours. Under the pretense of taking a drink order Daisy had approached to eavesdrop. Ivan noticed her and waved her away before she could hear anything. Daisy gave Linda a description of the man, but was unable to provide any useful intelligence. Linda added the information to her report. Daisy had been very successful in establishing a detailed profile of the men who Ivan associated with.

Linda waited patiently for the end of Daisy's report. Unable to contain herself any longer she sat Daisy down for a chat, "Listen to me, something big has come up concerning your mission, it took the FBI a while but they found his last girlfriend a young man – a lifelong cross dresser Ivan named Lusty Laura, who is now living in Denver. She told us that being a mobster's plaything was not all fun and games. At first, they spent every night partying with lots of the beautiful people, plenty of booze and drugs. Ivan lavished her with gifts, jewelry, clothes, perfumes, and even furs."

Linda saw the relieved look on Daisy's face and had to put a stop to that right away. "Listen to me, that all changed in a heartbeat. Daisy, this is serious business, one mistake and we may find you thrown out with the trash! Laura told us that Ivan keeps a PC in his cabin aboard his yacht. Laura, who in his previous life was a married computer programmer, stated to his interrogators the computer was password protected.

"Laura says that his downfall came one day when Ivan had been drinking heavily. After a robust bout of sex, he left the cabin to find a fresh bottle of Vodka and had left the computer logged on. While Ivan was out, Laura went to the computer to see what Ivan was so paranoid about. Laura had just gotten into his documents folder when Ivan returned and found him sitting in front of the computer.

"Ivan went berserk and dragged him away from the computer by his hair. Ivan beat on him to a point that Laura was knocked out. He woke up in a Mexican clinic that Laura recognized as the same one he had been taken to for his feminine remodeling and the pièce de résistance, his leviathan sized breast implants.

"However, instead of giving this time, they took away. He was castrated and shipped back to Miami. Upon HER return, Laura begged for forgiveness. The bastard laughed in her face and had his henchman drug her and put the newly minted eunuch on a bus for Phoenix with no money and a dildo stuffed up her ass. Before she fell out of favor, Ivan had cosmetic improvements done to Laura, which made her not only passable but eye-catchingly beautiful. As a result, Laura was attractive enough to initially get a job in a swank bordello that catered to the kink crowd. Being an attractive shemale she did a thriving business until she got canned for stealing from one of her customers. She has been in and out of mental wards and now makes a living working the streets selling her services.

"Based on her information, the tech guys have come up with this little gem, a byproduct of the cold-war."

Linda showed Daisy a tiny electronic device about the size of a dime. Linda explained, "All you do is peel the tape off the back and stick it to the underside of his laptop computer. It will capture every keystroke made, thus stealing all of his logon passwords. Then, at some future time, we combine it with a special thumb drive allowing us full access to the hard drive."

With a mischievous grin Linda said, "All we have to do is get you aboard his ship so you can place this on his computer."

"Daisy, I know you have been very friendly with Ivan. Recent intercepts indicate he is planning a dinner party on his yacht. You need to try and get an invitation. I've been telling you to play hard to get. Well this changes everything; we need to up the stakes. I now want you to flirt with Ivan every chance you get, make him think you are not only available but willing. We will get you the complete layout of the ship. Once aboard the ship all you have to do is find a way into his bedroom so you can plant this little device. Do you have any questions?"

"What exactly do you mean available?"

"Don't be naïve, you're a big girl. We have been over this. You'll do whatever it takes!"

Jack suddenly felt cheap and worthless, he knew this moment had been coming but it still made him feel emotionally destroyed, and like a cheap sex object. He sadly inquired, "That sounds extremely dangerous. How do I get the bug aboard the boat without getting caught?"

"Daisy let me worry about that. You just concentrate on getting invited to the party. I have it all figured out, in the end it won't be a problem."

Daisy started for her room and unexpectedly stopped, she turned back to Linda and pleaded, "Please, tell me, what your plan is!"

Linda thought for a moment and decided Daisy was well enough conditioned to be let in on this part of the plan. "Okay come with me, I'll show you. Laura told us she was searched from stem to stern every time she was invited on the ship. That only leaves us one choice for smuggling something this size aboard."

Linda led Daisy into the bathroom and took out a box of tampons from the cabinet. Jack's mind was working at high-speed and a thrill of fright went through him. "Linda, what the hell are those for? Please tell me it isn't what I think."

Linda looked Jack in the eyes. "Daisy, you need to get something onboard the ship. From what we know about Ivan's security this is the only way. This is low tech, smuggling 101. Just watch me and then we will get to your participation."

She quickly removed her skirt and panties, standing before Jack in just her garter that held up her sheer nylons. Jack beheld Linda's deliciously bare crotch and remembered sadly the last time he had had sex as a man. He didn't really register the fact that there was no response from his restrained cock. He quickly looked up to Linda's face before she realized that he had been admiring her. He did not want her punishing him.

"Do you know how to use one of these? Probably not; so let me show you how these work. First, we put this little tech device inside this specially designed hollowed out tampon. Then, I spread my pussy lips to open my vagina. I place the applicator at the opening and gently insert it, pushing slightly toward my back. First timers sometimes feel a little discomfort, but that soon stops. Now I take the little string here and hold it against the outside of the plunger and push with a nice steady pressure." You can feel the tampon enter as you depress the plunger. Okay, once it's all the way in. I release my finger on the string and slowly withdraw the applicator like this. See how the string slides through the applicator? When I'm done the string hangs down. Next you'll want to give the string a little tug just to make sure the tampon is properly in place. There should be just a slight resistance."

Linda stood up erect and spread her arms and legs, proudly displaying the telltale white thread between her legs. "See, that's all there is to it! We have these specially made tampons that are hollow and ideal for concealing small devices. Now it's your turn."

Jack blinked at her for a moment. "But I don't have…what you have. Men aren't built for those kinds of things."

She looked at him as he were actually as dim as he seemed. "I know that silly, the great thing about these devices is they work in any dark orifice."

Jack started to object, but Linda cut him off with, "Don't be such a baby, lots of men have incontinence problems, just think of it like that." She got right in his face and said, "To ensure you don't give away that there is something secreted in your special hidey-hole, I want you to become accustomed to wearing these. Every morning, I will watch you put one in. In no time it will become second nature, trust me."

"Yuck, Linda this whole thing scares me shitless." This was just one more humiliation that Linda was visiting upon him.

Smirking, Linda replied, "If you are wearing one of these up your bum, I would recommend that. Just wait until you are home to do your business."

Jack put the applicator at the entrance to his lubricated asshole and paused. He pushed upward on the inner tube, missing the cavity he was shooting for and the tube dropped to the floor between his legs.

Watching Daisy's first clumsy attempts at inserting the tampon had Linda laughing so hard she couldn't breathe.

Jack's second attempt finally produced the white string hanging out his boy hole.

"All right Linda I have finally got it in, now how do I get to his stateroom without raising suspicion?"

"Let me pass long on old military maxim; you improvise, adapt, and overcome. If you screw this up, you'll be fucked more ways than one. But I promise I'll give the eulogy at your funeral."

@ @ @ @

The next day was Saturday. Daisy did not have any tutorial sessions scheduled; nevertheless he dutifully cleaned the apartment to Linda's exacting standards. Meanwhile across town, Phyllis had her husband take a long hot perfumed bubble bath. While still in the bath, Phyllis delivered his liquid breakfast, of tea and a protein shake which this morning was heavily laced with diuretics to encourage frequent urination.

Steve was stopped dead in his tracks when he saw what was laid out on the bed. "What's that?"

Phyllis had a grin as wide as the Grand Canyon. "Oh you'll really enjoy this disguise, well more accurately I'll enjoy it.

"I positively guarantee no one would ever think that you're a man when you're wearing it. It's a technical miracle called the Empathy Belly Pregnancy Simulator. This will let you know what it feels like to be pregnant! It is a multi-component, weighted garment that will, through medically accurate simulation, enable you to experience over 20 symptoms and effects of pregnancy, including weight gain. With the straps firmly synched you will only be able to take shallow breaths thus causing shortness of breath, that most expected mothers go through. It will even increase your blood pressure, pulse and body temperature."

Phyllis poked the mound of padding that constituted the bulk of the contraption. There was very little give to it.

"The positioning of the weight, over 30 pounds if I remember correctly, will cause increased bladder pressure, which in turn will created the need for frequent urination. You'll experience low backaches because of the shift in center of gravity, walking will become more of a waddle. You'll fatigue easily and best of all you get to appreciate the pleasure of carrying around dropping breasts the weight of small dumbbells and the size of soccer balls. The only thing it doesn't replicate is swollen feet, I'll take care of that by having you wear shoes a size too small."

Steve vehemently objected, "This is over kill. I only need a disguise, I don't need all that other stuff."

Phyllis sat down on the bed. She knew that the next few hours were going to be physical and emotional torture for Steve, but none of it was permanent. This was something that she hoped would be the start of Steve's reconstruction as a man and as a member of the human race.

"Honey, listen to me. You are the one that told me you were being followed. You said it was critical that no-one connects you to this Rose woman. Even if someone saw you coming home in your teenybopper regalia, the last thing they would be looking for is an expectant mother. This getup will have you looking and acting like a woman in her third trimester."

Still not convinced Steve continued to object, "I can just add padding, a pillow perhaps."

"You can't possibly be that dumb! Steve you've run undercover ops. Being knocked up is not something you can fake with a feather pillow stuffed under your shirt. It will only be believable if you are fully immersed in your character, you need to know what it like is to be a woman during spawning season!"

Steve was furious, the veins in his neck stood out. Phyllis tried to settle Vesuvius down before it could erupt. "Relax dear don't go getting all Pregzilla on me!"

"This is the real genius of my plan. Rose and I have agreed on an ideal meeting place where we will be able to ensure our privacy."

"You’ve talked to Rose? How?" Contact between Phyllis and Rose could be as dangerous as if he were calling her.

"Of course I have. I found her contact information in your cell phone. By the way, using your birthday as your unlock code isn’t the brightest idea. I used my cell phone to call her and not yours. Rose and I had a nice chat and decided that even if a thug was to tail any of us, no mobster is going into a woman's sanctuary like a maternity shop. If they did, they would stick out. Let's get you dressed we're to meet Rose at Babies-R-Us in thirty minutes."

Phyllis handed Steve a pair of control top panty hose. "Start with these dear; make sure you tuck your male parts back out of sight."

Steve stood and pulled up the pantyhose. Phyllis approached from his front and stuffed a maxi pad between his legs. "What is that for?"

"Woman in your condition often have a problem with incontinence, this will catch any unplanned leakage."

The stockings firmly in place, Phyllis made him put on a pair of pink lace panties over the top of the hose, knowing he was going to have a hell of a hard time when he had to use the toilet. She then gleefully helped Steve into the simulation suit.

His blossoming boobs fit nicely into the faux breast cavities. To ensure his breasts would react to the suit's movements, Phyllis copiously coated the cavities with adhesive. She added a dab on his sensitive nipples and areolas so every movement would pull on them. Phyllis explained this was necessary to add realism. This way he would react like his breasts had feeling and weren't just two large airbags attached to his chest. Phyllis stood and made the newly christened Desiree promenade around the bedroom several times.

The suit worked better than she had hoped. The randomness of the movements of his exposed belly and breast were perfect for Phyllis's purposes. They appeared to always be a half step behind his movements. When Desiree tried to stand up straight and walk in his normal manly manner, his breasts swung back and forth wildly and looked like the balls of a cheap executive pendulum toy. Phyllis smiled at her husband's reaction when he felt the tug on his sensitive breasts as the suits tits bobbed up and down and swung from side to side. Desiree folded his arms across his chest in an attempt to control their undulation, it was almost comical. To control their motion he tried walking hunched over. In this position the breasts almost touched his protruding tummy.

Phyllis finally took pity on him and showed him if he stood up straight, with his arms at his side and took slow small gliding steps, the massive oscillation of his boobs and belly were kept to a minimum. She held up the maternity dress and said, "It's hard to dress stylishly with a large belly bump so I found the most feminine outfit available for a woman…of your dimensions."

"But my God, it's all pink and covered in lace."

"Exactly, but don't worry I'm sure it'll fit, I bought the big Momma size."

Phyllis laughed a little too loudly from Steve’s standpoint and said, "Being a knee length skirt, you'll have to keep your knees together when you sit to keep from flashing everyone."

"Isn't that over the top girlie?"

"Exactly, aside from protecting your real identity, it might just teach you something about what we women have to go though. You are the one that wants a family. The next time you ask for a baby I want you to remember this experience. Now get your purse, run a comb through your hair and put on some lip gloss. We don't want to be late. We'll take my car since you left yours a block away."

It took a shoehorn to wedge Steve's feet into his loafers. Steve stood in front of the full length mirror and looked at himself from every angle. Finally he faced the looking glass full on and rubbed his hands across his extended belly and thought 'I hate to admit it but Phyllis might be right; no one would ever think there is a man behind all this silicon padding. '

Phyllis laughed so hard she had tears in her eye's watching her husband trying to wedge his rotund belly into her compact car. He was really huffing and puffing by the time he got his seat belt on and adjusted between his two massive melons.

For all of the meanness she knew she was subjecting her husband to, Phyllis did feel sorry for Steve. She knew that he was a good man at heart, but he had changed over the years and she was sure that his job was to blame. He really did not merit the torture she was subjecting him to, but this humiliation would be short-lived and would bring some of his upset over his developing bust into perspective.

She would make it up to him tonight when she helped him out of the torture device she had just strapped him into. It was sad that he, like all men, considered the thought of being in that kind of condition as so awful. It was something that she was becoming more and more ready for herself.

@ @ @ @

Meanwhile Daisy was going through his own ordeal, his feminine hygiene product firmly in place Daisy combed his hair in a sexy side swept bangs style, and applied her new sequined eye shadow. Coating her lips with a scarlet lipstick he decided on wearing his most tawdry top, a sexy, loose fitting chiffon blouse with a deep v cut neckline, which accentuated his limited assets to their maximum. Daisy knew if this outfit didn't get Ivan's motor running nothing would. Unfortunately he still had to get to the club. Daisy's walk to the club attracted a great deal of unwanted attention. He felt relieved when he finally reached the security of the club. Daisy had just started his shift when in walked Ivan with his entourage. Ivan assumed his normal seat while his body guards spread out throughout the clubs and in Daisy's opinion they spent more time ogling and flirting with the waitresses than scanning for possible threats. A fact he made a point of to report to Linda.

Upon seeing Ivan, Daisy locked eyes and sashayed over to him determined to play the stereotypical blonde bimbo. Daisy lightly rested his hand on Ivan's forearm and licked his painted lips. Ivan immediately invited her to play a game of chess. Daisy sat and crossed his nylon-encased legs at the thigh, a pump dangling from the tips of his manicured toes. Daisy played with his hair as he contemplated each move. Half way through the game Daisy captured one of Ivan's bishops. Unable to beat Ivan using conventional tactics, Daisy decided to use his womanly wiles. Rather than place the piece on the board, Daisy leaned over the board towards Ivan and played with the piece between his fingers, slowly caressing it up and down its length. Then Daisy brought the cylindrical piece to his mouth and was sucking on the piece, pumping the slender tube in and out of his mouth. Ivan looked up and realized his opponent was trying to distract him so he firmly told Daisy to "KNOCK IT OFF!" A startled Daisy said, "Yes my liege" then clumsily dropped the piece. It plunged exactly where Daisy intended and disappeared into his cleavage. Making a real show of it, Daisy spent several minutes fishing for the missing piece. Producing the lipstick stained chess member, Daisy said "Gotcha you slippery little bastard!"

An amused Ivan, replied, "It's probably a good thing your bosom is not in full bloom or we would be here all day.

In response, Daisy reached up with both hands and rearranged her breasts. Giggling Daisy countered with, "Admittedly I am mammary challenged. But if you think small can't be effective, you have never been trapped in a bedroom with a mosquito. Besides haven't you heard anything over a mouthful is wasted?"

Ivan laughed and said, "Daisy you are a diamond in the rough, your naïveté is a breath of fresh air. Whoever said that foolish thing has never titty-fucked a large breasted woman."

Daisy's dramatic performance was not in vain, aside from losing the game. The first thing the next morning a messenger delivered an invitation for a dinner party on Friday night aboard Ivan's yacht.

"A woman's best friend is a purse full of condoms, tampons and maxi pads."

@ @ @ @