Jimmy Olsen Shemale Bimbo Ch. 03-05

Jimmy Olsen - Shemale Bimbo

by Mistress Tawny Suede

Chapter 3 - Undercover!

In the morning Jimmy got up extra early to prepare. He HAD to land this job with "Little" Danny McGraw so that he could go undercover and prove that Danny was running his brother's criminal operations in his absence. If he could get the job as Danny's secretary that would be a start. Then once Danny trusted him enough to leave him alone, he could search the office and anywhere else for the evidence he needed.

He had gone to McGraw's offices yesterday in his best female disguise but had turned around and fled when he saw all of the other attractive women who were waiting to be interviewed. Jimmy was an expert at disguise and with his youthful looks and slim figure he had no problem passing as a woman, but he had to be sure that he was chosen.

With Superman missing, Jimmy had turned to the Man of Steel's younger cousin, Supergirl for help. Surprisingly she had agreed readily to Jimmy's plan, and shortly thereafter she had flown him to the Fortress of Solitude and there had used a Kryptonian machine to alter Jimmy's body. The machine had tweaked his DNA so that he looked mostly like he would have if he had been born female.

When he stepped out of the machine and faced a full-length mirror, he found himself looking at a very beautiful young woman with shoulder length red hair, pouty lips, B-cup breasts, a delightfully slim waist, a very rounded ass... and a penis. Supergirl explained that she could not remove all of his masculinity or else the change would be permanent. This was a lie. She actually wanted to get a bit of revenge on Jimmy for past transgressions. As part of her revenge, Supergirl decided to leave Jimmy as a functioning male, although to all other appearances a stunning female. She also did not tell him that she had altered his mind to be more emotional, and more suggestible and ramped up his libido.

It was the morning after. Jimmy had spent the previous evening taking a long perfumed bubble bath. He had planned to shave his legs, a routine that he quite enjoyed, but had discovered that his transformation had left him hairless below the neckline. So he had just spent the time playing with his new breasts and jerking his cock leisurely, edging himself deliciously.

Over the years, Jimmy's crossdressing had started as a necessary disguise in his crime reporting, to a casual flirtation with kink, but it eventually became almost an obsession. He had come to the point of wearing stockings, panties and makeup most of the time when he was alone in his apartment.

Now, in his greatest feminine transformation yet, he actually had pert breasts of a nice size, an attractive feminine face and a body shape that any starlet would be proud of.

He had spent that night at the apartment of his girlfriend, Lucy Lane. She was a stewardess and was away for several nights. Once he saw his new body, he realized he would need to raid her wardrobe, as none of his own outfits from his disguise closet would do justice to his new femininity.

Two and a half hours after waking he was ready. He had spent the time in a wonderful shower, soaping up and exploring his new body shape. Rubbing the loofa over his new nipples had made them so rigidly hard that he'd had to soap up his cock and beat off to a nice satisfying cum! He had then spent considerable time at her makeup table getting the shading of his eyes and his lipstick colour just right! And then it had taken him considerable time to settle on the right outfit for the interview.

He walked out of the front door of Lucy's building wearing a very short skirt and dark stockings. He was very comfortable in the four inch heels, since these days he always wore heels around his apartment. He had chosen to wear no bra and a low cut blouse to show off his new cleavage. He purred as his new tits bounced delightfully. He hailed a cab and just a few minutes later he entered the outer offices of McGraw's company.

He was surprised to find the room empty. Was he too late? Had McGraw already hired one of the women from the previous day? He sat down and waited. Since there were ash trays laid out, he took a cigarette out of his purse and lit it. As a guy he hated being around smokers, but had to put up with it - like the Chief's cigars. But when he was dressed as a girl, there was something irresistibly sexy about a cigarette, and especially seeing his own lipstick staining the filter. Oooo, he had to be careful. His cock was tightly packed away, and he did not need anything trying to give him an erection!

Danny McGraw and a couple of his, um, associates, were sitting in the next office, observing the waiting room through a two way mirror.

"Where is he?" wondered Danny's right hand man, Guido.

"Don't worry. Olsen will show up!" said Danny. "My brother is right. Putting an ad in the paper to hire a secretary will bring Olsen here in disguise."

"Well he showed up yesterday but ran away. Who's to say he is going to show up again today! But you was right, boss, to send away the other dames."

"So why did we get another showing up today? I gotta say, she is quite the looker!"

"Hey boss, I don't know how he did it, but that IS Olsen! Look!"

"Fuck, you're right! How the hell did he do that? That's some disguise! Those even look like real tits!"

Guido had spotted the one thing that would give Jimmy away. Subconsciously, routinely, when he had finished dressing, he had automatically put on his Superman signal watch! Now, the attractive redhead in the waiting room, was wearing that watch!

Danny straightened his tie then he and Guido opened the door.

Jimmy stood and offered his hand. As Danny shook his hand, Jimmy noticed that his own grip was weaker than expected. Well, new musculature inside as well as a hot body on the outside, realized the reporter!

"Well doll, it looks like this is your lucky day. No one else has showed up for the interview!"

"Yes, that is lucky!" said Jimmy pitching his voice femininely. He had practised his female voice a lot.

"Did you bring a resume?" Jimmy pulled a couple sheets of paper from is purse. It was all bogus of course, but if Danny tried phoning any of the references he had made arrangements with those people to give him glowing comments.

As Danny and Jimmy talked, Guido slowly walked around the room, observing Jimmy from various angles. Boy, this guy was GOOD at disguise, he thought. But then, everyone knew he was in tight with Superman, so who knew what alien gizmos or magic amulets he might have used to help him look like this!

"Well, Miss Nelson..."

"Oh, please call me Gemini... or Gemmy if you wish"

"Gemini... an unusual name for a beautiful woman," said Danny.

Jimmy blushed. "My parents were romantics, what can I say!"

"Well, Gemmy... I think I like what I see, and what I read here. The job is yours if you want it. When can you start?"

"Oh, right now, if you want!"

"The job requires you to do standard secretarial duties... typing, taking dictation, answering phones, and some extras. You are comfortable with... extras?"

"Oh, I don't mind running out for coffee... picking up your dry cleaning... buying presents for your girlfriend, that kind of thing! I just need a job!" said Jimmy, hoping that he wasn't missing something else that Danny might be insinuating. Well, hopefully he would be able to find what he was looking for in just a few days and could avoid anything else Danny might have in mind!

"Well, uh, that's fine. There may be a few other things to add to that list, but why don't we get started. Let me show you to your desk." Danny got up and put his arm around Jimmy's waist briefly. Jimmy found the brief touch electrifying. His cock strained a bit. But why was he reacting to the touch of this man, he wondered.

Danny led him back to the outer office and sat Jimmy down at the reception desk. As Jimmy sat, he noticed Danny looking at his cleavage. Using the transforming machine had been a good idea. Now he just had to get the proof about Danny's illegal activities so he could change back!

Danny said, "There are a few changes I'd like to make to your appearance, if you don't mind?"

Jimmy looked at him puzzled.

Danny continued, "I have a certain reputation to maintain with my, uh, business associates. You look very nice, but you are a bit conservatively dressed for their tastes. I want you to dress a bit sexier, if you know what I mean. Shorter skirts, and show off a bit more of those nice tits of yours!"

"Mr. McGraw!" said Jimmy in mock shock!

"Hey baby, if you want the job...."

"Uh, yes I do. I do need this job!"

"Good. Tell you what. I'll advance you a hundred bucks on your salary and give you the rest of the day off today to do some shopping."

"Sure, that would be swell!" said Jimmy. He realized he needed to check in with the office anyway. He began to stand up, but Danny stopped him.

"Wait, there's more. Open that desk drawer." Jimmy opened it to find a number of packs of cigarettes and chewing gum. He didn't recognize the brand names of either of them.

"I like a gal who chews gum. So whenever you're working I'd like you to be chewing."

Jimmy smiled. "Sure thing, Mr. McGraw." He opened a pack and peeled off a wrapper, then popped the stick of gum in his mouth. It had a heavy mint flavour.

"That's it. Much better," said Danny. "And call me Danny. Mr. McGraw is my brother who you'll get to meet, eventually." Danny said that with a sly smile that puzzled Jimmy. "Do you smoke?"

"From time to time," said Jimmy. He of course only smoked when he dressed. It was a fetish thing with him.

"Well, I also like the looks of a gal who smokes," said Danny taking a pack from the desk and offering to light one for Jimmy, who could not refuse. Jimmy thought it strange to be chewing gum and smoking, but....

"Yeah, that's it. Take some gum and smokes with you. Whenever you are on the job, I want you smoking or chewing. It helps with the image!"

Danny handed him ten ten dollar bills which Jimmy tucked in his purse and then left the office.

When he was sure Jimmy was out of earshot, Danny turned to Guido and said, "Well that was easy enough, once the dumb jerk managed to stay in the office!"

Guido replied, "Yeah boss, but it was hard to believe that was a guy dressed as a gal. Those tits, and that ass..."

"Who knows what tricks he has available to him. He pals around with that muscle bound oaf so much..."

"So you think Monte's scheme for revenge is going to work?"

"Sure! Fuck, Olsen has done half the work himself already! And that gum and those smokes Monte had me buy from Intergang should do the rest!"

Guido said, "It's hard to believe what that stuff is supposed to do. Monte said Intergang gets there stuff from some larger outfit called The Apocalypse?"

"Yeah, yeah." said Danny. "Who cares where it comes from, so long as it works! Let's get back to my office. We got a shipment arriving Thursday and I have to decide which warehouse we want to put the stuff in!"

Chapter 4 - The Daily Planet

When Jimmy left McGraw's offices he decided to walk to the shops in the cheaper part of town. He knew the kind of clothes that Danny wanted him to wear and it excited him. Jimmy took out the pack of cigarettes and lit one, smoking as he walked.

He was delighted to have the opportunity to dress in female clothes again, and this time he actually had a woman's body! Well, almost. His cock had become rigid in his panties as he let his mind savour the delight of walking in high heels again and having men turn to watch his ass as he passed them. It definitely turned him on to know that men found him attractive, even though he would never ever do anything about that, of course. Well, other than wank off! He had no interest in actually having sex with a man... did he?

He browsed a couple of stores and tried on a couple of skirts and tops without making a purchase. He had a small lunch - just a salad and coffee since he had to watch his figure now! While eating he decided he could shop for another hour before he should report in to the Planet and fill the chief in on his undercover work. But then he had a brainstorm. He loved pulling tricks on his editor, Perry White, so maybe he should see how long it would take for Perry to see through his disguise!

Jimmy found a phone booth and called the Planet. He told Perry that he had gotten a phone call from a college chum who needed his help urgently on the other coast, to try and break a story about goods being smuggled in from China and that he would need to be gone for several weeks. Perry started to blow up telling him that the Planet could not afford to have him gone for that long!

"I know that Chief, but my buddy and I go way back and we always said that we would be there if one needed the other!" said Jimmy as he pulled out a compact and inspected his lipstick in the little mirror. Satisfied he put the compact away and tried to keep a little laugh out of his voice. "But I have a plan!"

"Don't call me Chief!" yelled Perry White. "But I do understand loyalty to friends. So, what is your so-called plan?"

"You've never met her, and I've never told you about her, but I have a sister named Gemini who is a year younger than me and has been working for a paper in Gotham City. She has a lot of vacation time coming up and has agreed to fill in for me while I am gone!"

Perry yelled some more but agreed to meet Gemmy later that afternoon.

Jimmy finished up his shopping, buying several cute outfits and another pair of heels that he just could not resist! Those heels came out of his own money, but they were so darling! He bundled his packages into the back of a cab and headed to the Daily Planet building.

Perry was sceptical when he met Gemmy, and even suspected that she might be Jimmy in one of his disguises. But Jimmy was showing enough cleavage and his face was so feminine that Perry was convinced this was a woman in front of him!

"Jimmy's sister, eh?" shrugged the editor.

"Jimmy has told me SO much about you! He says he has learned everything he knows about being a great reporter from you!" said Jimmy as he leaned over the desk, giving Perry a good look at his tits. Anything that would distract his attention was good, thought the young redhead.

"I'm not sure I like this, but I can't spare the man power. If Jimmy is not here, then I guess I'll have to give you a chance, Miss Olsen!"

"Thanks, uh, Chief!" said Jimmy in his best feminine voice.

"Not you too!" Perry slapped his forehead in frustration. "Get out of here. Ask someone which desk is your brothers! Figure out what stories he is working on and get to work!"

Perry's secretary, Agnes Frump, gave Jimmy a knowing look as he passed her desk on the way out. A look that seemed to say, I know what you are up to! Jimmy just smiled at her.

Jimmy spent a few minutes doing some tidying up at his desk. While he did that he popped a piece of gum in his mouth and chewed. He did know that chewing gum made him look less professional, but the flavour of the piece from earlier in the day had stayed with him and he suddenly craved another.

As he left the office he also lit up another of the cigarettes Danny had given him. These he knew he had to be careful with since he did not want to become addicted. Then he realized that when he had Supergirl return him to his proper body shape with the Kryptonian machine, she would be able to cleanse his body of the nicotine cravings. So he figured he might as well enjoy the vice! Little did he know the changes that Monte McGraw's plan were wrecking upon him!

Jimmy took his purchases home where he tried each of them on in front of his full length mirror. He also practised more with the cosmetics that he kept at home, and also some new purchases for the day. He did not have as much choice as he would have had, had he stayed at Lucy's apartment again, but he suspected this undercover work might last a week or so and he did not want his girlfriend stumbling in on him using her makeup. He had already had to explain himself once when she had found him crossdressed. This time might be harder considering his tits were just as large as hers, if not larger.

Before going to bed he dragged a free standing full length mirror into his bathroom and set it up close to the shower, leaving the bathroom door open so that the mirror would not steam up as he showered. He stepped into the shower and soaped up his body, all the time watching himself in the mirror, admiring his feminine form - his tits, his ass - and slowly wanking his incredibly stiff dick. When he came, he cried out in joy as his spunk splattered against the shower walls.

When he went to bed he put on one of his frilly nighties that he had owned for years but, for the first time, it enrobed a feminine body.

Chapter 5 - First Day of Work

When he woke the next morning, the first thing Jimmy did was pop a piece of the gum in his mouth. He got up early because he knew it would take him two hours to get his new body and face looking just as he wanted them. He must impress Little Danny!

While walking to the bus stop he was thankful he was wearing a gaffe to hold his cock pulled back tightly between his ass cheeks. All of the men were turning to stare at his new body as he walked on his high heels to the bus stop and it was getting him quite turned on.

He lit his fourth cigarette of the morning while waiting for the bus, and was finishing another when he walked into McGraw's offices to begin his first day of work for the crime boss.

Jimmy sat at the desk all morning, doing some filing and typing one letter. Based on this first morning he was not sure why Little Danny needed a receptionist. Yes, two men did come to visit Danny and Jimmy, or Gemmy, served them coffee and took a few notes before Danny chased him from the room saying they needed privacy. Jimmy was hoping to take a few moments while Danny was busy to begin searching the files in the outer office for evidence that could put Danny in jail but Danny's prime underling Guido, or one of his other men, was always in the reception area with Jimmy.

At times Danny came out from his office to give Jimmy instructions. Danny would lean over Jimmy, sometimes placing his hands on his shoulders or touching him on the waist. Jimmy made sure that Danny got a good look at his new cleavage and reciprocated the light touches. Jimmy found himself getting aroused and a bit flustered around this man. Though he liked to dress in women's clothing, Jimmy's crossdressing had never led to much more than casual flirting with men when he would occasionally go out to a bar while dressed. So he found the idea of being attracted to Danny very odd.

He was frustrated in his attempts to go through McGraw's files when Danny sent him away midday. Danny tasked him with a few menial jobs outside of the office and told him to take the rest of the day off. As Jimmy left, Danny gave his bum a playful pat. Jimmy paused, looked back over his shoulder and smiled at Danny, then left.

Once Jimmy was gone, Guido said to Danny, "Do you think those things are really working?"

Danny replied, "It'll take a few days for us to see any results. Big Monte had us pay good money to Intergang for those cigarettes and that gum so he could get some revenge on that reporter. I can't say I was too happy with what we was gonna have to do as our part in the scheme when I thought we were going to be dealing with Olsen as a crossdressed man. But man, whatever he's done to his body.... I can't say I'm going to be hard done by when this is all over!"

"I know! I've been ogling those tits all day while sitting out here keeping an eye on her.. I mean, on him! Geez, it's hard thinking of him as a guy when he looks like that! Whatever he did, I wonder if he's still got his pecker!" Guido grinned!