Jimmy Olsen Shemale Bimbo Ch. 01-02

Story Info
The beginning of how Jimmy became Gemmy.
3.1k words
4.28
31k
17

Part 2 of the 6 part series

Updated 06/14/2023
Created 07/29/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 1 - Junior reporter on the job!

Jimmy ran the brush through his shoulder length hair one more time and stepped back to admire himself in the full length mirror. The wig looked good. It was the same wig he wore each time he dressed up. He took the cap off of the lipstick tube and applied a generous coating of the scarlet wax to his lips, and then blotted off the excess with a tissue.

He was ready. He pulled a light sweater over his blouse, careful not to snag it on his newly painted long nails, picked up his purse and set out from his apartment. He remembered to sway his hips as he walked in the two inch open toed heels, the rhythm coming back to him naturally.

In all of his adventures with Superman, Jimmy had been through many startling transformations - a porcupine boy, a giant space turtle boy, a werewolf, a vampire... he HAD been a vampire, hadn't he? He had been through so many bizarre changes that it was hard to remember them all.

But his favourite transformation was this simple one, when he took a couple of hours to become his feminine alter ego. It had started as a necessity a couple of years ago - to convince Perry White to hire him back at his job he had disguised himself as "Leslie Lowe." Then he had become "Jackie Oliver" in order to pick a new leader for his fan club. Most recently, just a half year ago, he had gone undercover as "Julie Ogden" a chorus girl in order to catch local gang boss, "Big" Monte McGraw.

But along the way, Jimmy had found that he liked the feel of the silk panties, the garter belts and the hose on his legs. He liked the scent of the lipsticks, and how the eye shadow set off his green eyes. He got an erotic thrill dressing up and then slowly disrobing so that he only wore the hose and garters, slowing masturbating his cock as he watched the pretty girl in the mirror languidly smoke a cigarette.

Even now as he hurried down the sidewalk to the cab stand in front of the nearby hotel, his cock was fully erect in his panties. Fortunately he had put on tight panties and a loose skirt so that no one would notice a bulge when he arrived for the interview. Perhaps he should have jerked off before leaving, but he had run out of time. He had almost forgotten to paint his toenails! When he got home tonight, after getting the job - THEN he could lube up and slowly bring himself off!

His momentary reverie was broken by the wolf whistles from the construction site. Men were such animals! He LOVED the attention! His cock felt as if it would burst!

While Jimmy now wore panties and stockings most of the time when he was at home, he rarely wore them under his work clothes. He could not predict when he would have some bizarre adventure with Superman and his outer clothing could burst open to reveal his feminine attire.

However, Jimmy did dress up and go out in drag a couple of times a month. Usually he took cabs to transvestite bars in the seamier part of Metropolis. There he either found women to chat to, or sometimes let men buy him drinks. He even danced with those men occasionally, and was turned on by the naughty suggestions that they whispered in his ears as their stiff erections pressed against his thigh!

But it never went further than that. Oh yes, when he got home after such evenings, he would freshen his lipstick and then excitedly wank off and spurt his cream on the mirror as he admired what a sexy bitch he was; but up to this point anyway, he had never had the urge to share his passion more intimately with someone else. Well actually, he had to admit that the urge was there. He was curious as to what it would feel like to have another man's cock in his hands, and on his lips. But he knew that he needed to be discrete and so had resisted, so far.

In the back of the taxi, Jimmy took a compact out of his mirror and checked his makeup. It was fine. He lit up a cigarette. He was normally repulsed by smokers but as a woman he found the act of smoking to be damn sexy, and it helped to calm his nerves. He stubbed out the cigarette as the taxi arrived at his destination.

When he had last cross-dressed for work purposes, it was Jimmy's undercover work that had led to "Big" Monte McGraw going to jail. Unfortunately, Monte's lawyers had been sharp and it had only been a couple of his hired thugs who had been convicted of more serious crimes. Still, Monte McGraw was off the streets for 2 to 4 years. But that hadn't stopped him from running his gang through his brother "Little" Danny McGraw.

Jimmy's sources had told him that Danny was interviewing for a new secretary this afternoon. He had gotten the word only three hours ago and had rushed home to prepare himself to come in drag and interview for the position. Jimmy was sure that he could doll himself up enough that he would be a shoe-in for the job. Once he was in Danny's offices, it would take him only a couple of days to get the evidence to put Danny in a cell beside his brother.

As Jimmy walked through the front door of the small office building, a hoodlum lounging on the corner quickly entered a phone booth and made a call. "He's here. He just went in the building. He'll be upstairs in a minute."

The ride up the elevator was brief. Jimmy remembered to sway his hips as he opened the door to the suite at the end of the hallway. He took one step inside, looked around for five seconds, and then quickly left and took the elevator back downstairs. On the street he quickly fumbled in his purse for a cigarette. Once it was lit, he hurried down the street, trying to hail a taxi and get him out of there!

Guido saw Jimmy leave and hurried upstairs. He brushed past the several women waiting in the outer office and barged into Danny's inner office. "What happened"

"I don't know," said Danny. "Olsen took two steps inside the door, looked around and then skedaddled!"

"It was definitely him, right?" asked Guido.

"It was definitely Olsen. Same dumb looking wig - I can't figure out how Monte was fooled. But also, the stupid jerk was still wearing that dumb Superman watch of his!"

"So what made him run off?"

"I don't know. I was sure he would show up dressed like a dame, when we put out the word that I needed a skirt! Maybe he didn't like the competition? Get rid of the other girls and we'll just have to hope he comes back later, or tomorrow. Monte really wants to get his revenge on that guy. But we got to get him inside the door for longer than thirty seconds!"

Chapter 2 - A more clever disguise

Jimmy's heart was thumping hard in his chest. He had indeed been scared off by "the competition". There were five other gals in the waiting room, all of them gorgeous. How could he possibly get Danny to pick him, when he would have been the plainest Jane there!

So how COULD he get hired? Well, he could always ask Lois to do this for him. She was more beautiful than any of the women back there. But no, Jimmy wanted to bring McGraw's criminal empire to its knees all on his own.

Lois... hmm... now THERE was a thought. Yes... that would work. But, he had to get someone's attention first.

Jimmy made his way to a small park and sat on a bench. He lifted his arm and with his other hand he squeezed two knobs on his signal watch simultaneously. He knew that this sent out an ultrasonic zee zee zee zee sound which even dogs could not hear, but which Kryptonians could!

Unfortunately nobody had seen Superman for the past three months. He might be in space, he might be dead for all that anyone knew. The rest of the superhero community was not saying. However, Metropolis was still being protected by....

Supergirl slowly descended from the sky above.

"Jimmy? Jimmy, is that you?"

"Um, hi Supergirl. Yeah, I'm undercover... or at least trying to be undercover, but I need your help!"

"Jimmy. I can give you a few makeup tips, but really...."

"Not that kind of help. Listen...." and Jimmy explained, from first getting the tip, to fleeing from the office building.

"And I can help you... how?"

"Lois told me about a machine in the Fortress... the machine which another Kryptonian used to turn her into his ideal mate... and then later she convinced Superman to use it to turn her into a black woman for that "Black Like Me' piece that she wrote. I want you to use the machine to transform me into a beautiful woman for a few days... just until I can get the evidence that I need. Then you can change me back again"

"Okay, I'll do it"

"Just like that... no convincing?"

"Just like that," Supergirl replied. She scooped up Jimmy, careful not to mess his wig, wrapped him up in her cape, and flew at superspeed to the Fortress of Solitude in the Arctic wastes of Canada.

Jimmy had thought he would have to argue much harder with Supergirl. It would have been better for Jimmy if he'd had to. Supergirl had her own motives, and those motives were for a bit of revenge! Nothing harmful, nothing lasting, but Mr. James Bartholomew Olsen needed taking down a peg or two, she thought.

While Jimmy had encountered Supergirl a few times during his adventures as "Superman's Pal ", he did not realize just how intimately he had gotten to know her. And that was of course because he did not know that her secret identity was Linda Danvers, Clark Kent's cousin.

Last summer Linda had worked at the Daily Planet as an intern during her first year of college and the nineteen year old had become quite smitten with the adventurous Jimmy Olsen. Jimmy had taken advantage of that adoration and had taken Linda out on several dates. On each successive date, Jimmy had gotten a bit bolder, a bit... fresher. By the fourth date, the two were necking heavily at the end of the evening and Jimmy had managed to squirm his hand under Linda's bra and massaged her sweet young titty. By the sixth date, they were ending the evening back at her room, with him tonguing her nipples as she massaged his erection through his trousers.

"Oh baby, that feels so good," moaned Jimmy. He stood up and quickly dropped his trousers and his underwear, his erection springing to full attention.

"Jimmy! What are you doing?" cried Linda. "I'm not ready for anything more..."

"Oh come on Linda! You've been prick teasing me for the last several dates. It's time to put up... well, put OUT actually". He leant forward, and before she could protest, Jimmy had slid his cock into her mouth! She was about to chomp down and show him just what a super girl could do to an unwanted invader, when she sighed and realized that she was going to have to start doing this for boys at some point. That cute Robin sidekick of Batman had been urging her to do similar whenever they were alone together - and he was a year younger than her!

Jimmy had grasped her head as he fucked his cock in and out of her mouth. Fortunately, her Linda Danvers brunette wig was very securely fastened. She did not need the hassles of having to explain her own blonde hair underneath. As she tongued his cock, Jimmy flipped her flat onto the couch and reversed his position so that he could work on removing her sopping panties. Soon his tongue was giving her pleasure as he licked at her pussy. Fortunately he did not notice that the fine blonde pubic hair did not match the color of her wig!

"Mmmmmmm..." she moaned as his tongue flicked rapidly across her clit.

"Allura, the Star Princess of Vega 3 taught me how to do that," said Jimmy smugly.

Jimmy reversed himself again and grasped Linda's legs, spreading them wide. His cock was rampant. "No," cried Linda. "I'm still a virgin. You can't!"

"I can, and I will!" said Jimmy as he nestled his glans between her sweet young lips and pushed...

And stopped. He pushed harder. Linda wriggled underneath him, fighting him. But Jimmy persisted. However his cock would barely enter her. Linda let out a sigh of relief! Her hymen remained intact and no mere earth man was going to break it!

(It would be another three months before Kara Zor-el was deflowered. She could have taken a trip into the bottle city of Kandor and found a man there to take her virginity. She could even have followed in her mother's wicked footsteps and taken advantage of Comet, Beppo or Krypto - any of the Super Pets - to "break her in." But there was only one man whom she yearned to have as her first lover, and that was her cousin Kal-el - Superman. She was finally able to do so when she used a piece of red kryptonite which gave her the ability to turn Superman into a Super Satyr for 48 hours. She had used it on him one weekend in the Fortress and at the end he had forgotten everything, but she had walked/hobbled away with a well fucked pussy and an insatiable thirst for kinky sex)

Jimmy was not to be thwarted though. He removed his dickhead from her pussy and moved it lower. He probed at her anus briefly, and then with a single thrust he buried three inches into her ass. Linda let out a shout of surprise and screamed at him, "You bastard. Get that thing out of me before I rip it off of you!"

"Relax doll. Most girls your age are into anal sex. They want to save their virginity for the right boy, but they figure that taking it up the backside doesn't count!"

"Get it out!"

But Jimmy did not need to. All of Linda's twisting and squirming had stimulated him enough that he came quickly and squirted his seed into her butt!

Jimmy had hastily left after that. Linda had not returned to the Planet offices for the last three weeks of her internship. That night she had showered and washed herself dozens of times, and then she had flown to the sunken city of Atlantis and wept in the arms of her mer-boyfriend, Jerro.

Supergirl was now delighted to be able to get a bit of revenge on the self-absorbed cub reporter!

After Supergirl used the giant key to unlock the Fortress door, she led Jimmy to the large chamber where her cousin stored all of the dangerous technologically advanced machinery. Jimmy was in a hurry and quickly disrobed, stepping into the machine, while Supergirl studied the machine's manual and figured out how it worked.

"Any preferences?" she asked Jimmy.

"Not really. I just need to look hot! Oh, and keep me a redhead!"

"Okay, I'm not going to do anything radical. Just tweak your DNA so that you will look mostly like you would if you had been born female, but I also have to make sure that you look good enough to entice that crime boss!"

Supergirl quickly programmed the machine and then threw the switch. There was no flash of lights, no electrical arcs.. Jimmy momentarily flickered and then suddenly there was a pretty young woman standing in his place!

"Is that it?" he asked

"Yes," replied the Girl of Steel, "take a look in the mirror!"

Jimmy stepped out of the machine and faced the full-length mirror that Supergirl had set up for him. 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.

"What?" cried Jimmy. "You were supposed to make me female."

"I couldn't," lied Supergirl. "If I had given you a vagina and internal reproductive organs, you may not have been able to return to your true shape! The machine cannot actually change your sex." As part of her revenge, Supergirl had 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. She doubted that he would notice either of those changes, nor that she had increased his hormones so that he would be constantly aroused. She suspected that having a female form would have done that to him without her ramping up his libido.

Jimmy twisted and turned, admiring his sexy body in the mirror for a couple more minutes. But when he donned the underwear and dress that he had previously worn, they appeared frumpy on his new frame. "Take me back to my girlfriend's apartment, please!" he told Supergirl.

"Your girlfriend?!?"

"Yes, Lucy Lane. Lois' sister. She is a stewardess and is away for several days on a round the world flight. She'll have outfits that will fit this new body!

Two hours later, Jimmy was soaking in a bubble bath in Lucy's apartment. He had his long red hair pinned up high on his head to keep it out of the water. He had an ashtray at the side of the tub where his half smoked cigarette burned. He tingled to see the lipstick ring around the filter, left there by his own painted lips. One finger strummed a nipple on his perky breast (he had real tits!!!!) while his other hand slowly teased the head of his penis, twirling the suds around the glans, sending chills up and down his long shapely legs.

As his climax hit, his leg muscles tightened, almost cramping, and five jets of jism flew from his dick and landed on his chest, his breasts and his chin.

Jimmy mewed with pleasure. He knew... he KNEW, that tomorrow he would have no problem getting that job with Danny McGraw and would put the small time gangster behind bars.

But tonight, there was time for a few more pulls.....

To be continued...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 4 years ago

Would absolutely love to see you continue this

Share this Story

Similar Stories

A Big Side Effect A girl's medicine causes a strange...growth. And urges.in Transgender & Crossdressers
Be Careful What You Wish For Larissa sells her soul and gets more than she bargained for.in Transgender & Crossdressers
The School Tramp From Nerd to Bad Bad Girlin Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
Horse-cock Girl After a field trip, Amy grows a surprise.in Transgender & Crossdressers
More Stories