Jimmy Olsen Shemale Bimbo Ch. 00

Story Info
Gemmy Olsen replaces her twin brother at the Daily Planet
2.5k words
4.38
33.5k
22

Part 1 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

Prologue.... Six Months Later

In the back of her dim witted mind, she knew that something was not quite right.

In the back of her throat, she knew that Steve Lombard's long hard cock felt so very very good.. If her mouth had been empty... if his balls had not been slapping her chin, Gemmy would have squealed in delight.

"Oh Stevie... feed me your dick! Cream down my throat!" she cooed.

When she was sitting at her secretary desk outside of Perry White's office, Gemmy could actually manage to answer the phone, sharpen pencils and file her nails, although not at the same time. When she was tottering about the office on her four inch spiked heels, her mammoth breasts threatening to topple her over onto her face, she could still manage to put the files away in the cabinets alphabetically... well, almost.

But when she was in the supply room, on her knees with her tongue running up and down a thick juicy cock, her brain cells stopped working completely... she could only focus on one thing... drinking down all the man cum that she could coax out of the thick balls swaying in front of her.

"Jeezus Gemmy... what you can do with your fucking tongue should be illegal!" Gemmy scraped her teeth along his glans, making Steve groan with pleasure, then she resumed bobbing her head up and down on his shaft.

Five minutes ago, Steve Lombard, the sportscaster had gotten off the elevator, coming down from the WGBS TV studios that occupied the upper floors of the Daily Planet building. When Gemmy had spotted him crooking a finger at her, she had stubbed out her cigarette, popped her gum back in her mouth, and freshened her lipstick. She knew that Steve loved to see bright red lips sliding up and down his dick, and she was more than pleased to oblige.

Perry's full time secretary, Agnes Frump had looked at Gemmy in disgust as she hurried away. How Lois Lane had talked Mr. White into giving that gal a job, she could not understand, even if the tart WAS the sister of the Olsen boy.

Gemmy had hurried to the supply closet where she always met Steve just after lunch time - where she always met the many men and boys in the building whom she sucked off. A distant part of her brain remembered that this was the closet Clark Kent had so often rushed off to for supplies. But he had not been around for many months now. Gemmy was disappointed. She dimly remembered that... before Gemmy was Gemmy... whatever that meant... she had always thought that Clark was rather hunky... he had always made her loins go woozy, even when it was not... proper... for her to have such thoughts.

When she reached the supply closet, Steve had hungrily kissed her, his tongue invading deeply into her mouth. Gemmy had coughed and pushed him away. She pulled the chewing gum from her mouth and stuck the wad underneath a shelf in the corner where she could retrieve it later. Her boyfriend, Little Danny McGraw told her he wanted her to chew the gum all the time. He said it helped her to look like an airhead bimbo, and that was the kind of gal he liked for a girlfriend. And who was she to argue with the biggest crook on the east side of Metropolis. So she chewed the gum which he constantly supplied to her. And you know, it worked. She never worried about anything. She never THOUGHT about anything.

As usual, Steve had practically ripped open Gemmy's blouse and torn off her bra so that her mammoth tits were free for him to maul with his hands and his lips. The tits were also gifts from Danny. He had paid for larger tits, several times; and the rings that hung from the studs pierced through the nipples.

Gemmy kissed Steve back greedily. Steve was a good kisser and always got her aroused. She always had to be careful with him; always had to keep his hands away from her panties, from her not-so-little secret.

But Steve rarely ventured there.... he was a tit man and as always, he pushed Gemmy to her knees so that he could slide his pre cum slicked cock through the cleavage of her breasts. Steve mashed her tits together and fucked his cock between them for a minute, before pulling her head back with a firm grasp in her flaming hair, and forcing his glans between her glistening lips.

With no hesitation, Gemmy took Steve's cock fully into her throat and felt his pubic hair tickle her nostrils. As fast as Steve had been on the football field, he was equally quick on the trigger and it was only a minute more before his cum splattered into her mouth. She swallowed greedily, but she knew to not drain it all. Steve loved facials, and he pulled out in time for his last few bursts to coat her face and tits with his delightful slime.

"Spray me Stevie! Spunk me! Mmmmmmmmmmmmmmmm"

As Steve fell exhausted back against the shelving, Gemmy hefted one of her large titties and ran her tongue along it, to suck up the heavenly scum. She used her fingers to scrape more off of her face and into her mouth. Finally she retrieved her gum from under the shelf, rolled it around in a pool of cum that had coalesced on her other tit and then popped the gum into her mouth. The flavour would last for several hours, until she could get a new injection from Danny or one of his boys.

Steve did up his pants, made half hearted "love you baby" noises and departed.

Gemmy turned her wrist to look at the time, but of course her oversized watch was never on her slim wrist anymore. It was in her desk drawer. She snuck a look outside the supply room door and saw that she had just fifteen minutes.

Steve had ruined her bra, so she quickly did up her blouse. As she left the room and strode to the ladies' washroom, her breasts bounced. Agnes was returning from the photocopy room. Gemmy gave her a slight smile and wave, noticed a bit of cum dangling from her fingers and quickly sucked it off. Agnes gave a snort of disgust and walked back to her own desk.

In the washroom, Gemmy took her time cleaning the rest of the cum off of her face and from the front of her hair. She took her brush out of her purse and fussed with her hair. Her hair had been dyed an even more striking shade of red than her natural fiery colour, and was permed into a big poof ball. It was SO hard to keep looking good, but Danny love her hair that way. It was also a big hit with the punters at the strip club where she worked for Danny in the evenings where she was the star of the show... well, she, and her hair, and her little bit extra. It was the bit extra that drove the customers wild and if she did say so herself, it was more than just a bit extra!

When she had her face and hair repaired, and her blouse was back in order, Gemmy took out a small vial of white powder and carefully spilled the contents on the counter. She then snorted it up. There... now she felt SO much better. She then pulled up her micro skirt and removed her panties. As always they were slick with her own juices, so she did not put them in her purse, but rather dropped them in the trash. She then took a tube of lubricant out of her purse and using two fingers, she pushed several generous dollops up into her ass.

After cleaning her hands, she made sure that the camera in her purse was turned on and was situated so that it would film properly through the pin prick hole in her purse, just as Danny had told her to do, and then she went back to her desk.

Ever since she had become Danny's girlfriend almost six months ago, Gemmy had wanted to do nothing but be with him all the time - whether it be at his office during the daytime, where he ran his numbers, prostitution, drugs and loan sharking businesses... or at night when she was the lead dancer at the strip club. But Danny insisted that he wanted her to keep her job here at the Daily Planet, and she guessed the camera had something to do with that.

Gemmy returned to her desk where she popped out the cum flavoured gum and stuck it to the underside of her desk. She had just lit up a cigarette, when the cry came from Perry White's office.... "Olsen, get in here!"

Agnes harrumphed as Gemmy hurried past her and closed Mr. White's office door. Gemmy placed her purse on a credenza where the camera was sure to get a good shot of all of the action and then went to the front of Perry's desk and leant over it.

As he did every Thursday at 2:15 pm, Perry got up from behind his desk, walked behind the big titted bimbo and lifted up her skirt to expose her naked ass. Having already removed his trousers and y-fronts, Perry's cock swung free and with very little effort he pushed his cock deep into Gemmy's well lubed anal passage.

Gemmy purred and puffed on her ciggy. "Fuck me Perry," she cried. "Ram me hard!" She loved having a big strong cock shoved up her ass almost as much as she liked eating cum. As Perry pounded her ass, her own dick was free from her skirt and was squished between her body and the hard surface of the desk.

Perry loved the feel of Gemmy's tight ass as it gripped his dick. It was wrong... he knew it was wrong, but this girl underneath him was so damn sexy. She made him forget about his heartache for his beloved Alice.

When his loving wife Alice had died a year ago, he had thought his sex life was over. Then six months ago, Lois Lane had walked into the office and introduced everyone to Gemini Olsen, the twin sister of Jimmy Olsen, whom Olsen had never previously mentioned. Perry knew that Jimmy had crossdressed on several other ocassions and always felt that Jimmy might be a bit gay at heart, but while there was a family resemblance, Perry could see the rounded hips and small breasts under the smart business suit. There was no way that Gemmy was Jimmy in drag!

And yet... here he was, fucking Olsen's "twin sister" up her poop chute, knowing that in fact that WAS Jimmy.... because if he was to turn her over, he knew she had a thick throbbing cock of her own, rather than a cock draining pussy.

Lois had told Perry that Jimmy had gone deep undercover after a story and convinced Perry to let Gemmy take Jimmy's place until he returned. At first, Gemmy had been a fine replacement. But two weeks later, Lois had not returned from covering a story on lesbian biker gangs. Soon after, there were noticeable differences in Gemmy. She began dressing less formally and more sexy. One day she came in with her breasts considerably larger and her lips were collagen enhanced. She started smoking and soon started sneaking off to the supply room with male employees.

Her work had suffered. She no longer went out chasing stories. In fact, she now seemed too dim witted to even string words into a complete sentence.

He had called her into his office to fire her, regardless of how highly Lois had recommended her, and regardless of her being Olsen's sister. But within two minutes she had been on her knees with his cock in her mouth. God she was sexy and he missed sex with Alice SO much.

And he saw what he had always suspected. As she knelt at his feet, he could see that her skirt was tented by a large dick, erect under her own panties. This gal in front of him..... somehow she was a man. And when he looked closer, she had a pink ribbon tied around the base of her cock - a ribbon that was fastened with a minature plaid bow tie! She WAS Jimmy Olsen. But that did not deter him. She had him fired up and he lifted her to her feet, spun her around, raised her skirt and sank his cock deep into her nether passage.

Gemmy had squealed in delight. She had never shown her cock to any of the men at the Planet, but she knew that it was okay if Perry knew she was different from other girls. As he came deep inside her ass, she had spurted her own pretty boy cream all over his desk.

With Lois Lane and Clark Kent missing, Perry had no one to help him sort out Jimmy/Gemmy's dilemma. So, Gemmy remained on the payroll as Perry's second secretary. Once per week, Gemmy had drained Perry's balls. Sometimes he came in her ass, but sometimes she liked him to pull out just as he was about to cum, so that she could suck the sperm from his rod, while she looked into his eyes.

Today, she had Perry pull back and she flipped over on the desk. She wrapped her legs around Perry's back as he frantically thrust back and forth in her ass. She kissed him hungrily on the lips.

'Fuck me chief!'she screamed.

She made sure that her pretty cock was visible to the camera as Perry withdrew and sprayed his seed all over her cock, and balls and ass. He collapsed on top of her, exhausted. As his cock slipped from her ass, he kissed her gently on the cheek and whispered in her ear, 'I know you are in there somewhere Jimmy. Don't call me chief!

As she returned to her desk, cum was running down one leg. She popped her cum soaked gum back in her mouth and lit a ciggy. She opened an issue of Cosmo, pretending to read it for the next five minutes as she waited for Guido to come pick her up and take her back to the apartment she now shared with Danny. Little Danny McGraw they called him, but there was nothing little in his pants. They only called him "little" because his brother was "Big" Monte McGraw.

Gemmy loved Danny, but she knew that once Monte was out of prison, he would take back the rackets that Danny was running for him. She hoped that Monte would like her enough to want her to be his girl too.

Gemmy flicked a bit of tobacco off her tongue. She wondered whatever had become of her brother Jimmy. Everyone said he was a great reporter and rumour was that he was working deep undercover. She wondered if he would ever be seen again.

Next, If we continue... Chapter 1.. How Supergirl got her revenge on Jimmy

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
AnonymousAnonymousover 12 years ago
Wow

Incredibly hot story, please keep continuing this series.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
Fucked Ch. 01: The Interview Twink interviews a Trans Adult model, but she takes control.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
Family Issues Ch. 01 A futa girl forces an innocent young man to share her bed.in Transgender & Crossdressers
Dickgirl Conquest Joe, unhappy with his girlfriend, meets a hot dickgirl.in Transgender & Crossdressers
More Stories