Jimmy Olsen Shemale Bimbo Ch. 09-11

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Jimmy Olsen - Shemale Bimbo

by Mistress Tawny Suede

Recap of the story so far...

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

In a past adventure, Jimmy had gone undercover as "Julie Ogden" a chorus girl in order to catch local gang boss, "Big" Monte McGraw. Now Monte 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.

When sources told him that Danny was interviewing for a new secretary, Jimmy decked himself out in his best female disguise, figuring he was a cinch to get the job, which would let him investigate undercover once again. But he fled when he saw all of the other attractive women who were waiting to be interviewed.

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.

When Jimmy showed up at Danny McGraw's office as Gemini ("call me Gemmy") he easily got the job. What Jimmy did not know was that he had been lured into the job, and despite his feminine body, the crooks had recognized him because he still wore his Superman signal watch!

Monte McGraw wanted revenge on the young reporter. He didn't want him killed - that might get Monte a life sentence. Instead he wanted Jimmy humiliated, fired from his job and penniless. As part of the plan, on Monte's instructions, Danny had contacted an outfit called "The Apocalypse" and obtained some special gum and cigarettes which Danny then insisted he chew and smoke regularly, so Gemmy had the right appearance as his secretary/receptionist.

Of course, Jimmy had no idea that the gum was spiked with super fast female hormones designed to increase his bust size, increase his libido and make it hard to get an erection. And the cigarettes contained toxins that killed brain cells. Every time he smoked one he got just a tiny bit dumber! And those brain cells wouldn't grow back!

Over the next couple of weeks Jimmy juggled his job as Danny's secretary with his responsibilities at the Daily Planet. Soon Danny finally had Gemmy sucking his cock daily. Jimmy discovered he really liked the taste of cock and cum and began searching out more dick!

Chapter 9 - Transforming

Sunday morning Jimmy woke late and lounged in bed. He had a mid afternoon appointment at a hair and nail salon. When dressing he chose a shorter skirt and higher heels to show off his legs. He chose a cute blouse but was frustrated when he tried to put on a bra and none would fit him. They were all too tight! So he put on the blouse without a bra. He popped some gum in his mouth and admired his sexy curves in the mirror. His nipples engorged and tried to poke through the blouse. He felt a thrill run through his groin but was surprised to find his dick not getting hard in his panties.

He left a bit early for his appointment, stopping off at a lingerie shop to buy some new bras. When the salesgirl measured him he discovered he was a full cup size larger than when he had stepped out of the transmogrification machine. How had that happen he wondered? Had he been eating too much? But before he could give it much thought, his attention was diverted by a lovely negligee which he absolutely HAD to have!

He smoked two cigarettes as he walked to the beauty salon. There were a couple of younger assistants working that day. They convinced him to have nail extensions permanently applied and then painted both his finger nails and toe nails a lovely shade of red. As to his hair, he knew that Little Danny liked him to look a bit slutty and bimbo-y, so he had them give him a frizzy perm.

During their conversation he said that he could use a bit of a trim down below too but was reluctant to remove his panties. He finally revealed to the girls his little secret. They blushed along with him, but that did not stop them from giving him a brazilian wax. When Gemmy walked out of the salon, she couldn't help squirming because her entire groin region was now hair free!

Jimmy... Gemmy.. It was all getting a bit confusing for him. He was having so much fun in this new body! He was eager to get the goods on Danny, but he was also enjoying himself so much. He did not know why but his whole sexuality was ramped up! He loved having tits. He loved wearing stockings and high heels! And yes, he loved sucking cocks! Why had he not done all of this so much sooner. He had occasionally crossdressed, and then hidden from view! Now that he was more open, more adventuresome, life was such a rush!

Since he was in the neighbourhood, he decided to go up to the Daily Planet offices and catch up on some typing. It was actually stuff he had already typed, but Perry White had sent it back because of all the typos and grammar errors! If Gemmy didn't do better, she might lose Jimmy's job!

Lois was not in the office. But as Jimmy tried to work he noticed the looks he was getting from the few co-workers who were in the office. Perhaps Lois had told them that Gemmy was actually Jimmy. And he worried about that. Not because he didn't want to be discovered, but because they might expect him to do all the Jimmy work that should be done, and he... he just wasn't feeling like he could quite do that.

Of course it could just be that they liked looking at his pretty face, his nicely permed hair and his bright long fingernails. Of course those fingernails made it much harder for him to retype the notes he was trying to work on. Well, tomorrow maybe, after he was done at Danny's place.

He picked up his purse and his shopping bags. As the elevator dinged to take him down and the door opened a tall broad shouldered handsome man stormed out of the elevator and knocked Jimmy's bags down, spilling the contents. He got to his knees to pick them up, as did the man.

"I'm so sorry!" he said.

"It's alright," said Jimmy. "I'm such a klutz these days!"

"These are very nice!" said the man handing some bras to Jimmy. As he straightened up he looked at Jimmy's cleavage and then at his face. "I'm Steve Lombard. I work upstairs for WGBS. I haven't seen you before. Say... I know.., you must be..."

"I'm Gemmy Olsen. Jimmy's sister. I'm filling in for him while he is away helping a friend!" she smiled at the sportscaster. My, he was good looking! And she was craving something.

But Steve was having similar thoughts. He was well known to hit on just about any woman. "Listen, I really am sorry for knocking you over. Could I buy you a drink?"

"Oh, I'm sorry.. Steve, was it? I have to be somewhere else in a half hour!" He didn't really but he was hungry NOW! "But I could spare, say, five minutes."

"Five minutes?" questioned Steve.

"Oh, I think five minutes is all that I will need!" said Jimmy, closing the gap between them, kissing Steve lightly and cupping his groin!

"Five minutes! Oh right.... fffff five minutes!" repeated Steve as Jimmy took him to a supply closet just down the hall. As soon as the door closed, Jimmy was on his knees and working on the man's belt. Steve took belt in hand and undid it and the top clasp of his jeans. Jimmy looked up and stared into Steve's eyes and he drew down the zipper, pulled the pants part way down and then the underwear.

Steve's lovely cock bobbed free for an instant before Jimmy grasped it in his hand, fondled it briefly to get it to start rising and then engulfed it in his mouth. The strong taste of a man made him quiver. Oh how he loved that flavour, and the spongy texture of a cock. And the precum, oh he loved precum. "You have a lovely cock, Steve!"

"And,,, and,,, you have a lovely... pair of shoes!" said the jock, his mind able to focus on only one thing - the intense pleasure he was feeling from his penis! "Oh god, woman, you fucking know how to suck a cock!!!"

Jimmy paused and smiled up at him. "I love a big dick!" he said.

Steve tried to push him back and lift him. But Jimmy stayed on his knees, sucking and swallowing the prejism.

"God baby, let me fuck you! If your mouth is that amazing, you've got to be a fantastic fuck!" he said.

Jimmy paused, briefly. "Mr. Lombard, how dare you! I'm not THAT type of girl!

"I'm THIS type of girl!" she grinned and then fisted his dick a few times before sucking again. When she felt his legs quaking and knew he was about to cum, she pulled off of the cock. Using both hands she milked his cock. She held it just an inch from her mouth, and said, "Give it to me Steve. Give me your cum. Jizz in my mouth! Come on baby, come for momma! I want your fucking cum!"

And he did cum. Jimmy wrapped his lips around the spurting cock and took the blasts in his mouth! He swallowed and swallowed.

He loved the taste of cum! He loved the sliminess of it. He loved the feel of it on his tongue. He loved it! He loved it! He loved it!

When Steve was dry, Jimmy stood and kissed him on the lips. "I'll see you around, tiger!"

With a nice load in his belly, and cum flavour in his mouth, Jimmy headed home!

Chapter 10 - Further Descent

Next morning as Jimmy walked from the subway to Danny's office, he was delighted by all of the wolf whistles from the construction workers, and by how many cars almost had accidents as their male drivers ogled him. He was wearing one of his larger bras, but his top was designed to show off his significantly larger cleavage. He was wearing his highest heels, his sheerest stockings and his shortest skirt. His red hair was now permed and frizzy and his large hoop earrings bobbed as he strutted. His makeup was perfect and his bright red lipstick highlighted his gorgeous face.

He was a guy, but he loved being a girl! He still couldn't believe he had not strutted his stuff like this years ago!

Just before entering the offices he spat out the gum that he had been chewing and lit one of the special cigarettes so that Danny could see he was smoking them!

The phone rang as he entered and he answered it. He easily slipped into his receptionist routine. He nodded at Guido and blew a kiss at Danny as they entered. Fifteen minutes later Guido came out of Danny's office and told Gemmy that the boss wanted to see her. As she entered the office Guido patted her bottom and then closed the office door.

Danny was standing. As he turned towards his gorgeous receptionist, it was hard to believe that there was a guy under all of that makeup and tits! And that was good because Danny's brother, "Big" Monte McGraw expected Danny to help continue feminizing and ultimately humiliating the reporter.

Gemmy hurried towards her boss and then flung herself into his arms. "Oh, baby!" she said. "I missed you so much over the weekend!" Her lips met his and she hungrily kissed the mobster. Her hand pawed at his groin and she tried to get her hands in his pants and around his stiff cock.

"Easy babe, easy" Danny said gruffly. "I missed you too!" He mauled her big tits as he eagerly kissed her back. Danny sat on his office couch and Gemmy sat on his lap, facing him and grinding her ass on his hard cock.

Danny almost tore her dress open as he released her tits from her bra. He pulled her forward and eagerly sucked on one fat nipple, and then the other. Gemmy shivered in ecstatic joy. She rubbed her hand against the gangster's hard cock!

"Oh, baby," she panted. "I need your cock. I just gotta suck your cock!" She sank to her knees between his legs. Danny scooted his trousers down and Gemmy forcefully yanked his underwear down to his knees. Gemmy then dived in and eagerly took Danny's cock all the way down her throat. Oh, this is absolute fucking heaven, she thought!!

Danny no longer cared that Gemmy was really a guy in disguise. He was in lust with her. She was the best cocksucker he'd ever come across. "Oh baby," said Gemmy, looking into his eyes as she licked along the length of his cock, "You gotta fuck me baby! I really need a good fuck!"

Jimmy had never had a cock in his ass. But he had been using his large dildo every night to edge himself and then shoved it deep in his ass and had cum strongly each time. He wanted... he NEEDED the real thing!

"Keep sucking me, babe! Oh fuck, you've got such a talented mouth!" moaned Danny. Gemmy resumed bouncing her head up and down on his cock. Her hoop earrings bounced as she gleefully gobbled her lover's dick! "Soon, baby, soon! I'm gonne fuck your pussy so hard! But not quite yet. But soooooooooooooon!" Danny's last word was distorted as he shot his load into the reporter's hungry mouth. "Oh that is SO fucking good!" her cried.

Gemmy grinned and wiped some cum from her chin, licking it off of her fingers. "You ever been ass fucked before babe?" asked Danny.

"Mmmmm, I love the idea Danny. But no, not yet. But I SO want it!"

"And I want to fuck you babe!" said Danny, pulling her close for a kiss. "But not quite yet. Soon. But you gotta promise me, you ain't gonna fuck no one else before me, right!"

"Sure thing baby!" She waggled her fingers as a goodbye as she left the office and returned to her desk. As she passed Guido, she grabbed his crotch briefly and whispered "Can't wait!" to him.

Guido shut the door. Danny was just straightening his pants. Danny said, "Next time Monte calls from prison, we tell him everything is ready for us to visit. God, we gotta do that soon. I really want to fuck that tramp!"

Guido was surprised, "Even though he's a guy?"

Danny lit a cigar. "Fer Christ sake, Guido! That mighta been a guy once, but that dame is all gal now! I've got no idea if she has a pussy, or a cock. But if I can't fuck her pussy, I know I'm going to tap her ass! Fuck, even if she does have a pussy, I'm still going to shove it up her ass at some point! We are supposed to embarrass the prick, ain't we?

"You make a good point, boss!"

About an hour later, Guido was alone with Gemmy in a supply closet. He undid her blouse and opened her bra. Her sumptuous tits popped out and he mauled them in his big ham hands. Gemmy moaned as he tweaked her nipples but then he went to kiss her, she slapped his face.

"Danny says I have to suck you off, but there was nothing about having to kiss you!" she laughed at him as she got to her knees. She was now expert at getting his pants and underwear down and she happily gobbled up his cock. Guido leaned back against a file cabinet. He went to grab the dame's head, to guide her blowjob, but as soon as he touched her, she bit down on his cock and let out a surprised yelp!

"Watch the hair, Guido!" she snapped.

"Okay, okay!" he replied

As he sucked, Jimmy's mind was in a swirl. Over the last few weeks he had become so turned on by having the shape of a woman and dressing sexy titillated him even further. It had not taken much persuasion to get him to suck his first cock (well, his second). And now he found the feel and taste of a cock in his mouth, the flavour of cum in his mouth, and the smooth texture of jism sliding down his throat... god, they were so irresistible.

And he had been fucking his ass with a dildo every night while jerking his own cock to shattering cummies.

He giggled, startling Guido a bit, as he thought about how much he now craved having his ass fucked. He needed to feel a real cock, attached to a real man, sliding in and out of his ass.

He wanted a hard fucking, but he wanted that from Danny. Much as he wanted to just stand up, turn around, and have Guido slide his cock up his butt!"

Jimmy went back to his desk. His mind drifted to outfits he had seen in the stores, and he read a fashion magazine for awhile. He filed one of his nails that had been damaged. He had some typing to do, but he was having trouble concentrating on the typewriter, so he just pushed that aside.

Shortly, Danny and Guido left for lunch, leaving him alone in the office. After they returned, Danny called Jimmy into his office and Jimmy sucked him off again. Danny then told Gemmy that he was planning to change her job around. She didn't seem to be enjoying her work in the office and so he had other plans for her. "Whatever you want, honey!" she replied.

As usual he sent her home early. Jimmy lit a cigarette as he left the office. He strutted along on his heels again revelling in the wolf whistles and cat calls. In a moment of clarity he wondered what all those men would think if he pulled up his skirt and they could see the outline of his hard cock in his skimpy panties. And then he realized that his cock was not hard. And it had not been hard all day. Yet he still had an erotic shiver from all the attention.

And in that moment of clarity, he also realized that he had been all alone in Danny's offices for ninety minutes and had not even thought to look for the incriminating records that would be in those filing cabinets. Oh, what a lame brained silly goof he was. What a dizzy bimbo he was!

Chapter 11 - Don't Call me Chief!

As he usually did after leaving Danny's office, Jimmy took the subway over to the Daily Planet offices. He hadn't brought any conservative clothing with him, but he didn't care. He liked dressing as Gemmy. He adored the high heels, stockings, short skirts and skimpy blouses. He loved how they made his body look so sexy. He loved the way they made him feel sexy. Was he a guy, or was he a gal? He didn't really care. He loved being Gemmy. He loved being a sexual tease. And if the staff at the Planet could not accept that, well, screw them!

It was mid-afternoon and so the newsroom at the Daily Planet was packed with people. Jimmy did attract a lot of attention as he strolled to his desk. He did not see Lois anywhere in the office. Nor was Agnes Frump at her secretary desk outside Perry White's office. Jimmy put his purse in his desk drawer and started to organize papers on his desk. His in-tray was full of pieces written by other reporters which he was supposed to proof-read and correct.

He picked up one or two and scanned them. But his eyes did not want to focus on the text. Or perhaps it was his brain. For some reason he could not concentrate very long on any of the text. Instead he reached into his desk and pulled out a popular gossip magazine and began reading it. Of course he had popped some gum into his mouth beforehand and, despite the No Smoking signs on the walls, he lit up one of his special cigarettes from Danny! Hmmm... Danny! That got him thinking about the gangster's nice thick co...

"Olsen! Get in here!" came the cry across the newsroom floor! Perry White was standing outside of his office yelling at Jimmy!

Thoughts of cocks would have to wait. "Coming Chief!" he called out.