Jimmy Olsen Shemale Bimbo Ch. 06-08

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Jimmy Olsen - Shemale Bimbo

by Mistress Tawny Suede

Chapter 6 - Going Down!

When Jimmy woke the next morning he sat up and stretched. He loved the feel of his silk nightie as it slid across his body. He shivered as a breeze from the air conditioning stiffened his nipples! He walked out to the stand by the front door and opened his purse. He first popped a piece of the gum in his mouth and then he lit one of the cigarettes from Danny and inhaled deeply. Mmmmm that felt so good!

He took a quick shower, being extra careful to be sure his bumhole was clean of any lubricant residue from the previous night. He then applied his makeup a bit more tarty than the previous day, in particular with a bolder lipstick since Danny had commented that he was looking a bit pale. He put on a tube top that left his shoulders uncovered and his navel exposed. It didn't show off his tits as much but he figured that the extra skin showing would make up for that. He also took time to paint his fingernails and toenails to match the shade of the lipstick. And finally, now that he'd has his ears pierced, he put on some big hoop earrings. He shook his head a bit and giggled.

And popped another piece of gum in his mouth.

When he arrived at work, Guido opened the door for him and complimented him on his looks. Jimmy fluttered his eyes at the goon, and smacked his gum so Guido knew he was chewing.

During the morning Danny found many reasons to lean over him and lightly touch Jimmy on the shoulder or the arm. Each time his hand rested a little bit longer. Just before noon, Danny nodded at Guido and then returned to his office. Guido surreptitiously locked the main office door, just in case.

Jimmy got up from his desk and picked up the folder of papers he had just finished typing for Danny and click clacked on his high heels into Danny's office. He placed them on the desk and told Danny that he was going to go out to run an errand and pick up some lunch. He had not noticed that Guido had closed Danny's office door with himself outside.

"Gemmy," said Danny as he stood up. "You're a very attractive girl!"

Jimmy blushed and said "Thank you!"

Danny approached and took Jimmy's hand. "You remember when I hired you I said that there were other duties?"

Jimmy was feeling a bit uncomfortable. "Yes, do you want me to run an errand for you while I'm out?"

"Lunch can wait a bit, babe." said Danny. He then pulled Jimmy close and kissed him hard. Jimmy tried to push the gangster away, but in his newly reshaped body he had no strength to do so. Danny kissed him again.

"C'mon, Gemmy. You know what I expect from a pretty gal like you!"

Jimmy did know, and he had thought about this. He knew that if he wanted to get the scoop on Little Danny, Big Monte and the entire gang, there were things which he might have to do, no matter how repulsive they might be. But... were they so repulsive, he wondered?

"Sure Danny, sure!" said Jimmy. "You just startled me a bit, being so abrupt and everything!"

"That's the girl!" said Danny, leaning in to kiss Gemmy again. This time Jimmy stayed calm and kissed back tentatively. Danny pressed harder Jimmy resisted. Then Danny brought his hand up and pulled down Jimmy's top and then clasped one of Jimmy's breasts in his hand.

Jimmy groaned at the exquisite sensation of having his tit played with and Danny forced his tongue into Jimmy's mouth. Jimmy moaned again and now he sucked on Danny's tongue, letting the forceful gangster ravage his mouth!

"Oh god, yes! Play with my tits!" cried Jimmy. Danny was glad to oblige. He sucked one of Gemmy's nipples into his mouth and teased it with his tongue. Jimmy had toyed with his own new nipples over the last few nights but it had felt nothing like this! "Harder!" said Jimmy. "Suck me harder!"

"You got it babe!" said Danny as he mauled Jimmy's tits, switching back and forth from one to the other. Jimmy pulled Danny's head hard against his breasts. Danny needed his own pleasure and he took one of Jimmy's hands and pressed it to his groin.

"Squeeze me, babe! Play with my dick!" he told Gemmy.

Jimmy did squeeze. He was lost in a horny bliss! He had always wondered what another man's cock might feel like in his hands. He squeezed the hard shaft through Danny's pants.

Danny sat back on his chair, quickly undid his shoes and then threw his pants to the side. Jimmy stood there marvelling at the tenting in Danny's shorts. "You did this to me babe. All your teasing and looking so sexy for the past couple of days. Now get down here and take care of this for me!" Danny pulled on Gemmy's arm and she sank to her knees.

Jimmy knew what Danny wanted from him. He reached up and tugged Danny's shorts down. His cock stood up proudly, precum glistening on the tip. This was it, thought Jimmy. I'm going to have to do this.

He'd always wondered if this was what he wanted. Did his crossdressing mean that he was gay? Did it mean that he wanted to feel the touch of a man. Did he want to have sex with a man?

His crossdressing had started out so innocently. Just to fool other people, or to prove a point at the office, or to get a story. He had been amazed that he could transform himself into a woman good enough to fool other people and sometimes his closest friends. And that had led him to experiment further, to go out to a club occasionally dressed enfemme. But it had never been sexual, had it?

Well now he was at a point where he had no choice. He was not sure that he wanted to make a choice. Circumstances had led him to this moment. Of course, he had more or less directed those circumstances, but... well. Now there was no choice.

"What do you want me to do Danny?

"You know what I want babe! Just do it!

Jimmy reached out and grasped Danny's cock. He had touched one other cock in his life - that of Danny's brother Big Monte. It was necessary in order to entrap the crook. Afterwards they had both told a similar story, that Monte had kissed a monkey that Jimmy was holding. What a load of hocum! But somehow people had believed it. No one knew that to catch the crook, Jimmy had led him on as a woman, and then has sucked his cock once, in order to gain the information he needed. And here he was again.

But this time was different. As Jimmy stroked Danny's cock, he felt an eager desire flow through him. He wanted this cock. He needed this cock. Whatever had gotten into him, it felt so very right!

"Tell me sweetie!" said Jimmy, looking up into Danny's eyes. "Tell me what you want and I'll do it. I'll do anything for you Danny!"

"Suck me, Gemmy. Oh babe, suck my cock for me!"

And Jimmy did. He opened his mouth and took Danny's rod into his mouth. He sucked on that cock. He bobbed his head up and down. He licked the shaft. He tickled the glans with his tongue. It lasted ten minutes and when Danny came, he held Gemmy's face down on his cock and shot his load into her mouth.

"Swallow it babe! Swallow all of it!"

And Jimmy did. He swallowed every drop and when Danny was done shooting, Jimmy spent another minute teasing the piss slit with his tongue making sure he had gotten every drop.

Danny collapsed back into his chair.

"Go fix your face, babe" he told Jimmy. Jimmy hurried to the bathroom and fixed his lipstick. He smiled at himself in the mirror. He knew that Danny would now trust him more!

And, he had actually enjoyed sucking off the gangster. That really wasn't so bad, he thought!

Chapter 7 - Discovered by Lois

Danny never made Gemmy work the full day. By two pm they were finished and he sent Gemmy away, after giving her ass a good fondle of course. Once Gemmy left, Guido asked Danny, "So how was it?"

"She... he.... gee I don't know what to call him. But it was great. A bit sloppy, but he gave a good blow job and swallowed! And he'll get better the more he does it!"

"So it wasn't so bad being blown by a guy?"

"If the guy looks that sexy, it ain't going to be hard. Well, my cock will be hard! Hah!"

"I don't know if I could..." started Guido, but Danny cut him off.

"This is what Big Monte wants. So we do it, understand? And he's been smoking and chewing his gum regularly, right?" queried Danny.

"Sure thing boss. I don't even have to remind him. Heck that gum smells so good I might even try a piece myself!"

"Not such a good idea, you big dope. You know what that stuff is supposed to do!"

"Actually, I forget which is which!" said a puzzled Guido.

"The gum has got super powerful hormones in it," said Danny. "Or so the guys from The Apocalypse said. With every piece he chews, his boobs are going to get a bit bigger. The stuff is addictive too, so the more he chews the more he's going to want. Monte decided that if the guy wants to dress up as a girl, he'd give him boobs to shame him. But Christ, when he walked in here he already had a rack on his chest! What's with that, eh? Anyway the gum chewing should make them even bigger! At the same time, it's going to start making his dick go limp! It may increase his libido too - you know make him hornier, but unable to get it up! Hah!

"And the cigarettes. They contain something that is supposed to kill brain cells." said Danny, tapping a finger at the side of his head. "So every time he smokes one he gets just a tiny bit dumber! The longer we keep him around here, and the more he smokes the cigarettes we give him, the stupider he is going to get. And those brain cells ain't going to grow back, it's permanent!

"Keep him here long enough and he won't be able to keep a job or figure out how to pay his bills. He'll be out on the street, homeless and a bum!"

"Boy, Monte really hates this guts, don't he!" laughed Guido.

"Olsen put him in jail. Monte wants to destroy the creep. He doesn't want him killed - no way he's doing that much time if he gets caught! But he does want him humiliated, broke and destitute!"

When Jimmy left the office, he strutted down the street, now very comfortable in his heels. He had done it. He had actually sucked Danny off and thereby gained his trust a bit more! He giggled to himself as he lit another cigarette. He also wiggled his bra a bit. It must have shrunk in the wash!

He took a cab to the Daily Planet and put in several hours of work. Before entering the offices, he redid his makeup in the washroom and changed his top for something a bit more dignified, but Agnes Frump still scolded him on his appearance. When he had to go into Perry White's office to update the chief on the various stories that he was working on on behalf of his "brother", he caught Perry giving his ass an appraising eye and was sure to shake it for him.

When he was ready to leave the office he ran into Lois Lane who had been away for the past ten days. He introduced himself to her as Gemmy, Jimmy's sister. After a few moments pause, Lois grabbed his arm and steered him out of the office. They went to a bar down the street, and took a table in the back corner. They both ordered drinks. Jimmy lit a cigarette, to Lois's annoyance.

"Okay, Jimmy. Spill it. What crazy scheme are you up to now? What have you done to yourself?" asked Lois.

"I'm not Jimmy! I'm Gemmy, honest! Does THIS look like a Jimmy?" asked Jimmy as he opened his blouse to show his naked tits to Lois!"

"Close that up!" exclaimed Lois. "I know Jimmy doesn't have a sister. You ARE Jimmy. You found a reason to dress up as a woman again, didn't you?"

Jimmy sighed. He stubbed out his cigarette and then unwrapped a piece of gum and started to chew that. He told Lois about his plan to get the goods on Big Monte's gang once and for all, and how it meant he had to go undercover at Little Danny's office, as a woman.

Lois sighed. "You know this isn't going to end well, don't you? Superman is off planet with the Justice League for at least another month and that watch..." she pointed at the signal watch that the feminized reporter was wearing.. "that watch won't do you any good!"

"So Supergirl used the Kryptonian transmogrifier on you? Well, it did a nice job, I have to say. You do look cute. But Supergirl hasn't been seen in several days either. She may not be able to help you out if you get in trouble!"

"There's not going to be any trouble, Lois. Honest! I just need to find the right files and I'll get Supergirl to change me back!"

"Be careful Jimmy! When I used the machine Superman told me that it stored my original body pattern but if my altered form got changed too much then the machine might not change me back!

"Not a problem Lois. Another day, maybe two and I will have all the proof I need!" Jimmy removed a compact from his purse and tidied up his lipstick. Lois shook her head. This would not end well!

Jimmy grabbed a quick bite to eat. Back at his apartment it was still early, but Jimmy hopped into the shower and then once again climbed into bed oiling up his asshole and replayed the events of the day in his mind as he slid his favourite dildo in and out of his ass.

He had actually done it. He had given Danny a blow job - and he had enjoyed it!

The next few days were a repeat of that day. He worked during the morning then Danny called him into his office and he sank to his knees giving the gangster a delightful blow job. Sometimes Danny finished in his mouth and sometimes he liked to shoot on Gemmy's face!

On Thursday, he told Gemmy that Guido had been doing good work and as a reward he wanted Gemmy to blow Guido as well. Gemmy said she was reluctant. Danny reached into his desk and pulled out two one hundred dollar bills and stuffed them into Gemmy's blouse, feeling up her tits as well. He then patted her on the rump.

Jimmy went back to his desk. A couple minutes later Guido walked up to her and dropped his pants. There was no thought of a kiss or any pretense about affection. Jimmy took Guido's dick into his mouth and bobbed up and down. This was now the third dick she had sucked. It was thicker than Danny's but much shorter. Guido did not last long and came in his mouth. Jimmy swallowed. When Guido withdrew, a thin line of jism landed on his chin.

When Guido noticed, he pointed at his chin. Jimmy scooped up the jizz with his finger then looked Guido directly in the eye as he seductively licked his finger clean.

On Friday Jimmy again blew both men, though there was no extra cash this time. A new routine seemed to be in place.

Chapter 8 - Saturday Night Fever!

On Saturday Jimmy put in a full day of work at the Daily Planet, as Gemmy. Though he was starting to have some trouble concentrating on that work. He just couldn't quite fit the pieces together like he usually did, and he started making some spelling mistakes while typing, though he only found out about that when someone else proofread for him. He was sure he had spelled everything correctly!

Lois was there as well and they went to lunch together. But things were different, Lois noticed. Usually when she lunched with Jimmy he was always trying to chat up the young girls at the other tables. Today, Gemmy's eyes seemed to follow the handsome men from table to table.

"Are you feeling alright?" asked Lois.

"Yes, I'm fine! No problem!" replied Jimmy as he lit yet another cigarette! He couldn't tell Lois how incredibly horny he was feeling. Since he was not working with Danny today, he would not be sucking off Danny and Guido. No thrill from that! But he had to find some release!

Back at the Daily Planet building he went into one of the stalls in the women's washroom and jerked himself off! That felt better, but it did not really get rid of his craving for cock! He never would have believed that in less than a week he had gone from having sucked only one cock in his life, to now almost craving the feel of a cock in his mouth!

He left the Planet offices earlier than planned and went home. He stripped down to his bra stockings and heels, lit a cigarette and toyed himself with his dildo. Oh that felt so good!

But he needed more!

He took a nap, waking at eight pm. He dressed slutty and at eleven he headed out of his building and caught a cab. He knew what he wanted, what he needed. He did not head to a regular bar, but instead had the cabby take him him to one of the tranny bars that he had frequented in the past when he timidly went out dressed.

He wanted the safety of mixing with people who knew what he was - a man dressed as a woman, even though he had the full curves and delicate face of a woman, he still had a cock, and he did not want any negative reactions tonight!

At the bar he was admitted for free. The gurls all got in free. The guys and curious genetic gals paid admission. The gurls got in free because they attracted the paying punters. Jimmy sat at the bar, his stockinged legs dangling, his blouse open far enough to reveal his real tits. He picked up his wine glass and admired his nails. For tonight, he had taken the time to apply long fake nails and had filed them and painted them a blood red. Just looking at them and the lipstick on his wine glass sent a shiver of delight down his spine!

As he sat at the bar, he chatted with other gurls like him, and the occasional man who tried to hit on him. He knew what he wanted, but he still had to work up his nerve!

When Jason stood beside him, to order a beer, they made brief eye contact and he said hello. There was nothing special about him, but something stirred in Jimmy's loins.

"I'm Gemmy," Jimmy offered. "I don't come here very often, if that was going to be your first question!"

Jason smiled. "No I never open with that one. Gemmy? That's an unusual name."

"It's short for Gemini. I picked it myself."

"Ah!" said Jason. "It speaks to your dual nature. An appropriate name for an attractive... lady!"

Jimmy knew that Jason was the man she had been waiting for. They made idle chit chat for five more minutes, flirting with each other. Their hands touched lightly on the bar, and his other hand stroked Jimmy's side as they slowly moved closer to each other. Eventually Jimmy reached down and squeezed Jason's very evident hardon. He leaned in and whispered in Jason's ear, "I want to blow you!" Then he gave Jason a light kiss on the lips.

Jimmy knew that there was a service door at the back of the bar which led to an alley. That door was not locked. Patrons could go outside for a cigarette or whatever reason, then slip back in. He had once followed a couple out that door and seen the gal fall to her knees and unzip the pants of the man, while further down the alley a couple had been fucking. Jimmy led Jason by the hand through the dancing crowd and out to the alley. No one else was there right now, but there was evidence it had been used recently.

Jimmy led Jason down the alley to where it was a bit darker and there was some abandoned cardboard on the pavement. Jimmy pushed Jason against the wall and kissed him strongly once, but kissing was not what he was interested in. Jason smiled broadly as Jimmy sank to his knees and quickly undid his belt. They both tugged Jason's pants and briefs down and his cock sprung to attention.

THIS was what Jimmy wanted. This was what he was hungry for. Cock. There was no question when he walked out of the door of his apartment that he was looking to suck cock tonight. Jimmy took Jason's cock in his hand and slowly ran his fist up and down it. It was not huge, but it was not small. It was very wet. Jason leaked lots of precum. Jimmy leaned in and sucked the delicious juice from the head of Jason's cock. He then slowly lowered his mouth down the length of the prick. When the cock reached the back of his throat he closed his lips tightly and slowly drew back.

He then admired Jason's cock. He had intentionally applied lipstick that would smudge. When he drew back he admired the lipstick that he had left on Jason's cock. His lipstick. He had left HIS lipstick on that wonderful cock. And the cock was held tightly in his hand with long blood red fingernails. He was entranced by the vision. His red lipstick. His red nails. His saliva on the cock. A man's cock.