Robin and Jimmy Olsen - Sissies Ch. 05

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Jimmy Olsen gets fired. Long live sissy Jamie Olsen!
8.7k words
4.8
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Part 5 of the 10 part series

Updated 06/13/2023
Created 08/27/2011
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Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie!

Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black leather shorty shorts and bra set. But it had drizzled rain all evening and so she had only had two johns all evening. One had been a quick blow job in the guy's car in an alley. The second guy had actually been good looking and was not self conscious about picking up a sissy hooker on a street corner. He had paid for the by-the-hour hotel room and had actually been interested in kissing Jamie and fondling her boyclittie before he bent her over the table in the room and had rammed his nice sized dick up her asspussy!

Jamie had been so desperate for that cock up her ass that she had almost offered to let him fuck her for free - until she remembered that her titty kitty was still a long way from its target!

As Jamie showered, she rinsed off the previous night's sweat and then used her fingers to make sure that her boy pussy was thoroughly clean. She slid two fingers inside herself and groaned as her dicklette sprang to instant erection. She giggled as she scrubbed away the last remnants of her weekend - the slutty makeup and the bit of cum that had crusted in her hair. Looking in the mirror she was pleased to see that the tint in her hair was still holding - her hair was still a bolder red than her natural colour.

Despite having to dress in boy clothes for the day, she still powdered herself after she had throughly dried off. In the mirror she looked disappointedly at her small titties. Months of hormones had not gotten her much more than an A cup set of tits. Yes, the hormones had also smoothed her skin and made her emotions much more feminine, but she longed for larger breasts. Not for herself, of course! Oh, no! She was happy to be a boy. She loved being a boy. Or rather, she loved being a sissy boy. Well, MAN, if truth be told, since she had turned 23 just a couple months back. She loved shooting her girly juices from her cockette. She never wanted to give up her willie!

She loved being girly though. She loved being a sissy and wanted to please a man in anyway she could. She loved looking in the mirror and seeing vestiges of her male self there. But she longed to be even more girly. She wanted softer skin, a cute kissable nose, a big round ass for a man to hold on to as he fucked her ass hard. She did not need tits. Boys did not have tits. But sissies had tits because tits were what pleased a man.

After a few years of adventures with the Big Blue Cheese, after being turned into porcupine boys, a genie and all kinds of weird creatures, after going undercover to get the biggest scoops for the Daily Planet, Jimmy Olsen had realized that he loved most those simple adventures when he had crossdressed for one reason or another. And so he had begun dressing in women's clothing at home more and more, and then had started venturing out to transvestite bars.

Thank god she had discovered that her friend Robin - well, formerly Dick - was also a mincing sissy. Robin had given up crime fighting and only wanted to service men's cocks now - the true calling of a sissy. They had been best friends before, but now they were best sissy friends forever! But Jamie was SO jealous of Robin. Robin now had a nice pair of firm titties, the result of implants bought by her sometime boyfriend Ollie, just before he had lost all of his millions. It had been several weeks since Jamie and Robin had gone out on their most recent double date. Jamie really hoped the two sissies could get together again soon for a bit of fun just between the two of them.

Jamie looked at the clock - she only had an hour before she was supposed to be at her desk, looking as mannish as she could manage these days. But that was only on the outside. She refused to be any more masculine than she had to be. She pulled on black panties and squirmed at how tight they felt on her dicklette. She then pulled on dark stockings which would not be noticed under her icky boy pants.

But running her hands up and down her stockinged legs made her dicklette throb. She tried to ignore the sensation as she pulled up her pants. She put on a white blouse that she was sure could pass as a man's shirt, except that the buttons were on the wrong side. Last she pulled on her green checked sports jacket and bowtie. But when she looked in the mirror she was horrified at how butch she looked. Perhaps... yes...

Just a small amount of eye shadow... the faintest hint. And a spray of perfume. If anyone asked, she would say it was cologne.

Looking in the mirror, she realized that it was hard to look as masculine as she once had. The hormones had subtly changed her body shape, and the jacket no longer fit as it once had. Plus the tweezed eyebrows, and the studs in her ear piercings...

She needed to calm down so she grabbed the package of cigarettes out of her Jamie purse. Jimmy did not smoke but, as Jamie, she smoked a lot since it added to her sissy image, especially when she was trying to be slutty, working her corner. She really needed a ciggie though, to calm her nerves. So she grabbed a lipstick from her purse and coated her lips. She lit the cigarette and inhaled the smoke. That felt SO good she thought. She smiled at the sight of the lipstick on the filter. So sexy!.

When she finished the cigarette, she wiped off the lipstick. It was time for Jimmy to go to work.

When Jimmy arrived at the office he went first to the coffee machine and poured a cup of coffee into a china mug, then hurried to his desk. Most of his work lately had involved cleaning up stories of other reporters for publication, rather than his own investigations. The city editor, Perry White, seemed reluctant to send Jimmy out on assignments these days.

Jimmy waggled his fingers in greeting at his two friends, Lois and Clark, as he passed their desks. Clark looked up briefly, then shook his head sadly and returned to his work. Lois frowned at Jimmy then pointed at his mug. Jimmy looked at the mug and then blushed with embarrassment as he saw lipstick marks on the edge of the mug. He obviously had not cleaned his lips as well as he thought. He hurried to the washroom and gave his face another good cleaning. When he returned to his desk, Lois smiled at him.

Jimmy checked his computer and found it strange that there were no articles or other material in his list of items for editing. Nothing at all. He reviewed the material for other staff and found they all had more than enough work - but his list was empty.

The reason why, soon became apparent. Perry White stuck his head out of his office door and bellowed, "Olsen, get in here!"

"Right away, Chief!" responded Jimmy automatically, and just as automatically White replied, "Don't call me Chief!"

When Jimmy got into the editor's office, Perry was seated and pointed to the chair opposite. Jimmy sat, but in an effeminate manner, keeping his knees together, and pointed to the side.

"I'll get straight to the point, Jimmy!" said Perry. "Management has decided to let you go. As of this moment, you are no longer an employee of the Planet!"

"What?" cried Jimmy, "But Chief. Why?"

"Why? Why? Heck, Jimmy, there are more than fifteen citations and complaints in your file from just the last two weeks for lewd and immoral behaviour around the office! Add to that the fact that no one wants to work with you, and any work that you DO do has to be redone by someone else!"

"Jimmy. I'm really sorry for you. I can't believe that these... these changes you've been going through have been your own choice. I put the blame on Superman. I feel that letting you pursue all of these cockamamie adventures with him has done something to your mind! I wish you would let him examine you, and find out what has gone wrong!"

"Nothing has gone "wrong" chief!" cried Jimmy. "I've just discovered who I truly am. I try not to let it affect my work..."

"Well it has Jimmy, and your work is unsatisfactory enough for management to decide that we are better off without you, and you are better off elsewhere!"

"But... but Perry.. What am I going to do for money?"

"That is not our problem, Jimmy. Perhaps George Taylor over at the Star will hire you. Or maybe you'll have to get a job as a waiter. For fuck sake, do something... anything other than what I hear you've been doing on Roosevelt street for a "second job" at night!"

Jimmy was taken aback to think that his nocturnal extracurricular activities had become common gossip at the Planet!

"Out of respect for your past work, I am not going to have you escorted from the building. You can clean out your desk and leave on your own. But I want you out of here in one hour. Come back on tomorrow afternoon and I will have your final cheque, including vacation pay, ready for you!"

"But Chief!" cried Jimmy. And he really did cry. Tears welled up in his eyes and he buried his head in his hands, sobbing. Lois came in from the outer office and led Jimmy back to his desk. Everyone in the newsroom watched as the effeminate man sobbed at his desk. Finally Jimmy pulled himself together and began putting his personal possessions in a cardboard box.

Clark and Lois both tried to console him. But neither was showing much sympathy for his predicament. Clark said, "Please Jimmy, let us have someone examine you. It doesn't have to be Superman if you don't want. Just a good doctor who can..."

"You don't understand," said Jimmy. "Even if there IS something wrong with me, I don't want to be "cured! I LIKE who I am! I LIKE being ME! And if you can't accept that, you aren't my friends!"

"Fuck this! Fuck all of you!" he cried. He took the box and threw it on the floor. "I don't want any of this stuff. Those things are memories of who I was, not who I am! To hell with you all!" He grabbed his jacket off the back of the chair and started to put it on, then stopped. That jacket represented all that was wrong with his life. He threw it on the floor and stomped away, but then stopped and picked it back up.

He searched the pockets and retrieved a lipstick, pack of cigarettes and lighter.

Outside the Planet building he hailed a taxi to take him home. It was expensive, but he needed to get home as soon as possible. The cabbie was surprised, looking in the rear view mirror, to see the young man apply a coat of lipstick to his lips, then light a cigarette and inhale deeply.

At home, Jimmy immediately went to his apartment and took all of his boy clothes and tossed them into trash bags. The bags immediately went down the garbage chute. Jimmy Olsen was no more. Only Jamie Olsen remained!

It was only a little after noon, but Jamie was exhausted. She had stripped off her shirt and pants and thrown them out with the rest of her boy clothing. Dressed in just her stockings and panties, she slipped into bed and cried herself to sleep. She awoke just as the sun was going down. The sleep had helped. Putting distance from the traumatic event had helped.

She knew what would make her feel even better. She tossed back the covers and arched her back. Her erect dicklette needed relief. She reached into her bedside table and reached for the lube and her kryptonite dildo. Well, it wasn't real kryptonite. But when she had seen the thick dark green eight inch dildo in the sex shop a couple months back, that is exactly what had come to her mind, and she had bought it instantly.

A couple dollops of lube on her fingers, pushed into her asspussy, and then she placed the thick head of the fake cock at her anal ring and slowly eased it inside. All the men complimented her on having a nice tight pussy, but she had been fucked so many times that she was able to easily accept any cock, real or fake, without any resistance. She moaned as she pushed the green dick deeper.

Each time she fucked herself with the thick cock, she imagined that it was Superman who was fucking her. Ever since she had become attracted to men, or more accurately to men's cocks, she had yearned for her super pal to fuck her. She longed to have his hard cock deep inside her sissy pussy. Oh why, wouldn't he fuck her!

Jamie changed positions. She slammed the base of the dick against the wall about three feet above the floor. The suction cup at the end held it firmly in place, and she slid her ass back onto the delightful rubber dick. Now she could wiggle her hips and sink the entire length into her anal sheath. When her ass cheeks hit the wall, she knew she had taken its full length up her ass!

She pounded her ass back and forth on the rubber dick. It felt so good. In her mind, she pictured Kal-el gripping her hips and ramming his cock in and out of her love canal. Oh, it felt so fucking good. Jamie grabbed her nipples and pinched them, sending another thrill through her body. Her turgid dickie was bouncing around, precum drooling. Then... yes... there... that spot right there... oh yes, she found the right way to thrust her ass so that the cock slid along her prostate delightfully and suddenly her sissy goo shot from her prick head. She gasped and emitted short sharp feminine shrieks as her jism flew onto her carpet!

Oh, that had been so fucking good. But this sissy needed much more cock! She had no job to go to in the morning. She could hunt cock all night if she wanted to. And, she did want to!

Eleven pm. Jamie walked out of her apartment and waited for the elevator to take her down. As the door opened she thought, shit! Standing in the elevator was old Mrs. Watson from the tenth floor. Despite the slutty clothes and heavy makeup, she recognized Jamie. "May the Lord have mercy on you, young man! But I won't! I'm reporting you to the superintendent, again!"

Outside, Jamie got into the front seat of the cab that was waiting for her. Jose had driven her home from the stroll many times in the past. They had an arrangement. Jamie lowered the zipper on Jose's trousers, and fished out his cock. She lowered her head and began to suck his cock as he drove through the light traffic. "Oh, that is good chica! If you were a real woman, I might leave my wife and marry your mouth!"

Jamie bit down softly on Jose's cock and giggled. It was smaller than she preferred, but a cock was a cock, and a sissy took any opportunity she could find to please a hard dick. Jose moaned and swerved slightly as his dick pumped its gooey load into the boygirl's mouth! "We're here, sissy! Call me if you need a ride home, but you know the deal!"

Jamie knew the deal. If she called Jose twice in the same night, he got a blow job for the first ride and he got to fuck her ass for free for the second. She had never called him three times in the same day, so she was not sure how she would pay that off!

Jamie passed the bouncer at the door and walked into the club. It was filled with smoke and filled with men. Well, men and a lot of waitresses. Good looking sexy, and sex hungry, waitresses. More waitresses than would be expected. On the stage, a couple of gals were naked, bumping and grinding against each other, putting on a show for the punters.

Jamie looked around but could not see Roscoe anywhere. She pouted in disappointment and walked to the bar. She lit a cigarette. Before she had even ordered, a man at the bar offered to buy her a drink and she gladly accepted.

Jamie had originally planned to work her usual block of the stroll tonight. With no job, she was concerned about how to make ends meet. Looking at her bank books, she had seen that she had several thousand dollars in her "titty kitty" account, but that was for buying boobs. Her regular account was almost empty and she was reluctant to touch the boob money. So she needed to get out and earn some money. And what better way for a sissy to earn money than on the end of a man's dick! That money was supposed to go in the titty kitty, but a girl had to eat.

But the trauma of the day had left her needy. Needy for cock, and needy for comfort. She needed to spend time with a friend, but Jamie had no friends. Jimmy could have called up Clark, or even Lois and spent time with them. But they had both made it clear that Jamie was not welcome.

The one person she looked forward to seeing was Roscoe, who drove for Lex Luthor. Roscoe had been the only man to fuck her on a regular basis, even if it was just once a month when she went to visit Luthor. But Luthor had ended those visits and so she would never see Roscoe again. Except that Roscoe had mentioned that he came to this club a lot. So if she showed up, and just happened to bump into him...

Jamie accepted the drink and turned to talk to the man who bought it for her. He was not handsome. None of the men in the bar were handsome. They were mostly mean looking and thuggish. Oooo... a sissy's dream bar. Rugged men!

Jamie did not really care what a man looked like. She was more interested in what his cock looked like - though she had never met a cock she didn't like! But she appreciated strong men because they had more stamina to fuck her for hours at a time!

As the man talked to her, she knew he wanted in her panties. But she also realized that he thought she was a natural girl. As Jamie looked around, she saw many waitresses serving tables, but also noticed many taking men by the hand and walking through a door at the back of the bar, and saw many happy men returning!

Jamie lay her hand on the man's arm, and then began to run her fingers up and down his forearm. He grinned and bluntly asked her how much it would cost to fuck her! Blunt and straight-forward. She liked that in a man. She took the man's hand and pushed all of his fingers down until just his middle finger was erect. She slid that finger between her lips and began to suck on it as if it was a cock. She saw him squirm uncomfortably, trying to accommodate his instant erection in his trousers. Then she took his hand and placed it on her groin, where he could feel her small erect dicklette in her panties.

He looked at her in surprise, but grinned. "I don't care if you've got a dick or a pussy. You're a hot looking chick. So long as I can fuck your ass I want you baby! How much?"

Jamie was delighted. "Five hundred dollars!" she said.

"Five hundred? In this place? You've got to be joking!" the thug exclaimed. "I can get ten pussies for that money here!"

"That was just my opening offer, sweetie," said Jamie, again sucking on the man's finger. "I really need to be fucked. A lot. I need big cocks, small cocks, white cocks, black cocks. I don't care what kind of cock, so long is it fucks my mouth or my asspussy, and squirts jism deep inside me!"

"Meaning what?"

"Five hundred bucks for you on your own, or if you can get seven other guys as well, I'll fuck you all for free. You just pay the house whatever it costs for us to get one of the rooms behind that door!"

"God, you are a little jizz junkie, ain't you?"

Jamie smiled and nodded.

"Give me five minutes." said the bruiser, and he left Jamie at the bar. Immediately another man sat down and offered his finger to her mouth. She pointed at her empty glass. The new guy nodded to the bartender.

The first guy was back in three minutes, with four ruffians following him. "I've got five other guys who are going to join us as soon as they finish their next poker hand. Is ten of us too many?"

"Heavens no, darling!" purred Jamie. "Bring everyone! My ass cunt needs cock!"

Five minutes later, Jamie was on all fours on a cheap bed in a cheap room in back of the club. Her stockings were even more torn than when she had walked in. Her blouse was open and her small tits were on view to all. In her mouth she had a large cock, which she eagerly gobbled on while her first cock of the evening slowing pushed deep into her poop chute! Oh, she was in bloody fucking heaven!