Robin and Jimmy Olsen - Sissies Ch. 03

Story Info
Jamie Olsen needs to earn some extra money.
5.8k words
4.69
18.1k
6
0

Part 3 of the 10 part series

Updated 06/13/2023
Created 08/27/2011
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

Part 3

Jamie’s story

The few days before the date in Part 1...

The car pulled up at the curb and Jamie got out of the passenger side door. She was a bit wobbly on her three inch heels. The car sped away fast, as if the driver was feeling guilty about what he and Jamie had just done.

Jamie opened her purse and tucked away the fifty dollars she had stuck in her bra shortly after getting into the car. She also pulled out a cigarette and lit it, dragging deeply on the smoke. The flavour of the menthol cigarette helped to wipe away the residual taste of the cum in her mouth. A breath mint afterwards would help mask the flavour and odour as well, in case her next john wanted to kiss her.

While she smoked, she opened her compact and checked her makeup, she used a tissue to dab away a bit of cum from the corner of her mouth, and also a streak along one cheek. Fortunately she had managed to swallow most of the john’s load and there was not much damage to repair.

She also saw that her hair looked fine. She had taken her normal drab red hair and coloured it a bit more brightly and styled it more femininely for the evening. Before leaving the apartment she had changed from her more masculine day clothing to her preferred sissy clothing. And tonight, she had put on what she was starting to think of as her evening work outfit. In addition to her three inch heels, she was wearing dark stay up stockings, very skimpy black leather hot pants, a short short neon green tube top that left her pierced navel exposed.. oh and a very small pair of thong panties that barely contained her nice sized pricklet. She had a row of tiny fake emerald studs in her left ear, matching the large fake gem in her navel. The green looked very delicious with her red hair!

She was wearing small breast forms under her top. She had been getting hormone injections for over a year now, but was disappointed that her breasts had barely developed at all in that time. So little that they barely made any bulge in her top at all. On the other hand, she had been told that the hormones had been specially formulated that they did not cause any problems with her getting an erection. In fact, if anything, she was hard much more often than she used to be!

This meant that at this moment, anyone observant enough would notice the very slight tenting of her hot pants and would figure out that this particular street walker was not a girl. Which was not unusual for this section of the stroll in this particular area of the city.

But then despite thinking of herself as “she”, Jamie did not make any pretences of being a girl. She was a man, barely beyond being a boy, but in reality, she was a sissy! And she had all the cravings of a sissy. She wanted to look feminine. She wanted to dress feminine. She wanted to suck cocks and get fucked by cocks. But she definitely wanted to still be a boy and to have people know she was a boy - even if it was a limp-wristed cocksucking faggot of a boy!
Her life had changed dramatically over the past couple of years, ever since she realized she was a sissy. At the office, she was no longer a cub reporter, eagerly seeking out the latest crime stories and covering the exploits of her best pal, Superman. The hormones had affected her muscle mass and she was no longer fit enough for those adventures. Heck she was no longer even a reporter for the paper! As she had slowly developed more effeminate mannerisms and started swishing around the office, Perry had become more and more embarrassed at sending him/her out on assignments. Now when she heard the cry of “Olsen! Get in here!” it was not to be sent out on a story, but rather to be handed a bunch of papers to be filed away!

Lois and Clark had been sweet, but concerned. They had taken him aside, individually and together, to talk to him and express their concerns that he had perhaps been exposed to some exotic virus or toxin on one of his adventures to another planet, or perhaps one of the criminals he had exposed had done something to his mind! Jimmy, as he was still known at the office, despite repeatedly saying he wanted to be known now as Jamie.. Jimmy had just laughed at them and told them the truth... that after several assignments that required him to dress up as a girl, he found that he so much more enjoyed dressing more flamboyantly than his normal drab boy clothing.

And dressing more effeminately had drawn attention from men. Certain kinds of men. He quickly realized that he actually liked having men attracted to him. He wanted their attention. He began flirting with those men, nothing serious of course. After all, he was a man himself... wasn’t he? But the flirting got more daring and he found himself becoming more and more aroused by the attention.

All of this had escalated slowly to the point that even when dressed as masculine as he did for work - which he now thought of as “butching it up”, he was still wearing eyeliner and eye shadow, and his finger nails were always painted - and he was always wearing panties and stockings underneath! He was just dying to start wearing a bra to the office as well, but his titties had not developed enough to realistically need one!

When he was at home, well, then he could dress in all of the wonderful new outfits that his poor newspaper earnings could afford! Which was not a lot. Especially since he no longer drew a reporters wages. So he had had to look for other income.

As she strolled along the couple block stretch of this not very nice neighbourhood, she said hello to her competitors who were also trying to make a meagre living. They had resented her at first, but once they saw that she was not chosen much more than they, they just accepted Jamie as one of them. There were all sorts trying to earn a living here from the continual parade of cars. Some were just young men, selling their asses for drug money. Some were transitioning transsexuals, looking for more money to complete their surgery. A couple of others were like Jamie, mincing sissies, boys who would never be mistaken for girls, but were feminine enough to attract the men who did not think of themselves as gay, but who still wanted to find a dick when they lifted the skirt!

Jamie loved her BFF Robin. Robin was also a cockloving sissy, but she had it easy! Robin lived in a big mansion and had all the money she could possibly want. Robin was a few years younger than Jamie. The two had awakened to their sissy needs at about the same time and had given each other support. They had also given each other many many creamy cummies exploring each other’s bodies whenever they got together! Robin had managed to convince those around her to stop using her boy name, Dick. Robin seemed like just the right name for the sassy sissy!

Jamie missed Robin. They had not seen each other for almost two months. Sure they talked on the phone and texted constantly, but Jamie SO missed snuggling and cuddling their soft bodies together!

Another car slowly drove down the street, its window open so that the driver could inspect the various girls and boys who were calling out to him. The car stopped and the driver beckoned to Jamie. Jamie minced over to the car and asked the driver if he liked what he saw. Evidently he did because he told Jamie to get in. Jamie directed him to drive to an alley a couple blocks away. When they stopped they haggled over price briefly. Jamie was disappointed that the john was not willing to pay enough to fuck her ass - both because she had not yet had her ass fucked tonight and she REALLY needed a cock in her ass, but mostly because it meant she would not make as much money from the guy.

They got out of the car. Jamie took a flattened cardboard box and placed it beside the car. She knelt on is as she unbuckled the john’s belt and pulled down his pants. His dick was disappointingly small. Perhaps it was just as well that he did not want to fuck her. She would not have gotten any enjoyment from a cock that size - heck HERS was bigger! So it was just as well that she suck him off as quickly as possible and get back to the street.

She worked his cock with her mouth and hands. The john tried to grab her head, but she yelled at him to not touch her hair, and the guy just rested back against the car. It took less than five minutes and she had him shooting off in her mouth. She opened her mouth to show the john her mouthful of cum, then swallowed and showed him her open mouth.

The john was a smoker, so she did not mind when she lit up a cigarette in the car while he drove her the two blocks back to the stroll.

In the beginning she had not let the johns ejaculate into her mouth. But she quickly learned that if they did not, then they made a mess of her makeup or her hair or her clothing. And if she did not swallow, often when she spit, she got it on herself. So better to swallow the load. She was a very practical gal.

Back on the stroll she did a quick calculation and realized she had only made a hundred and fifty dollars so far. And she would not be making much more tonight. She was working this particular hookers row tonight because it was the third Thursday night of the month. And every third Thursday night at 11 pm, her special ride picked her up.

And there it was now, a long black limousine pulled up to the curb. She did not get in back though. She got in the seat beside the driver and said “Hello Roscoe!”
Roscoe replied “Hello Miss Olsen. Did you have a good evening tonight?”

Jamie pouted, “No, not very well at all! But you know I always enjoy myself by the end of the night!” Jamie reached over and placed her hand on the thigh of the large black man. “Have you been saving up a load for me, Roscoe?”

“You know me, Miss Olsen. I’ve always got something warm and gooey for you!” he leered at her.

The limousine pulled into the underground garage of the city’s tallest skyscraper. After they parked, Roscoe and Jamie went up the private elevator to the suite of floors at the very top of the building. In the elevator, Jamie unabashedly stroked Roscoe’s large cock through his pants. If the elevator ride had not been so fast, she would have unzipped him and reached in to stroke the actual flesh!

Having been here every month for the past year and a few months more than that, Jamie was familiar with where to go. She made her way down a hallway and entered a room that looked very much like a doctor’s office. She removed all of her clothing except her stockings and heels. Roscoe had entered in behind her and stood by the door, silent and immobile. While she waited, Jamie danced about in front of the black man, her erect cock bobbing as she did so. With a smile, she noted that Roscoe’s cock was trying to tent his pants. She turned around and rubbed her naked ass against that hard bulge. It felt so good! She wanted that cock!

The other door to the room opened and Dr. Kilgallon entered the room. The doctor was a very attractive blonde, about forty years old. She had high firm breasts. Jamie had never seen her without a lab coat on, but she imagined that the doctor had a very fetching figure underneath.

The doctor had Jamie bend over a counter and took a very large, very long needle. She filled the syringe from a vial, and then injected half of the contents into the left cheek of Jamie’s ass, and the rest in the other cheek. As always, Jamie’s ass burned for several minutes, but the itch soon faded.

Jamie was then led into the next room. Having been here before, she immediately sat in the large complicated chair in the middle of the room. Dr. Kilgallon gave Jamie a small cup of liquid which she swallowed. The doctor then strapped her wrists to the arms of the chair and placed headphones on her head. She squirted something in Jamie’s eyes to freeze them, so Jamie did not have to blink and then used delicate probes and hooks on Jamie’s eyelids to ensure Jamie’s eyes would not close.

The doctor left the room and went to a control room next door. She dimmed the lights in the room and then began to play a video on the wall in front of Jamie.

Jamie woke up on a couch. She had no memory of how she got there. But she did feel very relaxed, and very horny too. If she did not get fucked soon, she was going to scream!

Her clothing was beside her and she dressed as she did every month. There was a glass of wine on the counter, as always and she took that with her down the hallway. She opened the large ornate door and entered a huge living room lounge area with tall glass windows revealing the entire city downtown!

She wandered around the room for a bit, admiring the very expensive furniture and decorations. She turned and smiled as another door entered and a large bald man entered the room, followed by three bodyguards. Jamie smiled to see THREE bodyguards. This was going to be fun!

She skipped her way over to the billionaire and hugged him tightly. “Lexi!” she exclaimed!

Lex looked disdainfully at the mewling sissy. He did not return the hug, nor even smile at the sissy.

“Oh Lexi, I know you love me!” teased the sissy. “Won’t you give me a kiss, just once?”

Lex sat in a very comfortable chair and lit a cigar. The chair was set up in front of a large open area that had an expensive rug. He motioned the three bodyguards over in front of him. They nodded and began to remove their clothing. Jamie moaned in delight and removed her own top and hot pants. Her pricklet strained her panties, until she tossed those aside as well. She fell to her knees and waited.

Bruno was the first to grab hold of her and pull her body close to his as he kissed her hard. Jamie sucked on his tongue eagerly and wrapped her hand around his thick cock. She pulled and jerked on it as Bruno pushed her back down to her knees. She eagerly engulfed the head of his cock in her mouth and then plunged her head down on his thick shaft. It filled her mouth so deliciously. She loved the hard firmness of the cock, and the heat in her mouth!

When she - no HE - had been dating Lois’s sister, Lucy had outright refused to suck Jimmy’s cock. Boy, was she missing something! Jamie absolutely loved sucking on a gorgeous hunk of meat.

Another cock bumped against her face and she turned her head to take Jerry’s smaller cock into her mouth. She kept her hand on Bruno’s dick, continuing to fist him and keep him firmly erect. Soon she was bobbing her head back and forth between the two delicious dicks. Each was drooling good amounts of precum and she eagerly sucked this up and swallowed. She loved the taste of their juices!

How had she ever enjoyed herself before discovering she was a sissy she wondered? Sure she had had all kinds of amazing adventures with Big Blue! Sure she had had alien princesses trying to lure her to be their kings! But nothing compared with putting on lipstick and sitting in a gay bar, waiting for the right man to come along and light her cigarette and feeling the man’s hard cock growing as she stroked it, and the eager anticipation of knowing that that cock would soon be driving deep into her ass!

Speaking of which, she wiggled her ass invitingly and moments later she felt a tongue probe at her anal entrance as Reggie knelt behind her! Moments later, she felt the head of Reggie’s hard dick push against her sphincter. She relaxed a bit and giggled in delight as Reggie’s cock slid slowly inside of her. Jamie pushed back and Reggie sank fully into her. Oh how she loved being filled by a hot cock! She loved the feel of a large cock sliding in and out of her boipussy, scraping the lining of her anal cavity, stretching her wide. She almost creamed herself, her own pricklet so hard and rigid as Reggie’s plunge in her ass hit her prostate and made her cry out in pleasure. Oh, there was nothing more glorious for a sissy fagboy like her than to have her ass fucked deep and hard by a real man’s hard throbbing cock!!

And to think that just two years ago she had thought herself to be a young virile man, chasing women and eager to put his cocks in their pussies. So much had changed! He had become curious and then could not resist the simple temptation of reaching into a man’s pants and drawing out his thick member to lick and suck and then to realize the power he had over a man to make him spurt his seed down his eager throat!

Jamie remembered the first time a man had slid his cock into her ass. She had been dressed totally as a boy, other than the stockings and panties beneath her jeans, but Arthur had spotted her true nature weeks before. Arthur had been tall and handsomely rugged, as befitted one of Big Blue’s teammates. Arthur had striking blond hair and dark smouldering eyes. Jamie had not resisted when the handsome Atlantean had taken his hand and quietly led him to his quarters. As soon as the door had closed, their lips met and they kissed with such passion. When Arthur had pressed his cock against her sphincter and looked into her eyes for permission, Jamie had nodded and then kissed him hungrily. She had cried out in pain and at the pleasure of being taken by a true man for the first time! Arthur had visited her several times since, as had many of his teammates!

She paused in her cocksucking to look over at Lex. Lex had almost finished his cigar. He had his pants open and one hand was wrapped around his own cock. Unfortunately that cock was small, only about three inches long and not very thick!

Bruno grabbed Jamie’s head and shoved it back down on his cock. Jamie opened her throat muscles and slid her mouth right down to the root of his cock. When she pulled back to get a breath, Jerry then bottomed out in her mouth. He held her there for so long that she began to black out from the lack of air. But he finally released her and she drew back, gasping for breath, incredible amounts of drool and saliva running down her chin to drop on to the expensive carpet.

Reggie grabbed her waist and vigorously pounded her ass. Then he thrust deep one last time and held his cock there as he pumped his hot jism deep into her bowels. Jamie groaned. This was one of the best sensations she knew, feeling her insides washed with the hot splooges of a man’s cum!

Moments later, her mouth stretched incredibly wide as both Bruno and Jerry both pushed their cocks into her mouth and they both came at the same time. She swallowed as much as she could. Her tummy was going to be so full!
The three bodyguards pulled back, leaving Jamie panting heavily from her exertions. She was a very very happy sissy. As the boys put their clothes back on, Dr. Killgallon led Jamie to an unusual chair. Jamie sat down and the doctor had Jamie place her arms on the armrests of the chair. She then fastened manacles to Jamie’s arms and legs, holding them tightly to the chair.

“Is she secure?” asked Lex.

“Yes,” replied the good doctor, stepping back.

Lex strode forward and instructed Jamie to turn her head. Lex’s small dick was erect and Jamie happily opened her mouth, taking the entire cock inside. She twirled her tongue around the cock and bobbed her head up and down on it, as much as she could on such a small cock. Jamie referred to her own pricklet as, well, a pricklet, or a dicklette, or a pee pee.... but truly she had a larger cock than Lex did!

Lex grabbed her head. She loved it when Lex did that, for it was the only time that this wonderful man ever touched her! Lex began to quicken his pace and then began to groan.

“I’m... I’m almost there!” said Lex. “Doctor.... whisper the code word to her NOW!”

Lex took a firm hold on Jamie’s head. Jamie was in heaven as Lex began to shoot his watery discharge into her mouth. The first few jets splashed against the back of her mouth and she eagerly swirled the jism, savouring the flavour of the seed of this powerful man!

And then Dr. Killgallon whispered something in her ear, and suddenly Jimmy Olsen realized that he had a man’s cock in his mouth and his mouth was full of the man’s cum! Oh god, what am I doing, he thought, and he struggled against his bonds!

12