First Day On the Job

Story by enroshiva on SoFurry

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#1 of Sissy Series

The beginning of a series of short stories I am writing based on this world: https://inkbunny.net/submissionview.php?id=1238746 The gist of it is that there are three genders. Male, Female and Sissy. Sissies are boys that are identified as such after rigorous testing. Women basically rule the world, sissies are the second best thing that boys can be if they want to be a professional but it still is not easy as they are mainly secretaries and housewives. Males do mainly manual labor or do sports. Sissies often also drink a diet shake that transforms their "movements" in a way that leaves their asses clean and coated in a sterile lubricant. This follows the story of a sissy cat Lily and her struggles to make it in the business world.


In the tiny bedroom of an old apartment complex, a young cat slept on her twin sized bed, the sun still resting over the horizon. The blaring siren of the alarm clock caused Lily to shift in her sleep. The pink cotton sheets brushed up against her black and white fur. With a light moan, she reached to her nightstand and slammed her paw on the clock. She sat up and purred as she stretched out her arms while arching her back. A purple nighty with a pink ribbon clung to her flat chest. She tousled her short black hair and shook her head until she was awake. "Today's the day!" she giggled. She tossed the comforter aside to reveal her massive morning wood, barely contained by her striped panties. The tip reached almost to her chest.

She bounced across the room, out the door and into the bathroom. After a quick shower, she stepped out into the hallway, wrapped in a towel. The lock on the front door turned with a loud thunk. A busty grey wolf with short brown hair entered wearing a black leather jacket, miniskirt, black boots and fishnet stockings. "Oh! Morning Ruby!" said Lily. "How was work?"

"Fine." sighed the wolf. "The patrons were grabby like usual." She walked over to Lily and rubbed her cock through the towel. "It's just not the same since you left. You sure you don't want to reconsider?"

Lily grabbed Ruby's paw and turned away from her. "This job could mean great things for me. No offence but I want to be more than just a stripper."

"Oh you were so much more than that." Ruby whispered as she put her hands on Lily's shoulders. "There is no shame in using the gifts god gave you."

Lily stepped out of her grasp. "Well excuse me if i want to use my mind."

Ruby shrugged. "Suit yourself. Be careful though. I hear offices can be quite, interesting for us sissies."

"Where isn't that the case?" Lily chuckled.

"Good point." Ruby answered. "Well if you need me, I'll be passed out in my room." She turned away and walked to her room down the hall, shutting the door behind her.

Lily glanced at her watch. "I better hurry if I am going to catch the train." She strode back to her room and started getting dressed. She wore a black skirt with a matching blazer, a white blouse and black stockings with black flats. As she grabbed her purse and keys, she eyed a purple lily that sat on her dresser. She hesitated for a moment before pinning it on the lapel of her jacket. "Here goes nothing." she mumbled, walking out the front door.

On her way to the subway, she stopped at a cafe. As she waited in line, her figure attracted the attention of a few customers. Once she reached the front, she was greeted by a fox sissy with red fur in a brown apron. "Hi! What can I get for you?" she said with a simile.

"A diet shake please." Lily answered.

"Of course!" the fox responded. She turned around to a refrigerator filled with white bottles and took one. "That will be $2.50!" Lily handed the cashier the money in exact change the second she asked for it. "Thank you! Come again!" The fox said as Lily walked out of the cafe.

On the train platform, Lily tapped her toes rhythmically while sipping her shake. She glanced at her watch again. "Damn thing is always late." As she waited on the platform, a large bengal tiger in paint splattered jeans and t shirt approached her.

"Hmm do I know you?" he growled.

Lily turned her head away. "You must be thinking of someone else."

"I know I know you from somewhere. Those black splotches, the green eyes, I remember them but from where?"

"Either way, I don't know you." Lily replied.

"It's not too late sweetheart." The tiger teased.

The lights of the train grew as they came through the tunnel. The train slowed as it entered the station, eventually coming to a full stop. The cars were almost completely stuffed. A few people exited, making just enough room for Lily and her new acquaintance. Lily was squeezed between the tiger and the back of a large black stallion. The tiger rubbed his chin as he looked Lily up and down. His eyes locked onto the purple lily on her jacket and snapped his fingers. "I remember now!" He whispered. "You used to work at the Sissy Shack didn't you?"

Lily turned her head away. "That's not me anymore."

"So it was you." he growled. "If I remember correctly," he slid his paw under her skirt. "You are packing something wild down there." He gently rubbed her cock through her panties. She let out gentle moans from his strokes. It grew until it pressed up against her abdomen. "Ah, there it is." he purred. "Let's see how you feel in the back." He reached his paws to her ass, under her panties. He pressed his fingers into her moist tailhole. "Glad to see someone has been drinking her shakes like a good sissy." She moaned even louder as he continued to toy with her ass. Her face glowed a bright red.

Though her mind was clouded, she managed to hear a voice on the intercom say, "La Rose Plaza. Platform is on the left." With what little space she had, she pulled away from the tiger's grasp. The passengers flooded out of the car, pushing them both out onto the platform. Lily fixed her outfit and clutched her purse to hide her erection. She walked down the platform and up the escalator. "Please go down. Please go down." She chanted. Lily closed her eyes and took a deep breath. Her erection faded as she rode the escalator up. By the time she reached the top, it receded to a modest bulge at her skirt.

Lily rushed down the busy city street. The sound a million conversations accented by a chorus of car horns assaulted her ears. She arrived a skyscraper on 82nd street whose facade was laden in glass. Once inside, she stepped to the receptionist's desk. Behind it was a sissy cheetah with short red hair wearing a purple dress. Lily smiled and said, "Hello! I am Mrs.Charlotte's new assistant."

The cheetah grinned back. "Of course! Please have a seat. I will tell her that you have arrived."

Lily sat in the lobby checking her hair and outfit, making small adjustments along the way. The elevator chimed as a snow leopard in a red pantsuit and black heels stepped out, talking on a hands free headset. "No no no. You have a month to get the new product on the shelves or you're fired. I would expect more from a regional manager." She pressed on the earpiece to listen better "Less crying and more working! This is a drink company, not a feelings factory. Pray I never need to speak to you again." She pressed the button on the headset.

The receptionist gave her boss a cheerful smile. "Mrs.Charlotte, your new assistant is here!"

"Thank you Honey. Expect a gift basket in the mail!" She turned to Lily and beckoned her over with a finger. "Come."

Lily darted up and said, "Yes Ma'm!" and followed right behind her.

"Now," Mrs.Charlotte started, "You will need keep my schedule, move my appointments, fetch my coffee and meals, run my errands and keep yourself completely accessible during work hours to deal with anything else I need. Can you manage that?"

Mrs.Charlotte turned back to see Lily taking notes of every word she just said. They stepped onto the elevator alone. Lily looked up from her pad and said, "Yes ma'am. Is there anything else I need to know."

Once the doors closed, Mrs.Charlotte reached her paws between Lily's legs. She knelt as she pulled down Lily's panties. Her hardening cock whipped out, almost hitting her boss in the face. "Yes, this will do nicely." she purred. The snow leopard ran her tongue around Lily's tip sending shivers down her assistant's spine. She licked her cock up and down the shaft before deepthroating her all the way to the balls. Lily pressed her back to the elevator wall, trying to stay on her feet. Mrs.Charlotte fingered Lily's ass as she continued thrusting her head back and forth. Lily leaked a glob of pre into her boss's throat. The snow leopard massaged Lily's insides while working on her own clit with her free hand. The cat whimpered and moaned from her boss' motions as her face was shone red. Still sensitive from her previous encounter, it did not take much to get her worked up.

With a firm thrust, Mrs.Charlotte pressed her fingers against Lily's prostate. Lily threw her head back and screamed, "Oh god! I'm..I'm gonna.." her cock twitched as shot after shot of cum gushed into her boss' mouth. Mrs.Charlotte moaned as she swallowed each shot as it came. She sent more loads of warm spunk into her boss. Lily expected her to pull away like most but Mrs.Charlotte took it all without letting a single drop hit the floor. By the time Lily finished orgasming, The snow leopard had a slight bulge in her stomach.

She pulled her head back, letting Lily's cock pop out of her muzzle. Lily leaned on the wall panting. Mrs.Charlotte wiped her mouth, stood back up and adjusted her clothes. A small puddle had formed under where she was squatting. A bit of leftover cum dripped from Lily's penis and spilled on the floor. "Well I guess you can cancel my lunch." the snow leopard chuckled.

Lily did her best to compose herself. She frantically patted her hair back into place and pulled up her underwear, tucking away her flaccid penis. The elevator dinged as they reached the top floor. Mrs.Charlotte strode out of the elevator and said, "Let's go, we have work to do."

Lily followed her, looking back at the carnage that their activity had left. "What should I do about the mess?" she asked.

Mrs.Charlotte answered, "Leave it. One of the men will clean it up." They walked through an array of cubicles. Female furs all on phones or typing away at computers. "Now, unless I tell you otherwise, I want you by my side at all times. Also, next time, don't bother with the underwear."

Lily mumbled, "Just like my last job."

"What was that?" Her boss snapped.

Lily stammered, "Nothing ma'am. You were saying?"

Mrs.Charlotte continued, "Well at anytime I may have need of you. Unless I tell you otherwise, you should be at arm's length. You may have your breaks but keep them short. Time ismoney. Any questions?"

Lily finished scribbling down her boss' words. "No ma'am, I should be fine."

"Splendid!" Mrs.Charlotte exclaimed. She opened up the door to her large office in the corner, gestured for Lily to enter and closed the door behind them. Mrs.Charlotte started to open up her blouse and whispered, "I have a few things I need you to take care of."