Teaching My Boss a Lesson Ch. 02

Story Info
Jess and her boss have some play time.
2.4k words
4.16
55.6k
10

Part 2 of the 2 part series

Updated 10/06/2022
Created 10/03/2009
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

(note this is the second chapter to a previous story)

*

Jess pulled the car into the parking lot of her apartment building, flipped it into park and turned the car off. She turned to look at the slut sitting next to her. "Alright slut, time to face the music. We are going upstairs but Mistress needs to make sure everything is in place for her slut."

Jess reached over and uncuffed her slut from the door. Got out of the car and walked around to the passenger's side door, she opened the door and Tiffany slowly got out of the car straightening the little bit of clothing she had on her body. "Yes Mistress, anything you wish."

Jess took Tiffany by the hand and led her into the building. Tiffany followed her new mistress eagerly but looked around nervously as they walked into the front lobby. The doorman gave the couple a look as they passed and Tiffany hesitated. "Slut, don't dilly dally. Move!"

Tiffany jumped to obey her mistress, her clitty twitching with the degradation of being called a slut in front of a complete stranger. They reached the elevator and Jess turned to her slave. "You will wait here until Mistress sends someone to get you."

A look of fear flashed across the slut's face as her mistress again pulled out the handcuffs. Jess took her slut's wrists and cuffed her to a railing on the wall. "You are not to talk to anyone, slut. You are mine and only mine unless I decide to share you with someone. Mistress will send someone to get you when she is ready for you; you are not to speak to them either. Understand slut?"

"Yes, Mistress, whatever you wish Mistress." Tiffany lowered her eyes in submission as her mistress walked into the open elevator leaving her handcuffed to the railing.

Tiffany began to lose track of the amount of time she stood there waiting for her mistress to come and get her. To her good fortune no one had walked past to see her in her utter humiliation. Tiffany thought she was in the clear that no one would see her when two frat boys walked around the corner to get on the elevator. They both looked her up and down clearly checking out the long shapely legs covered up past the knees in leather boots and the tight red and black lace trimmed outfit. One moved towards her.

"Hey baby, how'd a sexy little thing like you get all tied up here like this?" As he walked towards her Tiffany kept her head down and tried to remember that her mistress had told her she was not allowed to talk to anyone. The frat boy walked closer to her and reached out to graze his fingers up her bare arm.

"What can't you talk to me? Come on baby at least tell me your name. Come on you sexy little thing. All dressed up like this and you won't even talk to me? I'm David, come on baby what's your name?" David's hand drifted down Tiffany's back and he took a firm handful of her tight ass. Just as his hand grabbed her ass the elevator bell dinged and the door opened. Tiffany looked up quickly hoping she was saved. If this David kept up touching her he was going to find out very quickly her secret. The utter humiliation of being handcuffed and not allowed to talk while dressed as a complete slut was taking Tiffany so close to the edge she was unsure how long she would be able to hold off blowing her load.

As the elevator doors opened Tiffany saw a leggy blonde step out. She looked about 22 short curly blonde hair and piercing blue eyes. She was wearing a black trench coat and knee high black leather stiletto boots. She approached Tiffany and David. "Hands off gentleman, she is all mine."

The blonde reached over and unlocked the handcuff from the rail. She took the empty cuff, flipped Tiffany around, cuffed her hands together behind her back, and pushed her towards the waiting elevator. Just before the doors began to close the blonde winked at the frat boys, "maybe next time boys, sorry." She winked and gave a little wave as the doors closed on the boys, whose jaws were on the floor.

Once they were alone in the elevator the blonde turned to Tiffany. "Your mistress is waiting for you upstairs. I will take you to her. You will serve us both tonight, you will call me Lady. You will do what we say or you will be punished. My orders will not contradict your mistress's but you will listen to her over me. If you understand nod your head slut."

Tiffany looked up at her second mistress and in utter submission simply nodded her head as the elevator came to a stop and the doors opened before them. Lady walked out of the elevator, her slut following close behind, they reached the door of the apartment and as Lady opened the door Tiffany took a deep breath and stepped into her mistress's apartment.

The lights were turned down low all Tiffany could see were basic outlines in the shadows, as her eyes adjusted she saw her mistress standing in the center of the room. She was wearing a tight black leather corset with a short pleated black leather skirt. Garters peeked out from underneath what existed of the skirt attached to black thigh high stockings. The outfit was completed with knee high black leather boots and a riding crop in her hand. Tiffany was so floored by the beauty of her mistress that she stopped moving across the room.

"Go kneel before your mistress slut." A voice made her senses click back on; Tiffany looked to her right and saw that Lady had taken off her trench coat to reveal a matching outfit to the woman standing across the room. Tiffany's clitty had never been so hard she was completely under the control of these two beautiful women and she wanted nothing more.

She slowly walked across the room towards her mistress who was tapping her riding crop against her hand impatiently waiting for her little slave to approach her. Tiffany reached her mistress and dropped to the ground in front of her, on her knees her hands still cuffed behind her back.

"There's my pretty little slut. Were you a good girl downstairs when mistress was getting ready for you?"

"Yes Mistress, of course Mistress. I only do what Mistress says." Tiffany looked up at her mistress.

"She lies to her mistress, she is nothing but a dirty little slut willing to put out for anyone who offers up their cock." Lady put in her two cents from behind the kneeling slut.

"You lied to your mistress slut? Mistress is not pleased." She reached out and snapped the riding crop against her slut's thigh just above her boots. Tiffany twitched with the pain.

"No Mistress I did not lie to you. I did everything you asked of me. I did not say a word to those boys, they touched me, there was nothing I could I do. I did what you asked of me Mistress. I would never disobey you I live to serve and only you Mistress."

"They touched you? You are my slave no one touches you without my permission." She snapped the riding crop against Tiffany again, and her slave twitched with pain again.

"I am sorry Mistress, I am a bad girl, and I deserve the punishment you are giving me. What can I do to apologize to you Mistress? Tell me how to please you Mistress."

"Come closer slut. Lady, uncuff her." Tiffany moved closer to her mistress and Lady leaned forward to uncuff their captive, her perky breasts brushing against Tiffany's back as she did. Once Tiffany's hands were free she reached forward to touch her Mistress's boots.

"Do not touch me slut unless I tell you to." Mistress snapped the riding crop and Tiffany flinched again.

"Yes Mistress, I am sorry Mistress." Tiffany's hand went to her sides.

"Use your tongue slut, pleasure your mistress, you will not use your hands, just your mouth." Tiffany moved forward as her mistress lifted the front of her skirt. A black garter belt came into view but nothing else covered her shaved cunt. Mistress spread her legs slightly to give her slut better access, and Tiffany took a breath before she moved to pleasure her mistress. Her tongue moved in separating the lips of her Mistress, easily finding her clit. She wiggled her tongue slowly vibrating her Mistress's clit as let out a slight moan. Tiffany leaned in slightly to suck on her mistress's clit causing her mistress reach out and grab a hold of the chair nearest to her. Tiffany turned her attention to the rest of her Mistress swirling her tongue in and out of the folds, around the very edge of her vagina before plunging in. Soft moans from above her let Tiffany know that she was pleasing her Mistress. She moved back to pay attention to her Mistress's clit again, hoping that her Mistress would climax and reward her little slut. The moans from her mistress were making Tiffany's clitty so hard she was having a hard time not touching herself. Hoping that her mistress would not notice Tiffany reached under her skirt to rub herself. Just as her hand reached her now rock hard clitty she felt the sting of the riding crop on her back. Shocked by the sting she stopped paying attention to what she was doing and turned around to see where the sting came from. Lady was standing over her riding crop in hand.

"You are pleasing your mistress not yourself slut. Remove your hands now."

"Who said you could stop slut?" Mistress had now regained some composure and the flush in her cheeks was not just pleasure.

"Mistress he was touching himself, and I know you want all of his attention on you." Lady snapped the crop against her hand to make her point.

"I'm sorry Mistress, I couldn't help myself I am sorry. Please Mistress I am a bad girl." Tiffany looked up at her mistress.

"Yes you are a bad girl. You have lost the privilege to please your Mistress. Get up slut."

"Yes Mistress." Tiffany scrambled to her feet.

"Go stand over there." Mistress waved her hand in the general direction of the other side of the room. Tiffany scrambled to obey her mistress. "See that banister slut? Go pose for me; show me what kind of slut you are."

Tiffany turned to look at her mistress. "Mistress?"

"Lady will be your photographer. Go pose for us. Please us and you will be rewarded."

Tiffany moved towards the banister that lead to loft above the living room. She reached a hand out tentatively to grab a hold of the banister. A little unsure of what to do she leaned into the railing sticking out her tight little ass so that straps of her garter belt pulled even tighter. Lady snapped a picture. Tiffany looked to her mistress for approval. Her mistress's hand sliding down her body and under her skirt was enough inspiration for Tiffany, knowing she was pleasing her mistress she began to get more daring. Using the banister like she was a stripper, Tiffany moved up and down the pole grinding against it as Lady snapped picture after picture. The idea that someone was documenting this was making Tiffany very hard in her silky panties, her precum oozing out staining her panties.

"Please Mistress, let me please you. Please let me cum, please Mistress." Tiffany turned to her mistress and dropped to her knees.

"I think maybe we should let the little slut do what she wants." Lady turned around to face Mistress, "but only if I can document that too."

"Come here slut," Tiffany crawled towards her mistress. "You may use your hands or your mouth to please me."

Tiffany leaned forward to take her mistress into her mouth sucking on her clit. As her mistress moaned her pleasure Tiffany reached as hand up her mistress's thigh and towards her cunt. She played around the edge before pushing one finger into her mistress. Her mistress's head fell backwards in pleasure and Lady snapped a picture just as the finger disappeared into Mistress. She moved her finger in and out of her mistress as she continued to play with her mistress's clit with her mouth and tongue. Tiffany could feel her mistress tighten around her finger and she knew she was getting close to her orgasm. Tiffany kept pushing and playing with her mistress until she was able to push her mistress over the edge. She felt her mistress tight around her as she moaned out her last pleasure; Tiffany's fingers were wet with her mistress's juices as she slid her fingers out of her mistress. Mistress took the hand and moved it towards her slut's mouth; Tiffany eagerly sucked her mistress's juices off of her fingers. Mistress pulled her to her feet.

"You did well slut, Mistress is pleased. Go sit on the couch." Tiffany moved towards the couch and sat down tentatively.

"Please Mistress Let me cum, please Mistress. I will do anything, please Mistress let me finish."

"She has been a very good girl Mistress; maybe we should let her get off. Or we should watch her get herself off."

"I think that is a very good idea Lady. Alright slut you may get yourself off. Lady, take more pictures. Oh and slut, make sure you put on a good show, you are going to post these on your very sexy MySpace that I saw earlier." Tiffany was so hard she had never been so relieved to touch herself. She began to rub her rock hard clitty; she knew it wasn't going to take very long for her to blow her load. She kept rubbing and rubbing feeling herself getting closer and closer to the edge. She looked up at her mistress and with one slight nod from her mistress Tiffany pushed herself over the edge her hot sticky cum exploding all over her silky panties.

Mistress walked over towards her slut. She bent down to kiss her gently. "You are such a good girl."

"Thank You Mistress" Both paused and looked at each other a moment passing between Jess and Cameron before they both snapped back into the moment.

"Now get up, its time to post these sexy sexy pictures." Tiffany got up off the couch and moved towards the computer.

"Yes Mistress anything you say Mistress." Tiffany logged into her MySpace and began to upload the pictures while her mistress looked over her shoulder.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousover 2 years ago

Wish I was Cameron / Tiffany.

cdCindy1cdCindy1almost 7 years ago
please continue

this was a great 2nd chapter. Please continue and tell us what happens next. I too am a sissy submissive closet CD and I wish my assistant became my Mistress. I hope in the next chapter Tiffany is "forced" to suck a real cock from another male slave belonging to Mistress. That's what I do regularly and I love it. Please continue. I can't wait.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
Busted Wearing Panties Ch. 01 He's caught by his stepdaughter wearing her panties.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
A Mistress to Obey Curious submissivw man meets a lady online then realtime.in BDSM
The Society He stumbles into a world dominated by women.in Transgender & Crossdressers
More Stories