Secretly Sadistic Santa Ch. 03

Story Info
Giada's boundaries are stretched, Secret Santa appears.
10.3k words
4.47
3.6k
2

Part 3 of the 6 part series

Updated 01/20/2024
Created 12/19/2023
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

Christmas time is here and Giada Lowder, up and comer at Donnovan LLC, is manipulated by her boss Walter Donnovan and her new lover Charlotte Weiger to sign an agreement to participate in Secretly Sadistic Santa or "Triple S". The "Leadership Training" that mixes the delight of the widely popular holiday game with the sadistic practices of a BDSM Master/Mistress. At the same time she has positioned the company for two property acquisitions totally near a billion dollars of potential revenue. Chapter three has Giada tumble deeper into "Triple S" and in love...with...everything...and reveals a surprising Secret Santa.

Giada's body was sore and bruised in spots, her pussy feeling the day after penetration she hadn't felt in a long time. Master Rossfellow over stepped his power, not sensing the hesitation his submissive was giving, steamrolling his cock first into her mouth then penetrating her cunt. Giada sat naked for a time after he left and before showering, feeling 'violated' was the word she had circling while the water ran over her spent body.

She had no time to lament her choices, what happened, she had to get some sleep and then wake and go into work on time. There was a call to the commissioners and a follow up on the letter sent to the primary contact for their acquisition. Dropping the angst from the evening and focusing on getting ahead on everything was a must and Giada knew how to shift her focus.

She got down to work the minute she got there making the morning productive. She took advantage of the proximity of her flat to work and walked home for lunch and a nap. She set her phone alarm and

"The Boss" singing "Santa Claus is coming to Town" popped her off the couch and she dialed her brother Joey, her sexual confidant, on the walk back to he office.

"No fucking way!" he exclaimed. "You didn't do all that shit! At least you didn't have to record and upload that!"

She had shared all of the Triple S details from the handout she had to fill out to her first endeavor with whipping herself and uploading it to FetLife.

"I'm not sure I wasn't raped," she said semi-serious, not being able to be serious about sex with her brother. "I never said, no or used my safe words. Really didn't have a chance."

"How did it feel?" He said, slightly concerned, but moving it to their usual debate on pushing boundaries and how it ultimately felt.

"I hadn't had a cock in a while, so I can say he felt good inside," Giada admitted. "I just wasn't ready for it so...I don't know...forced."

"That is unfortunate, those two things juxtaposed against each other" Joey's concern quickly moving to rational. "You had were turned out and that is never bad."

"Yes, I guess big sister finally has something on you," she said, their talks of all his escapades, hers prior to a week ago never held a candle to his group sex nights and multiple lovers. "And it was set up by my lesbian lover, try to top that!"

"Ummm, no comment..." he laughed nervously.

"Oh, you have a male lover now?" She said approaching the office.

"You think that's out of the realm of possibility? I mean I shower with dudes every day!" Joey joked.

"Talk to you later cock-sucker!" She ended the call on that smart-assed comment and went in the office, a little refreshed.

Giada knew Jessica Powers, Charlotte's temp who was out getting some work done with their sister company, was in a meeting but was nervous to encounter her now that lines were drawn by her husband Guy Powers better know to her as Master Rossfellow.

That morning Giada was had gotten good news from one of the commissioners about the letter and Mr. Donnovan had called her in for a 4 p.m. meeting. On edge from he night before, not knowing if she was done with the Triple S, maybe Mr. Donnovan was her Secret Santa and maybe he was going to reveal that now. Instead she focused on business only walking in confidently ready to present anything.

"He's my best source and he said the family was pretty shook by your letter," Mr. Donnovan stated as she sat down, his hands folded, fingers pads pressing together.

"When do we go back and inquire about buying, Sir?" Giada said instantly, the question she wanted out right away then nervous that she called another man 'Sir'...would it get back to Master. "Or do we have any confidence the city commissioners would go through with an eminent domain process and we wait?"

"Ms. Lowden, these things take time and..." Mr. Donnovan started and Giada cut him off, tired from the night before, snippy and more snarky than she'd ever been to the CEO.

"The more time it takes, the more chance it has to fail," Giada said standing up from her seat. "You men get all wrapped up in your protocols and your decorum sometimes, these people are tax cheats and will do anything to kick the can down the road. With all due respect to your sales department and your political wing, I want to take it myself on and wrap this shit up by Christmas!"

Her hands were on the table, her blouse open to the point her breasts were spilling forward, chest moving to her quickened breath, her eyes glued on Mr. Donnovan. She felt if he didn't say yes to this she would walk, this time for good.

Her actions were begging for a reprimand, Giada now visualizing his hand spanking her over his knee.

"You have a lot of passion and vision," Mr. Donnovan said, still calm, still thinking. "I'll make the call down to sales and partner you with our lead there, Candy McGlophlin. Let me handle the commissioners and be sure they're at least discussing a vote. They meet Dec. 23rd. I doubt they'll actually vote but the ramblings around it will keep the pressure on the Catrells."

"Very good, sir." Giada said and turned to leave. She got a couple steps away from him when he called her name again.

"Ms. Lowden," He said, now standing, his impeccably tailored suit showing he had the physique of a man 20 years younger. "If my daughter had spoken to me like that back in the day, I'd have tanned her backside with my hand."

"Noted," Giada said, having no doubt he was someones Master, or several here at the company. She felt nervous leaving, waiting for his voice to stop her in her tracks and commanding her to come and act on that spanking threat.

Leaving, Giada began to wonder how much currency she bought with her participation with Master Rossfellow last night, she was sure word got to Mr. Donnovan. She was headed to the elevator to buzz down to sales to meet Candy McGlophlin when Jessica called her name, turning her head to the tall woman.

"Ms. Lowden, do you have a minute?" she said wearing the hell out of a pencil skirt and dark green suit coat, high heals and hair up making her taller. "Your office?"

"Sure..." Giada said, realizing the CEO had just made a spanking reference, and her Master's wife, who she was to address as 'Mistress', was now calling for a private meeting.

"Door shut? Locked?" Giada said shutting it and the minute the lock was secure she finished the sentence. "Mistress.."

"You learn well, Child." Mistress Jess said walking towards her. "Master Rossfellow was very impressed, though he's now in my dog house, and I hope you remembered your lessons. I'm here to arrange the accompanying portion of level three. Did he tell you the third form of punishment?"

"The third is not for punishment, it's intended for pleasure and pain," Giada said, her head down as she wasn't about to hit the floor in her dress.

"Very good, Child," Mistress Jess said. "Email me the dates and times you will be working out after work this week."

"Permission to speak freely, Mistress." Giada said.

"Granted, Child"

"When you say Master is in the dog house, what repercussions does that have more me?" Giada asked, not sure she wanted to make an accusation of forced sex. "And I just want to say Master taught me well, however he didn't give me a chance to..."

"You are an amazing submissive, almost as good as you are dominant in the real estate law world," Mistress Jessica said. "We want to develop your potential fully and don't worry about Master Rossfellow, you will see it's been addressed and he'll not take anything out on you."

"I see, thank you Mistress."

"Email by 4 p.m. today," Mistress said. "You are dismissed."

Giada looked back at Jessica once out of the room and not alone. She was stunning, tall, athletic, her mind went to places she only let wander occasionally before this Triple S shit. 'How productive can this be as a leadership vehicle' she thought, it will certainly be a distraction and she just did allude to punishing Master.

The elevator doors opened to the sales floor, there was more hustle and bustle and it was less ornate and stately than the law offices upstairs. It was decorated for Christmas in a quaint, haphazardly way, like her parents house during the holidays, too many decorations mismatched over years of haphazard collection.

"Nice you could come down from the ivory tower and visit us," The young man, Peter Joshelter, who she met at the gym said. "Candy's expecting you, I'm her main law clerk and one of her sales leads."

"Good to see you again Peter," Giada said, his boyish handsomeness, short around 5'9" in stark opposition to Mr. Donnovan's, he had skinny pants with low or no socks in a contemporary shoe, colored collared shirt. "Which direction?"

There were cubicles lining the floor, once full but since COVID half the staff works from home. He pointed to the left side of the office space.

"I'm running to get something, so head in she's expecting you," Peter said and raced off.

What Giada didn't expect was the beauty of the 55 year old woman who had built the empire on the backs of the sales staff here, her office more ornate than the office space outside, years of awards and pictures of developments lined the room.

Her hispanic features stunning, dark shoulder length hair, wearing a soft, shimmering dress that accented a bust line the drew your eyes, not large, but perfectly supported and proper cleavage. The skirt she wore swayed as she walked towards Giada, who was in a trance.

"Candy McGlophlin" she said extending her hand.

"Giada Lowden. Pleasee to meet you Candy."

"I understand you're coming down here to tell me how to do my job," there was still a welcoming expression on her face while defending her territory. "How much sales experience do you have Child?"

The word 'Child' sent a shiver down Giada's spin, she concluded in that moment she was someones Mistress, just like Mr. Donnovan, she shook the thoughts off the aggressive first meeting and focused on the prize, the Catrell property.

"You must forgive me Ms. McGlo....

"MRS. McGlophlin," she said, getting jabs in to keep this young upstart off balance and keep her dominance. "My husband is wonderful except for the heritage of his family name. Continue please."

"I apologize, there's just a time crunch on this property and I want to be of assistance to your department," Giada said, still a little staggered by Mrs. McGlophlin's beauty, aggressive nature and the environment.

"Assistance, I was told by our CEO you want lead," Mrs. McGlophlin said. "Which is it?"

"Lead," Giada said and dropped her eyes for just a moment, then looked hard at the woman emphasizing the one word answer she should have initially gave Candy.

"Very well," Candy quickly said. "We have a dozen new proposals to get ready by the first of the year, I'm going to pair you with my clerk Peter...."

"Joshelter, yes we've met," Giada's giddiness jumped forward that she got what she wanted.

"Why yes, he said you work out in the afternoons. I'm a morning person for my exercise and anyways he'll meet you here if you want to set up on the conference table," Mrs. McGlophlin said. "I've got a rep meeting in five minutes. Good to meet you Giada."

The sultry woman moved out of the office and Giada felt both good and troubled by the encounter.

"Ms. Lowden..." Peter said busting into the room.

"You can call me Giada,"

"Giada, I have some good news," Peter said beaming. "The Catrells want to meet tomorrow morning."

Without warning Peter found Giada in his arms hugging him excitedly.

"We're gonna make this shit happen, come on and let's get to work," she said sliding out of his arms, their eyes lingering.

The afternoon was filled with profiles of the family, exact tax documents, sales proposals and calls to the team leads for help. She had everything ready and gave Mr. Donnovan a call.

"Meet me in my office at 4:30 p.m.," he said and hung up, it being a little after 4 p.m.

"Peter, come with me," she said, the hesitation in his expression showed he wasn't confident that he feared this encounter. She walked over to him, her gaze deep into his, he looked down and away. "Peter, you are a smart, charismatic man that every CEO with a penis would love to elevate in their company. The fact you're still down here shows me you are missing something, and it's confidence."

He looked back up at her and turned to gather things. She noticed the wedding ring and she wondered if he refused the "leadership training" when he got a chance.

They went upstairs, Mr. Donnovan was ready a little early and at 4:35, as Peter was working the numbers with Mr. Donnovan, Jessica came in with another folder. She walked past Giada, went to the coffee bar and made a pumpkin spice latte for herself, and sat down at the conference table. She leaned into Giada.

"Where's the email I requested?" Jessica slid back, sipping on her coffee, looking deviously at her submissive.

"Shit..." Giada said.

The rest of the meeting wrapped up in 30 minutes and Mr. Donnovan got up and announced, "Ms. Lowder, consult with Mrs. McGlophlin and figure out when and where YOU'RE delivering our next offer. You three need to figure out who's contacting whom."

He handed Giada a manilla envelope with the official offer and stipulations before walking out of his own office.

"I've got Candy," Giada said standing up.

"Sit, Child," Jessica said, Giada's head snapping over and seeing Peter's head down. Mistress seeing the distress in Giada's eyes with her tone in front of another worker.

"The Urchin can stay to watch this," Jessica said, pointing to Peter and moving a chair at the big table. "He needs to fill in some holes in his 'leadership' resume, watching you get punished checks boxes for both of you."

"Stand now, you must be punished for your insubordination," Jessica said, Giada inching upwards looking over at Peter. "Slide off your panties and hike that skirt up Child."

Giada slid down the left side and then the right and let them fall, stepping out of them, Peter looking up out of the tops of his eyes. She then pulled her skirt up, her bare ass showing.

"Urchin, come watch from back here," Jessica pointed to the space behind where she cleared at the table. "And hand me your belt."

Peter gave a 'shit happens' shrug to Giada who moved to the spot at the table. Jessica smiled getting handed the belt and without warning swung it length wise and snapped the end of it on ass.

"AHHHGGGGH!!!" Giada wailed, trying to hold it down, but Mr. Donnovan's office was cavernous and you weren't allowed in unless invited. "AGGGHHHH!"

The second strike had her fall forward onto the table. There was third, fourth, fifth and they kept coming until a tenth one clipped her taint.

"OHH! SHHHH!IIT!!! AHHHH! AGGHHH! FUCKKKK! AH! AHHH! OOOFFFFF! AHHH! GAHHH!!!!"

"Email me in five minutes or I'm coming to find you," Jessica said, reaching down for the panties, handing them to Peter with his belt. "Wear them the rest of the day, Urchin...No sleep with them on...wear them until morning, got that?"

"Yes Mistress," Peter said and she walked out, the large door slamming as Giada put the chair back and turned to Peter.

"This leadership training is fucked up," Giada said looking at Peter then looking at his left hand where the wedding ring was. "I hope your wife doesn't find you in them."

"You've got four minutes to get to your computer," He said and turned to Mr. Donnovan's bathroom to go put the panties on.

Giada raced to her desk, outlined that she'd be in the gym that night (Monday) and the rest of the week except Friday and mornings Tuesday, Wednesday and Friday. She felt relief hitting send and then felt the hot burn of the belt shots on her ass, the adrenaline of the moment, or Peter watching and having to do the email wore off.

She was heading to the gym when Candy McGlophlin stopped her in the hallway.

"Tomorrow at 2 p.m. we meet with the Catrells," she said, much less confrontational. "You take the lead and I'll review the documents to so I can help if needed."

"Thank you," Giada said, the older woman looking her over up and down, seeing the workout bag in Giada's hand.

"It's too bad you're such a good lawyer, because you'd make a good sales person," she said, whipping around her skirt rolling showing a hint of upper thigh. "Have a good workout."

Giada did, taking some of the frustration of the discipline out on the weights, she was embarrassed having it done in front of a young male colleague she found attractive. She felt ire towards Mistress Jessica, the stupid activity of sending an email to trip her up to get a punishment.

Finishing she gathered her things and got a water, headed into the elevator she pealed away from the tremendous view of the Christmas city from the top floor. She put on her favorite Christmas playlist and tried to call Charlotte, no success. She skipped and hummed to the Little Drummer Boy David Bowie/Bing Crosby, and rolled into her flat.

She fixed a lean dinner, read some from her Christmas book and put on a random playlist titled "Christmas Love" Her phone buzzed from a text around 7 p.m., it was Charlotte..."get on FetLife and access the live feed sent to you there."

"But I didn't friend anyone..."

Charlotte just texted back..."Trust..."

Anything FetLife meant the possibility of taking and uploading photos, or videos, appropriately "Baby it's Cold Outside" played while she get her lighting, camera and stripped before logging on her computer. She felt a little giddy, typing in her password, she watched as her profile appeared and there were several messages on her front page.

"Holy Shit!" she exclaimed, there were comments on her photos and video from the first Secret Sadist Santa request, in fact over 50 comments she counted scrolling. She did have to send her login information to Jessica the other day so she must have made her profile live to the world.

There were also 150 friend requests approved, so someone was monitoring her account. Lastly her message box was filled with over 100 messages, she opened it and found the titles to be a lot of the same aggressive sexual comments and asks, she clicked on the first one titled "LIVE FEED" as Charlotte indicated.

It was tempting for Giada to pour through the naughty messages and adoration, instead of following Charlotte's directions to get on the live feed. The message was from Mistress Jess366136, her hand clicked "Join" and she watched the video screen pop up, and going into 'full screen' mode, it did ask to join by video as well.

"Fuck, why not?" Giada said to the empty flat, the next song "Santa Baby" playing...

Immediately she saw herself in a small box and there was a figure on the screen suspended. The camera view was from the floor and soon she heard and saw stiletto boots and the end of the whip dragging.

"Clap! Clap!" echoed through the speaker, she assumed from Mistress, and Giada hopped to her feet, turned to the camera and spread her cheeks while bending over at the waist.

"Mmmmm, very good child...welcome." The familiar voice of Mistress Jessica said. "Kneel on the floor and let everyone see your front now."

'Everyone' Giada mouthed and turned, obeying her domme holding some sort of group video event on the website. Reading about the site Giada was interested in what those were like was now finding out. She presented her self to the camera, adjusting so it showed just below her face to her thighs on the screen.