Secretly Sadistic Santa Ch. 02

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Secret Santa teaches Giada, she learns to submit to the pain.
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Part 2 of the 6 part series

Updated 01/20/2024
Created 12/19/2023
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Christmas time is here and Giada, up and comer at Donnovan LLC, is manipulated by her boss Walter Donnovan and her new lover, Charlotte. Giada enters into an agreement to participate in Secretly Sadistic Santa or "Triple S", that mixes the delight of the holiday game with the sadistic practices she will soon find out are shared among her co-workers. Chapter two is about Giada meeting and submitting to her Master, chosen by her Secret Santa. This all while earning the company a lot of money, moving up in stature. Enjoy Chapter two.

"Good morning Giada," Danielle said to her in a spirited and energetic manner, the white lights of the Christmas tree setting off her amazing skin. "Great work the last couple days."

"Hey, girlfriend," Luis said, pressing his hand on her forearm, his cologne was intoxicating. "I see you filed for that eminent domain paperwork, should be interesting!"

"I talked to Charlotte last night," Clete said, wearing a Santa hat. "They have a temp coming in to help you work through paperwork, Jessica Powers I believe her name. Hey amazing work before, I didn't get to say anything to you earlier."

In between the compliments Giada's mind couldn't help but wonder what sadistic shit her fellow team leaders had draw in their holiday games. Did they skip through level one, two and three? Would she ever see their videos? If there was one thing they all had in common was they were all good looking in some manner, smart and charismatic.

She replayed whipping herself, the rush of uploading it to the kink site. Her mind drifted to her workmates, Louis and Clete, sizing up the power of Luis vs. Clete's smallish ass and obviously noticeable bulge in his tight pants, would she be given the choice to have one, or both of them. Certainly she wouldn't even if she was given the choice, or would she?

The hyperdrive in her sexual side had been released, controlled and then given the chance to cross lines, which she did every time. The office Christmas music filled the air, her work laid out in front of her, she was still in an ethereal state.

Her mind drifted to Danielle, her body fit and she was stacked. Charlotte didn't have the bust line Danielle did, Giada wondering how the amp tits felt against her naked body. She shook her head, looked around and looked down at her work.

"You've got to be able to function," she said to herself, wondering what Charlotte was doing on the east coast, then working on the property acquisition.

The morning went fast. Giada hammered through a list of lobbyists, contacting them referring to Mr. Donnovan and he would be in touch soon, then brought everyone into the conference room. There were futures discussions, cold deal conversations and in seeing each lead, her mind had to switch to them in cuffs, or gags, getting whipped or flogged. It made for a more sensual tone in her voice she noticed towards the end, the group more energetic she felt.

It was 11 a.m. and she was going to head to the gym, she needed to get some movement and blood flow. She gave everyone a text she was heading there so they wouldn't call and headed to the elevator, down to the locker room and changed.

Giada did some cardio and then some light yoga in the corner, out the the corner of her eye she saw a tall woman come in and start a dumbbell/kettle ball circuit, a HIIT regimen. Giada finished and went to the locker room to shower and get ready for the afternoon meetings.

The water felt good, Giada stayed in the shower a while and took her time drying off staying naked, walking among other's going in and out, getting approving looks from several of the other women, before getting dressed. Giada gathered her things and headed to the exit when the tall woman walked in and moved to her swiftly.

"Hi, I'm Jessica," the tall brunette said freezing Giada looking up into her eyes, instantly controlled. The woman had to be 6'1" tall, slender with definition, small breasts pushed tight against her body with the sports bra. "I'm Charlotte Weiger's temp."

The lean, confident woman looked Giada's body up and down, extending her hand which Giada took and shook.

"Good to meet you, I take it you will be at our meeting this afternoon at 2 p.m. with our team?" Giada asked, admiring Jessica's high cheek bones and perfect skin, she wore minimal make-up.

"See you there," she said and headed to the showers.

Giada was doing prep when she received a text from Charlotte.

"Conduct the meeting without underwear...trust me..."

"Shit, you've got to be kidding!" she texted back.

"Trust me...." the next text said.

There were 15 minutes before the meeting, Giada felt that nervous, scared, yet pleasurable sensation in her gut, looking around there was no time to think. She had wore a medium length skirt to just above the knees, that shouldn't be a problem. She looked again at the door of her office, people moving about just outside.

"Fuck it," Giada said, shimming her panties down and off, putting them in a top drawer of her desk. She moved to the bathroom, grabbing her cardigan and inside removed her bra, thankful it was chest day in her workout and her breasts were pulled up by her pecs. She dropped the sweater over her dark nipples, the light print of the dress showing them off some especially when erect like they were feeling the silkiness of the fabric against them without the bra.

Self-consciously she made her way to the room, the sweater wanting to slide some, the pointiess of her nipples could be seen if you looked for it, but that can happen through a shear bra. She hated to do it but buttoned two on the bottom of the sweater after moving into the hall so it would stay.

Giada started the meeting on time, Jessica was five minutes late from her workout and began taking notes. She was to report directly to Charlotte later that afternoon, and Giada efficiently worked the meeting to finish 15 minutes early.

"Jessica, stay back for a second would you," Giada said, the 10 or so people leaving and Jessica gathered her things and moved up to her superior.

"Yes Giada?" she asked, setting the pile of books and notebook down.

"I love working out, but I never let it...." Giada started her reprimand, Jessica standing tall and moving to her interrupting.

"Never button a cardigan," She said, her face about six inches from Giada's staring her deep in the eyes. "It just frame your torso, best if it is on each side of your breasts."

Giada breath was stolen while Jessica moved into her, having to lean down, whispering in her ear.

"I am Charlotte's temp in more ways than one," Jessica's hand moved to Giada's left breast, rolling the nipple between her thumb and forefinger. "So hard, yet supple your nipples."

Jessica moved in and pressed her lips to Giada's, her fingers spreading over Giada's breast, squeezing and pushing into her body.

"Congratulations Giada," Jessica whispered, again moving her mouth to Giada's ear. "If you keep your underwear off all day you'll have completed a level two challenge."

The tall woman bent some and slid her hand down and between Giada's legs, over the fabric, pressing into her pussy then back up. Jessica kissed her again and then disengaged from Giada who's eyes were closed and her body tingling.

Giada watched the shake of Jessica's ass in her skirt, black with the black suit coat, a rather handsome site.

"You have to do more than the minimum," Charlotte said to Giada who called immediately after kissing Jessica. "Yes I set it all up, I figured you'd want to score well and Jessica, well she's delicious. You have to get a picture of yourself sitting in your office chair from the waist up, then roll up your skirt and show your pussy baby. Oh, and don't forget to post it...I can't wait to get off to your shots."

"You'll have access to my stuff?" Giada giggle, liking the end of this assignment, her inner nudist coming out again. "I'll get a second workout in and come back, shit it's not like I have to tuck anything in."

"Oooo, kinda Britney school girl look please, tie your shirt at the bottom," Charlotte egged Giada on. "I don't have access yet, so friend me when you get these uploaded."

"Count on it. What am I supposed to do with Jessica?"

"Relax and let it come to you," Charlotte said.

"Why can't you tell me?" Giada asked in an impish tone, turned on by the woman on the other end orchestrating her please from a thousand miles away.

"Trust me..." Charlotte said again, giggling.

"I do," Giada said ending the call.

Giada did do her second workout in the office gym, and without changing walked upstairs to her office. She got naked in her bathroom, wearing just her white shirt and tying it like she was a school girl, undoing her hair tie, ruffling it messy, then hiked up her skirt, sat cross legged in her desk chair. She felt alive shooting the pussy shot, even throwing a breast out of the shirt shot into the mix, mixing in a Santa hat and a long, red Christmas scarf she had worn getting to work. Naked and playing in the office felt dirty and it moistened her cunt, making for a number of glistening shots.

Quickly Giada changed, just putting on her warmup pants and top she had in her bag for 'emergencies' and walked home. She eagerly uploaded her pictures, found Charlotte's email listing her username, pouring through her Lover's pictures and profiles, and "Friended" Charlotte. She masturbated to one of the many videos she had found on the site, The woman's beautiful body being tied up, she being spanked and while modeling for the camera. She wished she could see Charlotte, Danielle, even the boys tied up and spanked.

She slept well again, naked in her bed.

The rest of the first week and weekend was filled with work. Monday of week two of Secret Sadistic Santa or "Triple S", started with an important meeting and a new discovery.

She met with a city commissioner who was contacted by Mr. Donnovan's representatives to further solidify their position.

"Your information about the tax issues the Catrells have is good leverage, but I don't think the commission will push it through before this spring," John Janness said, district five commissioner. "And then a vote would not go well."

"Okay, its pretty simple John," Giada said aggressively, her blouse open as she leaned forward, his eyes darting there and back. "I've filled out the paperwork. It's going to be on the agenda. If you follow it up with a letter who's language strongly suggests you're ready to purse this AND the tax debt will be taken out of their compensatory reimbursement."

"And they'll be more likely to sell to you and keep fighting the tax battle in court," Janness said.

"I'll have a draft of that letter to you and send it along, so there's no work anyone has to do," Giada said, getting up from the table and walking to the 5'6" man, her strong body and curves, shrinking his presence.

"Yes...do that," he said and scurried out of the room.

She drafted the letter, called the other commissioners that morning, then got a workout in at the company gym. She was very comfortable there, only a few people milling about, she worked out in just a sports bra and volleyball sized shorts, the young clerk from the 1st floor looking at her a lot. She smiled at him a couple times, his brashness showing as he didn't back down, his looks more frequent, and longer in duration.

He walked over to her while getting a drink.

"Hi," he said, just looking directly into her eyes. "I'm sorry, I'm going to be way to forward. But I have to ask you if you're doing anything tonight? If not, I'd love to have dinner."

Giada smiled, looked down, thinking how to respond. "I am doing something tonight, ah...."

"Peter. Peter Joshelter" the young man said, not deterred. "Some other time then?"

"Perhaps," she said, moving past him and looking back. "I'll contact you.."

"Nice meeting you, ah...."

"Giada Lowder," she said, then to back him off some. "Soon to be partner.."

"Oh..." His disappointment palatable as it would be a violation for a partner to dip to far down in the employee pool.

"I said soon to be..."

Giada strutted away feeling electric, leaving him to his rising hard on alone. She couldn't believe her forwardness even letting him down, but it was week two and she had a date with a box. She called her oversexed brother walking home.

"You should have fucked him right there, Sissy. That's a boss line that needed a boss fucking a subordinate," Joey said, his childlike excitement at her telling of the story. "This leadership program is bringing you out of your shell."

"I don't like it, I mean, what it does to my head," Giada admitted to him. "I keep wondering who's doing what with whom..."

"Any theories who Master Rossfellow is?" Joey asked, Giada reading him all the notes and emails. She had gotten several, the last stating it was important she open her Level two note Sunday night - "The one you didn't do last week" acknowledging her encounter with Jessica and going without underwear at work.

"Follow me on this thinking and tell me if you think I'm right," Giada said. "It can't be my team, Danielle, Clete, Luis or Charlotte and it can't be anyone beneath us, right?"

"That would make sense," Joey said. "What if they hire it out?"

"Nah, too risky, it has to be someone who's been through it and is with the company," Giada said. "So that leaves Mr. Donnovan or..."

"The board of directors!" Joey said proudly, following her line of thinking. "Are any of them named Rossfellow?"

"That would be too easy, however there is a Guy Powers and guess who his wife is?"

"Jessica Powers! Your temp bi lover!" Joey yelled into the phone.

"Not quite yet, she only got to first and second base," Giada giggle. "And GUY POWERS looks like the Christmas caroler that delivered my box of challenges for Triple S."

"Interesting..." Joey said. "Good luck, and we got a crappy bowl bid that will delay me getting home until almost New Years."

"Awww, I was looking forward to review all of this in person," Giada said. "Luv you, bye!"

She regretted not taking the dinner invitation, but settled in and did Christmas cards the old fashioned way, though printing them out herself on her top of the line printer. She loved this process of reconnecting and would often get a phone calls back after writing 2-4 sentences of connected memories or recent encounters with them.

The music was the Vince Guaraldi Trio, and the music from a Charlie Brown Christmas, then one right after another, the "A Very Special Christmas" playlists.

It was 11 p.m., the lights of the city magical, she was naked under a robe having changed out an hour before that before finishing the last five cards. She tried to call Charlotte, going immediately to voicemail so she had her blocked again. Giada wasn't tired, she wasn't anxious, she was at peace. She read some from an old Christmas novel she routinely placed under the tree and her old time victorian cuckoo clock chirped midnight, 12 times and she thought about bed.

"Open the door...trust me," the text read from Charlotte, promptly coming through after the 12 chirps.

"Goddamn IT!" she texted back, her peacefulness turned anxious, the fear and nervousness, she cinched her robe up and walked down the steps.

There was a low level knock.

She took a deep breath and opened the door, her flat didn't have storm doors and the 6'3" handsome man walked straight in, Giada closed the door and turned to him.

"Master Rossfellow, good evening," she said and bowed her head.

"Your confidant said you were up and I was in the area and thought it best to begin your regimen this evening," Guy Powers, or Master Rossfellow said. "Is that okay with you, or should I leave."

"My level two challenge, the one your wife didn't tell me about?" Giada's smartass tone drawing his ire.

"My dear, that was a direct answer you need not respond in question back," Master said, her hand clenching and making a fist and opening.

For a moment she thought this was ridiculous, a strange man in her house and she should ask him to leave. She paused, looking forward at the floor, then up at him. She heard Charlotte's voice in her head saying 'trust me'.

"It is okay with me, Sir," Giada said, now not knowing what to do but doing it...

"Very good Child, you must address me as Sir, Master or Master Rossfellow," Master said. "That is point number one you must always remember, and you will address my wife, in non-business times, as Mistress, Mistress Jess or Madame."

"Not in business situations, right?" Giada said just asking a clarifying question, Master reaching out and slapping her across the right cheek.

"FUCK! OWWWW!" Giada screamed.

"Speak only when asked a question, or ask for permission and it is granted, though timing on the second part is important," Master said. "Point number two. What is point number one?"

"Address you only as Master, Master Rosefellow or Sir, sir..." Giada stopped, his look frozen for a moment. Then his hand whistled fast slapping her left cheek.

"SHIT! And your wife is Mistress, Mistress Jess or Madame," Giada said, the sting on both sides. "Ahhhh."

"Good, you're barely dressed," he saw her naked torso and her bush as the robe parted on the slap. His finger ran up the cloth of the robe and lifted it off her shoulder, dropping it to the floor. "Leave that here, Child."

He walked up the steps to her first floor, a long jacket on, she let the robe fall, feeling vulnerable now, naked, her flat's temperature programed to lower for late night, her nipples hard, her skin getting gooseflesh. The soothing Christmas jazz still played, the lights flickered and were set to go all night, the city looked calm out her window.

"You may call out the safe word 'bush' at any time, he looked down at her sweet little blonde, trimmed, bush and you may say 'stop' to discontinue any physical actions of this training," Master Rossfellow said turning and handing her his coat, she moved to hang it up, his hand shot and grabbed it and held her firm. "Point number three always, and I mean always, ask to do anything, even if it's implied except for what I teach you this evening."

"AHHHH!" she screamed, his slap came across her face much harder this time, she realizing what needed to be said. "May I hang your coat up, Sir?"

"Yes, Child." He said and sat down on her comfy chair, his long arms on the arm rests, he was dressed in a collared shirt, long sleeves, with a victorian stripped vest and stripped dark pants with black boots. His feet were firmly on the floor, the pose from the Jefferson monument. The playlists were still going, having run out they started playing randomly. "Kneel before me, back on your heels, arms at your side, head down, when I sit. I will have a pad or place for you if you are before me like this formally. If I'm standing you may stand, arms at your side, head down or do as you are doing now."

Giada had moved into that position, looking down at his boots then closing her eyes and listening.

"If I clap my hands twice, you must rise to your feet, your legs should spread past shoulder width, and be ready for inspection," he said and immediately clapped his hands twice. 'clap! clap!'

Giada shot up to her feet, her breasts bouncing, she felt his eyes on her while he rose up from the chair, she was careful not to look at him, she adjusted her weight back and forth spreading out, her wet pussy lips from the excitement this man's dominance brought her cool in the 66 degree air. She stared down as he walked around her, looking at her from each angle.

"Giada, you please your Master," he said to her, his hand now touching her shoulder, pinching her biceps and triceps. She was indeed a physical specimen and younger than Mistresses Jessica. "How long have you been in training?"

12