Secretly Sadistic Santa Ch. 01

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

"Child, I recommend you sit down," Mr. Donnovan said, but Giada was gone and out the door. He sipped on his drink, smiled and said to no one. "Perfect. She'll be crawling back soon."

The lights of the city decorated for Christmas blurred, the drinks somewhat dizzying, but it was the fact Charlotte had left and didn't answer her call. It was only Wednesday, of the first week of December, what her next move was to call Joey, her little brother.

"I've got to go watch film, what is it, fast Sissy," he said, the bustle of his roommates encouraging him to leave.

"Call me when you're done," she said, he was the only family member who supported her move and now she was thinking of quitting and crawling back to Mom and Dad's company. She ended the call and headed upstairs to her bedroom and started packing for a trip north. Giada tried to call Charlotte again, getting the voicemail again, this time leaving a message.

"Call me back, LOVER.." she said in a snotty way, the betrayal hurt. "I'm ready to resign and make sure I find a company to sink Donnovan, LLC! Call me BACK!!!"

She fell on the bed crying, and then she heard a soft knock on the door. It repeated a few times and she walked to the stairs. She then heard carolers singing.

"We wish you a Merry Christmas, We wish you a Merry Christmas. We wish...." They continued and Giada moved down the stairs. She loved carolers and caroling, she had sang with choirs at school, church and in college. Opening the door and smiled seeing four college aged young people, two women, two men, singing with the books open. "Good tidings we bring to you and your king, We wish you a Merry Christmas and a Happy New Year."

Giada clapped when they wrapped up, and noticed a giving can. They started Silent Night and she left the door open and rush back, got a $20 out and put it in the can. She sang along, joining the sopranos remembering her days in competition at college events. Her heart leapt with joy, and when they ended, they all clapped, they turned to leave.

"Merry Christmas," a sharp looking young man said, handing her a present the size of a microwave box. "Open it later tonight."

Her smile left, she watched them go down the street and knock on another door and begin caroling for an older couple. Giada pivoted, went inside and set the box on the seat it read "To: Ms. Lowder From: Your Secret Sadist Santa"

"Fuck..." she said aloud, looking upstairs at her room, her packed bag waiting for her to flee, then down at the box. "Fuck this."

She ran upstairs, grabbed her bag and was heading down her outdoor steps when her phone rang.

"Giada, go back inside," Charlotte's voice said. "Open the present, trust me."

"So you just came on to me to..."

"No!" Charlotte said. "I wanted you for myself and, well, that can't happen...not yet anyway."

"What are you talking about???!"

"I can't explain much more, I've already..well I'm about to board a plane," Charlotte said frantically. "I'll see you by Christmas, just open the fucking box before you do anything!"

Giada stared at her phone after Charlotte ended the call. Her car for in the lot just a block down. She wasn't clear about anything, and when that happens she either called her brother, who couldn't talk, or worked out.

Stubborn, she ran past the present to her Peleton bike downstairs. She hadn't used it in a while, choosing the HIIT workouts with her dumbbell and kettle balls. She joined a workout in progress with her favorite rider, and young hispanic woman who's shaped was alluring, and her attitude 10 times that.

"Oh, I see Giada decided to join us after a while, and late!" Camilla said laughing and continuing the workout. Giada got into it and it was like riding a bike, though her wind at first was difficult, but 15 minutes in she was her old self.

Giada waved goodbye at the instructor and the 15 people in the class, turned it off and the phone rang. It was Joey.

She filled her brother in on everything, Charlotte included since he was the only one in the family that knew she had feelings for women as well as men.

"You are so brilliant and open to learning about everything except sex!" Joey said, giving her the opposite of what she wanted. "This is about Leadership and how to accept someone else's leadership. Trust it and if that's all it takes to be Partner???"

"Geez, you're all against me," she said, feeling like she was the only one in the world pent up about sex. She then asked about his love life, getting the usual 'it comes and goes' Joey never letting her in like she lets him in the conversation.

He had to go and Giada went and fixed a light dinner, then sat down with some tea looking over the river, loving where she landed, loving everything except what the box represented. She had been duped she felt, then began to think about being 'submissive', she even reflected on the sex she and her husband (now gay) had, she felt like she was just there most of that time not submissive, but he certainly wasn't dominant. Charlotte was dominant to her, telling her, guiding her, lusting for her.

"Open it, for me...just look inside," a text from Charlotte read. "This is the last you'll hear from me until Christmas."

Giada tried to call and text and she was blocked.

"God Damn it!" the 31 year old, potential partner of the biggest real estate firm in the Central United States. "Alright Charlotte! Alright, you win!!!"

She walked slowly to the present, bringing it up to her island, noticing the victorian wrapping paper with muted reds, golds and silver, lined with black edging. The bow was immaculate and proportionally hand tied and applied to wrap around all four sides of the package. Someone knew her, really dug into her love of everything Christmas, ornate and victorian.

Giada wanted to leave it under the tree, the soft and frilly, lots of holly berries, garland and birch looking trees with white, creamy lights. Her home was immaculate in it's homage to everything Christmas, older looking Santas, a nativity that was hand carved and painted to show the faces.

In her mind opening the box would spoil the mood, the aura she had intently created, soft candles in the window, their LED lights flickering, casting moving shadows. She called out and said, "Alexis, play Christmas 2023 playlist" and the Vince Gill version of "Breath of Heaven" began. His voice was haunting and sultry, gravely and pure.

The chorus came on and she slid a finger under the ribbon, sliding it softly between it and the expensive wrapping paper she was sure as shit going to save. She found the weak point, lifted and popped the tape that was expertly hidden, unraveling the beauty that gave the box ornate stature. Vince's voice began to rise and fall with the middle of the song, her finger sliding to the ends where the paper was folded and adhered with hidden tape again, popping both sides, finding the end under the package and popping off the the tape there. Soon the wooden box, the size of an average microwave, sat on the table, the paper draped over it, Giada melting into the crescendo from low to high volume of Vince's voice taking her away.

The song ended and her eyes opened.

The sultry voice of Ariana Grande came in with Santa Tell me, her girl celebrity crush, just realizing she liked Charlotte due to her smallish breasts just like Ariana. Giada, in that moment, decided to open the box, at least look at what's inside, what Charlotte wanted her to see so badly.

To her left was her wine rack, she opened a screw top, grabbing a glass and pouring it half full, taking a nice gulp of the dry red. She turned and pulled the wrapping up and folded it carefully, she was singing a little with Ariana, imagining her petite little frame, Giada's hands on her small shoulders.

"Okay, let's do this," Giada said to no one, setting her wine down and running her hands over the smooth, expensive wooden box. She released the small, gold, hook-latch on the front and opened the box. On top of foam that was covering the bottom and the top halves of the box was an envelope, that was addressed to "Mon Amour..." or 'My Love' in french.

The playlist magic continued on random surfacing "Christmas Time" by Ashanti, the mood perfect while Giada opened the letter and began to read, her heart racing now.

"Giada:

I have fallen for you in a short amount of time. My world is diverse, not conventional; different, in ways you should experience.

I recruited you, knowing it was risky, that a tame bird in the wild may not survive, though your skills are many and your confidence for Love should be a great as your confidence in real estate.

Your attitude, body, eyes, hair, curves, soft places, are all meant to be shared, your mere presence tantalizes everyone's imagination to the rest beneath your clothes; the rest in your bed.

You can use this activity as a window to my world; a step forward into it, or a cannon ball into the many physical, and cerebral delicacies that will both pleasure, punish and addict you through your nerve endings and synapses in your brain.

There are four levels and you can participate at the introductory for three of the four weeks, you must try one third level experience out of the four and you can do that any time before Christmas. Also, you may choose more than one experience each week.

You can easily do this and I can then say my girlfriend is partner in the company.

Ton Amour (Your Love)

Charlotte"

"Damn it!" Giada said, tears running down her face. "God Fucking DAMN IT!"

Her hands were shaking pulling the foam off the bottom layer. There were cardboard boxes embedded in foam underneath with a number on them. There was a small instructions sheet laying there.

"Child:

There are multiple boxes to choose, do as follows. Select from 1-3 for week one; 4 or 5 week two and 6 or 7, week three. Follow the instructions with each box and be sure to document

Your Secret Sadist Santa Master Rossfellow"

"Document?" She said to herself

Giada looked down, there were seven boxes with the listed number. Without hesitation she grabbed the number 2, opened it, a rolled up strap from a horse bridal fell out along with a note.

"Video yourself in front of your Christmas tree doubling up this bridal strap and whipping your back side 20 times hard enough that you cry out. You'll end up doing more than 20, so count only the ones you physically, naturally, cry out in pain.

Create a FetLife profile and upload a still shot from the video to your profile pic, fill out your profile and then upload the video. You will be told who to share it too later this week for verification, and that will be the only person you HAVE to share it with, though you can share it to whomever.

Once done, your are finished with week one. You can choose to do more than one document it by uploading a video and you'll be recognized for your participation, regardless, at the Christmas party Dec. 24th at noon."

"Seriously?" she said, an Elton John song was on, she looked around, her shades were draw enough on the street side and the tree covered the window. Truthfully she thought this was an easy entry into week one, she often was in pain working out and maybe this was similar. Videoing and uploading was scary, she figured it was private as long as you didn't make it totally available, while wondering how much she could trust this group.

She emptied, filled her drink glass, figuring she may need some liquid courage for the videoing and to help power the strap to her naked backside. Walking around her apartment she made sure the blinds were shut and no one could look inside.

Setting the glass down, she slipped off her sports bra and racer back, stood topless in her front room for the first time running her hands over her breasts, then shimmied out of her yoga pants, and was nude.

She walked upstairs to her bedroom, the window not a problem since it faced the river, grabbing her selfie light, the circular illumination would flatter her fine physique. It was charged so she skipped down the stairs, chuckling thinking had she tripped the EMTs or coroner would have a naked sight to behold.

"Ah, U2..." Giada sighed when 'Baby Please Come Home' came on.

Centering her iPhone in the the light, the latest greatest, they claimed you can shoot a major motion picture upon, set it to video and lined up the Christmas tree approximating where she would be, sideways thinking she'd turn giving the audience looks from all sides every 5-10 strikes.

She had to admit to herself she felt alive, excited and titillated naked and soon to be in front of a live video recording. She shot a sex "tape" on her phone late in their marriage in an attempt to match his horny nature, but he took it further wanting to fuck on a live webcam stream. The first was fun and she had enjoyed whenever she skinny dipped (back in the day) or just walked around the house naked.

She was comfortable.

"Okay, let's give this a try..." Giada said to the air, holding the bridal strap doubled up, waving it front to back, getting a sense of where she had to make contact. She snapped it lightly, swinging then flicked the wrist harder.

"Swap..." it landed on her cheek harder than she expected.

"Damn!" she cried out, surprised how easy it was to snap her wrist to get momentum changed and speed up the end of the strap. She continued to swing it to and fro and snapped it again, this time it hit on the tip. "AHHH! SHit!"

She dropped the bridal, moved to the camera, adjusted the light and started her video. Moving into position, she felt the eyes of the world on her picking up the leather, long and ornate device for pain. It was very victorian she thought to herself, and began to give a show, holding it to her cheek, mouth and running it down between her breasts, then legs.

Her eyes were half closed, looked at the camera, and then began waving it around side to side, her first attempt catching her thigh going back, throwing off the timing and smacking her ass, she gave out just an "Ohhh..."

Unfazed she waved it back and forth again, unwittingly faster and snapped it back and "SMACK!"

"OHHH!!!!" she wailed, then began her count..."One."

Next song up was "Baby it's cold Outside", Giada racked up four strikes in six swings.

"Ah! Oh! Mmmm...AHHH!...Mmmmm...SHIT! AH!" she cried out then. "Up to Five."

She turned to the other side, her breasts dangling and swaying with the strikes, the song changing to a bluesy, "Run Run Rudolph".

"AHGGH! Six! OHHH!! Seven! Mmmmm, Mmmmm, AHGGG! Eight!" she was getting good switching to the other cheek, the right one getting red. "OHHH! FUCK! Nine! TEN!"

She stopped, the last one stinging hard. She showed the camera her red ass, forgetting that she ever had issue with this activity. She squatted showing her pussy, still some blonde bush trimmed from the night before, sliding her finger down and playing with her clit, wondering who would be watching, wondering who she could have peak in on her freakness.

She turned her ass to the camera and rattled off 10 shots in 15 tries, one right after the other, harder than any of them, having gotten used to the throb, the pain, the bright light of the internet pushing her to make herself yelp.

"AGGH! Eleven! MMFFFTT! Twelve! MMmm..MMMmm....AHHH! Thirteen! FUCKKK! Fourteen! MMmmm....Mmmmmm...SHIT! FUCK! AHHHH! That's seventeen! Mmmmm....OHHH!!! Eighteen! OMMMPFFFTT! Nineteen! AGGGGFFTTT! Twenty! FUCK!" she yelped and yelled, her red ass showing the camera her handy work.

It was 11 p.m. and she dimmed the internet light, walked upstairs and passed out naked, no tooth brushing, the alcohol and the strain of the beating at her own hands put her to sleep.

She woke energized, the slight headache the wine had, not as bad as a gin headache the other night, but there while she did her circuit in her basement. She was vain about working out, liking having some makeup on at work, though the workout facility there was amazing. She thought she might get a second one in later this afternoon, finishing a hard, self-designed, HIIT workout.

Cooling off she went upstairs and access the video of her escapades with the bridal strap, it lay in the middle of the floor of her living room, her lighting circle and empty wine glass. She popped a k-cup in and drank her water while waiting for the coffee to brew. She sat cross-legged on a comfy chair, facing the Christmas tree, telling her phone to put on "A Jazz Christmas".

The air filled with soft Christian jazz performances without words of the hymns she was familiar with growing up. Retrieving her coffee and sitting back down she smiled at how the lighting made the tone of her legs, arms, and the curve of her breasts look. She enjoyed the juxtaposition of the O' Holy Night against the sound of her wailing while the leather hit her flesh. She cropped out the beginning and the end, otherwise leaving the 20 minute video go, including some of her set up.

Next Giada accessed FetLife, then remembered she had to set up an email first, finding an off-brand carrier that promised increased security (and it rated highly on her internet rating site). She set up a profile and had took a screen shot of her in her squatted position, showing her pussy and breasts, looking demonically into the camera.

Giada didn't mess around, when she decided to do go all in on this activity she wants do win, do it better than anyone else..

She started uploading the video, it lagged some surprisingly, and in waiting filled out each square of the profile. It finished and she headed for the shower pleased she was done with week one, but wondered about the other level one challenges. She was somewhat excited from watching herself on the video and uploading it to a website that she had her profile private but what going to share it with someone soon.

The water was warm and her stomach surged with lustful desire, she slid her hand down and felt excitement in her pussy lips, having just came on Charlotte's hand a couple days prior. She thought of her, seeing her in her underwear in the living room, getting spanked. She slipped a finger inside, the jazz still playing having brought the speaker with her, O Come all Ye Faithful, she thought of cumming.

"Ohhhh Charlotte," Giada breathed, not speaking her pleasure to life in the conference room. "OHHHH!"

Her fingers batted her clit and slid inside, one finger, then two, then three, pushing inside and over her clit, searching for the spot then....

"OH YES! GOD YES! CHARLOTTE!" she orgasmed to her name loud, the music and water absorbing and blending with Giada's breath and moans. "Ohhh...."

"Two orgasms in three days, not bad for a dried up old lady," Giada laughed on the phone talking to Joey, the sex talk common place with them years ago, rekindled when he asked if she was gong to do Triple S or not. "Gotta go, coming up on the building, see you around Christmas.'

(To be continued)

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymous4 months ago

Well it’s definitely different. Not sure I’d be on board looking at it all from her perspective. She wants to explore things with Charlotte not someone else, it’s an aggressive tactic tbh especially considering that it’s all new to her.

Very interesting though, thanks

Tess (uk)

Share this Story

READ MORE OF THIS SERIES

Similar Stories

I'll Do It I offer to be a whore for my friend and her bf.in BDSM
Jogging in the Wrong Neighborhood Debbi jogs into the wrong neighborhood.in NonConsent/Reluctance
Jägersmuth Pt. 01 Georgia follows the girls on an unusual countryside retreat.in NonConsent/Reluctance
One Stubborn Arsed Lass! A stubborn lass is in hot water at work with her boss.in BDSM
Subconscious Self-Examination A journalist discovers the world of BDSM first-hand.in BDSM
More Stories