Ashley's Christmas SurpriseStory by Canadian_OutlawPosted 12/25/22 1681 views
It was a beautiful warm sunny day as Jason woke up and was excited to see how the office Christmas party was going to go. After Jason and Ashley had gotten together there a couple weeks ago they were basically inseparable at least virtually. They were messaging each other every day and Ashley certainly had fun sending him different pictures teasing him. He always had to be careful opening her messages at work as he could never be sure what she was sending him. She had also completely embraced WAM and she kept saying she had something planned for the Christmas party.
He smiles as he reaches for his phone and sends her his usual good morning text. "Good morning beautiful, how are you doing babe?" He types out before sending it to her. She quickly responds to him. "Thanks sweetheart, good morning to you as well. Honestly not too good honey. You know how I'm on the Health and Wellness committee? Well apparently they didn't select anyone to play in the trivia contest against the planned loser who will be humiliated. I don't know what we're going to do?" She replies and Jason could sense her stress and anxiety through her message.
"Oh that's odd that's normally handled weeks in advance? What exactly would that person have to do for the game?" He asks, wondering if he could help her out. She quickly replies to his message. "Oh it's just a trivia competition, the other person has been instructed to give wrong answers so whoever we got wouldn't have to worry about anything." She texts back and Jason starts wondering if she's up to something. He thinks it over and wonders if he should volunteer. He knew about the planned loser as it was something they did every year after the cake incident.
About 5 years ago a woman by the name of Isabella lost and had their face shoved in a cake. She ended up suing the company as her shirt got stained and it ruined her $3,000 blouse. This had been a tradition for years at the Christmas party so he wondered why she wore such an expensive article of clothing. Since then the company required the committee to select a loser in advance and have them sign a waiver on being humiliated but it was always a secret as to who was selected.
He thinks it over as he makes himself breakfast and he makes his decision. He picks up his phone and texts her. "So listen I've been thinking, if you are still looking for someone to participate in the game/entertainment part of the party I'll do it so you don't have to worry about it." She responded almost immediately, thanking Jason and telling him he wouldn't regret it.
The party wasn't far from where he lived so he decided to walk there on this beautiful Saturday late afternoon. On his way there he was walking past a coffee shop and decided to stop for a coffee. While in the coffee shop he happened to overhear a couple of his coworkers talking. "Can you imagine she agreed to all of this. Does Jason know, I mean I feel like someone should tell him if he doesn't know where he'll be the one humiliating her." He heard as he got his coffee This made Jason's eyebrow raise slightly. He turns to see his manager Carrie shake her head.
Carrie had always seemed to take a special interest in Jason and he could never quite figure out why. That was until he met Ashley. She ended up spilling the beans that she and Carrie played together frequently and Carrie had a crush on Jason. Ashley had even teased Jason about them maybe doing a threeway with Carrie, but he had always thought that was just idle teasing.
"Ashley said for. . . " Carrie freezes as she sees Jason looking at her. Jason quickly takes in her long blonde hair which looks like it had just been styled and her skin tight green velvet dress hugging her slim body and barely holding in her double D's. "Ashley said what exactly?" He asks in a confused tone. She shakes her head as she tries to think of something to say. "Ah you know I umm . . . I forgot Jason . . . I would umm . . . just don't worry about it. Trust me, have I ever led you wrong?" She says, stammering trying to cover something up.
He looks at her, narrowing his gaze slightly before turning to walk away. He then turns back to look at his manager. "Who am I humiliating anyway? Can you at least tell me that?" Carrie just shakes her head. "You know Jason, that is kept a surprise till the actual game. It's not you so don't worry about it." She says with a smile and he sighs before walking away.
Jason continues to walk to the Christmas party and upon arrival is greeted by Ashley who walks up to him in a sexy Mrs. Claus dress that compliments her slim petite figure. "Hey gorgeous you look amazing." He says with a smile giving her a warm embrace before giving her a kiss.
"Thanks babe, so I thought I would give you the details of how the game is going to work." She replies with a smile. "So Carrie is going to call you up first and ask you ten questions related to the holidays in some form or fashion and then we're going to move you over to our "isolation booth"." She says before pointing to a crudely made booth with some PVC pipe and curtains. "Then the second person will be called up and asked 10 different questions. Assuming all goes to plan you'll be the winner and administer the humiliation to the loser."
He nods slowly looking at her. "Ok then that sounds good. By the way, who is the person being humiliated?" He asks out of curiosity. "Don't worry you'll find out soon enough." She quickly replies, giving him her trademark disarming smile. He nods and decides not to worry about it.
Soon it came time for the game and Carrie called him up. He smiles as he walks up to the front of the room and sits down in the hot seat. "Are you ready Jason?" She asks with a smile and he nods. "Yeah let's do this." He replies.
Carrie then looks at her cards. "Alright then so your first question is, on the 1981 album "Christmas Wishes" by Anne Murray what is the fourth song?" Jason blinks a couple times as if in shock. Not only did Jason know the answer, he owned this specific album on vinyl. "Uhh that would be "I'll Be Home for Christmas." He replies with a smile.
Carrie smiles and nods. "That is correct." The rest of the questions continue in a similar fashion asking Jason questions about stuff he owned or knew very well from watching it every year. Then Jason makes his way to the isolation booth. They said there were noise canceling headphones in the booth but in fact there was not. Once they close the curtain on the isolation booth he hears someone else walk to the front of the room.
Then in the dark booth he hears Carrie say. "Alright contestant number 2 are you ready?" Whoever contestant 2 must've been must have nodded as he then heard Carrie ask them. "In 1992's A Muppet's Christmas Carol who played the role of Charles Dickens." In the dark booth Jason eye's go as wide as saucers as he hears Ashley say "Oh you know . . . I don't know, that's a hard one . . . Umm Fozzy Bear?" She replies, almost questioning herself. Jason had to resist the urge not to scream out the correct answer but soon Carrie says. "No, that's incorrect." It was at this point Jason realized what Ashley had done but there was nothing he could do about it. While he enjoyed getting Ashley messy he hadn't planned on publicly humiliating her so soon. Once Ashley had answered all of her questions, Carrie opened up the door to the isolation booth and Jason walked out.
"Alright then with a score of 10 to 2. Jason, you are the winner." Carrie says with a smile as he looks at Ashley and shakes his head while shaking her hand. "So Jason, Ashley, will you please follow me?" Jason and Ashley do so and Carrie leads them over to a kiddie pool and Carrie uncovers a table full of messy items including some holiday themed items. "Jason, you have 10 minutes to make a complete mess out of Ashley. Do you have any last words Ashley?"
She smiles as she looks at Jason. "Well I hope you don't humiliate me too badly." She says with a little wink. He sticks his tongue hard in his cheek and shakes his head. "I guess we'll see what happens." He replies as he gestures toward the chair. She nods and leans in to steal a kiss before taking her seat. The crowd starts yelling out suggestions but Jason doesn't pay too much attention to them at first. He spies a large bucket of eggnog and picks it up.
"Ashley, you look a little thirsty." He teases before slowly pouring the thick creamy eggnog over her head and proceeds to cascade down her body. The crowd watches in delight as she squirms in her seat trying not to moan till he pulls open the top of her dress and dumps the rest down inside her dress.
"Fuck, you pervert." She says almost teasingly trying to egg him on. "I can't believe you would do this to such a gorgeous girl like me." She groans and he chuckles.
"Guess you should've done better in the trivia." He teases back before taking a pumpkin pie that was covered in whip cream and smashing it in her face. She holds her hands up acting as if she's completely shocked as the crowd roars with laughter and asks for more. She wipes her eyes clean only for him to have already come around behind her and smash two banana cream pies on her petite breasts.
She groans and moans. "Fuck I'm filthy please no more." She begs and he smirks looking at her.
"What do you all think? Should we cut her a break?" He asks, teasing the audience as they cheer loudly. He chuckles as he smashes another chocolate cream pie in her face. "
She groans and moans more as he looks over everything and spots a nasty looking bucket of green slime and picks it up. He slowly walks over to her and then he begins to pour the thick chunky slime over her. She moans out almost lustfully "Fuck, I'm such a disgusting mess. Please stop." She begs before feeling the slime hit her and she looks straight up.
She squirms as she tries to avoid the slime and he covers her in the slime. She wipes her eyes clean and looks at herself. "My cute Christmas dress is ruined. You're going to pay for this." She whines as Jason chuckles. He then helps her to stand up to only turn her around and bends her over her dress barely covering her ass. He chuckles as he grabs a whip cream pie. "Please no, don't pie my ass." She begs as she wiggles it and the crowd cheers and hollers for more.
He chuckles as he smashes the pies on her ass sending whip cream splattering everywhere. "Oh wait, you said you didn't want me to pie your ass." He teases before quickly doing it again as if he was spanking her with pies. "You jerk, I can't believe you're doing this to me." She whines.
He smirks as he lifts up the dress and pulls open her panties as he fills them with the whip cream filling them up with cans of whip cream. He then does the same to the front of her panties before rubbing it in and she moans loudly. "Oh you fucking asshole." She moans out. Jason chuckles looking at Ashley before turning to look at the cart.
Suddenly another girl interrupts Jason by the name of Sarah. "I'm sorry to interrupt you but there is something you need to know." Jason looks confused as Sarah hands him some papers while Carrie stands to the side visibly nervous about something. Jason reads over the papers and then looks at Sarah. "Is this for real?!?!?" He asks in a state of confusion looking at Sarah. She nods her head and then he looks at Carrie. "Should I tell them or do you want to?" He asks, looking at her.
Carrie nervously smiles and shrugs looking at Jason. "I . . . uh . . . I don't know . . . what you're talking about." She says nervously. He smirks then nods while holding up the papers. "Well Carrie seems like there was a stipulation in place that I was just made aware of." He replies as she nervously takes a gulp. Jason turns to read the papers. "If any contestant gets all 10 questions right they may choose to also humiliate the host along with the losing party." Jason reads aloud before looking over at Carrie.
"I mean you . . . you wouldn't do that to me!?!?! Would you?" Carrie states nervously as she tries to back away. "I mean I think everyone knows I wouldn't have knowingly volunteered to humiliate Ashley and when I asked you earlier today what Ashley had said I believe your exact words were "don't worry about it." and then you added that up with "Trust me' have I ever led you wrong?" He says with a smirk as he closes in on her with a loud cheer from the audience.
Carrie gulps and nods as she extends her hand towards Jason. "I . . . I did say that . . . I guess it's time for me to get my comeuppance." She says softly admitting defeat as Jason leads her to the pool to join Ashley. While he walks her over to the pool Carrie whispers in Jason's ear. "Do you think there is room for the three of us to play at your place after this?" He nods and smiles looking at her.
He smiles as he helps Carrie into the chair and Ashley chuckles. "Oh looks like I have someone to play with." Ashley teases as she leans in and gives Carrie a messy passionate kiss while Carrie squirms as she does. As Ashley kisses Carrie Jason grabs another bucket of eggnog and begins to pour the thick creamy eggnog over them and covers them both and finds its way between Carrie's breasts causing her to shriek from the cold.
Ashley cackles as she begins to rub the eggnog in on Carrie while Jason grabs another pumpkin pie covered in whip cream. Carrie not paying attention has her eyes closed as Jason approaches and smashes the pie in her face. "Oh fuck, Jason I'm going to get you for this." She shouts as she cleans her eyes and he chuckles.
"Oh I'm sorry, would you prefer chocolate?" He teases as he grabs two chocolate cream pies and walks over to her, giving her a pie sandwich. Ashley chuckles as she leans in and licks some of the mess off of Carrie's face. "Mmm you taste good Carrie. Jason you should get a taste." He chuckles. "Oh I will later." He teases.
Jason smirks as he grabs a bucket of custard as Carrie and Ashley begin to makeout. He then walks over to them and begins to pour the custard over them as they kiss each other passionately. He lifts the bucket up and slowly pours the custard over them and covers them with custard. Then he gets Carrie to stand up and turn around showing her clean ass on her dress.
Ashley smirks as he walks over to Carrie with a large whip cream pie and smashes it on her ass. Then he quickly follows it up with two more. He then sneaks a peak to see she is wearing granny panties and gets a smirk on his face. "No please . . . please don't fill them with anything" Carrie begs as he gets an evil grin on his face walking over to a large bowl of chocolate mousse.
"You really should learn not to tell me not to do something." He teases as he dumps the mousse into the back of her panties as she lets out a loud moan. "You fucking dick!" She shouts as he laughs with the crowd before turning her around and filling the front of them. As he turns to grabs some slime Ashley makes out with Carrie pushing her back onto the seat sending some of the mousse squeezing out of her panties.
He approaches them one last time as he begins to cover them in red and green slime. Once he's done he looks at them both breathing heavy and Carrie beckons him in close to them. "I think I can speak for Ashley and I. We need to get to your place so we can have your dick." She whispers and he smirks and nods. "Sure but you're both walking there like this." He teases and she nods quickly. "That's fine by me." They both nearly shout at him. He chuckles and nods, giving them a towel to clean their eyes before leading them out of the party to his place.