Halloween Challenges!

Cindy and Jason both work at a large company together. Their paths cross some but not a ton. Jason is good friends with Cindy's boss, Sam.

"Is Sam in today?" Jason asked Cindy as he walked up to her desk.

Cindy is an administrative assistant. She is in her late thirties. She is a blonde with an athletic, tone body, Sam is a Vice President of finance for a large company. Jason works in their investment division two floors up. Jason is in his late thirties and is very fit as well.

"Yes he is. I will let him know you are here." Cindy replied.

"Thank you, Cindy!" Jason responded.

Jason and Sam have been coworkers and friends for about fifteen years. The get along great. They both have worked their way up in the company and are both doing well.

"Come on in?" Sam yelled to Jason. "Please shut the door on your way in."

"It looks like you are working way to hard for a Friday afternoon!" Jason told Sam.

"I couldn't agree more." Sam replied.

"The merger is over, time to relax a little. Leave early for the weekend!" Jason joked. Their company just completed a larger merger that had everyone working extra hours.

"I wish I could." Sam said sitting in his desk looking exhausted.

"What's got you all stressed?" Jason asked while taking a seat.

"HR stuff." Sam said in a lower voice.

"HR? That sucks? Anything going on?" Jason asked.

"It's Cindy." Sam said in a low voice, trying to speak so she could not hear.

"Cindy? Really? What's going on with her?" Jason asked.

Cindy is the role model employee. She is always on time. She always works late if asked or needed. She is very good at her job. It was out of the ordinary for any issues to be going on with her.

"Yes, I know. That's what I thought when they called me to discuss a situation with her." Sam said.

"Did she do something wrong?" Jason asked.

"You know I am not supposed to be talking to anyone about this, but, yes she got herself in some trouble." Sam said.

"Come on man, what did she do? Whatever it is, you know you can take care of it for her. She is a rockstar. You need her. And if you don't, I'll hire her and pay her more than you are!" Jason joked.

"Of course I'm taking care of it. It's just that I still have to discuss the situation with her. It's not an easy one to discuss." Sam said.

"Man, what did she do?" Jason asked leaning forward getting closer to Sam.

"This has to stay between us, okay? HR caught her looking at porn on her computer." Sam said.

"Porn? No way." Jason said shocked.

"I thought the same thing." Sam said.

"Cindy doesn't seem like the porn type. I mean, she is like a super mom. What does she have, like three kids. She's married. She is the definition of super mom." Jason said shaking his head in disbelief.

"Well, maybe that was the old Cindy. The new Cindy is now getting a divorce." Sam said.

"No way. She's getting divorced?" Jason asked.

"Jason, you have been up on that fourth floor too long. That merger kept you busy. You haven't been down here to say hi in a while. Yes, Tom was cheating on her with the eighteen-year-old babysitter." Sam replied.

"No way!" Jason said in shock. Tom is Cindy's husband or, now soon to be, ex-husband.

"Yes, she went home for lunch one afternoon and walked in on them during her lunch break." Sam told him.

"Oh fuck." Jason said in shock.

"Cindy's entire world has been turned upside down. She started dating Tom when she was fourteen or something close to that. They went on to be high school sweethearts, and they get married. They have been married almost twenty years." Sam said.

"When did all this happen?" Jason asked.

"About a year ago!" Sam answered.

"A year, no way. How come I haven't heard about this?" Jason asked.

"Man, that merger had us all running crazy around here. There wasn't much free time for chit chat." Sam said.

"So, how is she doing?" Jason asked.

"At first, bad. The first six months were rough." Sam said.

"What about now?" Jason asked.

"Well, now, I would say she is going through some, how should I say this, life changes. At least that's what I have picked up on." Sam said.

"Picked up on? What all are you picking up on?" Jason asked.

"I think she is going through a wild phase or something. Maybe a midlife crisis." Sam said.

"Really? What makes you say this?" Jason asked.

"Well, did you see her when you came to my office?" Sam asked.

"Yes? I'm not sure what you mean." Jason asked confused.

"Did you see her skirt?" Sam asked.

"Skirt, no, she was sitting at her desk." Jason answered.

"Hold on. Let me see if she can come in here." Sam said while picking up his office phone.

"Cindy, could you bring me a copy of last year's fourth quarter expense numbers." Sam said talking to her on the phone.

After a few moments Cindy walked in to Sam's office with the report. She was wearing a light blue dress top and a black skirt. Her skirt was tight and short. She had on black heels and black pantyhose under her skirt. Both Jason and Sam watched as she dropped off the report.

"Anything else I can get you?" Cindy asked.

"I think we are good. Thank you, Cindy." Sam replied.

"See what I'm talking about?" Sam said after Cindy left the room.

"Holy shit. Fuck, she is looking hot! I mean, she was always attractive, but wow. I guess I never really noticed her like that before." Jason said.

"About a month ago she wore her first short skirt. Dean, from marketing, was here almost ten times that day talking to her. I think she enjoyed the attention. I think a lot of men didn't notice her before." Sam said.

"Dean? Isn't he married?" Jason asked.

"Yes. Oh, nothing happened, he was just up here flirting with her. At least I don't think anything happened." Sam said. "Last week, she was supposed to have a date. It was with some guy she met online. She said she was excited about it. You should have seen the dress she wore that day. Wow."

"Really, so she got all dressed up for her date, huh?" Jason asked.

"Yes. I guess they were supposed to meet after work. The next day she was super down. The guy stood her up. I felt bad for her." Sam said.

"That sucks. That guys loss though." Jason said.

"Yes. Now I have to address this porn thing with her." Sam said.

"That's not going to be easy." Jason commented.

"I know. I'm a happily married man. Most men would love to be talking porn with a woman like her. This is going to be awkward." Sam said.

"Oh, poor you. Ha. You want me to talk to her about it?" Jason joked.

"No, that wouldn't be a good idea." Sam said.

"What kind of porn was she looking at?" Jason asked.

"Well, it wasn't exactly what you would think. It was a website with erotic stories. So it wasn't like she was just watching videos or something." Sam explained.

"Well, that's not that bad." Jason said.

"No, but HR said the website was pulled up from early morning through the end of the day. I'm guessing she pulled it up and got busy and forgot about it or maybe she just looked at a little at a time. I don't know. There's a good number of people who come down this hallway to my office. Anyone could have seen it pulled up. Delivery guys, any number of people. That's more of an issue than anything. I just don't want someone to see it pulled up on her screen and assume things. That wouldn't be good." Sam said.

"You think anyone saw?" Jason asked.

"I'm not sure." Sam answered.

"What type of stories?" Jason asked. "I mean, was it a specific type of erotic website?"

"According to HR, it was something called 'Literotica' and the stories were CNC and blackmail type sexual stories." Sam said.

"CNC?" Jason asked.

"I googled it. It stands for consensual non consensual." Sam said.

"Dang, Cindy is getting kinda kinky. She is going big for her midlife crisis." Jason commented.

"Yeah, I'm not going to bring those specifics up. But please, you know this stays between us." Sam said.

"Of course. Man, that's a hard conversation you have to have with her. Well, I'll let you get to it. Good luck!" Jason said.

Jason stopped on his way out and talked with Cindy for a moment or two. He noticed how much more Cindy was flirting. He also noticed how short her skirt was when she sat down. Cindy made sure to push back in her chair, so she could let him see. They had always flirted but nothing like this. She was much more sexual. It's like she knew he could almost see up her skirt, and she teased him by moving around in her chair. Cindy had always had a crush on Jason but was to shy to flirt.

Jason left and thought about Cindy for the next hour. Consensual non consensual kept coming to his mind. Finally, he decided he was going to act. He wasn't sure what he was going to do, but he knew he was going to do something.

Jason decided to send Cindy an anonymous email. He thought he would flirt a little and see where things go. He created an anonymous email account and sent her an email on her work email.

"Hi Cindy. I just wanted to send you and email saying how gorgeous you look today!" Jason typed in his email.

"Okay, I guess thank you. I appreciate the compliment. Who are you?" Cindy responded. She was flattered and curious about who was flirting with her.

"I'm just an admirer!" Jason emailed back.

"Well, thank you again, Mr. Admirer. I enjoy dressing up. I'm glad someone noticed. I wish I knew who you are though." Cindy replied.

"I have been over your way a few times in that last couple of weeks. I always enjoy seeing how sexy you look." Jason email.

"Sexy, is it? Hmm, I didn't realize I was looking sexy! Are we flirting now, Mr. Anonymous? And again, who is this?" Cindy emailed.

"I guess we are flirting. Do you want to do more than flirt?" Jason asked.

"Wow, more than flirt. Getting kinda forward now. Okay, who is this?" Cindy replied.

"I'm just an admirer. I just thought I'd see if you would like to do more than flirt." Jason emailed.

"Why would you even say that. I'd really like to know who this is?" Cindy replied.

Cindy found herself scared, nervous, and turned on by the emails. She liked the emailers confidence and found the straightforward approach at doing more than flirting to be a turn on. She wasn't sure where it was going. After her marriage she was excited to get some attention. Jason, wanted to make a bolder move but wasn't sure how to do it. Then he had an idea.

"The other day you left your computer up while you went to lunch. I stopped by to see Sam and saw your screen. I liked what you were looking at." Jason emailed. That was his bold move. He jumped in. He was nervous and unsure how she would respond.

"Okay, what did you see?" Cindy responded. Her mind was racing and worried at what was left up for others to see. She remembered what she was looking at and became a little embarrassed.

"It was a sexual story. Consensual non consensual. Does that ring a bell?" Jason emailed.

"Oh no. That was left pulled up? Okay, who is this? I didn't mean to have that pulled up." Cindy replied.

"It's okay with me. I like CNC and blackmail stories too. So the question I have for you at this point is if you want to play a game. If you do, send me your personal email, and we can continue to talk more there. If not, I'll forget what I saw and just go about my business and you will never hear another word from me again. Beware though, the game will push your limits. It will be fun, exciting, and sexy, but still a game. You decide. I'll wait for your response." Jason emailed.

Cindy was nervous. She knew she had been looking at a website with CNC and blackmail stories. She tried to think who might have been up at her desk that day. She couldn't think of anyone specific. It could be any number of people. She was intrigued by the playfulness of her anonymous emailer. She was also scared at the same time. She decided to send him her personal email.

Jason got her personal email and sent her a new email on that email address.

"Great, I'm glad you sent your personal email. So here is how we will play. I will give you a series of challenges. If you complete them all, I will never mention anything about you looking at pornographic websites to your coworkers. But if you fail to complete these tasks, I will let all your coworkers know about it. You understand the rules?" Jason emailed.

"What the fuck? I thought you said you weren't going to tell anyone? What is this?" Cindy replied.

"Yes. I said if you didn't want to play I wouldn't tell anyone. I said if you wanted to play, to email me, and we would play. So now we are playing. You made the decision to play. Are you ready to start?" Jason emailed.

"What challenges? I'm not sure I want to play." Cindy replied.

"Well, we are playing now. I explained the rules. I promise that there will not be anything you do not want to do." Jason replied.

"Okay, fine, I feel like you tricked me into playing. I will play though, what do I do?" Cindy emailed.

"Tomorrow morning we start the game. I will email you with your first challenge at 8:00 am. Be ready." Jason replied.

"Tomorrow. You know it's Halloween tomorrow?" Cindy emailed.

"Even better. This adds so much to the challenges. I'll email you in the morning." Jason replied.

Cindy went to bed wondering who her emailer was. She was nervous, but she found herself more excited than scared. She had never done anything like this in her life.

"Good morning! Happy Halloween! Are you ready for your first challenge of the day?" Jason emailed.

"I'm good. How are you? Yes, I'm ready. I'm still in my pajamas, but I can get ready rather quickly." Cindy answered.

"I'm great. So let's get right to it. Your first challenge is to walk down to the mailbox and check your mail. The challenge is to do this wearing only a shirt and panties. To successfully complete this challenge your panties must be showing. Let me know when you have completed the challenge." Jason said.

"Oh my gosh, that was such a rush. Challenge complete." Cindy replied.

"Great. So tell me how you completed it." Jason emailed.

"You know I could always just tell you I completed these, don't you? But I did it. I wore basic cotton white panties and a shirt that come down to my waist. I walked down, checked my mailbox and came back. Nobody was out this early in the morning. Easy!" Cindy said.

"Yes, I know you can always lie and say you completed it, but how do you know I'm not outside watching? You never know. How did you feel walking down to the mailbox?" Jason asked.

"I liked it. I have never done anything like that before. It turned me on much more than I thought it would. I guess I have an exhibitionist side I didn't know about. I am newly divorced, which you might or might not know, Mr. Mystery Man! My marriage was very vanilla. I kinda like this game." Cindy responded.

"I had heard you were recently divorced. Your marriage was vanilla? Do you mean sexually? Today will be anything but vanilla." Jason emailed.

"Yes, it was sexually vanilla. We are talking lights out, missionary type vanilla. My ex-husband only wanted things a certain way. I guess I didn't know any better. He is the only guy I have every been with. Ever! I'll try to be a good sport about today, as long as this game doesn't get too out of hand." Cindy replied.

"Your next challenge is to go to Home Depot at 11:00am. The one on 4th street. I want you to wear a very short skirt and a very tight top or shirt. You are not to wear any underwear. Do not wear any panties or a bra. Email me when you get there." Jason replied.

"You want me to go there dressed like that? What if I see someone I know. They will think I'm a slut or something." Cindy replied.

"Today you are a slut. Today you will be pushed to your limits. This is part of the game. You can always stop now if you don't want to do the challenge. Of course, I will tell your coworkers about the porn, but you wouldn't have to do these challenges. It's your decision, but I think you will enjoy playing. I think it will be good for you to play. I think deep down inside, you need to play a game like this." Jason responded.

"How many more challenges are there?" Cindy asked.

"I'm not sure, maybe a few. We will see where the day takes us. Are you still playing?" Jason asked.

"Yes, I'll continue. I'll change now and go to Home Depot at 11:00." Cindy replied.

Cindy got in the shower and got cleaned up. She went to her closet and looked for something to wear. She found a white fashionable t-shirt. It was dressy for a t-shirt and it was tight. She had never dreamed of wearing it without a bra though. The material was too thin. She looked for something else but it was the only one that was casual and tight. She thought it would match well with a jean skirt she bought a few weeks prior. She had not worn either yet, but now was as good a time as ever. The jean skirt was very short. She bought it at the mall one day thinking it would be something sexy, yet casual to wear on a date. She put on a pair of ankle strap black heels to complete her outfit.

"I'm here." Cindy emailed.

"Great. What are you wearing? Did you wear what I asked?" Jason asked.

"Like you don't know. I'm sure you are probably somewhere here in the store watching me. I'm wearing what you asked. I'm wearing a tight white shirt. I'm also wearing a short jean skirt. I'm not wearing a bra or panties. I'm wearing black ankle strap heels. Every guy in here is looking at me. Did I complete the challenge?" Cindy asked.

"Well, I might be there watched, or I might not. No, the challenge is not complete yet. I want you to get a shopping cart and walk down isles four, seven, thirteen, and twenty-two. Go to twenty-two last and wait there." Jason instructed.

"Okay, I'm at isle twenty-two. I have at least four guys following me around the store. You just had to pick Home Depot didn't you. This store is packed with men today." Cindy said.

"That's exactly why I picked it. How does it make you feel with men looking at you? With them following you from one isle to the next?" Jason asked.

"Honestly, it makes me nervous, but I also kind of like it. They are all looking at me like that want me so bad. It's turning me on. One of them keeps staring at my nipples. The more he looks the more I'm getting turned on, and the harder my nipples are getting. They are now poking out more. It's very noticeable that I'm not wearing a bra." Cindy explained.

"Go to the middle of isle twenty-two and look near the bottom. Bend over and pick up something from the bottom shelf. Let any guys around you enjoy the view." Jason told her.

The isle had cans of paint and panting supplies. Cindy bent over as two guys nearby watched. She picked up a gallon of white paint and put it in her shopping cart. She knew the guys were watching. She could feel their eyes on her. She leaned down to look at a different can of paint. While bending over she knew her skirt was riding up, and she could feel her ass checks about to show. It turned her on to know these two guys were watching.

"Okay, it's done." Cindy emailed.

"What happened?" Jason asked.

"Like you wanted, I bent over and picked up a can of paint from the bottom shelf. I had two guys watching me. One of them approached me and asked for my phone number. I have it to him." Cindy said.

"It sounds like you have completed the challenge. Well done. Your next challenge is to drive to the mall. Email when you get there." Jason replied.

"I am here." Cindy emailed.

"Perfect. Today is Halloween. For you next challenge we need to get you in the Halloween spirit! Your next challenge is to go into the Halloween store in the mall. Once your inside, I want you to try on some sexy Halloween costumes. To complete this challenge you need to send me pictures of you in these costumes." Jason emailed.