"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.
