Halloween Challenges!

"Here is the first one!" Cindy said.

Attached to the email was a picture of Cindy in a nurses outfit. The outfit was barely covering her. Cindy didn't have any underwear on and the nurse outfit was very, very, short and very revealing on her breasts. She was wearing white thigh highs that were not covered by the nurses dress outfit.

"Very nice! Do you like that one?" Jason asked.

"Yes. I've never tried on anything like it before. I'm shocked at how little it covers. I feel naked wearing it. I also feel like one of the employees is trying to look in the dressing room. He keeps walking back and forth by the room asking if I need anything else." Cindy replied.

"Try on the next one, but this time, leave the curtain open enough so that he can see inside." Jason said.

"Oh shit. That was intense." Cindy replied after a few minutes. Here is your next picture.

Attached was a picture of Cindy wearing a pair of angel wings and a white, short dress. She had on her black ankle strap heels. The picture wasn't a selfie, someone else took it.

"Very sexy. Who took the picture?" Jason asked.

"I can't believe I'm doing this. It was the employee who was walking by. He saw my changing and then just stopped to watch. I tried to ignore him but he was watching. I fumbled around with the wings and couldn't get them on, so I asked for his help. It just got a little more involved than I thought." Cindy said.

"How involved?" Jason asked.

"He was turned on, and I was turned on. I had never done anything like this before. He is cute. He is younger. He is in he early twenties. When he lifted the wings to go on my back, the white dress that I had on got caught and lifted up. When that happened, my bare ass was showing. I was facing the mirror and didn't notice. I guess he did notice. He saw my ass showing and closed the curtain. Anyways, he ended up grabbing my ass." Cindy explained.

"Did you like it? Was that all he grabbed?" Jason asked.

"Well, yes, I did like it. I was so turned on. I was in shock at how brave he was to just grab my ass like that. He just kept his hand on my ass and I froze. We made eye contact in the mirror and I felt his hands go from my ass to my sides and stop on my hips. I should have stopped him or said something, but I didn't. I just maintained eye contact as his hands left my hips and went straight for my pussy. Oh fuck. I can't believe I let him do that. We just locked eyes the entire time. I felt his finger feeling around. I knew what he was going to do. I didn't stop him. His fingers went inside me. He broke eye contact and kissed my neck. That's when I broke away and asked him to take my picture." Cindy said.

"What happened next? Where are you now?" Jason asked.

"He took the picture and then I politely told him I needed to change. I put my clothes back on and left the dressing room. I'm at the back of the store emailing you right now." Cindy emailed.

"I would say your challenge is complete. Are you ready for your next one?" Jason said.

"Yes, but I feel like a complete slut. I shouldn't be doing this. Isn't this enough? Shouldn't the game be over now?" Cindy asked.

"You know the rules. If you quit, I will tell your coworkers. Besides, I don't think you want to quit. I think you are having fun." Jason replied.

"Sure, it's a little fun, but it's getting carried away." Cindy replied.

Cindy was having fun. She didn't want to admit that to her emailer, but she was having one of the best days of her life. She was doing things she had never done before.

"We haven't even got to the good part yet. Go buy the nurses costume and head home. Email me when you get home." Jason said.

"Okay, I'm home." Cindy said. "Do you have another challenge?" Cindy asked.

"For your next challenge, create a Tinder dating profile if you don't already have one." Jason said.

"Tinder? No, I don't have one, but I just created one. What do I do now?" Cindy asked.

"On your main profile picture, use the nurses outfit picture as the main one. Under the headlines, put that your are looking for fun." Jason emailed.

"Okay, it now up as my main picture." Cindy said.

"Start swiping right on every match, no matter what. No matter who it is, swipe right." Jason said.

"Okay, I'm starting to get some messages now." Cindy said.

"Your challenge is to spend the next three hours flirting and talking with these guys online. Anyone who messages you, you have to talk and flirt. I'll check back with you in three hours." Jason said.

Cindy enjoyed flirting and talking. She loved the attention. She had been missing the attention and sexual desire during her marriage. During that two hour period she talked to a good number of guys. Some of the conversations got sexual very quickly. Cindy couldn't help being so turned on. She stripped down and masturbated as she talked with these guys online.

"Did you meet anyone?" Jason emailed.

"Yes, I met a few guys." Cindy answered.

"Congratulations, you have come to your last challenge. Are you ready for it?" Jason asked.

"Yes, let's do it." Cindy answered.

"Okay, for your last challenge I want you to do two things. First, go change into the nurses outfit and send me a picture. Second, I want you to type out this message to five of the guys on Tinder. I want you to say: 'Hi, Halloween has made me super horny. I'm sitting her all dressed up in a slutty nurses outfit and I'm wanting some company. I want you to get in the Halloween spirit too. I want you to dress up as Michael Meyers from the movie Halloween and come to my house. I love role-play. You will walk in and have your way with me without ever taking off the mask. My address is (type your address here). I will only wait around for a little while, so if you want this, you better hurry up and get over here.' After you send it to five guys, screenshot the sent message, so I can see you have sent it. You can pick any five guys you want, but they have to be ones you have been talking with." Jason emailed her.

"Okay, so all I have to do is to send five of these messages? Then the game is over and I have completed all the challenges? I don't actually have to do anything after I message them?" Cindy asked.

"That is correct. After you send the message you have completed all the challenges. If you decide to continue on with any of the men you messaged, it's completely up to you. It's your decision. I won't mention anything to your coworkers, everything ends here." Jason replied.

"Okay, hold on, I'll send you the screenshots." Cindy replied.

Cindy changed into the nurses costume. She put on the tight nurses dress and white thigh highs. She had some red high heels that matched her outfit. She sent Jason a picture with her in the costume.

Cindy then went in to her Tinder profile and messaged five guys who she though were hot. She was sad the game was ending but relieved to know she wouldn't be doing anymore.

"Got them. Congratulations, you have completed the game. I hope you enjoyed it. Maybe I will catch you looking at porn again, and we can play some more." Jason replied.

"Thanks! Are you not ever going to tell me who you are? You are going to leave me hanging?" Cindy emailed.

Jason didn't answer. He remained silent. Cindy paced around her house wondering who her mystery emailer was. After a few moments the doorbell rang. It was then that Cindy remembered her messages to the guys on Tinder. She planned on messaging them to tell them she changed her mind. She was shocked one of them made it to her house so fast. Cindy walked to the door, still in her nurses outfit and looked outside.

"Trick or Treat!" Yelled a man in a Michael Meyers costume.

Cindy panicked. She wasn't sure what do do or how to handle this. By instinct, she opened the door.

"I'm sorry, I meant to message you back and tell you I changed my mind." Cindy said to the man standing at her door in the Michael Meyers Halloween mask.

Jason had planned this out. He knew he had to get to her house first. As soon as she sent out those messages he was almost to her house dressed in his Michael Meyers mask.

"Which one are you?" Cindy asked.

Jason, in the Michael Meyers mask just turned his head sideways in confusion. He shrugged his shoulders.

"I'm sorry, that didn't come out right. I meant, what was your name again?" Cindy asked still stumbling around with how to handle the situation.

Jason took a step forward inside her door. Cindy took half a step back. She thought about shutting the door or telling him to stop or backup. Instead, she froze. He unbuttoned the top buttons on the jumpsuit costume. Cindy backed up more and looked at his chest as he was unbuttoning the jumpsuit. She was still in shock but also curious as to who it was at her door. What little of Jason's chest she had seen, she liked. She didn't want to tell him to stop. She watched as Jason finished unbuttoning the jumpsuit down to his waist. He opened it to show her his chest. Cindy could see he wasn't wearing anything under his jumpsuit.

"Oh my. Well that is nice. But like I said, I think there has been a miss communication." Cindy said in flustered voice.

Jason turned his head sideways with another confused gesture. He grabbed Cindy's hand. At first, she resisted, but Jason was persistent. Cindy finally gave in as Jason guided her hand down his jumpsuit to feel his cock. He was hard. He wanted Cindy bad. Looking at her half naked in that nurses outfit had him ready to explode.

"Oh god. Fuck you have a nice body." Cindy said. "I can't believe I'm doing this."

Jason let go of Cindy's hand, but Cindy did not let go of his cock. She continued to feel it in her hand. She stroked it up and down, her eyes still on Jason's chest.

"Is it Chris?" Cindy asked.

Cindy was still trying to guess which person was at her house dressed up in the costume. Chris was showing off his chest in his Tinder profile. She thought it might be him.

"Maybe." Jason answered in a low voice.

"I guess you are here to have your way with me?" Cindy asked.

Jason confirmed by shaking his head up and down.

"Okay, I just have never done anything like this before. This is just out of the ordinary for me. But, we are here, let's do this, right?" Cindy said trying to reassure herself she was actually going to go through with it.

Jason again confirmed by shaking his head up and down. He then glanced down at Cindy's body in her nurses outfit.

"You like it? You think you can handle a slutty nurse?" Cindy said doing a few modeling poses to show herself off in the costume.

Cindy grabbed Jason's hand and led him to her bedroom. She hadn't been with a man other than her husband. She was nervous, but after the sexually charged day she had, she wanted to fuck. She felt sexy in her nurses costume, and she had a man with a hard cock standing in front of her in her bedroom. Today was the day she fucked the second man in her lifetime.

"Let's take this off." Cindy said grabbing the Michael Meyers mask.

Jason quickly grabbed the mask and held it on.

"You don't want to take it off? I'm okay if you want too." Cindy said.

Jason shook his head no.

"Okay, we can keep with the role-play. After all, it is Halloween." Cindy said.

Jason let his jumpsuit fall down to around his ankles. Cindy watched it fall, and her eyes immediately went to his hard cock.

"You must have a thing for naughty nurses!" Cindy said flirting. "What is it you want?" Cindy asked.

Jason looked down at his hard cock. Cindy picked up on his signal.

"You want me to take care of that for you?" Cindy asked.

Jason nodded to say yes.

"Okay, I guess this Michael Meyers doesn't need a knife. You have this hard cock as your deadly weapon. This is so big you could almost hurt a girl with it." Cindy said grabbing it in her hand.

Cindy stroked his cock a few times. It was already so hard. She was very wet. She wanted his cock bad. She wanted to jump on the bed and have him fuck her. She hadn't had sex in over a year.

Jason's hand came up and started to unbutton Cindy's nurses dress. The first button basically kept her breast covered. After he unbuttoned the first button, her nipples came out of her dress. Jason took both breasts with his hands. He felt the rest of the way into her nurses dress. Cindy continued to stroke his cock with her hand.

"You are so hard. You must want to fuck me bad?" Cindy said.

Jason nodded yes.

"How do you want me?" Cindy asked.

Jason took his hands off her breasts and took his right hand up to Cindy's face. He gently felt her cheek. Cindy moved her face to affirm Jason touching her. She continued to stroke his cock. Jason moved his hand over to her mouth. His fingers were on her chin. His thumb was on her lips. He did a circular motion around her lips until she slightly opened them. He pushed his thumb inside her mouth. Cindy took Jason's thumb and sucked it. Jason moved it in and out as she sucked.

"You want me to suck you?" Cindy asked.

Jason nodded to confirm he wanted it.

Cindy squatted down in front of Jason. She took his cock with her hand and pressed her lips up to the tip of his cock. With her tongue she seductively licked the tip of his cock.

"You have a beautiful cock!" Cindy told him.

Cindy opened her lips and took him in her mouth. Jason grabbed her hair on the back of her head, letting her know he liked what she was doing. Cindy was wearing a little nurses hat and it almost fell off.

Cindy started slow but built up speed. She took all of his cock in her mouth. She grabbed his ass with her hands. Jason looked down watching her bob her head back and forth taking his cock.

"I'm so fucking turned on, my pussy is so fucking wet!" Cindy said stopping for a moment.

Jason pulled on her arm signaling to her that he wanted her to stand up. She stood in front of him, and he finished unbuttoning her nurses dress. She wasn't wearing any underwear under the dress. He looked at her body as she finished taking off the dress and put it on the floor. She had a nicely trimmed pussy. She was still wearing the white thigh highs, red heels, and a white nurses hat from her nurses costume.

"You ready to fuck a naughty nurse?" Cindy asked.

Jason turned Cindy around and pushed her face first onto the bed.

"Oh my. You like it rough!" Cindy said laying face down.

Cindy put both heels on the ground. She stayed face down on the bed but arched her ass out towards Jason. She was nervous. Another man's cock had never been inside her pussy. She knew she was moments away from feeling a hard cock inside her. She grabbed the bed with her fists. Jason stood behind her. He felt her ass with his hands. Cindy has a hard body and a very tone ass.

"I love you touching me!" Cindy looked back to say.

Jason continued to feel Cindy's body. She had always dressed so conservatively at work that he never noticed had good a body she actually had. He moved his hand across her ass until it was between her legs. He felt down just a little to touch her pussy. With his middle two fingers he went inside her.

"Oh fuck!" Cindy yelled.

Cindy was extremely wet. Jason started slow but built up speed. He was fingering her from behind. Cindy started to shake. She was about to cum.

"God, don't stop. It feels so good." Cindy yelled.

Jason was shocked she was getting so turned on so fast. It made sense because she hadn't been with another man, or any man, in a long time. He wanted to taste her pussy but wasn't sure he could risk taking off the mask.

He knelled behind her. Cindy's was looking down, her face buried in the bed. Jason slid the mask up partially to uncover the lower part of his face. He then pushed his face into her. His nose basically in her ass and his tongue deep into her pussy.

"Oh fuck. Your tongue feels great inside me!" Cindy yelled.

Nervous that the mask would fall off, Jason stopped and stood up. He put the mask back covering his face.

With his hands on her hips and he positioned himself behind her. His cock pressed up against her pussy.

"Yes, fuck me!" Cindy yelled.

Jason thrusted hard inside her. Cindy's pussy was tight. She grabbed hard on the bedding with her fists.

"Ohh fuck!!" Cindy screamed.

This was the second man to ever fuck her in her lifetime. Everything about Jason was different than her husband. Jason's cock was so hard he was throbbing. He wasn't overly rough, but he wasn't gentle. He took command and fucked her hard from behind. The more Cindy yelled, the harder he got, and the more intense he fucked her.

"I'm going to cum!" Cindy yelled as put her face into the bedding and screamed.

Jason felt Cindy cum. He was close himself.

"How naughty of a nurse are you?" Jason said without thinking about his voice being recognized.

"Very naughty!" Cindy told him.

Jason was relieved she didn't recognize his voice. Cindy didn't think twice about trying to recognize his voice. She was still trembling from her orgasm.

Jason pulled his cock out of Cindy and pushed her further up on the bed. Cindy had basically collapsed anyways. Jason took his thumb and put it up again Cindy's asshole.

"Oh my god!" Cindy yelled.

Cindy felt Jason push his thumb inside her ass. It was tight at first but after a moment or two Jason was moving it in and out of her.

"What are you going to do?" Cindy asked.

Jason didn't answer, he continued to work his thumb in and out of her ass.

"Fuck. Are you going to fuck me in the ass?" Cindy asked.

Jason continued to work Cindy's ass with his thumb.

"Please be gentle. I've never taken it in the ass before. Please!" Cindy said. "Oh fuck!"

Cindy was getting extremely turned on. She was nervous, but wanted the experience.

"I have KY in my nightstand. Please. My husband never liked foreplay and I needed it. I haven't used it in a while, but it's still good. I've never been fucked in the ass before." Cindy said.

Jason stopped working Cindy's ass with his thumb and went to the night stand. He got it out and got back behind Cindy again. He put some on his thumb, and and pushed it in her ass. The KY made it smooth for his thumb to go in and out.

"Oh fuck, it feels good." Cindy yelled.

Jason straddled Cindy from behind. His legs over hers. He was positioned to fuck her in the ass. With one hand he continued to use his thumb on her. With the other he put some KY on his hard cock.

Jason pulled his thumb from her ass and pressed his cock to her asshole. Her grabbed her hips and slowly went inside her ass. He pushed in a little and stopped. He paused for a moment and pushed in a little more.

"Holy fuck!" Cindy yelled out.

It took a moment but Jason's cock was finally completely in her ass. Jason pulled up on her hips and started to fuck her. With slow movements, he went in and out of her ass. His cock got harder than it had ever been before.

"Oh fuck. I've never felt anything like this before. Fuck." Cindy began to scream.

Jason fucked her harder and harder. Cindy took one of her hands and rubbed her clit while Jason fucked her ass.

"Oh, oh, I'm going to cum again!" Cindy yelled. "Fuck!"

Cindy came again, with Jason fucking her ass and she rubbing her clit. Jason couldn't go any longer. He gave one last thrust. He had his cock deep inside Cindy's ass. With that last trust, came inside her ass. He fell over in exhaustion on Cindy's back.

"Holy shit, that was amazing!" Cindy said laying face down completely exhausted.

After a few moments, Cindy and Jason got out of bed. Jason got dressed. Cindy covered herself back up with the nurses costume.

"So, am I going to see your face?" Cindy asked.

The doorbell rang immediately after she asked.

"I guess it's trick or treaters already out getting candy." Cindy said.