Matt and Miss Pippa

Matt is lying in bed staring at the ceiling. He is really nervous and wondering if he can go through with this. His phone vibrates from a text message. It reads "I'm out front. Don't make me wait"

Matt stands up and looks in the mirror. He is wearing a t-shirt and shorts. He takes a deep breath and grabs his wallet, cell phone, and keys. He goes outside and locks his door.

There is a car waiting out front that he gets into. In the passenger seat is a approximately 30 year old woman, curvy and dark haired, she smiled with such confidence and mischief that it sent a shiver down Matt's spine.

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Matt only knows her by her online screen name Miss Pippa. They had gotten to know each other in an online group dedicated to members giving and accepting dares, and soon found out they even lived in the same city. Miss Pippa had posted a few dares, simple things such as streaking at night, that Matt had accepted. Soon she had contacted him directly. They chatted on messenger, and soon Miss Pippa was having Matt send pictures of himself, naked and posing for her. He even had sent her a video of him masturbating that she had requested. Of course at first he was too nervous to show his face in the pictures, but soon enough she had coaxed him into it. He was always very nervous and blushing as he took the pictures and sent them. Miss Pippa and Matt had discussed their turn ons, and it soon became apparent that Matt loved embarrassment. Every time he received a dare from Miss Pippa, he would get butterflies in his stomach, nervous yet happy butterflies. Over time, as Matt became more comfortable with her, Miss Pippa suggested they chat on the phone. From the very first phone call, their relationship changed. Matt had called Miss Pippa on a Saturday night. He dialed and when he heard her pick up, he excitedly greeted her "Hey Pippa, its Matt, I'm so glad to finally talk with you."

Her response was unexpected. "Matt, I am very disappointed in you. You shall address me as Miss Pippa, to show your superior some respect. Is that clear?"

Matt was taken aback, she did not yell, but her voice was very stern. "Uh, ok."

"Excuse me?"

"Oh, I'm sorry...yes ma'am."

"Much better, maybe you wont be totally worthless then. Now, I will explain my intentions, and we will go over some more rules. First, It has become apparent in your emails that you clearly love to be embarrassed. Since I am local to you, it is only right that I assume responsibility for you and help you complete assignments. So you will follow my orders, and any back talk will result in punishment. Now for some rules. I have a few for now, but know there will be more as time goes on. For now we'll keep it simple. 1. You are to never wear clothes when you are home alone. 2. When we are talking, you are to be completely naked as well, and that starts now." Miss Pippa waited as Matt stripped. Once he said that he was naked she gave him the final rule. "and finally 3. You must keep all windows and blinds in your apartment open at all times." Again she waited as he opened his blinds. Even though Matt was quick to comply, he was slightly terrified. This woman already had him blushing bright red and they had been on the phone only a few minutes. "Now Matt, I will call you soon and we will have some more fun, but before I go I have a small assignment, it will be very easy. I want you to send me a picture of yourself...standing in your front door way, with the door open. And know this, I WILL share this picture with a few friends of mine, so make sure to smile."

She didn't even wait for him to answer. She just hung up. It took Matt 5 minutes to build up the courage to take the picture, and another 10 before he could send it. He received a text back from Miss Pippa. "Well done, but next time I won't be so patient." For the next few weeks Miss Pippa would call Matt, and have him do a number of dares while on the phone. Nothing crazy, but still risky. He had driven around naked, run around his apartment building, even masturbating in a park, all while talking with her. After a month and a half, Miss Pippa had decided that it was time for them to meet in person.

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Miss Pippa smiles at Matt. Although she has seen many photos of him, this is the first time Matt has seen her. She is dressed in a smart business suit, tight short skirt and a blouse, with several of the top buttons open, showing a good amount of cleavage. She is extremely attractive and she know's Matt thinks so because of the small tent forming in his shorts.

"Hello Miss Pippa" Matt says. He is already blushing.

"Hello Matt. You look nice, are you ready for a fun day?"

"Yes ma'am"...