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Chapter 2
by lovestoblush
What is Miss Pippa's assignment for Matt?
Matt never gets to his assignment.
"Excellent. We will be going to my house first. I have some chores for you." Miss Pippa starts driving. "Now normally I would probably have you come out naked, but seeing as it’s our first 'date' I am going to start out easy. I will only make you strip once we get to my place. Is that fair?"
Matt expected as much, but he still blushes and feels his penis grow. "Yes ma'am"
As they drive, Miss Pippa teases Matt a little. She brings up specific pictures he had sent, and how her friends loved them. After driving across town, Miss Pippa stops the car on a quiet street lined with an ornate wrought iron fence, bisected by an open gate. From Matt’s vantage point he could see a wooded path beyond the gate. Miss Pippa turned to Matt and said "You know what to do".
“Do you live here?” he asked, confused as to where they were.
“I said, you know what to do. Now strip!” she commanded in a stern, even voice. “Yes, ma'am”, replied Matt, quickly removing his clothes and handing them over to Miss Pippa, who turned and tossed them into the backseat.
Her facial expression and voice then softened. “To answer your question...no, I do not live here. I live on the street at the end of this path. This path bisects the campus of Davis Women’s College. Follow this path and it will lead you practically to my doorstep”. Taking a marker from her purse, she took his left hand in hers and wrote her street address on his palm.
Matt immediately turned bright red. Yes, the embarrassment and humiliation at the hands of this powerful and beautiful woman was extremely exhilarating, but was he prepared to possibly be exposed to any number of strangers, particularly young college aged women? The thought both filled him with dread and with intense nervous excitement.
“Miss Pippa, I’m not sure I…”
“Silence!”, Miss Pippa commanded.”Get out of my car…now”. Matt instinctively scrambled out of the car and onto the sidewalk. Covering his genitals with both hands, he quickly looked up and down the street for signs of cars and pedestrians. He saw neither, but nevertheless blushed with profound embarrassment at his naked predicament. Miss Pippa leaned over the now empty passenger seat, and through the open window asked, “You were saying?”
“I’m not sure I can walk to your home like this, ma'am”.
A look of pity came over her face, giving Matt hope that this humiliating event was coming to an end. “Then you don’t have to walk to my home, poor baby. You can walk to yours!”. And with that she revved her engine and sped away from the curb, leaving the helpless naked man alone on the sidewalk.
Almost immediately, however, Miss Pippa had put her car into reverse and drove back to where Matt was standing. She got out of the car and came around to the sidewalk, just a few feet from Matt.
“I have something that might help you”, she said, and with that she placed her hands under her tight mini-skirt, and with several seductive wiggles of her sexy hips, her lacy white panties fell to her ankles. Stepping out of them, she kicked the panties to Matt, who caught them in mid air, partially exposing his now hardening penis.
“Put them on!”, she ordered, ”they will cover your precious modesty”.
Doing as commanded, Matt stepped into the tiny, delicate, bikini cut panties. They unfortunately fit him quite well, despite covering him very little. Perhaps they were better than nothing but the tight fit highlighted his lack of a bulge and the back was immediately wedgied up his butt.
Miss Pippa's hand went to her mouth to suppress a giggle, but once recovered said, “Remove your hands from your junk. Let me see you”.
Blushing, Matt put his hands to his side, revealing that his penis was barely covered, the outline of which clearly defined through the sheer fabric of the garment. His balls peeked out from the legholes, and his pubic hair spilled out over the top of the lacy waistband. Matt stood quietly, his head hung in shame.
“Turn around, Matt. Let me see the rest of you”. Matt did as ordered, and revealed to Miss Pippa a generous amount of butt cheek on display as well as an inch of his crack. Miss Pippa gave his ass a hard, stinging slap, as if to punctuate her complete domination over this helpless, subjugated man.
“Follow the path, Matt, and I’ll see you soon at my house” Matt nodded without a word, and turned towards the path.
And with that Miss Pippa turned on her heels, gave her barely covered hips a slow swivel in Matt’s direction, returned to her car, and drove off in a cloud of dust. Matt watched her disappear over the horizon, and then quickly entered the path.
About an hour later Miss Pippa opened her front door to let in Matt, red-faced and distressed, and nearly in tears. “Sit down, Matt”, she said quietly, a soft smile developing on her beautiful face, “tell me all about it”.
What meets Matt inside Miss Pippa's home?
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Matt and Miss Pippa
Originally by Daring_Burlinski
This is a re-post with edits and story continuation from a story originally posted by Jenna Burlinski. This story is posted with their permission, and which names changed as requested.
Updated on Aug 1, 2024
by lovestoblush
Created on Apr 9, 2022
by lovestoblush
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