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Chapter 5
by JennCarcione
What do you do?
Knock on Tom's door
I decide to power through. I put my phone in my purse and walk towards Toms house. Just as I am about to knock, Tom opens the door. He is wearing his black suit pants and a white button-down shirt. The top two buttons that were likely covered by a tie hours earlier are new open, exposing the top of his chest.
Looking straight in my eyes with a huge smile, Tom asks, "May I take your coat?" I nervously take it off and hand it to him. His eyes drop as he stares at my legs, scanning me like a TSA agent seeking contraband. My stockings end less than 2 inches before my skirt begins. I notice his eyes are focused on the back of my skirt which covers my butt by less than an inch. I nervously smile as he gives a 360 scan of my body. He stars silently and I begin to question everything. What am I doing? Does he think I'm too fat? Did I not dress sexy enough? Does he think I dressed like a whore? What felt was hours was about a second. Tom finally comments, "oh my god, you are drop dead beautiful! Come this way and let me get you a drink darling." Tom directly places his hand on my lower back and directs me down a short hallway.
We approach the living room where all the other two guys are already seated with two open chairs, presumably for Tom and Jack. There is a bar stool type booth about 3 feet opposite the seats. The two men are drinking Jonny Black on the rocks and chatting about the market. As I enter, the conversation amongst them comes to an immediate halt. They both stare at me and as their smiles turn to devious smirks. Tom gives a quick whistle and the other guy’s clap and laugh along. Tom directs me to a tall bar-stool type chair opposite them, asks me to sit and tells me he'll get me a drink. It's clear I'm seated so that all the guys can see up my skirt. Despite the guys staring up my skirt like 12-year old's who found their first porno, I am surprisingly okay with it.
Tom returns with my drink, "Here you go sweetie". Tom brushes his left hand down my back as he hands me the drink. He takes a seat and joins the others staring up my skirt and says, "sexy panties baby, Jacks gonna love it." All the guy’s giggle like teens. I nervously smile, then cross my legs. They guys chuckle quickly turn to a uniform "boooo" chant and we all laugh in good fun.
Tom gets up, walks over to me and whispers in my ear, "I almost forgot, come here". He begins to walk away, and I get up to follow him into the dining room. Tom says, "as promised" and hands me a shoebox. I open it to find a beautiful pair of black stilettos alongside a bunch of $20 bills. Tom says, "Put them on please and quickly come back, Jack will be here any minute now I want us all to surprise him at once." I go to the bathroom, take off my flats and put on my brand-new black stilettos. They match my skirt and stockings perfectly! I count the money to confirm it's $200 and place it in my purse. As I'm leaving the bathroom, I hear the door knock from outside. The only person left is Jack. This must be the moment. I rush back to the living room, and pass Tom in the hallway. He spanks my butt as he walks past me.
Do you say something?
Jack's birthday
His friends offered me money give a strip show
This is based on a true story that happened to me personally. An acquaintance was having a surprise 50th birthday party. His friends knew he had a sexual crush on me, and offered me money to provide a private show.
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Updated on Oct 22, 2023
by JennCarcione
Created on Aug 21, 2023
by JennCarcione
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