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Chapter 48
by twizted77
What is it?
Cheerleader
"You are gonna look so cute," Tina said as she closed her bedroom door behind you. Laid out on her bed was a cheerleading uniform. "I've been planning this for weeks now, I just didn't think you would ever really give me a chance to actually follow through with it. I'm a little shy around boys...but cross dressers are just so damn cute."
She picks up a tiny black thong and hands it to you.
"Usually cheerleaders have those cover ups they wear under their skirts, but I don't think you need those here," she said.
You peel off your own panties, which are filled with your cum and starting to stick to your pubic hair.
"You made quite the mess," she said as she opened a drawer on her night stand and pulled out a babywipe. "Let me clean you up.
Tina motioned for you to step closer and then started gently cleaning up your messy crotch with the wipe. It was odd. You'd never been touched there in such a nonsexual way. She very cafeful wiped up all of your cum and then tossed the wipe in her bedside wastebasket.
"Good!" she announced.
Slowly you pull on the cheer leading skirt as Tina watches, smiling approvingly. The she hands you the matching top, which fits you perfectly.
She then opens a trunk next to the bed and pulls out a long blond wig, which she carefully sits atop your head. She secures it with a pair of safety pins.
Tina then pulls out a makeup bag and quickly applies somethings that you really don't know about, finishing with a shade of lipstick that matches your uniform.
"Beautiful," she says when she is done. Tina grabs you by the hand and pulls you into the bathroom, putting you in front of a full length mirror.
You once again can't even recognize yourself. Standing in front of you is an attractive high school cheerleader with nice legs. You are even more convincing with the makeup on than you had been when you'd dressed yourself up.
"I bet you'd have a line of boys hitting on you if I took you to the basketball game game tonight, I might even be able to score with one of your leftovers" she said. "And I know my dad would love you. He has a thing for barely legal blonds. I saw it in his internet search history. He watches a lot of porn since the divorce. Which will it be?"
You had decided you were done cheating. But staring at yourself in the mirror, that yearning you'd felt with Bob was back. You wanted to be wanted so bad....
What do you tell her?
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Crossing over
An unexpected week
You are a married, straight male. Or at least you were until your wife went out of town for a week long business trip. When an unexpected visitor catches you wearing her clothes, things get a bit tangled up.
Updated on Sep 1, 2023
by twizted77
Created on Nov 14, 2019
by twizted77
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