Chapter 7
by 
MissAshleyJ
Who’s calling?
His “boyfriend”
The caller ID showed that it was Chad calling.
“Hi honey.” Timmy said
“Would you please stop with that.” Chad said.
Chad and Timmy has been roommates for a couple of years. After Timmy had started wearing his dresses full time, Chad confessed he had a fetish for trans women, and Timmy was the closest thing he could find to one who will talk to him.
So, they came to an arraignment. In exchange for Chad taking on more of the bills, Timmy would be his dream girl in bed.
Timmy didn’t mind, he was very much bi-sexual and he also liked to tease him about it.
“Look” Chad continues “I have a date tonight. And I need your help to pick out a dress.”
“Don’t worry sweetheart, I’ll be home in a jiffy.”
Timmy raced home, to find Chad in the living room, holding two gowns.
“Which do you think she’ll like more?” Chad asked.
“Who is she?” Timmy asked as he looked over the two dresses.
“Samantha Bridges.”
“Your BOSS?” Timmy asked.
“Turns out she used to be ‘Samuel.” Chad admitted. “So, red or black.”
Chad held up the two dresses. The red dress was strapless with a lace trim and the hem was cut at an angle so the rear was longer than the front.
The black dress had a smaller skirt, but a pair of giant puffy sleeves.
Timmy looked the two over.
Which should Timmy suggest?
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 10, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
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