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HowellingRobin — Dress Up

#secret #babysitter #crossdresser #crossdressing #feminine #feminization #crossdressingboy #crossdressingmale #willing #feminizationcaption #babysittercaption
Published: 2021-01-06 17:27:13 +0000 UTC; Views: 21291; Favourites: 173; Downloads: 46
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“You look so beautiful,” Sam’s cousin cooed. “I think I did a good job.”

Sam smiled. While not his ideal entertainment plan, the day’s adventure was amusing, and it kept his younger cousin entertained.

“You did a great job,” he admitted, pushing the hair back. “I think I look like a pretty woman.”

“You do,” she replied shortly, still in awe over her transformation process to Sam.

Sam was tasked to watch his younger cousin for the day. He offered numerous activities to kill time, all of which were denied. Running out of options, Sam opted for some dress up, something Sam knew kids her ages still enjoyed doing. Initially intended to be harmless, when she began asking Sam to dress up as a girl. At that moment, Sam began to question his decision. But she was thoroughly entertained, and Sam had to watch her the whole day, so he allowed the roleplay to continue.

What began as dressing up in her mother’s clothing evolved into her doing Sam’s makeup to “make him look like a girl.” The whole ordeal worried Sam, with the potential of his aunt and uncle walking in on a femininized nephew lurked as a possibility. The walk-in never occurred as Sam stared at his smiling cousin, which in return made him smile.

“Let’s not tell anyone about this, okay?” he asked. His cousin giggled and nodded.

“No problem, Samantha.”

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Comments: 2

SoCalSecrets [2024-06-12 18:16:39 +0000 UTC]

👍: 0 ⏩: 1

HowellingRobin In reply to SoCalSecrets [2024-06-13 13:36:40 +0000 UTC]

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