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HowellingRobin — 30 Days of Captions Day22 Pat

#sfw #acceptance #brotherandsister #caught #coerced #confession #cousin #crossdress #crossdressing #discovered #makeover #punishment #sissy #transformation #transformationtf #crossdressingboy #sissycaption #willing #transformationcaption #caughtcrossdressing
Published: 2022-06-22 12:54:15 +0000 UTC; Views: 27682; Favourites: 106; Downloads: 18
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(www.deviantart.com/howellingro… ) Words list

“You have come such a long way on your journey to womanhood,” Hailey complimented, patting her new cousin on the shoulder. “I’m proud of you.”

“Well, thanks for showing me the way,” Lionel thanked. “I know I was difficult at first.”

Every summer, cousins Hailey and Lionel would spend the summer together. Their parents wanted them to get along, and while they did, they became mature, and interests separated as time passed. Despite this, the summerly tradition continued.

This year, Lionel decided to do some exploring. While alone, he snuck into Hailey’s room to snoop around. While stifling through the undergarment drawer, Hailey walked in and caught him. Shocked, Lionel claimed he was only looking for her diary, but the evidence was damning. After the threat of telling her mother, Lionel broke down and confessed he wanted to know how it felt to be and think like a woman. The breakdown was authentic, and after some probing, Hailey found out Lionel had issues relating to and talking to women. She agreed to help, but her measures would be extreme, but Lionel desperately agreed. Over the following weeks, Hailey dressed up her cousin and taught him the “ways of the woman.” Everything from maintenance, clothing, what goes through their minds, and everything in between. Lionel was soaking it all in and enjoying every moment, finally understanding and becoming more confident. The pats of a good job were rewarding too, and Lionel thinks he understands women more now. But he does like dressing up with his cousin more. 

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