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If you could, please provide feedback, so I can create better caption stories! If you like what you see follow me here and robinstgcaptions.blogspot.com/ for more caption stories. Thank you for viewing and have a great day!

Every year Oak Cress held a “sissify” charity event where sissified guys would compete through different events dressed as girls. It helped raise funds for school activities and taught the boys valuable lessons on what it felt like to be a girl, and everyone seemed to like it. Freshman, Hank, who had recently moved into the Oak Cress High School zoning, was unaware of this event. Despite being clueless about Oak Cress’s tradition, he was a closeted crossdresser, and he enjoyed the thought of participating in the charity event.

The boys attended classes to help them with charity event ahead to begin the week. The course went over the dress code, how to do make-up, apply wigs and a lot of stuff in between. Being a veteran crossdresser, Hank zoned out for most of the lecture until the teacher mentioned a unique catch this year; The person in last place would have to stay dressed as a girl for the rest of the semester. The boys around him groaned at the prospect of doing this, but Hank was thrilled to hear this, biting his lip not to show he was.

Come “Sissy Week,” the boys performed their duties, and Hank would purposely mess up to receive the lowest score. With the last activity being a 10k, Hank slowly jogged a long, enjoying the feeling of his running outfit and the beautiful weather outside. Knowing in a few hours, he’d be the school’s sissy for the semester, and he’d enjoy every minute of it.

Description
If you could, please provide feedback, so I can create better caption stories! If you like what you see follow me here and robinstgcaptions.blogspot.com/ for more caption stories. Thank you for viewing and have a great day!

Every year Oak Cress held a “sissify” charity event where sissified guys would compete through different events dressed as girls. It helped raise funds for school activities and taught the boys valuable lessons on what it felt like to be a girl, and everyone seemed to like it. Freshman, Hank, who had recently moved into the Oak Cress High School zoning, was unaware of this event. Despite being clueless about Oak Cress’s tradition, he was a closeted crossdresser, and he enjoyed the thought of participating in the charity event.

The boys attended classes to help them with charity event ahead to begin the week. The course went over the dress code, how to do make-up, apply wigs and a lot of stuff in between. Being a veteran crossdresser, Hank zoned out for most of the lecture until the teacher mentioned a unique catch this year; The person in last place would have to stay dressed as a girl for the rest of the semester. The boys around him groaned at the prospect of doing this, but Hank was thrilled to hear this, biting his lip not to show he was.

Come “Sissy Week,” the boys performed their duties, and Hank would purposely mess up to receive the lowest score. With the last activity being a 10k, Hank slowly jogged a long, enjoying the feeling of his running outfit and the beautiful weather outside. Knowing in a few hours, he’d be the school’s sissy for the semester, and he’d enjoy every minute of it.