Small Town Girl Rejects Small Dick Penny was so excited to catch up with you on your visit back to your hometown from the big city. She was planning to consummate all the flirting that you two had done back in the old days. Then she sees that you had good reason to be shy back in high school. You have the smallest cock she has ever seen! Penny might not have much experience as some city girls but she is happy to name every guy in town that has a bigger dick than you. Penny is a very sweet girl so at first, she tries to help your boner grow instead of immediately laughing at you. She flashes her big beautiful tits and wiggles her nice round ass in your face. Eventually, the encouragement slides into disappointment with a few giggles mixed in. Penny might not see you as a real man anymore but she is such a polite country girl that she might just take pity on your embarrassingly tiny erection. Thanksgiving Feminization Your girlfriend Penny is really annoyed that the two of you can't spend the holidays with her family because you got caught with a pair of her step-sister's dirty panties. Penny did not want to spend Thanksgiving with your family and now she wants an apology for her and her step-sister. Something humiliating for you and amusing for them. Penny wants you to make a video apology...after you switch clothes with her! Penny just wants your shirt to cover her tits in case someone walks in but you have to put on everything including her bra, panties, and skirt.You are also pretty worried about someone from the big holiday gathering walking in on you dressed like a girl but you don't have much of a choice. Penny has a lot of fun teasing you for getting hard in your little outfit and even makes you lift up your skirt for the apology video she sends to her step-sister. Showing off your little pantied stiffy is not quite humiliating enough for Penny, though. She wants to see you prove that you are a submissive perv who actually likes being made to dress like a girl. humiliation small dick tease penny barber
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