1. Punished


    Date: 8/22/2015, Categories: Crossdressing, Author: pleatedskirt, Rating: 6, Source: LushStories

    so sorry, I won't do it ever again,” I cried. Peter looked at Jane, reached over, and took the skirt from her. “Perhaps I have a solution Jane. We need to do something that's going to discourage people from coming in here, stealing clothes,” and pointing at the cum slowly dripping from the skirt, “doing perverted acts like this.” “What do you have in mind Peter?” Peter looked at Jane once more before smiling. “This little creep obviously likes dressing up in women's clothing, so let’s dress him and put a sign around his next saying this is what happens to shoplifters.” The colour drained from my face in horror, “But I didn't steal it, you can't make me wear women's clothes in public.” Jane grabbed me roughly by the face and turned me towards her, “Make a decision, you do what Peter suggests or we call the cops. Your choice. And as for not stealing the skirt, you did something far worse.” In fury, she grabbed the skirt back from Peter and shoved it in my face, smearing cum all over me. I began to cry again, but I knew I could never face the humiliation of being taken away by police officers. “Okay,” I finally stammered. “I'll take your punishment, I know what I did was wrong.” “Good,” said Peter. “Jane could you take him to the back room and find something suitably humiliating for him to wear?” “It'll be my pleasure,” replied Jane. She grabbed me and roughly pushed me into the back room before telling me to sit on a wooden chair. While she started to look through a rack of ...
    clothes, I began to pay more attention to how Jane looked. She was quite tall and pretty, with long hair tied back into a ponytail. She was wearing a white satin blouse and a tight knee length black skirt. I noticed the colour of her stockings were also black as were her high heel shoes. She noticed me looking at her and angrily pointed at my clothes. “Take them off.” I was shocked. “You want me to take my clothes off in front of you?” She nodded. “That's right, take your clothes off or go to jail, your choice.” I accepted my predicament and began to take my clothes off. God, it was so humiliating. Never before had I felt so humiliated. It wasn't long before I was standing in front of her completely naked. She suppressed a small smile, “I can see now why you like pretending to be a girl.” Humiliated, I clasped my hands over my small penis. She was correct of course. I was a failure as a man. I had a small thin body with no body hair. She laughed again, this time holding her hands to her mouth to hide her laughter. “I am surprised though that such a small penis could make such as big mess of that skirt.” I felt so humiliated about how she was making fun of my cock, but the humiliation became even worse when she handed me a pair of pink satin panties. “Put them on,” she ordered. I did as I was told, but I had to admit the panties felt amazing as they slid up my legs. Next Jane threw a pair of silky black stockings at me and told me to also put them on. As I was pulling them up my ...
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