Crossdresser Stories

Enjoy this short story by Hellen Heels xoxoxo. He rubbed his chin. “Okay. What then do you do?” She swiped her phone and showed him the screen. “This is what I do.” He squinted as he regarded what she was showing him on the screen. “What is that?” “What can you see?” “Those are…aren’t those…those are female clothes on display.” “Look carefully, Mr. Principal. What do you see?” “I know what I can see. I am sure of it. They are female clothes – bras, panties, leggings, lingerie.” “Okay. Good. Now just a second,” she said as she typed something on her phone. She then showed the screen to him. “What can you now see?” He peered at the screen. “You drew the clothes on her. Yes, that is it. You drew those female clothes on her.” “Are you sure?” “Yes.” “Look carefully, Mr. Principal. Are you sure of what you are saying?” “Yes, of course. It is a woman who is wearing … No. wait. Let me see that picture very well…the woman has a beard and moustache? That is a man.” “And what do you notice about the man in the picture?”