Wearing a frilly dress

Their were five pictures of Nathan posing on his knees in front of a mirror, wearing a frilly pastel dress as well as thigh high white stockings, heels, and a wig with long blonde hair. You almost didn’t recognize him at first, but when you went to mention it you saw his face was bright red with embarrassment. You decided to text yourself the most risqué of the pics before handing the phone back to him.

This went unresolved as you got an emergency call from your family and had to go home, and neither of you wanted to address it over the week. You wonder how long he had been crossdressing, how much he owned, and why looking at the pic turned you on. You planned to address it tonight as you went to his apartment for game night, but as soon as he opened the doors you realized it was his plan as well.

Your Best friend greeted you wearing another girly outfit, this one a black and red corset, red booty shorts, a chocker with a metal O ring, fingerless elbow gloves, and thigh high shiny black boots. His hair was styled, and he wore makeup that highlighted his pixie androgynous face. You were stunned as he led you in, letting you sit before he addressed the elephant in the room.

“You like my look? I do. You’re the first to know Scott, and I’m glad. But now that you do, I thought we should have some fun with it. So after thinking all week, I know just the way to make this night... let’s say, memorable.” He says with a wicked grin