This happened during college ( a few years ago) and nothing could have prepared me for that moment. Now I feel like I should share my story with other crossdressers like me. Since an early age, I was fascinated by girls clothes, especially skirts and stockings. One time, when no one was home, I sneaked into my sister’s room and wore her grey pleated skirt and white stockings. Since then I was pretty hooked to dress up as a girl. Anytime I was alone in the house, I would secretly wear my older sister’s clothes. Long story short, I started searching the internet and found out about crossdressing, and with time, my desire to dress feminine grew more and more.
When I joined college, I had less time to dress up and having a roommate made it even more difficult. I used to share an apartment with a guy named Jake, he was pretty cool, liked sports and was very athletic. We used to get along pretty well. I was kinda introvert, had few friends while my roommate, Jake was pretty opposite of me. He had a lot of friends and loved hanging outdoor or go to clubs with his friends. Whenever I knew, Jake was going to be out for a long time, I would get dressed and enjoy my feminine time. I had a small stack of feminine stuff hidden safely in one of my suitcase.
One day, Jake told me he was going on a hiking trip with his friends that weekend and I was pretty excited to have some alone time to dress up.
This happened two months ago so I feel like I should share it. My roommate thought I was out of town on a trip with the rock-climbing club for MLK weekend, but it got called off for bad weather. I turned back around and headed to the apartment. Walked in, heard him taking a shower. Now we give each other shit all the time, so I thought it’d be funny to scare him. I hid behind a couch, ready for him to come out. He came out, walked into the hallway to a full-length mirror we have, and….WTF. He had shaved his legs, was wearing thigh high black socks and a short gray skirt, a neck choker, had dark lipstick on, and had his typical neck-length curly hair teased up into a more typical feminine style. The whole sight was shocking to me for a lot of different reasons—partly because of how well-executed it was. He has a lot of naturally feminine features and a thin frame, but clearly he has done this many times before. Now since this guy really thinks he’s the shit (he’s a skinny dweeb, but a confident one), my first instinct was to jump up and embarrass him—this would be something my friends and I would never let him live down. But that didn’t really feel right. Instead, I snuck out to let him do his thing in privacy and texted him ”yo on my way back, trip cancelled” while I got coffee. The real confession is….I think he pulled the look off well…really well…and I’ve been thinking about it for a few days now. Feels very weird. He has just been kind of a bro to me for four years and now all of a sudden when I’m talking to him, I notice his lips are kind of a nice shape. That’s the first first time I’ve ever written something like that about a guy.