text: So there was this dress... It was a famous dress, well amoung our smaller group of friends it was notable. At this time in my life though this dress belonged to the girl I was dating. If I were to guess now it was a sleeveless mini dress. Very smooth fabric and silver. What made it famous, or infamous depending on how you looked at it, was that the person it belonged to had talked all her male friends into trying it on, and taking a picture of them in it. The second that saw it I wanted to wear it. (It might be helpful at this point to tell you that I was born a male, and at this point in my life I still figured I was a cis gendered straight male.) However being a guy in the late 1990’s it wasn’t something I was just going to jump right into. I was also dating the owner of the dress. Anyway, one day while hanging out with my girlfriend and one of her friends they hanged up in me. The boyfriend of the other girl had already had his picture in her photo album. So why not me? They bugged me for hours, and I honestly liked the attention. I finally agreed and gave into their request other than the picture. I Kicked them out of the room because there was no way I was leaving my boxers on for this. I striped quickly and couldn’t help but smile and blush. Then I put the dress on, smoothed out the stomach, turned to admire my butt in her full length mirror. I know right? I was such a girl even back then. Then there was a knock at the door and I walked second the room to open it. Stopping because my socks were limp around ankles. I bent down and pulled them both up so they were more than halfway up my calf. Then stood up and smoothed it out again... as if I was going to walk on the red carpet or something... When I finally open the door my girlfriends mother was standing there alone. There was a long awkward moment of realization for the both of us. Her eyes went wide for a second behind her glasses as she looked down then quickly back up. “Hi.” She said still dumbfounded that her daughter’s boyfriend was in her rather revealing dress. “Hi.” Was all I said back. “Is Jess in there?” Her mother asked me, now with a single finger covering her mouth. “Nope.” Was all I said wanting to cross my legs and make myself smaller. “Any idea where she is?” “She was supposed to be waiting outside the door.” I shrugged at her wanting to die immediately. “Oh okay, I’ll see if I can find her.” “Okay.” Was all I said and closed the door. The next 5 minutes or so was a lot for me. It involved a lot of blushing and covering my face, then a lot of getting dressed quickly. Then a lot more blushing and wondering what the hell they were talking about. After the two of them coming back to her room and laughing at me for about 20 minutes I finally got the conversation between her and her mother. “Are you aware that your boyfriend is in your room dressing in your clothes?” “Yes Mom.” “You want to explain why your boyfriend is in your room wearing your dress?” After Jess took the time to explain everything her mothers response was a long sigh. Then her mother said “Oh Jessica,” and walked away. And I hope you enjoyed my second most embarrassing story.