I Cannot Make This Stuff Up

Here is an entry into the Best Worst Date Ever Contest sent to me via email. My pal Roadtripper submitted this and gave permission to post for your consideration. I can assure you that this is 100% true. Not sure if that makes it funnier or crazier or both, but I think we have a winner. Know your story is better? Submit it.

Without further ado, Roadtripper’s verbatim email:

This is the ultimate case of false advertising. J and I had been dating for a few months and everything had been going swimmingly. He was tough-talking Marine sergeant who swilled Jack Daniels, chain-smoked Marlboro Reds and covered his body in tattoos. The ultimate manly man… or so I thought. One night, we were hanging out on my couch and getting ready for bed when he busted out with the line that makes every girl break in to a cold sweat “There is something I have to tell you.” Several worst case scenarios raced through my mind. He was married… he had a STD… he was wanted by the law. No, nope, no.

J blurted out his big secret then jumped up to go get something from the other room. I was left sitting on the couch with my mouth hanging open, trying to process the information. Did he just say what I think he said? J returned to the room and threw a large book in my lap. I continued to stare at him, slack jawed with confusion. “Open it” he said. I started to flip through the pages. The pictures inside revealed that I had indeed heard his revelation correctly and that my tough guy Marine was indeed a cross dresser.

Being a cross dresser was one thing. Being a bad cross dresser was quite another. Picture after picture of thigh high boots, tacky school girl costumes and platinum wigs was too much.

I am all about consenting adults doing whatever they want behind closed doors. What people do in their bedrooms is their business. But this was my bedroom now… and this was just too much for me. J and I broke up. I will share a lot of things with my boyfriend but my eyeliner is not one of them.

Fast forward several months. J and I were still friends. I went to his blog to see what the latest was. There was a picture of him, dressed up in full regalia. Hey… that dress looks pretty familiar… holy crap! It was my dress that I had worn as his date to the Marine Corps Ball. I had gotten up the next morning to go to work and left it hanging on his bedroom door. The little bastard had drug his hungover ass out of bed, got all dolled up, donned my dress and staged himself a little photo shoot. And (sad to admit) I think he might have been cuter in it than I was.

Yeah… I still have scars from that one!


5 thoughts on “I Cannot Make This Stuff Up

  1. hm. doesn’t seem so bad to me. unexpected, obviously, but think of how close it could have brought you! not many tough-guy chainsmokers will be able to sympathize with you when your bra’s underwire isn’t cooperating… most of them would be to busy asking you to get them a beer or something.

    although some of the implication is that it was his taste in clothing that really deterred you. so did seeing him in your dress change your mind? 😉

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