It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited.
Not only did we get more excited, the closer we got, the more my girlfriend begged me to cross dress.
"Pleasepleasepleasepleaseplease!!!"
"No. N-O. That's final."
"Why not?" She asked.
"Because I'm straight and don't want to be raped in the bathroom."
"You won't! I promise!"
"What are you going to do? Hold my hand while I pee?"
That usually ended the conversation.
As the con got closer we all decided to cos-play, but we weren't sure what as. Then it hit us we were living representations of the Scooby-doo gang! Minus Scooby doo of course. I was to cosplay as Shaggy, my girlfriend as Velma, my best friend as Fred and my other friend as Dahpne. We even got an old van painted like the Mystery Machine to tie it all together.
When we got to the con plenty of people asked for pictures, we were so proud.
There were plenty of cross dressers there, mostly 30 or 40 year old men that didn't even look like a woman. I would count how many I saw, so I could tease my girlfriend. Once I got to 46.
"Please?" She said when we had stopped for lunch.
"What?" I was confused.
"Cross dress for me?" She batted her eye lashes and gave me... well you know... that face.
"Mmmm..." It was hard to resist looking straight at her, "Sure," I gave in.
"YES!" She gave a little dance.
My cheeks turned red as I thought of how stupid this would be. I gave a fake smile to her as I started to think of all the people I knew at the con, and how many could take pictures.
~
The next morning I got up early so I could get to my girlfriends house to get redressed, I'm sure my parents wouldn't have appreciated the "new" outfit.
I got to her house and she threw me a plastic bag from the couch.
"You're not even going to tell me how to put this stuff on?"
She sighed, "I guess I'll have to..."
I took off my clothes until I was completely naked. She tossed my a pair of her panties, they had roses all over them. I gladly put them on, that was the only part of this I would enjoy.
I had purposely not shaven anything so I wouldn't get into the role of being a woman, this was just a one time thing just to make my girlfriend happy. She frowned at my extremely hairy legs.
"I don't mind the face, but why couldn't you have at least shave THOSE monsters?"
I shrugged and put on some black leggings. They conformed to my legs, feeling very smooth and fresh. Next the dress. It was a blue floral dress. Very open and free. Then a grey cardigan.
She frowned and looked at it on me "I didn't realize how good that dress and cardigan go together!" She clapped her hands.
I rolled my eyes. "Yeah whatever."
I put on some Converse sneakers and she helped put on a blonde wig. It felt different having hair laying across my shoulders.
"Fuck!" I thought to myself, "What did I get myself into?"
To complete the outfit she put a mood necklace around my neck.
She jumped up and down and clapped her hands. "You look sooooo good! Oh! I almost forgot! We need a name for your inner cross dresser..."
"Uhhh... no... this is enough, thank you."
"No!" She laughed, "Hmmm...