How to please your girlfriend

(Some of this story may be slightly fabricated, but don’t worry about what is and what isn’t, just enjoy the story.)

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.


‘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 cosplay, 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 crossdressers 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.

‘Crossdress for me?’ She batted her eyelashes 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 girlfriend’s 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?’

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