From gamer to b*tch

Chapter 1

So me and my buddy have been gamer friends since high school. When we graduated we started going to different schools and working so we didn't have time to game like we used to, but we made time to get together have some drinks and game once or twice a week. When we we would game we would usually wager on our wins, something like by each others groceries or pay each others rent for the month. So on one of our get togethers a new fighting game came out, we decided to go and purchase it and play that night. While leaving the store excited to get back to his place an game, we see a trans hooker. She was not attractive at all my bud makes a comment on how bad she looks, I laughed an made a comment I wish I hadn't because it changed my life. When he said how bad she looked I agreed a made the statement I bet I would look way better than her. When i said it my friend kind of gave me a look but said nothing and we headed to his house and started gaming.
After getting the hang of the game we turned serious, eventually we were tied 9-9 it was getting late so we decided to make this the last game and wager against our win. I was getting tired and didn't play as hard as I usually do and lost the game. As I got ready to head home I my friend stop me and said we didn't discuss what you owe for losing. I figured it would be paying the rent cuz his fridge was full, but this time he said he wanted something different. I said ok well what do you want? He said since I would look better than the Tranny we saw early he wants to see it and laughed. When he said I wasn't taken back by it I thought it was funny and would be a great joke so I said sure no problem and it would also save me money.
So we worked out the details before I left. He said next week I was to show up next week as a girl and I had to take it seriously and not half ass it by just putting on a dress I had to make myself look as girly as possible. During the week leading up to our get together I went out and got some stuff a blonde wig some makeup, bra and panties which were the most embarrassing items to get, and was able to find a form fitting cocktail dress and some slutty heels. During the week I practice walking in the heels I was able to get it down easily.