I am a sissy maid

Part 1

Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn’t explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years…

A friend of mine, Peter, was into the same video games as I was, and we made a bet on who would win the next game. We usually played through a network connection, so we each played on our home computer.

That day, he was driving me home. We were talking about the game we played yesterday, and how he thought my win was not really a win, seeing as he was watching a movie at the same time. Arrogantly, Peter proposed we make a bet for the next game.

“What kind of bet?” I asked.

“Depends on how sure of winning…” he said.

“Well, I’ve beaten you a few times and I know your style of playing now, so I’m pretty sure I’ve got you figured out.” I said.

“Well then, if you’re *SO SURE*, how about this…if I win, you have to dress up in a French maid costume and clean my room!”

I looked at him in shock… “What? What kind of bet is this?!?”

He looked at me and smiled and said “The kind that you are sure you won’t lose!”

I paused and thought about it…why was he asking me to do this? Where did this come from? And most important of all…what kind of outfit was he talking about exactly? Like a sexy outfit or just a plain skirt and shirt kind of thing?

He could see I was hesitant but also considering it. I didn’t want to get into this unless I was sure I would win. Then I thought about what I wanted to get if I won. Not if I won…*WHEN* I won.
He then said: “And how about this…if you win, I will give you 500$.”

“500$?? Are you serious?” Suddenly, my focus was no longer on what would happen if I lost, but what would happen if I won. That was my first mistake.

“Wow, 500$...I could definitely use the cash…If I win, you pay up 500$, no questions or hesitations?” I asked.

“Yes! Now if you don’t think you can win, that’s fine, we can just forget about the whole thing…”