My wife and have started a bet that will run from March 1st till June 1.
In the past I have dressed only when I felt like it. If I was not in the mood or was lazy and did not want to go through the process of changing I did not change.
While I do have the option when I want to dress until June 1 the wife can also tell me when to change.
A few rules are in place. Such as it has to be at least for a five hour period and it will not interfere with our non-cross-dressing plans.
It is a complete change with makeup and a wig. Pants are occasionally allowed.
While we have just started this she has been having me dress on one of my days off and about four nights a week after work. The first night we started we painted our toe nails the same color.
We also had a five day mini vacation planned. A coworker of my wife was promoted so they canceled her vacation. I was informed that I was not to cancel my vacation and that I would be dressing the five days that we were scheduled to be gone. While five days in a row inside the house will be hard I am looking forward to it. We are going out of town this weekend and we will be shopping for nails for me to wear during the five days.
If I make it and dress every time I am told the wife does not win anything but she does not lose anything. However if she wins she wins forty dollars.
Wish me luck.
What are some of the other bets you have been involved in?
Lea