I would love for you to comment and you can write me at bttm4u2@yahoo.com
I am putting on my silk stockings underneath my white evening gown that had a split up to my thighs and excited at the date tonight. I am a very passable trasgender woman I am 5'8" 140 lbs with shoulder length light brunette hair blue eyes.
I wasn't always like that I was a straight masculine man at least I thought I was but one day he said I could pass as a woman. He said with a wig make up and a padded bra I could turn straight men's heads. I told him he was crazy that I would never pass as a woman and it was dropped.
Than one day he said," If you don't think you can pass as a woman make me a bet."
I said," OK what is the bet?"
He said," We get you dressed as a woman saying you are looking for a masculine gentleman and we take your picture cross-dressed and put it in the personal section of the paper."
I asked," How long does my ad stay in the paper?"
He said," I think for 2 months should be long enough."
I asked," What is the payoff if I win?"
He said," If you win than we forget all about you being female but if you do go out on a date as a woman than you have to transition to a woman completely estrogen, castration you don't have to have a sex change surgery."
I said," Deal, and you will never bring it up when I win."
He said," When your date ends for safety reasons you will not reveal your body to him or have sex with him."
Well 2 weeks went by after my ad and my pic was in the paper and I forgot about it.
As I got back home the phone rang and the man on the other side said," Can I speak to Amy?"
I said," Let me get her."
I acted like I was yelling for Amy and I changed my voice to sound feminine.
The man asked," Who is that guy?"
I said in my feminine voice," That is my cousin he is visiting here from Minneapolis."
He said," Great, I saw your ad in the personals and you are quiet attractive how about a date?"
I said," That sounds good, when do you want to go?"
He said," How does Friday night sound we eat out do a little dancing."
I said," Friday sounds good."
I hung up the phone and started thinking I might be losing the bet but we still have to have the date. If the man comes over and turns me down because he suspected I was a man in drag than I won the bet.
After I hung up the phone it rang again and it was my friend.
He asked," Is this another night without a date?"
I said," No, it looks like a man called for my ad."
He laughed and said," All that has to happen is for him to close the deal."
I hung up the phone and it was the same man and I quickly changed my voice back to Amy.
I said," Hello"
The man said," I would forget my head if it wasn't attached. My name is Eric and I was wondering where you are living."
I laughed and gave him directions to my place and hung up the phone.
I looked up and saw it was time to go to bed and I undressed and went to bed wondering if I was going to lose the bet.