A Woman's Wager

"Speaking of bras, where'd you find a bra to fit your 48" chest?"

"Let me tell you, again, I had to search high and low. I even went Online and when I finally found my size, I bought all they had, a white one, a black one and this beige one that I'm wearing now. I'm still looking for a red one for those sexy nights, if you know what I mean," said Jake noticing his friend staring at his boobs.

"They look so real," said Ed.

"Wanna feel? Go ahead. Take a handful of my boob. I don't mind, really. Go ahead," said Jake sticking out his chest just as an elderly woman entered the aisle and turned her carriage around to go the other way.

"No thanks, that's okay," said Ed. "I'll wait until I go home and grab my wife's boob, if you don't mind. Thanks anyway."

"They feel real. I have those gel implants in my bra and they feel like the real thing. Go ahead, feel my tit. Sometimes, when I'm horny and alone in the car, I feel myself," said Jake with a laugh. "It makes me horny to feel my own phony tits."

"Wow, they do feel like the real thing," said Ed finally succumbing to the temptation of feeling Jake's fake boobs and squeezing a handful.

"So anyway, she said she's been dressing up for 40 years and she bet me that I couldn't even do it for a week. It was her way of trying to make me understand what she must go through to get dressed and to make me understand in a small measure of what it feels like to be a woman. She didn't think that I could do it, but I did and I have, as you can see," said Jake moving his hands out from his sides and looking more like a fashion model.

"Okay, I understand that part of the bet but Valentine's Day was last month. Your week of having to dress like a woman was over three weeks ago. Why are you still dressing as a woman? Did you lose another bet?"

"I can explain that, too," said Jake looking a little nervous. "Once I started dressing as a woman, it released the inner woman in me and I liked it. I was free from neckties, business suits, white shirts, and wingtips on weekdays and flannel shirts, jeans, baseball caps, and construction boots on the weekends. Suddenly, for the first time, I felt pretty in pumps, pantyhose, pearls, and pillbox hats and I liked it."