Natalie just stood there with an evil look on her face. I could do nothing but stand there, jaw almost hitting the floor. We both knew that I had just lost the bet. Which was, who could get laid first. I was amazed. We had just made that bet that morning. Damn she was quick. I guess it was easy for her, she was a knock out gorgeous, a bombshell, the type of woman every man fantasizes about. She had great, dirty blonde hair, a perfect hourglass shape. Perfect 36 C sized breasts, that seemed to defy gravity. She had a firm plump ass, an ass you could bounce a quarter off of. And finally, long shapely legs.
She was my best friend in the world, and had been since I could remember. We had grown up together. I watched her evolve from little girl, to a hot teenager, to a indescribably, super hot, super vixen. She was a cheerleader when I played basketball. And my senior year, when I was the captain of the team, and its star player, she was the captain of the cheer squad. Everyone said we should have gone out, that we would make such a great couple but nothing happened.
Well almost nothing.
One night, at a party, she was absolutely smashed. She started to flirt with me. I just passed it off as drunken banter. And just passed off. But she started to get more physical, rubbing my arm leg. I was finding it harder and harder to resist her. She was wearing a skimpy, tight, pink, halter top, which stopped just above her belly button. It showed a lot of her cleavage, which gave me a easy view of her breasts. Also, these extremely tight pleather pants. These left nothing to the imagination.
I was loosing the ability to resist. Here was the hottest girl I had ever seen, obviously wanting a piece of me. Then she kissed me, and by reflex I kissed her back. It was a long, passionate, kiss. I cupped her beautiful breast. She let out a slight moan. It was at that point I relied what I was doing. I backed away from her. Explaining how she was hammered, and it was wrong to take advantage of her. I got out of there, because I knew, if I stayed, I was going to fuck her till the sun came up.
"I won. You have to dress up in drag, and go out with me," Natalie, howled at me.
"Yeah, Yeah. I know. Just nowhere where people will know me."
"don't worry. We are going on a cruise. In the Caribbean."
"wow you are really going all out."
"Yes, and you have to be in drag for the whole week. Honey. Oh, and my younger sister is off from college, so she will be joining us."
Natalie's sister, Val, was almost as hot as Natalie. She was 21, and shorter that Natalie, but all the same oh so hot features. They were 2 in a million. Val and I were good friends, even though she was 4 years younger than me. I always used to see her when I was over Natalie's.
"hey, that's coo. I ain't gonna wuss out of our bet."
Natalie and I were both 5'9". I was a little more built than her though, so her clothes would fit me pretty good.
The night before we left, Natalie had me use this cream that made me silky smooth. She gave me a feminine hair style. Taught me how to do make-up, nails etc. Natalie had me try on the outfit I was to wear the next day. First was the bra and panties, black with some lace around them. Also some breast forms to fill out my shape.
Next was the garter and hose. Then the skirt, which was smooth, black with a rose on the front and back. It went down to my knees with two slits mid way up my thigh. Then was the white, spaghetti string, tank top. Then the final piece of clothing, the plain, small white, collared shirt. She buttoned up a few of the buttons. She then did my make up. She had me model in front of Val. I was surprised how well things fit.
"'she' looks pretty 'hot'" Natalie said to Val. Emphasis on 'she' and 'hot'. I passed it off as friendly joking around.
"oh yeah, if I were a dyke, I'd want 'her' pussy," Val responded with a wink, in my direction, and a strange look at Natalie.
It was getting pretty late and I got pretty tired. I told them that I was going to go to bed.
