I had been seeing Ron for about a year now. My girlfriend Sue had introduced us. Sue and I and Ron and his wife Carla often swapped partners and Ron and I got together about once a week for some hot man on man action. Sue approved and encouraged all of this and I had even told her about a recent gangbang I participated in where I was the main attraction.
The gangbang was held at an old farmhouse. There was a mattress placed in the center of the room and I entertained there. I sucked and had been fucked by a total of nine men. It was wonderful. I loved being fucked by men. But I wanted more. I wanted to meet other men and be something they had to have.
I was talking to Sue about how I felt and she listened and then spoke up. She told me that when she first met me, she thought I was gay. She said you are too handsome, you are actually pretty. She said follow me and we went into our bedroom. Sue said take off all your clothes. I did. She went in her drawer and pulled out a black thong panty. She said put that on. She then handed me her long black haired wig she often wore when she wanted to look extra hot. I put that on. She then took my hand and stood me in front of the full length mirror. She said turn around and look over your shoulder. I did. I looked good. Sue said most women would die to have legs and an ass like yours. I must admit I had nice legs and my ass was damn near perfect.
Sue then took me into the bathroom. She got out her makeup case and went to work. A few minutes later she said look in the mirror. I did and she was hot. But it was me. Sue said with makeup, a wig and your body you can get any man you want.
A few days later Sue surprised me with a pair of Come Fuck Me heels in my size. What was she doing.
A week later, Sue, Carla and two other girls had a trip planned to the Bahamas. It was late fall and they wanted some time in the hot weather and one more tan. I went each week to a tanning salon so I always had a tan. I know it was vain but with my blonde hair I just thought I looked good that way. I had just eaten something for dinner and was feeling horny. I thought about the wig and then came up with a crazy idea.
I went in the bathroom and found some of Sue's makeup. I did a pretty good job applying it and looked pretty good. I then put on a pair of Sue's thong underwear and one of her skirts. It was made of stretchy nylon so on me it was a miniskirt. I wore a loose fitting sweater and put on the wig and CFMs. I looked in the mirror and thought this was crazy.
I drove about thirty minutes out of town to a truck stop. There was a diner there and I parked and nervously walked in. Several patrons turned and looked but nobody seemed to notice that I wasn't a girl. I ordered coffee and waited. But nothing happened. I thought, this was a really dumb idea. I paid the tab and walked outside.
As I walked towards my car I heard a voice say how much? I turned and there was a middle aged man. He looked like he had just climbed out of his big rig. He was about six feet tall and maybe two hundred pounds. It never occurred to me that I looked like a hooker. I approached him and foolishly said how much you got? He asked, do you have a cock? I thought that would turn him off. I said yes. He said I'll give you fifty bucks if you suck and fuck me. I thought and said let's go.