This is a true story. It happened exactly as I'm writing it. Last Saturday my son-in-law agreed to help me with some painting and minor repairs to my vacation home on the Jersey Shore. We had an early breakfast and picked up the supplies. Once we got started we both agreed that it would be more than a one day job. We worked hard till about 3 o'clock and took a break and cracked open a couple of beers. One led to two, then three, and soon we stopped work for the day. I suggested we go out for a nice dinner, but he had been working in a crawl space and his clothes were filthy. Not expecting to stay the night he hadn't brought a change of clothes.

I am a rather large guy and he is on the small side so my clothes wouldn't fit him. I suggested he could find a pair of jeans or slacks and a sweater or something in my wife's closet that he could fit into. He laughed at first but said 'what the hell" and went upstairs to take a shower. He came downstairs about a half hour later in a tight pair of jeans and a striped oxford shirt. He said he had a hell of a time with the buttons on the opposite side. I remarked sarcastically that with a little makeup and some heels he would be a pretty hot date. He smirked and lowered his head and softly asked if I would like him to do just that. I was quite surprised at his suggestion but decided to call his bluff. Without hesitation he said to make reservations at one of the casino restaurants in Atlantic City and went back upstairs.

About an hour later I heard the distinct sound of high heels on the stairway. When he walked into the family room I stared at him in shocked silence. He spun on his heels to model the dress he was wearing. I looked him up and down, he wore a tight fitting short black dress, dark stockings, and three inch pumps. His eyes were dark and sexy, his makeup was perfect and his breasts alluring and straining the fabric of the dress. He wore dangling earrings, a pearl necklace and bracelet. He had styled his hair femininely and even painted his nails! He looked better in that dress than my wife ever did. Sensing my shock and approval he wordlessly walked over to where I was sitting, knelt before me, expertly undid my belt and zipper, and before I knew it had his sexy lips wrapped around my growing cock. In no time he had me on the brink and teased me with his tongue and lips on my balls as he stroked my rock hard cock. I told him that I was about to cum and he immediately put me back in his mouth and swallowed my load. He looked up at me and smiled, lipstick and cum was smeared all over his lips and chin. He got to his feet and said he would fix his makeup and we could leave for dinner.

In the car he explained that he has been a crossdresser since he tried on a pair of his mother's panties when he was 12 years old. I was only the second person to see him dressed and the first cock he ever sucked. Whether or not that was true is probably up for debate. Anyway, we had a great dinner at the Borgata and even played a couple of hands of blackjack. No one seemed to notice anything out of the ordinary, he was quite convincing. He sucked me off again in the car on the Garden State Parkway on the way back to Sea Isle City.

Once back in the house we went straight to the bedroom. Despite our best efforts we couldn't manage to fuck. I wanted to take his ass badly but that will have to wait until another time. We agreed to get together again, but he was very insistent that no sex of any type would occur unless he was in his feminine persona. I can live with that.