Golf Crossdresser

A fellow has a week off from work and decides to play a round of golf every day. 

First thing Monday morning, he sets off on his first round and soon catches up to the person in front. He sees that this is a woman and, as he catches up to her on a par 3, that, in fact, she's very attractive. He's interested and suggests that they play the rest of the round together. 

She agrees and a very close match ensues. She turns out also to be a very talented golfer and she wins their little competition on the last hole. He congratulates her in the parking lot, then offers to give her a lift when he sees she doesn't have a car. All in all it's been a highly enjoyable morning. 

On the way to her place, she thanks him for the morning's company and competition and says she hasn't enjoyed herself so much on the course for a long time. He pulls up to her house, they kiss and she shows him her appreciation. 

The next morning he spies her at the first tee and suggests they play together again. He's actually quite competitive and slightly pissed that she beat him the previous day. Again they have a magnificent day, enjoying each others company and playing a tight competitive round of golf. 

Again she beats him at the last hole, again he drives her home and again she shows her appreciation. 

This goes on all week, with her beating him narrowly every day. This is a sore point for his male ego but, nevertheless, in the car home from their Friday afternoon round, he tells her that he has had such a fine week that he has a surprise planned: dinner for two at a fancy candle-lit restaurant followed by a night of passion in the penthouse apartment of a city hotel. Surprisingly, she bursts into tears and says she can't agree to this. He can't figure out what the fuss is about, but eventually she admits the reason. 

"You see," she tearfully sobs, "I'm a transvestite." 

He is aghast. He swerves violently off the road, pulls the car to a screeching halt and curses madly, overcome with emotion. 

"I'm sorry," she repeats. 

"You Cheat," he screams, red in the face, "You've been playing off the women's tees all week!!"

Crossdress Hooker

A couple were lying in bed together on the morning of their tenth wedding anniversary when the wife says, "Darling, as this is such a special occasion, I think that it is time I made a confession. Before we were married I was a hooker for eight years." 

The husband ponders for a moment and then looks into his wife's eyes and says, "My love, you have been a perfect wife for ten years, I cannot hold your past against you, in fact maybe you could show me a few tricks of the trade and spice up our sex life a bit?" 

She said, "No, I don't think you understand - my name was Brian and I played rugby for Wales."

Crossdresser & Air hostess

A crossdresser and a rugby player sat next to each other on an aircraft. After takeoff a flight attendant asked them what they would like to drink before their meal. "1'11 have a scotch and soda", said the crossdresser. "No way", said the rugby player, "I need to stay fit and would rather wear a dress than drink alcohol !" "That's fine sir", responded the flight attendant, at which the crossdresser exclaimed, "I'd like to change my order please !"