When Having Alley Sex With A Hooker, Always Be Sure To Look For A Five O’Clock Shadow

I have a bunch of friends that work in the sanitation department – and let me tell you…those guys have some stories.

One night at four in the morning, one of the guys, who I’ll call Lou, came across a hooker.

“For thirty bucks I’ll give you a blowjob,” she said.

“Frank, you gotta let me borrow thirty bucks,” Lou said to his coworker. “I promise I’ll finish the rest of the route.”

Frank shook his head and gave Lou the $30. Then, ten minutes later, he was back.

“Frank, please man, I need another forty bucks. She said I can [have anal intercourse] with her for another forty! She’s so sexy, come on!”

Again, Frank handed him the money. Lou came back another fifteen minutes later with a huge smile on his face.

He completed the route without complaint. As they were nearing the end of their shift, and the sun was beginning to come up, Frank saw a familiar face. It was the hooker. Except, there was someone strange about her in the light.

As he neared her face, that’s when he realized it. She had a five o’clock shadow and an Adam’s apple. She was actually a he.

“You’re a dude!” he all but yelled.

“Yeah, so?” the transvestite answered.

“He thought you were a girl!” Frank said.

“Oh, shit,” the transvestite said, and ran as fast as he/she could — heels and all.

After much pleading from Lou, Frank vowed not to tell anyone. So, naturally, he told every single member of their garage when he got back.

Have you ever been tricked into thinking a man was a woman or vice versa?

One thought on “When Having Alley Sex With A Hooker, Always Be Sure To Look For A Five O’Clock Shadow

  1. OMG! this is so funny! I was with a friend in Amsterdam who went to the Red Light District to find a prostitute. They kissed and made out and when he wanted to have sex, she/he said, “I can only do it from behind!” My friend quickly realized his mistake and ran out of her place. At least he has a good sense of humor and can laugh about it, but it remains our little secret!

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