The Square & the Cowboy

INTRODUCTION & DISCLAIMER - This is an entry in a 750-word story contest and written for humour. It contains male homosexual activity. All characters are aged 18 and over, with similarity to real persons living or dead coincidental & unintentional.

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Once upon a time there was a young man named Terry. He was 18 and a square who spent his evenings at home studying instead of going out and having fun. While other guys and girls were enjoying themselves at the drive in, cinema or diner listening to rock and roll music, Terry was at home buried in his homework.

Terry who had red hair, fair skin and blue eyes was a handsome enough young man, but he had never been on a date, mainly because the girls at school thought he was boring. But this was only part of the reason. Terry harbored a terrible secret. He was a homosexual, but because it was 1960 he could never admit it to anyone. It was worse than being a communist. If people knew Terry was a queer, they would think he would go driving around town all day trying to tempt kids away from playgrounds with candy. Maybe even the police would come and arrest him and take him to jail. This could never do at all.

One of the popular girls in Terry's year was having an 18th birthday party this Saturday, and all the kids in the class were going except for Terry. He had to study. It was a fine night in Los Angeles where Terry lived with his parents, and they were going out for the evening too, a dance at the country club.

Terry, who wore a beige shirt and trousers that accentuated his uptight, square personality watched a TV news program about the upcoming Kennedy vs. Nixon presidential election, then went upstairs to his bedroom and began studying calculus, thinking how much better it was not being at the silly party for the popular kids.

Finishing his calculus, Terry picked up his chemistry books but was having trouble solving an equation when he heard noises downstairs. Thinking that the cat was playing around, Terry went downstairs to find the cat sound asleep.

Puzzled but not alarmed, Terry turned to go back upstairs then stopped in shock and fear. Framed in the kitchen door was the six foot six form of a man, a menacing looking scowling man with a huge moustache and dressed as a cowboy, a large cowboy hat upon his head, boots and a neckerchief.

The terrified Terry took to his feet and burst out the back door into the yard and the cowboy chased him. Terry thought he might be able to get over the fence, go to the neighbors and call the police but the cowboy was too fast.

The cowboy made his rope into a lasso and captured Terry, then hog-tied him as the teenager called out for help, but nobody was around to hear him.

With a face like granite, the cowboy approached his captive.

"Take anything you want, just don't hurt me," Terry pleaded, thinking the cowboy was a robber.

"I don't want to rob you, I want you boy," said the cowboy. "And I know you're going to enjoy it, faggot."

With that, the cowboy pulled down Terry's slacks and underpants, then pulled down his own trousers, showing an enormous erection. Terry knew what was going to happen and knew he should be scared, but instead of being scared the thought of being sodomized made Terry feel excited. Super swell excited. His erection proved this.

The cowboy got the hog-tied Terry in place on the lawn and thrust his big dick up Terry's ass, fucking the younger man hard up his rear end. All of his secret erotic dreams were coming true. The cowboy fucked him harder, and it wasn't long before Terry ejaculated without any touching by himself or the cowboy.

Soon after Terry felt the cowboy cum up his ass, then withdraw before pulling up his pants and freeing Terry from his rope binds.

"Who are you?" gasped Terry, who pulled up his own pants with a sore but satisfied ass.

"I came to teach you to enjoy yourself not to be such a square," said the cowboy. "Get out there and enjoy yourself sometimes. I hear of you being a square again, and I'll be back to get you."

With that, the mysterious cowboy turned and left into the night. Terry never found out his name or where he came from. He never saw or heard from him again.

After this, Terry was less of a square. He learned to have fun as well as get good grades, and lived happily ever after.