The Prize | THE BOY JACK WATERS | Chapter 4

For perhaps the one thousandth time since I picked up the mysterious golden ticket off of that table, I wonder why I did it and what I was thinking. Of course I know the answer to that, in two words, my father. Veteran, Purple Heart recipient, Congressional Medal of Honor winner, the national hero with five stars glittering on his shoulders.

His history in the military began with his great great great grandfather, who organized the 84th Illinois Volunteer Infantry regiment during the Civil War and served as its commander. He was commissioned as Brevet Brigadier General of volunteers, near the close of the war for an act of bravery. The Waters men had served, and fought in every war since that time. Like his ancestors, his illustrious family left him to sign up anonymously as a private and make his way on his own. My dad literally lifted himself by his own bootstraps.

He expected his sons to do the same, and his pride, joy, and eldest son, was well on his way. I on the other hand was the disappointment in the family: bookish, shy, and not eagerly athletic. The old man would have heart failure if found out that I was gay as well.

My father refuses to pay for the education that the military would gladly provide for his sons. I don’t want to end up like him or my brother, or as hard, arrogant, and regimented as my uncles, either. I need a way out. With no money for college, simply running away would mean that ending up on the street was the likely alternative. If I was going to end up selling my ass, I might as well make a pretty penny.

Selling myself into sex slavery might seem extreme, but desperate times require desperate measures. So far, I feel like it could be far worse. I’ve traded my boyhood military cot for an actual bed. It’s a single bed in a simple room, but it‘s luxury compared to the way I grew up.

The Masters that I have met are stern, almost intimidating men. Unlike my father, they have appreciation in their eyes. Their touch is firm but gentle, even if it’s not loving. Master Saint bought me at the auction. I guess I must have pleased him. Slaves are not supposed to know their price but the auction seemed to go on forever, and I know from what I overheard that my price was high.

Master Saint is the most intimidating of the Masters that I’ve met, and I could almost wish that one of the others had won the auction. But you can’t judge a book by its cover. Master Saint is a handsome man, in a very rough hewn kind of way. He has a big cock, almost too big, but I’m getting used to it. He likes to put me on my stomach, lay on top of me, and fuck me hard. Really hard. I’ve discovered that I like that.

After the auction, we went back to his house. He gave me a few hours to unpack and settle in, and nap or shower if I wanted. Maybe it’s my imagination, but when he’s not fucking me, sometimes I think I catch a fleeting look in his eyes. Something slightly softer and more affectionate. Maybe if I‘m obedient and follow his orders carefully enough, he’ll let that come out more often.

After my alone time is up, I report to his room. I wait in the hall for a few minutes to step in the door just as the clock down the hall chimes. He is very stern and gruff telling me how to undress him. I try to remember as much as I can. I think it will please him if I can do it without being instructed. He likes me to look into his eyes at all times but it’s hard not to fumble without looking down.

While undressing, he spins me around, spreads my cheeks, and shoves his tongue into my hole. I don’t know if I’m allowed to make noise or not, but I can’t hold back a moan. I start sucking his cock just hoping that I will do it right. I was expecting more growling instruction but he just laid back on the velvet duvet and sighed.

He tells me to get his cock wet and that he expects me to sit on it and ride him. He feels huge in my ass. I’ve never been fucked by a grown man before. He doesn’t seem to care how much I whimper. I think he likes knowing how difficult it is to take him. I guess every man likes to think he’s hung and, in his case, he is.

Soon, I’m on my stomach with him on top of me driving his dick into me balls deep, over and over until I feel like I can hardly breath. Then he lets out an animalistic grunt and I feel his sticky load spreading deep inside me.