Ass up.”He slowly indulged my demands., pushing his back up in the air using his forearms on the bed. I untied his wrists, and pulled them back so they were behind his thighs, at his knees. I clasped them together with a pair of cuffs. I squirted some lube on his asshole. I could hear him whimpering. “Breathe pet.”I looked down into my box of toys. Small ass plug? It would go in easier. But so much less fun than watching him writhe. I settled on a slightly larger plug. I squirted some lube on it. I reached around and started stroking his beautiful 8” cock. I wanted to ride it. But first I wanted him to be too ashamed to brag, and I wanted him to be properly broken. He’d come back and beg me to degrade him if I broke him properly. I pressed the ass plug against his asshole. Running the tip up and down his virgin crack, I could feel him twitching. I slowly came to a stop pressed against is asshole. I applied a fraction of pressure. Just enough to spread his ring a little. I felt his. Lucy's pissed that I don't have a job yet and I'm running out of money. It sucks!"I hold him tight and offer my sympathies."Les, I have been there and done that buddy. Your luck will change and this situation shall pass and your young life will be so good in a short while, you'll wonder why you ever worried about it!"."Well I sure miss our 3sums. I liked sucking cocks with you while Travis fucked me".I chuckle and ask "How did it cum to pass that you like to be fucked?" Well, since I know you won't tell anybody, here is the scoop".Seems as a teenager when he first started jerking off, his anus was of much interest to him. He would rub his fingers over and all around it and slip a finger or two inside. He luv'd poking his fingers in and out. It added to his ejaculation.His next door neighbor's k** came on to him a couple of years ago. They would jerk off and suck each other and one day he asked Les if he could fuck him. Les agreed and they did that a dozen times or so. He had a small.
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