His Pain, My Pleasure - Summer of '88 - Part 2

by Matt B.

I couldn't take my eyes off of Brian's naked bottom. His two round globes were sticking straight up, awaiting their fate. It was very erotic for me having this 10-year-old over my lap, his shorts and underpants bunched up around his ankles. I was wearing shorts also, and I could feel his little, smooth dick and balls against my bare knee.

With one arm tightly around Brian's waist I placed my other on his bare bottom and began to rub and knead it. He was nervous, but his nether regions were relaxed, and this allowed me to spread his cheeks and see his little, pink anus. I had never seen another boy's butthole before, and I rubbed my fingertip over it, watching it pucker as I did so.

I raised my hand high and brought it down across both cheeks of Brian's butt. "Aaaaahhh, please, no more!" he begged, already starting to cry. I smacked his bottom even harder and after five swats he was wailing. As I continued he was kicking his legs fiercely. I covered ever last inch of his bare buttocks, deeply reddening the entire area with my hand.

Brian was sobbing, and i knew he was pretty sore and would be for quite awhile. Lifting him off my lap I noticed his erection was gone, probably due to the pain if the spanking. He was crying uncontrollably and I knew it would probably be several minutes before he regained his composure. I gently pulled him back to me, standing him between my knees. I took his little penis between my thumb and forefinger and began to rapidly stroke it. He looked as though he was enjoying it, and stopped crying sooner then I thought he would. After several minutes he had a little-boy orgasm, although nothing had come out.

I pulled up Brian's shorts and patted his little bottom. My vacation lasted two weeks, and everyday Brian would come over while I was sitting out back. I would pull down his shorts and underwear and spank him until he howled. He didn't enjoy the spankings, but he did enjoy my masturbating him after each one.

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