Massaging My Babysitter

My parents continued to get a babysitter for my sister and me when I was already 12 and 13. My sister was only 7 so they justified it due to her being so young. The truth was that I was sort of irresponsible. Our sitter for several years was Freddie, a boy we knew from church, two or three years older than me. Freddie and I had seen each other's privates from time to time when we changed clothes, so we were sort of relaxed in that department.

I discovered sperm production during seventh grade and eased into a jacking schedule of three times a week. There was one peculiar thing: now that I was shooting loads of cum I occasionally had dreams involving Freddie and his nude crotch. These dreams had a sexual component and frequently ended with me waking up with an intense erection in my pajamas.


On this particular occasion my sister was already sleep. Freddie and I had been wrestling but were winding down. The wrestling had given me a boner and if I wasn't mistaken, Freddie had one also. Completely out of nowhere I heard myself say "Let me give you a massage." This was not planned, it just popped out.

Freddie was agreeable. He lay on my bed in nothing but his boxers and I rubbed him from head to toe, except for that unmistakable lump in his underwear. I had never had any sort of physical relationship with him or anybody else, but now I knew without a doubt that I was going to give Freddie a treat.

I rubbed closer and closer to his groin. He made a sort of "Hmmm" sound. Did that mean "go ahead" or "get your damn hands off of me?" I had no idea. Soon it was too late to stop. I was tickling the bulge where his dick made a ridge in hs boxers. "Hmmm" he said again.

Now I went for broke, surrounding his bulge with my entire hand and slowly sliding back and forth. He stretched out a little straighter in the bed.

Now he voiced a question: "Do you know what you're doing?" I told him yes and kept the rhythm going. Back and forth, back and forth. My hand was separated from his dick by a single layer of cloth. I told him I was going to get his thing out so I could massage it better. He asked if I was sure I wanted to. Again I said yes.

It took a little fishing to get his erection out through the slot. Then I was stroking him hands-on. I was so aroused that I could feel cum seeping out of my own dick.

Freddie was making noises by then, the peculiar high-pitched sounds of an adolescent male heading for a climax. I didn't rush, didn't hurry him, just kept my hand moving at a steady speed. I was 13, I'd never done this to anybody else. Freddie was totally into it and I was trying to keep my hand steady. I was thinking all those thoughts when Freddie whispered "Coming!"

A second or two later he produced the only ejaculation I'd ever seen besides my own. His first load of jism landed high on his chest and then his body pulsed again, releasing a second load. And then a third.
He raised up in the bed, reached inside my underpants and pumped my stiffie. I was so horny that I began to feel the climax while he was still reaching for my dick. Then I exploded beyond any of the orgasms I'd had alone.

We were wiping off our dicks when Freddie gave me an amused look and said "Hell of a massage!"

The experience put a whole new meaning on "Babysitter." Any time my parents called Freddie I knew what the high point of the evening would be.

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