At fifteen he had barely begun dating himself. The entire concept of his parents dating was foreign to him.Jessica’s eyes widened at this. “Oh, we...l, I mean, I always knew your father. We grew up together and went to school together from the first grade on. Still, I didn’t officially ‘date’ him until I was about Toby’s age or so. I guess we were sixteen, although he was a few months older than I was. It’s been about twenty years or so.”“Was he the first guy you ever dated?”“Oh, no. I started. But then she said "this is DARE time". I was like "really?", she laughs. Then she said. "I dare you to plow the snow without any underwear on". I confidently said "That's it? For sure." "But after, you'll join us downstairs and you'll wear your compression underwear and your pajama top" she added. "WTF?!" I said. She already was thinking what I was about to, my penis will shrink further down to nothing in the cold and then I have to wear tight underwear after. I was right. Soon after I plowed. More

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