One of my best babysitter sex stories involves a very shy man.
I’ve got a lot of babysitter sex stories, but this guy was so, so painfully shy. The painfully shy where he’d stutter and pretend he wasn’t looking at my short skirt.
It didn’t help him that I often refused to wear panties underneath it. I found him to be quite sexy, stammering, polite. He was exactly the sort of man I wanted to fuck and dominate. But he wouldn’t do anything to me, blushing and stammering when I caught him trying to get an eyeful.
Finally, I took matters into my own hands. In the tightest top I could get, I put on a miniskirt to match.
Since this was a con-mission, I didn’t wear any underwear.
Once I got to his house, I played with the kids and tucked them in bed. I feigned sleep as I lay flat on his couch, my legs spread wide and giving him a full view.
Soon he made his way home, and his briefcase dropped to the ground as he spotted me. I could hear him moan to himself, the sound of his feet hitting the ground, drawing closer. I shifted a little, moaning like I was sleeping.
He took the bait. Immediately, fingers made their way to my pussy, just stroking my clit. Soon, his cock pressed against my pussy, and he forced his way in. I pretended to wake up, but he just shushed me.
“Just take it, Elise,” he whispered and covered my mouth as his hips snapped. He continued to pound into me, driving his cock deeper and deeper into me. It didn’t take long for him to cum, gasping as he emptied himself inside me.
After that, he was never shy again.
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