Jenny and Uncle Jerry - chapter 2 - Sex Stories

Jenny and Uncle Jerry - chapter 2

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For three months, I had short and strange dates with Uncle Jerry every Saturday night. I'd lay on my back on the sofa or Mom's bed with a towel over my face. They finally let me just use a blindfold during our illicit 'appointments'. I'd spread my knees wide so Uncle Jerry could smell between my legs for a minute or two, then lick me. He usually did it long enough to make me cum. It felt very good, other than the shame and strangeness. I didn't want to think about why, but he rarely said anything, and I only felt his thick moustache between my legs on about half our dates. The idea of Jerry AND somebody without a moustache doing the same was just too disturbing to contemplate. He never hurt me or said anything bad, and always left me candy or some pretty new panties.

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I saw a tear at the corner of Mom's eye as she said, "I convinced Uncle Jerry to wait two years, but it's time for you to be a woman. Let's show Uncle Jerry how grown up you are. Show him you can drink wine." She handed me a wine glass and had one herself. I kind of liked the tart white wine but was surprised she was letting me drink. Mom said, "Open your gift from Uncle Jerry, sweetie." She handed me a small box and I unwrapped it. Inside were five rubber dildos! One of the toys was cylindrical with a rounded tip and only the size of my pinky finger. Most of the others were the same shape in larger sizes. The fifth was very thin, but nearly the length of my foot!

"He's eager to see you make ...

... yourself a woman." She instructed, "Take off your panties and sit on the edge of your chair. Good. Now lick the smallest dildo a little. Get it nice and wet, then spread your legs and rub it on your kitty. It'll make you feel good."

"Mom, I don't know..."

"It's for Uncle Jerry. He's been great to us, so you can do more for him. Nobody else will see."

"I uh... I guess."

I licked the rubber rod and got it wet in my mouth. Mom held the camera and recorded me stroking it against the outside of my freshly shaved slit.

"Very good. Take your time. Try the smallest one inside you first, and keep going until the biggest one is all the way in."

"Eeew! No, Mom! I don't want anybody seeing me do that! I heard the first time hurts, too."

"Uncle Jerry said he'll give us five thousand, once he sees you put the biggest one in your kitty. I'll even give you some of it. Is it worth five hundred bucks to hurt a little bit and be a little ashamed?"

"Well, uh..."

"Five hundred is enough for the new game system you want. How about if you can do it in the bedroom? I won't watch, just the cameras?"

"Well, still, it's SO embarrassing! I don't want to!"

"Okay. Have some more wine. I'll put in a movie."

After drinking two more glasses of wine while watching a porno flick for the first time, I was willing to do it. I masturbated with the smallest dildo and was very aroused. The second would only go in about halfway. Mom said, "It'll hurt a little bit when you take your ...