Jenny and Uncle Jerry - chapter 2 - Sex Stories

Jenny and Uncle Jerry - chapter 2

... virginity and there might be a little blood, but after that it will only feel great!"

I dubiously asked, "You're sure it won't hurt me? Two friends told me their first times were horrible."

"I had a little pain for maybe ten minutes my first time but it wasn't bad, nothing like childbirth. Having you come out of me felt like I was being ripped in half! It was agony! But it was worth it to get you. This won't be anywhere near that bad. Can't you just do this to help me? We really need the money. Rent is due in a week."

Guilt made me give in. "Well... Okay, I guess."

I wetted the round end of the largest dildo with my mouth and tried to slide it into myself. "It won't fit. I can't do it."

"You need to push harder. There will be a little bit of blood, but you'll be fine. Trust me."

As it penetrated my hymen, I felt a major pain down there. "OW! Aaagh! It hurts, Mom!"

"Push it the rest of the way in, then hold it up for the camera. Good, that's a brave girl!"

"Owowow!"

She handed me two pills and another glass of wine. "Take a couple pain pills and get a shower, sweetie. You'll be fine tomorrow." I did, and I mostly was.

There was a mild soreness in my kitty, but the truly bad part of the next day was the hangover from the cheap wine. At lunch time Mom handed me a stack of cash. "Five hundred. Spend it on anything you want. Uncle Jerry liked the video so much he gave you extra birthday presents." She pointed to a laptop computer and pair of ...

... webcams on the desk in the living room, across from the sofa where I usually slept.

"Uncle Jerry says if you keep entertaining him, he'll rent us a better house! If you uh... do all you can to make him happy, Jerry will even get you a car in three months! All you need to do are the Saturday dates and play with the toys in front of the cameras three times a week. We'll close the curtains and I'll go in my bedroom, so nobody but Uncle Jerry will see. You can even watch porn while you do it. Now that there's no hymen in the way, he might put a finger or two in you sometimes. Like all the other times, he won't hurt you."

I felt ashamed, afraid, and a little nauseous. "But.. but Mom..."

"Come on, Jenny. It's for Uncle Jerry."

That had always been a good enough reason before, so I reluctantly gave in. "Okay."

I was quite embarrassed and uncomfortable the first week, but learned to ignore the cameras. Instead of three times a week, I got extra gifts by making myself cum with the toys nearly every night. Mom would usually leave to visit Uncle Jerry when I started, and returned home as I was going to sleep. She kept bringing him my dirty panties too. He visited our little trailer every weekend and played with my body while I wore the blindfold. Most times, he would lick or finger me long enough to make me cum, which was temporarily great. The shame and guilt didn't start until each time he left.

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As far as I knew she had never smoked, but after we finished dinner one ...