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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 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 night, Mom took a pack of cigarettes from her purse and set a lighter on the table. There were two cameras recording us already, but she held another as she said, "Smoking is unhealthy, stinky, and wrong, but Uncle Jerry wants to see you try it. Take the plastic wrap off the pack slowly and take out a cigarette." She recorded me as I did.
"Good, now smell the cigarette and touch your face with it, nice and slowly." I sniffed it and detected menthol and a few other aromas, then moved the tip around my face like she asked. "Go ahead and light it. Suck on the filter just a little to get it started, but don't breathe it all the way in."
As the lighter flame touched the tip I took a little smoke in my mouth and blew it out. I thought it tasted awful and fought the urge to cough. "Good, sweetie. Just take a little more smoke in your mouth like that and blow it out. Show Uncle Jerry you can do it."
I didn't really want to, but it was for Uncle Jerry. She recorded me pretending to smoke. "Good, Jenny. Have another glass and another cigarette." I liked the wine, but not the smoke. I complied, to make Uncle Jerry happy. By the end of my second glass I was feeling quite tipsy.
Mom said, "Uncle Jerry wants to keep watching when you play with yourself at night, and he wants to see you smoke a cigarette too, just three cigarettes a night. Do you think you can do it for Uncle Jerry?" I coughed as I exhaled my last puff. "Ach! It tastes so bad! But I guess, for Uncle Jerry." Only two weeks later, I liked to smoke and was up to half a pack a day. I especially liked to smoke while I masturbated for Uncle Jerry. I also enjoyed smoking with his face between my thighs on our next couple of 'dates'.
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One afternoon Mom said, "Tonight we're going to visit Uncle Jerry's house. He finally wants you to meet him. Do your hair and makeup, but don't shower or use perfume. Jill your kitty a while first, then wipe your fingers on your neck so he'll enjoy the way you smell."
"But, Mom..."
"Make him happy tonight, and he'll give you a car tomorrow. Imagine it, a car of your very own!"
"That would be so great!"
Learning to smoke, masturbating in front of cameras, being licked by multiple strangers, and giving a strange man my filthy underwear had been freaky and frightening.
I was nervous, but eagerly anticipated my reward.
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