Chapter 2

For the previous year, I’d 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 pillow or towel over my face, so I couldn’t see. I’d spread my knees wide so Uncle Jerry could smell between my legs for a minute or two, then lick me for several minutes. He rarely 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.

Jerry never hurt me or said anything bad, and always left me candy or some pretty new panties.

I saw a tear at the corner of Mom’s eye as she said, “You’re sixteen, and 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. I convinced him to wait two whole years, but it’s time now.” She instructed, “Take off your panties and sit on the edge of your chair. Good. Now lick the smallest dildo a little, 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 ... 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 hairy 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 a pill and another glass of wine. “Take a pain pill 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.