Chapter 7: The First Cherry

As I helped Rachel into the car, she went out of the way to give me a nice view of her pussy. On the way home, she was quiet for a while, but she soon broke the silence by saying, "We agreed on no permanent marks."

"They aren't permanent," I said. "The holes will close shortly after you remove them."

"You are crazy if you think that I will be giving these up when this is over," she said with a smile. "These are on for good!"

"Ahhh, well then, that's your choice," I told her. I thought for a moment, and then I added, "Of course, I may remove them from you before our time is over, which would mean you would have to get re-pierced if you wanted them back." I could see her shiver in her seat.

We both remained silent until we got back to her house. I stopped at her front door and kissed her lightly on the lips. "Go inside," I told her. "Go upstairs, straighten up your room and strip naked. Then I want you to go to your mother's room and get her tripod, camcorder and the longest blank tape that you can find. Set up the camera facing the bed, press the record button and get onto the bed. Then wait for me.

"Don't play with yourself. Don't touch your pussy. Don't fondle your new rings. Just wait. When you hear me coming up the stairs, you will know that I am coming to take you. When I walk into your room, I want you spread on the bed, your legs wide, offering yourself to me. Do you understand?"

"Yes," she whispered as she nodded. I gave her another little kiss and pushed her into her house. I walked back to my house, and Michelle was in the living room, practically bouncing up and down with excitement.

"I saw you pull up! Janice called me, but tell me everything that happened," she said eagerly. Part of the deal that we made was that she would help me, and in exchange I would tell her everything. She would be a partner with me in the Humiliation and Degradation of Rachel Miller.

I sat down and told her everything, in as much detail as I could. My story was punctuated by gasps and exclamations from Michelle. It took about ten minutes to finish telling the story, and Michelle was squirming in her seat by the end. I could only imagine what Rachel was feeling, lying in her bed right now.

"You had her set up the filming of her own deflowerment?" she asked. "You are truly an evil genius!"

"I try my best," I responded with all humility. "Well, I think she's waited long enough. I'm going to head over there to do my duty."

"Hah!" Michelle exclaimed. "Your duty! As if you won't enjoy it!"

"If it must be a duty, I might as well enjoy it," I replied. "I suppose you are going to be waiting quietly to hear all the gory details?"

"Fuck no!" she cried. "Your big sister is going to go upstairs and find her biggest dildo and fuck herself senseless for the rest of the night! But you'd damn well better come and find me first thing after you get home in the morning!" She reached over, gave me a kiss on the cheek and marched upstairs towards her bedroom. As if what awaited me next door wasn't enough to get my engine revving, now I had the image of my sexy sister plowing her cunt with a big dildo bouncing around in my brain. I sighed and headed back to Rachel's house.

I had been lying on my bed for hours. First, he had me prepare my room for my de-virginization. Then I had to walk through the house, nude, to get my mother's video camera. That was embarrassing on so many levels! I had never walked through the house with no clothes on before. Then I had to go into my mom's room and wander around naked. Finally, I had to retrieve and set up the video camera! Jeff was going to tape himself taking my virginity. And probably, based on what he had said earlier, taking all three of them!

Then there was the waiting. I didn't know what he was doing or where he was. All I knew was that I was wet and waiting and he wasn't there. It had to be at least six hours, despite the clock telling me it was only fifteen minutes. Have you ever tried lying on your bed, horny as can be, and unable to touch yourself. I wanted to cheat, and then I would look up and see the unblinking red light on the video camera. I knew that if I touched myself I would be punished. Was it worth it?

Then I heard it! I heard footsteps on the staircase. Jeff was coming for me! This was it! The door opened and Jeff walked in. I stared as I saw my first real-life erect cock. Jeff was gloriously naked and scarily huge. "He's going to kill me with that," I thought. There is no way it would fit even if he was gentle and worked it in slowly, but I knew he wouldn't be doing that. He was going to take that bat between his legs and he was going to shove it into my stomach through my cunt. Oh god, what had I gotten myself in for?