Chapter 9: The Third Cherry

I couldn't believe how dirty I felt. I was walking into my mother's room with no clothes on, cum dripping down my legs. As I was picking up the new tape, I saw a drop of cum drip off me and onto my mother's shoe. I thought about what Jeff had said: "you may scoop it up." I shivered as I walked out, leaving the spending of my first sex on my mother's shoe.

I went back into my bedroom and I changed the tape. Jeff was already asleep. He looked so sexy, lying nude in my bed, surrounded by all my things. He looked like he belonged there. I shivered again, this time in anticipation. Before I walked out, I remembered what he had told me was going to happen next; I repositioned the video camera and my full length mirror, so that nothing would delay the inevitable later.

I went downstairs, still nude. All the window shades were open, and I was traipsing through the house in the altogether. Admittedly, we were a little set back from the road, and our neighbors were far enough away that they weren't likely to see into our house in the daylight, but it could happen. Someone could see me as they walked by. Or someone could come to the door. I rubbed my pussy a little bit thinking about it, and then I licked my fingers off.

I went to the fridge to see what we had, and realizing that we were going to be eating on my bed, I made a little picnic with assorted sandwiches. I got some chips and drinks and brought everything upstairs. Jeff was still napping, so I set everything up as well as I could. As an afterthought, I got some candles and spread them around the room before I lit them.

Finally it was time to wake Jeff up. I crawled onto the bed between his legs, and took another good look at what he had. I had seen pictures on the internet before, but this really was my first real cock. I had been so scared when he walked through the door, his cock leading the way. It was so large and scary. And now it was small and cute. I don't think it would be a good idea to use those words to his face, but it was. It was small and squishy, with wrinkles everywhere, the head sticking out the top like a spear tip. Nothing like the rod that I had felt shoved through me.

I held it between my fingers and licked the head. I know that a lot of my friends thought that it was gross, but it was beautiful to me. It didn't have a lot of taste now, but before, when it was seasoned with my juices, his cum and my blood, I could definitely taste it. And it turns out that I love the way his cum tastes. I wondered how others' will taste in comparison. Given what he agreed to do for me, I knew that I'll be tasting others.

I popped his whole cock into my mouth, and I realized that now it fit in completely. However I could feel it growing in my mouth, and I knew that soon it would not fit. Or at least not for a while, because if I were to become an expert cocksucker, I'm sure that deep-throating would have to be in my repertoire.

I moved my head up and down until I heard him say, "Now that is a beautiful way to wake up."

I popped his cock out of my mouth and put my head on his leg, looking up at him as I ran my tongue around his cock. He smiled at me and said, "Stop that, you vixen. That is not next on the agenda. Now feed me!"

I sat up and got the food, and we ate quietly for a few minutes. I could see the thoughts flowing over his face, and I knew what he was thinking, when he finally broke the silence. "Rachel, I need you to tell me how you are really feeling," he said.

I looked at him for a moment, very seriously, but I could not keep it up. I jumped up and sat right next to him, wrapping my arms around him. I kissed his cheek and said, "I am amazed. I told you about my fantasies, I told you how I wanted to be treated, but I was expecting to be disappointed. After all, how can reality live up to fantasy? But it's better!

"When I am fantasizing, I always know what is coming. I always project how it will feel. But today, I didn't know what was coming. Even when you told me what to expect, I didn't know what to expect. You pushed me, and you hurt me, and you embarrassed me, and I have never been so sexually satisfied in my life. In a few minutes, you are going to take my last cherry, and my asshole is itching for you.

"I've seen your cock hard, I've felt it in my mouth and up my cunt, and I know that there is no way in the world that it is going to fit up my ass, and do you know what? I don't care. Shove it in dry, and I'll take it.

"I wanted this before. I knew that I wanted you to show me what my fantasies really could be. But now I want it more. My only problem is that I think that you are going to ruin me for every other man."

I kissed him, and then I went back to my place and took another bite of my sandwich. He was looking at me, stunned. I smirked at the thought that I had caught him off guard. He finally shook his head and said, "A month from now you should remember, you pushed me to this."

We finished the meal in silence, and when we were done I collected the remains and walked back downstairs, still naked. The sun was setting, and the lights in the house were on, making it more likely that someone would see me, but I didn't care. I finished putting everything away, and then went back upstairs. Jeff was propped up in bed, looking at me as I walked through the door.

I went to the video camera and turned it back on then I climbed onto the bed and knelt at his feet. "I'm ready to give you my last cherry, Sir," I told him. I saw his cock twitch when I called him Sir, and I knew I had found one of his buttons.

He smiled at me and said, "Go to the bathroom, pee and clean yourself up, then come back here."

I went to the bathroom and did as he asked. I scrubbed as much of his cum out of me as I could, and used a wet washcloth on my asshole as well. I wanted to be squeaky clean for him. When I was done, I went back into my room for further instructions.

Jeff had me get back onto my bed on my hands and knees, facing the mirror. He knelt behind me, running his fingers along my ass and hips. I felt Jeff start kissing my ass cheeks. I felt his tongue go down my thighs, then back up, swiping at my pussy.

"Mmmmm, it's much better fresh," he said.

He started licking my pussy in earnest. He licked all around, dipping his tongue into my slit then moving it down to my clit. I buried my face into the mattress in front of me as I jutted my ass further into the air, trying to get him to go deeper. He took my clit into his mouth and bit it. It hurt, and I almost came. Then he moved his tongue back up into my cunt, and then he moved it even further up, running the tip around the rosebud of my asshole. It was so nasty.

Just the thought of him putting his big cock up my virgin asshole had me on the verge of cumming. Wait, let me correct that. Every god damn thing he had done today put me on the verge of cumming, with the exception of those things he did that actually made me cum.

His tongue moved back down to my swampy cunt, then pulled away. I felt his lips around my clit, and then he bit it again, while at the same time sinking a finger into my ass to the second knuckle. It was a good thing that my face was in my mattress, or his parents might have heard me scream from next door. His tongue moved back between my lips as he sawed his finger in and out of my ass. He pulled the finger all the way out, and then pushed it back in even deeper. He repeated this maneuver a bunch of times, driving me absolutely insane. Then I groaned even deeper as I felt two fingers being forced into me.