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.
"It hurts, it hurts so much," I cried to Jeff. "Please put another one in!"
"Oh no, my little fucktoy," he replied. "I'm not loosening you up that much. When my cock goes into you, you're going to feel it!"
"Oh, god!" I exclaimed. "With your cock, if you put your whole fist in me I'm sure I'd still feel it when you fucked me!"
"Maybe one day you'll find out," he whispered evilly. Then he took his fingers out of my ass and moved his mouth back over my pussy. He bit softly on my pussy lips, but it was still hard enough to send shivers throughout my body.
I felt him kneel behind me, and then he grabbed my hair and pulled my head up. I could see him in the mirror in front of me, holding my hair in his fist like he would the reins of a horse. I liked the image, so I whinnied lightly.
"Oh, you like playing the mare?" he asked.
"It's only appropriate," I panted, "considering that I am about to get mounted with a horse cock."
"Look at me," he said seriously. "Look at me and tell me what you want."
I looked right into the reflection of his eyes and I said, "Fuck my ass. Shove your huge cock right into my stomach. Use my ass for your pleasure. Don't show any mercy. Just fuck the ever living shit out of me!"
And he did. He shoved his hips forward and speared my asshole. He didn't slow down for a second. He rammed his cock right into me. I don't think I've ever felt anything as painful in my life. He had lubricated his cock, but it was too large. It ripped through me, and I could feel it lacerating my insides. It hurt so much that it even took the sexual edge off. But only for a second.
He was right to have me watch him. I watched him bury himself in me. I watched the pleasure that it gave him. I realized that he was using my pain for his pleasure. And it got me so hot, so fast, that I couldn't believe it.
Once his cock was buried to the balls in my ass, he started fucking me with shallow strokes. The feel of his cock pulling back and forth on my sphincter was painful and amazing. I could feel the head of his cock moving back and forth deep inside me. And then he pulled my hair back hard, forcing me to rear onto my hands, and he grabbed a nipple ring in his hand and pulled.
Once again I was feeling pain from multiple places, my nipple, my scalp and my ass, and once again I felt the ball of pain turning into a ball of pleasure. He wasn't even touching my clit, but I felt it pulsating. I bent my head down to look between my legs and I could see my pussy juice dripping onto the bed. As an added benefit, when I bent to look, it pulled my hair even harder.
I reared my head back up, looked right into the reflection of his eyes and screamed, "Fuck me harder! Fuck my ass harder!" He did, shifting from shallow strokes to deep ones, which pulled the head of his cock right to my sphincter, causing me more pain, and exponentially more pleasure. I think it was the third stroke again that I started cumming. I screamed and dropped my head to the mattress, pulling my hair again and not caring. I shot a hand to my clit and pinched it between fingernails, abusing the same spot he had already bitten multiple times.
I shuddered as I came even harder and my body collapsed, surprising Jeff and causing him to fall hard on top of me. When he fell on top of me it drove his cock even deeper then before. I was sure that he had to be damaging something internally, and I didn't care. I was coming so hard and my ass was squeezing his cock so hard, he could not move, but the pulsations caused him to start cumming anyway. I felt his cock growing and pulsing, though I couldn't feel the hot cum the way I had in my pussy and my mouth. I had probably already drained most of the cum from him.
Jeff was collapsed on top of me, but I continued to come around his cock. I was still pulling at my clit when Jeff pulled my hand out from under me and held both wrists over my head again. "You're done when I'm done," he whispered in my ear.
"But I'm still cumming," I whined.
"What kind of slut would take a brutal ass fucking and not be able to stop cumming?" he asked me.
"Your slut!" I cried.
"Good answer," he said, and with his other hand he reached under my chest and pulled on my nipple ring while simultaneously pinching my abused nipple. At the same time, he started fucking my ass again with his cock, which had gone down a little, but was still quite firm. He pulled back until the head almost popped out and then pushed back in. Just a few strokes of that, combined with the nipple abuse, and I was cumming even harder. Finally he pulled all the way out of my ass and gave my ass a really hard slap. It was like a switch, and I finally finished cumming.
I collapsed on the bed, and he collapsed next to me. We both lay there breathing heavily for a few minutes, then I felt his hand start fondling my ass again. "I've taken all of your cherries," he told me. "I haven't left you anything to give to anyone else. How are you going to feel when you find the person you want to marry, and you have to tell him that there is no more virgin territory for him?"
"I'll tell him that I lost all my cherries in one night of amazing debauchery," I said, "and if he works real hard, in a month he might be able to make me cum as much as I came in that one night, but only if he is really good."
Jeff laughed and kissed my neck as he slipped two fingers into my gaping asshole. "Oh, don't start again," I begged. "If I get going again, I'll never be able to stop cumming!"
He laughed again and knelt next to me. "Stay right there," he said. He walked out of my room, and I just lay in the bed, only half conscious.
In a little while he was back, rolled me over onto my back and lifted me into his arms. I wrapped my arms around his neck and murmured, "Where are you taking me?"
"I'm taking you downstairs," he said. "I called the football team and they are all waiting to gangbang you."
"Mmmmm, I'll do anything you want," I told him, kissing his neck. Instead of taking me downstairs, however, he took me through my mother's bedroom into her bathroom. My mother has a large Jacuzzi, and he had filled it with warm water. He gently placed me in the tub and then climbed in behind me. He turned the jets on and pointed them at my abused body. He shampooed my hair and then rubbed a soap-filled washcloth all over my body. The coarse cloth rubbed my body deliciously.
When I was all clean he quickly washed himself, then got up and left the room. In a few minutes he came back and had me stand up in the tub. He drained the tub and dried me off. Then he picked me up again and carried me back to my bed. He had stripped the bed and remade it with clean sheets! He laid me down on the bed and kissed my head. He put the required antiseptic on my nipples and covered me up. He slipped into the bed, spooned up behind me and kissed me good night. Just before I fell asleep he whispered, "Welcome to your new life, Rachel."