Diary of a Teenager Ch. 01

Freddy ended up fucking her twice more that afternoon. I got a lot of good views of his cock sliding in and out of her pussy from all kinds of different angles. I think the nastiest was when she rode him facing me while squatting over him. Her pussy lips were spread wide among her hairy red curls. I could see her clit protruding from her cunt. Watching his huge cock disappear into her belly, and the desperate expression of pleasure on her face just added to the sexuality of the picture in front of me.

After they finished fucking, Judy sucked his cock for at least twenty minutes before he finally unloaded one last time. She let the cum drool from her mouth and drip from her chin right in front of the camera. I had the rubber penis deep in my own cunt and had several more good cums. My panties were a mess when I finally left for home two hours later.

Judy let me keep the rubber penis, which I named Shane, and I went home and fucked myself silly. I even took a long hot bath where I used Big Red and Shane at the same time to fuck my pussy and ass. Now I'm getting ready for bed and think I'll do a double again before I fall asleep.

September 21

Dear Diary,

I thought this day would never arrive. I have so much to tell you that I hardly know where to start. Since I knew that Shane had invited me over to study, I dressed very carefully. First I put on some sexy underwear that I kept hidden from my mom. My bra and panties were matching blue silk which accentuated my breasts, ass and mound (Diary, I'm just going to call it a pussy after what happened today - I hope you don't mind). I put on a white miniskirt with a sleeveless yellow top. I spent a long time on my hair and make-up until everything was perfect.

I decided to forego my usual workout with Big Red that morning. It was hard to keep from touching myself during the day. My pussy missed the regular stimulation it normally received. By the end of the school day my body was overcharged with sexual energy. I met Shane at his car after school and we drove to his house. On the way he told me some funny stories and I laughed nervously. He told me to relax, but my stomach was in knots.

No one was home at Shane's. We put our books on the kitchen table and he made a snack. I couldn't eat. He kept trying to get me to relax by telling jokes, but he was failing miserably. I knew I was about to blow it once again and wouldn't get another chance. I told him I couldn't stay too late and we should get started.

Shane pulled a chair right up next to me at the kitchen table. As I started walking him through some problems, he scooted even closer. His thigh pressed against mine and I could feel it burning into my skin. I felt my nipples getting hard and my pussy getting gooey. Then, as I was leaning over the table to show him an example in the book, he put his forearms on the table parallel to the edge and leaned forward to watch. Well his elbow pressed against the side of my breast. My head started spinning and I began to stammer. He turned to look at me, only this time I could feel his elbow pressing harder into my breast. He moved his face closer, looking into my eyes. This time he moved his elbow in small circles gently massaging my left tit.

Our lips met. My mouth responded automatically, opening to his tongue. He dropped the arm pressing my breast until his hand rested on my bare thigh. With his free hand he cupped my other breast, gently squeezing and rubbing it with his fingers. He started sliding his other hand up my leg extending his fingers down the inside of my thigh. I spread my legs, opening myself to his touch. It was almost like I was dreaming. My body just responded as though it had been trained for precisely this moment.

My pussy was on fire and I knew I was going to explode at any moment. Shane slid his hand under my top and into my bra so he could feel my bare tit. His thumb and forefinger found my nipple. That was all it took to send me over the edge. He pressed his hand into my pussy just as I exploded. I started humping against his fingers, lifting my ass off the chair while juices poured out of me and drenched my panties. I was gasping for air and biting my lip as my body thrashed about. My orgasm must have lasted a good thirty seconds before I was able to catch my breath.

I was totally embarrassed and felt like running from the house. Shane pulled me to him and hugged me saying really sweet things to me until I felt better. Then he got me a glass of water. We were standing in the kitchen when he put his hand on my cheek and asked if he could kiss me. Before I could react he leaned forward and our lips met. His hands went around my waist and he pulled my body tight against his.

Once again my body took control. His gentle kiss turned passionate as our tongues lashed out at each other through our open mouths. Our bodies ground together and I could feel his hardness pressing into my lower belly. His hands moved down over the cheeks of my ass while I straddled his leg, rubbing my pussy mound against his muscular thigh.

I wanted him to fuck me so badly, but I was afraid to make the first move. I felt his hands move up my back lifting my blouse. I raised my arms and let him remove it and drop it to the floor. Then he reached in front of me and unsnapped my bra while staring into my eyes. He dropped my bra onto my blouse. He pushed me away and stared at my naked breasts. He told me they were beautiful. I could feel the pressure of my engorged nipples puffed out and pointing upwards. When he reached out and touched them I gasped and thought I was going to have another orgasm. I stayed right on the edge while he gently fondled me and rubbed my sensitive nipples. When he leaned over and sucked my tit into his mouth I lost it. I grabbed his head and squealed out loud as my pussy gushed into my panties in a short but intense orgasm.

Shane ripped off his shirt and pulled my naked breasts to his muscular chest. We resumed our kissing. He wedged his hand between us pressing his hand into my pussy through my skirt. I started moaning as I humped against his fingers. With his other hand he unzipped my skirt. We pulled apart briefly to let it drop to the floor. I was naked except for my sandals and blue panties with a dark wet spot over my slit.

We resumed kissing. Shane slipped his hand into the back of my panties, spreading his fingers across my ass cheeks and pushing his middle finger down my crack. He reached down under me until his fingers slid over my hairy mound and the tip of his finger found the steamy folds of my womanhood. Several fingers rubbed across my slit before disappearing inside me. I was on fire, moaning heavily and humping myself on his fingers which plunged in and out of me.

I was getting ready to cum again but wanted something more inside me. I reached down and grabbed the hard bulge in his jeans, rubbing my hand up and down its length. Then someone else started talking, but the sounds were coming from my mouth.

"Fuck me, Shane. Fuck me right now. I need your cock in me. Hurry. Please."

In a flash he unfastened his jeans and pulled out an eight-inch cock. I quickly shed my panties. He spun me around so my back was against the counter. He bent at the knees and placed the tip of his cock against my steamy opening. I pressed down against him at the same time he thrust upward. I felt his cock bury itself deep inside me. When he started to fuck me I had another orgasm. I clenched the edge of the counter and threw my head back, grunting, gasping and squealing as I came in waves. He grabbed my hips and continued pounding my pussy, which was gushing all over his cock and making a mess of our pubic hair.

When I finally caught my breath Shane pulled out of me and asked if I was on birth control. When I said no he said we should go back to his room so he could get some protection. Once again some other person started speaking through my mouth.

"I've got a better idea. Let me suck your cock. You can cum in my mouth."

I squatted in front of him and quickly put my lips around his glistening manhood. I was gentle at first, not sure how a real cock would compare to Big Red. I gained more confidence when it seemed like he was enjoying it. I swirled my tongue all over the head as I bobbed up and down on him. I took him into my throat, a little at first but then more and more until my mouth was pressed to his pubic hair on each thrust. Sometimes I would hold him deep inside me and use my throat muscles to stimulate him.

Sucking him was getting me excited again. I started rubbing my pussy while I continued bobbing up and down on his cock. I began to moan as my excitement level rose. Shane put his hands on the back of my head and literally fucked his cock in and out of my mouth. I was getting close to another orgasm when I felt him swell. A warm, sweet tasting liquid splashed against the back of my throat. He kept squirting and squirting, filling up my mouth with his creamy fluid.

While he was still pumping cum into my mouth my orgasm began. My pussy started to gush and I gasped for air. I was unable to keep him in my mouth. I felt something warm splash against the side of my face. His cum drooled freely from my lips, dripping from my chin onto my tits. My fingers were working my clit as my pussy continued to twitch and gush. I had to sit down on the floor until my orgasm subsided and I was able to catch my breath.

I actually liked the taste of his cum and swallowed what was left in my mouth, then licked my lips. I looked up at him and started rubbing the rest of his cum into my tits as though it was hand lotion. All sense of embarrassment was gone. Oh Diary, I felt like such a slut, but I was loving every second.

Shane said we should go back to his room where it would be more comfortable. Shane stripped off the rest of his clothes and we walked back to his room stark naked, kissing and fondling along the way. I didn't feel the least bit of shame.

Once in his room he asked me to sit on the edge of the bed. He dropped to his knees and spread my legs. He scooted between them and pulled my lips to his. As we kissed he fondled my breasts. He trailed his lips down my neck, then across my breast and over my nipple. His tongue flicked across the swollen tip sending flashes of pleasure through me. He sucked me into his mouth, massaging my nipple with his tongue while fondling my other breast with his fingers. He moved his mouth over my other nipple for a repeat performance.

When he was finished sucking my tits, Shane pushed me back on the bed and started kissing down my stomach. I realized I was about to get my pussy eaten. Oh god, Diary, I had seen it done so many times on the video but it was the one thing I couldn't practice with Big Red. When his tongue flicked across my pussy lips and over my clit I thought my head would explode. He opened his mouth and clamped it over my pussy, sucking on it while he fucked me with his tongue.

I grabbed the back of his head and started humping his face just before the dam released. I squeezed my nipples and screamed out loud as my body thrashed about in a tremendous orgasm. Shane lapped up the juices as they poured from my cunt. I must have thrashed about and screamed out for a good minute before I was able to regain control. I felt drained afterward as I lay there catching my breath. Shane climbed up next to me and held me. We just lay there gently kissing and hugging.

I looked down and realized his penis was fully erect. I curled my fingers around it and started stroking it slowly. Then I lowered my head and put him in my mouth. After sucking him for several minutes, Shane handed me a condom. I slipped it over the head of his cock and rolled it down the shaft. I swung my leg over him, guided his cock to my steamy cunt and slowly impaled myself onto him. I leaned forward and started thrusting my ass up and down, repeatedly impaling myself on his cock and grinding my pussy hard against him on each downstroke.

Shane was squeezing my tits and pinching my nipples. I closed my eyes and had visions of the video, which showed a close-up of a girl's ass and cunt as she rode the cock that slid in and out of her. A series of small orgasms washed over me. I was squealing and gasping as I continued ride his cock into bliss.

Shane rolled me off him and mounted me from the top. I wrapped my arms and legs around him as he slipped his cock back into my steamy cunt. I could feel him deep in my gut every time he slammed into my juicy hole. I was out of control as one orgasm followed another. Trash started spewing from my mouth as I begged him to do all kinds of nasty things to my pussy. Shane increased his tempo and was slamming me hard when he grunted loudly and filled his condom while his cock was deep in my belly.

He finally pulled out as his cock began to deflate. I reached down and removed the condom, letting the cum drain onto his cock and balls. I lowered my head and cleaned him with my lips and tongue. I stayed there kissing and licking his deflated penis until it finally began to stir with new life. Shane pulled my legs over his head and started munching and licking my cunt. I continued sucking his cock until it was fully erect and ready for more action.

I rolled another condom over its length, and then crawled forward until I could stuff it back in my cunt. This angle applied new pressure to my pussy sending me into another prolonged series of orgasms. I wanted more so I reached behind and shoved my middle finger up my ass. By this time I was really out of control and cumming in buckets. Shane pushed me forward onto my knees, and then entered me from behind. He shoved two fingers up my ass as he hammered my pussy with his cock. I was squealing and screaming with pleasure, totally out of control. I vaguely remember begging him to fuck me in the ass. He pressed me face down on the bed, straddled my legs, spread my cheeks and guided his cock against my asshole. He entered me slowly and buried himself deep in my bowels. Soon he was fucking my asshole hard and fast. I reached between my legs and rubbed my clit until another orgasm washed over me. Shane continued to hammer me until my orgasm finally subsided.

I begged him to cum in my mouth again. He pulled out and removed his condom while I rolled onto my back. He straddled my tits, waving his throbbing manhood in my face. I opened my mouth and he just slid in, fucking my face as though it were a cunt. I wrapped my hand around his cock and used my tongue to stimulate him. It paid off several minutes later when his cock swelled and gushed several generous squirts of cum into my mouth. This time I swallowed it all, then continued to suck him until he was fully drained.

It was getting late so Shane drove me home before my parents arrived. When he kissed me goodbye in the driveway, things got out of control and we ended up in another groping and fondling session. I had his cock in my hand and he had two fingers in me when I decided I needed more. I swung my leg over his lap and guided him into my pussy. I rode him hard right there in the front seat in broad daylight. When he slipped a finger up my ass I started gushing all over his cock as my body shook with a huge orgasm. I felt something warm spreading through my cunt and realized he had just cum inside me. I didn't care at that point. I climbed off him, kissed him on the cheek and ran into the house with his cum streaming down my legs.

I should be all right since I just had my period a few days ago, but I gave myself a good douche anyway.

September 23

Dear Diary,

After losing my virginity to Shane, I was nervous about going back to school. I wasn't sure what to say to him, and I thought everyone would be able to tell I wasn't a virgin anymore just by looking at me. Well, Judy knew because I called her and described every last detail. Then she told me about doing it with two guys at the same time. We both fingered ourselves crazy exchanging sex stories. When I showed up at school, Shane was really nice and made me laugh putting me at ease for the rest of the day. He asked if I wanted to come over again to "study" together. Well I had chores to do at home so I invited him to come to my house, only we had to park on the next street and sneak in the back door so the neighbors wouldn't see. Anyway, as I was starting the wash he came up behind me, putting his hands over my breasts, and pressed himself into my bottom. He kissed my neck and nibbled on my ear sending shivers through my body. When he put his hand inside my blouse and pinched my nipple I started gushing in my panties. He knew what he had done because he heard me squeal as I bit my lip.

The next thing I knew he had lifted my skirt, pulled the damp crotch of my panties aside and pressed his engorged manhood into my steamy opening from behind. I tilted my butt in the air and felt him slide deep inside me. It didn't take long for my next orgasm to begin. This one didn't stop and I kept gasping for air and clutching at anything I could grab. Juices poured from me until I could feel them trickling down my leg. I was in a daze when Shane grunted and began squirting semen into my belly. He kept slamming into me with hard jerky thrusts, shooting jets of hot cum into my twitching pussy over and over again. I started to overflow and felt his stuff streaming down my leg. When he finished he stayed inside me as he slowly deflated, squeezing my tits and pinching my nipples. I had another orgasm and felt my pussy squeeze his cock in a series of small spasms. This caused another flood of juices to gush from me.

Needless to say my panties were a mess so I removed them and added them to the wash. I turned around and Shane unbuttoned my blouse, then unsnapped my bra freeing my tits for him to fondle and kiss. We continued to kiss and touch each other in the laundry room until he had me cumming again with his fingers.

We went into the kitchen for a drink. I told him he had to use a condom next time so I wouldn't get pregnant. He said he had a better idea, then took off his pants, hopped up on the counter and sprayed whipped cream all over his penis. He told me it was time for my after-school snack. I dove right in, cleaning him with my tongue and sucking him into my mouth. He started to grow and was soon fully erect. I took him into my throat and fondled his balls.

I thought he wanted to cum in my mouth and was working hard to make it happen when he pulled my head away and ordered me to stand with my legs spread and my hands on the counter. He pulled a stick of butter from the refrigerator and rotated it into my asshole. Then he rubbed it all over his cock. He spread my cheeks, and then I felt the tip of his cock press against my sphincter. He teased me until I begged him to shove it in my ass. He rammed it all the way in with three quick thrusts, then began rapidly slamming all the way in and out.

I fingered myself to several orgasms while he continued fucking my ass. About ten minutes later he grabbed my hips and roared out loud and filled my bowels with several squirts of cum. He finally pulled out. Diary, that's when I did something you're going to think is really disgusting, but I was too hyped with passion to care. I dropped to my knees and took him into my mouth squeezing the last few drops from his cock, then kissing and licking it as it slowly deflated.

We fucked one more time on the couch - this time with a condom - and then I asked him to leave so I could finish my chores. Well, instead of leave he offered to help me with the chores if I promised to go out with him on Saturday. I told him he'd have to meet my parents first. Anyway, as an extra reward I gave him a blowjob on the back porch as he was leaving. He was pretty well drained and it took me twenty minutes to make him cum. I swallowed it all, then kissed him goodbye. My jaw muscles were really sore when I woke up this morning.