Diary of a Teenager Ch. 01

September 8

Dear Diary,

It's been a long time since I talked to you, but a lot is on my mind. School has started and I am still a virgin - technically anyway. I must be one of the last virgins at our school. Judy, my best friend, did it this summer at computer camp with one of the other counselors. The way she described every little detail I knew it had to be true, leaving me the last remaining virgin I know.

My basic problem is that I'm too shy and too much of a bookworm. I don't get out much because my parents are so strict. Every time a guy starts to flirt with me I freeze up, giggle and turn red. I'm not ugly or anything - my mom says I'm pretty - and I think I have a decent body. Judy says that if she had my looks and body she'd get laid (she uses the "f" word) every night, and I'm sure she would.

Oh Diary, what am I going to do? Even though I'm still a virgin I must be oversexed. I think about sex all the time. Of course, Judy doesn't help. I still remember that day I stopped by her house and she held up two big plastic penises. Judy told me it was time to lose our virginity, and then turned on this really nasty videotape. I sat there absolutely mesmerized. I knew a little about sex, but nothing like what I saw. At first I was shocked. I told Judy it was gross and thought about leaving. Something stronger held me there and kept my eyes glued to the screen. I watched girls do things I didn't even know were possible, to one or more guys and to each other.

I had never seen a man's penis, much less a hard one. I started to get this terrible tingling between the legs and wanted to touch myself badly. I resisted as long as I could even though I noticed Judy had her hand in her jeans, which somehow turned me on even more. Suddenly my head started to spin and my body started trembling. I grabbed the couch and thrust my hips forward as ripples of pleasure surged through me. I was gushing juices like crazy and could feel my panties getting soaked.

When it was over I was really embarrassed. Judy said she had never seen anyone have an orgasm without any touching. Then she stripped off her jeans and told me she would demonstrate how to use our little "friend". Hers was blue plastic and about eight or nine inches long. She invited me to join her but I was still too embarrassed. I didn't leave either because I wanted to watch more of the movie. I kept sneaking glances at Judy who had propped her legs up on the couch and was rubbing the blue thing across her mound. I had never seen her naked and noticed how red and hairy she was down there compared to me. She lifted her butt off the couch and I could see the blue thing go inside her. She only had a little bit in her and was moving it all around while she rotated herself against it. It was really hot, and between watching Judy and the video I could feel another tingling building between my legs.

Judy was getting close to an explosion herself. That's when she grabbed the blue monster (we named it that) with both hands, pulling it out and shoving it in very hard. She let out a squeal and more of it disappeared inside her. She slid down on the couch and kept slamming it in and out until her face scrunched up and she screamed out as if in pain. Her body thrashed about as she kept slamming the blue monster deeper and deeper into her belly. She finally collapsed and slumped lifeless onto the couch.

I needed to touch myself desperately or I was going to die. I picked up my little friend (which was also nine inches but red) and slipped it inside the leg of my loose fitting shorts. When I pressed it against my panties, I hit my sensitive spot sending jolts through me up to my head. On the video there was a blond bouncing up and down on this guy's huge penis. The camera focused in on her butt. I could see him slide in and out of her as she lifted up and slammed down over and over.

I wanted to be her so badly. I leaned forward, lifted my butt off the couch, pulled my panties to the side and slipped "Big Red", as we named it later, into my opening. Holding it firmly underneath me, I pressed down against it. It slid into me until it hit some resistance. I lifted up and slammed down, squealing as I felt a little pinch. Then it slid deep inside me. I continued bouncing up and down on it while watching the girl on the video do the same. When the guy doing her pulled out and shot his stuff all over her butt, I exploded like never before. I was gasping for air as I kept gushing over and over, unable to stop slamming myself onto Big Red. I don't know how long it went on, but when I finished my shorts were a mess and I was exhausted.

Judy congratulated me on losing my cherry, but we agreed that we were still virgins until we had a real penis inside. Judy had several videos, so I took one home and spent hours with Big Red pleasuring myself over and over. It became an obsession, and I would often do it as many as six or seven times a day. Just last week I worked up the nerve to put Big Red up my other hole after watching so many of the girls on the tape do it that way. I had done it with my finger in the bathtub, and even done both holes at the same time, but Big Red was so much bigger. It was uncomfortable at first, but now I get off just as easy that way. I wish I had a brother for Big Red so I could do front and back at the same time like the girls in the video.

September 13

Dear Diary,

It's been a week since school started and so much has happened. There is this new guy, Shane, who is a real hunk. He is in two of my classes. On several occasions our eyes met. He even said "Hi" to me a few times. I get all wet between the legs when I'm around him, and every time I use Big Red, which is all the time, I pretend it's Shane in me. Sometimes I even bring Big Red to school so I can get off in the bathroom between classes. I know, Diary, I'm shameless. Well, that's not really true because if it was I'd just walk up to him and tell him what I wanted. I'm just oversexed but shy.

Judy also had an interesting week, at least according to her version of events. She discovered it was a lot easier to get screwed if she lowered her standards. She got a ride home with Chet, a big chunky kid, after a chess club meeting. They started talking about all the popular couples at school and speculating as to whether they were "doing it". Judy told him that you didn't have to be popular to get laid (she used the "f" word being the trash mouth that she is) and then blurted out that she lost her virginity that summer. I would have been so embarrassed, but not Judy.

He defended his manhood and quickly disclaimed his virginity. Judy dared him to prove it. They climbed in the back seat and she quickly unzipped him. She used her hand to make him hard then told him to put on a condom. She slipped off her jeans and panties, swung her leg over Chet, placed his penis at her opening and lowered herself onto him. She told me he only lasted thirty-second before he grunted and emptied himself into his condom. Since he didn't have another condom, Judy made him finger her to a less than satisfying orgasm.

Judy was really horny. When they stopped to get a soda she saw Freddy, a tall skinny kid with zits. She ditched Chet and asked Freddy to take her for a ride. She asked him to pull behind a deserted building and coaxed him into the back seat. They started kissing. Judy rubbed her hand over his hardness, then slipped her jeans down to her knees. She guided his hand into her panties, moving his fingers up and down her slit until he got the rhythm. While Freddy was pumping his fingers in and out of her hole she unzipped him and pulled out what she described as a "monster penis", although she used different words.

Judy pumped her hand up and down his large organ. She said that she could barely wrap her fingers around it. He continued to pump his fingers in and out of her womanhood. She asked him if he had a condom, but he didn't. Judy decided she didn't care. She pulled off her jeans, straddled his lap and guided his "monster" into her steamy opening. She said she had to bounce up and down on him several times before she could feel him slide deep inside her. The pressure was too much for her. She lost control. Her whole body started shaking as she squealed and screeched uncontrollably. She said she could feel herself gushing like never before as he continued to plow deeper and deeper into her belly.

What she did next really shocked me. She climbed off him and put his large penis in her mouth. She said it stretched her lips, but she was eventually able to get about half of him in her mouth. She tried to remember how the girls in the video did it. Apparently she was successful. He only lasted a minute before shooting his stuff into her mouth. Judy told me there was so much of it that it spilled from her lips. Then she swallowed the rest. It sounded gross, but she said it tasted okay, and that it was a real turn-on to feel his stuff squirting in her mouth. Anyway, Judy invited Freddy over to her place this afternoon. She has a whole box of condoms and plans to put a big dent in it.

Oh, Diary, I could never be like Judy. I'm too shy. I'd do it with Shane in a heartbeat, but I don't think he'll ever ask me out. I guess Big Red will have to keep me satisfied, and I have to admit he's doing a pretty good job. Every morning when I wake up I take Big Red out of my bedside stand, rub him over my nipples and put him in my mouth. I even learned how to open my throat and swallow most of Big Red, just like the girls in the videos. After that I rub him across my mound and over my slit until I become wet enough to put him in me. Once Big Red is all the way in me I go wild slamming him in and out while rubbing my little nub with the other hand. It doesn't take long before I am gushing juice all over Big Red, my hand and the sheets.

Well, Diary, that's just the beginning of the day. Sometimes I have enough time to do it again after breakfast and before I have to leave for school. Since I almost always wear dresses (my mother thinks jeans make me look like a tramp), it's easy to slip my panties to the side and shove Big Red in my hole until I gush. Of course, this also means I have to go to school with damp panties.

If I'm not doing anything after school, I usually rush home and pleasure myself with Big Red before my parents get home. It's during these afternoon sessions that I get really nasty. First I take it into my mouth, pretending it belongs to Shane. I work it down my throat. Then I slip a hand between my legs and start rubbing myself through my panties, again pretending it's Shane doing it to me. I begin to gush almost immediately and have to take Big Red from my mouth as I gasp for air.

I remove my soaked panties and strip in front of the mirror on the back of my door. I love looking at my body and watching while I touch myself. I slip Big Red between my legs and start kissing myself. Well, Diary, that's when I get really nasty and start talking dirty just like the girls in the video. I say things like "shove your cock up my hot pussy" and "fuck me like a whore". I yell at him to "fuck me harder" and "deeper". When I get ready to gush I yell out "Oh God, I'm cumming. fuck me. fuck me". The worst part is that I like talking dirty. It makes me even more excited.

The other thing I really like is watching Big Red slide in and out of my cunt (oh, Diary, I hope you don't mind my using words like this - it'll be our secret). After doing - fucking - myself standing, I pull a chair up to the mirror and lift my legs up in the air. I can see my pussy open wide and glistening among the soft brown curls surrounding it. I use my fingers to open it and watch my little nub stand up. I pull out Big Red and rub him along my gash and over my clit until I'm all gooey. Then I watch as Big Red spreads my fleshy lips apart and enters my steamy hole. I shove it in deep and leave it there, swirling it around inside me. I can feel it deep in my belly and try to imagine how far inside me it is by looking at my stomach. Then I start fucking myself, changing the angle that I use to shove it in me. This time when I gush I can actually see the juice pouring from my cunt (God I love saying that) and dripping from Big Red and my fingers.

Of course, the last time I use Big Red each day is when I am in bed and the lights are out. I get on my stomach and do myself from behind. Then I hold it under me and bounce up and down on it until I explode. Sometimes I grease it up with baby oil and fuck my ass while I finger my clit. Usually I fall asleep right afterwards, but sometimes I wake up in the middle of the night and do it again.

So, Diary, that is a typical sex filled day for me. The only problem is the lack of a man. Will I ever lose my virginity?

September 16

Dear Diary,

Two exciting things happened today. After Geometry class Shane came up and started talking to me. I did my usual blush and stutter, but he just kept talking about how smart I was and how difficult the class is for him. Finally, he asked if I could come over next Tuesday afternoon and help him study for the exam. I just nodded, too stunned to say anything. He said he'd meet me after school in the parking lot.

I was so excited that I was really looking forward to going home and having a long nasty session with Big Red. That's when the second thing happened. Judy cornered me after school and asked me to come over. She said she needed help with something really important. Well, when we got to her room she gave me a video camera. She said Freddy was coming over and she wanted me to tape them having sex. She said I could hide in the closet which had a perfect view of the bed. I was about to object when the doorbell rang.

I quickly hid in the closet before Freddy and Judy came into the room. They stopped in front of the bed. Judy threw her hands around his neck, pressing her body against him and tongue kissing him. I put the camera to my eye and began taping. I played with the controls and was able to zoom in on their lips and tongues dancing with each other. I moved down their bodies and focused on her tight jeans. Her ass and hips were gyrating as she pressed her mound against him. He moved his hands down and cupped her cheeks, pulling her even tighter against him.

I zoomed out and watched her slide down his body until she was on her knees with her face pressed to his crotch. She unfastened his pants, pulling them down along with his Jockeys. I gasped as his monster was released from its prison. It was semi-hard and already as big as any I'd seen in the videos. Judy looked over at me and smiled. Keeping her eyes to the camera, she swirled her tongue around the bulbous head of his manhood before sucking it into her mouth.

I zoomed in on her face and watched him grow to full length between her lips. She kept sucking him trying to get more and more of him in her mouth. She was holding him with both hands and bouncing her head up and down over his shaft. He put his hands on the back of her head and started grunting, saying things like "yeah, baby, suck my cock" and "oh shit, here it comes". I could see him swell even bigger just as he let out a loud roar. Judy pulled him from her mouth and got blasted as his stuff shot up her nose and into her eye. She opened her mouth and stuck out her tongue. White goo kept squirting from his penis into her mouth and all over her tongue. When he was finished she swallowed it, then wiped her face with her fingers and licked them clean.

I had a hard time holding the camera steady. When he started shooting his goo all over Judy my pussy began to gush. I wasn't even touching myself. After she finished licking her fingers I put my hand between my legs to rub myself. My panties were soaked. I shuddered with a mini orgasm.

Judy told Freddy to take off his pants and get on the bed. His penis was lying on his stomach. Judy said she was going to do a little dance for him. Well, she put on quite a strip tease show and I taped the whole thing. Even though she's real skinny with small tits, she made it very sexy. She was dancing as much for the camera as for Freddy. When she peeled off her panties she stood right in front of the closet and bent over with her legs spread. I got a real good close-up of her bright red hairy pussy hanging under the cheeks of her ass. Then she reached between her legs and spread her pussy with her fingers so I could tape her juicy red lips.

While she was dancing Freddy's cock began to grow. I taped it as it moved along his stomach and began to straighten. When Judy was finished stripping, she climbed up on the bed with Freddy, then swung her leg over his head and lowered her hairy pussy to his face. He licked his tongue across her gash and shoved it up her hole, clamping his mouth over her mound. She ground her pussy against him and started pinching her puffy little nipples. I zoomed in on his mouth and tongue making love to her juicy gash. Judy started humping faster, and then squealed loudly as her pussy started gushing. I could see her juices dripping onto his chin and running down his cheeks.

Freddy's cock had grown to full length and was angled up from his body. Judy leaned forward and slipped it between her lips while keeping her pussy pressed to his mouth. They munched on each other like this for several minutes. It was so hot that I just had to touch myself. I kept taping while I slipped a hand into my panties and started fingering my clit. It didn't take long before I was gushing again. This time I had to bite my lip to keep from squealing out loud.

Judy pulled the box of rubbers from the bedside stand and unrolled one over Freddy's sizable cock. She straddled him with her knees and wedged the head of his monster between the lips of her pussy. She moved his cock back and forth across her gash and over her clit. It was quite a view from the closet where I was taping. The entire length of his cock was visible as it poked up into the hairy patch just below her ass cheeks. Slowly she sank down on it and I watched it disappear inside her. She lifted up and slammed back down on his throbbing manhood over and over, impaling herself deeper and increasing the pace on each thrust.

Judy leaned forward against Freddy and reached back with her hands, digging her fingers into the cheeks of her ass. I zoomed in and watched her pink asshole bounce up and down as his shaft slid in and out of her pussy. Every time she lifted up I could see the lips of her cunt gripping his rubber-covered cock tightly. She was really hot. His shaft glistened with her juices that were already spreading onto her thighs and over her asshole (god, I can't believe I'm using these words so freely). She had to be close to an orgasm. When I heard her scream and saw her clawing at the bed I knew I was right.

Next she had him fuck her dog style while she faced towards me. Although I couldn't see his cock slide in and out of her, I was able to capture her expressions of pleasure. She seemed to be in a steady state of orgasm. Her whole body shook each time he slammed into her. She was gasping for air and squealing with pleasure. Her eyes looked desperate. Then I heard him grunt and zoomed out. Judy collapsed onto her stomach screaming at the top of her lungs as he continued thrusting into her. I could see his cock thrusting up and down between her ass cheeks. He was on his knees above her with his arms to her sides propping up his upper body. He grunted repeatedly as he emptied himself into the condom buried deep in her belly.

I was desperate. My pussy needed a good thrashing but all I had was my fingers. Fortunately, Freddy finally rolled off Judy and left for the bathroom with the cum filled rubber hanging from his half limp cock. I rushed out of the closet and told Judy I needed the blue monster. Instead, she pulled out a 12-inch flesh colored rubber penis with grooves on the side. I sat on the bed pulled my panties to the side and fucked myself crazy until a huge orgasm came crashing down on me. I nearly blacked out. Judy started shaking me and said Freddy was coming back. I pulled the crotch of my panties over the end of the rubber penis and staggered back into the closet just in time.