Young and Drunk

Katy was the girl I dated my senior year of high school. She was rather short at 5'4" and she had shoulder length strawberry blonde hair. She wasn't the most attractive girl at school, but I was 18 and the combination of teenage angst and raging hormones made me more than willing to overlook any physical shortcomings. Anyways, it's not as if she was bad looking, she was certainly cute and she kept her body in fairly good shape.

Looking back on it now I think we both just wanted someone to explore our sexuality with. Being a teenage male, my mind was constantly filled with all sorts of filthy sexual exploits I wanted to try and Katy seemed willing to indulge in many of the same things.

We experimented with each other after school, during the weekends, and just about any other time we could be alone. We started out as most people do, I suspect, touching each other and making out until we eventually developed a routine of me fingering her and afterwards, her giving me head. After getting used to this routine, we finally decided to move onto sex and it was incredible. There is nothing quite as exhilarating as the first time. We both loved having sex so much we could hardly keep our hands off each other and we must have tried every sexual position known to man, but despite the wonderful feelings it elicited, our sex also became a routine of sorts. I still had a longing to try something else, something that had fascinated me ever since I discovered sex, but I was much too shy to ever propose that Katy bend over and let me stick my penis in her ass. I figured that anal would just be my secret desire forever, but I never would have guessed in a million years that she would be the one to offer it.

It was late Sunday night and Katy had snuck out of her house to come over. We used to hang out in the pool house in order to avoid being bothered by my parents. It was a nice house as far as pool houses go, complete with a refrigerator and an upstairs loft with a bed. Katy and I were just hanging out, watching TV, and drinking some tequila I had acquired from my parent's liquor cabinet. After a while the tequila started taking effect and we both got a little bored with watching TV so we turned our attention to each other.

We began as usual, just touching and kissing. I began running my hand up her thigh, inside the little gray, cotton shorts she was wearing. She quickly stopped me and said,

"Let's go upstairs."

With her cute little seductive smile which I had come to recognize as meaning that I was about to get lucky.

I eagerly agreed, following her up the stairs and over to the bed where she laid on her back, spreading her legs open as I got on top of her and we continued making out and fondling each other. My hand moved up her t shirt, feeling her small, firm breasts lying beneath her B cup-size bra. She lifted her hands up above her as I pulled the t shirt off her body throwing it to the floor. Apparently very eager to get naked, she reached back and unclasped her bra, tossing it aside, and revealing her perfect little, milky-white breasts and quarter-sized pink areolas.

"Get naked" she said, as she laid back and pulled her own shorts and panties off in one swift move.

I quickly obliged, removing my shirt and pulling my jeans and boxers down, leaving my rapidly-stiffening dick hanging there for her to see. Staring at her little body, I could see that she was more eager than usual to get down to business. Through the little strip of pubic hair she had, I could see the glistening of her slit in the moonlight that shone through the windows and before I knew what was happening, she had my dick in her hand, rubbing it until it rose to it was fully erect, and finally rolling a condom over it. I lay down on top of her as she spread her legs and took my throbbing penis in her hand, guiding it to her wet entrance. Slowly thrusting forward, I entered her wet and willing pussy, immediately thrusting my hips forward to get deep inside her. She wrapped her legs around me, pulling me in closer as I fucked her as hard as I could. It might have been the tequila, but neither of us was in the mood for slow romantic sex...we wanted to fuck! After only a couple of minutes of me on top of her, she asked

"don't you want me to ride you for a while baby?"

"Sure" I replied, getting off of her and rolling onto my back.

She eagerly got up on her knees and straddled me. Taking my hard dick and positioning it at her wet pussy, she slid herself down on top of it. She began riding me like never before, bouncing up and down on my dick, her little boobs bouncing right along with her. As she leaned back and let my dick slide all the way up her pussy, grinding her crotch into mine, I reached out and grabbed her ass cheeks, spreading them open wide. She resumed raising and lowering herself on my dick and my fingers ran up and down her ass, touching the little folds of skin around her anus. She moaned as I touched her ass saying

"Ooohhh baby, I love your hands all over my ass like that."

Soon thereafter she slowed her riding, looked right at me, and giggled a little as she asked,

"Are you feeling kind of kinky tonight baby?"

"Sure, why not" I said.

"Do you want to stick it in my ass?"

My mind began racing with excitement, but I tried to keep cool.

"If that's what you want, I'll try it" I replied.

"Okay" she said, sliding up off my dick.

I got up on my knees as she lay flat on her belly. Getting behind her, I pulled her hips so that she was up on her knees so her ass was sticking up in the air. As she relaxed into the position, her little butt cheeks opened up revealing the tiny pin-sized hole that was her anus. I couldn't believe I was about to live out my biggest fantasy and in my excitement I forgot all about trying to find any kind of lubrication to help the process. Taking some deep breaths to keep calm and stroking my cock to keep it hard, I positioned myself behind her. I placed the head of my dick against her tight hole and slowly pushed forward. As I looked down, I could see my dick bending against her tight ass. It made me even harder knowing that her ass was so tight. My dick quickly hardened like a rock and I pushed forward again, this time watching as her tight hole gave way to my stiff cock, spreading open around my dick.

"OOOOOHHHHH" she moaned, and I pushed on watching the head of my penis disappear into her ass. I lay myself on top of her and thrust my hips forward entering her ass deeply. I could hear and feel the little pop of the condom as it broke, but I didn't dare pull out of such a wonderful place.

"OOOOOOHHHHH" she moaned again. I could hardly contain my excitement and I began thrusting at her ass harder.

"Aaaaaahhhh, oooohhhhh" she moaned.

I pulled back her hair so I could watch her face as I nailed her in the ass. Feeling the muscles of her anus tighten around my throbbing dick and watching her face grimace in pain made me so excited. I pumped harder, my balls slapping against her butt cheeks and I glanced down to watch my dick going in and out of her tight little ass. When I looked up again and saw a tear running down her cheek, the excitement became too much and I felt the eminent orgasm. I made a final thrust deep into her ass as cum exploded from my dick, filling her rectum with warm jism.

We both lay there for a moment breathing heavily, until I finally got the energy to get up and slowly pull my penis from her ass. Her ass made a little popping noise as I pulled the head of my dick out and I watched her tiny hole gape wide open for a few seconds and then close itself off. Pulling the remains of the condom from my softening penis I kissed her lovingly and we started to get dressed. As I watched her pull her panties on, I could see a bit of white cum drip out from her ass and I couldn't help but smile.