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I Fucked Him...I Fucked Up.

Author: badin10shuns
Category: Cheating_Stories
Last updated: Nov 26, 2005

Rated 3.9 with 14 ratings
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At 16 I was not exactly a picture of innocence. My name is Jessica and this is my story.

I was a sophmore in high school at the time of these events. I had a fiance who I was hardly ever allowed to see. I could only see him behind my stepfathers back. So, needless to say, I couldn't get laid very often. Plus the fact that "he wasn't that type of person" and didn't want to lose his virginity untill marriage. Well, I was in a great situation.

I'm around 5'6" and I weigh about 130lbs. I had somewhat large breasts, not sure of the exact size anymore, they were well within the C-cup range. I had a small waist and what most people would call a "ghetto booty," I never had any complaints about my body. I had long flowing curly copper colored hair, I always had it back. I have brown eyes and extremely white teeth, topping off my creamy smooth complection. I was always told that I was gorgeous.

My best friend, her name was Christine, was, not as fortunant as me in the looks department. She wasn't ugly, but she was plain. She stood 5'4" tall, and weighed just about 118lbs. Her breasts weren't large, they were within the B-cup range, and she had a tiny waist. She had a heart-shaped butt and a face that was more oval then anything else. She wore glasses and had brown eyes. She had somewhat long brown hair, it hung to about the middle of her back, and she natrually had a blonde streak right in the front down her hair. She was more of the churchie type as well.


She had a boyfriend, his name was Allen, and I didn't see it at the time, but he was the ugliest thing I had ever laid eyes upon. For some reason, I convinced myself that he was hott and extremely sweet. When I look back upon things, I thank god my friend, Rose, was there to set Christine and I both straight. Allen was around 5'5" and had really stringy, hardly ever washed, blonde hair, but he had dyed it, so it was half black. He wore glasses and never brushed his teeth. I don't know what I could have possibly saw back then, but, I was young and foolish.

He approached me one day and told me he had a thing for me. So that friday, while Rose and Christine waited at the pep-assembly for me, Allen and I snuck off down into the woods behind my school. He came over and kissed me and we began to make out passionatly. I ignored the horrible taste of his tongue in my mouth, and stopped myself from gagging. He proceded to pull my shirt off while I unbuttoned his. He peeled it off and revealed his very weak looking body. He then un-snapped my bra and pulled it off. I undid his pants as he reached for mine and began undoing them. He slid them off of me and pulled his own pants off. He then pulled his boxers off as fast as he could and he ripped my thong off of me.


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He then told me to get on my knees, so I did. He grabbed the back of my head and forced his thin short cock into my mouth. I seriously doubt his cock was any bigger then a sucker. He kept sliding it in and out of my mouth untill he decided he'd had enough.

He pushed me onto my back and told me to spread my legs. As I did, he grabbed my legs under my knees and pushed them up and forced his thin cock inside of me. He started moving in and out as hard as he could.

"God Jessica you're such a fuckin' slut. You fuckin' whore. You love this don't you, you nasty cunt." He groaned out. "Here." He said, as he grabbed my hands and put them on my knees, holding my legs up for him. "Now take this you fucking slut." He forced his cock into my ass.

Even with his little cock, it hurt like a son of a bitch. I hated anal sex, I had only tried it once with the person I lost my virginity to only a year ago.

"God damn you take it out" I cried.

He forced his cock all the way into my ass and started grabbing my tits. I had let go of my legs and was now trying to push him away from me.

"Stop! Stop it hurts! Damn you stop!" I screamed.

"No you fuckin' whore." He rolled me over onto my stomach and forced his cock back into my ass. "You're gonna make me cum you little slut. You want it in your ass don't you."

He started fucking my ass as hard and as fast as he could. He told me he was going to cum in my ass and that I was going to enjoy it. I felt his hand smack my ass and heard a loud slapping sound. It hurt extremely badly and it felt like my ass was going to bleed if he didn't stop soon.

"Allen stop!" I groaned out.

"Fuck you, god, I'm almost there. Fuck take it you slut" he said as he grabbed my hips and shoved forward, forcing his cock all the way up my ass.

I felt his cock throbbing and pulsating in my ass. Then the first shot came deep in my ass. He started moving his hips in and out harder and faster, his cock exploding deep in my ass with every thrust. He then pulled it out and finished cumming all over my back. He was satisfied. He stood up and got dressed. Leaving me on the ground in the woods. I pulled myself up and proceeded to get dressed. It was hard to walk out of the woods in my condition, but I did it. When I reached the top of the hill, right before the school, he grabbed me, kissed me and told me "We'll do this again sometime" as he walked away.

I figured I'd had enough, but, as it turns out, he was right. Him and I fucked two more times before I had the courage to tell Rose. She saved me and Christine's friendship, and we finally realized what a low life creep Allen really was.

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