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When Cheerleaders Misbehave…

Category: Anal Sex
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Kelly and I met in our freshman composition class, two eighteen-year-olds sitting in the back of the room trying not to fall asleep together and cutting jokes about our professor as he talked about how his class was an important foundation for our collegiate success, would help us in life, etc., etc. All the same shit that high school teachers tried to tell me.

She was a cheerleader with a body that I did my best not to scan from top to bottom every time we’d hang out in my dorm room drinking together (i.e. most nights). She had this chin-length blond hair and sparkling blue eyes, and these long, toned legs, no doubt the products of endless workouts. I could never decide which I wanted more: that hair bobbing up and down over my cock or those legs wrapped around my hips. Actually, that’s not true; I knew what I wanted the most: that tight little ass of hers that she always had wrapped up tight in mini-skirts and waving in my face as she danced drunk in my room.

But I had a girlfriend back home, so I couldn’t do anything with Kelly. After all, Sara and I had been dating for a couple of years, and I really loved her. No matter how much my cock begged me to bury it in her, no matter how much Kelly flirted with me, I knew I didn’t want to ruin what Sara and I had for a drunken fuck. Besides, Kelly flirted with most guys. In our first month of college, she had dated three different guys on my floor. I never asked how many she’d slept with. Let’s just say the girl got what she wanted. So we’d just hang out drinking and watching movies together. I’d go watch her at the football games; then we’d go out to eat before cleaning up and hitting the Saturday night parties.

It was all great for the first couple months of the semester, but then came the night where I passed out in my bed watching Braveheart with Kelly. Normally, if I passed out, Kelly would just head on back to her room, or find some guy on the floor to fuck, but, at least according to her, she wanted to finish watching the movie, so she just lay there watching the film, with my sleeping head in her lap. Truth be told, I’ll probably never know exactly what happened that night, just what I’ve pieced together from Kelly and Sara. Apparently, Sara called while I was passed out, and Kelly answered the phone, something she should have known better than to do, since she had long ago come to recognize the ring for Sara on my cell phone. When Sara asked where I was, Kelly told her that I was asleep in bed. When Sara asked what Kelly was doing, she said she was lying in bed watching a movie. Now, looking back, I guess Sara over-reacted, but I’m sure all she was doing was picturing Kelly and I in bed together. So, when I finally woke the next day, alone by that point, I didn’t have a girlfriend. Needless to say, I was pissed. In fact, I wouldn’t even speak to Sara for two weeks, but, with a home game approaching, Kelly offered a truce of taking me out to dinner after the game.

During the game, I couldn’t help but to watch Kelly’s body move as she went through the cheers: her skirt flying up on kicks to reveal her toned thighs and bloomers, the smile on her face, both innocent and dirty, and the way her uniform pulled tight around her breasts, her nipples poking slightly through the red and white cloth (Kelly once confessed to me that it turned her on to cheer without a bra on, saying that she’d like to try to go without any underwear in her last game). Feeling an erection stir in my pants, I began to realize why Sara had been so jealous and concerned.

After the game, Kelly met me out by my Malibu, a graduation gift from my parents, and we began driving outside of the Iowa town where we went to school. We talked lightly about class and mutual friends of ours, not delving into any series topics until the sun had set and Kelly realized we weren’t at a restaurant yet.

“Exactly where are we going?” Kelly asked, an unusual tinge of nervousness shadowing her voice.

“You’ll see,” I responded, then, after a long silence, “Don’t worry; we’re almost there.” Soon, we arrived at a dead end surrounded on all sides by cornfields. I parked my car, facing the corn, left the lights on and stepped outside. Reaching back behind my seat, I pulled out a small bucket and looked at Kelly, who watched me nervously. “You coming?” I asked. Kelly stared at me for a second and then undid her seatbelt without saying a word. By the time she came around to the front of the car, I was sitting on top of the bucket by the edge of the corn, with the lights shining in my face. She leaned back against the car, feigning calmness. “So here’s the deal,” I said as cooly as possible, while Kelly’s frame shielded half my face from the light, “I lost someone I really care about, so now I’m going to take something from you.”

“If you wanted to fuck, you didn’t have to drive me out to a cornfield,” Kelly replied.

“You’d be wise not to talk back,” I answered. “Now, turn around, place your hands on the hood of the car, spread your legs, and stick that tight ass of yours up in the air.” Kelly stood frozen, her eyes on the ground, unable to bear my steady stare. “Do it.” I drug out the words, ending them in a quick snap. Kelly slowly turned around and assumed the position, putting her face flat against the car and sticking her ass out. With the light splashing against the top of her white skirt, her ass looked so round and sweet. I had to adjust my pants as my cock began growing hard. “Good girl. Why don’t you reach back there and pull your underwear off?” Kelly took her hands from the car without lifting her face, and slid her bloomers down until they were loose enough on her legs that she could shake them down by wiggling her ass at me. “Your thong?” I questioned.

“I’m not wearing one,” she whispered.

“What was that?” I asked.

“I’m not wearing one,” she replied more loudly. “It turns me on to cheer without any panties. I can feel myself getting wet easier that way.”

“You are a dirty little slut, aren’t you?” Silence. “Aren’t you?”

“You have no idea.” I could tell that Kelly’s kinky side was beginning to kick in and that she wanted to play with me, so I decided to take control of the situation.

“Stand up.” I ordered. She did. “Take your top off.” Kelly began unzipping the back of her cheerleader’s top, eventually letting it fall onto the hood in front of her. “Turn around.” Kelly slowly turned toward me, tossing her hair back behind her head when she finally faced me. “Come here.” As Kelly strolled nearer, I could see that her nipples had grown hard. In fact, I think that she was more turned on than I was. When she stood in front of me, looking down with a sultry smile, I ordered her to her knees. Kneeling there, she smiled at me like she couldn’t wait to get her mouth around my cock, as if she’d been thinking about what she would like to do to it for the last two months. “Spread your legs,” I told her. She parted her knees slightly. “All the way until your pussy’s rubbing against the ground.”

“But it’s concrete,” she protested. I softly ran my hand through the hair on the top of her head, brushing those sweet blond strands from her face as she licked her lips at me. Then, I quickly grabbed a handful, using it to jerk her head back and push her down. “You’ll do as I tell you; do you understand.” Kelly nodded. “What?”

“Yes,” she answered.

“Good.” I grinned at her. “Can you feel the concrete against your pussy?”

Kelly dropped her eyes. “Yes.”

“Why don’t you fuck it for me?” Kelly began lifting her hips up and down, grinding against the ground beneath her, as I stood from where I’d been sitting.

“That’s a good girl.” I undid my belt, pulled it from my pants, and tossed it over by the car for later use. “Now, when you were licking your lips earlier, was that because you wanted to suck my cock?”

Kelly started to nod, then spoke. “Yes.”

“Go for it.” Kelly started to reach for my pants, but I quickly stopped her. “Put your hands to your sides. I want a blowjob, not a handjob.” Kelly placed her hands flat against her hips, as if she were standing at attention before a cheer. She then leaned forward, took the zipper to my jeans in her teeth, and pulled it down, her eyes glancing up to me for approval. The button, however, proved much more difficult, but the sensation of her chin rubbing against my cock was worth the wait, as she repeatedly tried to maneuver the button through the whole, eventually succeeding, for which she was rewarded by having my cock pop out of my pants right in my face.

“I was thinking of you when I decided not to wear boxers today. You’re right. It is kind of a turn-on.” Kelly began licking the tip of my cock, delightedly lapping up the precum that had pooled as I watched. “Honey, don’t play games,” I commanded. “I told you I wanted a blowjob.” Now, my cock’s an average six inches long, but it’s really thick, so she opened her mouth wide and took about half of it in as she leaned forward. That, of course, wasn’t good enough. So I placed my hand behind her head and shoved the rest of my cock into her mouth. “I really would have expected you to be better at this.” Hearing this, Kelly looked up at me angrily, so I took another fistful of her hair and began face fucking her. I smiled as I watched her trying not to gag, heard her desperately sucking air in through her nose as I slammed my cock in and out of her mouth. Most of the freshman guys she’d been with were probably glad just to have a girl sucking them off, but I was giving that mouth of hers the most intense working over it had ever received. Her lipstick was staining my cock red as she dropped her jaw, resigned to the cock pounding into the back of her throat.

When I felt myself sufficiently hard, excited, and lubed, I pulled my cock from her lips, and watched her weary head and mouth drop. “Return to your original position at the car,” I ordered, and Kelly obeyed, walking ahead of me until flailing herself across the car. As I walked up to her, I gave her ass I quick smack, saying, “That’s a good girl,” while I picked my belt from the ground, then wrapped it around and fastened it against her wrists. I stood behind her, one hand on her hips, the other lifting her skirt and admiring the gorgeous ass before me, toned and tightened from years of running, jumping, and kicking. My cock pointed straight at it in anticipation.

“You know, you’re a little late to be taking my virginity,” Kelly quipped.

“I wouldn’t say that if I were you, I responded.”

Rumor had it that Kelly once kicked a guy out of her room, mid-blowjob for asking if he could fuck her in the ass and that she kneed a naked guy in the groin for trying to stick a finger in her anus while they fucked. Apparently, it was the one part of her body that she wouldn’t allow anyone axis to. I intended to change that, something she quickly came to realize as the head of my cock began rubbing against her asshole.

“What the fuck?!” Kelly screamed, attempting to jerk herself away from me. I quickly reached across her body and pinned her wrists with one hand while I pushed her hips down with the other.

“We can do this the easy way or the hard way,” I growled. “No matter what, I’m taking that ass tonight, so just remember, the more you fight it, the tighter that hole’s going to be when I plunge in…and don’t expect me to take it easy.” Kelly looked back at me pleadingly, and I winked at her. She could pretend to fight all she wanted, but I was behind her staring at one wet pussy and a pointed little ass that was begging to be fucked. And she knew it, as she put her face back down against the car and stood still.

I grabbed both sides of her hips and shoved my entire cock into her in one deep stroke. Kelly emitted the sharpest yelp I had ever heard as my cock dug into her ass, but she didn’t fight it for one second, so I chose to play nice and slowly fuck that ass of hers. Besides, I figured, I might as well enjoy the amazing sensation. It was the warmest, tightest feeling I had ever experienced, one that I hadn’t dared to ever ask Sara for. I could feel Kelly’s muscles tight around me, massaging my cock with each entrance and exit from her.

Eventually, Kelly began to relax and even moan some, so I reached forward with one hand and began tweaking her nipples tightly between my fingers, feeling her mid-sized breasts overflowing my hands and hearing her gasp with pleasure each time one of her nipples popped between my thumb and forefinger. For her part, Kelly began rubbing her clit against the hood of my car, since her bound hands were unable to help. After a little of this, I decided to push things up a notch, and grabbed her ass in both hands again, pounding my cock in and out of her, as I periodically spanked her ass, watching the skin turn from white to red as I slammed in and out of her, listening to her gasp and moan while my balls slapped against her pussy. I could feel myself growing closer to the edge with each pounding stroke, but what was really pushing me over the top was hearing Kelly panting loudly on the verge of her own orgasm.

Noticing this, I took a moment of extreme self-control and stopped my throbbing cock just outside Kelly’s ass on the next stroke. Looking down, I noticed that Kelly was pushing her ass back toward my cock, begging for it to slam back inside her as I pulled it away.

“What’s wrong?” I asked

“I want you to fuck me.”

“But I thought you said other guys have taken care of that?”

“I want you to fuck me in the ass,” she begged. “I’m a bad, dirty, slut who deserves to have her ass punished.” Then, in a moment I’ll never forget, Kelly looked back at me with desperate blue eyes and continued. “Please punish me. Please clean my ass with your cum. Please.”

At that point, I couldn’t have said no if I wanted to, so I took her hair in one hand, her clit in the other, and slammed my entire cock as far into her as I could force it. Immediately, both of us flew to new heights of orgasm, myself bucking wave after wave of cum into her ass, while her muscles clinched down on my cock and her body trembled with pleasure.

Afterwards, I untied her hands and we both collapsed onto the concrete, her lying against me, our juices staining my jeans. I may not have done anything that night to make Sara come back, but I had found myself a hot fuck buddy for the next four years.

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