My Harem of Cheerleaders 6: Annie - Sex Party

"Fuck, that was good."


"Of course. I came fast. I haven't had sex that good a long time."

"Well, I stay in practice."

"You mean with Emma and Amanda?"

My face went pale. I had made that practice comment without thinking, and had no idea that Annie knew about both girls. As far as I knew, she still thought I was dating Emma.

"How did you find out?"

"They haven't exactly been quiet about the fact that you're banging both of them. They talk about you in the locker room, and they fight about you all the time. The whole cheer squad knows, and half of the football team thinks you're a god."


"Yeah. I mean, you were cool when they thought you were just dating Emma. Now, you're the guy who you conquered two cheerleaders. Three now, I guess."

"You not a conquest," I said, gently kissing her. "I didn't mean for any of this to happen."

"Neither did I. I texted you because I needed some to talk to and I didn't want the girls to make fun of me for still being in love with Ben, but now we're naked and I'm on top of you."

"Do you regret it?"

"Not at all."

I picked up my phone when it started buzzing.

"Is Amanda checking in on us again?"

"She wants to know if you're ok."

"Tell her I'm very ok," she said, smiling at me. "Wait a second, did you get off?"

"No, you kindof fell on me before I could, but it's fine."

"No it's not!"

"It really is. We'll just say you owe me one, ok?"

"You really are amazing, aren't you?" She said, as she hugged me.

We didn't bother putting our clothes back on. We didn't even bother cleaning up. Annie and I simply turned on the next movie we found, knowing the night was far from over.

"I don't suppose you'd want to go again?" she asked me, and moments later I was once again deeply penetrating her with my well-lubricated dick.

It became a pattern throughout the night. We would watch something for a few minutes, and then either go to the bedroom or just fuck on the couch the moment I was hard again. It only ended when both of us collapsed in my bed and fell fast asleep, completely exhausted.

When I woke up the next morning, I was greeted by the most sexy and beautiful sight I had ever seen.

Annie was lying on her back, her head tilted toward me with the dim sunlight streaming in on her. It perfectly framed her gorgeous face and shined off of her hair. The blankets were lying in a crumpled heap on the floor, and so her perky little body was left uncovered. She was wearing nothing but a smile and was emitting tiny moans of pleasure, perhaps from a wet dream. I was happy to see that her pussy was still soaking wet, and the fact that Annie was still overflowing with my seed gave me a twisted sense of satisfaction.

I pulled on my boxers, but didn't feel the need to put on any more clothes than that. However, I regretted that decision later, when bacon grease was splattering on my bare skin.

"What's that I smell?" Annie asked, emerging from the bedroom wearing my button down shirt with nothing underneath it.

"Chocolate chip pancakes, bacon, eggs and sausage."

"That sounds amazing. Where did you learn to cook?"

"My grandmother taught me. She was a down-home southern woman who cooked everything in lard. Every time I spent the night at her house, I came back ten pounds heavier."

Annie laughed. "She sounds fun."

"She was, but she always taught me to cook in bulk, so I hope you're hungry."

"I'm starving. You wore me out last night."

"No, you're the one who wore me out. Remember how you shoved me down onto the bed and started riding me?"

"Which time?"

"I think that was our second time in the bedroom."

"Oh, yeah. My favorite was when you had me bent over the couch."

"You said you didn't want to wait until we got to the bedroom, so I just started right then and there."

We both laughed and started eating, tearing into our food like starving wolves.

"Damn, this is the best breakfast I've ever had."

"It's simple to make. The secret is fat and butter."

"I'm going to be obese by the time I leave."

"If you ask me, you could stand to gain a few pounds. A lot of the girls on this campus are too skinny."

She laughed at me.


"That just sounds like something else you probably picked up from your grandmother."

After we had finished, and the subsequent food coma had begun to set in, we sat on the couch and turned on yet another film, while holding each other close.



"Can I ask you a question?"

"Sure. Ask me anything."

"How much do you care about Emma and Amanda?"

"Why are you asking me that?"

"I just want to know if you..." She trailed off, but soon started again without looking me in the eyes. "If you really care about the girls you sleep with."

"Annie, I care about you a lot. Please, don't doubt that."

"It's hard to believe that when you're seeing two other girls."

"Yeah, but I..." I started, but the words wouldn't come out.

"You what?"

"I didn't want to be seeing both of them."

"Oh, please. It's every straight guy's fantasy."

"But I would have given it up, for Emma."

"So, you really do care about her?"

I sighed. "Yeah, I do, but she doesn't want us to date exclusively. She said maybe we could after college is over, but not right now."

Annie put her arms around my neck and hugged me, and even though there was no sexual component to this moment of physical contact, it was the closest I had every felt to her.

"I'm sorry that happened to you."

"It's no big deal. For now, I think I'm better off avoiding relationships. As long as I'm not tied down, I'm free to fuck as many girls as I can handle, including you, beautiful."

I planted my lips on hers, and she ran her fingers through my hair.

"Alex, I don't suppose you're feeling well enough to-"

She didn't need to finish. I was already carrying her into the bedroom.

The two of us rolled around on the bed, kissing and caressing one another. She admired the strength of my body, and I was turned on by the softness of hers.

"Hey, so don't be weirded out by this," Annie said, "but there's this thing I wanted to try."

"What is it?"

"Well, Ben and I haven't had sex in a while, so a few weeks ago I decided to spice things up by... trying something new."

"What new things are you talking about?"

"I started using these new toys to... stretch."

"Stretch your muscles?"

"Not the ones you're probably thinking of. These muscles are in my..."

She trailed off, but I finally started to see where she was going.

"Annie, did you start using a butt plug?"

"I wanted to do something new to get Ben excited, but he broke up with me before we could do it. I even did this special cleanse before yesterday so that I wouldn't..."

"Shit on him?"

"I didn't want to phrase it like that, but yes. I really prefer not to let all that work go to waste, so I was thinking you'd like to try?"

"Are you asking me to fuck you in the ass?"

"I guess so."

My heart started racing instantly, and I pulled her in close for a long, sloppy kiss.

"I'll take that as a yes."

She laid down on her stomach, and I lifted up the long shirt so that I had a perfect view of her little, round bubble butt. I threw away my boxers, and slowly moved my hand up and down my thick pole with a fistful of lube. However, just before I moved to plunge inside, I ran two fingers along the lips of her pussy, coating them in the cum I had left in her. Her body trembled as I wetted my fingers in her cunt, and gently pushed them into her asshole.

"Be gentle with me. You were almost too big for my pussy. I can't imagine how big you'll feel in my butt."

I aligned my engorged manhood with her tiniest hole, and pressed the tip against her entrance. At first, I was too scared to push very hard, afraid I might hurt her, until I heard her begin to moan.

"Oh, get it inside. Get it inside."

I pushed harder, and when my head finally made it through, I saw her bite into my pillow.

"Are you ok, Annie?"

"Better than ok. Go slow, but don't stop pushing."

My cock started making progress, and slowly I penetrated her. Annie's sphincter was the smallest hole I had ever fucked, and I still remember the feeling of its warm tightness gripping my cock.


I slowly pulled out and pushed in again, picking up speed ever so slightly.


I began fucking her harder, and I felt her whole body quiver with every thrust as I buried myself deep inside her butthole.

"Oh, fuck," I said.

"What is it?"

"I think I'm about to cum."

The way the tight muscles of her asshole massaged my cock was too much for me to bear, and soon I was cumming deep inside of her bowels, unloading my cum inside of her.

"Oh, shit. Sorry, I didn't mean to cum so fast."

"It's ok. You were up one anyway, remember?"

"You really don't need to keep track of that."

"Really? Oh, well that's good, because I figured that the only way for me to repay you would be to let you pour out your semen in my ass and my pussy." She waved her petite little butt in the air while her face remained buried in the pillow. "I guess I was wrong."

I'm not sure if it was because I came so quickly the first time, but my cock was already hard and begging to taste her cunt.

I forced my way inside of her pussy in one thrust, making her bite the pillow yet again as I brutally fucked her.

"How do you feel?"

"Like you're going to tear me in half! It's so big and so long and so deep. I love being full of your cock, no matter what hole you're fucking!"

Both her words and the sight of my cum dripping out of her anus drove me to fuck her even harder, and now that I had cum once already, I wasn't going to do it again anytime soon.

"Shit, Alex. What are you, a machine?"

"Something like that."

All my time spent bending over Emma and Amanda had paid off. My hips and legs didn't even grow tired and my pace never slowed. Before I even felt myself grow close to the finish, Annie came three times, her pussy muscles massaging my cock every time.

"How much longer are you going to last?"

"I'm getting there."

"Get there soon, or I'm going to be bow-legged for the rest of my life."

"Don't worry, I'm close to cumming."

"Pour it out in my pussy. I need your warm semen inside both of my holes."

"Oh, fuck."

I finally came, filling Annie with the biggest load of cum I had ever produced. She came as well, making that her fourth time that morning. The satisfaction of feeling my cum refilling her womb must have driven her over the edge.

"If I can't sit through class tomorrow, I'm blaming you, Alex."


"Because you gave me the hardest fuck of my life, and wrecked my butt forever."

We both laughed, knowing that forever wasn't quite the right word. I'd be fucking her ass again quite soon.

"You know that Ben is an idiot, right? Any guy who doesn't want to date you must have an IQ of less than ten."

"I could say the same thing about Emma. She's dumb for not locking you down, but her loss is my gain."

"Thanks for saying that."

"I really mean it. I have it way better than her."

"What do you mean?"

Her face turned red before she answered, like she was just a bit embarrassed about what she had to say. However, she'd grown comfortable around me, and even though we'd only been close for a short while, we knew that we would stay that way for a long time.

"I have it better than her, because when she calls you for sex she only gets her pussy fucked, but when I call, I'll know that I'll be leaving with two cum filled, well-fucked holes, instead of just one."

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