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  1. The Cheerleader Harem: Part 1
  2. The Cheerleader Harem: Part 2
  3. The Cheerleader Harem: Part 3
  4. The Cheerleader Harem: Part 4
  5. The Cheerleader Harem: Part 5
  6. The Cheerleader Harem: Part 6
  7. The Cheerleader Harem: Part 7
  8. The Cheerleader Harem: Part 8
  9. The Cheerleader Harem: Part 9
  10. The Cheerleader Harem: Part 10
  11. The Cheerleader Harem: Part 11
  12. The Cheerleader Harem: Part 12
  13. The Cheerleader Harem: Part 13
  14. The Cheerleader Harem: Part 14 [Final]

The Cheerleader Harem: Part 14 [Final]

Categories Diary, Anal, Bi-sexual, Consensual Sex

Authror: Rich Richardson

Published: 06 December 2017

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“Come on. The bus will be here soon.”

“Cool, just… Can I ask you something?”


“Did we…” I tried to ask, but kept stuttering and trailing off. “Did we have sex?”

“You don’t remember?”

“Everything is just kindof foggy.”

She smiled yet another wicked smile, and simply told me, “Maybe.”

“Still dangling the carrot?”

“You bet your ass I am.”

I looked at her with contempt, and told her, “You really are a sick bitch.”

Things were a little bit awkward between Lucy and I, after that. After a one night stand fueled by sadness and drugs, the two of us needed a bit of space. Unfortunately, it was a long bus ride back home, which meant we had to spend forty-five minutes crammed together in a tin can on wheels.

“You’re starting to look a lot less punk,” I told her.

She awkwardly smiled and ran her hands through her hair. She’d washed out most the dye, and her hair had returned to its normal color.

“We have to go back to reality sometime.”

“Yeah, I suppose we do.” Though I agreed with her, I wasn’t eager to return and face down Emma, and thoughts of Kendra had been slowly but surely creeping back into my painfully sober mind.

“So, who hurt you?” I asked, making her turn to look at me in confusion.

“What are you talking about?”

“You seemed to know what you were talking about. I assume you’ve been through a similar heartbreak.”

“Not really. I just come here to get crazy, sometimes. It helps me cope.”

“Cope with what?”

She stayed silent for a good minute, not wanting to answer.

“I’ve already seen you naked,” I told her. “At least, I think I have. We can’t get much more open than that.”

She laughed. “Fine. I like to hang out off campus because, if I’m being honest, I just hate that place.”

“Yeah, I never bought into all the drinking and greek culture.”

Lucy shook her head. “It’s not that. I hate everything about that place. Fuck, I didn’t even want to go to college. I wanted to take my college fund, buy an RV and just drive up the coast, but my parents wouldn’t let me. They said this would be better in the long run.”

“Well,” I awkwardly stammered. “They’re not wrong.”

She sighed. “I know, but it’s my life, and I’ve spent every moment being told what to do. Lucy, wear this. Lucy, do that. Lucy, practice your violin; it’ll help get you into a good school. Lucy study your Spanish; bilingual kids get scholarships. Lucy, join the cheerleading team; you need more extracurriculars. I just hate it.”

“I’m sorry.”

“No, you’re not. I know you don’t care. You’re the sexy loner who does whatever he wants. You probably don’t have any family to deal with.”

“Both my parents visited last week,” I said, quick to correct her. “I love my family.”

We sat in silence after that, and Lucy just seemed to sink deeper and deeper into depression as it dragged on.

“You know, I wasn’t always a loner.”

She looked up at me, and I jumped at the chance to end the silence.

“Back in high school, I was actually on the football team.”

She chuckled.

“No, really. I ended up quitting because I got involved with a couple of really bad guys, though. I didn’t like who they turned me into.”

“What, did they make you go streaking, or something?” she asked with a smile.

“No… Well, yes, but that’s not why I quit. When I was a freshman, I got bumped up to Varsity because they were really short on players, and I really wanted to impress the guys on the team, especially the linemen. That was where I wanted to play, because that was where my dad used to play, but I was too small.”

“What did they make you do?”

I sighed. “There was this girl named Amy who used to hang around with Emma, because she really didn’t have any friends. I guess she kindof developed a crush on me, and this senior linebacker named Doug told me I should invite her out with us.” I wrung my hands in frustration, as the words became harder and harder to say. I hadn’t told this story in a very long time. “We left her in a field, in the middle of the night. I can distinctly remember myself laughing when we saw her chasing after the car, trying to flag us down. I guess she just thought we had done it on accident, at first.”

“Did you get in trouble for it?”

“No. Some of the other guys on the team found out and almost beat the shit out of Doug, but nothing else really came of it.” I suddenly remembered the last time I had told that story. It was shortly after the event itself, when I had told Emma.

“What happened to Amy?”

“She walked home, I guess. Or, maybe she hitchhiked. I don’t remember. The only thing that really stands out is this moment afterwards, when I had finally impressed Doug and the other linemen, and we were walking down the hallway, laughing.” I paused yet again, to look down at the ground. “But then I remember seeing Amy, and she didn’t even react to me. I had assumed she would be mad, maybe throw something or yell at me, but she was just quiet, shockingly quiet.” Lucy held my hand so I could stutter the last few words. “I realized who I was, after that. I wasn’t some mean-spirited jock or an evil force, I was just a confirmation to her. She must have thought a thousand times that she didn’t have a single friend in the world, and I confirmed that she was right. She must have felt so alone for so long, and I told her that things would never get better. My actions let her know that she was right, when she told herself that no one would ever care about her, but she’d already been thinking it for years, so she wasn’t mad or depressed about it, she was… She was just so quiet.”

Lucy put her head on my shoulder, and the two of us spent the rest of our bus ride sitting in silence, but somehow feeling her hand in mine made my sadness abate, just a little, just enough to be manageable.

“This is my stop,” she said. I climbed off after her, since my apartment was only a block away, but I was surprised at what was waiting for us when we stepped off. There wasn’t a dorm or apartment building, like I had expected, but an RV.

“What do you think?”

“I’m confused,” I told her.

“My parents think that the checks they’ve been sending me have been for rent. They’ve actually gone towards paying off this baby.”


“I know, right? I paid it off two months ago, and I’ve been stockpiling gas money ever since.” She pulled it open and stood in the doorway. “I’m actually heading out, on the day after tomorrow.”

I looked at her, with shock. “Seriously? You’re just going to leave school?”

Lucy nodded. “You think I’m crazy, too?”

“No, I just… You’re just leaving?”

“Yeah. It makes it even more funny that you showed up so close to me right before I left. I guess fate is just stupid and inevitable like that.”

We once again sat in silence, but, this time, it was only because I was completely at a loss for words.

“His name was Ethan, by the way.”


“The guy who taught me about heartbreak. He was the reason I knew what you were going through. I was fifteen, and he was…”




“Yeah, I don’t usually tell people about that, but you were honest with me, so…”

“So, we’re even?”

“Or close enough.” She chuckled and turned back to the piles of clothes sitting behind her. “I have to go. I have a few more things to get ready,” she told me. “It was nice knowing you, Alex.”

“It was nice knowing you too, Lucy.”

She turned around, but stopped to tell me one last thing. “You know, I’m still feeling a little crazy. If you want to stop by later, maybe you can help me get it out of my system.”

I smiled. “I might just take you up on that.”

She smiled in response, and then shut the door, going back to preparing for her trip.

Once Lucy was gone, the very first thing I did was pull out my phone. I had a long overdue apology text to send.

“Hey, Emma. Sorry I’m an idiot. I made a complete ass of myself and I’m so so so so sorry. Please, text me back so we can do some drunk driving.”

I came out of the elevator at my apartment building, with my eyes still locked on my phone, and sent the text just before getting to my door.

“Sending something important?”

I recognized Annie’s voice, instantly, but I hadn’t noticed her standing at my door.

“Oh, I’m just sending a text to Emma. Not sure if you noticed, but yesterday I was kindof-”


“Sure, let’s go with that.”

“Well, it was nice seeing you again, all the same.”

She looked at me and I remembered how beautiful she was. It had been a while since I had seen her last. Or at least, since I’d seen her with sober eyes. “To be honest, I barely remember it, or anyone who was there.”

“Well, luckily, Kendra skipped that game. I would have said something, but Emma kindof dragged you off and I was too scared to say anything, with you being in that state.”

“Let’s just not talk about it,” I told her. “It’s over, now.”

It seemed like I was about to be plunged into yet another awkward silence, for the thousandth time that day, but I was surprised when Annie kissed me instead, wrapping her arms around my neck as she did so.

“What was that for?”

“Because I missed you. I haven’t even been back to that one Italian place since we last went there on that double date.”

“Oh, shit. I’d almost forgotten about that.”

She laughed, but then stopped to look at me with her big beautiful eyes. “So, it’s getting late, and I have a pretty long walk home. Any chance I could spend the night over here?”

I wholeheartedly said yes and started unlocking the door, before I suddenly stopped, and told her “I have another idea, if you’re up for it.”

Five minutes later, the two of us were down the street knocking on the door of Lucy’s RV, and I had one single question waiting for the moment she unlocked the door.

“How crazy do you want to get?”

Soon after I had collapsed onto the bed in Lucy’s RV, lying back on a pile of blankets and unpacked clothing, as well as a surprising number of stuffed animals.

Both girls approached the bed, squeezing through the narrow space, before sitting at my feet.

It was painfully apparent that neither Lucy nor Annie had much experience bedding other girls, as they looked at one another, wondering how exactly to initiate this incredibly foreign, but still new and intriguing experience.

To my surprise, it was Annie who made the first move, planting her lips on Lucy’s in a single bold advance, just as she had to me a few minutes earlier.

Lucy’s hands awkwardly ran down Annie’s shoulders, as she tried to figure out exactly how to touch and caress this new type of lover, but she soon found her stride as she watched when the goose bumps appeared on Annie’s skin. She ran her hands down the back of Annie’s neck, along her inner thigh and gently traced one finger along the neckline of her shirt. However, just as Lucy’s finger finished moving along her bust and back up to her shoulder, Annie suddenly pushed her onto the bed, pinning Lucy under her as they continued kissing.

It stopped moments later, though, as Annie pulled away, looking red-faced and shy once again.

Lucy, however, was in shock. I could almost feel her heart pounding, after Annie was so forceful with her, but one thing was clear as I looked at the expression on Lucy’s face; she hadn’t disliked it.

While I think it was clear that neither girl’s sexuality was going to be permanently altered after this, it was also apparent that they were both having fun, and so I decided that it was about time for me to join in.

I was barely able to get my zipper halfway down before Lucy came over to help, and Annie wasn’t far behind. Both girls set their tongues to work as soon as I was relieved of both my pants and my underwear, with Lucy taking the base of my cock and Annie teasing the head.

“Fuck, have you two done this before?”

They looked at each other with just a dash of pride in their eyes, and Lucy even pulled away to plant a quick kiss on Annie’s lips, before immediately returning to pleasing me.

When her partner turned away, Lucy was quick to take her position, at first licking the precum from my tip, before swallowing the entire rod. She had absolutely no trouble taking me deep into her throat.

I heard a loud and wet plop as I suddenly slipped from her mouth, and looked down to see that Lucy was shuddering in pure ecstasy. Behind her, Annie was down on all fours, her face buried in Lucy’s cunt.

I got up off my back and stood on my knees in front of her, and as Lucy’s mouth continued to hang open in shock and pleasure, I gently slipped my cock inside. She was glad to receive it, only moaning louder as I began to softly push myself in and out of her mouth. Though her lips were already smooth and wet, I only further saturated her with the precum, the taste of which she had fallen in love with.

I didn’t ever want to pull out of her, but as I felt her body begin to tense, I yanked my cock free just as Lucy collapsed on the bed, a wet stain growing beneath her tired frame, and, more specifically, her pussy lips, which had been widened by Annie’s tongue.

However, Annie and I didn’t plan on letting her rest. We quickly switched positions, letting Lucy roll onto her back as we did.

“Oh, I’m going to be sore, tomorrow, aren’t I?” she asked, as she saw me lining my member up with her already sensitive cunt.

“You know the answer to that.” Those were the last words I could say to her, before Annie lowered herself down onto Lucy’s lips, her face instantly perking up as Lucy’s tongue snaked it’s way inside of her.

Annie wrapped her arms around my shoulders, forming a triangle with Lucy as the base and Annie and I sloppily kissing at the peak. All I had to do was connect the last piece, which I was happy to do, pushing my way into Lucy’s wet pussy.

I could hear her moaning, even though her mouth was filled with Annie’s cunt. Lucy wholeheartedly lapped up the juices of her fellow cheerleader, while spreading her legs for me to penetrate her pussy, and seeing her breasts move up and down with each thrust made the arousing sight even hotter.

“I’ve never had another girl do this to me before,” Annie admitted.

“Do you like it?”

She was so breathless that it was hard for her to answer, though soon after she did manage to mutter out something else.

“Alex, I’m going to cum.” The thought of her cumming from her first girl-on-girl experience only made my cock stand further at attention.

I pressed my lips back against hers just as her orgasm gripped her, and Lucy came only seconds later. The sighs of both girls turned to moaning, which turned to screaming out in pleasure as I thrusted with yet more force and speed, and Lucy buried her tongue even deeper inside of Annie.

Everything came to a head, when Lucy seemed to pass out from exhaustion, and Annie finally climbed off of her face.

Before she even knew what was happening, I grabbed Annie by the hips, noticing something strange.

“Oh, fuck,” she said, as I gently tugged on the plug lodged deeply in her rectum.

“I hadn’t noticed this, before,” I told her. “It looks like you came to my apartment prepared.”

She once again turned bright red, but also didn’t deny it.

With a single tug, I yanked it out of her, and quickly slid the plug into Lucy’s butt, for safe keeping. I then lifted Annie into the air, my arms firmly gripping her knees, holding her just inches above my waiting manhood.

“What are you doing?” she asked, mostly out of shock. She knew what was about to happen.

“Annie, your ass is, hands down, the tightest hole I’ve ever been inside of, and I’m about to fuck it until it’s wide open.”

I didn’t even wait for her to respond, I just lowered down until my head was pushing against her entrance.

“I think I might be too tight,” Annie said, as we struggled to open her up. “We may need to-” She suddenly stopped, as my head finally pushed its way inside. “Fuck.”

Annie continued to cry out as I gently thrusted, trying to force her open enough to let me fully penetrate her, and just as I finally felt her consume my entire cock, she cried out once again.

“Should I stop?” I asked her, before realized that I wasn’t the one who had caused it. Lucy and gotten off the bed, and, once again, was eagerly nibbling at the outer folds of Annie’s pussy.

After seeing that, I couldn’t hold back any longer, and pulled my hands up behind Annie’s neck and her knees up past her head, holding her tight little body in a full nelson, with my cock still deeply lodged in her ass.

“Oh, god,” she whispered, anticipating the feeling of having her tiny hole ripped apart.

“You ready?” I asked her.

“As I’ll ever be.”

Slowly at first, I pulled out and gently pushed back into Annie’s butt, her rectum slowly opening up more and more, and allowing me to speed up.

“Fuck!” Annie screamed again, as Lucy redoubled her efforts to please Annie’s cunt, and I fucked her harder than I ever had. Cum was already leaking out of her, and seconds later she squirted onto Lucy’s face, soaking the other cheerleader with her juices.

Annie didn’t say another word for the rest of the night. She simply moaned in pleasure as Lucy and I had our way with her.

“Fuck, you’re still so tight,” I said, pounding her butt hard enough to turn her cheeks bright red. Even with all the time spent loosening her up, it still almost hurt to fuck her, with how tightly her tiny hole gripped me.

A second orgasm gripped her, and I felt Annie convulse in my arms, though she couldn’t move much.

Lucy pulled away from her, both to allow Annie a slight break and because she knew I wasn’t far behind.

I could feel a swelling in my sack, as my cum built up more and more. I held on as long as I could, never wanting to pull out of Annie, but soon I knew I would have to, and as I took my final thrust and let myself fall out of her, Lucy opened her mouth, glad to take my cum.

Annie was so weak that she could barely move, so I had to be careful as I lowered her onto the bed. Lucy and I both shared a smile as we looked down at her, with her cunt that was still wet and tender, and her red, raw and gaping asshole.

I laid down beside her, and Annie quickly wrapped her arms around me, nuzzling into my chest and immediately falling asleep in my arms. Lucy laid down on my chest as well, lazily running her fingers up and down my stomach as she did.

“You know, you could come with me,” she said.

“What do you mean?”

“Well, I might get lonely driving across the country. I could use someone else.”

I didn’t answer. The thought of just leaving school to drive somewhere and not come back was completely foreign to me.

“We won’t be inviting other girls over all the time,” she said, looking over at Annie’s sleeping form. “But, we can once in awhile.”

I smiled. “That’s pretty tempting, but-”

She stopped me by placing a kiss on my lips, long and sensual, as her fingers continued to dance across my skin.

“I really like you,” she told me. “But, I can’t stay here. Being away is what I need, and I think you need it too. No more seeing old lovers you don’t want to see. No more seeing old friends who promised to love you. No more seeing Kendra, period. No more pressure. No more drama. Just you and me, doing anything we want.”

“I don’t know,” was all I could say, but that seemed be enough to sate her.

I was confused and torn, but decided to wait and figure it out, later. For now, I just enjoyed the feeling of these two beautiful figures pressed against me, and drifted off to sleep.

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The Cheerleader Harem: Part 14 [Final]

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Comments (3)
Jim altop — 06 December 2017 12:37
This is the end????
Rich Richardson06 December 2017 18:39
Well, there's a framing device in the full novel that starts and ends the story more cleanly, but there really isn't a good way to put that here, given the formatting that I have to work with.

I'm doing my best, but perhaps I just shouldn't have bothered to post the new chapters at all.
thejmanlt — 11 December 2017 07:20
It was a pretty confusing ending to a wonderful series, to be completely honest, because it didn't really resolve the issues that was presented. Like, for instance, does Emma reply to the apology text? Will they be friends with benefits again, or will they just revert back to being just friends? To leave the audience hanging for answers to these questions is like the ending to inception.
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