Cherry the Cheerleader - Cover

Cherry the Cheerleader

Copyright© 2024 by MikeHuntHZ

Chapter 13

Romance Sex Story: Chapter 13 - Boy meets girl. Boy and girl fuck. Boy and girl fall in love, get married, have kids. BUT... it's not quite that simple! If you are a fan of a well-written love story that has plenty of twists and turns, and plenty of sex, then this book is for you! You'll laugh, cry, and root, root, root for the home team in sexy journey of friendship and love. And, if you grab the entire eBook over on Bookapy (under $5!) you won't have to wait, and, you probably won't put the book down!

Caution: This Romance Sex Story contains strong sexual content, including Ma/ft   ft/ft   Consensual   Romantic   Lesbian   BiSexual   Heterosexual   Fiction   School   Workplace   Group Sex   Anal Sex   Cream Pie   Exhibitionism   First   Masturbation   Oral Sex   Petting   Pregnancy   Sex Toys   Voyeurism  

My joke earned me multiple, justifiable punches to the arm and a few more to my ribs.

Cherry finished punching me before she went back to hugging my arm and huffed, “I am NOT a lesbian!”

“I know ... I’m just playing with you, Babe,” I said while wrapping both arms around her.

We sat in silence for a while; Cherry seemed to be carefully weighing her thoughts as we simply enjoyed each other’s company. I was still digesting the new information about her history with Olivia and it was a little shocking to say the least. I thought about everything I said in my initial reaction to the news and saw no reason to second guess my position. Then I realized something and wanted her to confirm my suspicion.

I said, “So, you never dated any one before me—it was always you and Olivia until now.”

She said, “Yeah, that’s true.”

“That means you started out by wanting your first kiss from a boy you liked, and ended up having Olivia as your first kiss.”

She reflected for a moment and said, “I never thought about it that way, but I guess that’s true, too.”

Cherry then asked me, “When do you want me to give you an answer on what I decide to do about her?”

I said, “You don’t owe me an answer about that and I don’t expect one. If you want to tell me, that’s fine with me. And if you would prefer to keep it between you and her, I won’t take that as you keeping secrets from me. It’s all up to you in how you choose to handle your friendship with her—I’ll never ask you what you decided if you don’t tell me.”

She said, “I’m going to tell you. I just don’t know yet what I’m going to decide. Besides, this is something that I’m going to have to talk about with her, too; she has just as much say in what happens, you know? She might not even want to have things go back to how they were between us.”

I told her that was ‘fine’ and we ended the topic. We talked about nothing in particular after that and kept the conversation a bit on the ‘light’ side. It went without saying that finding a private spot to have sex was not a good idea at the time: it was getting late and, more importantly, with her being on her period, sex would make a mess that would be impossible to clean without the use of a bathroom and a change of clothes. Besides those obvious points, I found that being together and NOT having sex seemed to actually build the love that I felt for her.

The sun was painting the clouds in hues of pink and purple when a voice from behind us interrupted us. Neither of us needed to turn around to know who it was.

“Cherry, we have to go: it’s getting late,” Olivia said.

Cherry looked over her shoulder and asked, “One more minute?”

Olivia began walking away before she said she would be in the car waiting. Cherry thanked me for coming to watch her practice and gave me a kiss. It wasn’t a passion filled kiss; rather, it was a really sweet kiss as if to say ‘thank you for listening, understanding, and being supportive’.

She asked if I would be at the game and I told her that I would be (of course). Before going our separate ways for the evening, we told each other ‘I love you’ and shared one more lingering kiss.

Just as I was about to park in front of my apartment, Cherry texted me and said she and Olivia were ‘talking’. I knew what that meant; I wasn’t going to disturb them with texting or phone calls.

A while later I received a text that said, if I was sure about my position, they were going to try and go back to the relationship they had before I came into the picture. I just texted back ‘I’m sure’. She sent me a string of heart emoji icons followed by faces with puckered lips; I just replied simply, “U 2!”

It gave me half a ‘chubby’ to think my gorgeous girlfriend was probably making out with a very attractive lesbian; what straight guy hasn’t watched at least a half million porn videos with that kind of content?! I knew for Olivia it was just a way of feeling some kind of intimacy when she is otherwise alone and Cherry was just helping as a friend, but the thought was still hot!

I went to bed hoping I’d dream of Cherry and Olivia making out. Instead, I dreamed of Katie. I found her sitting on a swing in a large playground. She wasn’t swinging as a young girl would normally do; she seemed to be waiting for me.

As I sat on the swing next to her, the sounds of children laughing and playing filled the air. Strangely, however, Katie and I were alone. I was looking around to see where their voices were coming from when Katie spoke.

“They aren’t here,” she said stating the obvious.

I said, “You hear them too, though?”

Katie said, “Yeah, I hear them. That’s why I came here: to see if they wanted to play. But it’s like they are here—but NOT here. What do you think that means?”

I shook my head and answered, “I don’t know, sweetie. Maybe it means they aren’t ready for you yet. Or, maybe you aren’t ready for them. Maybe it doesn’t mean anything.”

Katie thought for a moment and said, “It definitely means something. I just don’t know what it is.”

I offered, “Maybe it’s up to you to decide what it means.”

Katie looked at me and asked, “What if I’m wrong about what it means?”

I said, “You won’t be wrong. Sometimes things mean different things to different people and it’s up to each of us to figure it out for ourselves.”

She asked, “Can I think about it for a while?”

“Of course; you can take as long as you need,” I answered.

She nodded slightly and said ‘ok’ before she started to glide back and forth—just a little—on the swing set. The quiet sound of the squeaking chain seemed slowly replace the laughter of the children that could not be seen; their play fading into silence. Neither Katie nor I made mention of the voices leaving as we sat thinking about what it all meant.

After sitting in silence (except for the sound of the chain) for a long time, I could feel it was time for me to leave, but I felt bad about leaving Katie by herself, so I stayed to keep her company.

Katie said, “It’s ok David: I know you have to go.”

I said, “I don’t want to leave you here all by yourself...”

She replied, “I’m not by my self—Mama is here too.”

I nodded and said, “Ok; are you sure?”

Katie smiled at me and said, “Thank you for talking with me, David.”

I smiled back at her and said, “Any time you want to talk, you know where to find me.”

Katie and I said ‘goodbye’ and I started to walk away. Her swinging picked up pace a little and the chain began making a double ‘squeak-squeak’ sound. Ironically, the further I walked, the louder the double squeak became. I slowly drifted into consciousness and the sound of the squeaking chain was replaced by my beeping alarm clock.

I turned the annoying alarm off and began my day. The day was fairly uneventful as per usual: nothing exciting happens when you spend the day doing ‘domestic chores’ around a tiny apartment. And, I knew Cherry wasn’t going to have practice after school, so I couldn’t even look forward to that. I decided to surprise her again like I did the week before and visit her in her room; I’d just have to be careful not to fall asleep this time!

After deciding to go see her that night, time seemed to come to a grinding halt. We texted and talked as much as we could while simultaneously trying to keep it to a minimum to avoid raising suspicions with Cherry’s Mom. Eventually night fell and I found myself in Cherry’s neighborhood around 10:30.

I saw that the light in her room and bathroom were the only lights on in the house, so I was pretty sure her Mom had gone to bed already. I parked down the street as I did before and made my way back to her place, hiding in the bushes in front of her window.

Peering into her room, I saw that she must have just finished taking a shower: she had a towel wrapped around her and she stood in front of her mirror while blow-drying her hair. I knew not to knock on the window until she finished because her Mom would hear me before Cherry could. So I patiently waited while admiring the view of her fantastic legs as they disappeared up into the bath towel that just barely covered her ass.

Before Cherry finished drying her hair, I received what, in hind sight, should not have surprised me as much as it did: A naked girl walked out of the bathroom while drying her hair with a towel. I didn’t even realize my mouth was hanging open in shock until drool ran down my chin. She wrapped her hair up in the towel and perched it on top of her head and it was only then that I realized it was (of course) Olivia.

In many ways, Olivia’s body was what I expected it to be: she was in excellent shape, but not quite as tone as Cherry. One thing that did surprise me was her boobs—they were much smaller than I thought they would be. Clearly she wore miracle and push-up bras to make the most of what she had. Despite their small size, they were nicely shaped and seemed to look better on her than the B size cup she passed off.

Cherry turned her hairdryer off and Olivia walked right over to the window in front of me. For a moment I thought she was about to bust me looking at them, but the she knelt down and picked up something on the floor there. She stood upright as she removed the towel on her head. She was literally inches away from me; separated only by a pane of glass and a sheer curtain.

Only the darkness outside and the light in the room kept her from being able to see me. I could clearly see almost every detail of her body—given enough time, I could have counted the bumps on her areolas and it was readily apparent that there was not a single hair to be found ‘south of the boarder’. Olivia pulled an over-sized t-shirt over her head that came down to about mid-thigh.

For a moment, I wondered if anyone would call the cops on whoever it was banging on that drum so late at night; then I realized it was the sound of my heart thumping. I knew on some level of subconscious that my position would be impossible to explain away if I got caught. But at the same time, I couldn’t look away.

Cherry was walking back into the bathroom as she dropped her towel; giving me a brief view of her ass before she disappeared. Olivia turned around and walked away from the window, allowing my heart to slow down to a more normal rate. She began brushing her damp hair out and, before long, Cherry came back into the room wearing a pair of ‘boy short’ panties and nothing more. She sat on her bed and offered to finish brushing Olivia’s hair for her.

Olivia accepted the offer and the two sat on the bed, both facing me. Olivia sat with her legs crossed and her shirt was pulled tight to cover her otherwise naked butt. From the angle she was sitting, I once again had a clear view of her vagina and even more of it this time. Olivia clearly preferred to wax: she didn’t even have stubble—she was as bare as the day she was born!

Cherry took her time combing Olivia’s hair and the two of them talked about their arrangement and discussed how to handle any ‘issues’ that might come up. Olivia was still shocked that I was fine with their relationship continuing and that led into Cherry telling her how “wonderful” I had been. It was nice to hear her singing my praises when she didn’t even know I was there to hear it. They spoke softly and quietly.

Olivia asked out of the blue, “What’s it like?”

Cherry responded with her own question, “What is what like?”

Olivia elaborated, “Being in love. You are in love with him; I can tell. What’s it like?”

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