Cherry on Top Ch. 01

Story Info
Monday. Cherry gets caught with a pen between her legs.
2.9k words
4.4
28.6k
35

Part 1 of the 13 part series

Updated 06/12/2023
Created 12/26/2022
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All characters are at least 18 years old.

------

Cherry

My dad continued stroking his cock, looking at me with lustful eyes. The hand I had down my pants wasn't enough. I needed him. It didn't matter that he was actually only looking at a polaroid of my mom. It didn't matter that I was actually only watching video footage of him doing all this. In the moment, it felt like he wanted me.

"Cherish! You ready for school?"

I hastily turned my phone off and pulled my hand out of my jeans, wiping my fingers on the dark denim. Nasty, I know, but I couldn't have dad knowing I was touching myself first thing in the morning. "Yeah, one sec!" I called back. Hauling my backpack, I walked into the kitchen to see my dad finishing up his coffee. I couldn't get the image of him stroking himself out of my head. He glanced at me and grew a worried expression.

"You okay, princess?" he asked. "You seem... out of sorts."

Yeah, I can't get your cock off my mind, you sexy man.

"Just tired, I guess," I lied.

He grunted sympathetically. "Gotta watch those hours, hon." He petted my copper hair before nodding toward the front door. "Bus is almost here. Better get going." He kissed me on the forehead and ushered me out. "Have a good day. I'll see you tonight."

I looked back at him, with his chestnut hair and five o'clock shadow. It's infatuation, Cherry. I had to remind myself every day. It's not like I was in love with him or anything. That'd be weird. Giving him a wave, I walked out to the curb, where I saw my neighbor Drew already waiting. He was an exact foot and a half taller than me, but then again, being under five feet tall made me shorter than a lot of people.

"Morning, Squirt," he said, and I scowled. I detested every name people called me, especially Squirt. Drew was just a walking reminder of how short I was. So much for any hopes of being a model.

"Stilts," I growled in greeting, and he grinned. The prick. In all honesty though, he was a good guy. He'd never actually tried to make me feel bad. Just couldn't help giving me a nickname, which I guess was... tolerable.

The bus arrived and we both got on. We sat separately, and after a few stops a pair of twins boarded. Stefan and Sabrina. Stef found his usual seat next to Drew, while his sister sat next to me.

"Hey Brie," I said.

"Hi Cherry. Morning," she replied, making sure her black hair was tight in her ponytail. "Did you see Draco's new movie coming out? It looks so good!"

"You mean Providence?"

Brie nodded emphatically and began babbling about the newly released trailer. But I was dying to talk to her, really talk to her. I didn't know who else to talk to about my dad. Drew? This past Christmas, there was a moment where it seemed like my dad and Drew's mom might've hooked up, and it scared the hell out of me. How was I supposed to talk to him?

I could just never get Brie alone. Discussing something so scandalous on the bus was out of the question. School, lunch, extra-curricular sports... And anytime Brie was free, she was hanging out with her brother. They'd started hanging out a lot a few months ago, right around the time they'd both started dating. After hearing about how protective they were of each other, it came as a shock to everybody. And oddly, nobody could figure out who they were dating.

"You okay, Cherry?"

"Huh?" I snapped back to attention, and Brie was looking at me intently, her head cocked. Another name I hated. I disliked Cherish even more, so Cherry was the nickname that most people used. Naturally I got teased a lot at school by the mean girls, taunts about nobody wanting to pop my cherry. Unlike them, I actually valued my virginity. In fact, I was saving it for somebody.

"You're spacing out," Brie continued.

"Sorry, sorry. I just... There's something I wanted to talk to you about," I stammered.

Oh God, how was I gonna broach this subject? "Hey, I've been thinking of banging by dad. Any advice?" Fat chance. On top of that, she and Stef had basically been disowned by their own dad just last summer. But the rest of our friends were even less likely to be open about this. I had nobody else to turn to.

"Sure. What's up?" she asked.

Fuck. I looked around at the other kids sitting around us, including Stef and Drew. "Maybe not right now."

"Alright. Maybe at lunch then? Come sit with us, I'm sure between the five of us, we can figure something out."

I was about to tell her that I wanted to speak to her alone, when we arrived at school and Brie stood. Damn it. We alighted together and headed to class, where I was tortured with sinful thoughts of my father.

--

The cafeteria wasn't as packed as usual. Quite a few of the other seniors were skipping school now that our college applications were submitted. Most of us had gotten our admission letters back too. Stef and Brie were going to the local community college to save their mom money, since after her divorce she was left with almost nothing. But then Drew had surprised me by announcing that he was doing the same, no reason given.

I carried my tray through the tables, passing Lauren and her friends. Lauren was the alpha bitch of her pack of she-wolves. Thankfully, they didn't seem in the mood to bully me today, and I got around them safely. My friends that I usually sat with were all together already, and they beckoned for me to join them. I shook my head and tilted it to point at my destination.

Brie was sitting with her brother. Stef used to just sit with Drew, but a few months ago the twins had started taking lunch together as well. And seated next to Brie was her best friend Lexi.

Put simply, I didn't like Lexi.

She was beautiful, and rich, and flirty all the damn time. She also apparently spent no time studying, yet made grades good enough to pass. The golden child, in some respects. And it didn't seem like many other people noticed, but she always had this look in her eye that made you think she was seeing right through you and into your soul. It was unsettling.

"Hey, guys," I stammered. "Mind if I join--"

"Hey Cherry!" Brie said. "C'mon, sit down!"

The boys were sat across from the girls, and everybody's schoolbags were piled between Brie and Lexi, so I took a seat next to Stef. The others greeted me, and I shyly said hello to everybody. Ugh, why was this so weird? The conversation between the others continued, and I leaned over to Brie.

"I actually wanted to talk to you, like... alone," I muttered.

"Oh. Um, sure. Well I have work after school, so you can swing by then. Know where it is?"

I nodded, and she smiled and turned back to the others. Drew was speaking, and it took me a moment to figure out what he was talking about.

"...so yeah, they locked him up anyway. Turns out they don't care if you've got no eyes or dick, you still go to prison." My eyes widened. This was the kind of stuff they normally talked about? At lunch?! "Still kinda annoyed I didn't get to do it myself though." Drew looked pointedly at Lexi, who giggled. Brie looked slightly unsettled but said nothing, while Stef grunted in agreement.

"Those fucking fathers, am I right?" he added, which got a resounding response of consensus. Fucking fathers indeed, I thought to myself, mind flashing an image of my dad's erection again. Damn, I really shouldn't think such things in public. What if somebody could tell?

"I guess all of us have daddy issues," Lexi summed up, gaining a dirty look in her eye. "And not even the fun kind."

I froze, even as the rest of them broke out into laughter. That's right, I remembered. Stef and Brie's dad had cheated on their mother and left them with nothing last summer. Drew's dad had walked out on him and his mom before Drew was even born. And apparently Lexi wasn't on talking terms with her own father either. I suppose I was the only one with the "fun kind" of daddy issues, and I squirmed in my seat.

Everybody else was laughing, before moving onto a different topic. But one of them had spotted my reaction. Lexi Rochester's stormy grey eyes were boring into me, and I gulped. She smirked, gave me a wink, then turned back to the rest of the conversation as if nothing had happened. God, did she know? Maybe she just thought I was appalled at her sense of humor.

No. She knew. How?

It didn't matter how. She knew.

--

I looked up at the sign to verify I was in the right place. Brie worked at a clothing store after school, which seemed to be rubbing off on her because she had a few new outfits that were very stylish. Maybe she had started dressing up for her boyfriend.

I took a deep breath, still unsure of what to say to her. I'd decided I was overreacting with the way Lexi had looked at me. She just wanted to tease the new girl, so to speak. All the same, I needed to tell Brie of my dilemma somehow. Unfortunately, my plan was to just wing it. I stepped inside, and Brie beamed at me as I approached the counter.

"I was wondering when you were gonna come in," she said with a grin. "You've been pacing outside for almost five minutes."

"You saw that...?" I mumbled with a blush, nervously twirling a strand of hair. My dad joked that all the twirling was why my hair was so wavy. I reckoned pretty soon I'd have curls.

Brie smiled warmly before turning more serious. "What's up? Something important, apparently. Everything okay?"

"Yeah. Yeah... Just... don't know where to start."

"Take your time. I'm not going anywhere." She propped her head on the counter, humming a bit while I got my bearings.

"...There's this guy I like," I began slowly. "And I want to... ask him out, but I'm afraid he'll turn me down. And then it'll ruin whatever we already have now, y'know?"

She nodded sympathetically. "That's a toughie. You'd probably have to start slow. Give him hints and all that, and gauge his reaction. You worried you're in the friend zone?"

"Something like that," I managed, sounding a bit strangled. "Damn, I really don't know what to do. How did you get together with your boyfriend?"

She blinked. "Me? Oh. Uh... Well, I was lucky 'cause he initiated. And even then, I wasn't sure how to act. Took me a bit to really get into it." She swallowed, diverting her gaze. Heh, she was shy too. That gave me some small comfort. Brie was gorgeous, which was probably why Stef had to work so hard keeping guys away from her. To see her so thrown off by a guy... Guess it happened to the best of us. "Sorry, I'm not sure I'm really the best person to give you advice on this," she chuckled. "My situation's a bit different. How about this? Why don't I talk to this guy of yours, feel him out?"

"Or maybe I can," came a voice from behind me. I turned to see Lexi standing at the door of the store, a cocksure smirk on her face. God damn it, not now. She sauntered over to us, leaning languidly on the counter.

Brie put her hands on her hips. "Private conversation, Lex," she said sternly, earning a grateful look from me.

"Not gonna stop me," Lexi replied brazenly. "I may not have the biggest nose in the world, but I love sticking it in other people's business." She grinned impishly, and I scowled in response before she leaned in toward me, dropping her voice to a croon. "And you're not gonna be able to get what you want without a little help."

Her words sent chills down my spine and I stepped away, putting on a brave face to glare at her. Her grin was infuriating. "I don't need your help," I said coldly.

"Lex, c'mon, leave her alone," Brie chided.

"Do you trust Brie?" Lexi asked suddenly. She caught me off guard, and I blinked before slowly nodding. She turned to Brie and asked, "Do you trust me?" Brie looked about as shocked as I did, then looked at me apologetically before also nodding. "Perfect."

"Trust isn't one-dimensional, Lexi," I pointed out. "It's not linear like that. There's no such thing as trust by proxy."

"Very true," she concurred with a wink, then leaned in again and whispered in my ear, "Then you plan to seduce daddy all by yourself?" My blood turned to ice. When she straightened she was holding back a laugh, and I was too busy remembering how to breathe to be angry at her. "I'll take that as a no," she lilted, before turning to leave. "I better get to work now. I'll be in touch!"

And then she was gone. Brie turned back to me quizzically. "What did she say to you?" She hadn't heard what Lexi whispered to me.

"What the fuck just happened?" I responded, brushing past her question.

She looked at me strangely before chuckling once and looking back out the store. With an ominous tone, she answered, "Seems you just piqued the interest of Lexi Rochester."

--

After taking care of the mundanities of handling the groceries and cooking dinner, I decided to check in on my little bit of spyware. My dad kept his home office unlocked, which had made things astonishingly easy. I looked at the picture frame positioned on the mantle behind the desk and just askew to the left, which had given me a good side view last night. I hadn't been able to find a spy camera that could record footage, but it streamed directly to my phone, which was almost better. From there, I could capture my phone's screen footage. Thank God for smart phones.

I sat down in the chair, letting my gaze pass steadily across his desk. It ended at the middle drawer, and I leaned over and opened it. At the very back was a polaroid that I'd never seen in person before, of a woman. I didn't even know it existed until last night.

It was a photo of me. Except... older, taller, in a place I'd never been before. It was taken by a lakeside. The woman in the photo looked happy, the type of happiness you could only get from growing up with a loving mother. I swallowed, a sense of longing growing in the pit of my stomach. At the bottom was a single word. Rose.

Dad never talked about mom, not even when I asked. I gave up trying to glean any information from him a long time ago. He didn't even have any photos around the house, just pictures of the two of us. All I knew was that she died when I was very young, and he had loved her very much. Today, I finally learned her name, and that she looked almost exactly like me. Or I looked almost exactly like her, rather.

He hadn't been thinking of me last night, I realized sadly. I mean, I already knew that. I knew I wasn't the one in the photo. It was just disheartening regardless. I picked out his favorite fountain pen, admiring its simple yet elegant design. Dad said he'd always liked fountain pens, ever since he was a boy. He liked signing with them because as a youth he thought they looked fancy-schmancy. It was things like that, things that showed the mature and responsible man who'd raised me was in fact also a bit of a dork, that probably contributed to me falling in love with him.

Wait, no, it wasn't love. I brought the fountain pen between my legs, pressing the end of it against my panties. It was just puppy love. Idolization begotten from familiarity. It was only because he was the first man in my life, the paragon of masculinity. He was strong but gentle, kind yet stern. I rubbed the pen against my clit, groaning and leaning back in the chair. Ten years. Ten years of being in love with him, and I could do nothing but watch as he went on a date with Ms. Hammond, Drew's mom. On one hand I was glad he still missed my mom so much that he hadn't remarried or anything. On the other, was he still so in love with her that there was no space left in his heart for me?

He loved me, but as a dad. I just didn't know if I could live without something more.

"Dad..." I whispered desperately, flicking my clit fervently with the pen.

"Cherry?" he replied, and my eyes popped open. He was standing in the doorway, briefcase in hand, tie undone, and looking sexy as fuck. And he was looking right at me as I masturbated at his desk.

Fuck.

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4 Comments
TwistedOne66TwistedOne66over 1 year ago

I'm holding off on reading this until you finish the series. Please keep them coming. I'm really enjoying your work.

AnonymousAnonymousover 1 year ago

What kind of fucked dad wouldn't atleast have pictures of her mother around for her to see and keep her memory alive for the girl? Brie is fucking her brother and lexi was fucking her dad but he's no longer in the house and she was the cause.

AnonymousAnonymousover 1 year ago

Tell the first anonny to fuck off. Dont let douchebags get to you. This is an interesting premise. Yes hopefully dad will dick her down, but I'm really interested in the Lexi aspect. Is she banging Brie? Or one of the others? And how does she know? Intuition like that usually comes from experience. Is her dad plowing her? Or does she have her mom lapping between her legs? I'm very intrigued to see how Lexi guides Cherry through seducing her dad. And does the gateway to Lexi's assistance lie between her legs. Theres many questions that need answered here, and anonny doesn't have the wherewithal to grasp that. 5 stars and can't wait for more.

Dewey Cheatham

AnonymousAnonymousover 1 year ago

Is today crummy father/daughter incest stories day? Because there sure seems to be a lot of them.

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