Cherry on Top Ch. 05

All characters are at least 18 years old.

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Cherry

Brie looked at me curiously. "You gonna steal my bestie, Cherry?" she joked.

Everybody's schoolbags were piled between the boys today, which meant I could sit next to Lexi. Probably a conscious decision on her part, since we had stuff to discuss. Lexi waved her off, and Brie instead turned her attention to Stef, who was roughhousing with Drew again.

"You didn't text him anymore after that, did you?" I asked Lexi as she whipped out a smart phone. Only Lexi fucking Rochester would use a smart phone as a burner. Obviously we weren't going to use either of our own phones to sext my dad, but this really was a bit much.

"You really don't trust me," Lexi laughed, opening the ComeDaddy app. Sure enough, the conversation between our account and my dad's was right where we left it last night. It was nerve-racking to have Lexi in my room while we discussed what to text dad at each turn. I had to admit, she was very considerate as she consulted me on everything she wrote. She didn't even ask to join me in watching the footage my spy camera afforded me. "But why not? You've already let me send your nudes to your dad."

Alarmed, I checked to make sure nobody heard, and she chuckled. "You mind keeping it down? This arrangement isn't exactly orthodox."

"You mean you and I? Or you and your dad?" she teased, only frustrating me more.

"Both. Just... Low profile, alright?"

"No promises," she lilted, and I sighed. I looked down at the conversation of my dad flirting with Lexi, which reminded me of something.

"By the way... How did you know that my dad was using a dating app? And how did you know which one he'd use?"

"I didn't," she confessed, bringing the burner phone back to its home screen and revealing a slew of dating apps. "So I just signed up for all of them. Well, at least all the pertinent ones. Should I have signed up for the gay hookup one too?"

She giggled when I grumbled in response. "But what's the plan? What's the endgame here?"

With a glint in her eye, she leaned toward me, and I shuffled away from her on the cafeteria bench. "Seeing your dad jack off to your naked body not enough for you?" she murmured. I felt my face burning up, and she smirked and straightened. "Endgame's exactly what you want."

That was daunting. Did I even want what I thought I wanted? "And what are you getting out of it?" Even though she seemed to be helping me, even though she'd kept my secret from everybody, I couldn't rein in my suspicion.

"I get to prove a point," Lexi said solemnly. Her demeanor had changed, feeling slightly dark as she said it. I decided to leave it alone; far be it from me to pry into whatever issues she was dealing with.

"Alright, well," I continued, "what comes next?"

"Does he have work tomorrow?" I shook my head. "Has he said anything?" I checked ComeDaddy. The last message was Lexi promising to talk to him today. I shook my head again. "Sext him. Something sexy."

"Here?" I gawked at her, and she rolled her eyes.

"No, not here, you silly bitch. I mean... unless you want to...?"

"No!"

"Didn't think so. Now c'mon." She finished the rest of her sandwich and stood to retrieve her schoolbag, and I followed suit before we said goodbye to our friends. Leading me to one of the restrooms, she ushered me inside one of the stalls and locked the door.

"This is so weird," I muttered. "Does it have to be now?"

"If you wait until after school, you won't have enough time to build up to what we're gonna pull off tonight," she explained.

"What? What's happening tonight?" I asked, eyes widening.

"The next step," she said simply, as if it was obvious. "Now strip."

I shirked away from her, instinctively clutching my arms across my torso. "In case you haven't noticed, I'm still not really comfortable showing somebody else my body."

"And that's just what we want," she replied. She dropped her voice, possibly to counter the echo in the restroom. "Why do you think your dad likes younger girls?"

"Because they have less experience?" I guessed.

"Not a bad answer, but painfully naive and unobservant." I growled at her, and she chuckled. "It's because he wants you, his nubile daughter." I gulped. "It's why he likes being called 'daddy' while he's jacking off. It's why he likes smaller tits. He wants his shy, demure little girl. And that's what you're gonna give to him. Shouldn't be too hard, since you're genuinely like this, so let's make the most of it."

With that, she raised the burner phone and snapped a picture of me. It wasn't helping my bashfulness, but like she said, that was the idea. I put my bag down and hesitantly took my t-shirt off to reveal my light pink bra underneath. Lexi purred appreciatively, and I heard the phone's shutter sound again.

"Are you into girls?" I asked curiously. "I mean, I've never actually seen you with a guy before, but you seem to be enjoying the hell out of this. I mean, yesterday you spent ten minutes trying to convince me to take my top off."

"That's 'cause it was for your dad. And so is this," she replied. "And yes, I'm enjoying this, but it's not about you. Or your dad, even, so stop thinking I'm out to steal him. Now hurry up and get that training bra off and let me--"

"It's not a training bra!"

"Coulda fooled me. Quit fussing and strip."

Soon I was topless, holding my arms across my chest. Lexi snapped a picture then clucked her tongue and took a moment to rearrange my arms, lowering one to just below my tits, moving the other to angle it diagonally between them. Both of my nipples were exposed and I felt so vulnerable, and before I could protest she captured the pose on film. Well, so to speak.

"Oh you poor girl," she lamented. "It seems you have not a single clue when it comes to the art of seduction."

"Y'know, I was gonna thank you for helping me with Lauren," I said bitterly, "but if you're gonna be no different--"

"I'm not making fun of you. But you have a lot to learn if you're gonna make this work."

"I've read some fanfics," I stammered.

She rolled her eyes. "Jesus Christ. Fanfics are a horrible example to learn from. There's no nuance, no sensuality. You need to entice your man." She let me look at the four photos she took, a steady progression of me disrobing. "Can't send him the first one, 'cause he probably saw what you're wearing today, right?" I nodded, and she deleted it. "It was to make you more shy anyway, so that's fine."

I was beginning to see how she manipulated me in order to get the results we wanted. Most of the time, people regarded manipulation as something negative. Was it still negative if somebody manipulated you for your benefit? When I'd given her permission?

"And here we see how you whet a man's appetite," Lexi explained to me. "See, you probably would've only sent one of these pics, right?" I begrudgingly nodded. "But we're gonna send him all three. Drip feed it to him and let his lust build throughout the day."

She attached the photo of me in my bra, then typed out a caption of sorts in the message field. She let me review it before sending, and I nodded my approval.

Me: Last night was so hot. Still thinking of you at school~

"And now we wait," Lexi declared with a smirk. "He's probably at work, and I doubt he'll respond to this first one. We'll send the second one after school, that'll definitely get a reaction out of him." She handed me the phone, and I looked at her questioningly. "In case he does reply to the first pic. Have you learned enough to know how to talk to him?"

"I-- Of course..." I hesitantly took the burner, my stomach churning. He was my own fucking dad, of course I knew how to talk to him. I think. Oh no, I was gonna fuck this up.

"If he does reply," she continued, looking contemplative. A smile slowly grew across her face, and she chuckled once. "That would be a pleasant surprise. And it'd make our plan easier." The bell rang, and she jerked her head toward the door. "Better get going, Lolita," she said with a wink.

Just great. Another nickname that made me uncomfortable.

--

It was halfway through class when the reply came.

I gulped and reached into my bag, sneakily slipping the burner out to look at the notification. Oh man, why did I have to bluff to Lexi earlier? I got the feeling she already had me figured out. What was the point of lying to her, especially when she was trying to help me? I peeked at the message while the teacher wasn't looking.

Leon: It was. You have a gorgeous figure, and it's embarrassing how much I enjoyed this new picture too

Leon: I'm also a bit surprised. You seemed a lot more bold on here than when we met at Colette's place

Fuck, what did I say to this? Of course Lexi had to be bold on ComeDaddy, she was trying to reel dad into this relationship. But that night at Ms. Hammond's place, my guess was she was trying to act as similarly to me as she could. She would've been shy and demure, just like she'd said earlier. So now there was a dichotomy between the two personas. I checked to make sure the teacher was still busy scribbling on the whiteboard before tapping out a response.

Me: ofc im more bold online. i dont have to look you in the eyes when i say all these dirty things

Me: and im not distracted with how handsome you are while youre talking

Shit, how did you delete sent messages on here? I couldn't believe I'd just said that. Maybe Lexi was rubbing off on me. Or maybe it was true and online interaction was easier. It was a moment before he wrote back.

Leon: But you should be in class at the moment, right?

Me: heehee, now you sound like a dad

Me: besides, youre at work too, right daddy?

Leon: Haha fair enough

Me: im a senior, so attending classes are just a formality at this point

Me: meaning i can take all the naughty photos you want~ ;)

What was I doing?! An hour ago, I'd have never imagined I could say these things to him. Yet with the security of relative anonymity -- did pretending to be somebody else count? -- it seemed I was comfortable enough to let my inner desires out. Or maybe I was just getting swept up in the current of what was happening. It was becoming hard to tell.

Leon: That's a tempting offer, though I probably shouldn't

Me: dont you like what you see?

Leon: I do, it's just that

Leon: Never mind what I said. I'd very much like whatever you send

Me: good to know ;)

He was probably hesitating because of mom again, but then decided to push forward with whatever direction he was going now. That was my guess, anyway. I'd have to ask Lexi about it later. But the adrenaline rush from actually flirting with my dad... It was something I could get used to.

--

"You ran off on me," Lexi said in mock accusation. "One must wonder why."

"I was... busy," I managed as she walked into my house. "Did you park next door again?"

"Mhm. Coco's very generous." She let me lead her to my room and waited until the door was closed before sitting at my desk. I plopped myself down on my bed, and she eyed the burner phone that was within reach next to me. "Busy with what? Sexting your dad?"

"I--"

"Have you sent the second nude yet?"

I swallowed. "Yeah."

We stared at each other, and then she shook her head as a prompt. "And...?"

"And we've been talking..."

She grinned and crossed her legs. "Do tell."

"What is the next step, anyway?" I interrupted, diverting her attention. Luckily she obliged. Not so luckily, the answer was a real zinger.

"Arranging a meetup, of course," she replied, as if this didn't just upend everything. "Isn't that what normally happens on a dating app?"

"What-- Hold on. Are you fucking crazy?" I demanded. "A meetup?! You or me?"

She snorted. "You. Obviously you."

"Lexi, I can't." My hands were shaking. "It's too soon. I don't think I'm ready. I don't even know if I want to take that step."

She chuckled. "It's not all that. Not yet, anyway."

"What do you mean 'not yet?'"

"I mean, you should probably decide what you actually want if you're second-guessing if you 'want to take that step' or not. If not, then we're just wasting our time here." She leaned toward me, her expression slightly annoyed. "C'mon girl, are you in or out?"

"I--" I stammered. Of course I wanted to take that step. I was just scared, and apparently I was putting all my trust in Lexi. It felt dangerous, and now I was having doubts. If her plan didn't work, what state would my relationship with dad be left in?

You can't let yourself be paralyzed by fear. Nobody is going to fulfill your dreams for you, Cherish.

Why did Ms. Hammond's words keep coming back to me? Because I knew they were true. Even with all the help Lexi was giving me, I had to reach out and seize what I wanted. She couldn't force me and my dad together. I knew now that my dad was ready to try moving on from mom, and if it wasn't with me, it'd be with somebody else. I could watch him from afar, wondering what could have been. Or I could risk alienating him by plunging us both into sin.

He'd forgive me. He'd understand.

"I'm in."

Lexi nodded, slowly and approvingly. She leaned back in her seat and propped one of her arms up, fingers picking at each other. "Then the plan is a meetup for tomorrow. The two of you will rendezvous at a hotel room. You'll be there first, to prepare. Gotta cover your top half, so he can't tell who you are."

I gulped. "And my bottom half...?"

She smirked. "Have you ever been spanked before?"

I was mortified. "Hell no! Why would I want that?!"

"You do know the difference between spanking and beating, right?" she asked with a raised eyebrow. I floundered and she sighed, shaking her head admonishingly. "Don't worry, your dad will. Relax, you'll enjoy it." We heard the front door open and close, and she grinned a fox's grin. "Time to send that last nude."

Taking the phone in her hands, she opened ComeDaddy and scanned the earlier messages.

"Hey, that's private!" I protested. Lexi hadn't been around to advise what to say since lunch, and I felt protective of what my dad and I had said to each other.

"I have to make sure you two are on the right track here," she explained. "Don't worry, it won't be for much longer, I promise you that." After reading her fill, she nodded approvingly, then sent the last nude of me with my nipples exposed.

Me: a little treat for tonight~

Me: lmk after youre done "using" it, i wanna propose something ;D

"Now," she said after sending the nude and messages, tilting her head toward my bedroom door. "Dinner time. Get going."

Nodding dubiously, I went out to greet my dad. He was still in the living room, looking down at his phone and panting slightly. I felt a slight thrill at the thought of him drooling over my body.

"Hi dad," I called out, and he quickly put his phone away, looking guilty as hell. Was that what kids looked like when they were caught watching porn? It was actually pretty funny.

"Hey princess," he managed. "It's good to see you. You doing okay?"

"Yeah, I'm fine," I replied. He'd been walking on eggshells around me since my outburst on Wednesday, and I felt bad that he thought he couldn't talk to me. It didn't help that Lexi had been over yesterday, enacting her plan for me, which ended up making him think I wasn't talking to him anymore. Dinner together would be nice, and hopefully clear the air a bit. "Hungry?"

"Famished." I caught his eyes doing a once over down my body, and when he swallowed I doubted he was thinking about food. Damn, maybe Lexi knew what she was doing after all. She'd timed the final, most revealing nude to be viewed just before he interacted with me.

He went to get changed while I set the table and heated the food up. Our conversation was casual, and I had to occasionally tear my mind away from what we'd messaged each other on ComeDaddy, reminding myself that in his mind I shouldn't have been privy to those texts. I actually caught him staring at my chest a couple of times, and when his eyes flickered up to meet mine, he looked away hastily while I smiled to myself.

Afterwards, I returned to my room to find Lexi gone, presumably having made her exit out my window like yesterday. I heard dad go into his office and close the door, and pulled out my own phone to view the feed from the hidden camera. Unfortunately it didn't have audio, and I crept out into the hallway and stopped outside his office. On my phone's screen, I could see him at his desk, pulling his magnificent cock out and beginning to masturbate to something on his phone. The last nude, my pale nipples visible for his viewing pleasure.

And pleasure himself he did, stroking his length vigorously to who he thought was Lexi. I slipped my hand into my panties, fingers moist as they rubbed my clit. Outside the door, I could hear dad groaning as he got close, and I finally overheard what would mirror the events on Monday.

"Cherry..."