Popping Her Cherry

All characters are above the age of 18 unless otherwise specified.

This story was originally written as part of a different story already published before I cut it and reworked it as a standalone; you can still think of it as a spiritual prequel if you desire.

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"What should we watch?" Ashlie asked, plopping herself down on the other side of the couch from me.

I took a brief glance at my watch; 8:32.

"Nothing too long, it's already kinda late."

"Are you kidding me?" she asked, stretching her long legs out and giving me a gentle shove on the thigh with her foot. "The night's just beginning."

I chuckled. "Maybe when you're 19. Come back when you're 47 and try telling me that."

Ashlie curled herself back up on the couch, pulling her knees up to her chest. She had the TV remote in-hand and was flipping through Netflix or HBO Max or something.

"So no Endgame then?"

"How long is it?"

Ashlie sighed. "Three hours. But you still haven't seen it! It's been years. You haaave to watch it," she pleaded.

"Uh-uh," I replied. "Put on a TV show. Or a movie's fine if it's like an hour and a half. I'm gonna be tired soon."

"Ugggh," Ashlie groaned. "You're fucking boring!" She feebly tossed one of the throw pillows at me, sailing it two feet over my head. Another reminder why she did cheer and gymnastics, and not softball.

"Hey you need to respect your elders. Besides, I'm not even a quintagenarian, you're gonna be in my seat sooner than you realize."

"I don't even know what the fuck that word means," she replied.

I pushed myself up from the couch and let out an exaggerated sigh. "You need to read more books," I said as I made my way to the kitchen from our living room. "Find something to watch, I'm grabbing a glass of wine."

"Wine, dad, really?" Ashlie asked. I looked back and saw her head peeking over the back of the couch, a very judgmental look adorning her face.

"It's good for your heart," I reasoned.

"Well can you get me a glass too?" she called back, a hint of both desire and insecurity in her voice, unsure if I would oblige her request. We hadn't raised our daughter to be a prude or anything; we certainly didn't encourage a party lifestyle but we also wanted to make sure she wasn't coddled and was prepared for the inevitable time when parties would happen and guys would be flinging themselves at her. Ahh, the struggles of having an attractive, popular daughter.

Still, this was the first time our baby girl had ever actually asked to drink, at least at home. And now I had a big decision to make. Of course it was just me at home, I couldn't defer to my wife.

"Uhh, sure," I answered, forcing myself to go with my gut reaction. I did always try to be the cool parent after all. "Red okay?"

"Yeah, whatever you're having," she responded.

"Sounds good," I yelled back from the kitchen as I poured two glasses of Cabernet. I added a little bit of water into Ashlie's glass, just to make the taste a little more palatable; it's the way her mother took her wine (except with sparkling water).

"Any reason for the sudden change?" I asked as I made my way back from the kitchen.

"What do you mean?" Ashlie responded, taking her glass.

"You've never asked for a drink before."

"Well I'm leaving for college soon. You guys already know I'm not gonna be a big drinker or anything, but I want to have at least a little experience. Just so I know my limits better."

That sounded like reasonable enough justification for me. I was far more of an alcoholic at her age, so I wouldn't complain about just a baby step.

Ashlie took a sip of her wine. Her face twisted up initially and she forced herself to swallow it. I smiled, remembering the days before I acquired the taste for wine.

"Did you find us something to watch?" I broached, changing the subject.

"Yes!" she said enthusiastically. "It's a rom-com, and you're going to hate it!"

"Ahh fuck," I grumbled. "Seriously?"

Ashlie giggled, taking joy in my displeasure. "It's only an hour and twenty minutes, and that's all you said!"

"Fine!" I begrudgingly relented. I took a long sip of my wine. I was a little surprised, it actually tasted a little sharper than usual. I typically preferred my wine smoother and less acidic.

Ashlie pressed play on the movie, and the production logos started to play. I stood up, drawing her attention to me.

"What're you doing? I just started it."

"I need something a little different," I answered.

"Well can you leave your glass here then? I'll finish it."

"Uhh, sure," I said, seeing no harm in it. That would actually be a good transition from her anyway, going from the watered-down version to the standard Cab.

I returned to the kitchen and poured myself a glass of Bulleit, the one type of liquor my wife never liked to share, making it my own special treat. I poured two fingers; it had been a long week.

"Not beer?" Ashlie inquired when I came back. The opening credits had just started to play.

"Nope. One of my favorite life lessons: beer before liquor, never been sicker; liquor before beer, in the clear."

"So bourbon now lets you maybe transition to beer later but not the other way?"

"Exactly."

"Good to know," she said and took another sip of her wine. I noticed that one of the glasses was already empty, back on the coffee table in front of the touch. I raised my eyebrow a little, knowing she was on her second glass.

The movie had started. It was some paint-by-numbers thing from the 2000's with terrible acting that I vaguely remembered having seen on a plane a long time ago. Another one of those "unreasonably attractive people doing scandalous things to each other repeatedly" stories.

"I've definitely seen this before," I said a little bit in, once parts of the plot I remembered re-assured me.

"Really? When? Not the type of movie I'd have pegged you for watching."

"Uhh it was on a flight a long time ago. I want to say you were 5 or 6 and I was going out to visit Uncle Steve in Delaware."

"Wait Steve used to live in Delaware?" Ashlie asked.

"Yeah for a few years, his company's headquarters moved there."

"Why? What's in fucking Delaware? I don't think I could tell you a single thing about that state," she said as she rose from the couch. "Want a top-up?"

I looked down at my nearly-empty glass. "Sure, why not? It's a weekend night."

Ashlie went back to the kitchen, and I focused on the movie. It was considerably less tolerable without a glass of alcohol in hand. At least the lead actress was pretty.

Speaking of, Ashlie returned just in time to be my salvation.

"I wasn't sure exactly how much to pour you, so...." she admitted as she handed me my glass.

"Holy fuck," I exclaimed, as she handed me back a very full tumbler. "That is wayyy too much."

"Oh, well it'll be fine," she said dismissively, lying back down on the couch. "Who cares? It's a Friday night, Mom's away for the weekend." She stretched her legs out and let her feet rest in my lap.

"I mean you're right, but I don't want you thinking your dad's an alcoholic."

"I won't," she said, smiling back at me before taking another sip of her own larger wine glass, filled almost to the brim. Those were the pours her mom did after a long day; we called them "Mom pours" specifically for that. Ashlie was now carrying on the tradition evidently.

The movie continued playing, and I found myself in a bit of trance. My eyes were on the tv but I wasn't really paying attention to anything happening on it. I was mindlessly sipping my bourbon while my mind was wandering to just about anything else: when the next car payment was due, how the Bears were looking in training camp, what I should make us for dinner tomorrow with my wife, the real cook, out of town.

Movement on the couch next to me was enough to finally catch my attention. Ashlie had grabbed the blanket off the back of the couch and had spread it open so she could lie all the way underneath it, covering up my lap in the process. As she squirmed to get comfortable under the blanket, her feet pressed into my thighs, and the balls of her feet gently nudged against my dick.

I felt a small stir in my cock, just the littlest bit of attention enough to start turning me on, even if unintentional. After having been married for 20 years, the sex started to get a little more stale and far less frequent, so it felt good getting any amount of stimulation. And even if it was from my daughter, it was totally harmless and unintentional, so I didn't necessarily have to feel bad about it, even if a little weirded out.

My bourbon was almost half empty (half full? my wife always said I should be more optimistic), and I could feel a little buzz coming on. Ashlie was almost finished with her glass, and I could already see a rosy glow building in her cheeks. It brought me back to the first time I had ever gotten drunk. It was at a friend's house in 11th grade, and I puked my guts out after drinking too much vodka swiped from his parent's liquor cabinet. Ashlie was right that she needed to get a feel for her tolerance and know what it felt like, and if I was here to supervise her, that was the safest environment for her anyways.

The music on the TV began to swell. Between all the shitty acting and dialogue, the score was actually pretty solid. I doubted they got Hans Zimmer to do some terrible rom-com, but it didn't sound too far off in quality (except for the lack of deafening brass).

I started paying attention again as the loud music signaled the lead-in to a dramatic scene. A very handsome man who I'm pretty sure was the main guy character's best friend, was dramatically professing his love for the main female character in public, saying how much he adored her and how alive she made him feel (little did she know he was also trying to fuck her sister, but I knew that she would find out in about thirty minutes).

"Is that how you and Mom first got together?" Ashlie asked.

I looked over at her and chuckled. "No," I responded with a grin. "We were never that spontaneous."

"Really? I feel like that's the key to maintaining a relationship for so long."

"Well yeah it's important," I mused, taking another small sip of Bulleit. "And we were more spontaneous when we were younger. Just not quite like that."

"What do you mean?" Ashlie pressed the subject.

"You really want to psychoanalyze our relationship three glasses deep?" I asked.

Ashlie smiled and let out a loud, decidedly un-ladylike burp on cue. "Yeah, that's the perfect time."

I couldn't suppress a laugh. "Alrighty then. Your mother and I have always been best friends. That's what's helped us stay together for so long, even when that initial burning passion dies down."

"I think I know what you mean," Ashlie said. "But wouldn't you want to find someone where that passion doesn't die down?"

"I mean, in theory of course, but that's like finding the end of a rainbow, or a woman named Karen who doesn't want to speak to the manager. That kind of thing just doesn't exist."

"So you and Mom don't really have a passion for each other anymore?"

"That's not really what I meant, I think you're reading into it too much."

"I just meant like, it's not the same as at the beginning?"

"Well it's been over 20 years, people change, and the situations have changed a lot too obviously," I said with a laugh, trying to lighten the mood a little.

"You mean me?" Ashlie said, bringing her foot up and giving me a light jesting shove in the gut. "You're trying to say I'm the reason you and Mom aren't as burningly passionate and spontaneous as you used to be?"

"Of course not you little shit, and you know it. You're the greatest thing that could have ever happened to us."

"Good, and don't you forget that."

"Not a day goes by when I could."

I took another sip of my drink, and we sat in silence for a few seconds.

"I bet it's the sex."

It took me a second to process what Ashlie had just said.

"I'm sorry, what?"

"Fucking the same person for 20 years. I bet that's why the luster is gone."

"Ashlie!"

"Tell me I'm wrong, you know I'm not," she proudly boasted.

"I think you've had too much to drink," I responded, trying to avoid playing whatever game it was she was playing.

"Silence speaks volumes," she laughed. "And to the contrary, I don't think enough has been had!"

Ashlie tore the blanket off of herself and got up off the couch towards the kitchen. She had to steady herself for support when she first stood up.

"I think that's just about enough young lady, last glass," I said, still trying to maintain some semblance of control as a dad. Ashlie's words had disarmed me a little. She was right. And she knew it.

"Dont get your fucking panties in a wad, you prude. Mom's not home to get you in trouble," she shouted from the kitchen.

"I'm still your father," I shouted back.

"Then punish me!" Ashlie jested as she walked back into the room with her glass full. Again it was a very heavy pour, almost two glasses worth.

In her other hand was a can of Miller Lite, my cheap and reliable old friend. She slid it across the coffee table towards my end as she plopped back down on the couch and got under the covers again.

"I haven't even finished this yet," I pointed out, raising my now-nearly empty tumbler.

"Thinking ahead. I don't want to get up again," she reasoned.

"Well, can't say I didn't raise you to think strategically," I joked.

"Nope."

Ashlie was adjusting herself a little under the blanket, and her feet were moving around in my lap again. The ball of her foot kept brushing against my penis, and at one point she ran her left foot along the length of my dick while she was stretching out.

I could feel my cock twitch and harden just a little as her feet came to rest on top of my crotch. It was tantalizing almost, especially with what we'd been talking about earlier. There was no way she knew what she was doing, but it was still a tease.

With her feet resting right on top of my dick, I tried to focus on blocking out the sensations from there, trying not to get any harder at all in case she would notice. Sadly this had the opposite effect; thinking about my erection only made it grow worse. I prayed Ashlie wouldn't notice anything. Luckily she seemed to be concentrated on the movie for now.

I followed her lead, turning back to the movie, trying to take my mind off of the semi I was attempting not to sport.

We sat in silence for a little bit. I got a text from one of my coworkers, the light on my phone suddenly illuminating the room otherwise devoid of light (besides the TV).

"Whose that?" Ashlie inquired, slurring her words a little.

"Work," I responded as I grabbed my phone and looked at the text.

"Well tell them to fuck off, it's a weekend."

"I can't sweetie," I laughed. "Besides it's nothing urgent, I can deal with it in the morning."

"Good, cus fuck those guys. It's just you and me right now."

"You'll be singing a different tune when you have a job."

"Nope!" she proudly exclaimed, and flashed me a big smile. I grinned and shook my head. In some ways my daughter was very mature, but right now she certainly was not showing that.

"Watch the movie anyway, we're getting to an important part," Ashlie instructed.

"How do you know, I thought you hadn't seen this before."

"I haven't, but I looked up the plot," she revealed.

"Spoilers."

"You've seen it too!" she pointed out. "Now shush."

I obliged her, returning to silently sipping my drink, downing the last little bit.

On screen, a kid was climbing up the outside trellis of a house and sneaking in through a window. It was a pretty typical scene of high school kids, he was clandestinely meeting his girlfriend. It was the main character's little sister if I remembered correctly, home on break from college and finding her first summer romance. And this was the main character's love interest's brother, who also loved the main character. So a lot of intersecting drama.

The two kids (probably supposed to be 19 yet played by 27-year-old actors, but still kids to me) started talking. The guy climbed onto the girl's bed and lay next to her while the girl's tv played (always a good idea to help hide any untoward sounds that might alert parents). He was trying to make some moves on her, but she seemed unsure of whether or not she wanted to do it, explaining that it was because she was still a virgin.

Ashlie sat up on the couch, taking a long gulp of her wine and finishing off the glass. She cuddled up right next to me, bringing her knees to her chest.

"Dad I have a serious question for you."

Based on how the rest of the night had gone I wasn't entirely certain I wanted to hear it, but I wasn't going to stop her.

"Were you nervous when you lost your virginity?"

I was a little taken aback by her question, especially because Ashlie never really had been a super wild or open kid. We'd had the talk obviously but hadn't really discussed sex that much at all, before tonight at least.

"Oof, that's a tough question. But sure I was nervous a little, I didn't want to fuck anything up or make an ass out of myself."

"Did you?"

"Well I'd like to think not," I joked. "Really if you find the right person, someone you're comfortable with, that makes the entire process much better and more enjoyable, when you know that you're not going to be judging each other or holding unrealistic standards or something."

"Yeah that makes sense," Ashlie said. She leaned her head against my shoulder, and held my left hand between her own. "Was yours with Mom?"

"Your mom and I started dating when we were 24 sweetie, I'd certainly hope my game was better than that," I quipped.

"Who was it with then?"

I thought back to my first time; it felt like so long ago, probably because it was. It brought back a lot of good memories though, from a less stressful and easier time.

"It was with my first girlfriend in high school, a girl named Allison. I was a junior, she was a senior, and we'd been dating for about six months."

"Oh, nice," Ashlie said, a little disappointed almost.

"What's going on baby, why are you asking all these questions now?"

"Oh, nothing, don't worry about it," she said, with her tone giving the opposite impression of her words.

"Ashlie I'm your dad, I've lived with you for 19 years now. I can tell when something's up."

"Okay, but you promise not to tell Mom that we talked about this?"

"Yeah of course. Tonight can be our little secret."

"Good. I'm just, like, a little stressed, and depressed, cus I'm going off to college soon, and, well..." she paused for a few seconds, collecting her thoughts. "I'm still a virgin."

I waited a little, wanting to see if she was going to elaborate. "Is that all you're worried about sweetie?"

"Well yeah," she answered. "Like all of my friends already lost theirs, and I just don't want to mess anything up when I'm away at school, you know?"

"Oh baby, you don't have anything to worry about." I wrapped my left arm around my daughter, pulling her into a snug embrace. "Plenty of people don't have their first time until they're older, and it's really not that big of a deal. Trust me. People your age make it a bigger deal than it is."

"Well that's easy for you to say now that you're older, but I'd be doing it with a guy my age so it would be a big deal to him. So that doesn't really help."

"Sweetie it's literally nothing at all. You don't have to be nervous about it, I know you're not going to mess it up or anything, and I trust your judgement in picking a good enough guy that it will be a pleasant experience."

"I guess," she said, not sounding too re-assured. "I just feel like it would be better to get it out of the way with someone I know and am comfortable with."