Buttholing Ch. 01

This story is posted on the Literotica website. Do not repost anywhere else without the author's consent. For fans of my stories, they know what kinds of things to expect. This story deals with similar themes as the stories by wannabeboytoy, seducedHylas, and Dark Betrayal, namely cheating, betrayal, and heartbreak. If stuff like that isn't your cup of tea, then you probably shouldn't bother reading it. I do not condone any of these actions in real life. This is just a story. Enjoy.

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(Jim)

"Have you ever heard of 'Buttholing'?" my wife asked me.

"Excuse me?" I replied, nearly choking on my water.

"Buttholing?" Charlotte repeated, as if this was something I should easily understand. "I heard some people mentioning it online on, uh, Facebook, on a parent group. They were warning us all about it. They were saying that it's some weird thing that teenagers are doing now. And, we should, well, be aware of it," she explained as we stood in the kitchen, catching up on our separate days.

"I feel like I don't want to know what it is," I replied, not wanting to grant purchase in my mind about the depths of depravity teenagers these days could come up with.

"Maybe we should ask Sabrina about it?" Charlotte asked, referring to our daughter. I shrugged my shoulders, not really interested in pursuing this line of conversation any further.

"Ask me what?" Sabrina asked, padding into the kitchen.

Sabrina was our pride and joy. Our 18-year-old daughter. I felt like we had done well with her, considering we were young and unready when we had her. But she had turned out great. She was smart and witty and very beautiful. Plus, she just had a good head on her shoulders, which was the thing I was most proud of with her. She had, for the most part, never really acted out or rebelled. Of course, there were arguments here and there, but nothing too crazy. We had always maintained a strong and healthy relationship as she grew up, even during her teenage years, so we were able to talk with her openly and honestly about most things. This gave us a relationship where we never really had to discipline her as she seemed to stay in line without us having to put our foot down. Being open and honest with her seemed to be the best policy. With that being said, I wasn't exactly sure I wanted to bring her into this conversation.

She had stepped into the kitchen barefoot, her feet sticking to the linoleum as she moved to the fridge. She was home from school and wasn't going out again, so she was dressed down, clad in a simple tight t-shirt with some band logo on the front, straining to contain her large breasts. As her father, I wasn't always pumped to see her dressed in form-fitting clothing like this. I mean, she was a woman, a young woman, but a woman nonetheless, so she was allowed to do her own thing. I get that, but uh... her breasts were very large. Much larger than her mother's, rounder and perkier too, so they were very attention grabbing, and seeing the way guys would stare at her made me uncomfortable. I don't know where she got them, as her mother had a petite chest, and Sabrina's were the farthest thing from petite. But uh... anyway, I'll move on. So, despite her obvious beauty, she was a smart, well-adjusted girl, so she could handle herself just fine. To complete her relaxed ensemble, her lower half was clad in a pair of loose, thin, stylish sweats. Her dark brunette hair was tied up in a comfortable ponytail, and her pretty face was curious as she looked at us.

"Uh..." I began, looking towards Charlotte, curious if she was willing to have this conversation with our daughter.

"Have you ever heard of 'Buttholing'?" Charlotte asked Sabrina as she moved towards the fridge, getting right to the point. Sabrina paused as she stopped near the door of the refrigerator, and a slight blush went through her. Her eyes widened slightly as she looked at us, a small smile crossing her lips.

"I'm surprised it's taken this long for parents to start hearing about that," she replied, pulling out a carton of OJ. "Now it's not gonna be cool anymore..." she added with a smile.

"So you know?" Charlotte asked. Sabrina looked between us, trying to discern if we were upset with her for knowing this. She turned to look at us, appraising us for a moment.

"Why do you know?" Sabrina replied, standing in place, not wanting to give up information unnecessarily.

"Well, I heard someone mention it online, some parents, and they were warning us about this thing called 'Buttholing', and I'd never heard about it before," Charlotte answered.

"Trust me, guys, we should just stop now. You don't really want to know. Trust me, let's just not go down this road," Sabrina replied with a laugh, filling a glass with Orange Juice.

"Is this something we should know?" my wife asked. Sabrina rolled her eyes.

"It's a... teenager... thing. You don't NEED to know," Sabrina deferred again.

"Well, now I'm curious. And if you don't tell me, I'm just gonna look it up and find out what it is, so you could save me the time and let me know now. I'm just gonna get more nosy about it." Charlotte replied, knowing how to get information out of our daughter.

"Fine!" Sabrina relented with a smirk, stepping towards the island counter, setting her glass down. "But if I explain it to you, do I get Diplomatic Immunity?" she asked. Diplomatic Immunity, in our family's case, was a thing we came up with in dealing with Sabrina that allowed us to ask her questions and have her answer honestly, without fear of her getting in trouble or us probing too deeply into her business.

"Sure," I replied. She paused for a moment, verifying our assertion, before finally replying.

"Okay... what do you want to know?" she said, glancing between us.

"So, tell me, dear..." Charlotte began with an inquisitive smile. "What is 'Buttholing'?" Sabrina looked between us, slightly nervous to start discussing this topic with her parents. We looked at her, conveying that it was okay to speak openly about this to us. She paused before speaking up.

"Buttholing is..." she began, looking up, searching for the right words. "Buttholing is that thing when a girl sends a guy a picture of her asshole, and..."

"What??" I interrupted, stunned.

"You're kidding!" Charlotte stated.

"Well, let me finish. If you let me finish, then it will all make sense..." Sabrina stated, but Charlotte was undeterred.

"Why would they do that?" Charlotte interrupted, turning her nose up.

"Because it drives the boys crazy!" Sabrina stated with a laugh. "I mean, just, like, most of the girls in school will show off their tits at a moment's notice, and that just isn't enough for most guys anymore. And, like, guys can go online and see girls doing literally everything, so, like, it really takes something special to get a guy's attention now. They expect more from us. A guy can turn a corner and have some girl flash her tits at him, but when that cute girl from Calculus sends you a picture of herself, spreading her butt-cheeks apart and showing off her tight asshole, well... that makes a guy stop in his tracks. It makes the guy realize that the nice, sweet, pretty girl in your class is very, very, uh... available... for some pretty serious stuff."

We weren't typically opposed to our daughter cursing in front of us, but even with her restraining herself in her description, hearing these words pass through my daughter's lips, and learning that she was well-versed in stuff like this, was definitely jarring.

"But why would any guy want to see a girl's butthole? That's just nasty!" My wife asked.

"Mom, you clearly don't understand boys," Sabrina said knowingly, glancing my way for a moment, slightly blushing at this conversation, but still smirking in amusement. "They only want the NASTY girls! The girls who would do anything! And besides... we're girls. Girls' buttholes are nice and clean and pretty and perfect. You might think it's weird, but guys LOVE it..."

"So, this is a thing, now?" I asked, entering the conversation, still not really knowing how I felt about this whole thing. "Girls just sending pictures of their buttholes to guys?"

"I mean, yeah, pretty much," Sabrina said with a shrug. "It's sort of like a thing that a girl does to let a boy knows she's serious about him. If she wants to take things from flirting to... something more... to like, full-on..." she paused, before holding her fingers in a circle and inserting her pointer finger in-and-out, simulating sex.

"Does the guy have to do anything in this scenario, or do the girls do all the work?" Charlotte asked, sounding almost weirdly offended by the perceived imbalance of the situation.

"Well, yeah, I mean, the guys have to send us something in return. It's usually a trade. Like, 'Oh, here you go, here's a picture of my butthole, oh, what's that, a picture of your junk? Oh, thanks!'" my daughter stated.

Me and my wife glanced at each other, stunned by Sabrina's words and stunned at how knowledgeable she was about the subject. The same question rose to both of our minds.

"You've never, uh..." Charlotte began. She let that hang for a moment till Sabrina understood.

"Diplomatic Immunity..." my daughter sang, smiling vaguely, not giving us a hint. I didn't know what to make about this, and her hole, uh... I mean... whole attitude about this. I wasn't sure if she was lying or not, but honestly, I really didn't want to know. "I will say that a lot of my friends have though. You know Cecilia? She's, like, the queen of it. I've seen some of the pictures she's taken. They're, like, artistic... almost."

"So..." Charlotte began, still in disbelief. "You've got all these girls showing off their buttholes to the guys. There's pictures being traded off throughout the school of all these girls exposed like this, and this doesn't bother you?"

"Eh," Sabrina shrugged. "I'm just like... so what? It's not hurting anyone. And it's not like you can see any faces in the pictures, at least if their doing it right. And besides, if anything, it's about us girls taking the power, isn't it? I mean, it's us girls making the call, dictating who we want, putting the boys back on their heels. I think that's kinda cool, you know?" she paused for a moment, speaking of Buttholing as if it was almost an act of female empowerment. "To me, it's all good, clean fun, so I don't really see the problem. The girls are pretty good at it, too. Like Cecilia, she puts all these filters and exposures on her pictures. She's, like, the Mona Lisa of taking pictures of her butthole."

"Uh..." Charlotte paused, shocked into silence by this.

"It'd be Da Vinci..." I couldn't help but interject into the silence.

"What?" Sabrina replied.

"She'd be the Da Vinci of taking pictures of her butthole. Mona Lisa is the picture herself. Da Vinci was the painter," I pointed out. Charlotte looked at me, shaking her head, annoyed that this was what made me interject, and Sabrina looked at me blankly.

"Whatever..." Sabrina said with a shrug, rolling her eyes, taking a swig of her OJ.

"I just don't understand this at all," Charlotte said, turning away to stash some dishes.

"Of course, you wouldn't. I mean, I understand it, sure, but I can't explain why it works either," Sabrina said. "I can't explain what boys like, but like I said, it drives guys CRAZY. You have no idea! When they see what, uh... when they see what they see, they get so, uh... excited! I've seen it happen. I've seen how it changes them. They go from uninterested to, uh, very interested, just like that. When they see those pictures, they just want to sink their..."

"Alright! I don't want to hear any more about this," I announced, stepping back to help my wife.

"Well, I know we've agreed that you don't have to say anything," Charlotte began, "But if I ever find out..."

"You won't," Sabrina replied with a coy smile, her answer vague. Was she saying she would never do it, or that she would never let her mother find out?

"I don't get the appeal at all," I said, shaking my head, more amused than upset.

"Well..." Sabrina said, setting her glass down in the sink. "You never know, Dad. You should hear some of the things some of my friends have said about you. Don't be surprised if some of these girls are Buttholing you sometime soon..." she teased, giving me a wry smile, gazing at me conspiratorially as she began sashaying out of the room. I rolled my eyes and glanced at my wife.

"I can't believe this. I mean, kids these days..." my wife opined, shaking her head. "When we were young, we had to work up the nerve to call up boys at their house. Now, you got girls proudly sending out pictures of their assholes? What the hell? I hope Sabrina's not doing this..."

"It's probably a fad," I explained. "And don't worry... Sabrina's a smart one. She'll be fine." I assured Charlotte, kissing the back of her head.

Charlotte was clearly a bit bothered by this whole thing for the rest of the night. I knew her, and I knew how she fixated on things, so I knew this would be something I'd be hearing more about from her. If I told her this morning that she'd be upset about the welfare of my daughter and her female classmates' buttholes, she would have laughed. I would have too. And even after hearing this whole crazy story, I honestly wasn't too bothered. That being said, while I wasn't the type to let things weigh me down, I had to admit this odd conversation had stuck with me.

It was so strange. I mean, I understand girls sending pictures of their breasts, or their asses, but their assholes? Was that really what guys were into these days? Even though I was a relatively young father at 43, I had never felt this old compared to the young adults of today. It didn't feel like I had anything in common with the guys of today if this was what they were actually into.

The rest of the night went pretty normal. As night set in, Charlotte went to bed before I did, as she tended to do, and I sat back and relaxed, watching a baseball game. Sabrina was usually a night owl, like I was, and I could still hear the TV from her room. I could also hear her moving around, and would occasionally hear her talking excitedly to her friends on her phone. But Sabrina was gonna outlast me this night, it would seem. The game I was watching was about over and I was about to head up to bed, only to stop when my phone dinged from the coffee table. Not thinking twice, I reached forward and grabbed my phone, lazily unlocking it to see the text I had just been sent.

When I saw what I'd just been sent, my eyes widened, and a jolt of shock coursed through my body.

I'd been texted a picture, and I was staring right at it. And what I'd been sent, to put it bluntly, was an ass. A young woman's bare-naked, juicy, round ass, one of the firm cheeks being pulled apart by her delicate hand as she reached back to take the picture with the other. The young woman was kneeling on her bed, face down, ass up, brazenly exposing herself for the camera.

In my stunned state, I couldn't help but examine what I was seeing, in great detail. This young woman... she was so exposed... so raw. And so bold as well, being so willing to send a picture like this to another person. I studied what I was seeing, the smooth, round perfect cheeks. The full length of her exposed crack, granting a view that few should get to see, and I had somehow been deemed worthy. Between her legs were the plump, bare, puffy lips of her pussy, a bead of glistening moisture dripping from it. Taking this picture made her very excited.

But the main event was front and center in the picture. Nestled deep in her ass-crack. The one thing she clearly wanted to show off, something even more forbidden than her tight, wet pussy. Something she was brazenly exposing to the camera.

Her clean, bare asshole.

I wasn't a big porn guy, and I didn't particularly have an anal fetish, so I honestly didn't know if I had ever seen a woman exposed like this. I had never seen a girl so willingly and boldly exposing their asshole for someone else's pleasure. And, to be honest, I didn't find it quite as unpleasant as I thought I would. Like I said, her asshole was bare and clean, allowing me to appreciate every little detail of the tight puckered hole. The lines around it, leading towards the center, to the hole itself, that infinitely tight hole. It was the center of the universe, drawing all attention towards it, pulling the surrounding flesh towards it into one tight knot. Begging to be untied. Begging to be broken in. Like the Gordian knot, asking to be pierced by one worthy of doing so.

I suddenly realized what I was doing. I was staring at a woman's asshole. A woman I didn't recognize. I studied the rest of the picture, searching for clues to her identity. The only thing I could see of her was the back of her head. Her smooth brown hair was tied up in a loose ponytail, a manner that seemed familiar, but I couldn't quite place it. I looked at her surroundings, and it was then, seeing the cream-colored carpet and the light pink bedspread, that a lead weight fell in my stomach. It was familiar, and I was starting to place it.

Suddenly feeling stupid, I thought of an easy way to discern her identity. I tapped the screen of my phone, revealing who had sent me the picture, even though I was beginning to suspect the truth. And when I saw her identity, it confirmed my worst fears.

It was Sabrina.

Sabrina had sent me this picture. Sabrina had sent me a naked picture of herself. Sabrina... my daughter! Naked! Spreading her asshole for the camera! To me! Holy shit!

I just got Buttholed by my daughter!

Oh my God! Oh my God! Oh my God! My daughter just sent me a picture of her butthole! What the fuck! What the actual living fuck was going on!? What was she doing? Why!?

My first instinct was to march up to her room and demand her ass... I mean... answers from her. An explanation. Was this some sick joke or something? A prank. Looking at the picture again, I confirmed it was actually her. Now that I knew, it was obvious. It wasn't some other girl. It was the real deal. A nude picture of my daughter that she herself had sent to me. I needed an explanation. I needed to know what the fuck was going on. I stood and made to move, only to stop in my tracks as I had a revelation. As I realized my current state, I looked down towards my crotch.

My cock was stiff as a brick, and it was bulging out against my pants very obviously.

Instinctively, I sat back down, trying to hide my erection, even though no one was in view. Woah... where had this come from? What the fuck? Yeah, the image was raw and brazenly sexual, for sure, and I suppose on a primal level, it affected me. Especially because this was something I hadn't really encountered before. But... this was my daughter. My daughter's naked asshole! I probably got stiff before I realized it was her, but Jesus... my cock wasn't exactly going down since learning the truth. It almost felt harder upon this twisted revelation. It had a mind of its own, clearly, because I knew better. This was my daughter. I knew that. But my cock wanted nothing more at this moment than to be free from within my pants. What was wrong with me?

I tried to clear my head, but the image was already seared into my memory forever. Why had she done this? Was it a mistake? Was this meant for someone else? Maybe instead of Dad, she meant to send it to, like, Dave, or something? Who is Dave? You know what, fuck that guy! I'll beat his face in for having pictures like this of my daughter!

Okay, okay, calm down. Don't jump to conclusions. This had to be a misunderstanding. A mistake. I glanced at the cursed photo again, just in time for another ping from a text. And this one erased any doubts.

'What do you think, Dad?' Sabrina asked via text.