Buttholing Ch. 01

I was shaken. There was no doubt now. My daughter had deliberately and knowingly sent me, her father, a picture of her naked asshole. Was this some kind of twisted joke? A prank? Or was it something more? During my consternation, Sabrina grew impatient.

'I'm waiting...' she texted.

Waiting for what? A response? How can I possibly respond to this? Then, a memory bubbled to the surface, a memory from our conversation before. She said the protocol was that after the butthole pic was sent, the guy was supposed to respond by sending a picture of his big, hard... no... No! She couldn't possibly... no! She didn't actually expect me to... haha. No, no way! This had to be a joke. A twisted prank! It had to be.

'What are you doing, young lady?' I texted back at her, trying to put on a parental tone, trying to regain order and not give any sign that I had enjoyed this picture. Which I didn't, of course. For a few moments, she had stolen that parental feeling from me by her brazen display, making me think less as a father and more as a man. But I had regained myself quickly. After a few moments of my silence, she replied.

'Mom didn't understand Buttholing, but I thought you would...' she replied. I breathed deep, considering how to respond. 'I could tell. You seemed VERY interested!'

What? What was she talking about? If anything, I had wanted to end that whole conversation from the start! No... stop... I couldn't let her get to me like this. I couldn't let her get me worked up.

'This is very inappropriate, Sabrina,' I replied, again regaining my fatherly tone. 'If this is a joke, then it's not funny.'

'You don't really mind, do you?' she texted back. 'I know you think you're supposed to be all upset, but you can be honest with me.' Part of me wanted to just march up to her room and have this conversation face to face, but with what had just happened, part of me wondered if she would be satisfied with just her face facing me. 'I could tell you were interested. You wanted a sample. So I thought I'd spread my butt cheeks apart and give you a little peek...'

'Sabrina, this is insane! Please tell me this is some sort of joke! A dare or something.' I pleaded with her, looking for an excuse to this crazy behavior.

'Nope! I kinda just really wanted to show you my asshole, Dad. So... what do you think?' she texted back hopefully. I sat back, completely confused and painfully erect. Obviously, I couldn't tell her how I was physically responding. I didn't know what to say at all really. But somehow, she knew exactly what I was going through.

'You get it now, don't you?' she texted. 'Buttholing works, even on real men, not just high school boys. I bet you're SO fucking hard right now...'

'Sabrina!' I texted back, panicking. How could she talk to me like this?

'So, Daddy, fair is fair. I sent you a picture of my asshole, so... you need to respond with a picture of your cock. Thems the rules,' Sabrina stated. I didn't know what to do. Firstly, she never called me 'Daddy', but that was the least of my problems at the moment. Obviously, I couldn't do what she asked. Not a chance. I couldn't even consider that. I just had to ignore my hard prick straining to escape my pants, begging to be exposed in all its throbbing pride and glory, for the photo she wanted. I obviously couldn't do that, but she was undeterred.

'Dick pic pleez!' she texted.

I should march up there and put an end to this. But if I did, if I made this a big thing, and my wife found out, that could permanently damage my relationship with both Sabrina and Charlotte. I had to talk Sabrina down from the ledge. I had to end this insanity quietly. Convince her to write this off as some insane joke and just move on for good, and never speak of this again.

'Sabrina. This is enough!' I warned her. There was a bit of a pause before she responded. 'Please! I'm begging you! Tell me this is just a joke.'

'You're no fun!' she texted back, undeterred. 'It's just a standard dick pic. NBD.'

'I'm your father!' I texted back quickly in response.

'So?' she texted. 'This is downright tame considering some of the things I've seen other girls do.'

I was shaking my head. What was going on here? Had I fallen asleep and entered into an insane dream?

'Besides...' she began. 'Like I said earlier, my friends always have A LOT to say about you. You have no idea how excited they'll be if you give up the goods. I'll share the pics with all my friends. I promise!'

'Sabrina...' I started. 'Go to bed. Sleep this off. Hopefully, you come to your senses in the morning.'

'Same to you...' she replied, undaunted. 'You're in the game now, Dad... whether you like it or not. If you don't play along, I'm gonna give your number to my friends. They've been DYING to get it, Dad. Until you finally send me a nice, juicy dick pic, your phone will be barraged by pics of my friends' assholes.'

She paused between texts, letting this threat hang before continuing.

'They'll keep at it until you can't think straight. Until you have no choice but to rip down your pants and share your Dad-cock with the world! So... enjoy!'

That was where things left off for the night. For a while, I just sat there, not knowing what to think or do. Did that just happen? Did my daughter actually just send me a picture of her asshole? What was this insanity?

My disobedient prick calmed down enough for me to get moving without fear of detection, and it was at this point I shut things down and moved towards my bedroom. As I reached the second floor, I stopped outside of my daughter's closed bedroom door. The light was still on. She was still awake. This room was the source of my current predicament. My current state. I could just go in and confront her now, but I didn't. I moved on towards mine and my wife's room, hoping that maybe, just maybe, this temporary bit of insanity would be forgotten by the morning.

Needless to say, it was a restless night.

*************

My mind was still a bit fraught come morning. Despite knowing better, my cock was still half-stiff with memories of the night before. I was still confused at what had happened, and it didn't feel real. But it was. The picture was still on my phone. I had confirmed it soon after waking up. Sabrina, my daughter, had sent me a picture of her butthole. And she had asked... she had asked me for a picture of my cock in return. Was this some twisted game? Or was this the first step to something more? No... no... couldn't be. Not her. Not my daughter. Not my Sabrina.

My mind was in turmoil, and I was dreading the moment my daughter made her presence known. I heard her moving upstairs, stomping around, taking a shower, getting dressed for school. Charlotte gave no sign that she was thinking too strongly about what had happened the day prior, her uncomfortable discussion about Buttholing with Sabrina. If she was thinking about it, she wasn't giving any sign of it. And I gave no sign of the turmoil I was experiencing. As far as she knew, all was normal. She had no idea that something as crazy as our daughter sending me a picture of her asshole could have actually happened.

And she never could.

Charlotte was acting just like she did any other morning, as if nothing monumental had happened in this house the night before. She was dressed for work, in a pair of relaxed, khaki pants and a maroon top. She worked in an office, so she didn't have to exactly dress up, but she still looked nice. In general, she still looked good. Even though age had gotten to her a little bit, with her gaining a bit of weight, and her face gaining a few lines and wrinkles. But whenever I looked at her, I still saw the woman I had married twenty years prior. Sure, her butt was a bit larger than it was on our wedding day, as was her waist line. And she had to use dye to make her red hair shine as lustrously as it did when she walked down the aisle. But she'd kept me happy for twenty years, and I looked forward to twenty more.

I was shaken as I heard my daughter's approaching footsteps. I steeled myself for an uncomfortable moment, but when she sauntered into the kitchen, in a nice pair of jeans, fashionable sneakers, a slim nice top and a thin, pullover sweater, she looked every bit the daughter I always knew. And after sending me into turmoil, how did she act?

She said nothing. She did nothing.

She gave no sign that anything had changed. She didn't give me a single teasing glimpse or significant stare, acknowledging what had occurred between us. Did this mean nothing to her? Was what she had done so casual that it was almost normal for her? Par for the course? Uncaptivating?

"Morning!" Charlotte called out.

"Hey!" Sabrina replied, as she always did. Popping in a piece of toast, she made herself a quick breakfast before taking off to school. Her and her mother made conversation as I sat at the table, picking at my eggs, unable to focus, waiting for the moment where she'd do or say something.

But she never did.

The only thing she did to acknowledge my presence was a warm, friendly:

"Bye Dad!" she said, with a pretty smile, as she headed out to her car to head to school. That was it. Nothing else. No teasing. No acknowledgment.

What the fuck was going on here? Was I going crazy?

*************

(Sabrina)

Seeing my friends already at our meeting spot as I pulled into the parking lot, I zoomed into the nearest spot I could, parked, and ran towards my friends, unable to hide my excitement.

"What?" Cecilia called out, annoyed, as I burst into my circle of friends, pushing my way between two of them, Cecilia and Skye.

"I did it!" I said excitedly.

"Did what?" Cecilia said, still confused.

"I..." I began, before looking around, making sure the coast was clear. "I Buttholed my dad last night!"

"You're kidding?" Cecilia said, stunned, as my other friends looked at me, equally shocked.

"I did! Here!" I said, holding out my phone, showing proof of the picture I had sent to Dad last night. As they saw the proof of what I had done, and saw a glimpse of the conversation after, they looked at me, almost in awe. Cecilia, Skye, Devon, Julie... all of them looked flat out stunned. We had talked about this for a while, sure, a bit of fun fantasy, but no one thought I'd actually do it. But sensing a chance, seeing that I would have no better opportunity, I made the executive decision to kick off the plan. Now my dad, and my four best friends, were all in the game.

I should probably describe my friends to you.

Cecilia was my absolute bestie, and she had been for years. Since, like, kindergarten. A curvy, hot-bodied Puerto Rican girl, she turned heads wherever she went. Even I could admit she was hot. She was tall, with long firm legs. Her toned calves and smooth juicy thighs could make any man drool. She had a round, jutting, heart-shaped bubble-butt, which she always knew how to show off and use to her great advantage. She often wore tight jeans or yoga pants to show off every inch of her perfect lower half. And, on top of that, add in the fact that she had DD tits meant that her body was pretty much the total package. Combine with that her natural, striking good looks, her plump lips, stunning eyes, curly black hair, and perfect caramel complexion, she was a total babe.

But it wasn't her hot body, good looks, or general slutty lifestyle that made her such a hit with boys. No, it was her attitude. Her charisma. She was smooth with her words, forceful with her demeanor, seductive with her body, and aggressive with sharing pictures of her tasty naked flesh. At a school like ours, it almost went without saying that she fucking slayed her way through all the best guys.

And yeah, as I mentioned to my folks, she was the queen of Buttholing. She had a gift. Some people were athletes. Some people could play instruments. But Cecilia? She was the queen of taking pictures of her own butthole. Like I had explained, she used all these filters and lighting to make her asshole irresistible to whoever saw it. So many boys had fallen into the vortex that was Cecilia Rodriguez's butthole, and many more would in the future.

Skye was more the athlete of the group. Not that she was above sending out pictures of her own butthole to any guy she was pursuing. But her main talents were on the track, running cross-country, where she was a standout.

An athletically built, gorgeous black girl at a primarily white school, she turned heads wherever she went. Her long legs were taut and firm. Her belly flat and fit. Her arms lean and toned. Her upturned, D-cup breasts looking huge on her fit, athletic frame. And her ass... wow. Her juicy, firm, heart-shaped butt was truly jaw-dropping, catching people's attention in whatever she wore. It looked as good in her tight, stretchy athletic running shorts as it did in a thong. Some people would show up at the track meets just to admire the way the stretchy material of her shorts rode up her ass. Her rear just stood out, begging to be touched.

Her face held up its end of the bargain. Stunningly attractive, with almost model-like features, her striking eyes and brilliant white teeth could make the toughest man nervous. Her skin was smooth, chocolate-colored and perfect, and her curly black hair always looked stylish and sexy. And on top of that, she was fun to be around, with a biting wit and little shame at speaking her mind.

Skye had only moved here sophomore year, not having any friends or acquaintances in this area. But she announced her presence quickly. Within three weeks of her moving here, she was caught hooking up with the very handsome, VERY taken, varsity quarterback. A shockwave went through the school's social circles at this, and sensing a kindred spirit, I quickly befriended her, welcoming her into our group, where she fit right in.

Devon was kind of the princess of the group. She had rich parents. She had the best clothes. She was the first of our group to get a car. She liked shopping. She was, like, a total stereotype. Plus, she always acted like she was above it all, not giving people the time of day, barely ever taking her eyes off her phone. Very little really interested her anymore. Her folks had given her so much and taken her all over the world that the day-to-day of high school life barely registered.

She used to be a lot more fun. When we first met in middle school, she was bright and sunny and effervescent, but now... not so much. When she was younger, she used to be on the soccer team, and while she was pretty good, life got in the way. Or, to be more specific, the fact that she sprouted double-F cup tits over the summer kind of impaired her play on the field. Leaving behind her athletic pursuits clearly affected her, as she became a bit less pleasant to be around. Well, to be frank, Devon had kind of become a complete bitch. She had become super judgmental and was capable of saying some truly rotten things about people she didn't like. But she was still my friend, despite all this. Every group of friends had someone like Devon, right?

Her unpleasant attitude was only matched by her intense beauty. Devon was a fucking smoke-show, and she knew it. She was stunningly pretty, like a model, with big blue eyes, plump, sexy lips, and a perpetual pout that made all the boys melt. Her long, straight blonde hair poured down to her mid-back, and as she moved, it would ripple in hypnotic waves of gold. Her golden, tanned complexion only added to her appeal.

Her body matched up to her stunning looks. Her massive tits were round, firm, and springy, catching any guy's attention. They were fucking blimps on her chest, I swear. And her athletic background was especially noticeable after taking one glance at her jutting, heart-shaped ass, its immaculate shape highlighted in the tight skirts and pants she tended to wear. Her long, taut legs only further added to her beauty, making her stacked from head to toe.

While Devon no longer played sports, her competitive nature remained. It only got redirected towards the battlefield that was the high school dating scene. Despite how dismissive and mean-spirited she could be, guys still flocked to her, her above-it-all attitude irresistible to them. Devon loved seducing guys, and it really didn't matter whether they were with other girls. She didn't care if they were dating someone else, or another girl had staked her claim. If she wanted a guy, she would go after him, and she rarely failed. Other girls understandably hated her for carrying herself like this, but Devon hated most other girls, so it all worked out. And even though she was always dressed to perfection, every hair in place, her make-up perfect, there was a dirty little whore beneath the surface. She knew how to get down with the best of them, the filthier the better. So when I brought news of what I had done, Devon understandably perked up.

There was one more girl in our group, Julie. And she was easily the most different of all of us. She kinda knows that she's the nerd of our group, and she wears that like a badge of honor. She was the best student in our bunch, by far. She was the nicest of all of us, although, like... I like to think I'm pretty nice too. While all the rest of us were pretty shamelessly outgoing, she was relatively shy.

Looks wise, she was pretty, but in a reserved way. We joked a couple times that she's like the girl in the romantic teen movies before the makeover. Her dark hair was a little frizzy, and she would usually just leave it tied up in a simple ponytail. She had chunky black glasses, which only accentuated her nerd-look. But she was very pretty, her dark brown eyes highlighting her intelligence, with her bright smile and cute freckles only adding to her appeal.

She had a nice body too. D-cup breasts, a cute butt. She wasn't, like, a fitness queen or anything, but she still looked really good. And yes, she dressed down a bit, wearing simple tops and pants, nothing overly expensive or fashionable. She just didn't have an eye for that kind of thing, which was a point of humor among us all.

It probably sounds like she's the butt of our jokes, and while to a point that may be true, it really wasn't like that. Me, Julie, and Cecilia had been friends since, like, kindergarten, and that had never changed. Sure, we all grew up to be very different people, but our friendship had remained strong. We might tease her, but if some guy wronged her or broke her heart, our group would fucking tear him apart.

But she was no dainty wallflower. Girl had a dirty mouth, and she probably swore more than the rest of us. She was wicked sharp, too, always ready to make a snarky comment. But despite this snark, around guys, she could still be a little shy. While me and the other girls were pretty outgoing and very shameless, she was more conservative. I mean, she wasn't a virgin, but the stuff she had done barely counted in the grand scheme of things. She would often bristle as me and the other girls would talk about sex, but she didn't walk away, either. We all joked about how funny it would be if it turned out she was the sluttiest of the five of us. And every so often, with the way her eyes would widen as one of us shared our misadventures, I wondered if there was some truth there. But there were other times where she would put her foot down and be especially prudish. And today was one of those occasions.

"You did not!" Julie said, pushing in close. I tilted the phone towards her to prove it to her. Seeing that I had actually done what I said I'd done, her eyes went wide and her jaw dropped. "You seriously did this... are you crazy?" she asked, not hiding her judgmental tone.

"We all talked about it," I replied. "I saw an opportunity and I took it."

"You saw an opportunity to send your dad a picture of your butthole?" Julie asked skeptically.