Buttholing Ch. 01

What do I do? I don't know. There was no precedent for this type of thing. It wasn't like there was some group of distressed fathers whose daughters send them teasing, sexually explicit pictures of their tight, naked assholes. What could I do? Knowing the impetuousness of teenage girls, telling them to stop would only embolden them further. Engaging them would only encourage them. And talking face-to-face about this... I couldn't imagine anything I wanted to do less. How do you even talk about something like this? No. I couldn't. My only hope was to just ignore this, and hope they got bored.

I picked up my phone, and got a glimpse of the picture Cecilia sent me. As I pocketed my phone, my stomach rumbled.

I was famished.

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

The rest of my afternoon was pure torture. Whenever my phone would ping, I was filled with a strange mixture of dread and excitement at the possibility of getting another lewd butthole picture, only to be disappointed to have it just be some boring work stuff. And the fact that I was disappointed filled me with guilt. And whenever I had to use my phone, I would find myself drifting back to the pictures that Sabrina and Cecilia sent me, staring at them, which would fill me with new waves of guilt. I knew it was wrong, but... I just couldn't stop myself. I didn't know why. I couldn't explain it.

But the game had only just started.

I was sitting in a meeting in the conference room during a big meeting, and although I had silenced my phone, the familiar vibrating on the table let me know I had a new text. I did my best to just ignore it and focus on the meeting, but the meeting got super boring, and the prospect of what had been sent to me was too inviting to resist. So, stealthily, I grabbed my phone.

Getting ready to glance at what I'd been sent, I paused. It wasn't like I was hoping for another Buttholing picture. Honestly, I wasn't. But... I was in uncharted territory, and the search for not only answers, but simply for more information, was better than nothing. The wait was almost worse. Something was better than nothing, even if that meant getting sent pictures of teenage girls' buttholes.

Sitting back and positioning myself so no one could see my phone, I unlocked it and glanced at what I'd been sent. My eyes went wide and my breath caught in my throat. It was another butthole picture! Holy fuck! I immediately realized this was from a different girl, neither Sabrina nor Cecilia. And it was shot much different from the other two. Whereas those two were bending over in front of the camera, this one was shot from below.

This girl, whoever she was, was wearing a thin, airy yellow sundress. And, as the picture made clear, she was wearing NOTHING underneath. She had lifted one foot up, resting it on a chair or something, allowing her to reach underneath and shoot a picture of her body underneath the dress. Front and center in the picture was her puffy pink pussy, adorned with a stylishly trimmed little strip of pubic hair. This position caused the lips to part slightly, exposing the juicy pink flesh within.

The picture showed her ass from underneath, and while it didn't give me the full picture of its size and shape, I could tell it was something special. It was very evident her ass was round and shapely, and this angle showed the delicate cleft underneath her ass-cheeks, where her butt met her legs. Her legs were firm and taut, and once it passed that cleft, the two cheeks jutted out, belying their impressive shape, round and smooth.

And it wouldn't be a proper Buttholing picture if I couldn't see her butthole, and it was right there. The position she was in parted the cheeks naturally, exposing the tight hole to the camera. And while, in the other pictures, the butthole was being presented front and center, this position gave a whole new angle on it. Below her pussy was a stretched strip of flesh, separating it from her other prized hole. From this angle, nestled between her shapely ass-cheeks, her butthole almost appeared concave, the tightened hole drawing your gaze inward, consuming your attention. I couldn't look away. This image was so raw and sexual that it almost hypnotized me. This girl, displaying herself like this... despite everything, I couldn't stop staring.

The sight of her asshole was so all-consuming that I hadn't even noticed that this picture gave a very primo view of what appeared be a pair of absolutely massive breasts. Beyond the expanse of her trim belly, her huge teenage tits jutted out, perky as hell, two luscious mounds of golden tanned flesh. I could almost see every inch of the undersides of her boobs, the massive orbs pressed together, ballooning outward in fleshy goodness. The thin dress struggled to contain them, straining against the front of her tits, obscuring her nipples from my view, unfortunately. Not that it should matter. I mean, I shouldn't honestly be getting any thrill out of any of this. But it was kind of infuriating. I could see her butthole. Why not sweeten the deal and show off some nipple too?

I didn't understand Buttholing, even after experiencing it first hand, but I had to admit, there was something about it. I mean, typically, I am more of a breast-man than an ass-man, so it would take something special to prevent me from noticing those mammoth tits first thing. And those big breasts were a clue to her identity. Going by the pattern of someone from her group of friends already doing this, I surmised this was one of her other best friends. And only one of her friends had breasts this freaking big.

Devon.

I mean, it's not like I was some pervy guy staring at my daughter's friends. But... like, they were impossible not to notice. Even Charlotte would joke around about the blimps on her chest. Quite frankly, every girl in my daughter's clique had impressively large breasts, Sabrina included, but Devon's were practically obscene.

But I had known Devon for years, I never got the impression that she had any warm feelings towards me. Although she'd always been polite to both me and Charlotte, she always came across kinda like a princess. Spoiled and preppy. Plus, she didn't strike me as being particularly fun to be around. Quite frankly, she came across as kind of bitchy. But, her and my daughter were very close, so who was I to say anything?

So, this girl who, at best, was merely polite to me, had sent me a picture of her asshole. Again, I ask... what the fuck was happening here? But she wasn't done, and she followed up this photo with a text.

"Does Mrs. Sanders do anything like this for you?"

Okay, admittedly, the fire between me and my wife isn't what it once was. But, we were getting older. It was understandable for our appetites to slow down. Personally, I would happily enjoy having a lot more sex than the 2-3 times per month me and Charlotte did now. But, she never really pushed the issue, and I got the message that things were slowing down for her. And although it does sound bad, I'd gotten used to it. My engines sort of slowed down to match hers, and not having to worry about draining my nuts on a constant basis really freed me up to focus on other things.

So, to answer the question, no, Charlotte wouldn't do anything like what these girls were doing. Not even close. Even in her younger days, she was not nearly this forward. If she had grown up nowadays, she would probably still be pretty old-fashioned, dressing sensibly, and behaving rationally, doing things the way they should be done. Not being as aggressive and raw as these girls were being.

I had to admit, there was a certain thrill at being exposed to something so illicit and sexually-charged. Because, as I said, things had slowed down between me and Charlotte. Age had gotten to us slightly. I didn't judge my wife for gaining a few pounds, or some wrinkles here and there. It was normal. I did my best to stay fit and hold off the wear and tear of age, and I had done a pretty good job, but I had some grey hairs in there which showed my age. It was some nice validation to be teased like this, even if this was all some colossal joke meant to embarrass me. I mean, if I was completely repulsive, I'd imagine these girls wouldn't give me the time of day. So, in that sense, it was kinda nice to be toyed with like this, but, uh... for every other reason, it was so, so wrong. Obviously.

I looked up from my phone, realizing I'd been lost in my own thoughts while staring at Devon's asshole. No one seemed to notice my silence, except maybe one of our younger associates, a cute brunette, maybe a few years out of college. As I glanced up and looked around, she gave me an almost knowing smirk. For a second, I was slightly nervous that she somehow knew what I'd been doing, but that was ridiculous. Would she seriously suspect that the older guy across the table had been sent a picture of one of his daughter's friend's butthole? I doubt it.

I did my best to focus for the rest of the day, but it came with great difficulty, as I kept finding an excuse to jump on my phone and I'd just happen to glance at those wicked pictures. I was kept at half-mast all fucking day because of this whole thing and it was very distracting. I didn't normally get so overcharged like this, but these wicked photos were clearly having an affect. I did my best to let my thoughts drift elsewhere, but it came with great effort. Finally, I just had to throw my phone in a drawer and just not think about it.

It was only when I packed up to go home that I grabbed my phone again, and it was only when I was sitting in traffic that those dirty photos ended up gracing my screen again. I flipped between them, from Devon, then to Cecilia, then Sabrina, hoping I could find some understanding of the situation in the tightly-drawn lines around their assholes. The tightly clenched holes consumed my vision as I tried to figure out what twisted game I had found myself in. As I sat there, staring, my phone pinged in my hand. My eyes widened, and excited for the first time to be stuck in traffic, I pulled open the text quickly. My breath caught in my throat and my eyes went wide.

It was another butthole picture.

The second I pulled open the picture, the mystery of the sender was answered. It was Skye, one of my daughter's newest friends. I had met her a few times, and she seemed very nice. But this picture was anything but nice.

I knew Skye was an athlete, a big track runner, and this picture appeared to have been taken after a meet. She was dressed in the school colors, black and red. On top, she had a thin, smooth, elastic top, leaving her fit arms bare, and clinging to her fit back. The picture was taken from behind, and from this position, the sides of her breasts could be seen, molded against the tight top. While she wasn't as chesty as some of her friends, she was no slouch there, and the round sides of them were very appealing.

But the main event of the picture was her ass, and it was being prominently showcased. She was using her sneaker-clad feet and taut, fit legs to really prop her ass outward, showcasing it. A pair of tight, stretchy running shorts had once clung to her rear end, but it had been pulled below her butt, exposing her delicious ass for the camera. She was looking back over her shoulder at whoever was taking the photo, her brilliant smile flashed at the camera, her gorgeous face looking absolutely stunning.

There was no ignoring that ass of hers though. It was truly fantastic, perfectly sculpted by years of running. Round and full and immaculately shaped, that ass of hers could make any man weak in the knees. Her dark, black skin arrested my vision, looking so smooth to the touch.

She was reaching back behind her, using her hands to spread her ass apart, showing off her butthole to the camera. Nestled in the dark crevasse of her ass-crack, her tight asshole looked smooth and sexy, the hole twisted into a tight knot. It was such a wicked sight, but it was that playful, knowing grin that stood out. It was taunting, teasing, as if she knew the exact dilemma a picture like this would cause.

She followed this up with a text, and what she said made my cock throb in pants.

"Do you want me to call you Daddy?"

Jesus.

I was shaken from my thoughts by a honking horn behind me. I looked up to see a huge gap in traffic in front of me. Apparently, I had been lost to the world while staring at Skye's asshole, and traffic had begun to move. Tossing my phone aside, I focused on driving home.

I didn't know what was gonna happen the first time I saw Sabrina. We'd crossed paths this morning, but she hadn't said a thing to me since she kicked off this whole thing last night. When I got home, Sabrina was holed up in her room, music playing as she did God knows what. I went to the kitchen, getting some early dinner prep done before Charlotte got home. I was chopping up some veggies when Sabrina padded in.

"Sup," she called out to me, walking over to the fridge, relaxed as ever, as if she hadn't, less than a day ago, sent me a picture of her own asshole. She had on a pair of thin, dark grey sweats and a yellow tank top. Her top clung to her upper half, straining against her large breasts, showing off a hint of cleavage, her cute navel, and her lithe arms. As she turned her back to me and opened up an upper cabinet, I couldn't help but glance at her ass. Based on recent events, it'd be hard not to. Even though her thin sweats weren't exactly figure hugging, it did a good job of showing off her full, round, shapely rear end. For someone as skinny as she was, it was a marvel that she had such copious curves in all the right places. Her butt jiggled ever so slightly as she decided what she wanted. My mind flashed to that photo she sent to me, with those round cheeks spread apart lewdly, displaying her asshole to me. I looked away quickly, hoping she hadn't noticed.

"How was your day?" she asked innocently, looking back at me and smiling warmly.

"Ummm... fine," I said hesitantly, my mind flashing to the barrage of asshole pictures sent to me. This here was my opportunity to have it out with Sabrina, to talk one-on-one about this whole thing, but when I finally found my words...

"How was school?" I asked, wussing out from asking about her and her friends Buttholing me, instead choosing to avoid the epic awkwardness of that conversation.

"Good," she said, pulling out a jar of peanut butter and a box of crackers. "Had a test in Chemistry. Nailed it, naturally," she said with a confident grin. She stood across the counter from me, dipping a cracker into the jar, scooping out a thick dollop of peanut butter and stuffing it into her mouth. "Gah uhh Calkuhluhs, um..." she began, but her mouth was full of peanut butter. She chewed up more and swallowed before trying again. "I've got a Calculus test tomorrow. I think I'm pretty set for that, though."

"Ah... the older derivatives and integrals..." I replied, continuing on as if things were normal.

"Yeah. And you know what, everyone always says it's, like, this nightmare, but it honestly isn't that bad," she said, shrugging her shoulders.

"I agree. I never thought..." I began, bonding with my daughter over math, one of my favorite subjects, but we were interrupted by Charlotte opening up the back door and stepping into the kitchen.

"Hey!" she said wearily. "Jim, can you help me out with a couple bags?"

"Sure," I replied. As I began to walk away, Sabrina waved goodbye, grabbed her food, and sashayed away, shaking her butt as she walked.

That was it. My daughter had sent me a picture of her butthole, and when I had the chance to bring it up with her and put an end to it, I didn't. I acted like things were normal, as did she. For a hot minute, I wondered if it was possible that maybe this was a prank being played on me, not by Sabrina, but by someone else, impersonating her, sending me lewd pictures of my daughter as some sort of sick joke. But the fact was, it was Sabrina's number that popped up on my phone, and she very clearly had her phone on her, as evidenced by the fact that she was on it all through dinner.

Nope. There was no doubt about it. And although she was playing innocent, and gave no outward sign of the naughtiness she had gotten up to, Sabrina had done this. I still don't know why, but she did. Was it a joke or a prank? Or deadly serious? Who knows? But she had done it, and I would have to deal with it.

I was distracted the rest of the night by what I had seen. The second my thoughts drifted, my mind would flash on those pictures I had been sent. While I sat near my wife, little did she know my mind was flashing on Sabrina's friends' assholes. As Charlotte and I made dinner together, could she possibly imagine that I was thinking about our daughter's asshole?

I still didn't understand what the point of Buttholing was, but I couldn't deny the dull ache it left in my crotch. I don't know why it would even be a thing that would be appealing. Perhaps it was the lewdness or wickedness of the act. Perhaps it was something as simple as it being enjoyable getting some attention, despite how wrong it was. Despite not being able to understand it, the consistent throbbing in my groin made it a situation that had to be dealt with.

Part of me hoped that maybe Charlotte would be frisky, but when I joined her in bed, it was clear she had other things on her mind. She was sitting in bed in her nightgown wearing her reading specs, looking at her tablet. As soon as I settled in, she put the tablet down and looked at me.

"Hey, do you remember that thing we were talking about yesterday, Buttholing?" She asked.

"What?" I asked, slightly panicked. Did she know something?

"I know you didn't want to really get into it yesterday, but..." she began. "I can't stop thinking about it."

"What do you mean?" I asked, still a bit panicked.

"Well, it seems like something that's so wrong and messed up and just... gross," she began, and I made sure to hide the erection Buttholing had given me. "I just... do you think Sabrina would do really anything like that?" I had to stop myself from letting my eyes bulging outward. Somehow keeping a straight face, I replied.

"I don't think so," I said flatly, giving no indication of the truth.

"It's just... she was being so coy about it. I can't help but be concerned. That kind of thing could get her in trouble," she said, not letting it go. "Part of me just wants to ask her flat out if she's done it, or if she's gonna do it."

"Hon... we made a deal with her. Diplomatic Immunity." I stated, hoping this fact would put an end to things.

"Who cares?" she replied, rolling her eyes. "Listen... I love Sabrina, and I know you do too. And I know she's a smart girl. But even smart girls make mistakes. And she's going to college soon. I'm just... I'm just afraid that if we don't do something now, if we don't put our foot down now, then this could be a slippery slope into something far worse. I don't think she's doing anything too crazy right now, but if she gets carried away, this could lead her to some really bad things. To being... promiscuous. We both know how crazy college kids can get. This could just lead to her looking for her next thrill. Maybe she'd then do multiple guys, or girls, or married men, or gangbangs, or God knows what. And then she could get pregnant too. And that's not even talking about alcohol and drugs, and..."

"Honey," I said calmly, trying to stop her.

"I'm thinking maybe we should look at her phone," she suggested, undaunted.

"Honey," I repeated. "You're fixating." I told her.

"No, I'm not! This is important!" she replied.

"Yes, you are," I replied. "You need to slow down and take a breath." At this, she did in fact pause in her spiel.

I was used to this kind of persistence from her. Honestly, it was one of the things that brought us together in the first place. We met in college, during our senior year. What made her stand out was that quality in her, that persistence. When you have an asshole teacher who you fantasize about calling out, it was intensely gratifying to have someone not let them get away with their bullshit. Charlotte was that person. When a teacher tried to pull something over, she would not let that fly. She would needle them, not in an annoying way, but in a way that exposed the inherent injustice in what they had tried to pull. Unfair grading, a bullshit question on a test... if you tried to pull that shit on Charlotte, she would not let you get away with it. That made her a fun person to have on your side in class.