Buttholing Ch. 01

This crush on Dad affected my relationship with Mom as well. Now, Mom had always been a pretty good mom. She was a bit prudish about some things, but overall, I loved her. She was a great and caring mom. But... me having a crush on Dad put her in the strange position of being both a mom and a romantic rival for me, a competitor to Dad's affections. So, I started thinking about her in the same way as I would a girl at school who was dating a guy I liked. I would examine her for imperfections, locate them, then trash-talk her behind her back. You know, typical teenage girl behavior. Like I said, I loved Mom, and face-to-face our relationship hadn't changed. But when I was around my friends, I would talk trash, tear her down, call her out, and my friends did the same. It was a stress relief, really, a healthy, satisfying way to vent my frustrations about not having Dad in the way I wanted. Neither Dad nor Mom sensed that anything had changed in me and how complex my feelings towards both had gotten. But those feelings had evolved, and I couldn't help it.

So, for the longest time, all was normal. Dad was just the object of fantasy. Burning hot fantasy, but fantasy nonetheless. He was unattainable. A trophy that was way out of reach, who we could never hope to conquer, despite the fact that his massive Dad-cock was, like, fucking built to be buried in hot, tight, eager teenage cunt. Me and my friends would gossip over every warm interaction we shared with Dad, or every stray innocent glimpse he might give us, which would be enough to fuel fantasies for weeks on end. We'd been trading stories and fantasies about him for a while. But none of us actually thought we would ever be able to do anything. He was too decent of a man. Too normal. And plus, you know, he was my father. Dad was always there, as this unattainable trophy way out of reach for mere girls like us.

So, we all dated around. A lot. If it wasn't clear by now, me and my friends were all pretty huge sluts. Well, maybe not Julie, but the rest of us were pretty experienced at taking the dick in so many wonderful ways. Me and my friends tore our way through the male student body, sampling the best and brightest of them. Riding every cock we could get our hands on, slaking our thirst, at least for the moment. But our shared crush on my dear old dad never went away.

So, you might be asking, how did it reach the point where I end up sending a picture of my asshole to my father?

It was simple. We were bored. Like I said, me and my friends had sampled pretty much any guy in the school worth having. We moved on to guys from nearby schools, the occasional college guy, and it was fun, but... there was no challenge. High school guys were easy. College guys too. There was no challenge there. I mean, at first, there were some guys in the school that were more unattainable than most. But, with the advent of Buttholing, those guys became very attainable.

I don't really know where this fad came from. I mean, it certainly started well beyond our school. It was, like, a worldwide thing, you know? And I don't know who the first girl was in the school who did it, but our group was certainly on the leading edge of it, for sure. Cecilia was the first to do it, followed by myself, then Skye, then Devon. By all accounts, Julie had never done it, but she was very protective about her phone, so I am not 100 percent convinced that if I scrolled through her pictures, I wouldn't find a picture of her asshole there, taken in a curious moment.

Once we embraced Buttholing, it allowed us to complete the set, so to speak. The last few guys at school who had escaped our reach finally fell to us. And that was the secret about Buttholing, the thing I didn't admit to Mom and Dad when they asked. The thing about Buttholing that made it special was that these pictures weren't just thrown about willy-nilly, although that does work just as effectively. But, the great thing about Buttholing was that it worked especially well on taken guys. I think it was specifically supposed to target taken guys, in fact. Guys in relationships. Guys in love with long-term girlfriends. Because once a girl has you locked down, they stop trying. But when you have another girl sending you pictures of her tight naked asshole, you start wondering what you're missing out on. And eventually, you just have to give in.

They always gave in.

It didn't take long for us, as a group, to have conquered pretty much every guy around us worth having. We could now trade notes on all of them and know who were the best and brightest. But it became clear that even this wasn't enough. We loved the hunt. The challenge. All the boys we had hooked up with had not satisfied our hunger. We needed to seek out bigger game. We needed to find satisfaction, and as time went on, it became clear we weren't gonna find it among the boys our own age.

We wanted men.

Not boys, but real men. Real men with experience. Real men who knew what they wanted and knew what they were doing. Real men with real cocks. Real men who can fuck and fuck and fuck and fuck and leave a girl a sweaty, quivering, cum-covered mess. That's what we wanted. That's what we needed. And as soon as we all came to this conclusion, high school boys became dull and uninteresting. Our eyes were looking onward to a world full of real men who could take care of us in the way we needed.

While I had my dad as my main focus of my desires, all the other girls had other men in their crosshairs, beyond just my dad. Devon had a burning crush on one of the guys at her dad's company, an older married man who had known her dad forever and Devon had always harbored feelings towards. Skye had been working out at this runner's clinic thing set up by this one really famous college track coach. Skye had it bad for that guy ever since they first met. One of Cecilia's much older brothers had a best friend who was this great guy. Successful. Married, with kids. He had started up this charity to help out inner city youths. Cecilia wanted him to fuck her in the ass. She wanted to be his whore forever. Even Julie, sweet, supposedly innocent Julie. Even though she denied it, she had this insane crush on our history teacher, Mr. Porter. Compared to the men we all had crushes on, he was younger, maybe only ten years older than us. But compared to some of the other teachers here, he was practically a peer. Since he was younger, he could relate to us better. And he was super smart and with it in a way most other teachers weren't. And while he was more relatable that way, he could also explain really intelligent complex issues in the news in a really smart way. Julie loved this type of conversation, and she always loved chatting with Mr. Porter. She'd show up early, and always raise her hand in class, and always make an excuse to chat with him. She totally denied it, but it was obvious she was madly in love.

And I had Dad. Like I said before, I wasn't, like, interested in a long-term thing with Dad. I mean, that was crazy. He was my Dad! But... if we spent the summer hooking up every chance we got, him railing my tight ass, feverishly groping my big boobs, and stuffing my tight cunt with his big, fat dad cock... that didn't sound so bad, did it? It wouldn't be such a big deal, right? I'd get to live out my biggest, most depraved fantasy, and go to college having experienced just about anything there was to offer. No damage done. Me and Dad could have beers down the line and laugh about the time me and him spent a whole summer banging each other's brains out.

It would be perfect.

While all of us girls were very experienced in the ways of seducing teenage guys, none of us had ever been with a real man. Sure, we were all hot, and we had our bubbly teenage charms, but would these tricks actually work on real men? Would all our moves really work on them? Younger guys are easy. Real men... they expect more than that, don't they. So, while we were quite confident around guys our own age, we were all a bit hesitant to try anything on these older men. These were real men. This was the real world. There could be real consequences to failing there.

Cecilia had been the one to suggest that one of us should Butthole one of our crushes. For a hot minute, she was gonna do it, but we talked her out of it. It was too big of a risk, right? That being said, she raised a good point. What if it did work? What if these tricks could actually work on a real man? Because if we could simply Butthole one of these men, and that would allow us to land the prize, then the door would be opened. If one fell, all of them could fall. If she Buttholed her crush, and they ended up hooking up, there was nothing to stop us from living out our dreams and hooking up with our dream men doing the same thing.

But none of us had the spine to actually do it.

I was in the worst spot, as I had the added obstacle of the whole incest thing. But then, my folks started asking about it. Inquiring about it. And, with that being out in the open, inspiration struck me. There would never be a better time than the present. Without thinking twice, I just did it. I sent my dad a picture of my gorgeous, naked asshole. My thought was, if my dad, the most unattainable of them all, gave in to the charms of Buttholing, all those other guys would fall even easier.

The funny thing was, I was pretty sure my dad was a boob guy anyways. I don't ever recall him glancing at my butt or any of my friends' butts in any inappropriate ways. The only time I'd ever caught him staring, it was at my breasts. And I had caught him staring when either Devon or Cece were showing some serious cleavage, but that had only been quick glimpses before he had stopped himself. But as I said before when explaining Buttholing to Mom and Dad, any girl could flash her tits, and that was great. But Buttholing was on another level. It was the secret ingredient. The process that makes men crumble, so that was the path forward. That was the game, and by sending a picture of my butthole to Dad, I had taken our first steps into it.

And after a few breathless moments of waiting after sending that picture, my dad replied. And the results were promising.

He was mad and upset, but he didn't tell on me. He didn't confront me in person. He didn't come out and say it, but he liked it. He was on the hook. He wanted more. A lot more. And he was about to get it.

As me and the girls made our way to our first class of the day, I sent one last text before pocketing my phone. Although it was less a text than a call to action. A starting shot.

I sent Cecilia, Skye, Devon, and Julie my Dad's cell phone number.

They'd been on me to give them his number for some time now. But I was smart, and kept that away from them. Knowing those sluts, they would have pushed things too quickly and flirted brazenly, like the whores they were, and push him away completely. I couldn't have that, at least not then. But now, it was time to unleash the Valkyries. I sent them Dad's cell number, and they knew what to do.

The game was on.

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

(Jim)

For a few stray, scattered minutes, I was actually able to forget about the fact that my daughter had sent me a picture of her asshole the previous night. I walked through work in a daze, not betraying any sign of the madness I had been pulled into.

I still couldn't wrap my head around it. My daughter... I repeat... MY DAUGHTER... sent me a picture of her exposed, naked asshole. It didn't make any sense. She didn't say anything about it this morning. She hadn't done anything since last night to give any sign of what she had done. It mattered to her that little that she couldn't even deign to give any sign to me that she was somewhat embarrassed or regretful about it. No, she just bopped along like it was any other morning, and I was the one stuck with a picture of my daughter's butthole on my phone and an uncomfortable erection in my pants.

Yes, yes, I know. I know. It was so fucked up in so many ways. I get it. I couldn't even explain it, honestly. I knew it was wrong. I knew I shouldn't get a single bit of pleasure out of this whole thing. But, as soon as I remembered what had happened... as soon as I remembered the picture Sabrina sent to me, my cock turned to into steel. Being so well-endowed, a thick, hefty, nine-inches, meant that I had to keep myself seated behind my desk most of the day, as to not attract any unwanted attention. I didn't really want to know why this picture turned me on like crazy, so I did just try to push it out to the periphery of my thoughts.

And yes, I do realize it would probably help if I just deleted the picture off my phone. But... I just couldn't. I don't know. I mean, obviously, it made sense to just delete the evidence, especially when it was something as crazy as this. But... if I just deleted it, that kinda felt wrong to. Like... if something greater came of this, and I had deleted the evidence, then it looked worse than it was, right? I had done nothing wrong, and this conversation proved it. So, reluctantly, I opted to keep everything on my phone. Now, I know this probably sounds like some excuse that would allow me to keep a picture of my daughter's hot, naked asshole on my phone, and being honest... that might be true. I don't know. I don't know! I hadn't begun to understand any of this, so for now... I didn't move things along in any direction. I just stayed in place and tried to make sense of this.

At times, I did my best to push this whole thing out of my mind. At other times, when unconsciously fussing with my phone, I would pull up the picture Sabrina sent me. I would gaze with full attention at her tight, puckered asshole, nestled between the firm, round cheeks. I would stare at it, studying it, finding myself almost hypnotized by every delicate line and contour. The snug, little hole, twisted into the tightest of knots, attracting my gaze despite me knowing better. I couldn't look away, and it was only when someone knocked at my office door would I stash my phone away and actually get back to work, trying not to be distracted by my bone-hard erection.

As soon as I made progress, or had ignored that whole thing for a while, my phone would buzz. In those moments, my heart would fill up with a combination of dread and excitement. Dread, for fear that Sabrina was pushing this game of hers even further, and excitement that this whole thing was moving along and I could better understand it. Alas, these were all false alarms, texts from coworkers, friends, or my wife.

This had to be a game. A sick joke on Sabrina's part. She could have a wicked sense of humor sometimes, but never to this level. I understand teenagers were very different now than they were in my day, but I didn't think they could be this shameless. If her idea of a practical joke was sending a picture of her naked asshole to her own father, that was something I could never understand.

By lunch time, after thinking about it almost all morning, that's where I ended up. This was all some twisted, sick joke at my expense. My reaction to it was, um... hard to explain, but my goal was to write it off, forget all about it and hope to move on.

Reaching lunchtime and feeling famished, I was about to step out and pick up something for lunch. As I leaned over to grab my phone, it buzzed beneath my fingertips. Reverting to muscle memory, I unlocked my phone to glance at what had been sent to me. And as soon as I did, my eyes widened and my breath caught in my throat.

I was staring at a girl's butthole.

I sat back behind my desk and just stared at it. It was different from Sabrina's. Glancing at the sender of this picture, it was a number I didn't recognize, but based on the amount of time I had stared at the picture Sabrina had sent me, I already knew this wasn't my daughter's asshole. Bent over in front of the camera, legs straight but angled slightly, reaching back and pulling her ass-cheeks with both hands, with her front resting against a wall to support herself, she posed for the camera with her asshole displayed prominently for the camera. I don't know how she was able to physically take this photo, if someone else was taking the picture, or if she had set it to take automatically. But it was a really good picture. Knowing this wasn't my daughter allowed me to appreciate it without hang-ups.

This girl had caramel-colored skin, looking smooth to the touch. While her body seemed taut and fit, she was curvier than my daughter. Her legs were thick, but firm, and her ass was larger and fuller. Between her legs was her puffy, petite pussy, making my eyes widen. But I didn't have time to admire it for too long, as my eyes drifted upwards, towards the main event of this picture.

Her lewdly showcased butthole.

Spread apart, her butthole was prominently displayed. Clean and tight, darker in complexion than my daughter's, it arrested my vision. The twisted little hole was being showcased lewdly, the lines around it converging at the tight hole in an almost artful manner. I couldn't look away from it. It was almost calling to me, yearning to be filled, either with one of my thick fingers, or even my... no. Don't think like that.

The picture itself was well done. It was like it had been fine-tuned after it had been taken. Her body stood out, her caramel skin almost glowing in the less interesting surroundings of her room. It was well-composed and focused, putting her butthole front and center. After a few moments of letting her asshole consume my attention, I looked past it, up this girl's taut, firm back. The back of her head showed her curly, black hair, pulled back in a pony tail to keep her hair out of her eyes. The side of her face was pressed against the wall, holding herself up, allowing me a glimpse of her face, leaving me able to figure out her identity.

Cecilia.

My daughter's best friend.

I was shocked. I had known her for years, since her and my daughter first met. Now, here she was, 18-years-old, sending me a picture of her asshole. I was so stunned that I couldn't stop looking at it. I just stared at her tight asshole, frozen in place at my desk. It was so lewd. So wrong. But here I was, staring at this wicked photo, unable to look away. And the worst part of all was that my cock was as hard as granite in my pants.

It was so lewd, seeing her displayed like this. She'd always been friendly to me, nothing out of the ordinary. That being said, even from afar, it wasn't difficult to see that of Sabrina's friends, Cecilia came across as the most promiscuous. So, in that sense, it wasn't that shocking that she would do this. But, seeing a girl that you knew as your daughter's best friend spreading her butt apart and sending her BFF's father a picture of her asshole was something I'd never be able to forget.

I looked up at her face, and the thing that leapt out at me was her confident smirk on her face, flashing her brilliant white teeth in the process. She was so self-assured, so proud of what she was doing. It was as if she knew how lewd and wicked this image was, and she greatly enjoyed it. That kind of confidence was undeniably sexy.

I almost jumped out of my skin when my phone pinged in my hand. I realized Cecilia had sent a follow up text, and I read the words quickly.

'I've been waiting to do this for so long, Mr. S. Enjoy XOXO.'

I gulped at this, knowing that behind our cordial interactions was some deep-seeded lust on her part. It was never coming from me, obviously. I never once looked at her that way. I was just a normal, regular dad. Honest. I wasn't this type of guy. I don't know why they felt like they could play this game with me. But here I was, staring rapturously at the pictures they had sent me.

Finally, I put my phone down. I put my face in my hands, trying to put the pieces together. It couldn't possibly be a coincidence that she sent me this picture about 12 hours after Sabrina did. Sabrina did hint that her friends would be willing to do something like this, but I thought she said that in jest. But clearly, it was the truth. And I had never once before been in contact with Cecilia on the phone, so Sabrina had obviously given her my number for this express purpose. To tease me. To penalize me for not playing along.