Buttholing Ch. 01

The younger woman, Betsy, was a young upstart, a few years out of college. Smart and ambitious, she had a future in this company if she kept at it. I always enjoyed dealing with her, and she'd always been friendly to me.

So, when I entered the meeting online, I could see and hear them, but they couldn't see or hear me. They were sitting next to each other at a table. Cath, despite being older, was still very pretty. She'd kept up her good looks and had stayed fit, with a few wrinkles and some gray in her hair the only signs of aging. And Betsy was a stunner, pretty, with dark hair and a good tan. She dressed nice in a flattering business suit. As Betsy and Cath waited for me to show, they chatted with each other, and I could listen in.

"While we wait for Jim..." Cath asked to her younger coworker. "This might sound crazy, but..." she began, her voice getting lower. "Have you heard of this thing Buttholing?"

"Wow!" Betsy said, smiling. "I'm surprised you've heard about that!"

"Why?" Cath asked. "Surprised an old lady like me knows about Buttholing?" she asked with a laugh.

"Well... you're so classy. You go to the symphony and you always talk about art and stuff. I'm surprised something like Buttholing entered your hemisphere." Betsy said.

"So you do know about it?" Cath inquired.

"Uh, yeah, I do, cause it's the best thing ever!" Betsy gushed.

"Really?" Cath asked. "Why is this a thing?"

"Because it drives men nuts!" Betsy replied brightly. "I'm totally serious. Like, okay, there was this guy I had a thing for. But he was kinda... sorta... married. I know it was wrong to want him, but I was, like, totally in love. I'm serious. So, I got a little drunk, and my friends convinced me to send him a picture of my butthole. I thought it was silly, too, but I ended up doing it, and uh... well... turns out my crush was even better in bed than I dreamed he would be."

"You're so bad!" Cath said with an amazed smile. Betsy grinned and shook her head.

"I can't explain it, but it works. Guys go crazy about it! But honestly, Buttholing really is the best. Like, as a girl, you feel so sexy doing it. And the sex afterwards is amazing! The best I ever had. Guys lose their minds about it. Like, he was totally in love with his wife, but now, after I sent him a picture of my fucking butthole, the divorce papers are in the works. It's the best!" Betsy gushed.

"Wow..." Cath said, taken aback by how forthcoming Betsy was.

"You think I'm crazy, but you should try it," Betsy said, grinning. You could pull it off," Betsy said. Cath shook her head and smiled. "You should try it on Jim. That'll get him right into the meeting! Haha!" Cath stopped shaking her head as Betsy's words hit home. Betsy sensed this and moved in. "Oh my God, Cath! You've thought about it, haven't you? With Jim? I knew it! I knew you always had a thing for him!"

Cath shook her head, but she couldn't say anything in response.

"Hon! Don't worry, your secret's safe with me," Betsy said, holding the older woman by the shoulder. "And you've chosen right. Jim is so fucking hot!"

"He is so fucking hot," Cath repeated softly, nodding her head. She turned to face her younger friend. "I've had a crush on him for years," she admitted, as if sharing a deep dark secret with this younger woman.

"Cath, I'm serious. You should do it. Spread your butt-cheeks and send Jim a picture of your butthole. I can help if you want," Betsy offered. "You have a chance. I've met his wife. She ain't got nothing on you. You're hot! And she's not!"

"I know," Cath agreed, smiling. "When they first met, I was unimpressed. She's so dull and boring. But I stepped back and didn't get in the way."

"Hon," Betsy began. "When you feel strongly about someone, you HAVE to get in the way. That's what makes it exciting. I'm sure we're not the only ones who've noticed how hot he is. If you don't act now, someone else will."

What was this? Cath had a thing for me? She'd had a thing for me this whole time? And they both thought I was really hot? And both her and Betsy felt that negatively towards my wife? What the fuck? And Betsy was trying to convince Cath to Butthole me?

In a panic, I exited the meeting and closed my browser. I waited a few moments before trying again, booting up the webpage and trying to enter the meeting again. And this time...

"Hey, how are you doing?" Betsy greeted me warmly.

"Hi Jim!" Cath greeted me professionally, betraying nothing of the conversation she'd just taken part in.

Somehow, I made it through the meeting. I'm sure they noticed something off with me, but I got through it without too much damage. When the meeting ended and I closed down the browser. I put my head in my hands. I could hear the blood rushing behind my ears. The pressure was on.

Everywhere I went, Buttholing found me. I tried to get away, but it was trying to pull me back. My wife... people I dealt with at work. Would I be able to escape, or was I completely surrounded? I leaned back in my chair and sighed, only for the dull vibration of my phone on my desk announcing another text received. Another butthole picture waiting for me to gaze upon it.

I made my way through the work day in a daze. I was almost waiting for the next shoe to drop. For some other random thing to strike. I looked towards some female coworkers and wondered if they felt the same way Cath and Betsy did. I looked over at Cindy, an attractive Latina woman with a biting sense of humor. She always treated me warmly, never busting my balls like she did with some of the other guys in the office. Was she preparing to Butthole me like my daughter and her friends had? Would she bend over, pull her thong to the side, because a woman like her was totally wearing a tiny little thong every day, and show me the goods? At this rate, I'm sure she would.

There was this cute young secretary, very reserved and shy. Was she hiding a temptress beneath her conservative clothes? Was she like Julie, someone who seemed nice and friendly but could be just as wicked as the rest of them?

Everywhere, a reminder. Charlotte forwarded me an email about the Buttholing meeting she was attending, as a way to subtly convince me to go with her. So, there was no safety from her. I'd try to focus on my work, but I'd look up and see a pert female butt walking by, and all I could do was imagine her cheeks spread for my pleasure.

And through it all, the buzzing of my phone. On my desk, vibrating over and over again. Every time I was walking in the office, it was vibrating in my pocket, an unescapable taunting, begging me to look. During a meeting, when I set my phone down on the table, whenever it vibrated, the women at the table glanced at me and part of me wondered if they knew what I was being sent. It seemed like these girls had a sixth sense and I legitimately thought I could see them each smirk.

The worst was when I was alone. By myself in my office, with my phone buzzing every few minutes, taunting me. I couldn't toss it away because I needed it for work. But I wanted nothing more than to throw it into the wall and have some peace. I had no distractions, just alone with temptations. Sweet, delicious temptations. If I got on my computer, some reminder of what I was trying to avoid was there. Same with glancing out at the office. I tried to think about my wife, my marriage, but that all went back to Buttholing. And the phone, buzzing, always buzzing, with butthole after butthole after butthole, taunting me, begging me to look at them, each one sending a new throb through my almost permanently hard cock.

My daughter had done this to me. She had kicked off this crazy game, and in doing so had driven me to this frenzied state. She was the cause of me being so insanely turned on. She had pulled me into a web of lust and sin I'd never known existed, where every thought and sight around me were constant reminders of Buttholing. And I didn't know what to do about that.

It was all around me. I couldn't escape. I had to do something or I'd go insane. I'd explode, or do something I'd regret. I had to take a risk. I had to act. My mind was against me. My body was against me. For the sake of normalcy, for the sake of my own sanity, I had to do something. Damn the risk.

The decision was made.

I stood up and marched over to my office door, my mind a blur. I locked the door, and marched around my office, closing the blinds, making sure no one could see inside. Knowing I was protected, I headed back to my desk, grabbing my cell phone quickly, opening it up. Ignoring the dozens of missed texts, I opened up the camera.

Angrily, I reached down to my belt buckle, undoing it. Seeing red, and knowing I had to act without thinking twice, I reached down into my underwear and grabbed my thick, pulsing cock. I was as hard as I'd ever been, and it was tricky hefting out my sizable weapon, but I did so, letting it hang over the hem of my boxers. I felt a temporary relief, the pressure of my cock in my boxers alleviated as it stood out in my office, swaying in the cool recirculated air. I looked down at myself, examining my furiously hard cock. My rock hard pillar looked pretty damn good, smooth and thick and meaty. The base of my cock was kept cleaned and trimmed, really letting my impressive size shine. It was normally a good nine-inches, but I was so hard and swollen that I swear I had gained a bit more length. I know that coke-can thick was a common descriptor for this type of thing, but at this point, it felt apt. At the end of my cock was the swollen, angry tip, desperate for release, desperate for something to relieve the pressure.

Below it, hanging down, were my swollen, heavy balls, swimming with sperm. My heavy sack looked even bigger than normal, as this self-enforced exile from indulging in the pleasures Buttholing left me extra charged up.

I couldn't think twice. I had to do it. Looking down and lifting up my phone to my face, I snapped a quick dick pic, my sizable weapon centered in the frame. Opening up the text chain from Sabrina, and scrolling past picture after picture of her mouth-watering asshole, I attached the picture of my cock to a text and then, with a deep breath, hit send.

I exhaled deeply, putting down my phone and moving around my desk, falling to my chair, my cock still hanging out of my pants. I panted, breathing deeply. I did it. I just sent a dick picture to my own daughter. I gave her exactly what she wanted in her twisted games. And the funny thing was, at the moment of truth, that thought was what was on my mind. Not just that I was getting barraged by Buttholing pictures to the point of insanity. It wasn't just about getting them to stop and getting some peace and quiet. No, it was about giving her what she wanted. What she'd earned. It was about accepting the rules of Buttholing and embracing them. I had sent my daughter a picture of my hard cock, because she had earned it. Because she deserved to see what she had done to me.

Looking up, after spending day after day with my phone vibrating almost constantly, I finally had silence. No new texts. No more barrages of buttholes. Nothing. And for those amazing few seconds, I thought it was finally over.

And then my phone buzzed.

I reached forward and grabbed my phone. Gulping, I opened it up, finding a single, solitary text from my daughter. And it was only one word.

'Jesus...'

I think even she was shocked that I had done it. Angry and upset that it had come to this, I replied quickly.

'This is over.' I said firmly.

Absent mindedly, I scrolled up through all the butthole pictures I had missed in my exile, all the spectacular ones from Sabrina, and the other girls as well. Cecilia, and Skye, and Devon, each one as sexy as the last. There was even one from some random woman whose number I didn't recognize, with her bent forward, pulling her cheeks apart and taking a photo. She claimed afterward that it was a wrong number, but with how things had been going, I doubted that. But seeing all these other girls' pictures made me think of something.

'Don't send that to anyone,' I warned her. She responded quickly.

'Well, too late for that. I sent it to all the other girls as soon as I got it...' she replied. Jesus, Sabrina, I thought in a panic. If this got out beyond just us... I could be ruined. This was supposed to end this.

'Sabrina!' I replied angrily.

'They sent you dozens of pictures of their buttholes, Dad. You sent back one picture of your dick. It's only fair. They earned it. If anything, you should be sending more pictures...' she said. And then, before I could reply, she continued.

'Dad, I just have to say... your cock is fucking huge!' she gushed, and I couldn't stop the thrill of pride course through me at this, despite this compliment coming from my daughter. 'Thank God you sent this now. We were about to give up and just stop.'

'Oh fuck off...' I replied before I could think twice.

'Hahaha,' she giggled at me. A moment of silence fell between us. I didn't know what to say. On one hand, I has been slightly relieved that the pressure was off, thinking this was over, but I never thought about what would happen beyond it.

'Sabrina... the game is over.' I intoned to her.

'I mean... wow! That is the biggest cock I've ever seen in my life,' she said, undeterred. 'God, your balls are huge too!'

'Sabrina, don't talk like that.' I warned her.

'What? You don't like having your hot, super slutty daughter talk about how AMAZING your cock is?' she said, and these wicked words sent a jolt through my still erect weapon.

'Not really," I texted back, trying to stay calm as my daughter's words made my cock twitch with delight.

'I bet Mom wouldn't know the first thing to do with a cock like that. She's too narrow minded.' she stated.

'Don't talk about your mother like that!' I replied, even though deep down I knew it was true. She couldn't do any of the wickedness Sabrina and her friends had conjured up in my mind.

'Why? Mom freaked out over a butthole! Admit it, Dad. She can't possibly excite you. She's a boring, unattractive prude who no man would ever want to have sex with. Especially you.'

'Sabrina...'

'Don't even try to pretend you're still attracted to Mom. With the way you stared at us last weekend, you seem pretty desperate to cheat on her. You were SO obvious!'

'No, not true.'

'She's so plain and unsexy that you started having to fantasize about your own daughter just to get off. You would rather jack off thinking about your daughter's tight asshole than ever hook up with your own wife.'

'No...'

'My butthole is sexier than Mom all together, right?'

'Sabrina...'

'Just admit that you find your own daughter incredibly sexy. I NEED to hear you say that, Daddy. You have no idea how badly I need to hear that...'

'Sabrina... I can't say that.'

'Daddy! Please! You've been getting so turned on thanks to us. We all know it. I just want to hear you admit it.'

'Sabrina... no...' I pleaded, my hand unconsciously stroking my aching cock.

'Dad! Why are you playing dumb now? I sent you a picture of my tight, naked asshole. And you sent me back a picture of your hard, throbbing cock. We both know what comes next. We both know what ALWAYS comes next.'

'That can't happen...' I said, trying to be somewhat parental while stroking my throbbing dick.

'Dad, I don't want there to be any mystery here. This whole thing isn't a game or joke or anything. It's for real. Me and my friends all think you're REALLY hot, and we all want to have sex with you. Me especially.'

'Don't say that.'

'But it's true! All we talk about anymore is the bad things we want to do to you. You should hear the sick, fucked up shit we want to do with you. It's awesome! You'd love it!'

'Honey...'

'Don't act so shy now. You literally just sent your own daughter a picture of your perfect, big, fat, juicy Dad-cock!'

'Sabrina...'

'You're so fucking hot! You're way hotter than any guy I know. And you have the greatest, most perfect man-cock I've ever seen! I love it!'

'Don't talk like this...'

'I wanna touch it. I wanna stroke it. I wanna smell it. I wanna lick it. I wanna suck it. I want to fuck it. I want to feel every fucking inch inside my tight teenage cunt.'

'Jesus.'

'I am SO ready, Dad. Let's fucking do it. I can cut out of school right now, and you can leave work. Let's both go home, get naked, and just FUCK! We have hours before Mom gets home, and we can just go to fucking town on each other.'

'Sabrina, we can NOT do any of that!' I stated firmly, vigorously jacking off.

'Are you sure? I'll let you do whatever you want to me...'

'Please stop...' I said as an uncontrolled groan escaped my throat as my hand picked up speed.

'You'll get to see my big tits bare. I know you want to see them. And you'll get to play with them as much as you want. Touch them... feel them... squeeze them... suck them. I'll let you pinch my nipples, Dad. I know you want to. I know dads like you LOVE girls with big tits.'

"Oh!" I grunted out, my cock twitching with delight as I eagerly stroked it, her words hitting me just right.

'I know what I'm doing, Dad. I've been with a lot of guys. I mean... A LOT. Does that make you jealous? So many guys have had me. Do you wish it had been you instead? Well, it should have been you, and you can make up for lost time starting today.'

"Fuck..." I groaned, my cock almost numb with pleasure. I was getting really close.

'I think it's time my tight asshole and your enormous Dad-cock become very well acquainted with each other.'

That did it.

"Ahhh! Fuck!" I groaned as my cock flexed and jet after jet of thick white cum fired from my overcharged, rock-hard weapon. I pointed it away from me, towards the desk as long bands of thick semen exploded out of me. My swollen nuts flexed over and over again as my pulsing dick fired broiling hot cum all over the top of my desk. I looked up and noticed the framed senior photo of Sabrina on my desk, just in time for bands of my thick seed to land on her smiling face. "Oh!" I groaned, stroking my dick rapidly, trying to drain my nuts. Jizz kept firing out of me for a few more moments until the flow finally started to dissipate, and the last of my seed ended up on my hand as I squeezed it out.

I fell back and panted for breath, recovering from what might be the biggest orgasm of my life. As I did, the reality of what happened just hit me. I had sent my own daughter a picture of my naked cock before jacking off while texting with her. As she texted me her desire for rough, wild sex with me, her own father. And I did it here in my office at work, and she was probably just sitting there in class innocently as she drove me crazy with such filth. She should be paying attention in class, not trying to tempt her father into illicit, incestuous fucking.

As the full weight of what I'd done really began to wash over me, I knew I had to get myself together. I stood up, tucked myself into my pants, and moved to clean up. Luckily, I had an adjoining, private bathroom, so I was able to wash my hands. Fortunately, in the mess I had made, I had avoided getting any cum on me, other than my hands. My desk was another matter.

Grabbing a roll of paper towels, I walked back into my office. Part of me ashamed of how I'd lost control and made such a mess. But another part of me was weirdly proud of the massive wad of cum I had just fired. I had never cum like that... ever. It was as if I had cum despite myself, as the pressure became too much to bear, like a geyser. I quickly cleaned up the giant load I had just fired, with only a few papers ruined by my seed. I felt a strange mixture of feelings as I cleaned off the picture of Sabrina, the cum on the picture of her gorgeous face an image that would forever be burned into my mind. Just as I finished up, my phone buzzed once again. A little nervous, I sat back down and grabbed my phone, looking at what she sent me.