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I’m going to confess the filthiest thing I’ve ever done, the thing that would get me evicted from my friend group.

Anyone would judge me, but the truth is, I have zero regrets.

Context: I’m fifty-one. Divorced, two kids, yadda yadda. My oldest is in college, but my youngest is seventeen. I have a group of friends who are also fathers, and since our kids are around the same age, we hang out a lot. Backyard barbecues, movies, whatever.

My friend Gary has three daughters. His youngest is the same age as my youngest, and his oldest, Kirsten, is twenty-two. Old enough to drink, which means she’s been hanging with the adults at the barbecues for a few years. She’s a funny girl who always seemed mature for her age, so none of us minded when she started joining us.

About a year ago, though, something changed.

Kirsten got insanely hot.

I know. This makes me a bad father. A bad person. Whatever else you want to call me. But it isn’t like I watched the girl grow up — she was just there sometimes, playing in the background. I only started to pay attention when she joined the drinking circle, and for the first year of that, she was still a gangly, pimply sort. Now, though, she’s leggy, clear-skinned, and athletic, with a perky body. She even smells good, like vanilla.

Even though I hated myself for it, I started fantasizing about her. I’d jerk off to thoughts of her, pretending she was a stranger rather than my friend’s daughter. Every time I saw her, she looked more and more appealing, and it got to the point where I had to excuse myself to the bathroom to masturbate after talking to her.

I felt like such a creep, but the attraction was uncontrollable. Pheromones or something. But I managed to resist the urge to pull her into a closet and fuck her brainless.

Here’s the part where I become a terrible person.

There are six girls in the friend group, and they like to hang out away from the adults. Sleepovers when they were younger, house parties and dinners now. But for some fiendish reason, they all decided to have a sleepover again, even though most of the girls are in college. And they decided to have it at my house.

The girls camped out in a den on the second floor while I stayed in my bedroom on the ground floor. After greeting them at the door and showing them where the food was, I locked myself in my room, trying not to think about Kirsten sleeping under my roof. I drank a few beers and jacked off, but I couldn’t sleep. Every time I closed my eyes, I thought about her.

Finally, around 1AM, I went to the kitchen to grab another beer, hoping that would knock me out. When I was bent over in front of the fridge rifling through leftovers, I heard footsteps behind me.

Kirsten was standing in the entrance to the kitchen. She was wearing tiny sleep shorts and a tank top with no bra, and her hair was a little tangled. It made me imagine gripping it in my fist and forcing Kirsten to her knees.

“Can I help you?” I asked, hoping she wouldn’t notice the erection tenting my pajama pants. I was shirtless, too — I work out, so I’m not too worried about my appearance — and it made me think how close we both were to being naked.

“Why didn’t you come hang out with us?” she asked, moving closer. “I thought you’d at least be up for a drink.”

“It’s a girl’s night,” I said. “I know when I’m not wanted.”

She grinned. “Now, how could you know that?”

I’m pretty sure I prayed to every saint I could remember the name of, asking for help to resist that bit of flirtation. I stammered a little, and when her eyes skated down my body, I shut the door of the fridge so it couldn’t illuminate the outline of my dick. Then I realized I hadn’t gotten a beer yet and opened it again. I was an idiot.

She nodded at the fridge. “Can I have a beer, too?”

That’s how I ended up sitting at the kitchen island across from Kirsten at 1AM, hardly able to focus on drinking my beer. Her nipples were hard, and every time she shifted on the stool, the fabric of her shorts rustled and made me imagine what was under them.

We’d been having a fairly normal — if stilted — conversation when she asked the question that changed everything. “Do you like anal?”

I choked on my beer. “What?”

She shrugged. “The guys at school are always after it, but I’m not sure what the fuss is about. I’m curious, but honestly, I don’t trust college boys to do it right.”

My dick was so hard I felt faint from the abrupt loss of blood to my head. “This is not an appropriate topic of discussion.”

She laughed. “I never guessed you’d be so stodgy.” When she looked at me again, there was heat in her eyes. “Don’t pretend you don’t ogle me every time I enter a room.”

The situation was spiraling out of control. My friend’s daughter. My daughter’s friend. But the reminders didn’t do anything. “That’s — I — ” I ran out of words, because what does someone say to that?

“You’ve always been the hot dad,” she said, sliding off her stool and walking around the island toward me. “If you’re not into it, I get it, but I was kind of hoping you could show me the ropes.”

“The...anal ropes?” I clarified, turning around on my stool to face her as she approached.

She nodded and climbed into my lap, straddling my erection, and that was it. I was done for. My hands gripped her ass like they were possessed, and I picked her up and carried her out of the kitchen to my room. She laced her legs around my back, already kissing my neck.

I tossed her to my bed and landed on top of her. We made out frantically, and when she undulated her hips while rubbing against me, I nearly lost my mind.

“Need to do something first,” I said. I took my pajama pants off, then stripped her top and shorts off to reveal perky little breasts and a breathtaking pussy. She widened her legs and then spread her labia with two fingers to show me how wet she was.

I took the invitation and ate her out. She was tart and sweet, and her responses were incredible. As I fingered her pussy and lapped up all that wetness, she pinched her nipples. When I found the right force and rhythm, she orgasmed with a little stuttered moan that was the sexiest thing I’d ever heard.

“Now,” she told me, pushing my head away, “you know what I want.”

I retrieved a condom and the bottle of lube I optimistically kept in my bedside drawer. “The key to anal is to take it slow,” I told her. “And to lubricate a lot.”

I moved her to her hands and knees and widened her legs until the pucker of her asshole was revealed. She was perfect there, too. I licked it a few times while she squirmed, then I lubed up my fingers and started stroking over it. Periodically I dipped a finger an inch or so inside, letting her get used to the sensation.

When she was bumping her hips back against my hand asking for more, I slid my entire finger in. She was hot and tight, and I nearly short-circuited thinking about what that channel would feel like around my dick. I worked my finger in and out gently.

She sighed and rested her head on her hands. “This is way better than I thought it would be.”

“We’re only starting, sweetheart.” Satisfied that she was into it, I added another finger. She shivered and shifted uncomfortably, but soon enough she settled back down. In and out, in and out. I stared at my fingers and the glistening lube as they pulled out of her ass. It was my filthiest fantasy come to life.

“I want all of it,” she said, looking back at me. “I want your cock.”

Those words sent a jolt of pleasure through me. I reached for the condom, but she shook her head. “I want it bare,” she said, “unless there’s a reason we shouldn’t. I’ve been tested.”

“Me, too.” I stared at her upraised ass and the curve of her back, her wet pussy and wicked smile. Was this actually happening? Was I about to fuck my friend’s daughter in the ass?

Yes. Yes, I was.

I lathered my cock with lube while she watched with interest. Then I positioned myself behind her and placed the head against her hole. I pushed into her a little, massaging her clit as I did.

She hissed in a breath and tensed, so I stopped an inch in and focused on working that swollen little clit. When she relaxed again, I took a little more.

The more she took, the more she seemed to like it. Soon I was seated balls-deep in her tight, hot ass, and her pussy was soaking my fingers. She moaned and rocked on me, sending my dick in and out. She was fucking herself with me.

I felt like I was going to spontaneously combust, so I stilled her movements with my hands on her hips and took a deep breath to settle myself. When I was in control again, I started fucking her.

I went slow so she could get used to it, but she was soon begging for more. “Touch your clit,” I told her, planting my hands on the bed on either side of her. “Make yourself come.”

I fucked her hard in the dirtiest version of doggy style, relishing that tight ass that squeezed me like a fist. She moaned with each thrust, and soon the combination of my dick and her masturbation set her off. She screamed into the sheets.

A few more good thrusts and I came, shooting my load deep into her. Her ass squeezed me the whole time, like her body was milking every last drop I had to offer. When I pulled out, come trickled from her hole.

“Well?” I asked as we both collapsed. “Did you like it?”

“I loved it.” She grinned at me. “And now you’re definitely the hottest dad.”

Judge me if you want, but being in that ass was heaven. I would do it again and again. In fact, I’m going to — the next morning, Kirsten asked the other girls if sleepovers could be a regular thing.

" />

Naughty Daughter

Trama

I’m going to confess the filthiest thing I’ve ever done, the thing that would get me evicted from my friend group.

Anyone would judge me, but the truth is, I have zero regrets.

Context: I’m fifty-one. Divorced, two kids, yadda yadda. My oldest is in college, but my youngest is seventeen. I have a group of friends who are also fathers, and since our kids are around the same age, we hang out a lot. Backyard barbecues, movies, whatever.

My friend Gary has three daughters. His youngest is the same age as my youngest, and his oldest, Kirsten, is twenty-two. Old enough to drink, which means she’s been hanging with the adults at the barbecues for a few years. She’s a funny girl who always seemed mature for her age, so none of us minded when she started joining us.

About a year ago, though, something changed.

Kirsten got insanely hot.

I know. This makes me a bad father. A bad person. Whatever else you want to call me. But it isn’t like I watched the girl grow up — she was just there sometimes, playing in the background. I only started to pay attention when she joined the drinking circle, and for the first year of that, she was still a gangly, pimply sort. Now, though, she’s leggy, clear-skinned, and athletic, with a perky body. She even smells good, like vanilla.

Even though I hated myself for it, I started fantasizing about her. I’d jerk off to thoughts of her, pretending she was a stranger rather than my friend’s daughter. Every time I saw her, she looked more and more appealing, and it got to the point where I had to excuse myself to the bathroom to masturbate after talking to her.

I felt like such a creep, but the attraction was uncontrollable. Pheromones or something. But I managed to resist the urge to pull her into a closet and fuck her brainless.

Here’s the part where I become a terrible person.

There are six girls in the friend group, and they like to hang out away from the adults. Sleepovers when they were younger, house parties and dinners now. But for some fiendish reason, they all decided to have a sleepover again, even though most of the girls are in college. And they decided to have it at my house.

The girls camped out in a den on the second floor while I stayed in my bedroom on the ground floor. After greeting them at the door and showing them where the food was, I locked myself in my room, trying not to think about Kirsten sleeping under my roof. I drank a few beers and jacked off, but I couldn’t sleep. Every time I closed my eyes, I thought about her.

Finally, around 1AM, I went to the kitchen to grab another beer, hoping that would knock me out. When I was bent over in front of the fridge rifling through leftovers, I heard footsteps behind me.

Kirsten was standing in the entrance to the kitchen. She was wearing tiny sleep shorts and a tank top with no bra, and her hair was a little tangled. It made me imagine gripping it in my fist and forcing Kirsten to her knees.

“Can I help you?” I asked, hoping she wouldn’t notice the erection tenting my pajama pants. I was shirtless, too — I work out, so I’m not too worried about my appearance — and it made me think how close we both were to being naked.

“Why didn’t you come hang out with us?” she asked, moving closer. “I thought you’d at least be up for a drink.”

“It’s a girl’s night,” I said. “I know when I’m not wanted.”

She grinned. “Now, how could you know that?”

I’m pretty sure I prayed to every saint I could remember the name of, asking for help to resist that bit of flirtation. I stammered a little, and when her eyes skated down my body, I shut the door of the fridge so it couldn’t illuminate the outline of my dick. Then I realized I hadn’t gotten a beer yet and opened it again. I was an idiot.

She nodded at the fridge. “Can I have a beer, too?”

That’s how I ended up sitting at the kitchen island across from Kirsten at 1AM, hardly able to focus on drinking my beer. Her nipples were hard, and every time she shifted on the stool, the fabric of her shorts rustled and made me imagine what was under them.

We’d been having a fairly normal — if stilted — conversation when she asked the question that changed everything. “Do you like anal?”

I choked on my beer. “What?”

She shrugged. “The guys at school are always after it, but I’m not sure what the fuss is about. I’m curious, but honestly, I don’t trust college boys to do it right.”

My dick was so hard I felt faint from the abrupt loss of blood to my head. “This is not an appropriate topic of discussion.”

She laughed. “I never guessed you’d be so stodgy.” When she looked at me again, there was heat in her eyes. “Don’t pretend you don’t ogle me every time I enter a room.”

The situation was spiraling out of control. My friend’s daughter. My daughter’s friend. But the reminders didn’t do anything. “That’s — I — ” I ran out of words, because what does someone say to that?

“You’ve always been the hot dad,” she said, sliding off her stool and walking around the island toward me. “If you’re not into it, I get it, but I was kind of hoping you could show me the ropes.”

“The...anal ropes?” I clarified, turning around on my stool to face her as she approached.

She nodded and climbed into my lap, straddling my erection, and that was it. I was done for. My hands gripped her ass like they were possessed, and I picked her up and carried her out of the kitchen to my room. She laced her legs around my back, already kissing my neck.

I tossed her to my bed and landed on top of her. We made out frantically, and when she undulated her hips while rubbing against me, I nearly lost my mind.

“Need to do something first,” I said. I took my pajama pants off, then stripped her top and shorts off to reveal perky little breasts and a breathtaking pussy. She widened her legs and then spread her labia with two fingers to show me how wet she was.

I took the invitation and ate her out. She was tart and sweet, and her responses were incredible. As I fingered her pussy and lapped up all that wetness, she pinched her nipples. When I found the right force and rhythm, she orgasmed with a little stuttered moan that was the sexiest thing I’d ever heard.

“Now,” she told me, pushing my head away, “you know what I want.”

I retrieved a condom and the bottle of lube I optimistically kept in my bedside drawer. “The key to anal is to take it slow,” I told her. “And to lubricate a lot.”

I moved her to her hands and knees and widened her legs until the pucker of her asshole was revealed. She was perfect there, too. I licked it a few times while she squirmed, then I lubed up my fingers and started stroking over it. Periodically I dipped a finger an inch or so inside, letting her get used to the sensation.

When she was bumping her hips back against my hand asking for more, I slid my entire finger in. She was hot and tight, and I nearly short-circuited thinking about what that channel would feel like around my dick. I worked my finger in and out gently.

She sighed and rested her head on her hands. “This is way better than I thought it would be.”

“We’re only starting, sweetheart.” Satisfied that she was into it, I added another finger. She shivered and shifted uncomfortably, but soon enough she settled back down. In and out, in and out. I stared at my fingers and the glistening lube as they pulled out of her ass. It was my filthiest fantasy come to life.

“I want all of it,” she said, looking back at me. “I want your cock.”

Those words sent a jolt of pleasure through me. I reached for the condom, but she shook her head. “I want it bare,” she said, “unless there’s a reason we shouldn’t. I’ve been tested.”

“Me, too.” I stared at her upraised ass and the curve of her back, her wet pussy and wicked smile. Was this actually happening? Was I about to fuck my friend’s daughter in the ass?

Yes. Yes, I was.

I lathered my cock with lube while she watched with interest. Then I positioned myself behind her and placed the head against her hole. I pushed into her a little, massaging her clit as I did.

She hissed in a breath and tensed, so I stopped an inch in and focused on working that swollen little clit. When she relaxed again, I took a little more.

The more she took, the more she seemed to like it. Soon I was seated balls-deep in her tight, hot ass, and her pussy was soaking my fingers. She moaned and rocked on me, sending my dick in and out. She was fucking herself with me.

I felt like I was going to spontaneously combust, so I stilled her movements with my hands on her hips and took a deep breath to settle myself. When I was in control again, I started fucking her.

I went slow so she could get used to it, but she was soon begging for more. “Touch your clit,” I told her, planting my hands on the bed on either side of her. “Make yourself come.”

I fucked her hard in the dirtiest version of doggy style, relishing that tight ass that squeezed me like a fist. She moaned with each thrust, and soon the combination of my dick and her masturbation set her off. She screamed into the sheets.

A few more good thrusts and I came, shooting my load deep into her. Her ass squeezed me the whole time, like her body was milking every last drop I had to offer. When I pulled out, come trickled from her hole.

“Well?” I asked as we both collapsed. “Did you like it?”

“I loved it.” She grinned at me. “And now you’re definitely the hottest dad.”

Judge me if you want, but being in that ass was heaven. I would do it again and again. In fact, I’m going to — the next morning, Kirsten asked the other girls if sleepovers could be a regular thing.

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