I’m not sure if this is against any rules. I loved [u/filthhunter69](https://www.reddit.com/user/filthhunter69/) ‘s story below and wanted to expand on it. [https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/](https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/)
******
“Oh my. That was fantastic,” my mom sighed as she set her paperback novel on the table. We were sitting on the back deck of our home on a warm May afternoon. I had just graduated college and had no idea what I was going to do with my life. The job market wasn’t exactly hopping with opportunities as it is. And I’m a political science major, for fuck’s sake. I just choose to not think about the decisions I have to make until I have to.
My mom picked up her phone. I knew she was calling her friend Carol.
“Yes, I just finished it. It’s so good!” Her eyes brightened as she listened to Carol gush over the same trashy novel.
“Oh sure! She can come pick it up this afternoon. I may not be home but Jeremy will be here. I’m sure he’d love to see her. Okay. Bye.”
“That was Carol. Kathleen is going to come by this afternoon and pick up this book.”
Kathleen Anderson. I’d gone months without as much as a passing thought about her. She may have been my mom’s best friend’s daughter, but we barely knew each other. She’s just one of those kids you know growing up. But unbeknownst to me, I was just a couple hours away from fucking her in the ass.
While we were the same age and our moms spent countless hours together, we never got close. She always seemed to me like the quintessential good girl—a bookworm taking after her mother, and slightly nerdy. I’d seen her only a few times since high school, never exchanging more than a few awkward pleasantries on those occasions. She was just so quiet and boring.
“I’m visiting Helen and it’s a pretty long drive,” Mom said. “I’ll only be back late. If Kathleen comes by, just give her the book. I’ll leave it on the kitchen counter. Oh, and tell her I said hi.”
Sure. After Mom left, I cracked open my third beer of the day. You could argue that I should have been spending my time looking for a full-time job, but I had my parents’ roof over my head and enough random projects to provide me with spending money. The real world could wait a few more weeks.
About an hour later, the doorbell rang. Still on the back porch in my gym shorts and dry-fit T-shirt, I weaved through the house to see who was at the door. There was Kathleen, smiling as she tucked her sunglasses in her long black hair.
“Oh, hey Jeremy!” she said with excessive cheer. She was wearing a bright yellow and white sundress that was really striking even in the late afternoon sun. “I’m here to pick up a book— Sorry, I meant ‘the’ book”, she adds, theatrically rolling her eyes and raising jazz hands for emphasis.
I was slightly caught off guard by her chirpiness. She may have looked like the Kathleen I knew, but her demeanour was completely different. Instinctively, I reciprocated her tone and cheer.
“Hi, Kathleen! Wait, you’re not referring to ‘the’ book, are you? The one I’ve only heard about a million times?” I said, squinting my eyes at her. This brought out a geeky laugh from her, showing the upper row of her perfect teeth.
“You know it!”
I invited Kathleen inside. As she crossed the threshold, with her dress flowing behind, my eyes were drawn to her smooth toned legs. She was definitely curvier than I remember. As a teenager she wasn’t much to look at—tall, lanky and awkward. I was impressed and maybe even a little turned on to see how she’s blossomed.
“How’s your summer going?” she joyfully asked. In most cases, chipper people bug the hell out of me, but there was something about Kathleen’s happy personality that felt so genuine that I started to warm up to her. And I have to say I was really beginning to dig her smile.
“It’s going pretty well. I’ve got a bunch of odd jobs until I start finding a real one. I’m going to start caddying at Falcon Valley next week.”
“Falcon Valley”, she said with slight disdain. “My boyfriend’s family practically belong there. Well, ex-boyfriend anyway. Fuck him.”
I raised an eyebrow. I didn’t think Kathleen Anderson even knew any swear words. Perhaps she was no longer the goody-two-shoes I took her for. How did I not get to know this side of her before?
We chatted briefly about her plans for the summer: having studied accounting and finance, she’ll be keeping the books at an Italian restaurant.
“I freaking love their clam fettuccine,” Kathleen said wide-eyed. “If I can’t learn to cook that, maybe I’d learn to cook their books.” The intensity on her face evaporated and there was that smile again, pearly whites and all.
“Ha!” Suddenly I found myself grinning like an idiot. “Careful, though. You might find yourself sleeping with the shellfish…es.”
Kathleen chortled.
“Fuck me, that was terrible! That was so, so bad,” she says. She covers her mouth as she stifles a giggle, her shoulders bouncing up and down. I can feel my cheeks flush from embarrassment; it had sounded better in my head. She then looked up, taking a deep breath. I focused my attention to her neckline: following the well-defined lines of her clavicle, down to the beginnings of her ever so slight cleavage.
Kathleen gathered herself, resting her elbow on the kitchen counter behind her. She noticed the book sitting on the counter.
“Oh wow, so this is it, huh?”
“The one and only,” I said, as I walked towards her.
“Let’s see,” she said as she turned to face the counter. On the cover of the book, there was a woman writhing in between sheets with a euphoric look on her face. Kathleen gingerly positioned herself in front of the barstool. Her hands then swiftly smoothed the back of her dress as she sat down. I love it whenever girls do that; it’s such a simple, innocent move but such a turn on. And I was close enough to see the shape of her ass—it’s definitely a little bigger now—and perhaps the lines of her panties.
She turned to face me and said, “I just don’t understand why our moms love this trash so much”. Her back was arched and her arm pressed against her breast, accentuating her cleavage. I stole a glance. It dawned on me that not only was I checking her out, I was smitten by her smile and bubbly personality. Am I crushing on her?
“It makes them happy, I guess. They get to live out their fantasies,” I said. “They get to go to all the places they haven’t, be people they aren’t.”
“Jeremy, that makes it way worse,” she snaps back. Her face was serious, her eyebrows furrowed. “I choose not to believe that because it’s like they regret who they’ve become. And fantasies? So they want to sleep with other men?”
“Whoa! All I’m saying is that it’s just fiction. It’s an escape. It’s not deep-seated regret about everything and anything!”
“I can’t do regret. God, I couldn’t even master Spanish after four years in New Mexico and I’m literally kicking myself.”
Suddenly, Kathleen went quiet. She buried her face in her hands and let out a tired sigh.
“Did you do everything you wanted to before you graduated?” she asked, pouting as she put the book in her purse.
“Hmm, obviously I have a few,” I replied. “It’s not just Spanish for you, is it?”
“You think I’m overreacting because of the book, don’t you? Compare notes with me then.”
“Huh?”
“You know, compare lists of anything we didn’t get to do yet. Then if anything matches, we can do it together. We have an entire summer, don’t we?”
Her idea struck me as odd. We’d never even hung out before, and she’s just assuming I’d want to spend the summer ticking off lists with her? Silly idea aside, it was a pretty decent prospect for me, especially as I looked at her then.
She went on about not wanting to one day be a fifty something unhappy with who became, living with regret and having to resort to reading trashy novels to live vicariously as a fancy ass spy having steamy trysts in exotic places to please her unfulfilled desires.
“Come on. It’ll be fun. Pleeeease?” she said, as she tucked a lock of hair behind her ear. Oh, for fuck’s sake. I tossed her a pad and pencil from the kitchen counter.
I scribbled down my list. I wrote that I wanted to finish watching all James Bond movies, start drinking wine, that new thing better than platinum on Reddit and a few others. My last item was intentionally designed to get a reaction out of her. ‘Fuck a girl in the ass’. Now that would make a pretty good unfulfilled desire for a fifty something! I figured at worst she’d be offended and drop it. At best, she’d laugh and reveal herself to have a better sense of humor than I thought. And maybe we could hang out…
We exchanged lists. I scanned hers quickly. “Smoke pot, skinny dipping…anal sex.” Holy shit! I didn’t expect her to mess around and I sure as shit didn’t expect this. I looked up to see Kathleen’s eyes bulging as she reviewed my post-graduation to-do’s.
“Looks like we have a match,” I said with a sinister chuckle.
“Did you peek at mine when you wrote yours?” she demanded.
“Nope, I was busy recounting the James Bond films I haven’t seen.”
“So you’re serious?”
“Yeah. Previous girlfriend didn’t enjoy when I put a finger in there.”
“Then I suppose we do have a match,” she replied, nervously nibbling on her fingernail. “I tried a inserting a finger while masturbating. Curiosity. Now I wanna try the real thing.” Both of us stood frozen, just a couple feet from one another. Neither of us knew what to say next.
Suddenly a wave of confidence crept across Kathleen’s face. She looked up at me, bit her lower lip and smiled.
“I’m ready if you are,” she said, grinning seductively. Her hips swayed gracefully as she got off the barstool.
I smiled and edged towards her, nervous as hell but we did have the house for the evening. I stepped towards her and placed one hand on her back and another on her face.
“Kathleen, never in a million years would I—”
“Shut up. Do not start,” she cut me off before she started laughing and went in for a surprisingly aggressive kiss, full of tongue.
As we made out, I ran my hand down her neck, all the while feeling our breaths long and heavy on each other. Slowly, I traced along her shoulder to her clavicle. The kissing got even deeper as my hand went further down, cupping her breast and squeezing it gently. Even under a padded bra I felt how firm it was. She let out a soft moan and a chuckle.
“You totally sneaked a peek earlier.”
“Sure. But we’re not here for that, are we?” I said as I lifted up her skirt. I caressed her smooth thighs, moving upwards and then settling my hands on her ass. They were just right—firm yet soft and with a slight jiggle. I put my hands under her panties and started kneading her ass.
My dick was getting pretty hard by then. She was now kissing my neck and running her hands down my chest towards my groin. Abruptly, I pulled away and grabbed her hand.
“Bedroom. We’ll need lots of lube. Trust me. I think I know what I’m doing,” I said as I led her up to my room.
“Well that’s reassuring.”
When we got to my room, I quickly fished out a bottle of lube from a drawer. While I was bent over, she pulled off my shorts from behind, leaving me bottomless. Kathleen then poked my asshole.
“What the fuck was—!”
“I wrote ‘anal sex’. I didn’t say it had to be *my* anus,” she said matter-of-factly with the most cunning of grins. She held out her middle and ring fingers, as if ready to lube up and looked at my ass.
My jaw dropped. What did I sign up for? Like fuck will I want anyone going at me from behind.
Kathleen started laughing hysterically. “The look on your face is priceless!” I breathed a massive sigh of relief and joined in nervous laughter.
“But seriously, if you’re worried about the *possibility* of something going up yours, think of how I’m feeling now,” she said. Clearly she’s done a bit of thinking about this. “Go easy on me, please.”
“Of course,” I said, spinning her around and pulling her close. I hugged her from behind and lifted the dress off. Her sunglasses, still in her hair, fell to the carpet. Before she could set her dress aside, my hands were already busy squeezing her breasts. I bit on her bra strap, pulling them slowly off her shoulder before repeating the other side.
Kathleen was giving out light playful moans by then. She reached out a hand behind, blindly searching for my erect member. Finally grabbing it, she began exploring its entire length.
“Looks like you’re ready to go,” she said. My stiff dick popped free like a spring. Kathleen simply mumbled “fuck,” as she handled my dick. First she worked her way up, thumbing the tip, then back to the base, grabbing my balls and brushing my pubes.
I unclasped her bra and threw it to the side. Peering over her shoulder, I could see the puffy nipples atop her perky breasts. I twiddled with them between two fingers on both hands. She leaned backwards into me, gripping my dick harder and guiding it deep into her butt crack. I could feel the firmness and warmth of her buttcheeks on my throbbing dick. She then clenched her ass and pulled up the band of her panties, catching me by surprise by squeezing my dick from the sides and below.
“Fuck!” I yelled, a little higher-pitched than I would have preferred. She released, and turned around to face me—this time her smile a devilish grin.
I grabbed and sucked on her breasts. I could get almost half of one in my mouth, sucking on it hard and nibbling on the nipple before swapping sides. She ran her hands all over my head, messing up my hair, but it was a massive turned on for me, as I latched onto a mouthful of boob.
Kathleen slowly pulled away from me to sit on the edge of the bed, finally getting a proper look at my dick. She held it in her hand, studying every vein and mark on it then licked along the shaft. My dick twitched at the warmth of her tongue, bouncing in her hand and catching her by surprise. She let out a giggle.
“Maybe we can get you wet enough that we won’t need the lube,” she says absentmindedly.
Once she was ready to take it in, she lifted my dick to her mouth and took a deep breath. Her breasts jiggled a little, as if calling for my attention. I dutifully massaged them and pinched her nipples, eliciting a slight quiver from her.
She licked off some precum and spread it all around the tip—her tongue going a full circle around. I let her know I loved that by pinching her nipples harder. She then went the opposite direction, acknowledging me. That tongue was pretty damn crafty and she knew how to use it. Our eyes locked as she started bobbing her head forwards and back taking me in entirely. Fuck, that was so hot.
Kathleen went at it for a while until I could feel my dick drenched in her spit. She was happily trudging along, with her hair a terrible mess. I tucked some behind her ears but decided to make a ponytail instead and pull her head up. She bit the edge of my T-shirt and pulled it up with her. I let her take it off me, finally letting go of her hair. She was then kneeling on the bed, face-to-face with me. I reached in for a kiss.
“That was fucking incredible,” I managed to say, muddled up in her spit and heavy breathing. “Now turn around and show me your ass.” Her eyes gleamed at that and again that smile.
“Glad you were loving it,” she said in a sultry voice. She turned and got on all fours, wiggling her ass at me. “What are you waiting for?”
I took her sandals off and smacked the lovely ass before me. She let out a loud yelp and a giggle. I playfully bit on her ass and sucked on it deeply, leaving a mark. I ran my fingers on her panties, along the band, then along the gusset. But I didn’t pull it off yet. I bent down and sucked her toes, moving swiftly up, licking her feet, legs and thighs. Then I went back down to her other leg. Through her legs I could see her eyes were shut, mouth agape. She was moaning softly, one hand squeezing a breast, the other grabbing a handful of my sheets.
The deal was anal, but I was enjoying this too much.
As I was kissing and lightly biting her thigh, I noticed the musky odor from her pussy. I started to sniff on and around the gusset and gently nibbled on it. Her moans grew louder.
“I hope you taste as great as you smell,” I tell her as I hooked my fingers around her white cotton panties. She shook her ass in reply, jiggling it slightly. I pulled her panties down to her knees, revealing her puckered anus and a bit of cloudy grool stretching out from the tidy line that was her innie pussy. I spread her pussy open with two fingers and then rubbed her glistening wetness all around. She twitched as I touched her clit.
My tongue licked a straight line from her clit, up along her pussy, tasting her juices. It was intoxicating: musky, briny, yet sweet all the same. And extremely sticky. This is the best part of sex, for me—deriving pleasure from getting a woman off and tasting her arousal, knowing you did it right. My face may have been buried deep in her ass, but in my head I was in heaven. I wanted to lick up every last drop of her.
But I still remembered our anal deal. Her balloon knot was, after all, inches away from my eyes, just staring back at me quivering every now and then, wanting attention. I moved my tongue higher up, rounding out her pussy at the perineum, and scooping up some of her grool to her anus. With a renewed enthusiasm, I started licking circles around it and then making sure my tongue covered every tiny fold of it. By the quivers of her anus, I could tell she was enjoying it.
“Mmmmm,” she mouths and bites her finger.
I then turned her over, lying on her back, so I could take off her panties. Interestingly, she had a decent bush. It was manicured into a neat little triangle just over her mound. The hairs were long enough that I could twirl them with the tip of my fingers. And then I went to town licking her sweet pussy.
“More pressure” she orders. I put my middle and ring fingers in her pussy and started rubbing her G-spot while sucking on her clit.
“Oh, right there. Right there! Yes!” Her moans gradually speed up and she starts to pull my hair, jerking my head this way and that.
I used my pinkie finger to massage her asshole, taking a leaf out of her book by making circles around it then reversing direction. After a while, the pinkie gets in; a proper 2 in the pink, 1 in the stink. I keep at it—sucking on her clit and using 3 fingers—until her back begins to arch and she lets out a long, groany “ahhhhhhhh!”
I moved away for a better view of her pussy quivering, with each pulse of her orgasm, it strung along her puckered asshole.
She quickly got up and pushed me on the bed. Straddling me, Kathleen lowered herself on my dick gently. I savoured the moment as her warm, velvety pussy enveloped firmly around my dick, a firm grip all the way down to its base. Then she pinned her hands on my chest and started gyrating, her loose hair framing the soft jiggle of her tits. I kept myself busy, pinching her nipples and rubbing her clit every so often. She then reached down for a kiss and I grabbed her, thrusting from below a couple times before I gave up. She looked at me and I nodded.
We got back in the doggy position and I fingered her from behind. I let out a big gob of spit on her anus, letting it slide down before spreading it around with my thumb.
“Ooooh,” she exclaimed, pleasantly surprised but also slightly tinged with fear. I tried to get my thumb in but she was still too tight.
“Hey, just relax. Don’t tense up,” I said, trying to sound reassuring.
“I’m trying. Slowly, please,” she says, muffled by a pillow on her face.
I applied a generous amount of lube on my thumb and on her anus. She shivered a little as she came into contact with the cold gel. I rubbed circles with my thumb and firmly pushed through as she groaned.
“Okay,” she said, giving me a knowing look and nodding. Once my thumb was about an inch inside her, I started clamping my fingers and thumb. It was an odd sensation: my two fingers in her pussy could feel my thumb up her ass and vice versa. I kept at it, until she started moaning loudly and reached out a hand to rub her clit. Within seconds, she was cumming hard, letting out bursts of shrieks into my pillow.
I pulled my 2 fingers out of her pussy, but left my thumb inside her. She was looser now, so while she recovered, I lubed up the 2 fingers and gently put them in her asshole. She yelped and her hand immediately shot back trying to push me away, but I had already got both fingers all the way in. I kept it there until she got used to it and her hand fell away.
“Is this good?” I ask.
“Yeah… It is,” she calls back, surprised at herself.
“And how do you like it now?” I queried as I poured a bit more lube and slowly pulled both fingers out a little. Her asshole had such a powerful grip, she was practically pushing them out. I went back in. Then out. And in. And again until I got to a steady motion.
“Oh fuck, fuck, don’t stop,” was all I needed to know to go on.
“You love it, don’t you, Kathleen?” I wasn’t one for dirty talk. In fact, I was always quiet when it came to sex. The dom and daddy talk always seemed off-putting to me. But seeing someone I had expected to be so vanilla, bent over like this, begging to be assfucked—I can’t help but feel an overwhelming sense of power and control of her. She needed something and right now only I could give it to her. But I was also astonished at her transformation over the years. “I thought you’d grow up to be boring; a librarian, perhaps… Yet here you are begging for it up your ass.”
After a few labored breaths she yelled out, “Yes! Yes!” Another couple breaths, “Yes! I fucking love it! Just shut up and go already!” Having been staring at her lovely ass bouncing and jiggling all this while, and knowing how much she wanted this—it was such a turn on for me. It all got to my head, and at that moment I knew I just had to. I spanked her ass so hard the ‘thwack’ echoed, like I’d seen in a thousand pornos before. She yelled out so loudly, the neighbours could’ve heard that. My hand left a mark. She looked at me incredulous, face as red as her ass, and her eyes wide with fear.
But she never said to stop so I went again and she yelled even louder.
“Think you could fit my dick in your tight ass?” I didn’t recognise the person who said those words.
But Kathleen yelled out an emphatic “Yes!” She reached her hand back and started stroking my dick, sliding it up and down her pussy and grinding it slightly when it reached her anus. I started to lube up to seal the deal. I was about to fuck Kathleen Anderson up the ass. We’re both about to try anal for the first time. She propped herself up on the bed’s headboard.
Pressing my dick against her anus, she whimpered with the nervous excitement that accompanies new sexual experiences. She looked back at me, her smile conveying a sense of determined eagerness. She ruffled her now messy hair and then began fingering her pussy.
“Ready when you are, tiger,” she said with such confidence. With our eyes locked, I pushed my dick inside her. She trembled and gripped the headboard firmly, grunting with pleasure as I pushed further. The tight grip of her firm ass around my dick sent shockwaves through me beyond anything I had ever experienced.
“Fuck, your ass is amazing!” I blurt out as I build to a steady motion.
“Fuck me, Jeremy,” she cried. “Fuck my ass!” Our hips moved in unison. She thrust her body back towards me to meet every push I gave her.
We rocked back and forth with a pace that continued to build. With my hands on her hips I could feel the orgasm growing inside me. I steadied myself. Our delighted groans filled the room and I could say nothing more than “oh shit!” as I exploded in her ass. She squealed with excitement as I pumped out every last drop.
Sliding my slick dick out, my fingers returned to her aroused clit. She was so excited that only a few seconds of pressure pushed her over the edge as well. Unlike the previous two, this one was one long orgasm. Her yell was somewhat muffled as one hand covered her mouth and another sank its nails into my thighs.
We both collapsed on each other.
Laughter accompanied our attempts to recover. I was too stunned and drained to say much of anything. I just lay there, wiping the perspiration from my forehead.
Kathleen lay on her side, head propped up by an arm. She watched me dwell in my post-coital stupor. She connected beads of sweat on my body with her finger, smiling while enjoying her own bliss. I ran a hand along her side down to her hips, feeling her body slick with sweat. After a while, she shifted her gaze at the claw marks on my thighs.
“Oh shit, I’m so sorry about that,” she begged, sitting up. “I got carried away and—.”
“Shut up. Do not start,” I said, smiling, motioning to the red hand on her ass. “It was hot as fuck, Kath. And it was stupidly intense. It was unbelievable.”
She rolls on me; her sweaty breasts brushing against my ribs.
“I came a bit too early, though,” the disappointment in my tone evident. “Would’ve loved to feel your ass contracting while I had my dick inside you. You’d probably rip it off me.”
“Ha!” she exclaimed. “We can always plan another round. Perhaps throw in a movie? What do you think, Mr Bond?”
“Oooh, but we’ll have to keep the volume down,” I quip.
“—of us, or the movie?” she asks with a wink and her teethy grin. I’ve definitely fallen for her now. “Oh, but promise me one thing.”
“What’s that?” I ask.
“No more lame puns,” she says curtly.
“What? Why?” I demanded. “You didn’t think it was fant-ass-tic.”
“Oh, for fuck’s sake!”
Source: reddit.com/r/eroticliterature/comments/gq5eed/a_fantasstic_gamble_mfanal