By J.K. Jones
Emily’s hand in mine was smooth, slim and warm, and pulsing with life as she almost dragged me up the stairs to the second floor of her house. Her sexy ass was bouncing right in front of me, her legs long, smooth, naked. I could smell the heady aroma of a turned on woman, with a tinge of alcohol. Her hair was long, thick, and showed signs of recent brushing, less wild than ten minutes ago when she had come rolling in drunk and disheveled from a night of drinking with girlfriends and fending off creeps.
Emily turned her face as we arrived at her bedroom door, and her beautiful large brown hazel eyes flashed with lust and urgency. Pragmatically, I noticed that during the five minutes she had been upstairs, she had touched up her make up. So the act of letting her robe slide to the door to show me her fine, naked, aerobics-built ass and legs, and asking me if I wanted to go upstairs with her, as spontaneous as it had seemed, was probably something of a planned seduction. However, it had worked with acute efficiency.
My pants were almost busting out around my hard cock as Emily pushed me against the frame of the open door, her heated lips and alcohol-flavored tongue finding mine, kissing me urgently, her eyes closing, her hands passionately untucking my shirt from the front of my pants.
I looked sideways and saw the door of her son Jacob’s room; he was sleeping, maybe ten feet away from us. I was there in the first place because I had been babysitting him since early evening. “Let’s get inside your room,” I managed. Emily opened her eyes, saw where I was looking, and grinned.
We stepped into her room together, and closed the door. “I assume you are done charging me for your time?” Emily asked wryly, showing that lust and horniness didn’t diminish her sense of wit and humor.
“Nope, we’re into overtime now,” I told her.
“Just don’t tell me it’s the friends and family rate,” she said. I winced at her joke, but it was solid, since we had been making incest jokes earlier, although far more innocently.
I started to say something back, but she dragged a finger across my lips. “Shhhhh,” she said. “I’m naked, and you’re not. I need that cock out and in my mouth right now, and you need to shut up and let me suck.”
Who was I to argue? Emily slowly dropped down, kneeling in front of me, her wide eyes looking up at me with lust and expectations. I fumbled with my Levi 501 snaps, but finally got them apart, and pushed my jeans down my muscular legs. My cock snapped out, already fully hard, plopping on her tongue, which she had stuck out to catch the moving dick. Emily grabbed it with a small hand, and begin flicking her hot tongue around the shaft and head of my cock, slathering it with spit like a pornstar cumslut. I gasped for air at the sudden shock of having my cock pulled out and slurped upon by this beautiful older woman. Then it got even more intense when she decided to slam it into her throat, and push it down the back of her throat. I heard her retch and gag a little, but then she stopped, and looking down I noticed her nostril’s flaring as she breathed through her nose, her open mouth, lips and teeth crammed fully against my closely-cropped pubic hair Emily’s beautiful eyes bugged a little as she pushed her face against me, my cock completely engulfed down the back of her throat. I barely noticed when one of her fingers pushed at my butthole, the nail and the tip slowly pushing with delightful pressure into my ass. After a moment Emily pulled back, gagging a bit, and with a heavy breath she looked up at me, spit still connecting my cock to her slutty mouth. “Girls your age know how to do that?”
I mewed and shook my head. Her finger slid into my ass, up to her first knuckle, I think. Her other hand gripped my dick and stroked it expertly. “Don’t try to hold it,” Emily said. “I want you to blow your load into my mouth. I want to fucking eat that cum of yours.”
“But what about,” I started, but her head shook and she growled up at me. “Shut up Jay, and let me run things tonight. You are going to fuck me all night, eat my pussy, and probably piss all over me. You are definitely going to fuck my ass and you might be licking it out afterwards. But right now you are giving me your cum. Got it!”
Not in a thousand years would I have managed that this slick, cool customer, this aloof, friendly but disinterested woman, who I had babysat for numerous times without incident, would have somehow become a sex crazed freak. But she had fully morphed into an aggressive cum-seeking slut, and I was at her mercy. Emily’s fist began to blur as she stroked my cock, alternating between licking the head with her hot, wet tongue, and then looking up at me and saying nasty things like “Shoot your cum in my fucking mouth, you fucking stud,” and “I’m your fucking cum dumpster, and I need you to fill my mouth with your load.” And then she would go back to licking my head. At one point she skillfully inserted the hardened tip of her tongue into my dickhole, and I felt something in a place I’d never felt anything before.
I could feel Emily’s lean, soft body pressed against my bare legs, her tits against my thighs, hands on my ass, and a finger in my butthole. Her fist pounded on my cock, and her hot tongue was slathering at its head, and then it was all too much for me, and I began cumming. My legs shook, my fists knotted up, my jaw quivered, and with a huge groan I began shooting streams of cum at Emily. Obviously this was not her first rodeo. Emily skillfully pointed my cock at her tongue, taking my first vanilla dollop on her tongue, and then she moved forward, engulfing my cock and sucking at full power, adding to the intensity of my orgasm, even as cum dripped down the side of her mouth onto her left shoulder and one of her perky tits. I shook a little longer as the jism stopped spurting out of me, and Emily leaned back just enough for maneuvering room, and began to dutifully lick my cock and then my balls. She popped the finger out of my butt, and made sure I was watching as she put it in her mouth and licked it off.
My eyes widened as I gazed down on a completely turned on cumslut, something I had not until this moment in my young life, had the good fortune to do. “Turn around, Jay,” Emily said in a throaty voice. “I want to rim your ass.”
I was done arguing. I turned and faced the door frame, leaning against the cool wood. “Push your ass toward me Darling,” said Emily. I did what I thought she was asking me, and felt her body against the back of my legs, her hands on either ass cheek, slowly pulling them apart, and then air on my exposed butthole. Then, and even decades later, I remember this perfect, I felt the wet, hot tip of her tongue slowly push into my ass. Her breath played down over my taint and balls, and then she was pushing her face as far into my spread ass as she could get, sticking her tongue out as eagerly as she could manage, and inserting it into my ass. I just moaned with pleasure. After what felt like a hundred years of the best thing I’d ever felt, she pulled back, popping her tongue out of my asshole.
“Oh my fucking god,” I said, turning back around. My cock was already hard again.
Emily stood up and put a hand on my neck, pulling me close, and slamming her tongue into my mouth. I didn’t taste anything horrible like I expected. “I like ass,” she whispered to me. “Eating it and getting fucked in it.”
“I’ve never done anal,” I admitted.
“Really? So you are kind of a virgin after all, Jay?”
“I guess,” I said.
“You are going to fuck my ass right now,” she decided. Emily took one of my hands and led me over to her bed. She slid onto the comforter, skittled up onto the bed, and spread her legs. “I’m wet as fuck. I’m going to use it to lube my ass. Watch this.” She slid three fingers into her pussy, using the other hand to spread and hold her lips, and pulled out a dripping wad of cunt juice. Without hesitating, Emily pulled her legs farther apart, lifting them out, her hips rotating, showing her pink asshole, and then slid the three fingers into her own butt, pushing around the juice.
“Normally you fuck cunt before ass,” she said. “But I want your first fuck with me to be right into my ass. We can do the pussy cumming later tonight. Come here.” I got up on the bed, having stripped off the remainder of my clothes, basically my shirt and socks. My cock was jutting out.
Emily guided me to kneeling position between her slender, splayed legs. The head of my cock plopped against her wet, shaven pussy as I jostled into position. “Nope, not there, my love,” she grunted, and with soft fingertips guided my dick lower, and then pushed it against her butthole. “Now, slowly push it in my ass,” she breathed, looking up at me with lusty eyes. My dick pushed against her pink starfish, opening it up, appreciating the pussy juice lube coating her rectal flesh, and then I slowly inched my rod into her tight wet butthole. “Oh god yes you ass fucker,” she grunted, her hands moving up to my shoulders. I hit her body with mine, fully inserted into her ass. I pulled back and out a few inches, and then sank it back in, and then began slowly fucking that tight round shit canal of hers, while she began shaking her head back and forth with pleasure. Her fingers were a blur at her clit region, and she humped back at me as I held myself up with my arms and began slamming into her tiny moon shaped ass. She grabbed a small pillow and bit it hard to keep from screaming, and then she began cumming on my ass-buried dick, shuddering and spouting unintelligible nonsensical mutterings through the pillow. Finally she stopped making noise and stopped moving, and just collapsed there.
I didn’t know what to do. I pulled out of her ass, watching it slowly close up. Looking down, I could see I was a little dirty on the end of my cock. Also, I could suddenly smell it.
“Bathroom is over there. Go clean yourself,” she whispered. “Use soap.”
“OK, and then you want me to go?” I asked, as I got up, unsure.
She giggled, and pulled the pillow off her face, and looked up at me. “Do you want to go? Or would you prefer to fuck me for a few more hours?”
“I’ll be right back,” I told her.
“Thought so,” she laughed. “And bring me back a soapy washcloth so I can wash my ass.”
As I stumbled into the bathroom, Emily was suddenly beside me, her hand on my ass. “Never mind, I need to clean up too. Let’s just hop in the shower.” She reached into the double headed, glass walled shower cubicle, and got the water going. She turned and looked at me. “You doing okay, love?” I glanced over at her, standing beside me, her beautiful slender legs joining at a swollen pink shaved cunt. I saw a trail of pussy and ass juice marking the inside of her leg. Her tits were swollen, and her face was red, with makeup a little smeared. But she was grinning ear to ear.
I nodded. “I’m good. I got some poop on my dick. Which was weird.” She giggled, and slid a hand over my cock and pulled me into the shower with her. She reached for soap, and began covering me with suds and foam.
“We’ll have you cleaned up in no time, and me too. Sorry about the shit. Usually when I do anal, I use an enema first and clean myself out. Obviously, tonight wasn’t planned.”
“It’s fine. It’s no big deal I said.” Emily rubbed and scrubbed me, her hands all over me, and within a very short time my cock was pointing at the ceiling again. “Now you do me,” she said, handing me the soap and turning around, offering her ass for me to scrub. I did due diligence on her butt, scrubbing it all over vigorously, but especially the crack. “Clean it good with your finger,” she breathed, leaning back against me. I slid a soapy finger into her butt, while I soaped things up.
She turned and started kissing me as the water cascaded over our shoulders. “I’m glad body functions don’t freak you out,” she said. One of her hands was rubbing and slowly jerking on my hard cock. The other reached behind her, and turned off the shower. Emily slowly dropped to her knees, and began to tap my hard cock against her cheek, while she looked up at me.
“Ever peed on anyone?” she asked, eyes open and connected with mine. I shook my head. She scooted back and looked up at me. “Do you have to pee?” she asked.
“Yeah, actually I do,” I said. “Good,” she responded. “Just hose me down. Start on my tits.”
“You like it?” I asked, a little shocked. She flashed me a slutty, nasty smile. “Oh yeah, I am a little piss whore. Couldn’t you tell?” I didn’t know what to say.
“So lets have it, babe. Gimme your hot piss.” I took a breath, relaxed a bit, and then began pissing, slowly at first, but the stream of hot gold pee showered out, splashing off her tits. Emily moaned and rubbed her nipples, and then lunged forward, mouth open, catching a mouthful of my pee, gargling it with mouth open. I heard the water splashing in her open mouth and watched it flow down all over her, and then she moved her head again, catching my piss on top of her head, down her lovely dark, wet hair, and then she was moving her head again, and her mouth closed on my cock, and she was gulping down the last of my piss, her eyes closed, a look of serene ecstasy on her face. A moment later, she lay back on the shower stall floor, her legs spread, and pulled me on top of her, slipping my hard cock into her gushing wet cunt. She was sticky and tasted salty as I kissed her piss covered face, and I was slamming my rigid dick in her tight pussy. My balls slapped against her ass cheeks, and she was playing with my wet hair, and urging me to fuck her harder. It did not take long for both of us to climax, and I grunted like an animal as I unloaded a massive eruption of white butter into her stretched cunt, and she quivered with her own orgasm as I unleashed a cup of jism into her slutty body.
Eventually she reached up, and turned the shower on again, and the two of us stood up and, rather chastely, scrubbed the piss and cum off of each other. Then, after drying each other with nice towels, we fell into her bed and had one last, much more loving and kissing and romantic- type of fuck.
I scooped up my babysitting money and was out of her house by 6 am the next morning, after about three hours of cuddling and falling asleep and then waking up with morning wood, which she sucked to another mouthful of tasty crème.
As I skateboarded back toward campus, smelling the brisk morning air, and reflecting on all of the crazy, freaky shit I had done with this incredible woman, I wondered if I was going to see her again. The babysitting was a gig I didn’t want to lose. And the fucking!
In fact, we met for coffee later that week, and I discovered that after having broken through the cool shell of diffidence she had previously projected, that she didn’t need to be drunk as a skunk to want more of me. “As long as you don’t tell anyone, I’d like you to come over and fuck me a couple nights a week.” She whispered over her coffee, looking around the coffee shop to make sure we weren’t overheard. “And honestly, there is more kink I want to do with you.”
I sputtered into my coffee. “Really? Like what?”
She smiled mysteriously. “You’ll just have to wait and see.”
Source: reddit.com/r/Erotica/comments/dq6f27/upstairs_a_milf_fantasy_part_ii_serious_fucking
Link to this story on my blog: https://onehandedstories.com/upstairs-a-milf-fantasy-part-ii-serious-fucking/
This is Part II. There are 5 parts, and each one gets a little freakier.