Upstairs –A MILF Fantasy – Part III – “Emily and her Friends”

By J.K. Jones

At the tender age of 19, I’d had a few sexual encounters with girls my age or just a bit younger, and had even gotten a hand job from a teacher’s aide, a 24 year old grad student named Sheila, one day after class in her tiny office. Long story, and one that involved three hours of flirting over coffee, and a wager, but I’ll tell that one another time. My point is that I had so far had some mild level of sexual adventure by my junior year in college. I was tall, not bad looking, had a body hardened by bicycling and tennis, a good-sized cock that was always popping up and out. I had straight teeth, (thanks to braces in middle school) an agile mind, and because I liked people I tended to talk to them. One secret that many kids my age hadn’t yet figured out, but I had, was that if you spend some time and effort talking to a lot of females, you are going to end up fucking some of them.

So I was not a naïve virgin when I met Emily. But holy cow, I sure felt like one. She was like no one I had ever met or could imagine. Tall, slender, with dancer’s legs, a lean cat-like torso, lovely medium sized breasts, a model-gorgeous face with an upturned pixie nose, wide beautiful eyes, sculpted brows, and a full head of wavy, curly hair hanging down all the way to her shoulder blades. She was elegant and aloof and unattainable, a gorgeous but quite diffident thirty-ish woman. She had a nine year old nerdish son named Jacob that I had been babysitting a couple times a month while she went out and about. Jacob was fun, like a little brother, and after watching a movie or anime with him, I’d tuck him in and have a few solid hours to do homework, while being paid a babysitter’s wage. All in all, a splendid gig for a college student.

I’ve already written about the night Emily came home drunk, disheveled, lonely and horny, and in a whirlwind three or four hours, how she seduced me, enticed me to join her upstairs, and then offered her ass to my cock, popping that particular cherry, and then in the shower, how we fucked like animals, covered with the intimate stickiness of piss and cum. After cleaning off, we slept together that night, fucking again in a more normal way, both in choice of which hole in her body I slid into, and position (missionary). We dozed fitfully a few hours, and then early the next morning, she sucked me hard, rode me to a quick O for herself, then blew me lovingly until I popped again, in her wet, wonderful mouth.

We had coffee a few days later. I was really nervous meeting her to discuss “us,” as she had said on the phone. I was worried that I had lost my babysitting gig, but even more nervous that she would freak out about what had happened, and I would lose her friendship, contact with her, everything. My nervousness faded when she saw me, already sitting at the table when she walked into the shop. I got up to greet her, and she pushed close and gave me a kiss on my lips. “Hi hon,” she whispered. I had already gotten her a cup of coffee, which she noticed, smiling at me. “Thanks. You are so thoughtful.”

We ended up talking about a lot of things, and I won’t bore you with the exact conversation, but a summary would be that Emily didn’t want to lose me as a babysitter, and she’d like it if we continued to have fun in the bedroom, as long as Jacob didn’t find out, and I wasn’t going to talk about it with others. That sounded good to me, and as we parted outside the coffee shop, she hugged me close, looking around to make sure no one was paying attention to us, gave me a short kiss, with her tongue flickering into my mouth, and quick squeeze of my cock, which was, of course, half bulging through my pants. “Friday night. 7 o’clock. I’m going out with my girlfriends again, Won’t be too late though. I’d say if you get Jacob to bed by 9, he should be out by 10. So you’ll see me about 10:30.”

She was so logical and pragmatic with her planning! But so was I. “Good. That will give me an hour and a half to finish a chapter of Chem.” I told her. “What do you have planned for after you come back?”

Emily giggled and raised her eyebrows as she backed away. “Wouldn’t you like to know!” Then she turned and sauntered away, her ass just smackably fine in her blue summer dress.

And so I found myself sitting at her kitchen table on the next Friday evening, the Chemistry chapter half done but with no chance of being finished tonight. Distracted, I looked up at the clock and saw it was 10:40, just three minutes since the last time I had looked. I had already checked up on Jacob, who was zonked out and was not going to awaken until morning. I was wearing tight blue jeans and a white T shirt which showed off my teen pecs and rippling arms pretty nicely. I looked down at them, and wished they were covered with sleeve tattoos, but they weren’t. Too bad though. Ladies loved the sleeve tattoos. My mind was zipping through ideas and patterns for a tattoo when there was a noise at the door, a rattle of the knob, and giggles from the outside.

Expectantly, but trying to remain nonchalant-looking, I picked up my pencil as if I had actually been working, and looked over as the door opened.

Pushing her way through the door, hips swaying, her steps a little drunk, was a beautiful, skinny long haired brunette with flashing eyes and bright lipstick. She was tall, slender and tanned, with wavy dark brown hair down her back, wearing a coral party dress over her slim form. And although she was similar in many sexy ways to the woman I knew, this was not Emily.

“And here is Jay,” she exclaimed, strolling into the kitchen all tits and smiles. I stood up, confused. I kind of saw past her that two other forms were walking through the door, but my attention was on this ravenous sex kitten who had just addressed me in a Latina accent.

“Hi,” I said, brilliantly. The woman was not shy, moving right into my arms, sliding her entire slim hot body against mine.

“I’m Jasmine, “ she purred. “And I am very happy to meet you.”

“I am SOOO sorry,” came Emily’s voice, and then she was standing beside us. “Now let this poor boy go, you miserable slut!” Emily was a little drunk, obviously. With a giggle, Jasmine moved out of my arms, and planted a kiss on Emily’s cheek. “Hi,” Emily said lovingly, and leaned in to give me a quick kiss. I felt fingers on my cock, bursting through my jeans, but had trouble processing that, because Emily was using both hands to hold my face while she planted a second, longer kiss, and out of the corner of my eyes, I could see that Jasmine ambling away toward the liquor cabinet. I was able to move my head a bit and see that another smooth, tanned, perfectly manicured hand was rubbing my crotch. I followed the arm up to see another gorgeous woman standing there in a thin black cocktail dress.

Emily leaned back and rolled her eyes toward her other friend. “This is Jane, Jane, I see you’ve already gone to the candy store with Jay.” Jane giggled, took her hand off my cock and leaned in to give me a three way kiss with Emily. The two girls must have practiced this before, because without saying anything, both began tonguing at my lower lips. I was shaking, literally in shock.

“Hi Jane,” I mumbled, stepping back and away from them, if you can believe it. “Um, I, um, I …. So what is this?” I asked, unable to find words.

Emily giggled. “These are my friends. We’ve been drinking a little. I was telling them about your cock and reaming my ass and pissing all over me in the shower, and…”

“And that’s pretty fucking twisted,” Jasmine interrupted from the side. “But kind of sexy the way Emily told it.”

“And we wanted to meet you,” said Jane. “And I have to say, you are as fucking sexy hot as Emily said.”

“Corkscrew anywhere?” Jasmine asked from the side. “Third drawer to right,” Emily told her. “Thanks babe.”

Emily looked at me, and got serious for just a sec, through her drunken haze, looked at me. “You ok, lover? This was kind of spontaneous. I wasn’t planning on bringing these SLUTS back.” She emphasized the word “sluts” and spoke it to her two friends.

“You’re the piss whore that sucked down his pee,” Jasmine said. “You shouldn’t be calling us names.”

“You two sucked off all those guys last week at the orgy.” Emily reminded them. “That was truly gross.”

“It wasn’t horrible,” said Jane, winking at Emily. “My jaw was a little sore the next day.”

“And my knees,” added Jasmine. “Okay, who wants a glass?”

“So,” I asked quietly. “What’s the plan?”

Jasmine strolled over with two glasses of wine. She handed one to Emily, and set the other on the counter beside me, and pushed her tall, beautiful slim body up against mine. She slowly licked my lips and then with her teeth gently bit my lower lip. I could feel her breath mingling with mine, and also her fingers unsnapping my jeans. She skillfully popped the fly open and then slowly lowered herself in front of me, at the same time skivvying my pants down my legs.

Jane giggled and Emily moaned when my thick, fully erect cock popped out, and smacked against Jasmine’s pretty face. The Latina MILF just opened her mouth and popped my dick into it, pushing her face toward me, and sinking the length of my shaft into her throat. Jane stepped forward, one hand around the base of my cock shaft, and the other over her lifted dress and already in her own pussy, while Emily gently began chewing on my right ear. I was leaning back against the counter, my cock impaled in Jasmine’s mouth, watching Jane’s hairy pussy split by her own fingers, and feeling Emily at the side of my head, licking and chewing on ear and neck.

“Let me help, you selfish cunt,” said Emily, dropping to her knees and pulling open the front of her cocktail dress, exposing her lovely soft tits and erect nipples. Jasmine pulled back off my cock and let Jane’s hand guide it into Emily’s mouth, and then moved lower, licking my ball sack like a dog licking frozen hamburger that had just fallen on the kitchen floor. I moaned as Emily sucked and licked with her slathering tongue up and down the cock.

“Get him away from the counter,” suggested Jane, helpfully. “I want to lick his cute ass.” The two ladies kneeling in front of me slid backwards a few feet, and I followed, their contact with my cock never breaking, and then felt Jane stripping off her dress behind me and getting down on her knees. Suddenly I felt a breath on my ass cheeks, hands separating them, and then a very wet, stiff, wonderful tongue began pushing at my butthole. Jane jammed her face as far as she could push it into my crack, and her tongue played around right inside my asshole, while Emily and Jasmine took turns sucking my cock and then grabbing it from the other slut, and then having it grabbed back, with the girl not currently sucking staying occupied by licking my nuts.

Thankfully the three gals pulled back after a few minutes of this. “Throw him down on the floor- over on the rug,” said Jasmine, breathing hard, and pulling her cocktail dress over her head, revealing small, pretty pale-nippled breasts. “I want to ride that cock.”

“Good idea,” Jane said, standing up behind me. I was led over to the living room, and pushed down on the carpet. Emily grabbed a small pillow off the couch and put it under my head. Jasmine wasn’t kidding. I was on the ground about five seconds, starting to get comfortable, when she straddled me, her long slim legs disappearing above me into a shaven pink slit. She simply squatted down, and impaled herself on my cock, which was being held in position by Jane, down on her knees beside me. I moaned as my thick rod slid all the way up Jasmine’s tight pussy, the head of it bumping on what must have been her cervix. Jasmine began riding me like a mechanical bull at a dive bar, her tits bouncing wildly, her thick hair flinging here and everywhere. She was facing me and I was rapt watching her beautiful sex-crazed face, hardly noticing the breath on my balls as Jane moved between my legs, actually straddling one of them. Her hairy pussy slid down on my right foot, my toes sliding into her juicy slit, and her tongue at the same time began licking at my balls and shaft, and then up to Jasmine’s asshole. Apparently Jane liked ass!

Then my view of Jasmine was obscured, because Emily had crawled up, straddled my head with her own impossibly long, curvy legs, and squatted down on my face. She planted her pussy inches from my mouth, giving me room to breathe but definitely putting her gushing slit and pretty asshole within range of my tongue. So I lifted my head a bit to lessen the gap between tongue and cunt and began lapping at her nethers like a dog licking its own ass. I couldn’t see, but from the sound, I could tell that Emily and Jasmine were kissing like lesbian sluts; all the while Jasmine was riding roughly and grinding her crotch on my dick, and Jane was down there doing unspeakable things with her tongue to the inside of Jasmine’s asshole.

Emily stopped kissing Jasmine long enough to bark an order. “Jane, stand up here beside us!” Jane got up and stood right beside the three of us. “Spread that cunt out and piss on us!” Emily ordered. Jane giggled, but then a moment I heard a stream of pee, and felt warm and salty liquid hit my body, dripping off of Emily and Jasmine’s faces and tits, as Jane hosed them down with a stream of salty girl piss. Jasmine laughed, and just fucked my cock harder, and then felt that pussy gripping my cock pulsate. “Cum, you fucking bitch,” growled Emily, and felt her body move as her hands squeezed and spanked Jasmine’s tits. Jasmine howled, and came all over, soaking my already soaked body with more cunt liquid, and then fell off me sideways. My cock popped back up, glistening with her juices.

“Can I go?” asked Jane. “I really have to have that cock in my ass.”

“Fuck, yeah,” exclaimed Emily. “I’m fucking this boy all night, so you better get yours now.” Then she jammed her twat down on my face, and squeezed her thighs as she began to cum, and I couldn’t quite hear what was said next. I felt another slender body lowering itself on me, and felt my cock sliding into a very tight hole that felt different from Jasmine’s cunt. I realized that Jane had squatted down and was fucking her asshole with my cock. I also realized, just from how her ass and legs felt on my sides, even though I was blind from being buried in Emily’s crotch, that Jane was facing away from me, ass fucking her tight butthole while in reverse cowgirl position.

“Jasmine, you miserable cum dumpster,” barked Emily. “Make yourself useful and get down there and put a fist in Jane’s twat.” I felt Jasmine moving between my legs, and felt her tongue on my balls and shaft, and then farther up, as she ate Jane’s pussy.

Emily lifted off of me and stood up, moving over near them. Without warning, she began peeing all over Jane’s body, her hairy pussy, and Jasmine’s pretty face eating her out. I felt warm and sticky, and could smell pee everywhere.

“Ohhhh, that’s so fucking hot,” moaned Jane, fucking her slim ass on my jutting cock, and turning her head to lick Emily’s pussy, tonguing out the last drops of golden piss.

“Fist this whore,” Emily ordered Jasmine. I felt Jane shudder, and felt some movement down there, and couldn’t see it, but guessed that Jasmine had slid her hand into Jane’s cunt, stretching it out, even though I imagined her hands were small. Jane began convulsing and uttering nonsense syllables, orgasming from the combination of ass fucking, cunt fisting, piss drinking and oral abuse. Her orgasm lasted about thirty seconds, and then she faded, rolling off of me.

Jasmine hopped up and ran to the kitchen and returned with a warm, damp soapy hand towel, which she used to completely clean off my cock, balls, taint, and asshole. “Lift your hips a bit,” she told me, while Emily watched. Then Jasmine, this beautiful Latina goddess, began licking my ass, and like her friend Jane, couldn’t resist pushing her tongue into my butt. Emily leaned over and began sucking my cock again, since it hadn’t gotten soft yet. She stopped for a moment, and looked up at me. “Do you need to pee at all?” I nodded. I had to go really badly, if truth be known.

“Stand up,” Emily told me. “Come here girls.” I stood, and the three gorgeous women got on their knees in front of me, looking fucked out and fucked up, make up smeared, already smelling of piss and pussy juice and ass, hair wet, mascara smeared, frazzled and slutty. And it was just beautiful. “Come on, stud, hose down your sluts,” ordered Emily, and so I did, letting loose a thick stream of golden piss, hitting each girl one at a time and the together as they did a three way tongue kiss, and I peed in their mouths and on their tits. Jane playfully spat the piss back at me, so I hosed her in the eyes, and she sputtered, flinching.

I hadn’t lost my hard on, and after the pee stopped coming out, I just kept stroking, and found myself already perilously close to cumming. “You close?” Jasmine asked, looking up at me, wiping the piss out of her face. I nodded, legs already shaking a bit as the orgasm built.

“Cum on us,” Jane said, looking up at me. “Give us your sperm.” Emily giggled and stuck out her tongue, and Jasmine stuck hers out as well, touching Emily’s. All three girls were looking up at me with big eyes, and I just melted into the orgasm. My cock spurted the most copious load I’d ever shot, smashing onto the girls’ tongues and their lips, teeth, cheeks and foreheads, covering all of them with white love icing. They softly cried out with pleasure at seeing me cum so hard, and then they were back at my cock, taking turns sucking it, licking, cleaning it up, playing with the cum on their tongues, kissing each other, spitting into each other’s mouths.

I just kind of collapsed on the living room floor, a few feet away, on a dry spot, and for a while my eyes were closed, and I felt, rather than saw, three beautiful women touching my body, rubbing me, licking me, kissing me, cleaning me up, grooming me like parrots grooming another bird. There was soft, loving chatter between the three best friends, which I wasn’t really paying attention to, being adrift in my sensual pleasure overload. Then, to no one’s surprise, I passed into sweet sleep.

I awoke to a dark living room, a blanket having been tossed over me, and a naked Emily, freshly showered and clean, cuddled up next to me. I moaned and kissed her shoulder. She turned and smiled lovingly at me. “Let’s get upstairs. You need to shower, and then we might a few hours to sleep before you leave. Jacob….”

I nodded. “Yep, I know. Okay, let’s do it.” The two of us got to our feet, both naked. I saw my clothes neatly folded off to the side. Holding the blanket around us, we walked together to the staircase that led upstairs.

Source: reddit.com/r/Erotica/comments/dwdzqg/upstairs_a_milf_fantasy_part_iii_emily_and_her