My first time was with my friend’s mom [M18 / F40s] [milf] [bikini] [boy toy] [seduction]

There’s no way it was on purpose, no way anyone could have planned this snub, but I’m either way feeling a little left out.

Greg had been flirting with Amy for months, and we were all rooting for him, so when they were spending a little too much time alone in the corner of the pool, thinking nobody realized she was grinding her ass on his crotch, many knowing grins were exchanged when they finally sneaked off somewhere into the house.

Amy had brought her best friend, Zoe, like she always did, and after a painful thirty minutes of awkward shyness, she had sliced through it with a knife by walking right up to my buddy Jarrod and saying, “Come make out with me.” And that was the last I saw of either of them.

Dan, whose house we were at, had, in his quiet way, somehow managed to win the affections of Greg’s sister. Dina was older, in college, and only came with Greg because “she was bored” and had been quite clear she wasn’t “going to touch any of Greg’s dweeb friends.” And yet, I can still hear her and Dan’s giggling and gasping from the white bench hidden in the thick foliage of the side-yard garden.

Most surprising was Cynthia, beautiful, aloof Cynthia. I don’t know who invited her or why she came — we definitely weren’t her crowd. But we’d all just graduated, and all those high school cliques were in the past I suppose, because here she was, one of the hottest girls in our class, hanging out with us. Even Greg had turned his attention away from Amy when Cynthia pulled her t-shirt and shorts off. She’d ignored our gawks, jumping into the pool, curvy and elegant, in the sexiest blue bikini. Now, she’d gone off somewhere too, but since I can see her blue bikini top laying discarded on the patio, and Conner, nerdiest of us all yet with a strange nerd confidence, is also mysteriously absent, I can’t but help feel a pang of jealousy.

So here I am, floating on an inflatable pink raft on Dan’s parent’s pool, entirely by my self. I suck the straw of my soda cup, and nothing’s left but ice, the metaphor a little too on-the-nose for my liking.

I sigh, try to imagine something other than all my friends getting their dicks wet. Hey, I’ve graduated, no more tests, no more essays, no more reports. Yes, I’m enrolled in university in the fall, but that’s distant. Right now, I remind myself, I’m completely worry-free. And in a pool, doing fuck all. “Life could be worse,” I say aloud, to myself.

“It’s not that bad, is it?,” someone says. I don’t recognize the voice.

I lean up, look around. Peering down at me from the edge of the pool there is a woman, tanned and copper, hair pulled back tight and through a white visor. I must look confused, because she grins, says, “I’m Dan’s mom, Krissy.”

“Uh, hi, Dan’s mom,” I say. I’ve never met his parents, and he’s never talked much about them, but she’s younger than I expected.

She walks off, splays a towel out over the cushion of a wooden recliner. She’s wearing this flowy, white wrap, all folds and gossamer layers. But as she bends over to hoist the parasol between the recliner and its twin, it’s hem rides up her thighs, and I stare. Her legs, they’re long, shiny smooth, and so sexy. My attention is arrested and I don’t even realize it until she catches me gawking. “Come,” she smiles, patting the empty chair next to her, “Keep me company.”

“Ok.” I’m not good at recognizing flirting, I still think she’s just being friendly. And I’m the type that obeys instructions from parents.

She’s sitting sideways on her recliner, so I do the same, facing her.

Her plush lips smirk, then say, “So which one are you?”

I want to answer, but I don’t understand, so instead I frown.

She clarifies, “What’s your name?”

“Oh! I’m Eddie.”

“Well, Eddie,” she says, pulling her visor off now that she’s in the shadow of the umbrella, “Did your friends all leave you behind?” She pulls a clip from her hair, and it cascades down in long, straight bronze locks, shimmering despite the shade.

“Oh! Well, I mean, yeah,” I say sheepishly, “They’re all, um… you know.”

“I do?” her eyebrow arches. She runs her fingers through her hair, pulling out invisible tangles.

“Well, the girls, they, um–” It’s not even that I’m trying to give my friends privacy, it’s just that I don’t know how to talk about sex. I stare at the ground.

“The girls what?” she frowns.

I swallow. “Everyone’s… you know, finding love, or whatever.”

“You mean they’re fucking.”

I sneak a glance at her, see her watching me. We make eye contact, just for a moment, before my gaze returns to the flagstones. “Uh, yeah.”

“Well, good for them. You’re all adults now, and as long as you’re safe and willing, sex is fun and healthy.”

“Yeah,” I grimace, bracing myself for the inevitable follow-up questions, the ones about my own dating life, the ones where I end up having to explain just how bad with girls I am.

But it doesn’t come, and when I look up to see why not, my breath catches. Dan’s mom — Krissy — tugs on the white ribbons holding her wrap together, and no longer bound, it slips off her, falls to the cushion below. But it’s not the wrap I’m looking at, it’s Krissy herself, now clothed in nothing more than a string bikini.

It’s colorful, a pattern of red and yellow and blue stripes, a soft material. And it’s design, a strap over each of her shoulders, another strap around her back, the straps pulled taut and meeting over the large swell of her tits, holding them back not with cups, but with mere triangles of fabric, strategically arranged to cover her nipples and the front of her breasts, but not their top, bottom, or sides. And her tits, the bikini does nothing to disguise their shape. They’re large, round, full, wider even than her torso, the same smooth copper as the rest of her skin.

“Damn, Eddie,” she chuckles, “I guess you’re a fan.”

I’ve been staring, and when I realize it, I’m supremely embarrassed, cheeks reddening with blush. “I’m sorry! Sorry!” I stammer.

“Don’t be sorry,” she says. Her and her tits lean back in the seat, bouncing as they do so. “I like the attention, especially from a cute young boy like you.”

It’s not just her tits, either. She’s slender, sultry, refined in her sexiness. The string on her bikini bottom wraps up and around the rolling curve of her hips, covers her sex in a similarly small triangle of fabric.

“You’re–” I start, “You’re–”

“Yes?” she grins at me.

“You’re hot!”

“Don’t sound so surprised,” she says, “Though, I suppose your brain is missing some of its blood flow.” She nods at my crotch.

I trace her gaze, and am horrified to find my cock rock hard and making an obscene tent out of my shorts, the wet black material of my swimsuit clinging tightly to my shaft.

“I thought maybe I’d turn the heads of Dan’s friends,” she says, “But, uh, goddamn, Eddie. I’m feeling honored. That is one serious-looking erection you’ve got there.”

I’m scrambling to cover myself, shoulders caving in, leaning over, pulling on the fabric of my shorts.

“No, no, no,” Krissy shakes her head, “None of that.” She reached over, takes my wrist in her grip, strokes it. “Calm down, Eddie, it’s just a hard-on. It’s nothing I haven’t seen before. Sit back, relax.”

She’s leaning into her recliner, smiling at me. I take a deep breath, try to calm myself, follow her lead. I lean back into my seat, trying to look relaxed.

“That’s better,” she coos. I glance over again, see her staring at my crotch, at my cock, now even more prominently on display. I try to pretend this is normal.

It is anything but.

Krissy cups her chest, squeezes. “I got these as a gift to myself, you know,” she says, “After Dan’s father left me for that slut secretary of his, I suddenly found myself single and with half of all his money. So I used it to treat myself, finally get the tits I always dreamed of. And I didn’t get cheap ones, either. These are primo, Beverly Hills clinic, best available. Here, cop a feel, try them out.”

I reach out, but I’m too hesitant, and she takes my wrist, depositing my hand right on her tit.

Now, I’m a dork, and I’ve been a dork my entire life. I don’t admit this readily, but I’ve made it eighteen sad years without ever having touched a girl’s breasts. I don’t know how I expected my first time would be, but it certainly isn’t this.

So I’m awkward, fumbling, tentative in my fondling. “Oh, wow, yeah,” I say, “They certainly do feel, um, very nice.”

“Oh, come on,” she scoffs, “You’re barely touching them. Get over here, get yourself a real, proper grope.”

“Uh–”

Her nose flares, eyebrows rise. “Now, Eddie,” she says, like I’m being scolded.

It works. I move to her bench, sitting awkwardly in front of her while she folds her legs criss-cross.

She grabs both my wrists, guides my hands to her chest, plops them down roughly. “Feel me up,” she instructs, “It’s why I have them.”

She arches her back, watches me with a knowing smirk on her lips. I squeeze her tits, feel their weight in my palms, grow more assertive.

“Good,” she encourages.

And her tits — I know I don’t have much to compare them to — but they’re just the best ever. So soft, so pleasant, flesh bending and contorting to my fingers, spilling through my large hands. I push them flat against her chest, watch how they spread out. I let them go, watch how they bounce.

My thumb accidentally slides beneath a strap, and she bites her lip. “Can I please?” I point at her bikini top.

“You’re so polite,” she laughs, “Of course you can, Eddie. Do whatever you want. I’ll tell you if it’s too much. But I doubt you’ll find that limit.”

Fuck, she’s hot, and pretty, too. I’d not seen it before, too distracted by her age, by her status as ‘parent.’ But she’s gorgeous, long eyelashes, high cheekbones, thick lips, haunting gray eyes, oozing with confidence. And as I pull her bikini top up and off, and those heavenly tits pop free, pert and perky, with the sexiest little tan nipples atop each, my jaw drops. “You’re perfect,” I mutter.

“I wouldn’t go that far,” she says, genuine smile spreading across her face, “But, thanks.”

She doesn’t have to tell me, and I don’t have to ask, I just know it’s what I should do next — leaning down, planting my lips around a nipple, sucking it into my mouth.

“Ahh,” she sighs, “I thought you’d never…”

She leaves the thought unfinished as I bring my hand up to the breast I’m not sucking on, fondling her, tweaking her other nipple.

I am in paradise, this sexy woman with a better rack than I’d ever even dared dream of, letting — no, encouraging me to grope her, play out my fantasies. And fantasies I have, bolstered by her eagerness for my attention, and I do everything I can think of, everything I ever imagined.

I suck and pinch and nuzzle and squeeze and slap and caress and lick and bury my face in her cleavage. She grins, keeping her back arched, her tits prominent, holding them out for me to suckle, swinging them side to side for me to ogle.

“Eddie,” she says, “Eddie.”

I think she may be trying to get my attention. “Huh?” I say, looking up at her. I have her tits pressed together, nipples touching, slick with my spit.

“I’m horny.”

“Oh,” I say, not sure what to do with this information.

“Are you going to fuck me?”

“I’ve never, um–” I catch myself, blushing at my careless confession.

But she’s classy, kind. “I know. I mean, I didn’t know, but I guessed. And I like watching you, you’re cute. But if I let you keep playing with my tits, you’re just going to end up creaming your pants. Which, if that’s what you want? Although I’d much rather be your first.”

“Ah, yeah…” I say, noncommittal to the end.

“Is that what you want?”

I swallow. “Yes.”

“Good,” she says. Then her face grows stern. “Stand up. Take off your shorts. Show momma your dick.”

I rise, slowly.

“Do it!” she barks.

I don’t even let myself think about it, I just shove my shorts off. My cock springs free, red and swollen and stiff as a broomstick, right in her face.

“Hrm,” she frowns, studying it like it’s a puzzle. She reaches out, and I gasp as her fingers slide over my balls, painted fingernails dragging over my sensitive virgin skin.

She squeezes my sac, tugs on it, and I whimper.

“Try not to cum in my mouth,” she says.

And before I have time to grasp what that means, while my brain is still figuring out how I’d possibly cum in her mouth while my dick is hanging free in the air, she cups my balls and pulls them towards her, thereby making me step closer. And as her mouth swings open and my dick slides inside, I have a brief moment of realization, “Oh!” before the pleasure hits.

“Oh! Fuck!” I groan, watching my shaft slip between her lips, feeling her tongue caress down my vein.

She looks up at me, winks, then pulls my dick out, licking it clean as she goes.

I whimper. This is the best thing that has ever happened to me, ever. Her lips are stretched around my the head of my cock, but when she sees how I’m looking at her, the corners of her mouth turn up in a grin.

And then the blowjob really begins, my balls in her hand while her mouth slides up and down my shaft, thick lips slurping and sucking, tongue teasing. Her long, straight hair swooshes to and fro over her tits, and I am in a universe of ecstasy.

I feel it welling inside me, a real orgasm, not those pale imitations I give myself with my hand.

But then she pulls off, and I almost cry. My chest is panting, and I give her what must be a pathetic, desperate look.

“That was just to get you warmed up,” she explains, “I’ve been known to keep a guy going that way for an hour, never quite letting him cum. Eventually, though, there’s no stopping him, and he’ll pop whether I’m helping or not. And you, Eddie, you don’t want that. Not today, at least. Today is your big day, a day you will remember the rest of your life. The day you first get pussy.”

At that word, ‘pussy,’ spoken so casually, with so little of the reverence me and my friends usually regard it with, my eyes widen in epiphany. All of this, the flirting, the groping, even the blowjob, it hasn’t felt real. But pussy — my dick finally accomplishing its reason for existence — there’s something sacred about this.

“Having second thoughts?” she says, frowning, studying my face.

Most guys, I imagine, first have sex with a girl their own age. Not with their friend’s mother. But Krissy — forget her age, forget how I know her — she’s beautiful, perfect — and I can think of no better way for this to go.

I grin. “You fucking kidding me?”

“Good,” she says, “Sit down on your chair, like a good little boy.”

“Yes, ma’am.”

“Don’t call me that,” she says, standing up, pulling her top off.

“Sorry,” I say.

“Don’t apologize, either.” She yanks on the strings at her hips, and her bikini bottom falls to the ground. Her pussy, bare and tight and immaculately manicured with a thin little strip of hair above it and nowhere else, it makes my breath catch. “You’re a man,” she continues, “You do with me whatever the fuck you want to.”

“You’re beautiful,” I say, eyes glued to her crotch.

“Thanks,” she giggles. “Sit back.”

I lean the chair back, but keep my head lifted, not wanting to miss a thing. She climbs onto my chair, straddling my thighs. Her legs are warm against me, an intensely erotic feeling, her bare skin against mine. But it’s her pussy that has me fixated, now spread open, pulled taut by her position. I can’t look away, it’s the single hottest thing I have ever seen.

She takes my dick in her hand as she lifts herself up, moves into position. Her sex is now over my hips, and I reach down, rub it with my thumb.

“You don’t have to do that,” she says, “I’m already wet.”

“I want to,” I say, stroking her, fondling her, a lion cub playing with its first kill.

She grins, but pushes my hand away. “I’m tired of groping, I want to fuck.”

I look up at her. “Wait, do you think we should use a condom?”

“No.”

And then the tip of my cock is inside her. She holds the position, studying me with an ear-to-ear grin. “How’s that feel?”

I’m panting, horny beyond reason. I grab her hips, yank her without result. “I need more,” I plead.

“Well. Since you asked so nicely.” She descends, her pussy taking my dick like an elevator, one floor at a time. When she reaches the bottom — when her ass rests on my thighs — she pauses again. “Here it is,” she announces, “Your first time. Everything you expected?”

She’s so tight, wet and warm and elating, and it feels so very correct. “Even better,” I moan.

She laughs. “I know, right?” She wiggles her hips, makes me gasp. “I’m going to go slow, nice and easy. You tell me when you want me to speed up, ok?”

“Ok!” I gasp.

And she’s an expert, a master, fucking me like she said, with a slow, steady rhythm that fills me with bliss without making me rush to orgasm. I watch her like she’s a goddess, hands on her waist. I know she’d let me touch her anywhere, but something about her waist, the flatness of her belly, the curve of her hips, calls to me, tells me this is where my hands should be.

I know the reputation of first times, that I shouldn’t expect to give my partner much pleasure. But Krissy seems to be enjoying, the way she bites her lip, the way her hair clings to her sweaty skin, the way her breathing quickens.

“Pinch my nipples.”

I give her a look. “I think you should go faster now.”

She smiles, eyes sparkling with delight. “Oh.” She arches her back, rests her weight on her arms stretched out below her. This position lets her pump her hips with a fervor I haven’t yet seen, and with my hands on her waist, she even lets me guide her, although all I’m mostly doing is holding on.

Her pussy, it’s so tight, wringing out my cock, begging for my spunk, eager for my seed. “Cum in me,” she commands, “Give me all your virgin cum, little boy. Fill my pussy with it.”

My grip on her stiffens, and I groan.

Her eyes glow. “That’s right, drain your balls in me. Give me every last drop.”

I strain, gritting my teeth, flexing every muscle in my body.

“Be a man! Fuck your semen into me. I want your cum so fucking bad.”

I’m making this noise, I don’t know, a long, low groan, as I orgasm, by far the best orgasm I have ever had. My dick is in euphoria as it completes its mission, emptying itself inside a woman for the first time.

“That’s right,” she spurs me, “I can feel your fat load inside me, don’t stop now.”

I’m delirious with pleasure, adrift in bliss.

I come to laying back on my recliner, buck naked, grin permanently installed on my face.

Krissy — Dan’s mom — is back in her chair, the white wrap pulled back over her. But that doesn’t stop me from looking her up and down, basking in what curves I can see, memory fresh of those I cannot. “You look happy,” she says.

“I am. Thank you for that. It was … I’ll never forget you.”

“I know.”

“Can I see you again?”

“Don’t think this is some sort of romance.”

“I wasn’t scheming romance, I just want to get laid again.”

She chuckles. “Well. We’ll see.”

“Eddie!” a voice booms out, “What the fuck? Where the fuck are you clothes?” I look over, see Dan stomping out from the garden. Dina trails him, makeup smeared. “That’s my mom!”

I try not to laugh. But Krissy bursts into giggles.

“What’s so funny?” he whines.

Dina eyes my dick, gives me a look I cannot read. I spread my legs, let her stare.

Source: reddit.com/r/eroticliterature/comments/wrpth7/my_first_time_was_with_my_friends_mom_m18_f40s