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I crossed a line with my client [F22/F45ish] [touching] [groping] [teasing] [fingering]
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TerriblyEasy is a female in fingering
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Mrs Simmons is gorgeous. Laying out face down on my massage table, her body is on full display, naked and uncovered by the modesty towel that most people opt for even if it isn’t technically required. And she’s tall, her tan skin smooth and sleek and glistening from the workout she’s just completed, from the warm and humid air pumping into my small studio, from the massage oils I’ve been rubbing in. And her muscles are tight, toned, weary from exercise but practiced by years of training, an intense lifetime regimen of fitness. Her ass is incredible, her tits are the tits I wish I had on my own chest.

Not that I don’t get attention, even dressed in this simple white outfit I wear. My clients tend to be respectful, especially the men. A thirsty glance and a chubby bulge are the worst I’ve gotten from men. The groping and rude requests, those are the domain of women. It’s the women who overstep boundaries, who make untoward comments concerning my ‘young, petite’ body, made assumptions about my ‘wild and carefree’ sex life. They’re all baseless assumptions, for I tell them nothing, just smile and accept their money, thank them for their tips through clenched teeth.

But not Mrs Simmons. She says nothing when she shows up, always on time, never missing an appointment. She greets me with only a quick and beige smile, makes herself comfortable when I usher her into my studio. The meditative music thrums out from the speakers recessed overhead as I ask her, “The usual?”

“Mmhmm,” she hums, brown eyes closed, brown hair tied into a knot keeping bare her shoulders. Her tits, big, pert, fantastic, topped by brown nipples, hang out for anyone to see. Except there’s nobody here but me, and all I’m doing is massaging Mrs Simmons’ aches from her muscles, her soreness from her sinews.

The oil goes on my palms, my palms go on her shoulders, her arms, her legs, her feet. I knead and work her loose, the only sounds the faint music, the rustle of the vent overhead, the quiet slipping of slicked skin against skin.

Mrs Simmons knows my routine, knows when I’ve finished with one part of her body and am ready to move to the next. When I’m done with her front, she rolls over, presents me her backside without me having to ask. And I continue, massaging and kneading free her knots, gliding my powerful grip over her limbs, up her back, along her neck, down her spine.

And then I reach her ass. It’s… for lack of a better word, perfect. Thick without being fat. Round without losing tightness. A strong, powerful butt, expertly toned over the course of a million squats, firm and potent. I feel honored that she lets me work it, that she entrusts me with its care. I give it the respect it deserves, my oiled fingers coursing over her generous flesh. I massage it entirely, from her narrow waist out to the curve of her hips down to the tops of her long legs and then up, inwards, towards where her cheeks meet.

I still remember the first time, when I was massaging her same as I always do, and my fingers came in and slipped just a touch farther than I intended, daring down between the two halves her ass. I expected admonition, reprimand, rebuke.

What I got instead was her thighs parting, Mrs Simmons pushing her ass out. She wasn’t condemning for what I did on accident, she was encouraging me to take it a step further, to finish my exploration of her ass. Her pucker was bleached, tight, inviting, and the moan she made as I ran my thumb around it was from a place deep inside her, full of sensuous release.

Wasn’t release the entire reason she was seeing me?

I knew I shouldn’t, knew it was breaking all sorts of rules with propriety and with the spa and with basic common sense, but I did it anyway. I fingered her ass, felt her shove her butt up into my touch, saw her waxed sex grow slick with arousal.

And I gave her what she wanted.

She doesn’t always want it. Some weeks she’s content to just lay there, have her usual massage, the one any expert could give her.

But other days are like today, when Mrs Simmons is pushing her ass out just at me, spreading her legs apart to show me personally her dark pussy lips, dripping with sticky white heat. And, with fresh oil on my palms, I bring my hands in, massage her how she likes me to do.

A guttural sigh slips from her throat as I drag my finger in circles around her pucker, as two other fingers slide down between pussy lips to tease her clit. Her breathing deepens when I push a digit up inside her, when my thumb puts pressure on her asshole. And I earn a moan as my rhythm begins, a slow and delicate pace, deliberate in its caress, constant in its spark of the forbidden.

I shouldn’t be doing this, but I do it anyway, fucking Mrs Simmons with my hand, silently getting her off. It’s a little secret between us, never acknowledged, never spoken aloud. Yet she needs it from me, this is clear. She used to see me weekly, on Monday afternoons, the other masseuses on other days. When we crossed the line, I saw her again that Thursday, massaging her asshole, her clit. Then she switched her Tuesdays to me, too.

I have her sucking down air, building her tempo with considered restraint. I have learned how to touch her, when to touch her, where to touch her, and I ply my knowledge with the disposition of the masseuse I am. She’s never pulled away from me, never told me what I’m doing is too much.

And soon I have this beautiful older woman there, toes curling, grunting through gritted teeth like she’s twenty years old again. Her hips buck, her belly twists, a thick of arousal cascades down my fingers. I tweak her clit, curl my fingers inside her, work her asshole. And she gasps and cums, today’s orgasm a full-body throe, a spasm of arousal wrenching through her and squeezing out moans and whimpers.

“Fuck…” I hear her mutter.

After, I clean up, proceed as if nothing happened. With my back to her, Mrs Simmons sits up and catches her breath.

“Oh,” I say, “I’ll be out of town next month for a couple days, so–”

I gasp as she grabs me and pushes my back up against the wall. I drop the towel I’d been holding and stare up her, this naked and gorgeous older woman glaring down at me with clenched teeth.

I ask, “Did I do somethi–”

She unbuttons my pants, yanks down the zipper on my fly.

I look up at her, see determination in her eyes. Her hand slides under my white pants, under my white panties.

“Oh, you young girls,” she spits, “So tight, you don’t even know.” She’s fingering me, rough and hard and harsh. There’s nowhere to hide from it, and my pussy, already wet, loves being controlled.

Face to face, we stare into each other’s eyes as she wrings the pleasure from me, makes my slender tits heave with each gasping breath, makes my pussy desperate. I bite my lip to stop from moaning. She thumbs my clit and the moans come anyway.

“I should bring you home one of these days,” she says, “Let my husband have his way with you. Bet a whore like you would like that, wouldn’t you?”

My thigh is quaking and my hands are useless, flopping around wildly.

“He knows what to do with girls like you, how to make you scream for more.” She twists her fingers inside me, a new sensation that makes my chin drop and eyes roll back. “Not that you seem too difficult.”

She makes my climax come on, and I curl into her grip, unable to resist the pleasure. She holds me steady, fingering me along throughout, flicking my clit until I can’t take it anymore. I collapse down to my knees, roll onto my side, still shivering and twitching.

“That’s what I thought,” she shakes her head. “My card’s on your bench. Call the number there, if you dare.”

That evening, I stare at the card, masturbating with anticipation.

It’s only three days later that I’m teasing and licking Mrs Simmons’ asshole in the privacy of her own bedroom. I’m on my hands and knees and my pussy’s so wet. Mr Simmons shoves a toy into my ass and his cock into my sex, and it’s all I can do to stay focused on his wife’s pleasure. He chuckles as I make her cum, and then he pulls out only to roll me onto my back and push his balls in my mouth. Sucking his nuts, I watch up close as he fucks his wife’s ass, skewering her beautiful butt until he cums, and he’s kind enough to finger me off while he does it. I make to gather my clothes, but Mrs Simmons shakes her head, “We’re just getting started with you.”

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3 months ago