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Young guys are so easy [F40/M20] [son's friend] [groping] [handjob]
Author Summary
TerriblyEasy is a female looking for a male in handjob
Post Body

“Care if I join?”

“No, Mom, it’s cool,” Jacob says, not even looking up from the screen. He’s splayed out on the recliner in the rec room in the basement, two of his friends similarly arrayed around him, and they’re watching some comic book movie.

“Thanks,” I say, taking the far couch, the one that doesn’t have a great view of the TV, and sip deep from the glass of chardonnay I poured for myself. It’s late and I’ve just put another exhausting shift behind me. It was nothing remarkable, some assholes, some decent tips, only two or three uncouth remarks from Fernando in the kitchen. I sigh and pull out my phone. I don’t care about the movie. Even if Jacob and his friends are poor company, drinking alone in my bedroom is a step too far, even for me.

And I flip through my socials, only halfway paying attention to what I’m reading, paying even less to everything else. Except the wine, of which I ensure every cool and tangy drip makes it down my throat. I get up, refill my glass, return to my spot.

Someone is snoring, but the movie plays on. I think maybe it’s a different movie now, actually? I’m not sure. I return my attention to my phone, deciding that I’ll just finish this glass and then head to bed.

But before I can, I’m joined on the couch.

“Julian,” I announce as my son’s friend sits down beside me. Not so close that he’s touching, but not so far away that he couldn’t. “Don’t start.”

“Don’t start what?” he feigns innocence, “I’m just being friendly, Charlotte. I just want to say ‘hi’ and ask how your day was.”

I sigh, give him a wary glance. He’s tall and broad young man, athletic in build ever since he gave up spending all his free time painting miniatures and started dedicating it towards water polo. “So then ask,” I say, “But be quick about it. I’m going to bed in a minute.”

“You need someone to tuck you in, Charlotte?”

Julian’s always been a shameless flirt. Jokes like this are nothing new from him, although he’s been growing more bold ever since starting to take classes at the junior college. “Julian,” I warn him, “Behave yourself.”

“They’re both asleep, you know,” he says, “I could come with you to your bedroom, tuck you in tight. They won’t even know.”

“Cut it out. You’re like a dog chasing a car, wouldn’t know what to do with one if you caught it.”

“Oh, I think you’ll find I’m very good at catching cars, Charlotte,” his grin is unflappable, and it’s cute. I could be stoked by attention from a guy like him, were he a stranger. But he’s not, he’s my son’s friend, and I’ve known him since he was sixteen. “I’m a gentleman,” he adds.

“I’ve had a long day, Julian. I just wanted to drink some wine before bed, is all. You flatter me, but I’m too old for you to waste your efforts on. So if you’ll please…” I show him my empty glass and make to stand.

“Allow me,” he says, taking the wine glass from my hand, his fingers brushing mine as they do. His touch is warm, strong. “Chardonnay’s your grape, right?”

“Uh…” I blink, “…yes.”

He climbs the steps from the basement back into the main house, and I sit back. I suppose one more glass won’t kill me.

But when he returns, he’s carrying two. “Cheers,” he says, clinking his against mine as he sits down. “Couldn’t leave you to drink alone, not a pretty lady such as yourself.”

“Julian,” I sigh, putting my face into my palm to hide my blushing cheeks. “I don’t know what your game is, but it’s not going to work.”

“Game? What game?” he says, “I just want to get to know you better. I’ve been coming here for a while, but I feel like we’ve never talked, you and me.”

Maybe it’s the wine kicking in, but something about that calm and steady smirk on his cute cheeks makes me want to humor him. “Ok, Julian. What do you want to know?”

“Well, Charlotte,” he says, his confidence a sustained constant, “How’s your dating life going? Are you seeing anyone?”

“Honestly?” I chuckle, “It’s abysmal.”

“Even for a gorgeous woman like you?”

I scoff. “Most of the single men out there, they don’t need a girlfriend, they need a therapist. Or you finally meet someone who’s charming and pleasant and treats you well only to discover that he’s got a wife and kids squirreled away somewhere.”

“That’s terrible,” he says, “I’m sorry you had to go through that.”

“What about you?” I say, forgetting for a moment who I’m talking to, attempting to have a normal conversation, “Boy like you must be getting plenty of attention from all the college girls.”

He shrugs, his grin spreading. “Some. But it’s not interesting to me.”

“Oh? Why not?”

“I tend to like women who’re a little bit more experienced. Who have a clear idea what it is that they want.”

I narrow my eyes. “And why is that?”

“It’s what excites me,” he says, “The idea of being in the hands of a woman who knows what she’s doing. Who’s not fumbling around, unsure of herself. Who’s not learning, but who already knows.”

“I see. And have you found someone like that?”

“Oh, definitely. But getting past the hurdle and proving I’m worthy of her attention has been proving a challenge.”

Our gazes have remained fixed on one another’s now for a good while. I lick my lips. “And what have you done to prove yourself worthy?”

“Well, that’s where I’m not sure. I’ve been friendly with her, keeping her company when she’s lonely, told her that she’s beautiful.”

“Beautiful, huh?”

“Yes, definitely. Especially in the outfit she wears for work, those tight waitress clothes are really so crazy sexy on her.”

“I see.” I sip deeply from my glass, partially because I need to, but also so he can’t see the warmth spreading across my cheeks. Yet I sit up a little straighter, arch my back a little, press my cleavage out into the unbuttoned top of my blouse.

“And I’ve also tried telling her what I want, but so far I haven’t gotten anywhere with her.” He finishes his glass, sets it aside. “Do you have any advice to a lovestruck young man? Any words of wisdom you can offer?”

“Well, Julian,” I say, a giddiness overtaking me, a frenzied intrigue, “An older woman like that, you shouldn’t mistake her for a prude. If you want something from her, you should show her exactly how she makes you feel, tell her explicitly what it is you want from her.” And I rest my fingertips on the thigh of his sweatpants, drag them to and fro and slip them down between his legs.

He gasps, his breaths suddenly coming fast and hard. “Oh,” he pants, “You think that’ll work?”

“I cannot guarantee anything,” I say, reaching across, teasing his far thigh in turn. I’ve held my gaze steady on his, but I’m not blind to the growing distraction in his sweatpants. I brush the back of my wrist across it. “But it’s worth a shot. What do you have to lose?”

He thrusts his hips up, shoves his pants down to his knees. And out pops up a thick and impatient erection, a fat shaft veiny and red and pointing straight up from his crotch like a tallboy can of beer. “Touch it,” he whispers, like he’s afraid to say the words aloud.

“Oh, Julian! My, what a healthy young man you are.” I play at innocence, even as I feel my own heat rising inside. “Is that for me?”

“Yes,” he hisses, “It needs you.”

I grin at him, mischievous and wry. “But I don’t know. My son is right over there, and your other friend, too.” I flick open the next button down my shirt, and then another. The fabric spreads, my black bra comes into his view, he stares.

“They’re asleep!”

“Julian…” I stroke his thigh again, now bare skin on skin.

“I’ve fantasized,” he starts, “So many times about this, about you getting me hard. Don’t leave me like this.”

“And what do I do, in your fantasies? Once you’re hard, I mean?”

His dick, if anything, despite not being touched has only grown more erect, has gotten stiffer and thicker since he first exposed it. “You– you–” he stammers, his confidence running thin and brittle. But he sucks a breath and finishes, “You jack me off. Make me cum.”

“That’s awfully nice of me.” I wrap my fingers around the base of his shaft, and you’d think I punched him in the gut from the way he reacts, eyes bugging, stunned look on his face. But as I squeeze, his smile returns, maybe a touch too casual and relaxed to be believable. “Although, I suppose, I am fan of big, fat dicks.”

“I knew you’d like it,” he says, “Women always do.”

With my other hand, I slap his dick. “Don’t get too cocky.”

He gasps, a burst of pleasure surfacing on his cheeks.

“Oh, you like that?” I slap his penis again, and as he looks at me in awe, I do it over and over, batting it side to side until I don’t even quite realize how I start but I’m jerking off the young man at my side, stroking his bulging penis from tip to base while he thrusts into my fist. “Julian, you horny boy. What type of woman do you take me for?”

“I’ve had a crush on you since the day I met you, Charlotte. I knew that one day you’d see me, too.”

“You knew that, did you?”

He nods, so sure of himself. I am becoming quite familiar with feel of his dick, the soft skin on its surface, the power beneath, the throbbing and pulsing of his arousal, and I subtly pull back on what I’m giving him, not wanting to drive him towards his pinnacle too quickly. “But this is–” he gasps, “So much better than I imagined, actually.”

We’re keeping our voices low and barely audible, speaking in hushed whispers. The sounds of his quickening breath and skin-on-skin contact fade into the television’s mindless noise. My son remains entirely asleep, completely unaware that right near him, his friend Julian is crossing all sorts of boundaries with his mother. It’s kind of fucked-up.

And Julian, he’s trying to act cool, like he’s got women playing with his dick on the regular, but I can see through his facade. His chest is heaving, and oozing from his red mushroom head is a steady drip drip drip of precum. I smear it into his shaft, wrenching his cock so hard I’m nervous I’m hurting him. But from the way he’s groaning, I’m not.

“This all you fantasize about?” I taunt him, crossing my legs, “Are your dreams really so small that all you want from me is a handjob?” I cup his balls, run a fingertip in little circles directly on his glans.

Even in his daze, his calm is unshakable. “Why don’t you sit on my lap, Charlotte?”

“Tempting,” I bite my lip. It really is, he’s got my pussy quite wet. “But no. You haven’t earned that, Julian. In fact, you’re already on borrowed credit. What’re you going to do to pay it back?”

He frowns, searching my face. My hand continues its steady beat, up and down his shaft, stroke after stroke after stroke. “I… don’t know. What?”

“You’re going to cum for me, Julian.” And I squeeze his balls and jerk him, harder and harder and harder, gritting my teeth directly into his cute and bewildered face until he’s making this strained grunting sound and I feel my fist running slick with his seed. I pump steady, milking more of his sticky white spunk onto my hand. Cum runs down my knuckles in thick globs, drips down his balls.

“Fuck…” he groans, the semen coming and coming, his orgasm continuous and full body. I give him another tug and yet more flows from him.

I laugh, tug him again.

He makes a guttural noise and keeps on cumming. He closes his hand on my wrist as I move to stroke him again, his grip powerful strong, and he collapses, catching his breath, his eyes rolled back in ecstasy.

“Clean up my couch,” I say, standing up from the delirious boy with the big penis, giggling as I walk upstairs. I wash my hands, take off my clothes, pull from the cabinet my favorite dildo — a purple silicone phallus that vibrates — and get into the shower, where I fuck myself silly before going to bed.

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3 weeks ago