The first time I ever got a handjob was from a woman twice my age [mF]

Someone is whining. “Charlotte! Someone will see you!”

“Chill, Robbie. There’s nobody out here.” Laughing. “And anyway, let em look. You should show me off a little, you know.”

Then footsteps from the guy — Robbie, I guess. “At least put on a robe,” he says, “All of creation can see your… you know.”

“You’re no fun, you know that?” Shuffling sounds, then a sigh. “Bye baby, love you.”

I’m overhearing this conversation from through the sliding glass door to the balcony. It leaves me to imagine what this scantily clad woman looks like. And I can imagine quite a bit. Of course my daydreams don’t sate me, they only amplify my need to see, my need to know what this babe actually looks like.

So even though I’m only in my pajama shorts, I walk outside and lean over the railing, looking down the row of identical balconies spread out before me. I try to look casual, like I just happened to be glancing her way.

It doesn’t work at all. The woman, Charlotte was what he called her, turns out to be in the very next cabin over, and she’s looking right at me. “You heard that, huh?”

I chuckle, blushing at being caught. “Sweet birdsong greeting the dawn.”

“Liar.”

I grin.

She’s breathtaking. Tall — nearly as tall as me — and curvy, natural red hair, the cutest smile. I can feel my heartbeat in my throat.

She looks me up and down. “You gonna take my picture?”

“Huh?”

She nods at the camera dangling from my neck.

I don’t want to be a creep, so I say, “This is for–” I gesture out at the dawn light cresting over the open ocean, the islands speckling the sea, “–all of that.” The cruise ship slices cleanly through the low waves.

“Not a bad view, is it?”

I smirk and add, “Not that you’re not beautiful, too.”

Her cheeks warm and she makes a nervous giggle. “Whoa now, you’re going to make your girl jealous.”

“What girl?” It’s not a play; I’m actually confused.

“Don’t be coy,” she says, “I talked to her yesterday, leaving your room.” A breeze picks up, pulls her robe back. She’s quick to yank it into place, wrap it across her, but in that brief instant before she did… She’d had on this lingerie which went from crotch to tits, a see-through mesh which teased her contours, hinted at her full, round breasts, nipples darkening the tips.

What was she saying? “Oh. Yeah. That’s my sister.”

“Your sister? You went on a romantic cruise with your sister?”

I chortle. “It’s not like that. We’re here with our parents. They just got us our own room, so we wouldn’t bug them.”

“Must be nice.” She looks away, then back at me. “How old are you, anyway?”

“Sixteen.” I grin.

She buries her face in her hands. “Oh my god, you’re a kid. I’m flirting with a kid.”

“I’m man enough.” I give her a little crotch thrust.

“You’re horrible. I’m nearly twice your age, you know.” I can see her gaze dance across my bare chest, my shoulders. She doesn’t look disinterested.

“I’m cool with that.” There’s nothing but a plastic divider separating our two balconies. I unclasp the lock, pull at it, but it’s held fast. “Help me open this, let’s chat without leaning half-off the balcony.”

She gives me the side eye. “You wouldn’t know the first thing about being with a woman like me.”

“You could show me,” I say, “I’m young and impressionable.”

I get a laugh, but her protest continues. “I’m here with my boyfriend.”

“A woman beautiful as you, he shouldn’t have left alone. C’mon, open the door. I’ll behave myself, I promise.”

“You’ll be a good boy?”

“The best.”

She shakes her head and disappears from my view. But I hear the clasp slide, and then the divider swings open. She’s standing there, looking stunning, red hair flowing in the breeze, curves emphasized by the robe clinging to her. I can’t believe this worked.

“Joshua,” I hold out my hand.

“Hi Joshua, nice to meet you. I’m Charlotte.” She crosses the threshold to my side and shakes my hand. Now face to face, she leans back against the rail, a casual pose. Up close, she’s even more beautiful, with faint freckles, glistening lips, sparkling green eyes. The ocean passes calmly below us. Hands at her sides, her lips part, then she speaks with precise enunciation, “So what did you want to chat about?”

The question is a taunt, of course. A conversational tripwire, set in place to throw me off. I don’t fall for it. “You’re beautiful, Charlotte. I want to seduce you.”

She laughs in my face. “You did hear me say, I’m here with my boyfriend, right? My rich boyfriend, who’s paying for this cruise on his own, without his parents’ help?”

I hold my ground. “And yet, y’all aren’t married.”

“Married? You think that matters? We’re in love. I’m in love. He’s funny and kind and loves me back.”

“Bet my cock’s bigger than his.”

Charlotte scoffs. “That actually is how boys your age think, isn’t it? Nothing more important than the size of your dick. But if we’re talking dicks, know that Robbie’s dick is fantastic. He fucks me deep, shoves his dick down my throat, cums all over–”

I cut her off, “Then why are you here?”

“What?”

“If you’re so in love, so satisfied by Robbie’s dick,” I say, “Then why are you here, chatting with me?”

She’s silent, has no response.

I step closer to her. “My guess,” I say, “Is you’ve been with this guy a few years now, and things are fine, but you’re a little bored. And guys like me pay attention to you, turn their heads when you walk past. You don’t like to acknowledge it, but this excites you, makes you wonder if you’re missing out on anything by staying monogamous. Am I on the right track?”

She laughs in my face. “You think, even if you were right, I’d admit to any of that bullshit? You’ve got a real active imagination, Joshua, I’ll give you that. Sit your ass down in that chair right there.”

“Huh?”

“Sit! Sit boy, sit!” She puts her hand on my chest, gently pushes.

I stumble, catch myself, and sit on the lounge chair. She watches me, but I can’t read her expression.

She crosses back to her side of the threshold, slips into her room.

I’m confused — what’s going on? Did I offend her? Is she coming back? But then she walks back out. She sits down on the lounger opposite mine, sitting on it sideways so that she’s facing me, and puts something on the little table between the chairs. She’s got a knowing smirk, like she’s got a secret.

“Tell me the truth, Joshua,” she says, “How much sex have you had?”

I swallow. “Well… if we’re counting, that is… none.”

She chuckles. “So all your talk is just… what? Shit you heard from the internet?”

“I– uh… I guess so, yeah.”

She rolls her head back, laughing loud enough to echo down the ship, out across the ocean. “Oh, you’re lucky you’re good looking, Joshua. Take my picture.” She bites her lip, tucking her chin and smiling invitingly.

It’s so sudden, such a quick change in direction, teasing me one moment, flirting with me the next. And she’s so cute, her flirting sends me reeling, and I think my heart actually skips a beat.

“What are you waiting for?” she says.

I fumble with the camera, zoom the lens out, focus it on her, and snap the shutter.

“Good,” she says, “I want to make sure you remember this, exactly the way it happened.”

“Remember what?”

“Keep taking pictures, Joshua.”

I hold the camera up to my eye, and she pulls her robe off. Her mesh lingerie is on full display, round tits pushing out against the material. I ogle and snap a picture. And then my eyes scroll down, past her tits, past her navel, to the little landing strip of hair, and the slit of her sex. My eyes are wide, my jaw slack, but I remember to take another shot.

She glows under my attention, delight in her eyes as I look at her in awe.

“Do you know what this is?” She holds up the item she brought from her cabin, a plastic bottle with a pump on top.

“Uh, lotion?”

“Lube.” She pushes the plunger, squeezes some on her hand.

My breath catches. “L–lube?”

“Lube,” she repeats, holding up her hand. “Camera ready!” And then she leans towards me, lifts the waistband of my shorts with one hand, and slips her lubed hand inside.

I suck in a sharp breath. She grabs my cock, and her hand is cold, soft, silky smooth, perfect. I’m not erect, but my dick pulses, instantly on its path towards stiffness. She slides her hand down my length, then starts again, a confidence to her tugging that speaks towards years of experience.

She enjoys my reaction, smiling at me as my breathing quickens. “Don’t forget to take pictures,” she teases, yanking on my cock.

I’m panting, but I take a photo. Not of her hand on my dick, but of her beautiful smile, of her sexy expression as she rubs my cock.

“Oh! Wow! There he goes,” she says as my dick springs up to full erection, “It’s amazing how quick teenagers get hard. Let’s get your shorts out of the way.”

I have never taken off an item of clothes any quicker than I do these shorts.

She smiles at my dick, squirts out more lube, rubs it in. She rubs my balls, too, palming them, cupping them in her soft touch. I roll my knees out and lean back, watching her work on me.

“What do you think?” she says.

“Fucking amazing,” I say, taking another picture of her grin, her glimmering green eyes.

“You’ve got a nice dick, Joshua,” she says, “Nice and strong.”

Her hand slowly pumps up and down the length of my shaft, a tight ring of her index finger and thumb passing from base to tip and back again. It makes a wet slippery sound as the lube works its magic, and a bead of liquid builds on the top of my cock.

“Oh… fuck…” I groan as she rubs the tip of her finger in little circles on my glans.

She flashes her tongue at me and grins, and I know she knows how close I am to cumming. Which is how she pulls her hand off at just the precise moment, leaving me exactly on the edge and no further.

I’m panting, desperate, “Please, keep going…”

Charlotte squirts more lube into her hand, and makes to return. But her hand stops at my balls, running her fingers over them, working the lube into them, tugging on them just so gently.

It feels fantastic, but it’s torture, my dick so close to release, so eager for her return.

“Take a picture of your cock,” she says, massaging my balls.

I push the shutter, the photo sloppy and poorly framed. My cock’s in it, though, another stream of fluid oozing from its tip.

She runs a fingertip up the bottomside of my shaft. “That’s a good boy.”

“Ohh…” I groan and shudder.

And then her fist is on my cock, a lazy, casual pumping of my dick. Her silky touch, her play at nonchalant indifference to my ecstasy, her silly little tongue-out grin — she knows how I will react to her every touch, and she knows how to give me what I need. It all builds up and explodes out, pleasure beyond anything I’ve ever before experienced. I grunt, roll my head back, and cum.

Charlotte laughs as she pumps and pumps, making my dick blast load after load into the morning air. My spunk sprays up and oozes out, coating her hand, drenching my hips. I’m a sticky mess.

With her clean hand, Charlotte grabs my camera and takes a picture of me, laying here in my own cum. Then she leans down, sets my camera on the table, and kisses me on my cheek.

“See you around, Joshua,” she says, standing up.

“Why?” I mutter.

She’s crossing back to her room’s balcony, but pauses, looks at me. “Why what?”

“Why’d you..?” I nod at my dick.

“Give you a handjob?” she shrugs, “I dunno.”

She swings the divider back into place, and then I’m left alone with my mess.

Source: reddit.com/r/sexystories/comments/utbien/the_first_time_i_ever_got_a_handjob_was_from_a