• Home
  • /
  • Stories Hub
  • /
  • BDSM
  • /
  • Helpless - His First Time

Helpless - His First Time

We were sitting on the edge of her bed, fingers laced, both staring out into the night sky over the city. It was awkward at first, sitting with her on her bed, but awkward silence quickly turned into lustful energy as soon as I heard her tender voice. What had started as a semi-casual conversation about sex had turned into a heated exploration of kinky desires...things wouldn't dare share with anyone else. But I trust her. That's why I told her my fantasies. That's why we agreed to do this. Immersed in sexual tension, we turn gently towards one another.

"How do you feel?"

Oh, that question. Its torture to expose myself this way, yet the heat of my arousal doesn't fade.

"I feel... shy," I mumble, voice falling soft.

"Yes, my shy boy" she replies sweetly.

She called me 'boy'. My face flushes. No one's ever talked to me this way before. I laugh nervously.

"Maybe 'boy' is inappropriate," I joke.

She ignores it. She's not joking now.

"My shy boy," She repeats with a suggestive laugh, "everything I want to do to you is inappropriate".

Her shameless desire catches me off guard and I'm lost for words. She folds up onto her knees. Now she's just a bit taller...looking down at me, I breathe in this feeling of smallness, the beginning of my submission to her. It's like a dream. I gaze up into her beautiful bright eyes, alight with passion and energy. She wants me. I feel the soft caress of her hand on my cheek as she lights up with a coy smile.

Slowly, she bends down to my ear. I can feel her breath there, teasing me.

"I want to take you on a new adventure, tonight. I want to bind your hands and feel you surrender yourself to me. I want take full advantage of your body. Is that alright with you, love?" She finishes her question with a hot breath and a playful flick of her tongue over my ear that sends shivers down my neck.

My heart is racing, my breaths in anxious pants as embarrassment sweeps over me. I don't know quite what to do or say. I want to make another joke, be cheeky, banter with her...but I also want to succumb to her, adore her, show her how badly I desire her power over me.

She takes my face between both of her soft hands.

"Talk to me, my lovely shy boy" She urges, locking her stare into mine, "How else do you feel?"

"I feel...well...excited, but also nervous. Um...a bit aroused if I'm honest."

"Good, that's normal" She taps her palm against my check gently and plants a kiss on my forehead. "...and, you know, I like it when you're honest with me."

Suddenly she's up, standing by the bed, still starting down on me with that cute, devious smirk, hands on her hips. I stare up with inquisitive eyes, what should I do now?

"Let's start then?" She interjects, as if she can read my uncertainty. "If you want to play with me, I expect you to be as clean as possible"

I shudder at the word 'expect'. I hope I can live up to her expectations tonight.

"You'll go take a shower and come back here in just these," She continues, tossing a pair of black boxer briefs from her drawer, "don't worry they're new."

I nod, and take the soft new underwear into the bathroom. They faintly smell like her from living amongst her panties. How long had she saved this gift for me?

I shower, well, intent not to fail my first task as her submissive. After my shower, I towel dry and dress as I'd been instructed. Adjusting my hair in the mirror, I realize just how naked I feel, even not being totally unclothed. I'm really going to do this. It'll feel like regular sex, right? Not too different. What if it's different though, or better even? I've got to stop overthinking this.

With a deep breath, I re-enter her bedroom and find her sitting on the bed again, but in a new outfit. A tight black and purple dress hugs her hips and displays her full breasts. Her long legs are bare and crossed. They end with slick black pumps. Her long hair is pulled up in a high pony tail. She's still smirking.

I'm taken aback by her, and feel heat rushing to my cock just from staring. God, we haven't even touched yet.

"Sit with me, darling," she beckons, patting her white comforter. She seems like such a pure girl. And now...well...

I obey silently.

She traces my lips with her finger, "And you say...yes, Miss."

"Yes, Miss"

"There we go," she coos.

Beside her is a pile of braided cotton ropes. She unravels one and looks into my eyes.

"Give me your wrists please, palms up."

I almost forget to respond, she's got me breathless. "Yes, Miss."

As she expertly coils her soft rope around my wrists, She asks if I remember our safeword.

"It's red, Miss."

"Good, and if you say it again, what happens?"

"We...we stop."

"Yes, I will stop, untie you, and we'll talk about it without any judgment or shame."

She finishes with a knot and lifts my wrists to admire her handiwork. For a moment, we both admire the aesthetics of my tanned skin bound by her white rope.

"You've never been tied up before," she observes, "how does it feel?"

I search for the right way to describe it but can't find the words.

"It feels good, Miss."

But it doesn't just feel good. It feels hot, exhilarating, and terrifying... like securing the harness on a rollercoaster.

She smiles, pleased by my answer and proceeds to pull my hands above my head and secure them to her headboard.

I struggle a bit to test the ropes, and feel a steady resistance. This is really it. I'm nearly naked, tied up before her, helpless. She stands to admire her work.

"Look at you there, squirming and bound for me." She laughs, playful and taunting. "Now, I can do anything I want to you and you can't do a thing about it."

I feel my breath hitch at her words. Anything she wants. She climbs back onto the bed, straddles my hips, and begins rocking slowly against my growing cock. I let out a slight moan as I close my eyes and feel her warmth against me.

I feel her fingertips lightly press against my closed eyelids as she whispers, "good idea."

My pleasure abruptly stops and I jerk towards her as she stands up again.

"Silly," she teases, "you're stuck there."

She returns with a black blindfold, "lift your head."

She secures it in one swift, skilled motion and my world is dark.

"Brilliant, isn't it?" She enthuses, "total darkness. Just relax now, just feel."

She's right, my world is dark, and it's as if I can suddenly feel my entire body more intensely. The air is heavier; my hair is on end, my senses primed. I urge my muscles to relax as she said, and take a few deep breaths, anticipating where I'll feel her touch next.

It's my chin. Two soft fingertips urge it upward and hot breath floats over my exposed neck. She breathes warm kisses down my throat, one by one. Around the side of my neck, they become deeper, harder. The hot pressure of her as she continues up my neck begins to overtake me and I sign audibly. She giggles, as her lips approach my ear. She traces her fingertips through my hair as she whispers and sighs into my ear. Tingles of pleasure shoot though my body.

"Don't...kiss...me..." She moans between lusty pants.

Confused, I nod, "Yes, Miss"

She brushes her fingers down my cheek, and follows them with a trail of quick, sweet kisses, leading to the corner of my lips. I pucker them, expecting her to kiss me.

"What did I say?"

I relax my lips, "Don't kiss you, Miss"

She repeats her kisses down the other side of my face, to my lips, but I remember to keep them still.

"What a good listener you are"

Her kisses begin to linger across my forehead, eyebrows, down my nose, chin, across my jawbone. Each kiss seems heavier than the last as I struggle not to move kiss her back. A frustrated moan escapes me.

Suddenly, I feel her peck a kiss onto my starved lips and I sigh again.

"Kiss me back, now" she commands.

She sinks her lips into mine, and we finally kiss. I forgo my technique, hungry for her, and she matches my enthusiasm with a fervent passion. She weaves her hands through the back my hair and lifts my head towards her as our tongues meet but I'm reminded of my limitations as I jerk to touch her back. I'm hers completely. Just feel, she said, so I do.

Our kiss comes to an end; she pulls away, and straddles my hips again. Now, my cock is rock hard as she rocks her hips against me, pleasuring herself. I wriggle beneath her, longing to be touched, to get off.

"Patience, dear" she purrs, "you'll have to earn it"

She unhooks my blindfold and slides it off my face. My eyes wince at the sudden light, but when I regain my sight, I see her standing above me, smiling again. She lovingly removes my bound wrists from the headboard, and ties the rope from them to the foot of the bed, securing my hands together at my pelvis, my fingertips just barely able to graze my cock, trapped within the fabric.

She pulls her leg over my head, exposing herself to me. I take in the scene of her bare vagina displayed for me, eager lips moistened, clit swollen. I begin to instinctively graze my fingers over the portion of myself that I am allowed to reach.

"Touch yourself if you want, but you best pay attention to me."

I nod, blushing that she caught me touching myself. Surely she knew, she tied my hands there after all.

She runs her finger through her lips, gathering up her juices and shows me the glistening result before sliding her finger into her own mouth, moaning in delight. Its torture to watch her, all I want it to touch her, taste her, touch my aching cock.

But I can't touch her. I can't do anything but watch her fingers grace through her lips, wet and glistening. Will she let me taste her? I lick my lips in anticipation. She notices.

"Oh?" She asks with a playful tone, "Would you like to help?"

I don't know what to say. My mind races... What's the right answer? I've never done this before. But, I mean, do I want to lick her dripping pussy? Of course I...

"I..."

"I want your honesty." She reminds me.

"I do. I mean, I would."

"Then ask."

I feel my throat dry and my words escape me as the embarrassment of admitting my desire fights with the sexual tension she is expertly building inches from my face.

She giggles, "I can wait for your answer" and speeds up her rhythmic rubbing, beginning to moan, threatening to orgasm.

"but not for long."

A whimper escapes from the back of my throat, "Please..."

"Very good first try, pet. More earnestly, now."

"Please!?" I call to her, feeling my sexuality overpower my nerves.

She moans again. "Mmm, it's gonna be too late soon. I'm gonna cum all over that pretty little face and you're never going to get a chance to taste this." She removes her finger and glides her juices over my lips before returning to work on her dripping pussy.

Oh god, the taste, I lick my lips and take in the sweet tanginess of her. My world is focused on her. I need her. I need to taste that sweetness again. I reach my tongue out and just barely graze the moistness of her inner labia. She jerks away, angered.

"What did I say? Put your damn tongue back in your mouth. If you want it, you have to ask very very nicely."

"Please, PLEASE" I beg.

"Please WHAT? She demands.

I weaken.

"Miss...Please let me lick your pussy."

She lowers herself closer within my easy reach and I breathe in her warmth.

"Lick"

I don't need to be told twice. I slide my tongue between her lips and am overwhelmed by her. She moans out sweet sensitive whimpers of pleasure.

"Don't stop, boy."

I wouldn't dare. I melt into the warmth of my isolation. Her heat, moans, sweetness, and dripping pussy make up my entire world. I draw short but deep breaths and purposefully keep my enthusiasm high for her. I'm making her happy. I won't stop.

I swirl my tongue in circles around her clit and feel her hips rock in response. As she begins to fuck herself against my tongue, I fight the urge to swim inside my head, to float away on the high of feeling trapped and submissive. I have a job to do and Miss needs my full attention.

She rocks against my tongue a bit faster and lets out sexy whimpers of pleasure, her face relaxing.

"Make me cum, gorgeous. All over your face. Come on."

She responds to my increase in pressure and speed and jerks a bit before letting out a long moan. She pauses, and lifts up a bit off my face, allowing me to catch my breath.

"You're such a good boy" she pants, smiling in satisfaction, "...and very patient. I think you've earned a reward."

I squirm, aching for satisfaction of my own. She takes my wrists.

"I'm going to bind your arms a different way, lay still."

She detaches my wrists into separate bondage and pulls them straight out to my sides, securing them to either side of the bed. Satisfied, she sits between my legs and begins to work off my underwear, finally freeing my desperate, throbbing cock.

She brings my underwear close to her face and breathes in deeply. "My my," she taunts, "these are soaking with pre-cum...smell."

With a flash of discomfiture, I smell myself on the underwear she pressed against my face. She returns it to her own face and runs her tongue up a wet stain. I shudder, watching her suggestive smirk as she tastes my arousal.

"You taste hot"

I blush

She picks up a white jar from her nightstand, and opens it, pouring the clear slick liquid into her palm. She rubs her palms together, warming the lube, and starts to work it into my cock, wrapping her fingers dexterously around the shaft, to the tip, down again all the way to my balls. She cradles them in one hand, twirling her fingers into the base of them. Her other hand goes to work on my shaft, gliding and twisting up around. My breathing hastens and I start to urge my hips forward into her rhythm. I hum in pleasure at her movements, my cock pulsing in gratitude.

"You like that?" She asks playfully, picking up her pace. "Don't cum yet, I still have to give you your present."

Present?

She reaches to open her night stand drawer and pulls out a jet black silicone strand of anal beads, smirking familiarly.

My heart jumps. I didn't expect this, I'm not ready.

"I...Miss, I don't know if I'm ready"

She places the toy in my hand, the balls are stiff with a little give, each ball slightly bigger than the last, ending in a little ring, for her finger.

"It's okay," She assures me. "We're going to do it together and it's going to be incredible. Anytime you want to say your safe word you can."

I nod. She takes the beads from my hand, covers them in her lube and swirls the first, no larger than a pea, around my sphincter. I tense up, hold my breath, but she doesn't penetrate me.

"Just relax, pet, just feel good"

As she continues, swirling the beads, she also begins stroking my cock once again, swirling up around the tip, making my breath catch in time with her movements.

I feel myself begin to relax, succumbing to her pleasure. I gasp at a sudden nudge of pressure. I tense up again, but this time a pea-sized intruder halts my instinct. Oh my god, she did it. It didn't even hurt.

"The more relaxed you are, the better it will feel," she advises me, keeping up her steady tempo. "They only get bigger."

Grateful for her coaching, I make an attempt to relax. –pop –pop. Two slightly larger beads join the first with two quick pushes. Her tempo picks up.

I pull my attention away from my ass and focus on her delicious attention to my cock. Pumps of pre-cum join her lube, creating a warm, wet heaven. –Pop –Pop Two more, I moan and struggle against my bondage, feeling totally helpless beneath her, beginning to feel overcome by sensation. She's working tirelessly on my cock and talks to me in a playful yet soothing voice.

"You feel full, don't you?"

Full. Yes. That's it, that's this feeling.

"Yes, Miss"

-pop –pop

"Fuck! That hurt!"

"Oh, I know those last ones are big, but you can handle this." She nods at me, adding more lube around my asshole. "Take it for me, darling."

I nod, close my eyes, and choose to believe her. I can no longer feel how deep the beads penetrate, but I know there are two left and I don't know when they're coming. Relaxing is proving difficult.

She adds her second hand to my cock, masturbating me in tandem with the other. I gasp at the doubled sensation, tilting back my head in pleasure. –Pop –pop.

"Oh god!" I cry out, the biggest beads invading my asshole, stretching me, sparking an incredible jolt of pleasure and pain.

"That's it, that's all of them."

Her hands speed up, pumping my cock, urging me to cum. I moan into her movements and surrender myself to her.

"Cum for me, darling," she beckons, "and tell me when you are."

Fast and steady, I feel myself ready to explode. Yes. Please. Don't stop.

"Yes. Please. Don't stop."

I have no doubt now, no shyness; I am totally engulfed in lust. Outstanding bliss meets unbearable tension.

"Miss, I'm gonna cum"

"Cum for me"

I burst, and in a swift motion, she switches back to one hand, hooks her finger through the ring of the beads, and jerks forcefully. A second wave of deep explosive pleasure like I've never felt before echoes through me and I scream at the shock of it.

She smiles, satisfied, and finishes slowly pumping the remaining cum from my exhausted body.

"You're so good" She chants to me.

I lie still and speechless as the wave of newfound pleasure resonates within me. She gently wipes my cum off my chest and off her own with a towel, then unties my hands before letting down her hair and cuddling up next to me. I feel myself floating, slowly gliding down to earth from an incredible high.

"Feeling happy?" She inquires, petting my hair.

"Incredible," I kiss her forehead and feel her relax into the crook of my arm. "Thank you."

Drained, we start to drift off to sleep together. But, when we wake up, it's going to be my turn to be the boss.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • BDSM
  • /
  • Helpless - His First Time

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 62 milliseconds