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Helpless - His First Time

"She introduces him to the thrill of bondage"

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I can’t even remember how long I’ve been sitting on the edge of her bed - funny how time slips by when your fingers are laced with those of a beautiful girl. Her beauty is so intense that my eyes are repeatedly drawn away from the view of a sparkling city under the night sky. It was, admittedly, a bit awkward at first to be sitting with her on her bed, but awkward silence quickly turned into lustful energy at the sound of her voice, so disarming and tender.

What started as a semi-casual conversation about sex had turned into a heated exploration of kinky desires... things I 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, she turns gently towards me and I follow her lead.

"How do you feel?" Her voice melts through the silence.

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

"I feel... shy," I mumble, more softly than I expected

"Yes, my shy boy," she replies knowingly and I am staring back, wide-eyed.

She called me 'boy'. My face flushes. No one's ever talked to me this way before. I don’t feel like she’s demeaning me but I also have no idea what to say…so I laugh. Nervously.

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

She ignores it. She's not joking now.

"My shy boy," she repeats, eyes glistening as a suggestive laugh escapes her, "everything I want to do to you tonight 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 that is finally going to happen tonight. It’s all been arranged and discussed. So much, in fact, that I feared we’d over-planned and that it somehow wouldn’t be as much fun. But now, in this moment, it all feels like a dream.

I gaze up into her beautiful, bright eyes, alight with passion and hot with energy. She wants me and God, oh God, I want her, too. Just as I twitch a muscle with the thought of touching her, I feel the soft caress of her hand on my cheek. 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." She licks her lips and I feel my breath hitch as she continues, “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 breathing comes in anxious pants as something, perhaps embarrassment, sweeps over me. I am a flushed, horny mess and 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. The dichotomy of emotions swelling within me is almost too much and I don’t meet her gaze until she takes my face between both of her hands, a firm grip under her soft skin.

"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… ”

She waits for me to continue.

“Um... and a bit aroused if I'm honest."

"Good, that's all to be expected," she smiles, satisfied, and taps her palm gently against my cheek and plants a kiss on my forehead. "And, you know, I like it when you're honest with me."

I am warm with pride at her words and almost feel silly for the way they melt into me. Suddenly she's up, standing by the bed, still staring down on me with a cute, devious smirk and hands on her hips. I stare back with inquisitive eyes. What should I do now?

"Let's start then," she interjects. She sounds bossy… serious… and sexy. “If you want to play with me, I expect you to be as clean as possible."

I shudder at the word 'expect' and all I can think is that 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 and it is somehow relieving to no longer wonder about what I should do. She’s tossing a pair of black boxer briefs from her drawer into my hands. "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 has she saved this gift for me?

I shower thoroughly, intent not to fail my first task as her submissive. After my shower, I towel dry and dress as instructed. Looking in the mirror, I realize just how naked I feel, even not being totally unclothed. I'm really going to do this. I’m going to be submissive and kinky and it’s going to be fine. There’s no reason to be nervous, I tell myself. It won’t be too different from regular sex. Except, what if it is different? Or, what if it’s better?

I decide that I've got to stop overthinking and, with a deep breath, I enter the bedroom and she is sitting on the bed again, but in a completely different outfit. She’s changed for me, too, and the thought makes me grin stupidly.

A tight black and purple dress hugs her hips and displays her full breasts. Her long legs are bare and crossed and slick black pumps are on her feet. Her long hair is up in a high pony tail. She's still smirking. I'm taken aback by her, and feel heat rushing to my cock. God, we haven't even touched yet.

"Sit with me, darling," she beckons, patting the comforter. On the fluffy white bed, 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," I respond quickly.

"There we go," she coos as she runs her hand down from my lips, across my neck and torso and I can’t hide from her as my muscles tense beneath her hand. She can feel every inch of my nervous, eager, arousal. And she can see it bulging in black between my legs. I’ve never felt so naked.

Beside her she’s prepared a pile of braided cotton ropes. She unravels one and looks into my eyes.

"Give me your wrists please, palms up." She is so fucking calm. How can she be so cool and collected when my heart is threatening to burst from my chest?

I outstretch my hands but almost forget to respond; she's got me breathless again. "Yes, Miss."

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

"It's red,” I respond and then remember to add, "… Miss."

"Good, and if you say it again, what will happen?"

"We... we’ll stop?"

"Yes.” She is nodding. “I will stop everything I’m doing. I will untie you, and we'll talk about it without any judgment or shame. You are safe. Do you understand?"

I nod.

“That’s my good boy.”

She finishes with a knot and lifts my wrists to admire her handiwork. I take it in, too. My tanned wrists are bound together by her white rope, creating a contrast that really is something special. The rope is knotted so neatly I wouldn’t want to untie it even if I knew how. I pull my wrist apart at the bondage and it holds. The ropes don’t loosen or budge at all. Incredible.

"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." I manage. But it doesn't just feel good. It feels hot, exhilarating, and terrifying... like securing the harness on a roller coaster. How do I find a way to describe it?

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

I struggle a bit to test the ropes again, and feel a steady resistance. This is really it. I'm nearly naked, tied up before her, helpless - really helpless. The feeling is nothing short of incredible. She stands to admire her work.

"Look at you there, squirming and bound for me." She laughs, playful and teasing. "Now, I can do anything I want to you and you can't do a thing about it. Does that make you nervous, my boy? Or does it make you fucking hard?”

I feel my breath hitch at her words. Yes. Anything she wants. She climbs back onto the bed, straddles my hips, and begins rocking slowly against my growing erection.

She feigns a gasp when she feels how hard I’ve already become and leans down low to my ear.

“Slut,” she lets out the word in a slow hiss and I melt for her. I hear myself let out a moan as I close my eyes and just feel her warmth against me – just let her have me.

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 but I am held back by ropes.

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

I’d almost forgotten that I was tied. The second realization brings a new heat of arousal and excitement.

She has 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, "I love this one. It blocks how every trace of light. Now you can just relax. 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, and take a few deep breaths, trying to anticipate 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 sigh.

“Rule number one,” she giggles, her lips close to the side of my head. She traces her fingertips through my hair and whispers and sighs into my ear. Tingles of pleasure shoot though my body.

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

Confused but eager to please, 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 just say?"

I relax my lips, "You… not to kiss you, Miss." And I suddenly realize the game she is playing with me. I feel my face get hot. She is toying with me and I am allowing myself to be toyed with. Why is this turning me on so much? My cock aches and I find myself wishing she would straddle my hips again.

She repeats her kisses down the other side of my face and all the way 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 kiss back. A frustrated moan escapes me.

I hear her giggling again and shift my hands, taking in the helplessness of my situation once again. It is so, unbearably difficult to keep my face relaxed as she kisses, licks, teases, and blows over me, taking her time to enjoy my predicament and relishing every strained sigh.

Suddenly, I feel her peck a kiss onto my starved lips and I produce a grunt that is almost primal. God, I am putty in her hands.

"Kiss me back now," she commands.

She sinks her lips onto mine, and we finally kiss. I forgo any 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. The reminder of my limitations as I jerk to touch her back has become a sweet and welcome feeling. 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. My cock is rock hard as she rocks her hips against me, humming with her own pleasure. I wriggle beneath her, longing to be touched, to get off.

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"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 boxers.

She lifts a leg over my head, exposing herself to me and I find that I am grateful. I savor the scene of her bare sex displayed for me, eager lips moistened and 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, boy, but you best pay attention to me."

I nod, blushing that she caught me touching myself. Surely she expected it; 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. It is a strange, delicious torture to watch her. All I want is to feel her, taste her, touch my aching cock and she is keeping control over all of these things. The very idea makes me hot all over and pulses of pre-cum tease at the fabric of my underwear.

But I can't touch her. I can't do anything - except watch her fingers grace through her lips, wet and glistening. I am obsessed. I have to taste her. I lick my lips in anticipation. She notices.

"Oh?" she asks with a playful tone, "would you like to help?"

She is such a tease. I need it. I need to taste her. I don't know what to say. My mind races. What's the right answer? I've never done this before. But, I mean, I want my tongue against her, God, right in my face. Of course, I...

"I..."

"I want your honesty," she reminds me.

"I do. I mean, I would."

"Then ask."

“What?” I manage.

“Ask for what you want, politely and properly like a good boy.”

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. My breathing speeds up as I try to put together letters into words into a sentence that will please her. I’m so nervous.

"I can wait for your answer," she giggles, " but not for long." She speeds up her rhythmic rubbing, beginning to moan, threatening to orgasm.

A whimper escapes from the back of my throat. "Please..." my voice is higher, softer than I expected.

"Very good first try, pet. Give it another go, more earnestly, now."

"Please!?" I call to her, this time a little to desperate as I feel my sexuality begin to overpower my nerves.

She moans again and now she is simply taunting me, enticing me with her tongue. "Mmm, it's gonna be too late soon,” she sings. “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 now dripping pussy.

Oh God, the taste, I lick my lips and take in the sweet tanginess of her. My world is focused on her. There is no one, nothing, but her. I need her. I need to taste that sweetness again. I am a hungry animal. I reach my tongue out and just barely graze the moistness of her inner labia. She jerks away, angered.

"What the hell did I tell you?” she almost yells before talking on a deep whisper. ”Put your damn tongue back in your mouth. If you want it, you must ask. Let me hear you say it.”

"Please, please," I beg.

"Please what?” She demands.

I weaken.

"Miss...” I inhale. “Please, let me lick your pussy."

Like magic she complies. She instantly lowers to 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.

"Oh, my boy. Don’t stop.”

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

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 feel the urge swim inside my head, to float away on the high of feeling trapped and submissive. It is such an enticingly blissful offer but I must fight it for now. I have a job to do and Miss needs my full attention.

She rocks a bit faster against my tongue 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 hard against my face 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. "You were very patient. I think you've earned a reward."

I squirm, aching for satisfaction of my own. She takes my wrists and I let her lead me.

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

She detaches my wrists into separate bondage so gracefully and efficiently that I am actually impressed. She pulls my arms out to my sides, securing them to either side of the bed. I am suddenly exposed in a whole new way and more immobile than ever.

Satisfied, she sits between my legs and begins to work off my underwear, finally freeing my desperate, throbbing cock. And there I am, bound and naked for the first time before her. A shiver runs through me. Nervous, excited, hot, desperate, submissive.

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

With a flash of discomfiture, I smell myself on the underwear she has pressed against my face. It isn’t the smell that turns me on, but the way she seemingly carelessly rubs my own mess onto my face and leaves it there, knowing I can’t reach up to wipe it off… knowing I have to lay there and take whatever she gives me... knowing how much I fucking love it. She returns the cloth 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 so hot."

Four simple words but they’re enough to make me blush.

She picks up a glass 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. God, I don’t want to say that safe word thing. I don’t… but I just…

"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 feel incredible. Anytime you want to say your safe word you can. Trust me."

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 feel good, pet. I’m not going to do it until you’re totally relaxed."

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

I 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. And then her voice gets that familiar playful edge. "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. It still doesn’t hurt and I feel immeasurably relieved.

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. The pressure, the unrelenting pressure in my ass makes her every stroke so much stronger and deeper. She's working tirelessly on my cock.

"You feel full, don't you?"

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

"Yes, Miss."

“Embrace it.”

-Pop –Pop

"Fuck! That hurt!" I feel my ass clench and it only adds to the pain.

"Oh, I know these last ones are a little big, but you can handle it." She nods at me, adding more lube around my asshole. “Stay relaxed and open for me.”

So 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.

“Deep breath, love.”

Oh, God…

–Pop –Pop.

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

"Well done, sweet boy. Keep breathing."

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 as you do."

Fast and steady, full and throbbing, exposed and helpless, 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.

"Miss, I'm going to c... " I nearly scream at her.

"Cum for me," she says.

I burst, and in a swift motion, she switches back to pleasuring me with only one hand, hooks one finger of the other 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.

My orgasm shakes the world and I am floating and falling all at once. I am ripped open and have become the air. I settle slowly, like dust, and she comes back into vision, smiling and satisfied as she slowly finishes pumping the remaining cum from my limp, exhausted cock.

"You're so good," she is chanting to me, “such a good boy.”

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

"Are you feeling happy?" she inquires, petting my hair.

"Just incredible," I sigh. I kiss her forehead and turn to relax into the crook of her arm. "Thank you."

Drained, we start to drift off to sleep and I can’t help but imagine what it might be like if, next time, I could be the one in charge and she would be the one to feel so wonderfully, deliciously helpless.

Published 
Written by RileySapphire
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