Celebrity Sex Stories

Greetings Alanna,

Seeking a favor... (Doesn't turn out as planned)

Spankmasters
May 11, 2024
16 min read
bondageorgasm controlneighborteaseHey Alannachastityfemdom
Hey Alanna
Hey Alanna

Greetings Alanna,

Ever since I was in high school, I've dreamed about being dominated sexually by a gorgeous woman. Not something extreme, but the thought of having my sexual pleasure completely controlled by someone else shaped several of my fantasies throughout the years.

Six months ago, I bought a chastity cage with the goal of securing it onto me and giving the key to my neighbor Alanna. The one thing I haven't decided yet is whether to tell her what the key is for.

Alanna is a 26-year-old with piercing blue eyes, dirty blonde hair, an athletic frame, and a dazzling smile that can immediately make a guy fall to his knees. She works as a physical therapist, which showcases her active lifestyle. Her fit body suggests that she spends a lot of time training at the gym.

I'm two years younger than her, working as an accountant, and maintain a regular exercise routine myself. I'm not a lazy person. However, growing up with a strained relationship with my mother led to me being a bit awkward around girls and lacking self-confidence when it came to forming intimate relationships.

Although we've had a friendly connection for the last six months since I've moved in, I've been debating whether to ask her for this favor.

But today's the day. I locked the cage on my penis yesterday afternoon and prepared to ask her.

So there I am, bringing out the trash, and I see her loading a beach chair into her car. I take a moment to appreciate her long legs and admire her toned rear end.

"Just do it," I whisper to myself.

"Hey, Alanna," I interrupt her, before I even realize what I'm doing.

"What's up?" she asks, looking towards me with a casual grin.

"Can you hold onto this for me?" I approach her and hand her the key.

"Sure," she nonchalantly replies, clipping the key onto her keychain. "What is it for?"

"Something important, but I'd rather not say."

"Alright, I won't ask," she winks. "I'm glad you trust me; I'll keep this safe."

"Thanks," I say, nervously smiling.

"I'm going to the beach today," she says, smirking. "Want to come?"

"No, I think I'll just stay home and relax today."

"Suit yourself," she says, walking away.

I re-enter my house a few minutes later, and the reality of giving her the only key to my cage begins to truly dawn on me. I feel my cock twitch as she drives off.

For the next week, I relish the feeling of being in chastity while she holds onto the key.

On a Saturday afternoon, a week after she received the key, Alanna unexpectedly stops by my place. I open the door to find her wearing a sleeveless pink top and khakis.

"I need some help moving something," she asks.

"Of course," I grab my keys and leave my house.

--

"Thank you so much," she says, walking in front of me. I glance at her curves and then back up to her face. "Sorry for bugging you, but I really needed the extra help."

"It's not a problem at all," I say, admiring her well-toned derriere.

As we approach her living room, my gaze shifts from her buttocks to her face.

"While I'm here, could you please return my key?" I ask.

"Sure," she answers, fetching her keychain from the coffee table. She unclips the key and holds it between her red-painted nails. "One mystery key for the accountant genius."

I reach for the key, but she snatches it back, her eyes gleaming mischievously.

"What's it for?" she inquires.

"I told you I didn't want to tell you," I say nervously.

"Well, I heard what you said," she sits down on the edge of her bed with her legs crossed. "And what I'm saying right now is..."

She looks at me intently as I anticipate her response.

"Give me the key," she bossily demands.

I comply, placing my hands behind my back. She examines my naked body, now completely exposed.

"Now, tell me what it's for," she sternly declares.

I squirm as she tilts my head up to meet her eyes.

"It's for my chastity cage," I confess in a small voice.

"Got it," she says softly.

Well, I don't know what I was anticipating, but it wasn't this.

I follow her into her bedroom, where she sits down on the edge of her bed.

"Strip," she commands.

I strip and attempt to obscure my trapped nothingness. But she snaps her fingers again.

"Hands behind your back," she orders.

I submit, and she studies my body that is now completely exposed.

She starts circling around me, running a hand all over my body.

"Wow, you've got a nice physique here," she whispers in my ear. "You see, we can help each other out in this situation."

"How so?" I stutter with fear in my voice.

"Well, based on what I see, you seem comfortable in submission," she gently touches my guard. "And in me, there's a dominant side." My heart starts racing as she speaks. "And it's been a while since I got to dominate a man," she moans in my ear.

"You're not upset?" I ask, trying to catch my breath.

"Not at all," she responds, settling back down and running her foot up my leg.

For a moment, we're both silent as I stare at her and she stimulates my cock with her foot.

"Okay with my plan?" she dares to ask, staring me in the eyes. I nod, hormones and nervousness preventing me from speaking. "Kneel," she orders me.

I obediently kneel before her. "Kiss my foot," she instructs, placing her foot on the floor in front of me.

"B-But I can't-"

"I don't care," she interrupts me.

I hesitantly lower myself and kiss the top of her foot.

"Noted," she says rising. "In this house, you're to call me Ma'am." She leans close to me. "Is that clear?"

"Yes Ma'am," I respond, peering at her cleavage.

"Good boy," she kisses my forehead. I let out a low groan as she rubs her foot over my guard.

"Stand up," she barks. "Hands behind your head," she wants to see my aroused state. "I want to check out my new slave up close."

"Yes Ma'am," I quietly say, putting my hands behind my head,

"What are your preferences?" she queries.

"I want to feel teased and inhibited... and controlled," I softly answer. "But I don't want to be ridiculed, degraded, or abused."

"Excellent," she says face-to-face with me. "Fortunately, humiliation isn't genuinely my thing." She stands in front of me. "But teasing a guy... totally is my thing," she strokes my guard.

"Yes Ma'am," I agree.

"You have any questions?" she inquires in a lighter tone.

"Will you keep me caged for a while?" I hesitantly ask.

"I'm undecided right now," she flings her hair. "But remember, your cock is mine once it's unlocked. It'll depend on my whims."

"Yes Ma'am," I reply.

She crosses her arms. "Your orgasms will also depend on me and when I want you to ejaculate."

"Yes Ma'am," I gasp, feeling a mixture of arousal and fear.

"Just be aware," she tenderly hugs my cheek. "You wanted this." She smirks at me. "I did too." I can't help but nod as I hold her gaze.

"Yes Ma'am," I hardly whisper.

She glares at me, serious in her tone, and says, "Remember, you wanted this."

"Yes Ma'am."

She struts to her closet, opens it, and pulls out handcuffs. She zips to my side, and in a flash, cuffs my wrists to the front of my body. Then, she pulls on a chain and hooks it to a hook on her bedroom door.

Before I know it, she's kissing me passionately. Our lips meld as we kiss, and we pull apart both short of breath.

"Shit," she puffs. "I've been dying to do that."

I gasp, "Me too."

She returns to her closet and pulls out a chain with a key. She clips the necklace onto it and strides back to me.

"Do you like it?" she tilts her head.

"Yes Ma'am," I answer.

"Good," she kisses my forehead. "Do you enjoy eating pussy?" she inquires with a raised eyebrow.

"Yes Ma'am."

"Excellent," she smirks, playing with her key. "Because I think I need an instrument for-"

"Yes I'll do it for you Ma'am. Anything Ma'am. Please-," she squeezes my buttocks after I interrupt her.

"Next time you interrupt, you'll be locked away for an entire extra week." I nod in acceptance.

"Yes Ma'am," I reply as she releases my face.

She grabs my handcuffed chin and unclasps one of the cuffs, violently pulling my bound arm behind my body, and cuffs it again.

"Kneel," she softly requests, not a hint of the aggressive tone from moments earlier. I comply and she undoes the zipper on her khakis. "Make me cum," she demands, clenching onto my hair.

A few minutes later, she climaxes as I suck on her clit.

"Good boy," she leans down and licks up her juices off my face. "And what a great tongue," she whispers as I clean up her fingers.

"Thanks, goddess," I meekly reply as she pulls her hand out of my mouth.

"Now," she leans against the door. "I'd love to liberate you and screw you until I cum on your rigid dick," she smirks, noticing the leaking pre-cum.

"Uh-," I catch myself before I interject again.

"But you're going to spend the next week in chastity for me," she smirks. "As punishment."

"Punishment? For what goddess?"

"For attempting to use me for your kinky little thing with yourself," she leans down and whispers in my ear. "Understood?"

I glance at the floor, a combination of shame and comprehension.

"What do you say?"

"I'm sorry goddess," I hesitantly comment while attempting to maintain eye contact with her.

"You are forgiven," she runs her fingers through my hair. "But you'll still serve your week as a repercussion."

"Yes goddess," I respond, looking back at the floor.

"Good boy, now get dressed."

I carefully dress myself and insecurely walk towards her. She browses an eyebrow, as if to inquire my purpose. I can't form a cogent thought, so I embrace her.

"What do you say?" she sweetly inquires.

"Thank you, goddess," I answer.

"You're welcome pet," she strokes my back.

I return to my house, simultaneously embarrassed and content.

The upcoming week becomes both the most exciting and irritating of my life.

The manner she smirks at me every time we encounter each other fuels my arousal. However, watching her beautiful body and recognizing she has my key creates a sensation like my feelings from the previous week on steroids.

On Thursday night, approximately 9:30 happens.

I approach her front door. I knock on the door. No answer emerges for several minutes and I knock again.

I sense my phone vibrating. Another message from Alanna.

"Side door. Code 4698"

I walk to her side door and input the password. The door opens and I nervously enter the house, relocking the exit door.

I ascertain a blindfold on the kitchen island and a handwritten message.

"Put it on." I place the blindfold on and tremble in anticipation.

A few minutes later, I detect high heels clicking on the wood floors.

"Good boy," she whispers and takes my hand in hers. "Follow me," she starts walking.

"Cautious on the stairs," she says softly, leading me up the stairs.

We attain the top of the stairs and she releases my hand.

"Disrobe." I remove my clothing and feel her around me, caressing my body.

"Appreciate the gym this week?" she caresses my bicep.

I nervously breathe throughout her exploration.

"Wonder if I'll disclose my goddess?" she licks my earlobe.

"Yes goddess. Please," I whimper as she plays with my nipple.

"Up against the door," she gently says, pushing me towards the door.

I secure my wrists and ankles to the door.

"So," she places a hand on my chest and leans into the door. "Anything to confess to me?" she whispers in my ear.

"Yes goddess," I whisper.

"What's the issue?"

"I'm regretful I tried to employ you in my match goddess. I should've been honest with you," I whimper as she tweaks my nipple.

"Good boy," she kisses me and struts away from me, caressing the cage and teasing the lock.

I gasp as she removes the blindfold.

She brags a pink leather halter top, black leather pants, pink high heels and boasts my key hanging from her necklace.

"Well, have you anything to utter?" she displays the key between her manicured nails.

"You seem flawless goddess," I state, my swollen dick throbbing in spite of its confinement.

"Thank you slave," she smirks, sauntering in front of me. "How do I look?" she asserts, taunting the enclosure.

"It's aching so much goddess," I say as she palpates my balls.

"I suppose that's the case," she kisses my cheek. "Time for the chastisement," she smirks, "How long has it been since you've gone two weeks without ejecting?"

"I can't recall goddess," I pant.

"Listen," she kisses me. "By the way, how about three weeks?"

I jerk, "No please no."

"Take it easy, I'm just playing around," she whispers to me, leaning in for a kiss on the cheek. "I still haven't decided whether or not you're going to cum," she says with a smile. "So, tell me, how many orgasms do you think I've had this week?"

"More than me," is all I can manage to reply.

"Yes," she chuckles. "I have in fact had more than your zero orgasms."

She releases my ankles and stands up, untying my wrists as well.

"On the bed," she instructs.

I lie on the bed, flipping onto my back, and she ties my wrists and ankles down.

She puts a finger over my lips to silence me and climbs on top, binding my hips.

She kisses me passionately. "What shall I do with you?"

"Fuck me," I plead.

"Hmm, that's an idea, but not yet," she says more seriously. "Give me that tongue of yours," she pulls her pants down and plops herself onto my face.

Her moans grow more intense as I lap at her with my tongue. After a few minutes, she starts to grind on my face.

"Fuck fuck fuck," she cries out as her juices coat my face. She comes with a shriek, lifting herself off of me. "Again," she breathes, lowering herself back on top of me.

My throbbing cock drips with pre cum as I continually lick her. After a minute, I flick her clit with my tongue and she cries out as she has another orgasm, coating my face with her juices.

She places a hand over my mouth and lies down next to me, catching her breath.

"Holy shit," she barely gasps. She raises her head, exposing her flushed cheeks. "I've never been licked like that before," she kisses me deeply.

"Please," I whimper, feeling the torture of the steel cage pressing against me.

"What do you want?" she teases, tapping the cage lightly.

"Please unlock the cage, my Goddess," I beg.

"That's an intriguing suggestion," she purrs, holding up the key. "So, what do you want me to do with your cock when I free it?"

"Please fuck it," I whimper, feeling the denial of release.

She strokes my cock gently, smiling mischievously.

I groan in pleasure as she wraps her hand around my cock and pumps it slowly.

I simply enjoy the sensation until she releases my cock.

Just as I mumble a plea she puts her hand over my mouth again.

"No begging," she reprimands sternly.

I nod in understanding, and she gets off the bed. I admire the way her leather pants hug her curves as she opens her closet. She pulls out a vibrator and removes her pants.

She sits on my chest, turning the vibrator on.

I watch as her facial expressions change as the vibrator stimulates her clit. She grinds on my face, crying out as she comes, some of her juices covering my face.

"Did you enjoy that show?" she says teasingly as she licks my face clean.

"Yes, my Goddess," I answer softly, my cock dripping with anticipation.

"So," she says sitting up. "I think I want a cock inside me." My eyes alight at her words, and I nod enthusiastically. "So, if I fuck you, will you be able to last, or do I need to numb your cock?"

"I can last, my Goddess," I beg, desperate for release. "Please don't numb me."

She silently touches my cock with a finger. "So you want me to fuck you?" she moans. "You want my pussy wrapped around your frantic cock?"

"Yes, my Goddess," I gasp as she pinches my frenulum.

"Beg me," she says, sitting back between my legs.

"Please, my Goddess, please please please, my Goddess," I chant, feeling the intense desire building. "Please... fuck... me, Goddess."

I moan as she holds my cock down against my stomach and straddles me, rubbing her pussy against it.

I groan in pleasure as I feel the wetness from her pussy leak onto the head of my cock.

"I didn't tell you to stop begging," she says, rubbing the pre cum on my stomach.

"Pl... please... fuck... fuck fuck," I lose control as she continues to grind on my cock.

"Oh come on," she says, attempting to suppress a laugh. "Surely you want to fuck me enough to beg through this," she rubs her clit while using the vibrator.

I freeze in confusion, then scream out my pleas. "PLEASE." I cry out so loudly that I think the whole neighborhood can hear me.

I moan as she hovers her wet pussy above my hard cock. She rubs it gently, making me writhe with pleasure.

"I think I'm going to allow it," she smirks. "Do you want me to fuck you?"

"Yes, my Goddess," I answer, feeling my hips straining against the binds.

"Good," she says, rubbing my cock and pinching my nipples. "Get ready to be taken, slut."

My eyes light up with hope as she lines my cock up with her pussy and slides down onto me, moaning loudly as she fills herself with me. "Goddess!" I cry out as I feel her heat engulf me, her pussy squeezing me tightly.

"Inside me," I beg, arching my back.

"Me too," she replies, rocking her hips slowly. She sighs in pleasure, "I never wanted to try anal but seeing you fuck others makes me want to try."

She shifts around her hips, positioning her ass over me. "Please, Goddess, I'm ready," I plead, teaching myself to relax my sphincter.

She positions her ass over me, teasing me with her wet pussy before slowly sliding down onto my cock. "Yes, I'm here, within you," she says. "I want to cum inside you, sweetie."

She rides me with increasing intensity, her biting her lip, and me struggling against my restraints, but eventually succumbing to the intense pleasure, screaming incoherently.

"Are you going to cum?" she asks, moaning.

"Yes, Goddess, I'm cumming, please cum with me," I plead.

We lock lips, intertwining our fingers, and scream out our individual relief as we both cum, our cries echoing throughout the house.

"Great job!" she sweetly remarks as she lifts her body, positioning her vagina over my dick. "Don't come just yet," she instructs and her vagina envelops my penis.

She groans as she gradually lowers herself onto half of my cock. My dick is twitching inside her vagina, and I'm eager to penetrate her even more deeply, but my hips are tightly secured.

She leans over to kiss me, but she doesn't lower her hips.

"Please," I implore with tears in my eyes.

"I think I might climax simply from your twitching inside me," she moans dramatically. "Let's discover that," she kisses my cheek.

"No no please. Please, Goddess. I'll do whatever you want. Please just have sex with me," I whimper.

"Anything?" she teases, slightly lifting her hips.

"Yes," I give in. "Anything. Just have sex with me."

"You'll be back in that cage before you leave this house."

"Yes, Goddess. I'll do it," I weakly respond as she wipes away my tears.

"Good boy," she praises me before kissing me fiercely.

I shout with incredible pleasure as she slowly grinds on me.

We both groan for several minutes before she stops moving her pelvis.

"Why'd you s-," she interrupts me with a powerful kiss that could knock someone over.

"Does my vagina feel as satisfying as you thought it would?" she inquires with a tilted head.

"Hell no. It's even more delightful than anything I've ever fantasized about," I reply, feeling my vagina constricting around my desperate penis.

"Good response," she says before my cock starts jerking inside her again.

"Please fuck me some more," I ask cautiously trying to hide my desperation.

"Oh, shit," she groans. "I don't believe I need to," she tosses her head back. "You're going to..." her voice fades out. "Cock... tw... twitch... it's e... extremely..." I sense her vagina contracting on my throbbing penis and she moans in delight.

After a brief moment, she kisses my forehead and climbs off of me.

"WAIT," I plead. "What's going on." She silently reaches for the cage. "No no no no please no," I vainly struggle.

"What's the issue?" she asks with a satisfied grin.

"I didn't come."

She runs a fingertip over my penis. "That might be a problem for you," she lightly smacks my naked penis. "But you never asked." She lifts her eyes to meet my gaze. "Convince me to let you come."

I don't think simply pleading will be effective with her this time.

"Goddess, reconsider," I rapidly say. "I made you feel so awesome tonight." I pause for a second, attempting to gauge her reaction. "Isn't it just fair that you repay the favour, Goddess?"

She silently stands up and enters the restroom. When she returns, she has a rag in her hand. I'm unable to plead anymore; I merely lower my head on the pillow and accept that she's locking me back in the cage without letting me climax.

She sits next to me on the bed. I close my eyes and hope this won't take long.

After around thirty seconds, Alanna starts laughing hysterically.

I open my eyes and gaze at her, struggling to breathe.

"I got you really good," she chortles before she leans over and takes my penis in her mouth.

I moan in surprise as she persistently sucks my throbbing penis, dripping in her mouth.

"Oh fuck," I moan as she astoundingly sucks my penis.

She brings me to the brink of climax, before pushing me back from the edge without raising her head.

"Fuck," I cry as she starts sucking me to the edge once more. "Please," my voice cracks as she lifts her head up.

She wraps her hand around my sensitive penis and firmly strokes it.

"You're going to come," she gently announces as she strokes my penis.

"3," she taps my frenulum with her other hand.

"2," she kisses the tip of my penis.

She discontinues counting for a brief moment but her stroking increases in speed.

"Please," I implore through gritted teeth.

"1. Come."

"Thank you-," I manage to say before I succumb to my orgasm, grunting in happiness.

I regain consciousness from my orgasmic stupor a few minutes later, and she raises her hand to my face.

"Clean me up," she softly says as I lick my semen off her hand.

When she's satisfied with her hand, she grabs the parts of the cage.

My penis hardens a bit as she guides my testicles through the ring, but she disregards it and presses the cage down. She fastens the cage and my penis is already straining intensely.

"Was that enjoyable?" she softly inquires.

"Yes, Goddess," I truthfully respond as she unties my ankles and wrists.

"I thought so too," she chuckles, and I start to move.

I sit on the edge of her bed, my penis already trying its hardest to break free of its restraints. I silently reflect on the evening's events before she gives me a kiss on the forehead.

"Are you okay?" she asks softly.

I nod without having the ability to say anything.

She jokingly told me to use my words.

"I'm fine, Goddess," was my response.

"Good dog," she happily said, stroking my face. "Now go wash up and I'll get some food."

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