Aysie's Challenge
Bdsm Story

Aysie's Challenge

by Rebell1ous 18 min read 4.8 (16,200 views)
femdom chastity bondage loving college leather
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Surprisingly, Kaysie doesn't lock the cage back on me immediately after lunch and instead she cuddles with me on the couch. We watch a couple episodes of her favorite generic cop show before she says anything.

"Baby," she whispers in my ear. "I wanna talk to you about something."

"What's up?"

"I wanna ask you something but please don't panic," she says in a shaky voice.

I nod and kiss her forehead. "What is it?"

"What do you think about me... maybe being a bit more dominant?"

"What are you talking about?"

"I wanna..." her voice trails off. I cup her chin and lift her face to meet my eyes.

"What's up?" I'm a bit concerned but try to sound gentle. "You're scaring me."

"I was wondering if you'd be ok with our friend," she pauses for a moment and looks down "going in his cage for longer than what we've been doing."

"You want the cage to stay on for longer than a week?"

She nervously nods. "If you're not comfortable with it then you can say no," she takes a deep breath. "But I think it could be really fun," her eyes light up a bit "if you don't know when I'm gonna unlock you."

"That's a big change," I say quietly.

"I know honey," she softly says "you don't have to say yes if you're not comfortable, but I think it could be really fun."

Neither of us speak for a few moments as I ponder her proposal.

"How long do you want the cage to stay on?"

"Well I can't tell you that," she chuckles. "That defeats the purpose."

"Fair enough," reply.

"But I remember your limits," she softly says. "It's not staying on for a super long time. And you always have your safe word," she assures me. "You can use it anytime you need and the cage comes off, no questions asked."

"Ok," I say looking into her eyes. "Lets try this," I say.

"You sure?" she asks.

"Yeah, but can you do something for me?"

"Of course," she softly says. "What is it?"

"Would you," I giggle knowing what's on my mind. "This is gonna sound weird."

"Try me," she confidently but sweetly says.

"I've always wanted to see a sexy woman in leather pants," I say sounding more like a question than a statement.

"Sure," she giggles.

I nod and she stands up, extending an arm for me to take.

I take her hand and she leads me to our bedroom. She shuts the door and seamlessly transitions into character. "Get naked," she sweetly says.

"Yes Mistress." My answer elicits a giggle from her.

She runs a finger over my hard cock and smirks at me. "I wonder what that's for," she grips my cock firmly and strokes it. "I think he's excited to go in his cage for his sexy woman," I moan as she leans in and kisses me still stroking my cock.

"Yes Mistress he is," I groan and glide a hand over her back.

"Get on the bed," she says releasing my cock and watching it throb for a moment.

I lie down and she swiftly ties my hands to the headboard and ankles to the footboard, using the cuffs which she has attached to the four posts.

"Sorry baby," she winks "I can't risk you cheating." She reaches over to her nightstand and picks up the cage, leaving it on the bed and walking over to the bathroom.

I hear water running for a minute before she comes back to the bedroom with a rag.

She slides the ring down my cock and presses my balls through it, causing my cock to throb more. She wraps the rag of cold water and ice around my cock for a few minutes before removing it and sliding the cage up the shaft and clicking it into place.

She picks up the padlock, giving it a dramatic kiss. I let out a gentle moan as she clicks the lock in place.

After a passionate kiss, Kaysie unties my wrists and I sit up. Looking down at my cock already straining in its cage. Not knowing when it was going to be set free, I was already feeling a new level of submission.

I look next to my left, and see a smile that could kill me on Kaysie's face.

"How do you feel?" she softly asks.

"This feels so submissive," I whisper.

"Well then it's a good thing you like that feeling," she sweetly says and kisses me.

--

Surprisingly, Kaysie significantly dials back her teasing after that day. She doesn't wear her lingerie outfits around the house. She doesn't make me lick her every day. She doesn't even wear my key on her necklace like she always has. Instead, she clips it to her keychain and leaves it in her pocket most of the time. I think she's trying to make this as easy for me as possible, being that she's never denied me an orgasm for any longer than 8 days.

We spend most of the next two weeks cuddled together watching TV. Despite her restraint with teasing, there is still a significant frustration and desperation building inside me. After all, I'm still a young man who spends every night sleeping mere inches from the hottest girl I've ever seen.

After 10 days of her new challenge, I began to have dreams about her. Dreams unlike anything I had ever experienced before. In these dreams, Kaysie and I would fuck so passionately and she would moan so loud. These dreams were so intense I would usually wake up with my cock desperately straining and leaking.

After a couple of these dreams, I tell her about them. She just smiles and lightly tugs at her necklace.

--

Today, the two week mark since my caging, she has a softball game. As I watch her game, my balls begin to ache more and more as I stare at her. More than usual, I'm aware of how amazing her ass and legs look in her tight pants. It feels like she's just my crush again. Despite my best efforts to focus on the game, I can hardly think about anything except how good it would feel to cum inside her.

In the last few innings of the game, I have to walk to a small patch of trees next to the field and turn my back to the game. I really don't want to, but the game isn't close and I need to give my cock a bit of a break.

A little over an hour later, I hear her giggling as she wraps her arms tightly around me. I didn't even hear her approaching, but I turn around and kiss her deeply.

We get in her car before she says anything.

"So you didn't wanna watch my whole game?" she asks with a hint of playfulness.

"I couldn't. I'm sorry," I softly say.

"Oooh," she says with a knowing grin. "Is our friend really starting to miss me?" she reaches over and runs a hand inside my thigh.

"Yeah," I quietly answer. "It's aching so much."

"Well, maybe I'll help you with that soon."

"Please," I almost inaudibly whisper.

--

We eat an early dinner and she goes to our bedroom as I'm washing the dishes. When I finish the dishes I go into our room and find her standing next to our bed, wearing nothing but her bra and panties. I kiss her so passionately that she falls to her back.

"Baby please," I desperately moan. "Please let me fuck you."

She rolls me over and pins my arms down with a smirk.

"So that's what you want?" she cocks an eyebrow. "You wanna feel my tight warm pussy wrapped around your beautiful hard cock?" she moans.

"Yes yes please."

"No," she flips her hair and stands up.

"Please," I beg with a tear in my eye. "Please please ple-," she puts a finger over my lips.

"No begging," she says lying down on the bed. "But if you insist on using that tongue, I have a better use for it."

"Yes Mistress," I weakly say.

After that night, she returns to her usual intense teasing and it drives me absolutely insane.

On Sunday morning, I woke up tied to our bed and licked her to more orgasms than I could count. She gave me a "blowjob" with the cage still on after she was done with my mouth. Then, she spends the entire day wearing a set of pink lace lingerie so skimpy she'd probably be arrested for wearing it in public.

In class on Monday morning, she begins running her hand inside my thigh during our professor's lecture. My fight to stay quiet is more difficult than almost anything I've ever done. She only turns the difficulty up when she takes the key out of her pocket and runs that inside my thigh. That afternoon, she also starts wearing my key on her necklace again. In a way, I had missed seeing the constant reminder of her control. In every other way, having the constant reminder of her control drove me even crazier.

On Tuesday, she surprisingly doesn't do anything in the morning. But she has her last softball game of the season after school, and those are never easy. Her game was absolute hell for both of us. My chastity cage seems to have shrunk since the morning, and Kaysie's team lost. They got shut out and missed the playoffs because of the loss.

I don't walk away from the field this time,knowing that she would appreciate me staying there for an ugly game like this.

Oddly she doesn't seem the slightest bit upset about the loss as we drive home.

A simple "We would've gotten crushed anyway," is all she says about missing the playoffs.

She goes back to her teasing once we're home. After a few minutes of silently eating ice cream in the kitchen, she "accidentally" drops her spoon. I think I might actually burst through my cage as she bends over in front of me, just a bit further than she needs to.

For the first time, I lose control of myself and spank her. She turns to me with an eyebrow raised but a look of satisfaction on her face.

"Seems you're a bit worked up," she says undoing her top two buttons of her blouse which uncovers the key on her necklace. "Something on your mind?"

"I wanna cum," I desperately plead pulling her into a hug.

"I know I know," she baby talks. "But the thing about your current situation is that it doesn't matter what you want," she moans in my ear.

"Please baby ple," she softly puts a finger over my lips.

"As long as you're securely locked up in this cage," she caresses my cage through my jeans "only I get orgasms." I begin to whimper and inaudibly plead with her. "And you're just my toy," she caresses my cheek. "My handsome, selfless, and skilled sex toy." I continue to inaudibly plead as she continues to sweetly tell me about our relationship. "Sometimes I use your tongue, and sometimes I work you up to see just how crazy I can make you."

"Please," I softly beg as I finally regain the ability to use words.

"But right now," she softly runs a hand down my chest. "I want you to be my handsome slave for the evening," I run my hand through her hair. I nod, hoping that the night ends with her finally unlocking the cage and fucking me.

She takes my arm and leads me to the bathroom where she begins to strip.

"You're going to shower me," she says with a smirk. "And don't you dare try any funny business in there," she says holding up her necklace. I nod and she turns the water on.

Running my hands up and down her body in the shower is one of her more devious teases. When I finally finish washing her, my cock is dripping pre cum and I'm positioned behind her.

I begin to suck her skin right where the neck and shoulder blade meet, a spot I know she loves.

She turns around after a few minutes and kisses me deeply. "Such a good toy," she says running a hand up my back. "Almost like you want something," she winks. "Can't imagine what that could be," she gently caresses my swollen balls.

--

I wake up Wednesday morning, after another intense dream, with my cock already struggling in its cage as I've grown accustomed to. Kaysie must've already been up, as I had a coffee on my nightstand. I walk into our kitchen, and she's making eggs for breakfast.

Throughout the day, she gives me a bit of a break from her teasing but there's an undeniable ache continuing to build.

Prior to our last class, she tells me with a wink she has a surprise for me after. I think and hope for a release, but she brings me to a movie theater instead.

We see a new sci fi movie, but I pay no attention to it from the 10 minute mark on. She puts my left wrist in a cuff with a small chain on the end of it. Then she clips the chain to the belt loop closest to her sex and runs my hand between her thighs.

After the movie finally ends, she undoes the cuff and slides it in her pocket. When we finally get home she cooks us dinner. When we finish eating, she puts her feet up on my lap and puts her show on the TV. I don't dare move them, and she leaves them there for a while before she goes to shower.

After her shower, I take my own. The feeling of frustration is overwhelming as I look at another day of denial. When I get out of the shower, I see that she took my clothes out of the bathroom. I walk to our bedroom, hearing the padlock bouncing off the cage.

When I walk into the doorway, she's standing next to our bed with her hands on her hips. She's wearing a pink lace top and crotchless black leather pants.

I almost instantly begin to whimper, as she approaches me with a smirk. She wraps her arms around me and kisses me as I run my hands up and down her leather clad legs.

When we break apart, we rest our foreheads against each other for a moment before she speaks. "On your knees."

She puts a pillow on the ground for me to kneel on as I lick her. I run my hands up and down her ass as I lick her and growl as she teases my caged member with her foot. When she pulls my head away, after her orgasm, my cock is dripping pre cum onto the pillow.

She reaches down and taps a finger against my cage. Then she grips under my shoulders and lifts me up. She scratches my back and chest with her beautiful red manicured nails, kissing me deeply. As we kiss, I grip her hair with one hand and with the other, I squeeze her ass so tightly that it might bruise.

When she break apart, she flips her hair to one side before cheerily speaking. "You're gonna cum tonight baby," she says moving one hand to grip my bicep with and putting her other hand on my chest.

"Really?" I excitedly ask. She nods and tightens her grip on my bicep. "You better not be fucking with me," my voice cracks as I feel her rub her exposed pussy over my cage.

"Odd," she laughs "usually you like when I do that." She guides me to our bed. "I'm not teasing you baby, I promise." She turns me around and cuffs my wrists behind my back. Then she turns me around again and kisses me. "You've earned this. This is by far the longest I've ever denied you."

"Thank you baby," I groan as we kiss.

"So," she asks sweetly caressing my balls. "How do you wanna cum?"

"I want you to suck me off," I say with a gulp as she caresses my cheek. "I've never cum from a blowjob."

"You got it baby," she says taking off her necklace.

She slowly slides the key into the padlock and turns the key. She slides the padlock out and my cock instantly grows, pushing apart the ring and cage. My knees buckle at the feeling of air on my cock for the first time in two and a half weeks. She catches me as my knees buckle and gently guides me back to a vertical position.

"It's ok I've gotcha," she softly says as I moan feeling my cock throb. "You ok?" she asks after allowing me to collect myself.

I nod and she shoves me on the bed and quickly ties my ankles to the corners. She climbs on the bed next to me and gives me a sweet kiss while scratching the inside of my thigh.

"Baby, I know you're probably super sensitive. I don't expect you to last, just cum whenever you want to," she says encouragingly. I nod and she climbs down the bed, licking her lips as her mouth is just inches away from my aching cock.

She gently kisses and licks my tip before parting her lips and sliding all the way down my cock. My voice breaks as I moan when she starts to suck me.

After only a few seconds, she begins to bob her head up and down. But when I start to thrust my hips into her mouth, she stops bobbing her head and lets me set the pace with my thrusts.

"Oh fuck!" I cry out as she runs her tongue over my frenulum. "I... I'm... I'm go... gonna...!" My voice breaks and my vision goes white as the most powerful orgasm of my life takes over my sensations.

When I return to reality, Kaysie is on her knees between my legs with a smile on her face. When we make eye contact, she loudly swallows my load of cum and winks.

"Was that fun?" she asks blowing me a kiss. I nod, still short of breath.

"You're still SO hard," she points out lightly stroking my cock. "Do you wanna fuck me now?" she smirks already lining her pussy up with my cock.

"Oh yes," I answer. "Please."

"I thought you'd say that," she lowers herself down onto me. "But you have to make me cum now," she says between moans.

She slowly, agonizingly rides me for her own pleasure as we just stare into each other's eyes. After a few minutes, she lowers her upper body and kisses me.

"Fuck me until I cum," she softly says wrapping her hands around my throat.

I thrust up into her, hearing her moans rise but I don't think I can last to make her cum.

"Baby," the noise I make is somewhere between a plea and a growl.

"Oh I know baby," she replies putting a hand over my mouth. "I know... it...it feels so... so good. But... I wanna... c... cum on your... cock."

"I... I c... can't."

"Y... yes you can... ju," she stops speaking and muffles a moan. "J... just a... little... longer." She stops speaking and lets out a moan I can only describe as animalistic.

Her moan gives me a little extra motivation and I give two more hard thrusts before I feel her convulse around me. Her moans send me over the edge and I cum deep inside her.

The next few minutes are an orgasmic haze for both of us. When I return to reality, she's just lying on top of my limp body.

She seems to regain some of her strength before I do and lazily lifts her head.

"Baby? You ok?"

I don't have the energy to speak yet, but I give a hum of acknowledgement and nod.

She seems to regain energy as she rolls down my body to release my ankles. I don't even feel the cuffs come off, but I see her toss the empty manacles off the bed.

She rolls my limp body over and releases my wrists, caressing the marks from my struggling.

"Wow this looks yummy," I hear her softly say to herself. I have no earthly idea what she's talking about.

"Wha-" I moan as I I feel her lips wrap around my tip and she begins to suck me clean of our juices.

I return to reality feeling her suck me again, clearly wanting to completely drain my balls.

I look down at her and see her eyes, twinkling as I sink my hand into her hair.

I take her hand in mine as I press her head down until I feel her gag on me. When she gags, I begin to take my hand out of her hair. But she grabs my wrist with her free hand, and pulls it back down onto her head.

I grip her head and continue to press her head down, feeling her choke on me but she doesn't release my wrist.

I cum again, this time straight down her throat.

She takes a deep breath as she lifts her head up and collapses on the bed next to me.

We snuggle up together, not saying anything as we collect ourselves.

"You ok?" she asks after a few minutes of silence.

"Yeah. You?"

"I'm ok," she kisses my forehead.

It's probably another five minutes before either of us speak again.

"Baby?" I ask lifting my head off her arm.

"Yeah?"

"Are you going to lock me up for even longer now," I ask knowing how she loves to test my limits.

"No," she chuckles. "I'm not going that long without cock again for a while."

I chuckle and my head collapses back onto her arm.

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