Kaysie's Repayment Ch. 02

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Mike's biggest fantasy.
1.8k words
4.66
17.4k
17

Part 2 of the 5 part series

Updated 06/12/2023
Created 10/26/2022
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Kaysie and I are sitting next to each other on her couch watching a movie. To my surprise she had been sitting with me and talking to me pretty much any chance she had. I had grown to see her not as a kink dispenser but as a friend and... maybe something more. I couldn't tell her though. What if she doe-

My thoughts are interrupted by her scratching my thigh. "We still on for tomorrow night?"

"As far as I know we are."

"I wanna do something a little extra special for you," she kisses my cheek.

"What did you have in mind?"

She gets off the couch and goes into her room. She comes back into the room a minute later with her hands behind her back. "I wanna fulfill a fantasy for you."

"You do that just by tying me up and teasing me."

"I know but this is a little more," she pauses as if to ponder her next choice of words "extreme and intimate. And also, I know this is your biggest fantasy." She shows what she's been holding and she doesn't need to say what it is. A chastity cage.

I've never seen one in person but I know exactly what it is. A three inch long steel prison for my cock.

I stare at the cage without speaking for a moment.

"I think that's a yes from you," she giggles running her hand over my bulge. I don't answer until she cups my chin "Well?"

"Yes. I want to play."

"Drop your shorts," I slide my gym shorts and my underwear down, exposing my rock hard cock. "Lock yourself," she hands me the cage and kneels in front of me.

I stare at my cock and hope that it goes down soon. "What are you waiting for?"

"I can't stay soft with you breathing on my cock like that."

"Oh? Did you have something on your mind to help with that?" she kisses the tip of my cock.

"Please suck me off."

"Not yet," she rises and runs her hand over my chest. "I want you to lock yourself up. I'll let you out tomorrow night when we play. But I want you to be nice and needy for me," she hands me an ice pack previously concealed in her cooler.

"Yes Mistress," I ice myself and quickly slide the ring and cage on.

She hands me a padlock "Finish it." Without hesitating I snap the lock shut. "What a good boy." She pulls a key out of her pocket causing my cock to stiffen and strain in the cage. "Completely under my control."

I struggle to keep eye contact until she pinches my nipple. "Kneel." I oblige and look up at her. "Service me."

--

I lost count of the number of orgasms I licked her to that night. I woke up next to her the following morning. I go to her kitchen and make us coffees. When I return to the room she's just woken up. "Morning Kays," I hand her a coffee.

"Mornin," she ships her drink. "Are you coming to my softball game this afternoon?"

"Yes."

"What a good boy," she teases holding up my key. I blush and look away. Until this moment I had actually forgotten about my bondage.

"How does the cage feel?"

"Frustrating. Especially when you're holding the key a few inches from my face."

"Sorry not sorry," she kisses the key. I've got some errands to run. I'll see you at the game."

--

The day seemed to last about six months before her game at two in the afternoon. I show up about twenty minutes before it starts and stand down the third base foul line, away from people. Just before the game starts. Kaysie comes over to me "Good luck kiss?" she enquires. I chuckle and give her what she wants and she shows off her new bracelet. There's a key hanging on it.

"Is that what I think it is?"

"Depends. What do you think it is," she winks and goes back to her dugout.

I'd be lying if I said I was focused on the game at any point that afternoon. I couldn't stop staring at Kaysie. In less than a week she had gone to a longtime crush that didn't know my name, to a friend with benefits to someone that I had deep feelings for.

When the game finally ended I waited for her outside the dugout. "Hey stranger," she approaches me and gives me a kiss.

"Ready to go?"

"Yeah. I've got some surprises for you." My cock strains in its cage.

--

She drove us to her place, scratching my thighs every few minutes just to tease me. Despite her teasing, neither of us talk for the first half of the drive. "I bet you wanna get hard right now," she laughs. I don't answer, trying to take my mind off the ache in my cock. "Do you remember that wonderful blowjob I gave you last weekend?"

"Yes."

"I bet you want me to do that again." I nod. We pull into her driveway and she puts a hand over my cage. "Be a good boy and maybe I will."

When we enter her house she wastes no time pushing me against the wall and kissing me. "Oh you are so gonna get it tonight," she smirks.

I don't answer. Unsure if she's saying that to tease or if she's actually upset with me.

She extends her hand out to me. For the first time I notice her new pink painted nails. I take her hand and she giggles "Is that a weird fetish of yours?"

She leads me to her kitchen and makes herself a protein shake and gives me a glass of water. I drink my water before she starts her shake. Once I finish my water she opens her silverware drawer and reveals a pair of handcuffs.

"Strip." Once I'm naked she turns me around and cuffs me. "Kneel." Once I'm kneeling she leans against her counter and looks down at me, sipping her shake but not saying anything. My cock strains in its prison looking at her gorgeous body.

Finally she finishes her drink and stands up. She walks over to me and brushes her fingers over my face. "Are you excited?" she teases.

"Yes Mistress."

She crouches down and examines my cage. Lifting it up and running her fingers over it. "It gets me so wet knowing that this dick is completely under my control," she holds up her bracelet "locked up so nice and tight. Desperately trying to get hard."

She stands up and extends her hand to me again and leads me to her bedroom this time. She undoes one of the cuffs and stares at me. "Lie down," I happily oblige and she redoes it over the headboard. "Before we get started, I'm going to go change into my sexiest lingerie. Then, you belong to me."

She returns wearing a navy blue lingerie set. "I bought this just for you," she poses. "Do you like it?"

"Yes Mistress."

"I know you do slave," she climbs on top of me and kisses me. "Would you like to be released from your cage?"

"Yes please please Mistress."

"Maybe," she smirks. "But you have to prove you deserve it first," she runs a finger over my face and neck. "Maybe with that talented tongue of yours," she smirks down at me.

After she cums twice she lies down on me and scratches my chest. "That was nice stud," she laughs. "As promised," she sits up and unlocks my cage. My cock surges to life fully erect and throbbing.

"Now, about that blowjob," she runs her fingers over my cock.

"Please please please."

She starts by teasing me with her finger and kisses my cock. After a few minutes of me begging, she wraps her lips around me and I gasp. Just like her blowjob from last week, she expertly edges me for what feels like hours.

When she stops I groan and she smiles at me. "That was fun," she pinches the head of my cock "for me."

I groan as she goes to her dresser and comes back with her hands behind her back. "I think that you're going to enjoy this." She gently pushes a ball gag into my mouth and slides a blindfold over my eyes.

I feel her slide something down to the base of my cock. "Can't have you going soft, can we," she teases running her hand over my chest. After a few minutes something bites into my nipples.

Once the clamps are on she goes back to her edging blowjob. I began counting the amount of edges to prevent myself from going insane. I counted up to eight before she stops.

She tugs on my clamps and pulls out my ballgag. "Please please pl-" she shuts me up by kissing me.

"Do you wanna cum?"

"Please. My cock is so hard it hurts right now."

"But I like it that way," she laughs. I whimper as she presses the gag back into my lips. I feel dread as her lips wrap around my head again. I go back to counting in my head and hoping for mercy as she goes back to sucking me.

1.

2.

3.

4.

5.

She stops and removes my gag and immediately lowers herself onto my face. I lick her desperately and stop myself from begging without permission. After she cums she climbs off of me and removes the blindfold.

"You ok?" she cups my chin. I nod, unable to put together a coherent thought.

"I want you to fuck me," I finally gather enough of myself to say, making her chuckle.

"I know you do. Good thing I wanna fuck you," she presses the gag back into my mouth. "Don't cum until I say you can."

She laboriously rides me, making sure to not let me cum as I wail beneath her. After she finally cums she kisses my forehead. "Such a good boy for me," she laughs squeezing my throat."

She goes back to riding me and continues to choke me, only releasing my throat every minute or so to allow me to catch my breath. "Cum baby cum." I explode as she finally says what I've been waiting for all week.

She quickly gets up, undoing the gag and the cuffs. I sit up and give her a deep, passionate kiss. "That was amazing."

--

After about half an hour of lying in her bed together she reaches over to me. "So are you not going to bring it up?"

"What do you mean?"

"Us. We're obviously both attracted to each other. We clearly love spending time together," she was about to say what I'd been struggling with for a week. "I wanna officially start dating."

I kiss her. "I thought you'd never ask."

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5 Comments
maddictmaddict3 months ago

So far this story is Cummings along nicely /'

AnonymousAnonymousover 1 year ago

Agree that more detail needed in the sexual act. Doesn't need to be over the top but that shows the physical culmination of their activities and could describe at least the emotions/feelings more. Great story still!!

AnonymousAnonymousover 1 year ago

3 stars only. The idea is great, the grammar fine but the writing is a little like a shopping list; it lacks emotion. I am really sorry, because I so wanted to love it. A passionate girl who doesn’t go OTT with whips, chains and beatings. She appears to just want to tease and play rather than be incredibly cruel. She certainly does not hate men, like so many women today. Be interesting to see if/how this develops.

UKCuddlyGuyUKCuddlyGuyover 1 year ago

I gave you a 5 for the last one, and this time you introduce a personal fetish of mine (long nails in red, pink or purple) - wish I could give you higher than 5 for this one. Looking forward to the next one and giving you a follow to make sure I don't miss it!

AnonymousAnonymousover 1 year ago

great so far, we wish you would expand on the sex scenes more, instead of skimming over them. such as the frustration and excitement denial they are both feeling before release of their orgasms. please keep write on this story..

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