Karen Chapter 22: Pillow talk

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This entry is part 22 of 18 in the series Karen

I woke up fully refreshed. It appears my body finally got used to sleeping with the cage on. Karen was still asleep, nude, as she’s been sleeping since our anniversary last week.

I looked at her, so peaceful, angel-like. I loved her so much, she is so beautiful and sexy and yet, she torments me so much! Last night, she had had sex with so many people while I couldn’t even have access to my dick. It was pure torture so why did I love it so much?

Was this metal thing warping my mind and turning me into my own worst enemy?

I touched the tube under the pajama and under not one, but two pairs of underwear that Karen made me wear and traced with my fingers the metal work. Such a simple piece, such an elegant work, such a torturous device.

Karen turned around and I withdrew my hand. I could see she was slowly waking up from her slumber, not quite yet awake but no longer fully asleep.

I smiled. I couldn’t help but smile whenever I saw her. I fell in love over 5 years ago and despite the recent development and learning, she had planned to chastise me from pretty much day one, I still loved her.

“Oh, good morning chasty!”, she said, realizing I was awake despite not having opened her eyes yet.

“Good morning mistress”, I replied, thinking this is what she wanted.

She gently opened her eyes and placed her hand on my chin.

“Are you feeling frustrated enough? Are you about to burst out of that metal cage?”

I wasn’t sure what to answer, but visibly, she caught that.

“Ah, so you ARE up for more! Me sleeping with most of the men last night wasn’t your breaking point. Interesting. I say we call that nice couple from last night and invite them over. I’d go see them, but I don’t plan to get dressed until tomorrow morning so I can’t quite get out, can I?”

She was quite devilish. I wasn’t sure how much I really liked it, but I seemed to be willing to go along with it.

“Can we talk seriously?”, I asked.

She sat on the bed. “Sure. It’s important we communicate. I mean, this is a game and I know I am having fun but we need to make sure you have some fun too”

Good, she was willing to talk.

“You say it’s a game. Can I know the rules? I mean, unless the only rule is you decide everything”

“Well, not everything”, she replied. “But yeah, basically the rule is, I get to try to have as many orgasms as possible, from as many sources and people as possible, while tagging you along as long as possible as a willing participant of the game and while denying you any orgasms for as long a possible. It’s that simple. We win if we get to have fun while I have orgasms and you don’t, and we both lose if either of us stops having fun because then, well, there is no more us to speak of and I need to try again with someone else”

“So you are really all in?”

“All in. And I really hope you are too because I do love you very much and I really hope we can win this game. I really don’t want to lose you”

“Yeah, so last night, we’ll be doing that again?”

“Hell year, most Saturday evenings, and perhaps Fridays too. You don’t have to come each time, however, but I’ll be going.”

“Well, I still had fun watching you, so I’d rather come with you”, I replied.

“It will get worse you know, I mean, for you. I will raise the bar as time goes by, you do realize that, right? Otherwise, it would stop being fun”

“Like what?”, I asked, worried.

“No spoilers..”, she teased.

“So, am I ever getting out of this thing?”

“Oh yes!”, she said.

I was very relieved.

“So, I have a calendar planned of guaranteed dates of unlocking. I am not saying it’s the only days, I might feel generous and give you more, but don’t count on them. Want to know which dates I have in mind?”

Oh boy! Finally, some answers!


“Ok, so you missed two this year already. One is Christmas Eve. As a Christmas gift, I guarantee that I will unlock you and that you will get an orgasm. I can’t promise anything more, however. Don’t get your hopes too high about Christmas.”

“I see”. She’d probably just let me masturbate or something.

“Next up is St-Valentine’s day. On that day, you give me a gift! I unlock you and you can make sweet passionate love to my pussy. Yes, I promise you that! On February 14th, your dick will get to fuck my cunt. That’s something to look up to! I don’t promise an actual orgasm for you thought. Don’t get your hopes too high”

I didn’t know what to make of that, but that’s something!

“Then, it’s our anniversary. That was last week and without knowing it, it was in a way your first unlock. It will now be the anniversary of your chastity, so double anniversary! You will get unlocked and will get to sodomize me, and guess what, you’ll get to come! That’s the best day of the year of you. Anal sex with me, without the cage, and a guaranteed orgasm in me. No tricks, no caveats, no funny business. I’ll even suck it before you stick it into me for a two in one. Oh, but the moment you come, it’s over and back in the cage…”

Perhaps that was fine.

“Next up, your birthday! Don’t think I won’t give you anything… In Summary, on June 22nd, you get the same promise as for Christmas. It’s that simple”

Ok. so not too bad. So far, a maximum of about 2 months between each unlocks.

“And then?”, I asked.

“Oh, my dear sweet husband. That WAS the list.”

“What? But from June 22nd to Christmas, that’s 7 months without any guaranteed dates?”

“Oh, I forgot to saw one tiny details. Between your Birthday and Christmas, I guaranteed that I will NOT unlock you.”

“Wait, so that means that unless you unlock me before my birthday”

“I probably won’t, this is still too new for this”

“As I said, unless you unlock me before my birthday, I will only get 1 orgasm before Christmas?”

“Looks like you can count!”

“But we are in April!!!”

“But it’s almost May, isn’t it?”

“That’s not my point!”

“Oh, is little chasty frustrated at his mistress for taking away his favorite toy for too long?”

“I thought we were having an honest equal discussion”, I replied, seriously.

“We were. We did. I am done with it. Go make me a nice breakfast and clean up the apartment a little: we might have guests coming in later today. Mistress has some masturbating to do, alone, naked in our bed.”

Argh! She will drive me insane!

I went to the kitchen and began realizing that perhaps, just maybe, this was indeed a fun game. What was happening to me???

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