Oops

2 of 4 of the incomparable Charlie S.

This book on relationships says that many men inwardly want women to be in charge and take full control, but they struggle with expressing this desire. What about you boy? Is this something you inwardly crave? If so then you’ve been a very happy boy since I put you in chastity haven’t you? I’ll be nice and extend your lockup time and become more demanding. Oh, it twitched! You’re definitely one of those boys! *smug laugh*

St. Chastity Boarding School 101

Honestly it applies when any man starts talking about politics. Shush. There are better uses for that mouth :/

2023-06-20 We had a serious conversation. She is happy… to have me, kept caged… for a year.

"You're a good boy." she told me.

I swelled in my cage. I blushed. I squirmed.

She grabbed my wrist and held it by her cheek.

I begged her to tell me what it means to be a good boy

"You're wriggly, and fun to bite"

She bit my throat and marked me.

"You're delicious."

I swooned.

I asked her if I can stay this way. she said yes.

She enjoys having her wriggly rabbit back. She’s glad I came back to her.

I got really excited by those words. I feel I came back to her when I restarted chastity.

After toying with me for a while she had a new question for me:

“What does being a good boy mean to you?“

I was stunned. I stammered. She kept coaxing me to speak. I didn’t want to say too much.

I couldn't say out loud "kept caged and frustrated"

I told her “I’m letting go”

She read my mind: “Are you floating?”

”Yes.”

“Is it warm?“

Oh god.. “yes”

She asked me to explain more what it means to be a good boy.

I told her that I'm creamy.

"Sometimes", she corrected.

"Well. I'm brimful. Your little cream pot"

She loved that metaphor. She cooed. I continued

"I missed the cage.“

She purred

I got sober and direct. I don’t remember when I sat up and broke out of my wide eyed bliss.

“It helps me be present. I am grateful. I am glad you enjoy me." I was earnest and honest in this.

Then I told her about the morning I felt she didn’t want me In chastity.

"I thought you were upset because I was caged …."

"No." she interjected

"…and you wanted to touch me."

"No." she stated again.

I was struck at how matter of fact she was. But I continued to explain the exact situation so she remembered.

"I asked you to lick your finger and touch my frenum"

She did remember "No. I didn't want to because it makes you tacky when I do that.”

Silently I was struck how I misinterpreted her completely.

"But wasn't I wet?" I thought I was. I felt wet.

"No. Your crown gets wet. Your frenum was dry."

"Oh. I didn't know....“ I had not realized or understood her in that moment at all. I was apparently getting pushy, and telling her how to tease me.

So I changed the subject while we were soberly talking through miscommunications. I switched to a conversation in mid-February

“You once said you'd never interfere with my chastity. I didn't know if that was a promise or a statement."

"It was a statement." she interrupted.

"You don’t need to say ‘never’. I don't want promises or rules."

"Ok. I understand."

"I need encouragement. I don't want enforcement. I don't want negative emotions, or you to feel like you can't trust me."

She understood. She agreed it’s better this way.

"I want you to enjoy me. I react well to praise."

"Really?!" she laughed at how obvious that was.

"Well I know what I need better now."

"That's good"

I pointed to her drawers.

"There's a key in the drawer if you ever want to use it. I'm not asking you to hold the key.” ”You can break in case of a… whim. I'm not challenging you to want to use it. I just don't want you to feel like you don't have control.“

She nodded.

“I know there’ve been times you've wanted to give me a big orgasm for emotional reasons. I don't want to take anything away from you. I don't want barriers between us."

"I understand."

"So I want to stay caged. Is that ok?"

"Of course." she said. She sounded quizzical: "You've been locked for a year before"

OMFG It's like she reads my mind

I’ve never told her this is my current goal. I swallowed the immediate urge to correct her. But I didn’t. The truth is I was only caged 12 out of 13 months 2020 June - 2021 July, with a break in September. And she did let me out for teasing and edging. In fact my journal shows she gave me 14 orgasms while kept in enforced chastity over 99% of the time, except for that September.

I did not tell her my current goal of staying caged and denied orgasm for a full year. I never mentioned it. Not once.

She's not seeing the difference.

I told her "You have limits too."

She assured me she's fine. She did not feel I was taking anything away from her, or pushing her. This wasn’t me angling for something more or less.

I had misinterpreted her frustration with me when I asked her to make my magic spot wet. I brought it up again to confirm. She had seemed upset when I asked her to lick her finger and touch the bit of pink skin that bulges through the cage rods behind my PA piercing.

"I could have used coconut oil." she reflected.

"So you weren't wanting me uncaged."

"No"

(God I love coconut oil)

She didn't say it but it was obvious now she was only annoyed I tried to tell her how to tease me, and show her what to do. I was taking control, and she pushed back.

Her words "I don't want to." without explanation was due to me getting pushy.

She couldn't be more matter of fact. She isn't making a vow or promise, or feeling like she's giving up something. Not at all.

She will never interfere with my chastity. She will never want me unlocked. I could stay caged indefinitely and be happy... thrilled even. It's just a statement.

She’s very pleased to have me wriggling in her arms, and easy to tease.

I told her to keep encouraging me and praising me. This works.

I explained that my health and sleep issues caused me to decide to take off the cage last year. I didn’t want any impediment to getting a good night’s sleep. I masturbated and had orgasms alone to help me fall asleep.

“That’s valid“ she agreed.

So me being caged is a sign that I’m feeling better. (Back to normal)

She is very happy to have me. Have me back. Have me kept frustrated. Have me kept caged.

She said it. It’s simply a fact. She will not interfere and remove my cage. She knows herself. She’s letting me know. It’s just a statement. It’s ok.

I never need to cum. I never need out of my cage.

She never needs me to cum. She never needs me out of my cage.

After our conversation I kept bubbling over.

I followed her from the bed as she left to shower and start her day. I was puppy dogging her.

I told her that I do need more than sweet cuddling.

I told her bluntly “I want to get fucked”.

I waxed on how I wanted her to take me, penetrate me, finger me. Or just make me feel fuckable. Playing with my ass, spanking and squeezing makes me feel sexy. I do need sex. But I can stay caged.

I started to say that last time (in 2021 when I broke) that I just needed to be fucked. As I spoke she reached to grab and squeeze my ass. Then when her hand slid down, silently promising more, I lost the ability to form sentences.

I moaned. She made me feel fuckable. She smirked. She's happy with me. She doesn’t need me unlocked to push my deep buttons.

She knows.

She said “You‘ve been caged for a year before.“

And while I never told her this is my plan… to finally float for 12 months in caged denial.

She knows.

—

Afterword:

I did not mean to have this serious conversation this morning. It just happened to be on the 114th day since she last fondled my uncaged cockhead. My glans hasn’t been touched since.

Her edges were slow gentle and careful. She got me pouring over, without force, without a single twitch, without a hint of climax, until I begged her to stop. Then she gave me one more before I scrambled back into my cage, desperate to stay floating on the high of denial. Today just happens to be 114 days since I was unlocked and given a ruined orgasm.

Why is 114 days important? That’s my prior record for orgasm denial. I had only been in enforced chastity and denied orgasm for 114 straight days as of 2021 April 25th. On New Year’s Day, 2021 January 1st, she had asked if I could cope if this next orgasm she was about to give was… well she said “Could you cope if this was your last one?…“

I had apparently gulped this down, it was hard to swallow, and she saw my face fall.

“…this year”, she added, softening the sentence. She had praised me for being easy to mindfuck.

Today wasn’t just a mindfuck. It was a statement of fact. She will never want me unlocked. She will never interfere with my chastity. She is fine with “a year” of caged denial, even though I didn‘t tell her about my goal. She’s happy.

So.. Today… Today is exactly 19 weeks since my last full orgasm. Today is over 16 weeks since my last spill while out of my cage. I’m floating adrift in unchartered waters.

She said it. She meant it. This was not a promise or a threat. This was a simple fact and self accepting knowledge.

She said I can stay caged. I can be kept denied.

She said I can be kept ”for a year” (like) “before”.

She said it. Plainly. Then she said it again with a genuine warm smile. She enjoys me.

She’s grateful.

Boys will see a girl with biceps and back muscles and be like… hii daddy *twirls hair*

PSA: if he cums on you while he’s riding you it’s his job to clean it up.

mommy said you could cum, not make a mess, so be a good boy and lick it up for me, taste how desperate you were to cum just from mommy’s cock.