What are the most memorable comments your keyholder has made about your chastity?

Your tiny penis is funny

 

My husband locked me (randomly handed me the cage and accompanied with "put it on") this passed Monday when he was going out for the night (as he does every few months). When he returned he let me know we were starting one of our usual chastity dice games (usually last 5-20 days), consisting of 8 DnD di that I can roll up to 3 times per day. For this game he added mystery envelopes (containing mutually agreed upon advantages and puishments) to play "let's make a deal" throughout the lockup. Last night I drew an envelope that got me tied down and edged. He said I could save the advantage but I thought "no better time than tonight" and he tied me to the bed and uncaged me.

Usually when he edges me and I ask permission to cum (I am required to ask "may I please cum sir"), he draws back for a few minutes and then works me back up. Last night he said I needed to say "please put my cock back in its' cage sir" when I get close. Only this time when I got to the edge abd said his required statement to did not draw back and bring me back to edge, he just responded "ok, we will put you back in the cage" and locked me". Both the request that I ask to be caged and the response of immediate caging were hot.

P.S. After the edging I was required to flip a coin to determine if the edging cost me anything and it indeed cost me another day before resuming the game...

 

I just shared this with my keyholder/partner she found it hilarious it seems both yours and mine share the same sense of humour!

 

Get use to that thing, cause it's never coming off again.

 

I was tied down to the bed, teased by a couple remote control vibrators for most of the afternoon one weekend - like 4-ish hours. My phone was nearby for safety purposes (so I could text, I was gagged). My wife came into the room and asked me if I wanted to be released... She said she was hungry and wanted me to make dinner soon. She pushed my gag down and I asked "how soon?"

She decided another 30 mins or so, then said "Alexa set a timer for 20 minutes" and said she put the key to my wrist cuffs within reach. And told me not to release myself until the alarm went off. She leaves and the vibrators start up again, somehow more intense than before, I'm lost to a world of ecstasy and frustration.

A little bit later my text message goes off and the vibrators pause, I check it:
"Where are you?"
"Alarm hasn't gone off, you told me not to get out until then"
"How much time is left?"
My gag was left off so I ask Alexa...
"There are no timers set".
I tell my wife "Alexa says no timers set!"
and that's when I get the best thing she's ever said -

"Sucks to be you" ... and the vibrators started back up again

 

Sounds like.my wife lol

 

Me (while massaging her feet): I know you love this, why don't you ever just tell me to do it?

Her: I just don't want to impose on your free time. You work so hard, so I just wait for you to want to do it.

Me: so you don't mind walking in with a huge dildo peeking out from between the folds of your robe and telling me to drop trow so you can proceed to plunder my ass with it, but asking me to massage your feet is a bridge to far, huh?


Her: honey, if I could make you squirm and groan like that does by making you do this, this would be your permanent position!


Yes, my cage got extremely tight....

 

You mean MY property?

My dolly is locked up because I don't want anybody playing with her except me.

 

I recently mentioned I was getting horney and my KH said, "You need to relax, you're cage hasn't even been on for a week yet"

 

Tomorrow will be 3 weeks, a record for me, after talking about how great I feel with my Wife this morning, she says “only 2 months and 3 days till our Anniversary, you should be able to handle it”
I also asked about maybe being allowed an erection today, it’s been 6 days since the last one was allowed, and her response, “nah, I don’t think it’s time for that yet, but you can eat my pussy later”

My stomach dropped, no idea if she’s serious or teasing me, and I love that!

 

My Queen loves humiliating me by telling me i'm her useless sissy bitch . She often commands me to open my legs as I kneel for her to whip me. My Queen loves bringing her belt at full force up from the rear ,and between my legs landing on my cock and balls . I know I'm a useless sissy, and fear what comes but when it's over I'm so greatful to my Queen for showing me the piower she has over me.

 

I'm just going [meta] for a moment to mention that there is a long running thread called "Hot things your KH has said to you".

 

The hottest thing my Queen ,who holds the key to my jailbird ever said was when I asked when I'd be allowed an orgasm, she replied I'd never get one for the rest of my life .. That was the sexiest thing I had ever heard..

 

We were texting some dirty memes back and forth. The last time sex we had was a few weeks back and it was me wearing my strapon and harness. Out of the blue she texted “I came so hard when you were fucking me with Johnson (our name for the dildo) and your little cage kept hitting my clit” then “I think I cum harder when I know you can’t even get hard”.

Well that certainly got my juices flowing, I think I ordered 3 more toys and two more harnesses lol

 

Her: "How long has it been since you came?"

Me: "Too long"

Her: "Wrong! Not long enough!"

 

I haven't had an orgasm of any kind in five weeks. Yesterday, basically in the 69 position,. I got to service Miss K orally, while she slapped, squeezed, and pulled my balls the whole time. Last night hoping she would grant me some relief, I told her how much my balls still ached from the days activities. She quickly told me no, and proceeded to tell me. In a few more weeks I won't e even notice the pain.

 

R and I went out to the local bar last night. She had worn a long black silk shirt.
When we got home, I sat on the front porch for a bit to smoke a cigarette. I heard her walking toward the door and her footfall sounded different.
She opened the door and I saw her standing there in just the black shirt and heels.
She sat down in her normal spot as if nothing were out of the norm. I could only stare....
She uncrossed her legs, after a few minutes, and I could see that she wasn't wearing panties.
Every few minutes, a car would pass by on the street, but she simply ignored them.
She finally looked at me and said "if you expect to be unlocked at all during our vacation (in about 3 weeks), you need to make me cum right now".
What else could I do other than get on my knees and feel myself strain against the cage.....

 

@Robins toy I trust you now have something to look forward to on your vacation? That is of course if she asked you for a cigarette afterwards. If not, it could be a long vacation.

 

My K/H told me I'd never have another orgasm for the rest of my life. I was permanently caged. That lasted many many months , until I broke free of her. Now I'm back again, and caged again, and loving it.

 

"I'm never giving you the key back. If We split I'll give it directly to your new Owner!"

"Yes, it's permanent!"

"It's for life"

 

"The device is permanent, therefore there is no endpoint."

 

Last year after I had fitted my iron maiden madam and I were sat on the sofa, I’d been wearing it about 45 mins and madam asked me to show her, so I Slipped my joggers down and she took hold of me, and started teasing me, and she asked how it felt, how the spikes felt, painful! I replied,
To which she answered, good get used to it, it’s what that pathetic thing deserves for disappointing me!

 

If it is a long vacation, I will be even more enamored with her!