What was your most desperate experience while locked

I was lucky enough to find a wonderful key holder! I've done all kinds of chores for her, cleaning house, taking out the garbage washing cars doing laundry!etc! For both new to this Chastity game and we consider it just that! Lately she's taking it more seriously and my record is now 8 days! We don't live together so usually is three to four days before she comes and unlocks me! Her daughter spotted the key around her neck and instantly knew what it was! Now when I visit she's I was checking to see if I'm locked! Now I serve two dominant women one I love and one that just uses me! I know her daughter has a loose tongue so I don't have no idea how many people I'm going to have to serve but I'm ordered to lock up now! And she can't be here she makes me send her a photo proof!

 

I'll pick a fun one instead of a downer one, but I've had both. For awhile my wife and I tried a program where I was to have a release and an orgasm once each month on the last Wednesday. She had the right to cancel them, make them ruined or generally just mess with me. I really liked this habit as it got her to be creative and have some fun.

The last Wednesday rolls around and she gives me the key, tells me to unlock and go wait naked in bed for her. She comes up and undresses and we begin to make-out and have some foreplay. She then climbs up and sits on my face in a reverse cowgirl position and tells me to lick her ass. This is something we've only really done in the last year and I really like when I'm allowed to do this.

She begins teasing me and pulling her ass away, just out of reach and wiggling there. She then offers me a choice. I can have sex with her and have my release, but then I'm never allowed to lick her ass again, or I can lock up for another month. She keeps lowering herself back on to me and pulling away again. I'm sort of stammering, just trying to get to her ass and at the same time allow my raging erection some relief.

She keeps on with the "what's it going to be"? routine. Finally I say I'll lock up for another month. No mercy at this point she says "I don't believe you, how can I be sure"? So I start begging her not to allow me to cum, but to please allow me to keep licking her. She continues with this while now fondling my hard-on. Doing the "are you sure"? routine. I'm just frantic at this point as I want both, but I know one will bring instant relief while the other will keep paying dividends for many years. So I'm just whimpering "Please don't let me cum, please don't let me cum. Please let me lock back up for another month". In the end she gave me what I asked for.

 

There have been a few, but I think the most was a day about 2 years ago, it was summer and a here, and my madam came down stairs mid day wearing a tiger print maxi dress, it wax skin tight and down to her ankles and very thin and stretchy. I watched her walk about in it, it showing off her exquisite outline and it going semi see through when the sun was shining through it, we went indoors just after lunch as it was getting to hot, and madam doesn’t like to much sun exposure, we were sitting watching some tv and madam got up for some reason, I had been hugging her and just running my hands all over her, when she returned, she wanted a massage, she sat between my legs as we watched tv and I have her a bench and shoulder massage for about 45 mins,
After she got up and said she could feel my cage twitching between her shoulders the whole time, I said what do you expect wearing that! She told me to pull my shorts down! So I did! Exposing my caged cock, she then lifted her dress up to her waist and sat on my lap, my caged cock resting between her legs on her, she then pushed down grinding herself against my cage!
I could feel the heat and wetness coming off her!
She asked, how bad do you want it?
Very very very bad! I said! I need it! Please madam! I begged and pleaded, I offered her gifts and money and kept and she kept asking what I would do for it!!! Anything madam! I said! Anything! Anything at all!!! Just tel me what you want!!!!!! I pleaded!
Then she stood up and lowered her dress,
And said I thought you would say that, but your still not getting it!

 

I am still desperate.

Yesterday, I was to leave town for four days. As I was waking up, she came into the bedroom with nothing on but my/her key on her necklace. She begins by dragging it up and down my chest, clinking it over the bars of my cage, up and down my legs. This goes on until I'm ready to faint. She rolls off of me and I proceed to give her two very intense G-Spot O's. She then unlocks her cage and begins stroking and sucking me. She builds me up and lets me down a few times. Then locks her cage back up.

And, locked I be.

 

I'm locked up to control addiction to porn and masturbation. My wife doesn't generally deny me long term, releasing me every week or two so we can put my cock to its intended use.
There ended up being a stretch over a month long that due to her travelling or other reasons I wasn't released. When we finally got naked together, she started pinching my nipples. I've always enjoyed this, but this time it was a whole new sensation. My whole body was tingling, I couldn't focus on touching my wife. Waves of pleasure flowed through me and it was like I was in a trance. I don't know what sounds I made, but my wife said "I think we better unlock you". Our unspoken rule is that I NEVER get released until I've either made her come or she's so close that finishing won't be a problem. We both know that before I was locked up I was pretty selfish and she didn't get her share of orgasms.
This without a doubt the most desperate I've ever been and my wife obviously knew it. Sex after being locked is the best we've ever had.

 

Hmm, obviously, I've felt "desperate" when I've been locked for a long time and teased by her and really, really just want to finally be released and cum. And I've felt like that a number of times watching and listening to her get off on her huge dildo while I am denied and my penis is as hard as it can get in its cage and aching to cum...

But I guess if I had to pick the one moment I recall being the most desperate, it would almost certainly be one particular time that she left the key for me to find. She does this sometimes when I've been locked for a long time and she is ready to release me, but she makes a bit of a game of it by leaving the key somewhere that I might find it after she goes to work. If I find it I will call or text her and thank her, of course, and then free myself and enjoy some masturbation, perhaps even with a suggestion or two from her (e.g., to watch cuckold porn, to ruin my orgasm, etc.). If it's later in the day and I haven't found it or haven't even looked for it because I never know when she might do this, she will ask me if I've found my key. And then I frantically run around the house looking for it. She never leaves it in plain site, almost never leaves it in the same place twice, and she has more than once not left it at all even when I've been alerted by her to look for it. That, of course, leads to feelings of desperation. But that's not what happened this one time...

No, I found the key relatively quickly. I had been locked for 5-6 weeks by then, and I was horny as hell, and when I found the key I was extremely happy to have it and couldn't wait to unlock my penis and have some fun. But when I put the key in the lock it wouldn't turn. The lock had been used for a few years without any trouble, but probably due to grime and lack of regular maintenance, this time the lock just wouldn't work. I tried and tried and tried. By now my wife knew I had found the key, and when I told her it wouldn't open the lock she thought it was rather funny for a while. But we both got worried when I was still unable to open it after an hour or more. With the help of some WD40, pressure, countless attempts, and luck I finally got the lock to open. But only just before the kids got home, so my chance to enjoy myself was gone.

With my wife's support we have since replaced that lock, bought some lock oil to do routine maintenance on the new one, and also bought some bolt cutters just in case.