Share a story about the funnest/hottest bondage predicament or position you've been in

I just hung someone from my ceiling by their undies recently to give them an "atomic wedgie" while I spanked, bullied, teased, and denied them.

I haven't experienced this one but saw it on the internet and thought it was hot.

The male was standing on one leg with arms secured from above.
The other foot was brought up and his ankle was attached by a short tether to a ball parachute.
He was not allowed to rest the upraised foot on the supporting leg for a specified time or he would be put back into chastity.
The domme harassed him and added weights to the foot throughout his ordeal.

There's all sorts of things I'd love to do but most of my clients are no longer in the physical condition to be able to do them.

So, at this point, anything I can actually get my clients into. lol

Sadly true. Most of my favourite bondage positions are now 30+ years and 20+ lbs in the past.

Two answers really.....

1. I've always found spreadeagled on a bondage bed (steel frame and plenty of attachment points) among the most practical. Completely inescapable, it leaves you completely helpless and exposed for edging, CBT, NT, and impact play on inner thighs. It is also comfortable enough for extended play where you might be left for periods of isolation and/or sensory deprivation. It's a position that doesn't create any unintentional "bad" pain to distract from the sensations the Domme wishes to impose.

2. The most effective predicament I have been in was standing (well, crouching really ) while wearing a humbler. My wrist cuffs were clipped together behind my back and attached to an overhead line. That line ran through some pulley's to a wall mounted winch.
She tensioned the line to stress the shoulders in a strappedo position. If you tried to straighten up to ease the pain in your shoulders you added tension on your balls. Crouching more to ease your balls only made your arms hurt more.

Simple but diabolical. She gave me a way to get out early but that involved 1 hard stroke with the cane for every minute of my "sentence" I failed to complete.

This was close to 30 years ago but it still stands out in my mind for it's effectiveness and it's intensity.

I mostly do very long sessions (days) and I like very light bondage, just enough that I lose control. Over time, every bondage becomes a predicament.
And also with light bondage, the predicament can be pushed further:
Imagine your wrists are cuffed behind you and and you have to hold her sneaker to the wall with your nose that is buried in it.
What I find fascinating about it is the simplicity, she can just "park" you to any wall, completely effortless for her, yet it is very humiliating and believe me, with time it becomes real torture!

Similar to Furfan, spread eagle on a bench is my all time favorite. With not only hands and feet secured, but additional straps securing my upper thighs, making it completely impossible to close my legs. Such an unbelievably helpless feeling, and watching the expression on my Domme’s face once she finishes securing me and steps back to admire her handiwork and that feeling I get as she laughs and I know exactly where her attention is about to go. The best!!

My second place would go to the good old St Andrew’s cross. Something about being secured standing, arms and legs splayed wide open…

Ohhh I love this!!

St. Andrew's Cross... I remember my one time well. I'm not a bondage guy per se, but the European Mistress with her own dungeon insisted we start a role play session with me on it. The Cross was attached to a wall. It was our first session. She was pinching my nipples, whispering vile things she was about to do to me, in a tremendously seductive accent. I got so aroused and twitched enough after a few minutes my right wrist popped the leather binding and the stake in the cross (and the wall) out. I was in shock, and so was she.

The Mistress kept in character, got me off the cross, and spanked me, among other things. When the session ended I apologized, offered to have it repaired and she waved me off, saying, "That was very hot. Next time" pointing to the old-fashioned cast iron radiator, "I'll chain you to that. Hopefully you won't break the heating system." We both had a good laugh.

And I'd love to explore it with you ...
... and more.