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Hello people!! Some of you may know me as Vladimir, Sir Vladimir to be precise!
I am asking for urethra (pee hole) dares for my slavegirl!
I usually do not do that (is enough for me ideas in my perverted imagination), but it is a special case. She wants urethra game, and I'm not very experienced in this. So I ask community for help. I will be grateful for any dare tasks, tricks, teases etc. related to the urethra play. She is quite masochistic pain slut, so feel free to make it reasonably painful! Also, any tips on safety, disinfection, etc. Just please do not try to dissuade me not to do it. I know how difficult it is practice. We're both adults and are aware of our actions.
I'll going to give you feedback if we will use your idea, but it may take a few days.
Thank you for your time! I look forward to your replies!

Never seen any games or dares in that regard that I can think of.

As far as pain goes, just keep in mind that the urethra, bladder neck and the bladder itself are all quite delicate body parts, prone to permanent damage if you are too violent. Always disinfect, using sex toy cleaners or other suitable disinfecting agents. Keep in mind that it will go into a person and be partially absorbed into the body though, so things like acetone or technical alcohol might not be such a great idea.

Other than that it's all good and fun. Even though the goal is BDSM here, you really should start off easy if you're both inexperienced - just like in all other aspects of BDSM and pain play to be honest.

One of the safer ways of making urethral insertions more challenging/painful in a relatively safe manner is vibrations and/or electricity.

As i said i know that female urethra play is quite hard and rough practice, but i belive that it is safe if done correctly. And we both is very interesting in it. That is why i ask for useful advices. Thank you for idea though, i'll try to use it. We have a couple of vibrators that can not get into her urethra of course. We have also Shocking nipple clamps, but I'm hardly to hit her with shock out there, in such a sensitive place. It's only pain, which she is really afraid. Thanks for the idea though, I will try to try it out! Any more suggestions?

You don't need a vibrator that fits inside her. Use a urethral sound and hold the vibrator against it externally. Make sure the vibrator touches only the sound and not her.

The same goes for electro - use a sound and connect an electrode to it. A sensible opposing pole would be her clit.