I don’t think you need to be trans to do this, it’s valid for anyone who’s really into ruins, (let’s make ‘Ruin Slut’ a thing right now!).
As I’ve said before, just be a bit cautious with ruins. We know edging is already fucking with your state of mind, it’s building up all the feel good hormones, but never releasing them in a rush of orgasm, which is why you get the whole ‘denial high’ thing happening. But when you ruin you’re taking that even further, starting to flush through the hormones that give you the high but not masturbating enough to get the full pleasure and so finish the process it can leave you in a very fragile state, crying is common if you ruin hard. Telling a sub to do multiple ruins one after the other is one of the meanest things I do with denial.
So yes, just keep an eye on your mental health as you try this as you’re really pushing the boundaries of denial and it can make you feel like shit, which isn’t fun for anyone.
The Mantra of Ruined Sluts
The ultimate expression of exploring ruined orgasms is what I suggested recently, reciting and committing to the mantra that you’ll ruin every orgasm you have, more than that, that a ruined orgasm IS cumming for you now.
When I cum it’s a ruin, when I ruin it’s a cum
The real mindfuck I play with a sub sometimes is by using this I change the language so she doesn’t even have a way to describe cumming properly ‘Cum for me now’ means ruin it, when she begs to cum, and I say yes, I’m only giving her permission to ruin. Early on she’s desperate, starts begging for a ‘real cum’, for which she’s sent back to edge repeating the mantra. It’s really fucked up and hot (and very Orwellian!).
Back to suggestions for my lovely trans girl followers though (love you all!). As you’ve probably picked up I’m a big fan of chastity devices for you. So my perfect scenario would be having you all caged up, fucking your pussy till your boi clit spurts – pulling out of course so it’s ruined.

Just watching it stream out of you in ruined glory, trapped, helpless, addicted.

Just remember good girls clean up their mess, no matter how much you don’t want to after a ruin.
As for you my little trans anon, you’ve nominated yourself to be my guinea pig (and get a bit of motivation in the process). Five days isn’t enough, I want more. You’re to do 7 days of ruined orgasms and write us a report on the effects, at which point I’ll decide if the experiment is to continue. No full orgasms without permission, at least one ruin a day, and on at least one day you have to attempt three ruins in the day.
Good girl.