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I know a guy that started the process of being a tranny. Not just dressing up but he started to take HRT. And I just listened to him and let him talk, just asking questions like why or what brought that about and so on. When you're in that non-judgemental mode that's just listening and asking clarifying questions, people will just be open and tell you everything.
He eventually told me he'd been watching a lot of sissy porn. And went into details. I'd given him some time to just ramble a bit more and then I asked the question, okay so you're on these hormones that are going to alter your body permanently, what if this is just a fetish as result of the porn? Of course this got him to sperg out for a while but that but I ended the conservation with: how would you actually know the difference and he didn't really have an answer other than "feelings" and I didn't tell him he needed to do x or y, just given the nature of surgery and these drugs, it's a life altering decision so think about it long and hard and not just go by a feeling.
I didn't stay in touch for a long time, I would occasionally meet him via mutual friends and I would always be respectful and asked how he was doing and how his "journey" was going. Anyway, just this year he messaged me and thanked me, he's off HRT and is detrans. His family had been trying to reach him but it was always devolving into arguments. He had booked an initial surgery but then having to think about what I said on the long journey to Asia helped him get cold feet.
At the moment he has a weird wide waist that's similar to XXY people because of the HRT. It's also fucked up his dick apparently. But, he's super glad he didn't go through with the surgery because he said he probably would've killed himself realising what that truly would've meant.