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It's so fleeting, isn't it. Just a year ago i had a full head of hair down to neck level, now I cannot look like what I did for most of my life. Jarring.
Sounds like you're trying to fix an emotional problem with sex which truly doesn't make sense. Learn to separate your sexual needs from the emotional ones.
Asking for dick size may be rude and raise red flags if the person you're talking to is passive. Specially if they're not escorts. Most trans chicks want a vagina deep down.
The porn you jerk off to doesn't mean anything, it's not an indicative that you'll enjoy fucking twinks/ transgirls. Beware of becoming one of those guys that have disgust for themselves due to not knowing deep down what they truly want and decided to experience the real thing despite the glaring concerns in the first place.