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I (23M) met up a few times with the eldest guy (68M) I've met up with.
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If anyone has any guidance or similar experience I'd appreciate it. This is a new experience for me.

He found me on Grindr and messaged me saying I was a good looking guy. Nice self esteem boost for me, especially being a trans man. After that we started chatting and we have met 3-4 times in public and I've been in his flat 2-3 times. He's showed me around more of the town he lives in as I'd only been there 2 times before I met him and he's been very fun and generous (giving me books to read, treating me to dinner) with me. He owns a bookshop and we both have reading books in common. We haven't had sex yet, but we did look at a book with nude art whilst being naked in his bed and he has given me some books with nudes (mainly men) or smut. We also have talked about sexual things and flirted a bit in that way.

Because of his age he doesn't understand as much about things which weren't talked about much when he was younger such as what 'trans' means (he understands I was born female and transitioning to male and on testosterone, so I think it's just the terminology he doesn't understand), memory lapses and mild incontinence. None of this bothers me and I've told him that, these are just not things I've dealt with much with the 30-60 year old men & women I've been with sexually or also in some kind of relationship (I am bisexual). It means I have to find a different way to describe things such as my mental health problems which I won't go into here but do heavily affect my life.

I have had a hard time accepting how he could be attracted to me as he is practically gay and well I don't pass fully just yet, only to some people (usually other men). I'd only been with other bi men and straight men 1 "99% gay" guy before, whether for one time hookups, fwb or some kind of relationship. Even though he finds me attractive and has told me so many times, my dysphoria comes in full force because how could I ever be attractive to a gay man when in my head I look like a butch woman, despite passing to him anyway. He even likes my pre T voice (it hasn't dropped yet) and doesn't find it girly at all and finds nothing wrong with anything about me. I know rationally it doesn't matter that I'm trans because I am clearly a man to him and he will be attracted to me because he's a gay man and likes my appearance.

The only thing that seemed suspicious was that I figured out he lied about his age to me. He initially told me he was in his fifties (it's not mandatory to set an age on Grindr) and I didn't question it from his appearance, he didn't appear near 70 to me. However he'd told me what year he was born during conversation and I'd used my phone's calculator to work out how old he'd be out of curiosity but also confusion since my granddad was born in 1940 and he's turning 84 soon, nowhere near 50s. The calculator said 69. I asked him on Grindr why he'd lied about his age, saying his age didn't bother me but rather I was confused that he'd been dishonest with me. He told me it was because he wanted to make finding a guy easier, which makes sense to me. He came clean and he said he'd be turning 69 this year and we moved on.

I'm not 100% what will happen but I'm happy to "see what happens". We haven't even kissed yet but I did rub his shoulder in a casual way before I left his car to go home the other night. I haven't told anyone else in my life about this, although I don't usually tell people much about my sexual/relationship life anyway. I would tell my best friend/ex (47M, also bi) but he finds my attraction to 60 year olds confusing so I know he wouldn't be horrible about it but I doubt he wouldn't find it very odd. My family is a definite no as well, I never even told them about my best friend when we were together for 3 years until September last year due to his age and because I got groomed by a much older man when I was 18-19 because of autism. I feel uncomfortable telling my family this stuff, plus I don't have the most typical relationships as I am aromantic but sexually attracted (out to 2 of my siblings but not my dad nor my younger brother, I'm out to everyone as bisexual & trans).

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6 months ago