So I met the third man.

This time there was more of a trying out sissy side to the meeting, which started with just looking at porn.

And so we started to go through some of my weirder favourites (tentacles, shemales)

His cock was a bit longer than mine, and thicker too, and so I started to help him out with my hands, and then later with my mouth, and he asked me to dress up so I quickly did. No, I'm not convincing, but that wasn't really the point.

After a while of stroking/sucking/edging he suggested anal.

We tried unsuccessfully - not his fault in any way, but it just was a little awkward, I was too nervous, and he was just a bit too big, so after my ass was hurting we gave, and jerked off onto my stomach.

So at least I've tried out some fantasy things. I'm fine with having tried it (he was a gent after all) but I think I'll keep fantasies as fantasies in the future.

Think any future sex i'm likely to have is only with women (and maybe TS if I'm lucky enough).