So, I've been with my boyfriend for just over 9 months now, we have a healthy relationship and I stay round his every weekend (sometimes in the week) and we go to the same college and have the same friends. Anyway, when we started going out I waited a while then told him I was genderfluid, he was seriously supportive of me and bought me a binder for christmas, then I went through some self discovery and realised I'm transgender. He paid for me to get my hair cut and uses male pronouns with me. We still have quite a lot of sexual contact, I enjoy being stimulated and so does he, however I don't enjoy being penetrated (due to dysphoria, it just feels wrong) I have a toy and he's bottomed a few times and enjoyed it, but he doesn't want it to happen all the time. I've been thinking about trying to receive anal with him, I love him to bits and I know sex isn't a big deal, and we don't have to have sex, I'd be happy to have a sexless relationship just with foreplay. He's told me he'd enjoy giving anal, and I want to try it to see if I enjoy it as a non straight man, however he's rather well endowed and I'm quite scared to try it. Does anyone have any advice?
Well, anal require preparation. Usually you start out with toys, small one at first, to get you used to it, before moving on the actual thing. But if you hate being penetrated, it might still be a problem for you, since it is somewhat a similar feeling.
Use lots of lube and go slow! Have him start with something small like a finger or a toy and then slowly work your way up to the real deal. I would also like to just kindly point you over to THIS super cute comic featuring adorable snails that might give a little more tips. Warning: the comic is NSFW