maybe triggers..
Well, for me its been much, much easier since i started testosterone, and then easier still now that I've started pumping, it helps because when i fly solo, i can use the same actions as a bioboy, as in jerking and such, anyways! back to the main question, it really for me took a LOT of trust in my partner, she has known about my 'transliness' since we first met, but thats not to say she knew what to expect, I'm still her first transguy and we've had to learn together, i find that i get phantom limb a lot, so that makes using strapons easier for me mentally, I've tried the feeldo only so far, and after getting it through my head that its OKAY and normal to utilise what i have already got, thats been easier getting through the insertion thing, i find the thing that helps me the best is that she calls my junk, male names, we have a little trouble with naming a CERTAIN part of it, and i had a bit of trouble hearing "youre so wet" for the first time, i nearly died the first time i let 'i want you inside of me' slip out of my mouth but really its a trust thing, and it'll be enjoyable as long as you don't over think it, theres a myriad of tools available for you to use available for you if you're more interested in the more 'normal' styles of sex, but use your imagination, trust your partner, and just go with it, turn your brain off, and just relax, she/he isn't going to be judging you if you've been honest with your trans* status
im not sure i even answered one question lol :3 sorry but i tried