I am a top but all my life I have fantasized in being a woman getting fucked by men. In fact this is how I often masturbated until I reached adulthood.
I'm currently training my butt using plugs and dildos because I want to experiment penetration. However, it still feels uncomfortable.
I do get pleasure (with the plugs especially) but also some pain when using dildos. When I try to move it in and out to emulate sex I still don't feel an orgasm. I reach it usually when jerking off watching movies with it inside. It's been 2-3 months since I'm learning. I do it once a week usually, sometimes twice. I need tips.