I also have trouble with the gag reflex. Some things that I read help, for example:
If I ate recently, the reflex is a lot more sensitive. Seems like the old adage of "wait an hour after eating before swimming" applies to getting the little swimmers too. (Applies to food and liquids, although just liquids dissipate more quickly, and a little alcohol diminishes nerve sensitivity)
Recent practice. I noticed that when I was getting more frequent action (with ones that were long enough)., it gradually took more to gag. What I read was twice a week (or more) between incidents would help. it seemed proved true for me. I also noticed that after a long dry spell, it was back to normal. But then in the next flury of activity it diminished more quickly.
Being relaxed & comfortable helps.
Never got good at DT, but it's normally a non issue. Don't meet many hung, and most weren't pushing for it. Though I do tend to envy the guys who can do it easily on pornos/xtube etc.
As for teeth. I had to have mine removed because of a medical problem. After the teeth were gone, well it was lousy, dentures were nothing like the real thing, you can't really feel food & whatever through them like you do with real teeth and pallet. I always loved sucking a nice cock since I was about 13. But taking the denturs out- wow, I liked a cock in my mouth even more and no worries about trying to keep the teeth from scraping! Added bonus- sucking a thick one for a while (say more than 20 min) always made my jaw ache. No teeth, don't have to open the jaw as much. Never a jaw ache since! (It had no effect on the gag reflex).
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