Triumph!
I own my success, in no small part, to the advice from many people on the board, as well as others' postings. As of yesterday I can reliably and comfortably fist myself.
Around Christmas was the first time I managed, with great effort, to fit my hand wrist deep inside myself. It was amazing and a bit of a surprise. However for several weeks thereafter it was very challenging to repeat, and with minimal success.
I continued to focus on pain-free stretching. For discretion's sake I don't own any ready-made stretching plugs, but I managed to fashion my own toys. My go-to warm up was 2.4" diameter which went from 0 to 100% thickness in <0.5" of depth. My next step up (2.8" diameter) had the same sort of acceleration, even now it's super tight going in. My thickest toy goes from 2.8" to 3.1" within 4" of length (full length of 10" but I haven't made it past 5"); it is way too rigid but I make due with what I have. note: IMHO, a longer and more gradual taper would have been a big help.
A bit over a week ago, after stretching for 5-10 minutes I put the tools aside and tried fisting again. It worked, and much more smoothly! But the position was not comfortable at all:
Doggie style, hand reaching over my back between my cheeks, then pressing my forearm perpendicular against the wall and using the leverage of the wall to push inside. My ass felt fine, a VERY tight fit, but fine. It was the pressure against my forearm that was killing me, it felt tender for 1-2 days afterwards. I did this off and on every few days over the past week when the soreness in my arm was gone; the same position but trying different arm, wrist, and pelvic angles.
Earlier this week I struck gold. I used the same position but leaned *forward* (ignoring the wall entirely). I'd clearly loosed up a bit but the angle enabled me to get my hand wrist deep on my own. It was AWESOME! I was able to fist-fuck myself on my own. Yesterday I was able to do it without using any toys to warm up. Victory! lol
My next milestone is to continue loosening myself up so I can fist myself in more comfortable positions. The current doggie style is NOT conducive to jerking off at all. As good as it feels to fist myself... it would be an added bonus to do it while masturbating and cumming.
I just wanted to share that. Thanks everyone!
Onward!