Heel Advice and Challenge Inquiry

I’m packing my bags for a long weekend getaway this Thursday through Monday. I bought a pair of 4-inch ankle-strap heels for the trip. My question is: when wearing these kinds of heels for hours, is it more comfortable to land heel-first like you would in regular or low heels, or should I aim to land toe-first and lower the rest of the foot?

As for plans and a bit of a challenge: With so much potential alone time at the hotel next week (since our conferences happen during the day), I plan to be crossdressed and bound to varying degrees every afternoon and evening. I’ll also wear diapers 24/7, even under my regular daytime clothes—I do this often enough that nobody notices. Currently, I’m trying on what will likely be my main outfit for the evenings. Most of these items have been used in past sessions or a trip last year, but nothing quite like this upcoming event.

Here is my current setup: A Tollboy-style chastity belt, pull-up disposable diaper (with holes cut into the plastic backing), a Poise overnight pad, and a Molicare super brief. Over that, I have two plastic diaper covers to ensure no leaks. I’ve tested this combination often; it allows me to stay bound for over 12 hours. On top, I’m wearing a white bra with stuffed stockings creating a nice bust line. Below that are panty hose, a waist shaper (the type you pull up like pants, featuring elastic around the thighs and buttocks, connecting to an elastic trim above the belly button), and a full-body elastic shaper over the breasts. Finally, I’m wearing a long black cotton dress with flowers, plus the heels.

Later today, cuffs and a gag will be put in place, and overnight I’ll be locked to the bed somehow. What else could I wear or do to make it more enjoyable? I have plenty of time on my hands. My collection includes many bondage toys and various clothes (underwear, swimsuits, dresses, etc.).

Quick update: I just walked a mile on the treadmill… heels are evil (but I love them).