Difficulties with wearing a device? discussion

In a different thread, I described how the opening of my urethra gets irritated because the tip of my penis pokes out just past his cell bars and rubs against the fly of my boxers. By the end of an average day, this irritation is quite noticeable—it hurts significantly.

So, I’ve experimented with a few solutions:

1. Tighter cotton boxer shorts featuring an off-center fly opening (Fruit of Loom). The fit is tight, and the seams don’t press directly against my penis—both positives. However, compared to my current Duluth Trading Buck Naked boxers made of nylon-like material, pure cotton feels less ideal; after about an hour, it starts feeling like sandpaper. FAIL.
2. P’s panty liners. These are slightly softer than my regular boxers and maintain more consistent contact with my penis, preventing that “buffing” sensation. MODESTLY EFFECTIVE.
3. I recall reading somewhere on here that Lane Bryant’s Cacique underwear pairs well with chastity cages. So, I ordered a few pairs of their full cotton briefs featuring the soft-sounding Cacique sport waistband, along with some high-waisted “smoother level 1” briefs which are mostly nylon blended with spandex. They should arrive by late week, and I’ll share my thoughts next Monday.

Throughout all my years in BDSM, I’ve never worn women’s clothing (well, once—it didn’t go well; the teddy was way too small, leaving me stuck with an EVIL wedgie for two hours). Honestly, if I were slimmer, shorter, had smaller feet and more feminine features, it probably would have occurred to me ages ago as a fun activity. But here’s my reality: I’m a towering 6’4” and weigh 265 pounds—proper linebacker size. Little kids either run when they see me coming or point in awe yelling “Santa!” I expect I’ll look ridiculous.

P, bless her soul, has approved this attempt at comfort, though I anticipate she’ll have some fun humiliating me over it—which is half the joy for both of us.

This is all brand new to me. If either choice provides lasting relief while I’m locked up, I might wear women’s panties for the entire duration. So here’s my request: Sissies, cross-dressers, and other panty enthusiasts, please help frame this correctly in my mind so I can adjust properly. I LOVE how you all embrace your identity and activities with such confidence. Meanwhile, I feel like a hairy construction worker belching and farting while dancing in a tutu. Can you guide me to the mindset where I stop worrying about it—or even start enjoying it? Please accept this as a sincere request for help from an open mind.

Thank You! Jamie

I don’t want to pull you away from your feminization experiment, but have you tried briefs with a pouch? There’s been quite a bit of discussion about them here. The pouch offers support *and* extra room, reducing friction significantly. They work nearly ideally for me (the tip of my penis also extends slightly past the end bars of my Contender cage, which was an issue before I started using pouch briefs).