Hey Lake!
Writing this from my hospital bed in my own room. Hooray! Coming out to my OT paid off! Also noticed that male nurse always attending with a female one. That's new. Strangely reassured by that despite my anatomy mismatch but I feel more comfortable psychologically!
Ha! Sorry, but my initial reaction was to chuckle when I read your rant! I've experienced similar, so agree with the other posters. It's trial and error. Even same brand trunks eg M&S differ in style from each other - some have ridden up a little bit but others not. The best ones I've found so far for not riding up my legs at all are Marks & Spencer 2 Pack Autograph Plain Trunks with Modal - £15.00 Product Code: T144903A. They are a bit longer in the leg than my other M&S ones (the picture doesn't give a true idea of that) as well as being uber soft and comfortable. I'm waiting for a post Xmas sale and will be straight online to order a few more packs despite not being cheap! They are the best by a mile so far for my legs. I have large thighs - muscular but with darned woman fat on the insides at the top, which I despise. It's gotta go!!! FYI - I bought my correct size for all my M&S underwear and these Autograph ones are perfect. My other M&S trunks are 85% ok. They're a little shorter in the leg so do ride up a bit but they don't become uncomfortable or annoying. I just yank them back down over my woman fat when getting undressed. Otherwise during the rest of the day, they're not bothersome.
Don't do what I did initially in my desperation and buy a cheap supermarket multipack of men's trunks! I was away on holiday and completely dysphoric so in my haste, whilst getting provisions, I visited the men's clothing aisle. OMG. Not a good first experience of men's underwear! The seam was in the middle on them (I didn't know different then) so not meaning to be crude, they kept working their way into my back crack every 5 minutes. Needless to say, I spent a week constantly fiddling with my darned underwear as I wasn't ever going to resort to my women pants!
My advice is therefore look for trunks etc that don't have a middle seam, none of my 3 M&S multipacks do, nor do I think better manufacturers make them that way. I note that they're not cheap but in this instance, I'm glad I spent the extra money as I have 5 pairs of supermarket branded ones that are useless as underwear. I might wear them as night shorts occasionally but nothing more than that. Or bin them...!
I LOVE wearing my men's M&S trunks and I adamantly refuse to wear women's ones ever again. I even proudly wore my trunks to theatre for my surgery, which were obvious when it came to the dreaded bed pan time in recovery afterwards. The female nurse looked very surprised! I found it amusing but I didn't want to feel ashamed.
The other posters are right. I know of a couple of lesbians who wear men's underwear. My wife wasn't initially very happy with me wearing them but after a couple of weeks of edginess, she no longer comments. I don't know if that's a good thing or not as she doesn't say 'hey, you look as sexy as h__ll in them' but nor does she say she's not comfortable with me / my reasons for wearing them. I have exuded more self-confidence since wearing them though. Maybe she's resigned to it now, or just keeping schtum to not hurt my feelings. If only I could be more open with her and she still accept me for who I truly am. Maybe I'm not giving her enough credit. I have a binder but that's currently hidden well in the back of a wardrobe until I can wear it more once I've shed some chest fat. Will only be able to wear it on my own initially but I would like to think that would change as time goes on. I can't go back to hiding permanently in my female body anymore.
Let us know how you get on with future pant purchases! :-)