It’s honestly such a tame thing compared to other things I see gay men be into, so I really had nothing to worry about. Every guy I’ve shared this with has been receptive and willing to indulge and give me wedgies in bed. I also love converting guys into tighty whities boys by gifting them tons of underwear.
Every once in a while now he’ll order me to put on my XXXL briefs to get in an atomic, jock lock, or shoulder wedgie and be stuck there for an extended period of time. Often I’ll wear multiple pairs so I can have on multiple wedgies or to wrap around my wrists or ankles instead of rope. I love just being restrained there while I’m teased or even ignored. Often I’ll have a regular sized pair of tighty whities under everything so I can still frot or get rubbed through the fly.
Never be too shy to tell them!