I have freeballed for over 40 years now. Only time I wear any is doctor visits. Nothing feels better in the hot summer months than wearing lightweight polyester shorts while hanging weights off my balls.
Hi nice man.
Is there a reason why not freeballing during a doctor visit?
I also freeball when having a doctor visit. My doc is aware of it.
 
I have a female co-worker who freeballs in the sense that she never wears underwear.

She typically wears knee-length dresses or skirts with heels and *no* underwear.

I know this, not only because she has told me, but also because she gets a kick out of showing me the goods when I least expect it.
 
The usual for me is after the shower post gym I don’t wear any underwear. Spend the evening freeballing, sleep, then wear underwear the day after to go to work. Whatever I have to do in the evening (whether it is doing some chores, supermarket or hanging out) I’ll be freeballing.
 
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I had a pair of boxers that wouldn't stay closed and my penis kept falling out. That was so annoying. I can go commando just fine and like it. But, that was an uncomfortable feeling
 
I have a female co-worker who freeballs in the sense that she never wears underwear.

She typically wears knee-length dresses or skirts with heels and *no* underwear.

I know this, not only because she has told me, but also because she gets a kick out of showing me the goods when I least expect it.
That is actually called freebuffing. Obviously not a fan but my mate R who is a full-time freeballer like me had a gf at some point who “suffered” (for lack of a better word) from a hypertrophic and hypersensitive clitoris and could therefore not wear anything bifurcated. She unintentionally flashed us on more occasions than I care to remember. Actually made me apprehensive to look at her 😂
 
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I wear briefs and sometimes pull out my cock and balls from under the leg opening and let them hang down my leg so I call it sidesaddle commando.View attachment 202245261
In my opinion, seeing a bloke with a cock like yours wear underwear is almost sacrilegious. Apart from underwear being unhealthy, unhygienic and such, it just can’t be comfortable having your blood flow hampered all day…

I had a pair of boxers that wouldn't stay closed and my penis kept falling out. That was so annoying. I can go commando just fine and like it. But, that was an uncomfortable feeling
All the more reason not to bother with them!
 
My fuck bud has said it should be a leather cock strap this year - and no butt plug
Sounds like a perfect get-up. It’s the only thing I own that approximates ‘underwear’ in the sense that it is worn under something
Kilts are perfect for festive evenings, they look extremely dapper, offer warmth AND ventilation, and are ideal for surreptitious, subtle expressions of affection (either friend, or ‘special’ friend), or extensive teasing (the latter)