Boxers or briefs

[blurrd]

For a long time I have thought that tighter underwear helps keeping the skin pulled back but from my personal experience, when I wear loose boxers or when I'm naked (I love being naked), my foreskin stays back forever! My assumption is that without much squizing and rubbing aginst the pants my big glans naturally keep the skin from rolling back. Would love to hear from your experience!

[HeroicGlance]

You are on the right track - Believe it or not, I found that going without underwear at all helps the best.  Underwear was always in contact with my glans, which I found counter-productive.

Understand: only part of the goal is training the skin to stay back.  The other half is keratinization, which occurs best when the glans and exposed foreskin are exposed to the air.

Like me, it sounds like you're at the stage where unless you wear tight underwear, your foreskin retracts on its own - congrats!  The next step is getting used to letting your body do what it wants to do.

[rushmilk]

I love going without underwear. Love the feeling of my pants rubbing on my glans. Get's you used to the feeling and it is also a turn on for me

[Alexis1985]

I guess it depends, tight boxers hold it back for me but when I stand up  the material moves down and let's it slip forward which is the opposite with loose.

I prefer tight boxers with the flap, I poke my little helmet out and that stops it rolling forward

[ThePiemel]

For starters, briefs might be an idea to keep your skin in place. Just make sure you switch sides in where you keep your penis. Or it might get bent.

For me, summer is starting. That means no underwear, day and night. Favorite pants at the moment are trainers with a bit of style. Not the sports stuff. Stretch material. Feels very pleasant. So pleasant, I often put one on right after breakfast. Or when the postman rings. To make sure everything stays, I still spoon it. My shaft/prepuce skin still wants to creep under my inner foreskin while retracted and flaccid. Almost sorted but spooning the reverse helps that a lot.

Every other day another one, and one for the washing machine. With the sheets, because we both sleep naked as well. The whole lot shaved, ready for taking that heat. And a bit of sun on it to get rid of the color difference.