What age did you change from briefs to boxers?
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17 AKA first year university when I started buying my own clothes.
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14-15
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I never changed from briefs to boxers. Growing up in Australia in the 80s, no one wore boxers. Everyone wore basic coloured hipster briefs (really boring). However, I desperately wanted to change to "tighty whities" briefs.
The only guys I ever saw wearing them were on American movies and TV shows and I thought they were so sexy and mature. Little did Iย know that every American boy was trying not to wear them and change to boxers instead.
When I was about 15, I managed to convince my mum to buy me briefs that had a fly front. Initially she bought me coloured Jockeys because she thought these were more "modern". But the next time I needed new underwear, sheย bought a 5 pack of Classic Jockey Y-fronts because they were cheaper. I was so excited - I couldn't wait to get home and tear open the pack so I could try them on. They are still my favourite type of underwear. -
never.
a hard button on underwear is the greatest sin. boxers must have no button (or be cut off) to be wearable imo, which kinda limits them for me to "lazing about the house" where it doesn't matter if theres escapage.
stopped wearing briefs at about 14-15 though, but boxers do nothing to contain raging teen-boners in school. such embarass. i only wore them on my birthday to avoid the pain of the ritualised birthday wedgies

otherwise, boxerbriefs/trunks/hipsters/whatever-you-want-to-call-them for life.
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I think around 16-17, and it was the best decision I've ever made.
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12/13
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Eleven (11) years old, when it became necessary to change into gym clothes for P.E.
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Probably about 13. You'd be an absolute outcast and ridiculed if you wore y-fronts at school.
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I never changed from briefs to boxers. I have changed from briefs to Jockstraps though.
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In my teenage years...

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@ckslad I switched to boxers when I was at university (age 18) but went back to briefs a few years later because the sensation of things "swinging free" caused too much arousal for usual daytime tasks. I remain a briefs person to this day.
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