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When did you stop wearing briefs

That's too bad you should at least have gotten to see her thong once if she got to see your briefs. That's only fair! Or I think you should have gotten more for that... Was she the one who saw you wore briefs and started the wedgie? Do you still know her today
 
Spearhead said:
That's too bad you should at least have gotten to see her thong once if she got to see your briefs. That's only fair! Or I think you should have gotten more for that... Was she the one who saw you wore briefs and started the wedgie? Do you still know her today
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Yes I lost a lot of confidence that time lol, some thong slips to ease the pain would have been welcome! She was not the one who started, it was one of the guys. He probably had the red line trunks or something and that's why he knew. I live far away today, even in a different country, so I don't meet them and haven't for ages but I follow her on Instagram so we haven't lost contact if that's what you mean. I said I wasn't into her back then because she was a little bit boyish and it was a little bit disappointing because I knew she mostly had normal panties, but today I realise she was very pretty and proper wife material... you can always dream.
 
AllThongsConsidered said:
Looking back, do you think you could've pulled it off after she found out about the tightie whities? :LOL:
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Haha, maybe... but only if she'd actually been interested in me, and honestly I don't know if she was. Back then I wasn't into her at all. I don't think they were judging me either. It felt more like curiosity than anything else. If I'd just admitted it and laughed, it might have ended with a few smiles over a surprising confession.

Looking back, wedgies and the whole "guy gets caught wearing briefs" gag were everywhere in movies when we were kids, especially in the early 2000s. This was probably the first time something like that felt real instead of just a joke on screen. Since we were close friends, it probably felt safe to embarrass me a bit for a shared laugh. I was definitely humiliated, but I think I took it harder than they expected. For them, it seemed more about the novelty and rare chance than trying to single me out. I can't blame them though, before my doctor told me to switch to briefs, I probably would've wanted to join in, or at least watch, just to experience it myself.

If they'd kept pushing it, or if the guys had forced it just to get a big reaction out of her at my expense, then yeah, that would've felt more personal. But she jumped in on her own, and I probably made things worse by getting weirdly defensive, which may have sounded like I was lying. That could have made them feel justified in calling my bluff.

Honestly, she probably just hadn't seen anyone wear briefs before and was curious. Boxers were way more common and everyone knew it, so I doubt she expected any of us to wear them. She didn't laugh hysterically or say anything mean. It was more like genuine surprise, wanting to confirm if it was true and see it for herself.
 
I stopped wearing briefs when I was in middle school when we would have to change in front of everyone. I remember to this day one or two kids were still wearing tighty whities. One kid I remember always changed at the end of the lockers and had the classic white FTL tighty whities.

I switched to boxers and hated how the seam on the butt would ride up giving me a wedgie, so I made the switch to boxer briefs. boxer briefs would cause chaffing, you would get wedgies in your groin all the time and I started running track and playing football so I decided to make the switch to briefs again I think Junior year of high school. But this was a silent switch. I didn't tell anyone and if I had to change for practice I would make sure I wore compression shorts under my pants so no one would see me in briefs. Come to think of it that wasn't even a good idea because Im sure they would see the VPL lines OR see my underwear entirely when I wore white compression shorts lol

Anyway, because briefs always gave me the support I needed when I was playing sports and did not create the issues that boxers and boxer briefs did, I stuck with briefs from then on. Now I wear briefs on the regular and classic tighty whities at home or at the gym.
 
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