Regrets

[Darkness]

I have 3

1. a boy told the other boys in the locker room that I was wearing tighty-whities. I was actually wearing white boxer-briefs. I regret not asking something like "So what?"
2. a wedgie fight occurred in my 6th grade locker room. I regret not trying to join in.
3. a boy told me to turn around so he could wedgie me. I regret not turning around.

[IrishWedgieMaster]

Oh I have a few. I kinda regret not making wedgies an expected thing that I do among friends. If I gave my friends a wedgie not it would because I don't really do them at all.
On the opposite side of that I regret not allowing myself to be wedgies one time. Basically my friend and I were wrestling on his bed. He was beating me pretty easily because I was much smaller than him so I gave him a wedgie to get the upper hand. I think he was really embarrassed about it because he got angry and tried pushing me on my side to give me a wedgie but I wouldn't let him and he gave up. Still I often wonder if I had allowed him to wedgie me if our wrestling would have turned in to a full on wedgie fight. Oh well ?

[Derek]

This is fun. 

One that I remember was when I was on a one year mission trip with a group of people about my age. We had to clean up trash for a service project and a girl I was friends with randomly, said she was bored and was gonna give me a wedgie and actually reached down my pants to do it (I was wearing a t-shirt tucked into khakis, the required uniform)but I flinched and jumped away and she laughed. I'm really only into guys wedging me which I why I did it but there were a few cute guys working with us that were in the area and would of caught it happening if it happened more than a few seconds, which I would of loved if they smiled or laughed (and maybe joined in, but probably not lol). And i was wearing pretty stretchy boxer briefs so it would of been a good one.

[wedgieboy]

My friend in middle school was always looking up my shorts and giving me wedgies hoping to catch me wearing tighty whities. He would always say things like, "It looks like you're wearing tighty whities today" and "If you're wearing tighty whities, I'm going to give you a wedgie like in the cartoons". Unfortunately, I was never wearing tighty whities at that time because middle school was when I switched my underwear to boxers, but I absolutely hated them. I wasn't wearing tighty whities again until high school unfortunately. So, I regret that I didn't let him catch me wearing tighty whities. I should have never switched from tighty whities to boxers when I had gym class. I was literally the only boy still wearing tighty whities when I took gym class in 6th grade. I didn't even know that people would just randomly switch their underwear to a horrible new style. All of my friends wore the same thing I did growing up, so it was a surprise to me.

[Fhall]

After she'd wedgied me once, my sister would always threaten to wedgie me if I didn't do things for her, and that'd always get me to. I wish I'd decided to not do whatever she'd asked once, maybe even egged her on.

[Tw4lyfee]

I had a roommate who liked to get his agression out by wrestling me. I wasn't much of a wrestler so he always won. Once I grabbed onto his short collar while we wrestled and he told me if I didn't let go he would give me the worst wedgie of my life, and even had my waistband in his hand. I regret letting go.