My Early Wedgie Life

Sister Wedgie

I don't recall how many times I managed to give my sister a wedgie, but these are the two most memorable times.

My sister is 5 years younger than me, so I've always been sort of the big bully bro. She was in my room bothering me one night, and we got to wrestling around. I managed to get her bent over and I saw my opening. I reached into her pants and started yanking on her pink Disney princess panties. She laughed whenever I wedgied her, not giving up on wrestling with me and losing. But I think we can all agree whoever is grasping the other persons underwear is the clear winner.

I wedgied her several times during this, nearly getting her undies halfway up her back. I became worried that she would tattle on me for giving her so many wedgies, so I let her give me one as payback.

I lifted my shirt to let her access my underwear. She started giggling uncontrollably as she pulled on my Hanes boxer briefs. I think they were grey that day. The wedgie didn't hurt and barely went up high. I think she was just more giddy to be pulling on my underwear.

The second time, was maybe 5-6 years later. This time, I was in her room to bother her. It was summer break, so we were home alone, and just like two siblings do, we started wrestling. I stuck her in a headlock and gave her a heads up. "I'm going to give you a wedgie!" I tell her.

She clawed and yelled for me to let go. But it didn't stop me from reaching into her pants, grabbing her white panties with green hearts and pulling them up. This wedgie didn't last long as she started to dig her sharp ass nails into my skin until I let go. I laughed and released her. She gave me a pouty look as she stuffed her undies back into her pants.

Wish I could remember any other times, but I hope you enjoyed this tale!