I am a 14-year-old male (weighing 69 kg). I woke up in my black briefs and socks. I live with my sister and maid (my parents are overseas). Our maid is gone for holiday packing us food for 2 weeks.
Anyways, I got up and decided to get something from the fridge. I went to the kitchen, bent down to grab something and from behind, my sister (11) grabbed my underwear and gave me a wedgie. I said ouch, but I liked it. She told me to wear some shorts. I said I just woke up. I act cool around my sis, so I decided not to adjust my underwear back and let it be in the wedgie position.
She then dared me to eat breakfast in that pulled up underwear. I accepted the challenged. I just wore and undershirt and went to the dining table. My sis came and slapped my ass. I said not now. After breakfast, I washed my face, wore my red briefs, changed into my swimming trunks and went swimming. (I need to wear underwear underneath my trunks cuz my trunks are too tight and small and then anyone could see my butt crack.)
So, you could imagine my underwear was a bit higher worn than my trunks. I teach 8-year-old orphans how to survive if you are drowning. But most of the times we get horny (I am the boss, so no one scolds me) So I was teaching them about swimming on land when one of my student gave me a Melvin wedgie.
I smiled at that person and asked him to give himself a Melvin. He got shy and refused so I gave him a Melvin wedgie (he was wearing underwear as I recommend my students to wear underwear, so you can use your trunks as a rope to save people from drowning).
When I got back from swimming, I went to shower. After that I wore my blue briefs (light blue and they were one size tighter, so my bulge is larger). I decided not to wear shorts. My sister came in and gave me a Melvin. She went so high she saw my pubic hair from below. I got embarrassed. She slapped my bulge and watched it jiggle. She smiled, and I quickly adjusted my underwear before she sees my ‘dragon’. (For those who don’t get that, I am talking about my penis). I then wear my shorts.
My sis told me whether she could use me as a relief toy to relief her stress but by only doing a wedgie. I got a massive wedgie and she asked if I could pull my pants down. I said no. Went to my room, locked the door and ruined the fun for the day.