Stories from days past, you can find masterposts for series here about older stories, you can also post your favorite older stories here as well, be sure to credit the author.
My step sister Chrissy is half japanese. Skinny, small, sort of nerdy with short black hair but she's still cute. She's also very shy and timid. Both our parents work long hours so after school when no one else is home we like to play little pranks on her. One day my friend Billy was over and we were down in the den bored. My sister was in her school skirt still and was laying face down on the couch reading a magazine. I can tell Billy is attracted to her although he has never really said it.
When we went into the kitchen to get a drink I told him, "Hey do you think my sister has a nice butt?" He just looked at me in silence with a smirk.
"Do you want to see it?" I added with a bigger smirk. He looked at me like I was kidding and just laughed.
We went back into the den and I put my finger to my lips and gave him a shhhhhh. Then I snuck up behind her and pounced on her sitting on her back pinning her face down on the couch. She struggled a bit trying to push up and said, "Hey!" but into the cushions so it was quite muffled. Next I pulled her skirt up past her butt exposing her flowery panties that were half up her butt on one side showing extra cheek. All Chrissy kept saying was "Hey!" and "Stop!" in her timid voice as she struggled in futility trying to get me off of her. I had her pinned down good though.
I grabbed the back of her panties and yelled "Wedgie time!!!" and yanked them all the way up her butt till they stretched out a good 12" disappearing up between her butt cheeks and crotch wedging way up her crack. I pulled so hard it forced her butt up off the couch leaving her arching her back in total awkward discomfort. I wedgied her panties so far up her butt crack I could see a good outline of her butthole area with her pussy lips being forced out both sides of the now straining thin strip of cloth wedged way up there. She said, "No stop! You're going to rip it!" but with her face pinned down in the couch cushions we could hardly hear her. I gave them an extra hard pull hearing the cloth begin to give way before letting them go then getting off of her quickly as I laughed my ass off at her. She jumped up scrambling to pull her panties out of her butt and crotch giving us a great crotch shot before hastily pulling her skirt back down into place. Red faced and embarrassed she made a break for it running out of the room but not before I dove forward skirting her, underwear and all, as she was exiting the room.
The site of her cute little naked butt wiggling away as she ran down the hallway bottomless and embarrassed was nothing short of priceless.
Billy high fived me as we both laughed hysterically for a good 10 minutes over it. This started the wheels turning on what other pranks I could do to her to strip and embarrass her....