Could your athletic performance in high school have been better if you'd had a childhood friend who was a tomboy cheerleader?Her cheerleading practice would've been at the same time as your PE classes. Sometimes she'd come over to cheer you on in her cute, sexy cheerleader outfit.What if she had been a bit concerned about your athletic performance and offered to do some personal training with you after school?
>>84863770I might have a cumbrain but for some reason I thought this was going to be NTR.
>>84863770I'd have her teach me how to do handstands and cartwheels so I can get flashed by her panties. I'd become the fittest boy in school with this kind of encouragement.
>>84863770>Going on a run with her.>She says:>"Loser has to perform oral sex to the winner!">Runs offWWYD?
>>84863820But what if she wears shorts under that skirt?
>>84863846Hmmm. That's very Tomboyish I suppose.>hey uhhh, have you ever thought about wearing spats? I think they'd suit you. I mean, they're fairly popular among girls now I hearGotta ease her in with a bit of deception and work my way down to panties. Maybe even nopan.
>>84863880Easiest way to do that is to make her pee herself.
>>84863820>this type of cleavageHottest thing ever!!!
>>84863898How ls that so?
>>84863914Search downblowse on pixiv or gelbooru
>>84863770Yeah it could have been but the idea of a tomboy cheerleader seems like a paradox.
>>84863927>Pees her shorts>Only the skirt left>Tell her it's okay
>>84863960>downblowseThanks anon!
>>84863994Being the gentlemen gamer and good friend that I am I'd offer her my boxers so she doesn't have to walk around with wet shorts and panties.
>>84864058But what if she refuses?
>>84864157I don't think I could be friends with such an accident prone girl even if she is a tomboy. Her going pantsless for the rest of the day means people other than me might accidentally see her and we can't have that!
>>84864211Hey, don't be mean!You teased her until she wet herself, that was your fault.
>>84864434She wet herself on her own! I had nothing to do with it!>Put on my boxers and be more careful next time. Heh, pisspants!
>>84864538You're so mean!!She thought she could trust you to not be judgemental.
>>84864600That just makes it sound like she pissed herself on purpose! Testing the waters too literally!
>>84864633And what if she did? Would you judge her? When she expects you to be there for here?
>>84863973idk it works for some cases
>>84864655I am there for her! Hence the offer of boxers so she can keep her modesty. Funny, she turns out to be more of a perv than me.
>>84863770I know this is AI but tomboys partaking in traditionally feminine roles is my fetish.
>>84864678>Childhood friend tomboy who is secretly a huge pervDiamonds I am.
Oh how I wish I could have had the balls to ask one of the hot cheerleader stacies in my class to let me have a sniff of her uniform socks, I wonder if she'd accept out of pity. That was a decade ago though and now I'm a total loser
tomboys and cheerleaders, a proper overrated + overrated combo
>>84864861Also probably the town's bicycle
>>84864861Tomboys are overrated maybe, but cheerleaders are girls that you just had to see irl to get.
>>84863770She looks like she likes to peg
>>84863770Thats if you manage to keep the tomboy.
>>84863770>it turns her on when she sees you get beaten by the jocks
>>84863770>conventionally attractive woman with short hair>"tomboy"
