Jack to Jackie - Crossdresser Caption Story

Boys becoming good girls, one caption at a time. CD fantasies, sissy slips, and those little moments where you forget who you were.

Brother To Sister

Every Boy Needs A Little Black Dress

This picture always makes me smile.

My boyfriend looking terrified on his first outing fully feminized, about to go into the movies. Notice I'm wearing jeans and he's in a dress to make him feel vulnerable all night.

I Discovered My Son In His Sisters Dress Now I Have Two Daughters

Woah. Is that girl on my bed…. my son?

Oh, hey mom, sorry ! was just looking through some of your old stuff from highschool and got a -little carried away It's okay, and you look very pretty. How about I set up my new DAUGHTER With the cute neighbor boy next door?

Girl Can Not Have Too Many Shoes And Pantyhose

My Future Is Female

Don't Give Up You Can Become The Woman You Were Meant To Be

Going To The Pool As A Girl For The Day Was Fun Girly Tan Lines Will "Force" You To Be A Girl All Summer

I Was Bullied As A Boy Now I'm My U Bullies "Trophy Wife"

Me And My Sister Feminized Our Brother He Loves Being A Girl

Girly Feminized Boys Are The Happiest And Prettiest Girls

See I Told You My Jeans Would Give You A Booty Like Mine - You're Welcome

You're A Cute Little Sassy Girl In My Outfit I'm Keeping You Like This Until You Learn How To Be A Polite Good Girl

Being A Prom Date Makes You Feel Momanly And Delicate

My Son Is A Girl At Heart I'm very Proud Of My New Daughter For showing Our Family And Friends Her Inner And Outer Beauty

Girls Always Have Fun Be A Girl Not A Boring Boy

You're Already Wearing Pretty Panties Babe You May As Well Wear Pretty Dresses, Lingerie, And Makeup To Go With Them!