Growing up bring the youngest, I was always dressed in my three older sisters old costumes. Bratz outfits, Disney princess dresses and Nurse outfits were just some of the many clothes I wore. Snow White was my favorite. Not only dressed in gowns and somewhat slutty outfits, but my nails were painted, fingers and toes, and wigs were worn.
Of course pictures were taken with many still shown today. However, after awhile I started dressing myself in these clothes without any help or knowledge of my three sisters, Viola, Samantha and Carly.
I loved my oldest sister Carly’s many bikinis. Each and ever color of the rainbow. Strapless pink bikini top and slutty thong purple bottoms were just some of my many choices. But unfortunately they were all in the highest cupboard in her room so my chances of wearing these were less than few.
But down in the basement was where we kept all our old clothes. And one day when I had the house to myself, I snuck down and got started. Firstly I brought down Carly’s pink floral lace panties and a pink & black bra to go with it. I stripped off my clothes and tucked and tapped my willy. I slowly slipped on my panties. I could feel the lace around my waist.
Next I put on the bra and hooked the clasps on the back. I stuffed it with tissues as I had seen Viola and Samantha do so many times before. Next I wore Carly’s old skinny blue jeans with my panty-lines showing and lace whispering above my hips.
I put on a small belly t-shirt Viola used to wear, clearly to small for me now. Next I ran back upstairs to put on some makeup and paint my nails pink. Finally I grabbed a wig from the attic. I went into Carly’s room and stood there in my skinny blue jeans and black belly top with my Lacey panties on display along with my bra straps capturing anybody’s eye.
As I was posing and admiring myself in the mirror, pretending to be a real girl, the door suddenly flung open and I was caught with a flash of a camera from all my three sisters. I was caught red handed and my sisters started teasing me and I was so embarrassed. I tried to run away but they didn’t let me and took more photos and videos. Finally, after a lot of convincing, they let me go and this was how I was caught crossdressing the first time.
Submitted by Bethany
Nice story We have the older sister thing in common When I was twelve and my hormones were raging I suddenly remember stealing two 50’s classic full open bottom girdles with six garter fasteners I took them from the washroom we shared with a woman in the basement of the large building my family shared with that sexy dark haired beauty who looked like Della Street the woman who played Perry Mason’s sexy well dressed secretary So I stole two lovely girdles from the neighbor and hid them under my mattress My room was upstairs and I could strip, put on a girdle and wonder at how great I felt My neighbor caught me going back to the treasure trove of her bras, panties, slips and girdles and stockings hanging to dry a few times! So I has 5 or 7 pieces of her lingerie, some stockings It was what I now know to be small/petite but was way to big for me! I was only six years old and I had been stealing the young beauties lingerie and trying it on and literally rolling around in ecstasy on my bed! This went on for about two weeks Every time I got naked and put on her various lingerie I was so happy, exillerated and terrified my older sisters would catch me When the neighbor lady caught me in front of the washing machines with automatic rollers that flattened the clothes and pressed that water out somewhat Anyway, there I was in front of the washer, naked and wearing silky smooth briefs a bra and a lacy slip! I flipped! I cried, I was so terrified! I just knew she was going to be very angry and surely take me to my mom! But that very loving twentysomething beauty held me and calmed me until I stopped trembling Then she pulled me on her lap and held my face against her wonderful tits She told me she wouldn’t tell my mom because she would be real hurt and pissed! She also told me I had to not do it unless I was positive that nobody
was around And she asked me if I liked her and would like to come to house So she told me i should only wear her soft slinky things with her! I only went over there a few times then forgot all about her and her lingerie But the time I got into my older sisters’ panties and pantyhose in 1971 when I was twelve made all of those luscious memories come flooding back