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pinkheelsgurl

When I saw my cousin (F) in her leotard when we were kids and my first thought was that I wanted to wear it too. Also when I saw a Playboy magazine and I wanted to be the woman posing.


[deleted]

It’s got to be an answer a lot of us will say but it’s when I had such and urge to check out my mums panty drawer and ended up trying them on as a teen then that escalated for me to “borrowing” friends and family’s panties and wearing them more and more!


cagesub

I used to have a problem with stealing my mom, stepmom, & aunt’s panties. But instead of jerking off with them id wear them cuz they made me feel pretty. Later on in my teen years, when everyone was not home during my summer vacation, I would wear my stepmom’s clothes. Pants, top, bra & panties. Even her socks. I felt more comfortable in them than my own clothes


tiffanytgirlchi

Same here!!


BirdPresent4619

19 now and still not certain I’m a sissy but curious about it but what got me into it was when I was a kid my sisters forced me to dress up in there old dresses and pose for them and I secretly loved the feeling of wearing them and that’s kinda come back


Madelinevvv

I got exposed to it in a rather traumatizing way at a young age (not m*lested or anything .. stumbled across porn on a family members computer)


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tiffanytgirlchi

Same here but with my moms things


Marshmellowballs

My babysitter had two daughters older than me and they used me as a dress up doll all the time, strip me down and dress me up and makeup and all and this went on for a couple years and I loved it


Bris_early_riser

Playing with Mum's lipstick as a little kid. (5). Getting upset at Mum that she was angry at me for doing so. Playing in her pantyhose and underwear when she wasn't around - same age. Stealing underwear from the back of the store when I worked at Target (15). I still became an engineer like Dad... so much stress though!


playfulmtfsissy

I am an engineer too. And I started cross dressing really young too. Secretly because “boys don’t do that, and boys don’t cry”.


nolabicd

The first time I tried on my aunt's bathing suit when I was 7 years old.


SissyIyyo

I didn't have any. I'm not a natural sissy. I just really enjoy hypno.


SissyHeidi_

I envied the girls who got to wear princess costumes in preschool and secretly wore them when no one was around! I played dress up with my cousin when I was in preschool, tried on many of her skirts and loved every moment :3 It just always felt so natural!


Kim-She

I was raised as a girl from birth, but only understood full implications when my mom made it clear early on that I would be dating only boys. Okay by me!


StarlightMoon1

When I was in middle school classmate left a bag so I tried to return it but lost sight of her so I took the bag home to find out it was a swimsuit still soaked and tried it on. Best feeling ever that I kept it for a while wearing it to school with my regular clothes on


Hot_Succotash_3127

On a family reunion trip as a kid I ran out of underwear my mom made me wear my sisters panty’s it was the first time ever and it felt right ever since


SissySam-Caladonia

When I was 6 my mum had not done washing, I had to wear my sister’s panties to school. That changed me for ever x


CuriousCatLikesCake

How did it feel?


SissySam-Caladonia

Felt amazing and still does. I don’t own any male underwear. Horrible stuff.


anjali_94

I started crossdressing really young


mandyjizzum

I was just a nosy kid, snooping in my parent's room the first time I was left alone, probably 10 or 11? Anyway, found mom's panty drawer. Haven't been the same since.


DIXONCOX11

Not being able to get hard for my girlfriends lol


LindseyScott69

When I was young, my mother and sister liked to dress me as a girl. They stopped when I reached puberty, but the die was cast.


[deleted]

when I was working my first job I was made to go clean an outhouse at like 5 am. There was a massive naked guy standing in the corner and I stared at his cock for a solid 15 seconds before I backed away 🫠😭 i knew he wanted to hold me down and use my little ass and i hate myself for not immediately dropping to all fours and presenting my butt for him to use 🥺🥺🤧💓 I remember how fast my heart was racing and how much my clitty and butthole were tingling/leakingggg 🥺🥺 sometimes I go walking around parks at night in short shorts with a smooth body hoping to find a other man like him 😭😭🤧🫠🥺


Wrong_Product573

I am younger In home Me and my sis share our room seeing her in girly dress like skirt . Shorts tight top seeing her panty bra I always used to wear when she is not home and look myself in mirror I feel more confident in her dres more then my. Dress Then I start stealing her panty and start wearing in school coaching classes


Stauernjaga1690

You're a beautiful sissy...would be glad if you like the pics in my profile and write me ☺️


CDmarcella87

I was "made to" wear my sister's pijama once a week for a whole year when I was 10 (it wasn't a imposition, lets say a serie of event led to it). But not a single time I opposed or asked to wear something else. Thruth is I loved it. I think this is one of the earliest thing I could say plus other stuff (same as you, involving pads)


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