When did you realize you where a sissy

[Tiffany]

I remember when I was 16, nobody was home and I tried on my sisters cheerleader outfit. I would continue trying different things whenever I was home alone. I would put on a bra and stuff it with socks and randomly pick out an outfit and look at it in a full length mirror.

[spoonchicken]

At the age of 30 when I tried on a pair of panties and instantly got a very powerful hard-on.......that's when I knew I was "on to something"...

[CDLover]

When I baby sat, I would go and try on some of the mother's clothes.

[sissybabyclaire]

I started wearing my sisters panties when I was 12. I have done so every since including with many girlfriends. I enjoy it so much that one girlfriend wanted me to throw my male clothing and wear only girl clothing. That is what I wished I would have done but did not. I am a sissy and now in diapers and plastic pants.

[deewet]

When I was young and visiting my grandmother for days at a time, I often searched through the house, and I stumbled upon a chest that had a lot of my aunts older things from when she was growing up.

[BabyJune]

Age 4 or five when I observed that the lives of little girls seemed much more pleasant than the lives of little boys.

[CDLover]

CDLover, you are a brave one, finding and wearing things when babysitting- so much could go wrong with that scene.

[Rachel Emily]

Age 4 or five when I observed that the lives of little girls seemed much more pleasant than the lives of little boys.

[Diaperddiva]

I used to try on my sisters Swimsuits and panties when no one was around. I was probably in my 20s before i bought my first panties. I've had girlfriends, and also my wife when i was married buy Victoria secret for me. I love my sexy panties and am happy i have such good friends!

[sissydrew]

I used to wear my mom's clothes and wanted to be a pretty girl for a while. Now that I've grown up, I realize that I'm a CD sissy, not trans.

[repetitivediaperwetter88]

when I wore my first, (Very First) sissy dress which was a few days ago

[DiaperedCutie]

When I was 13 or 14 I remember taking a skirt and top from my sister's laundry and trying it on over my diaper just for fun in the mirror, and I couldn't believe the thrill I got from it.

[itzKiT]

When I was about 8 or 9, I used to live with my uncle and my female cousins. I remember one night, they convinced me to dress up in some of their dresses and skirts. They had me put on some panties. Nothing ever felt so close to right. Ever since then, I've grown my own collection of panties, skirts, etc.

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[Becky]

I must have been ten or eleven when I first started playing dress up games with my little sister, when our parents were out, of course.

[Tessa Virtuous]

I must have been eight or nine, I was at a discount department store with my Mom. She was buying a dress as a present for one of her friends daughter. I guess she was the same size as me (at 8 or 9, boys and girls are build the same). I complained when she had me try it on, but really I loved it. After that any time I could find a dress or skirt to put on, I would.

[PullUpDiaperLover]

These kind of questions drive me nuts. I was always a Sissy, but like everything sexual my own path to discovery took a lot longer then many. Shyness I suppose. Really not until recently, but the writing was on the wall for a long time.

[deewet]

When I was 5 or 6 one of my aunts took advantage of my fairly long and naturally curly hair to use me in a class play they were

[diapered charles]

I was about 14 or 15 and tried on my girlfriend's shiny green metallic satin panties. They felt so good! I started trying on everything I could find whenever I could scrounge up a discrete moment. It took a long time for me to accept it.

[Backindiapers]

About the age of 11 maybe.

[babytammyjean]

I realized over 20 years ago that i was a sissy.

[sissypaul]

I was about 8 on a visit up north to see some cousins for the first time. They were 5 girls between 6- 16. The older girls were charged to look after my care whilst the adults were left in peace to catch up on lost time.

Then being led upstairs to an attic play room I soon found myself becoming under jibe's and protests that they had to play with a boy and to that end they all agreed that I had to be dressed as one of them. Before I knew what was happening, I was being stripped to my underware by the two eldest girls as the others went to find suitable fitting clothes.

My protests were in vain as my now naked body, which was providing much laughter, was soon being dressed totally in all girl attire suitable for my age. Once my hair had also been attended to , I was then led to a mirror to view the outcome of their transformation.

Wow even I couldn't believe what I was seeing, a pretty girl looking back at me.The seeds of need had been sown and from that day onwards my desires have always included cross dressing.

[baby busdriver]

when I was 12 when my family went out left me on my own great time I had I use to wear my sister s or my mum dress and panties and tights .then when I left home live in staff house with female's used looked in bin for there old tights to wear .but last ten years I been out buy own dress and skirts and panties and tights . then when

[ssdiapers]

Funny what a pair of panties can do.

[Johnny O]

When I was little and naughty (around 5-6 years), my mother would do almost anything to get me to stop annoying or teasing my sister. She eventually found out what worked. She threatened to put me in a dress, wear lipstick and go with her to the hairdressers for a perm. She made good on the first two items but never took me to have my hair and nails done. Well, as time passed, I experimented a lot with my sister's and mother's cloths and make-up but never felt like a sissy until years later when I woke up one morning and had an epiphany. I suddenly remembered those early days and really wished my mother had taken me to the hairdresser all dolled up. The thought of being made into a girl and dressed up in front of a lot of staring and smiling

[deewet]

When I was about 5 years old, one of my aunts who was very active in