Crossdressing origins

[AlexBailey]

I wanted to dress in girls clothes long before I was interested in sexuality. I wanted to be part of the crew with my older sister and her friends and get the same attention they received for being all so cute and pretty. She was a competitive ice skater and I got her hand-me-downs from the giveaway box in our garage.

 

[Easyvirtue]

LIke others here, started as a young teen. Had an older sister and saw her clothes, bra, and undies in the washroom. When no one was around, I tried them on and really enjoyed it. My parents worked and my sister had after school activities so I was often alone after school, so I would try some on. After my sister went to college, she left a lot of her high school clothes behind, including underwear, dresses, nylons. It was a smorgasbord. I tried all her clothes on. Kept at it till college.

Yes I hear that. I grew up with 2 sisters and my divorced mom. There were panties and bras and hosiery and girdles and such all over the house. At my age at that time I didn’t know why my sisters panties were sticky sometimes. Didn’t stop me from wearing them but now I know they either were masturbating or had them on after sex. Moms were never like that just had an arousing aroma.

 

[Sckrfay]

I was raised by my older sister. She first began dressing me at at 5. I loved it and never,ever protested.
This progressed to lingerie when I reached puberty, and debauchery. I enjoy every minute of this.
I am now an adult sissyboi ,and dress daily.
View attachment 2440384

sounds like a great sister! And you look fantastic!

 

[Tayloroc]

You’re so very femme. Just lovely

 

[Persuademe]

I was raised by my older sister. She first began dressing me at at 5. I loved it and never,ever protested.
This progressed to lingerie when I reached puberty, and debauchery. I enjoy every minute of this.
I am now an adult sissyboi ,and dress daily.
View attachment 2440384

 

[Persuademe]

Do you know how nice you really look ? I hope same lucky man is telling you that every day . If.not they should be. I’d whisper it in your ear , when I wrapped my arms around you from behind and ease into you .

 

[van_delay]

I was raised by my older sister. She first began dressing me at at 5. I loved it and never,ever protested.
This progressed to lingerie when I reached puberty, and debauchery. I enjoy every minute of this.
I am now an adult sissyboi ,and dress daily.
View attachment 2440384

Very pretty