How did crossdressing start with you all?

[Ali123]

Started with my sisters navy blue school knickers, they were so comfortable compared to my y fronts, still love wearing school knicks now, adult size obviously and sometimes wear them over a nappy

I love wearing a nappy under my schoolgirl uniform too. I bought some vintage nylon knickers to wear with them, although mine are bottle green.

 

[Tommy10]

That’s so kind of your friend’s mother. Did she tell your own mother?

Nope. My family was/is very conservative, so I think my friend's mom understood how things would've gone if she told them. Times change, and my family is much more supportive now, and accepts some of my wardrobe choices

 

[LittleMaya]

have had tights and leotards since age 11.

HOW were you fortunate enough to have your own tights and leotards at age 11? I had nothing of my own until I was old enough to ride my bike to the nearby city and shop for myself.

 

[LittleMaya]

My mom tried very hard to be progressive as she was going through the 60's and early 70's as a young adult and she was conscious of avoiding gender norms so they both agreed that, assuming I behaved myself, they would let me borrow and wear some of her grandaighter's clothing on future visits with privacy ground rules in place.

60's and 70's ??? Your mom was very progressive indeed !!! I had only wished.

 

[NannaAnnabelle]

60's and 70's ??? Your mom was very progressive indeed !!! I had only wished.

My mom was obsessed with "getting it right" when it came to parenting me and my brother. Her and my aunt attended a number of parenting workshops and she read a lot of the progressive material that began being published in the late 60s.

I'm not sure what my neighbor's motivation was. I'm guessing she found it cute as well as having a built in playmate for her granddaughters? Either way I was ok with it. I liked being a boy but it was also fun playing as a young girl. It was a nice escape especially since I was bullied quite a bit back then.

 

[Angelapinks]

HOW were you fortunate enough to have your own tights and leotards at age 11? I had nothing of my own until I was old enough to ride my bike to the nearby city and shop for myself.

I had a paper route to earn most of my money and also did grass cutting for all the old ladies in my area. There was a small Department store near our house and I would browse often looking at all the plastic baby pants and girls clothes. One of the sales ladies would come and ask if I saw anything I liked and after awhile I told her what I really wanted, some girls panties and some pink plastic baby pants. She asked me how much money I had and then picked some girls things in my size and the Toddler size plastic pants and went to the cash desk. I was very ashamed to be buying them but tried to tell her they were gifts for family. After they were bagged and paid for she said I know the way you look at these things that they are really for you and that's OK. I left feeling very strange inside but by the time I got home I could not wait to try everything on. The next time she was in the shop I asked her about a black dance leotard and some pink tights. She said her daughter took dance and showed me what they had and I was in love with the feel and the excitement of wearing them. I gave her all the money I had and was 50 cents short so she put it in for me and I said I was going to bring it to her as soon as I had it. She told me I was one of her best customers. Sadly the store closed by the time I was 12 or 13 and I never saw the lady again but she did on one occasion tell me her brother liked to try on her clothes when they were younger so it was not new to her.

 

[LittleMaya]

After they were bagged and paid for she said I know the way you look at these things that they are really for you and that's OK.

She told me I was one of her best customers. Sadly the store closed by the time I was 12 or 13 and I never saw the lady again but she did on one occasion tell me her brother liked to try on her clothes when they were younger so it was not new to her.

How incredibly kind of her, and how very brave of you !!!

 

[Angelapinks]

Maybe not so brave as obsessed with getting girls things but then I have always considered myself a girl. I just could not get anyone else to see it and when I was younger I had to stop taking about it under threat of being put away. I am so glad Transgender kids today at least have some support and understanding.

 

[Seasonedcitizen]

I had a paper route to earn most of my money and also did grass cutting for all the old ladies in my area. There was a small Department store near our house and I would browse often looking at all the plastic baby pants and girls clothes. One of the sales ladies would come and ask if I saw anything I liked and after awhile I told her what I really wanted, some girls panties and some pink plastic baby pants. She asked me how much money I had and then picked some girls things in my size and the Toddler size plastic pants and went to the cash desk. I was very ashamed to be buying them but tried to tell her they were gifts for family. After they were bagged and paid for she said I know the way you look at these things that they are really for you and that's OK. I left feeling very strange inside but by the time I got home I could not wait to try everything on. The next time she was in the shop I asked her about a black dance leotard and some pink tights. She said her daughter took dance and showed me what they had and I was in love with the feel and the excitement of wearing them. I gave her all the money I had and was 50 cents short so she put it in for me and I said I was going to bring it to her as soon as I had it. She told me I was one of her best customers. Sadly the store closed by the time I was 12 or 13 and I never saw the lady again but she did on one occasion tell me her brother liked to try on her clothes when they were younger so it was not new to her.

Most men will not admit it, but they were guilty of trying on mom’s or a sister’s clothes or lipstick at one point.

 

[dogboy]

When I was a little kid, I loved dressing up in girl clothes. My mom had an old duffle bag of her old clothes and she let me play dress up with them. I can't remember if I suggested this or my mom did, but one Halloween I went out as a girl. My mom had gotten a cute dress, stockings, and even a wig and she did my makeup. We went from door to door and all the neighbors pretended to not know it was me. I was in little girl heaven.

 

[Angelapinks]

Most men will not admit it, but they were guilty of trying on mom’s or a sister’s clothes or lipstick at one point.

I mostly tried my sisters clothes because we were close in age and size but I do remember once when I was 10 or 11, my mum left her Playtex rubber girdle on the bed and I touched it and fell in love with the feel and tightness after I put it on. I only did this once and got out of it quickly but I wanted one of my own so badly. It would be another 8 or 10 years until I found the same style on Clearance Sale at Sears. I ordered two and still have them today but they are discoloured and one is a little stiff in places where the rubber aged. I wish I had ordered more.

 

[Diaper44]

Most men will not admit it, but they were guilty of trying on mom’s or a sister’s clothes or lipstick at one point.

That’s exactly what I did as a kid

 

[LonelyFOX]

My girlfriend is who started it all!!!.
At the beginning she wasn't interested in men because she told me that she was lesbian.
Then one day she asked me to try on her stiletto sandals. Then one day I went to her house and she asked me to try on her dresses.
And then she told me that I looked so tall and so sexy in her dress.

 

[drippydrawers]

wearing nail polish

 

[Jorelaxed]

wearing womens colorful slouch socks!

 

[Ali123]

That’s exactly what I did as a kid

I often wonder how many men have tried on women’s clothes at some time.

When I talk to guys I know about it they’re often quite dismissive of their experiences, like “oh it was only for a fancy dress party”, or “a group of us dressed as nuns for Hallowe’en “

Among other cross dressers I’m friends with they’ve often started by trying on their Mum’s knickers when she was out, or a sister’s skirt.

 

[rbm]

I often wonder how many men have tried on women’s clothes at some time.

When I talk to guys I know about it they’re often quite dismissive of their experiences, like “oh it was only for a fancy dress party”, or “a group of us dressed as nuns for Hallowe’en “

Among other cross dressers I’m friends with they’ve often started by trying on their Mum’s knickers when she was out, or a sister’s skirt.

I would bet alll most all cd,s start like that , Idid and then the wifes until I started buying my own after she bought me my first bra ndpantie set, a teddie and a makeup kit

 

[Diaperedforsuresince17]

Mine started back in HS I’d wear my cousin’s bar, panties and pantyhose under my clothes, sometimes I’d wear woman’s pants in a size 6 and would still have to wear a belt. Going out fully dressed started just after HS while I was in Baumholder I was very passable back then. Today I do it just a kink events

 

[drippydrawers]

 

[Jorelaxed]

View attachment 89641

nice colors!