At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

I did a search to see if a thread like this was done and didn't find one or maybe I just don't know how to do a full blown search.

Anyway, please advise at what age you were when you first started to cross dress and how you felt. Did you continue or stop for awhile? What articles of clothing/makeup did you start with? Who's clothing was it?

I started at 5 years old with my mothers underclothes (slips, nylons, panties, shoes) and eventually at about 8-10 years old was also getting into her dresses and bathing suits. They have pictures of me with her lip stick on (that was the time they caught me). I stopped for short periods of time and started again throughout my life up to about 4 years ago when I started to dress in something pretty much full time. I came out to my wife about three + years ago.

Right now at work I am wearing and typically do wear everyday, thigh high holdups, a bra, a butterfly necklace under my shirt, and perfume (lightly applied when at work and normally when at home). I sleep in a nightgown most nights. My wife and I have the same nightgowns just in different sizes. So one could say, we dress alike. :heehee: FUN FUN FUN!!!

Ash :doll:

I realised at 5 that I wanted to be a girl, but can't remember crossdressing until I was 6 or 7. I swapped clothes with my cousin - bet she can't remember that day as well as I! :happy:

I started dressing when I was about 8 or 9. My
mother and grandmother kept their old clothes in
a closet off the bathroom. It was a treasure trove
of 40s and 50s style dresses. When I was in high
school my mother worked so I was alone when I came
home so I could do all my homework in dresses and
skirts. After I left home, I always envied and wanted
to be a woman but I didn't CD until I was about 40.
Something happened then and since then crossdressing
has become stronger and stronger.

I am a bit embarrassed to admit that I resisted the urge to crossdress until way into my mid or late 30's....some 20 years ago. I was married and had been for at least 15 years. I came out to my wife and told her I wanted to explore these feelings and she was accepting. I wore her panties and nylons to begin with and then of course, I had to have my own.

Today I have the whole wardrobe from wigs to shoes, bras & panties to swinsuits...way too many feminine clothes, but fortunately we wear close to the same size.....(except shoes)...and so we share a lot of clothes. We enjoy shopping together, sharing and wearing our clothes.:D

So....even tho a late bloomer.... I am making up for it and enjoying both sides of my persona....:D

i realised i should of been a girl when i was 7 and thats when i started cross-dressing the 1st item i wore was my sisters school uniform and when i put it on i felt fantastic as i was wearing the clothes i knew i should be wearing

another late bloomer... mid to late thirties. Not exactly sure what triggered it, but I think I got tired of buying my wife nice lingerie that she never wore, so decided to wear it myself!

I also wanted to be a girl at a young age. I didn't start crossdressing until i was 11/12 when my parents started letting me stay home alone.

I too did a search for this and couldn't find anything. I'm sure it has been asked many, many times before. I tried it on just the word "age" and not a single post came up. Oh well, so much for that.

I think that I started a birth. My older sister told me that I wore her baby clothes when I was born for at least the first 6 months. They were hoping for a girl all along so they never bought any boys clothes. Of course I don't remember that. I do remember noticing at about 3 or 4 how much nicer my sister's clothes were than mine.

Men's clothing is sooo DRAB! Why wear plain cotton underwear when silk or nylon feels sooo good. Why wear plain brown, blue, or black pants when they can have flowers printed on them. I could go on and on about how better looking the clothes are, but I'm sure that you know all too well.
:hugs:

I had three older female cousins that liked to make me their dollie sometimes at around age 2....
as i got older the teasing from two older boy cousins got pretty severe.
so, around age 5 I was too fast for the girls to catch me!
i took a lil break from girls clothes for about a year then around age 6 I had a golden opportunity!
The middle cousin was a very active ballerina and i got to stay the nite in her room while she was away for some school function :D

well i saw a pretty light purple ballet dress/tutu hanging there and i couldnt resist!

I became a panty theif and really into ballet stuffs...
it wasnt till around age 12 when my cousin busted me!

I started early about when I was 10-11, I really wanted to be my sister, her clothes were a poor second best. I never ever tried my mom's clothes, thinking back, I sure was naive.

i started when i was 14 i think mostly my sisters stuff. then quit for a long time .started again at about 30 and stopped and started for ten years now i dress once in a while but only undies as my wife would not agree to anything so i can hide the panties.

I first started dressing when I was around 10-12 as I am now 23, I believe it all started when I started hanging around my cousin who was 1 age younger then I was. She looked so pretty when she was dressed up and I wanted to look just like her. We had the same color hair and body type with the exception of me being 3 inches taller.

So I started to stay over her house more often and hang out with her and her friends and playing different games with them(one i can remember is Girl Talk, it came with a pink phone and index cards telling you different things to do). She wasnt that organized though to my benefit lol, she would leave her panties and thongs all over the house and at night when everyone would fall asleep I would either take some in a different room or the bathroom and try them on.

Ever since then I've been doing it on and off. Sometimes i'll stop for awhile and then I will see something that will trigger it like a cute pair of panties or dress and I will suddenly get the urge to start doing it again. Now that I've had a girlfriend for the last 2 years, clothes are alot easier to come by . She doesnt know how much I am into it yet, but I started out wearing her panties a few nights and she was all right with it and it kind of turned her on, so now she doesnt mind me wearing them at all whenever I want(usually when we go to sleep). Im slowly starting to let her in on the rest but well see how it goes.

I started when I was 10-11. Things have progressed on and off over the next few decades. Times of skipping but always returning to dressing. As I said before, my opportunities now are very limited and often there is the risk of being found out.

Lacelover

My mom put me in the firt pair of panties that I can remeber when I was 3, I think that is what triggered it all for me. I think she was trying to "punish me" for haveing accidents, but little did she know, How great they felt for me.:devil: That is a whole nother story. Then when I was six I took and put one of my moms slipd under my pants and went to school, Well I had got in to trouble that day, and well let me say my parents were in to the old fashion whoop ass punishment back then, so I had to beg my dad not make me drop my trousers so he could spank me, WHEW! that was close. When my mom and dad divorced whenI was 12, I had more time to dress in my moms clothes. I first started out with her bathing suits and as I got older started to wher more of her lingerie and dresses. I remember around 13 or 14, I would push the envelope and I would dress up and walk around our house when it would get dark. My mom was out at the pool halls, so I had really no worries to get couaght, wow that was a rush:heehee:

I was visiting a cousin for the summer in another state and shared the same room as her. I always wanted to go to bed wearing her pantyhose but my uncle would'nt allow. Not much really happened until the teen years and being home alone. Once I moved out and was older then I got my own items and would dress in the privacy of my home. I only had my first makeover last year and what a blast it was!! I can't believe my pics and what I look like in male mode. Truly mind screwing! Anyway, that's it.

I first tried stuff on at the age of 8 or so but I did not start "crossdressing" until I was about 12. At that time it was used as a shield for me because I wasnt a popular kid in school so when I was home I dressed to "get away" from my problems. As I did this more and more I felt more and more comfortable doing this and it become more of something I loved to do for fun and simply because it felt great.

Tried on pettycoat at 6, dressed in a leotard to play with sister and next door neighbor girl at age 9 or so.

Dee

i knew i wanted to be a girl at age 5 to 6 but dressing did not start until 7 or 8 stockings or pantyhose .. or when i got a chance my older sister she had some cool outfits back then

started dressing when i was about 8.

Haven't stopped since then!:love:

Like you I started about age 5 or maybe earlier with undergarments.I started dressing fully 2 or 3 years later and have never stopped since.Makeup came a little later, maybe 11 0r 12.:hugs:Angela.:bunny::bunny::bunny::GE:

I started at about 7 or 8 with petticoats and nylons and it just developed from there.

Tried on pantyhose when I was about 12 - 13.
I didn't start to fully crossdress (including makeup and wig) until last year when I turned 37.

I started around 11 or 12, with my mom's tights, then moved on to skirts, dresses, bras and swimsuits until I outgrew everything. I started dressing again, mainly just with pantyhose and tights, when I got an apartment with a bedroom of my own.

:2c: [SIZE="3"]This has turned up on the forum a lot, so I'd like to see it made into a sticky, if possible. I think a lot of us are curious on this issue, as are our spouses.

Once again, for me, realized I had girlish tendencies when very young, probably five or six, but didn't "dress" until I won the boy's beauty pageant in the fourth grade. That was the day I realized how much I really liked how the "other half" lives.

Take care![/SIZE] :D

i started dressing in my sisters clothes starting with her panties when i was 12