crossdressing timeline.

[Brenda Freeman]

We all have a story of how it started, fears, barriers, triumphs, and how far we have gone.
My crossdresser timeline. There is so much more I could fill in as every step required courage and luckily support from others.
When very young I remember looking at the Christmas catalogs lingerie and dress sections and dreamed of wearing girl clothes.

11 or 12 tried on my mom's girdle and nylons and was hooked. loved how they looked and felt. Did this when time allowed also added the slip.

12 or 13 my Mom wanted to dress me as a girl for Halloween as I could not decide what to be. I did not take her up on the offer which I regret to this day. Would have loved to know what she had in mind but I was afraid.

Kind of went in hiding until college tried on a few panties but purged quickly.

Around 35and married I bought bikini panties and told my wife they were more comfortable. She was fine with it and even said I looked good in them. loved that.

40's bought a dress or two and pantyhose but purged quickly. I traveled for business and would wear a dress and hosiery at night when on the road.

My 50th year I had a crisis anxiety I could not hide it any more had to deal with it. It is a long story involving many steps and support form some wonderful people but the short story at 50 I bought a bra forms a wig had a make up transformation and a make up lesson and saw for the first time Brenda in the mirror. I could not believe it I kind of looked good. Hooked no turning back. Signed up for a tgirl event. Told my wife (another long story). But we worked it out, Happy ending to this day ( it took some time). Went to the event with my wife's blessing. First time seeing Tgirls, over a 100, all supportive and sharing of their stories. This was a life changing event, I was not alone.

When I had time alone at home I would dress up fully make up wig the works and spend time, tried different out fits took photos for good memories. I loved these care free times and improved on my make up and styles every time was fun. Girl time my escape from my daily work life. Great memories.

60's Go out occasionally to meet friends. Have gone to DLV in Las years the last 3 years, A tgirl event, and have gone back to that first event I attended, Esprit every year since my first in 2005. Spending a few days just being Brenda and meeting with others sharing our common interests has been wonderful and helps me appreciate that I can be and express who I am without guilt or judgement! And I am helping some of the new girls with support.

Hope to continue and help others where I can.
THATS my Timeline in Brief.

[Beverley Sims]

Three or four, was the baby for the girls next door.

Five or six played lots of dressup with them.

Seven and eight, regular sleepovers and a birthday party dressed as a girl.

Later years the odd foray into going out with the girls visiting their relatives dressed as a friend.

Eighteen to twenty five, met girls and shared a house, I was their bodyguard as I was the only boy.

Often dressed as a girl.

Married after that and things have progressed positively ever since.

[Rachelish]

Hi Brenda

I think that will be a familiar timeline to many. It certainly fits my experience: at around age 10 finding female items of clothing that had been stored away at home and being unable to resist trying them on - and I did the catalogue thing too! Later on, around 18, I recall finding some discarded lace panties at the launderette and sneaking them back to my room to try on, then getting terrified of discovery and ditching them soon after. Following that, a hiatus until much later which included marriage and kids and now, in my 50s, reaching a similar crisis point. Mine is yet to be resolved, though I have come to terms with it myself and am content with who I am, having progressed to dressing fully and achieving a complete look that I'm happy with. My SO has seen that I've switched to some very feminine (male) underwear and have been wearing leggings around the house for a few months now with barely a raised eyebrow, but anything further needs the talk

From here, who knows.

Rachel

[MonicaPVD]

Somewhere between 8 and 10 I started wearing my older sister's clothes. My parents found out and that stopped for a while. I dressed on and off throughout my teen years, privately at home. During college I dressed often and went out in public. Later I got married and stopped dressing although I never stopped thinking about it. Now, in my early 40s, I started dressing again and have been going out in public regularly.

[StephanieH]

I don't think mine has been a timeline - it's kinda' always been there. Enjoyed wearing girls clothes and undies when I was a child, still do. Didn't start buying my own until after I was fifteen and could go shopping on my own, but I'm fifty-four now, and the shopping sprees come and go, just as they have since I was a teenager. I don't go out dressed very much at all - the problem of being in a small town. Whenever I get to nearby New Orleans, I dress and can go everywhere in the Quarter and nobody cares. There are so many guys dressed down there it's never been an issue.

[Jenny22]

Monica, you omitted in your last sentence whether or not your wife knows and is on board with you. Can you clear up same for us?

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Brenda, I do remember you from DLV, and the large Oregon bunch. DLV was the most amazing experience, ever!

[April T]

Forget my first pair of panties but remember telling my girlfriend at 17 that I wanted to wear garter belt and stocking. She dressed me up and brought over a friend from her work where she worked part time. SHe watched as I dressed up and then she introduced me to her friend. He was the first guy that I orally serviced. So sorry I broke up with her!

[Felicia M]

It began at four with mother's stockings and pantyhose and her blessing.

Found the panties and bra's when I hit puberty.

In my teens I tried all the goodies. Makeup, dresses, heels.

My twenties and thirties were very sporadic and usually only happened between relationships except for one where I would sometimes dress in my SO's clothes (I know....big no no).

I came out of another long term relationship in my late thirties and found myself in a new city living completely on my own in my own town-home. It was truly a golden opportunity and one that I now regret. I began to purchase my own clothes. I even went and purchased a pretty extensive makeup kit. I explored Felicia for a few months during this time but slowly my conditioning to want a heterosexual relationship took over. This was the early 2000’s when internet dating was exploding so that began to take over my life until I met someone and got married.

Divorced and had some really dark years after.

I met my latest SO in my mid forties and we have a lovely relationship with a child. We are not married and are very open minded and best of friends. I began to dress again in early 2017 and since it has essentially taken over my life. She does not know but I know I will have to come out to her. I do believe that she will be understanding but it is still a daunting thought process on how to cross that bridge.

[CDYoga]

Around 16, I started using make up from the drug store to help cover up pimples.

Around 18, accidentally bought a pair of women's pants at the thrift store and wasn't made that they were women's pants for about 6 months when my girlfriend at the time saw them on the ground. I wore them at least 2x a week, no one really said anything.

Sometime after I started dating a guy who noticed I wore make up and the women's jeans. Turns out he wore a lot of women's clothes and make up as well. I started wearing a lot more women's clothing after this, but this was a great relationship... it was like I finally met someone who was like me.

There wasn't much of a change until I was around 30 when I asked my partner (currently my wife) if she would be ok with me wearing Yoga pants around the house. She has no problem with it as long as I didn't wear them outside the house.

Between that time and now I started wearing more make up and more feminine attire full time, but I really don't make a big deal about it. No one has every really said anything to me about it and I brought it up with my wife and she told me that she didn't know most of my pants were women's pants. I am not sure if people actually notice I am wearing women's clothing most of the time... I really stick to pants and cardigans.

Recently I have started wearing non-natural colored lipstick, my wife said she was still ok with it as long as I don't wear it outside the house. I really don't try to look like a woman though, I really just like the clothing a lot. That could be a reason some people don't notice what I am wearing, not sure.

[tammy1]

Sounds like your wife is accepting of your enjoyment of feminine clothing and makeup. ENJOY!