You may recognise some of these.

[Helen_Highwater]

The 7 ages of crossdressing for the more mature crossdresser

1. Too young to know.
Fascination with mom?s or sisters under garments. If you?re of a certain age it?s stockings with a seam, Playtex 18 hour girdles and industrial strength bras.

2. Old enough to know it?s something not to tell your dad.
Still the same as 1 but now things ?stir? when trying things on.

3. Into work, off to college.
Now you might have the money to buy things. Older members will not have the benefit of the internet so shopping was restricted to ?Buying it as a Christmas present? and as most still lived at home with mom?s who scoured your bedroom for dirty socks to wash, finding a place to hide things was a challenge. The chances you knew of any other CD?ers was rare. Hormones coming under control.

4. Grown up stuff; Marriage and children.
If you kept it a secret then you were now tempted by wardrobes and drawers full of nice things. Size differences could prove problematic. Hiding your stash still an issue. If you came clean at the start then you had someone to share it with but still thinking it was just you. In the closet, you now needed to be doubly careful having inquisitive rug rats about the house. Out to the wife, doubly doubly careful as ?The kids can?t know!?

5. Mid-life
To the kids you?re just a Taxi service and you never know when they?ll come home until they go off to uni. Your wardrobe has grown and your choice of clothes is getting better. Those out and empty nester's now have a level of freedom back. The internet has arrived and you might be considering going out as you now know others are out there. After dark drives tempt you. By now you?ve realised it?s not going away.

6. Retirement beckons.
So if you?re still in the closet, you have the time but not the opportunity. Out to your SO; by now you?re either living the dream or spending most of your time looking after grandchildren.

7. The mind is willing, it?s the hips and the knees that aren?t.
Those killer heels haven?t seen the light of day for a good while. You?re dressing like that nice old lady who lived a few doors down who sadly passed away some years ago. Some will be looking back at all those pictures of them out on the town enfemme. Others will be thinking, ?I wish I?d listened to Helen when she said you don?t want to get to the end and start thinking, I wish I?d?..?.

[jacques]

hello Helen,
probably most of us follow a similar path.
mine was -
- why can't I wear tights like Robin Hood
- why are boy's clothes so boring?
- teenage hormones messing with my imagination
- college - too many distractions to cross dress
- grown up stuff - shared secret with wife
- kids leave home - I can find my true self and get a bigger wardrobe
- retirement beckons - "enjoy yourself, it's later than you think"
- old age beckons - how could I cross dress in a care home?
stay healthy,
luv J

[Robertacd]

Pretty much my story. I went as far as #5 and said "Kids are grown up and the house is paid for. Now it's MY turn!", and never looked back.

[Karren H]

My 1 was more like... mother, sister, aunt, grandmother, step mother, step sister, sisters friends, girl next door, female borders we let a room to (one of them ended up being my 10th grade English teacher)..... think I missed a few..... I was a prolific borrower.

[Beverley Sims]

I remember my three was too many distractions but they encouraged me to dress and go out with them dress shopping on Saturday Mornings in those days.

A night out with the girls at a Drive In theatre or such like was always a blast. :-)

[Vikky]

Helen. It all seems very familiar. Vikky

[GracieRose]

It all sounds familiar.
It is so great to know that it is not just you, after going through most of your life thinking that is was.

[Liz Jones]

Hi,
Yep as i have said before --"as the age goes up the heels go down" well for most of us ! Do wonder looking at the photo's girls dressed just how far they walk in the 5/6"heels that you see!
Liz

[Lana Mae]

Oh, the memories!

1. Why did the little girl throw that dress over her head? Yes, her name was Lana!
I scanned all the clotheslines for women's "delicates"!
2. Panties only! Then some more things, oh my! Pantygirdle, stockings, slip, was there more?
3. No time! USAF and then college took me away from this aspect of my life but not to stay!!!
4. Wife said no women's clothes! There will be only one woman in this marriage! Two wonderful kids! Sneaking panties!
5. Totally agree! Enter the Net!! I now know what it is all about! Wife passed away and son left home to get married! Daughter still with me! Both accepting when I came out to them! Daytime drive! Transformation! Wig, and make up!!
6. Well, semi-retired! Totally out to everyone! Living 24/7/365! I am a pre-op transwoman and my name is Lana Mae! It has been changed most everywhere!
7. I am the elderly lady next door! I have no regrets!
Thanks, Helen!
Hugs Lana Mae

[MeshelleCD]

I have progressed to #5, but closing in on #6 quickly.

[Stephanie47]

Chuckle, chuckle. I had to look up the birthday of the internet; January 1, 1983. I would have been 36 years old. Of course that does not mean there was internet access for the masses. No real home computers. No access to information. The Kinsey Report was held behind the librarian's desk at the local library. I still haven't seen a copy of it.

I have to throw in military service at #3. There was zero opportunity for personal space and privacy. In my military (army) it was life in a bay in a barracks. Personal space was a foot locker. No private bathrooms. During my two years of military service I never experienced the pull of any cross dressing. I think it is due to raging male hormones; especially in Viet Nam. Clothes consisted of whatever you were wearing and an extra pair of socks. When you use the term drab, it was really really drab.

[SharonDenise]

Cute! Being in my 70's, I recognize many of those stages. I was fortunate with my wife.. I came out to her before we were married and she accepted and supported my crossdressing. It was secret between the two of us until she died after 40 years of marriage. I am out to my daughters and many others now but will never be comfortable with letting everyone know that I cross dress. I haven't been on here for some time so I think i need to go to the Introductory section to let others know of the progress I have made.

[Sandi Beech]

Helen,
Your post is making me feel old : )
#1 did get me thinking about something. Although I never thought about wearing women?s clothing when I was young, I do recall being fascinated by the women?s section of the huge Sears catalog we used to get, especially the bra section. Maybe it was a subliminal thing. For those old enough to remember the catalog, I would be willing to bet I was not the only one studying the playtex bra section.

Sandi

[SaraLin]

1. Too young to know.
More like too young to understand? At first, I thought I was a girl, but was told, "no, you're a boy". So - I wanted someone to fix it!

2. Old enough to know it?s something not to tell your dad.
With an angry, bitter father - I learned VERY early to not give him any information about anything, if I could help it. I extended that cloak of shame / secrecy to the world at large.

3. Into work, off to college.
This was more like off to the Army and into an early marriage. I tried to keep my "otherness" buried during this period. For the most part I succeeded, but wife found me out.

4. Grown up stuff; Marriage and children.
Married at 19 - with built in family (she already had a son).
My first timid steps out of the closet came during this era, with very limited success.

5. Mid-life
With two failed marriages I had some time to explore me. Ultimately, It's a long story, but I opted out of my true desire (full transition) for a number of reasons, and I ended up in my third -and final- marriage which is semi-DADT.

6. Retirement beckons.
The only real change here is that I have more time to loaf around the house in my nightie (which is OK, per the rules).


7. The mind is willing, it?s the hips and the knees that aren?t.
I'm getting close, but I'm not there yet...

[Helen_Highwater]

the huge Sears catalog we used to get,

Sandi


Sandi,

It was Littlewoods and Kays in the UK. You couldn't call them "light" reading.

[KymG]

That takes me back, id forgotten about those.
Showing my age now...

[LydiaL]

Oh my how shopping online for direct delivery today has sort of come full circle. Mom always got the Sears and Montgomery Wards catalogs, occasionally a Penny's I think. Anyway, living in the rural US Midwest in the 50's, or so, nearly all our family shopping was by mail order.

Hmm, thinking back, I must admit that I too did not dwell on the boy's/young men's clothing sections. Sneak peaks at the lingerie time to time!

[sometimes_miss]

Mine was:
At about 3, mom was dressing me in my sister's 'hand me downs'. I remember wearing some type of dress when playing in the dirt in the backyard.
Then at 4, jealous of all the attention my mom gave my sister when getting her ready for school, I put on one of my sister's dresses and proudly walked in where mom was doing up my sister's hair, and said, 'I'm ready to go to school to!'. Of course mom changed me back to boy clothes when we went to walk my sister to school. When we came home, she asked me, 'Do you really want to wear that?' but in a tone which indicated that the only correct answer was no, so that's what I said. Even so, mom sewed blue and red thread stripes into my sister's old underwear, to emulate dad's Fruit of the Loom briefs, but I knew what they were; but wore them anyway, since I had no choice.
At 7, molested and told that I was really supposed to be a girl, dressed in his younger sister's clothes for 'the deed', over time I started to wonder why god made this mistake? And I tried to learn how to be a girl, by scavenging my sister's old clothes that mom stored in the attic. AFAIK, no one in the family knew I was doing this, and I got a lot of practice wearing and pretending that I really was a girl. But I knew that boys who were sissies got beaten up, so I never wore anything outside or anywhere that anyone else could see me, other than when 'he' wanted me dressed that way.
At 14, I wondered if I was gay. But that didn't make sense, as though I liked girl clothing and it felt 'right', I had no attraction to boys or girl activities. Molester gone, so I'm not just dressing up for myself because it feels like what I'm supposed to be. Patiently waiting for god to fix me; but no matter how much I prayed, that never happened.
Started reading my sister's psychology books, trying to figure out why I'm so screwed up. Learn about transsexuals, but that doesn't quite fit, either. But it's as close as I would come for years to understand why I wanted to dress and be a girl, even though it still didn't all fit together right.
20's, learned how to ballroom and disco dance, and suddenly had more female attention than I knew what to do with. Crossdressing and gender bending out of my mind, as I'm so involved with dating women.
I thought that either I had outgrown, or 'beaten' it. Didn't crossdress for about 10 years, and neither did I hav any gender identity issues other than an occasional fleeting admiration for pretty female stuff when I saw it either on a woman, or in a picture somewhere. But the thoughts didn't last.
As middle age approached, stress (loss of job, 60% reduction in salary, working full time and school full time) allowed the crossdressing genie out of the bottle and the desire came back with a vengeance. Left a slip out and wife saw it, that was the beginning of the end of my marriage. Wife said while we were in therapy, that had she known before we got married, she never would have married me. She blackmails me for all our assets or she'll disclose to my family, friends, and at work that I'm a crossdresser. I give her what she wants. AFAIK, she held up her end of the bargain.
Post divorce, I put up personal ads online, identical other than one mentions that I crossdress, and the other does not. The first gets lots of interest from women; the other NONE. That would continue for the next 20 years. I discover that guys being feminine is a huge turn off to most all women; and, the few who are okay with it, don't want anyone to know, because women derive some of their marital status by how good a 'catch' they made when choosing a husband, and crossdressers are pretty much at the bottom of the status list. So they wouldn't want anyone to know even if they DID meet, date and marry a guy who crossdresses. So there's no way to find those women.
I realize that the few women who are smart enough and secure in themselves enough to date a crossdresser, have much better options than myself.
I'm careful to never let anything connect me with crossdressing. I get a private postal box where I have all my girl clothes delivered to. I never go out even underdressed. I accidentally once forgot to remove my nail polish, and got to work with it still on, then desperately trying every solvent in my car to get it off so I could go into work without any teltale polish remaining. That only happened once, and I will never forget it.
Now retired, I dress up as a woman every day while at home. I consider my male clothing my 'man uniform' which I have to wear to do any chores or activities outside my home. Not unlike the uniform I had to wear to go to work all those years.
So for the rest of my life, I crossdress alone, at home, and dream of what might have been, had my life been different somehow.
And come across this: https://www.youtube.com/watch?v=YRjhts_p1H8

And it makes me wonder all over again.

[SharonDenise]

You hit the nail on the head when you tell your next possible long term relationship that you cross dress. I feel the need to be honest with the women that i date and eventually confess that I cross dress. There goes the relationship. So glad that my wife put up with me.

[Star01]

1. Too young to know - would sit and watch my mother get ready and apply makeup. It was fascinating but I didn't know why.

2. Don't tell your dad - I had my first experience getting into clothing in the attic at 13 and thought it was exciting but I didn't understand why and would never tell my WWII vet father.

3. Off to college - in my case it was anchors away and trying to stay alive on the flight deck of a carrier. No women on board ship in those days and no thoughts of dressing in that environment.

4. Marriage and children - I didn't understand what caused the dressing episodes. Four kids, family breadwinner in a one income family. Conditioned to be masculine, still didn't understand what came over me years ago and thought of it as a kink that I outgrew.

5. Mid life - nest emptied out, left a cult situation after 25 years at 48 and it was the first time in my life I was free to think about my crossdressing. Fog hit, wife confronted me and demanded DADT about sixteen to eighteen years ago. She did not want to see or know about it.

6. Retirement beacons - retired two years ago, started therapy a year ago. I need to revisit the talk but still have not found the right moment.

7. The mind is willing - I gained 50# and purged as a result of DADT and the ensuing depression. Today marks a week with a new treadmill. Star wants to come back in a big way and is working towards that goal. I have plenty of aches and pains but I still think I have a few good years left. I'm more of a flats than high heel girl so no worries about knees and hips. Spiked heels are the stuff of girlie mags and are of no practical use on snow and ice or in dusty fields.

Some say that us older ones should have come out to our SO when we met. How could I have told her when I did not understand myself? It would be nice if everybody knew what they are at five years old and could have planned our lives accordingly but that is not the case with everyone. Some of us are slow to realize what we are and do not understand the obvious until later in life. By that time we have had families and are established in life when it finally becomes obvious to us what we are.

[alwayshave]

Helen, Seems you have correctly defined the arc of a crossdressing life.

[MysteryWoman]

What a great analysis!

I'd add something to number 7: Getting into pantyhose almost requires me to hire a dresser. Thank God for thigh highs.

[GretchenM]

Love it, Helen. You have really captured the life cycle of people like us and who are at our advanced age. And to all those who described their sequence, thank you. It goes to show there is a common pattern that exists within us and it is different from what the cisgender people experience. Probably the best evidence to support a conclusion that this gender and crossdressing thing is grounded in some very real processes. I suspect the early stages may be a bit different for those who are in their 20's and 30's, but I would bet good money that the fundamentals are still very similar even though some of the details are different.

I am deep into Stage 7. Sexy is pretty meaningless. Presentable as a senior is about as far as I can go without looking like an unsuccessful Cougar.

[Claire M]

For me, stages 1 and 2 were a single brief stage starting when i was 13 and first wonsdered how it would feel to wear my sisters panties, then bra, then skirt then ..... It only lasted about 3 years and I only fully dressed 3 or 4 times.

Stage 3 lasted almost 12 years for me, during which I dont remember even thinking about womens clothes ... other than how to get them off the girl I was with. Glad to hear I wasnt the only one who seriously thought that Stage 2 was just a phase I went through as a kid but nothing I had any futher interest in. Unfortunately my stage 3 didn't end until several years after I married. When I finally came out to my wife (Stage4) she was upset i hadnt told her before we married but I truly did not feel I would ever do it again in those days.

In Stage 5, dressing saved my life. I had major bypass surgery about the time the kids left the nest. That gave me more freedom and a desire to dress much more. Since the cutest outfits always seemed to be one size smaller I really pushed my exercise routine helping my full recovery from my heart issues.... thenl COVID came along :(

Im just starting Stage 6. It will take some adjustment as my wife and I spend so much more time together. In a DADT relationship that doesn't leave too much opportunity so I need to get creative or find a way to ease the DADT situation.....

Well see how stage 7 goes ....

[SaraLin]

One thought I'd like to add to #1

For me, the initial fascination wasn't with the underthings. I fell in love with the dresses, the pretty long hair, etc.
The "undies" were more just because they were what belonged underneath.
Of course, I did start really young (I think it was always there!)

[Polly R]

Hi Helen, almost reached 7 as you know. Almost became 7 when my right knee started playing up again but got called into hospital a few months ago (during lockdown!) to have the half knee replaced with a full one. Back into 3" heels now, yeh! Missing Llandudno, be good to meet up at Unique again when this pandemic is finally over...

[kellyanne]

The 7 ages of crossdressing for the more mature crossdresser

1. Too young to know.
Fascination with mom?s or sisters under garments. If you?re of a certain age it?s stockings with a seam, Playtex 18 hour girdles and industrial strength bras.

For unknown reasons stared at the bra , panty and girdle sections of catalogs

2. Old enough to know it?s something not to tell your dad.
Still the same as 1 but now things ?stir? when trying things on.

Went to the dryer and my moms bathing suits wa sin there - knew I HAD to put it on and suddenlt felt " me " and a true sense freedom of joy that I stil feel en femme.

3. Into work, off to college.
Now you might have the money to buy things. Older members will not have the benefit of the internet so shopping was restricted to ?Buying it as a Christmas present? and as most still lived at home with mom?s who scoured your bedroom for dirty socks to wash, finding a place to hide things was a challenge. The chances you knew of any other CD?ers was rare. Hormones coming under control.

Did scads of in person shopping, had some bad experiences but was overall treated politely. I was in a lingerie section when a friend and his classmates walked by and thought who knows what.

4. Grown up stuff; Marriage and children.
If you kept it a secret then you were now tempted by wardrobes and drawers full of nice things. Size differences could prove problematic. Hiding your stash still an issue. If you came clean at the start then you had someone to share it with but still thinking it was just you. In the closet, you now needed to be doubly careful having inquisitive rug rats about the house. Out to the wife, doubly doubly careful as ?The kids can?t know!?

Never married fpr various reasons but being a CD contributed to the decision.

5. Mid-life
To the kids you?re just a Taxi service and you never know when they?ll come home until they go off to uni. Your wardrobe has grown and your choice of clothes is getting better. Those out and empty nester's now have a level of freedom back. The internet has arrived and you might be considering going out as you now know others are out there. After dark drives tempt you. By now you?ve realised it?s not going away.

Yes, there comes a point where the sane girls says as you say " this is me and it's not going away" Purging is futile, " we can only be who we are as a wise philosopher said"

6. Retirement beckons.
So if you?re still in the closet, you have the time but not the opportunity. Out to your SO; by now you?re either living the dream or spending most of your time looking after grandchildren.

^^^^
Here now, thinking of doing more CD activities, meeting others and group functions

7. The mind is willing, it?s the hips and the knees that aren?t.
Those killer heels haven?t seen the light of day for a good while. You?re dressing like that nice old lady who lived a few doors down who sadly passed away some years ago. Some will be looking back at all those pictures of them out on the town enfemme. Others will be thinking, ?I wish I?d listened to Helen when she said you don?t want to get to the end and start thinking, I wish I?d?..?.

Like another girl, I guess I think of what will be found when I pass on, how it will affect my legacy.

Onward and upward.