Start dressing later in life?

[ChristiesGurl]

I was just wondering how many of you didn't start dressing or have thoughts of dressing until later in life, maybe after you saw another CD'er out or? if so, what was the thing that made you start thinking about it?

[Lexine]

I started dressing this year, when I was still 30. The reason why I started it is somewhat a sad one.

My confidence was sapped after 4 years of being engaged to someone who I thought was the love of my life. Sadly, things didn't work out and I felt really horrible. I needed a way to regain a lot of my confidence back in an efficient quick manner. As it turns out, my friend was going to have her birthday at Disneyland and invited people to dress up either as Goths or Pirates there and celebrate with her. I didn't want to have to do neither, so I thought of the next best thing: crossdressing! I thought that whatever I need to do to gain my confidence back, it'd have to be something that I'd possibly have absolutely no control over other than trying to look as best as I possibly can.

In the end, I had so much fun that what was going to be a one day affair turned into something that's now permanently part of my life. True, there have been many instances in my life, in retrospect, that led me to this, but I believe that things happen for a reason and I'm really happy... even overjoyed... that I found this side of me.

[PretzelGirl]

I am pretty much a late bloomer as my dressing really came out in my low to mid 40's. But when I was young, I did try some things on and immediately took them off out of guilt. And then I stopped. What got me going? A little bit of playing around with my wife went from one piece of clothing at a time; to a little more dressed up; to completely dressed up; to long hair, shaving off the moustache, and make-up. So I believe it was in me all along, but wasn't strong enough until later and needed a trigger to get going.

[Crissy Kay]

I"m another one. It was on halloween ten or so years ago, I finally bought a french maid outfit that I had always wanted!!! With the internet, like a lot of us I was able to buy stuff I had only dreamed about before.

[Loveday]

Yup, I started late also. The doctor suggested I start wearing pantyhose to help push up the blood from my lower portion to my chest in my early forties. After watching my father die at home in front of me 10 years later I took up the doctors suggestion. Later when summer came I realized I could not hide them if I wore shorts. So I went and bought a skirt to drive in. Since then it has been a new me..her..whatever. I do often wonder if it is all the meds I take (over 20 per day), but then again I seem so much happier now.

[docrobbysherry]

I was over 50 when I started. And, I had NEVER even thot about trying on ladies things before then! It was only ONE pair of abandoned jeans and I simply wondered if I could fit into them! I did, but they were VERY TITE! I LIKED THAT!

This CDing is REALLY a slippery slope, isn't it? Lol!

[Cari]

Dressed my whole life - started more seriously in my late 30's got my own wardrobe went to support groups in my 40's.

I think I reached the point where it became really apparent that it wasnt a phase I was going to outgrow. So I started to learn about it and dressing more often.

BTW - If anyone thinks that if they indulge and get dressed to the nines it will satisfy their curiosity and they will be done; didnt work for me :-).

[Raychel]

I have been crossdressing all my life, But up until about 6 years ago, it was just lingerie, Now it is the full wardrobe. Life sure is more fun now that I am older.

[RADER]

Started early in life. off and on through the middle of my life; now that I am
retired, have more time and lots of interest. I guess just to soon old,
and to late smart. Rader

[Janine cd]

I started dressing early in life but never realized how satisfying it is to dress fully until I reached 50.

[denisecdfl]

I fooled around a bit off and on when I was younger, but never owned anything of my own. I discovered the internet and was hooked. Had my first makeover at age 60, and my new hobby was begun. Now I have my own things, although I still enjoy taking photos in my wife's clothes. She knows, but I don't dress in front of her. My going out just started a couple years ago, and is only on my solo trips to Vegas.

[suchacutie]

I never had any interest until some items in my wife's lingerie drawer looked like they would fit me and we laughed as I tried them on. Her comment was to compliment me on my legs over and over, so I said maybe I should finish it with stockings and heels. She agreed. I went off to the internet (knowing absolutely nothing!!!) and bought some silver/black stockings and 6" platform heels.

A couple of months later we were in a hotel room by ourselves and she said, "well...am I going to see you dressed?" I said, "ok" and off I went to the bathroom. When I came out I admit I was nervous. I had the heels (that I could barely walk in), stockings, garter skirt, and a black silky top...that was it. no forms, no wig, no makeup..nothing!

My wife took one look at me and I almost panicked, but then she said, "Your legs are better than Tina Turner's!" and then...changing our lives she said, "We HAVE to buy you a dress".

That did it...within a week we had named my feminine side, ordered breast forms and started looking at wigs...had a separate e-mail address, and joined this site. The rest, as they say, is history.

I was 55, married for 34 years.

Clearly my feminine self was there all the time, we just didn't identify it til 5 years ago. The drive to know who she is, this Tina, is overwhelming!

tina

[Jay Cee]

I started "officially" crossdressing a few months ago (in my earlyish mid 40's) on a regular basis. Anything prior to that was more a series of occasional lingerie tryouts. It's probably only through the substantial emotional support of my SO that I am exploring this. Otherwise, I doubt I would know how good it feels to have a hairless body, and wearing nighties to bed every night.

[JohnH]

I guess I started dressing gradually - I converted some of my jeans into home-made denim skirts and noticed they really felt so much more comfortable than pants. That was during the last spring. And then I ordered some denim skirts that wore instead of shorts for this past summer. I also got some women's sandals - up to 4 inch stiletto sandals. Then I went through clothing my ex-wife left me - I came up with 11 dresses that fit me and a number of shoes.

I really pity the normal "sheeple" man who has to live within the narrow constraints of masculine wear - I am so much happier with my expanded wardrobe options. I also have natural B cup breasts - I don't feel miserable about my "moobs" and contemplating breast reduction. In fact I would like breast augmentation to be done so that I can have D cup breasts.

By the way, I am 58 years of age.

[daphne_pynk]

being 29 and just coming to terms with the idea that its ok to be like this, i do feel like i missed out earlier on in life but i'm sure i'm making for lost time just being on this site!

[Ann-Marie]

I wore some womans panties for about 5 years ( am now 58), started seriously dressing a few months ago.
I enjoy the tight feel of female garments and enjoy the sexy look of clothes that woman wear. Lucky my wife indulges my new passion and takes the photographs and helps with the shopping.

[StarrOfDelite]

The internet. I was dressed as a little girl by my three-years older than me first cousins when I was a little kid, and looking back know that it excited me sexually even at that age. However, I grew up in a family that prized athletic glory, leadership, and a lot of other WASPY virtues, and sublimated everything. I knew nothing about crossdressing or transgenderism for most of my life, except for seeing ads in the Entertainment section of the newspaper about Drag Queen and Female Impersonator night club acts (which I never attended). When I was in my early forties, in the mid/late 90's, my wife was out with some of her girlfriends, and I was on the early internet, and just browsing around I came across several transvestite websites. These were mostly of the Professional ******* type, but many were just personal websites. I was transfixed, and sexually excited. My marriage was going badly at the time, and I made a conscious decision that this was a world I wanted to explore. Eventually I hooked up with a CD whom I met on Alt. We had multiple intimate meetings, and the more I was with her, the more I wanted to be like her. Eventually, I persuaded her to play the masculine part, but she didn't like that very much, and eventually we broke up. I continued to dress in private, and acquired my stash of wigs, shoes, dresses, and lingerie. That was probably around 1998 or so. I am normally rather dare-devilish, but it took me another couple of years before I was able to go out in public to Trans-friendly gay bars, and a bit more time after that before I started dating men. Got divorced in the interim, but that had little or nothing to do with crossdressing or bi-sexuality. I am still totally enraptured by the beautiful androgyny of my Sisters, and have DVD's full of pictures downloaded from the internet of clothed and nude crossdressers. I sometimes wonder on 'might-have-beens' if I'd started earlier, but don't dwell on it.

[AlannahNorth]

By the time I was 8 I knew I was attracted to feminine clothing, but it wasn't a big deal. Borrowed the occasional pair of panties up through my teens, and when I got married, maybe put on a pair of panties twice, that's it. Serious interest began when I realized my marriage was going downhill, the times when my wife was away. Then when she left (I was in my mid forties) I bought some lingerie of my own, purged once or twice and kept coming back. About 10 years ago I began to buy my own feminine clothes and considered I may have a real interest in cross dressing. Have done little in the past 5 years but recently have moved and now have my own place. Finally!

So I really got going in my mid 40's, had to delay the 'hobby' but can now indulge.

The only 'so called' female item anyone has seen me openly wearing is a sarong, I occasionally get to some summer festivals and such where they are not uncommon for men. Also, I wear them about the house indoors. I guess if you call earrings feminine (they aren't here) then yes, since the mid 70's.

I've only met another cross dresser once (to have spoken with) and that was at a store in downtown Toronto - Wildside. Guess I need to get out more...

[Georgia Rose]

I started dressing at around age 59. Never had a pie4ce of female clothing on before then. My wife was away for around 10 weeks to help family & I somehow started on sleepwear and one thing led to another. I now have a full rnage of make-up, skirts, dresses, shoes, lingerie etc. Dont have forms or a wig though and have decided against these as after discussing it with my wife (I confessed when she came home) she got a bit scared about me going that far. I'm working on it though. I'm now 62 and dress regularly.

[erickka]

I dabbled in dressing since I was about 6 or 7, but I guess I could be considered a late bloomer mainly because I really didn't get serious about it until my late 30's.

[Maria_1969]

I wore my sisters red tights under my pants to school in the first grade, I was 6 (I can remember the whole day) and I was hooked.... I occasionally would try on other things in my teens but it did not do much for me, I had only a pantyhose and tights fetish. Now, I am 41 and wow.... everything has changed and I want to be female as much as I want to be male now. I do not do my face yet as my SO and I are going to go at a slow pace to ensure Maria develops slowly and cautiously for both of us.

Even though my testosterone was tested this past summer and is at 465, which is good for my age, it still may have dropped from where it was and as we get older our estrogen will naturally increase some and that combo may have something to do with it for many of us older ones. Also, my nipples have become more sensitive which shows somethign has changed somewhere for me physicially. Also, my sex drive has gone down and my appreciation and respect for women has gone up.

I look very much forward to getting a wig and doing my makeup but my SO and I just want to pace it. I am considered a good looking man so I do hope I am also a good looking woman. I dream of being Maria when we shop together…. :-)

I own bras, dresses, many skirts and shoes and a massive pantyhose and tights collection…. Besides the hosiery, 90% of the rest was purchased over the last 2 months.

Maria

[Tammy V]

I started putting on mom's things and makeup when I was very young, but when I moved out of the house for college I rarely had any more opportunites to do that. When I was 40 I got the bright idea I could actually go out and buy my own things and its been a steady progression since then. Sure, all those years I was not dressing (unless I could find a drawer with some panites or something) I was thinking about it, and always had a strong desire to "see what I would look like as a female", but never had any assistance and I eventually got up the courage to do it.

[AllieSF]

I started 3 years ago, and let's just say that I was over 39, errrr, 49, oh OK, 50ish, errr, you get the picture! I may had unread and un-acted upon hints and clues that I may like to dress as a women all though out my life, but, being the slow learner that I am it took me a long time to get here. What really triggered it (the straw the broke the camel's back??) was the negative side effects of prostate removal for cancer in 2005. You could say that one thing led to another and then another and lo and behold Allie was born in 2007. An interesting aspect, and for me a benefit, of starting later in life is that I never suffered from everything that so many other suffered throughout their lives and continue to suffer. I am at the stage in life that I finally realize that it may not last forever, so I am in the "enjoy it now because tomorrow it may be too late" mode. I have inconveniences caused by my new found passion, but the benefits and fun far outweigh the negatives.

[Colo Deb]

I was in my mid 40's when I started. I wore dresses when playing as a 7-8 year old, but didn't really start until I discovered the internet forums about 15 years ago. I never would have purchased an item of woman's clothes until I reading your stories about your shopping trips. Started with pantyhose, panties, bra, dresses, tops, wigs--where will it stop?

[Karen 812]

I started when I was 53. Only went out dressed at night because I had a mustach and my then wife liked it. If I shaved it off, she would get suspicious and asked why. Later, when I got divorced, and on my own, I started dressing more often. I didnt go out during the day for some time untill the apartment manager found out and wanted to see me dressed. Later I found my current SO working at an adult store that catered to crossdressers. She applied my makeup properly for the first time, and now after several years, we go everywhere whith me emfemme. She even buys cloths for me.

[Mackenzie]

For many years I put on some of my wife's things in secret; her bras and panties. I was always afraid to tell her my desires. I am now in my early 50's, and about 8 years ago I started buying a few pieces of lingerie just to wear to bed. At first my wife was appalled. Well, fast forward. My wife is so kind to me and supportive. I am able to dress now just about anytime I would like. We have a teen at home so I have to be careful. For me, there was a snowball effect. At first, it was simple items to sleep in. Then I wanted to do my nails, put on makeup, get forms, femme clothing, and fully dress. Often, I feel much more comfortable as Mackenzie than the male self. It is very enjoyable to "get in my wife's world" in this fashion.

It's interesting, that somehow when I am dressed, there are such feelings of femininity that I want to express myself more to my wife and be more open and vulnerable with her. She really enjoys the openness and communication.

Mackenzie

[Brenda Locke]

For myself i started dressing when i was in my 30's.
My living situation & job didn't really led itself to being able too dress until 2000.
Since Ive had my own place any all constraints are gone. So I can dress anytime that I wan't and It feels great to able to do so.

LoL Brenda

[Kaz]

Started I guess when I was going through puberty.. just experimenting... that is all it was at the time but it kept coming back. In those days there was no internet and limited access to any meaningful info, so I got on with my life, married, kids... every now and then things would "flair up" and I would either supress or momentarily indulge.

About 10 years ago I started realising this was never going to go away, and started exploring how to take this on board without destroying any people and relationships... and realised that it was not going to be easy... it would be very complicated...

So I started to actively accept "Kaz" as this part of me, and try to deal with that. And this has been my journey for the past few years. About 5 years ago I created a persona on the internet just to make this side of me "real"..

Finding this site was an amazing thing! In the past two years I have really got hold of this and posted pictures, got better with make-up, been out and about and generally grown and developed...

So I was a closet/in denial CD for most of my life... but now I know! And that brings fresh problems...

[the_me]

I'm really just starting to get serious at 27, and reading all these responses is really encouraging. Thanks to all you girls, I hope to make the most out of things while I still am fairly young!

[sandra-leigh]

I didn't realize I was a cross-dresser until I was 43. I had been "trying on" my wife's things (so I would know what looked good together so as to shop for her better) more and more often. I think possibly I had tried on a couple of skirts in a store a few times, as I knew by then how things should fit on me in order to fit on her. The idea that I wanted to wear those things was a revelation to me. I was out dressed in public within less than a month (first opportunity.) In retrospect, I had been leading up to that point for more than a decade.

[Barbara Dugan]

I started crossdressing a little over 3 years ago when I turned 38 thought I had it in my mind for about the past 10 years ..it got to a point that I couldn't suppress my gender and sexuality confusion ..It turn out to be a good thing because without it I think I wouldn't be alive

[Jennifer_G]

I didn't dress fully until I was 32ish (now 43) although I had worn the odd female thing before that. I'm not sure how I got here really, if someone had told me I be doing this years ago I'd have laughed. I remember seeing a CD in London at a tube station in the late 80's and wondering why anyone would want to do such a thing. Now I like to do the same. Life is strange and it proves that life is a journey and you never know where the road will lead.
p.s. I'm back here after yet another purge which lasted many months.

Jennifer

[Edwina]

I am another late bloomer I guess.
Apart from the occasional trying on of panties I did nothing till I retired at 61. I still thought that I would look silly in a bra. What was I thinking?:D My curiosity overcame me when a bought a bra for my wife (doing the laundry I noticed one of hers was a bit the worse for wear) Checked size and style and everything only to find that she had in the meantime bought new bras herself and in a larger size. :doh:
Well, long story short, I couldn't return it and so put it on to find it fitted me and I was hooked. (pardon the pun:heehee:) I was now on the slippery slope and my curiosity kept pushing me, one item at a time, until I am now as you see. :)
Now that my wife has also retired my dressing time is very limited but I do sometimes manage to be Edwina.

[Deanna B]

hi i have dressed all my life off and on . but 6months ago i told my wife of 9 year marriage.i am 43 . i started with 4or5 panties of my own then i went to slips and so on .
now i have 5 skirts 7 tops 3 jumps well you get the picture and i love being a female
:love:

[Jolene]

It feels good reading the posts here and finding out I am not alone in starting to dress later in life. I did try on my sister's things when I was young and remembering how nice it was and how I had always felt about women's clothing. About 5 years ago, I bought a package of women's undies and now at the age of 55 have a very nice wardrobe of female things for Jolene.
Why it took so long for me I do not know. :)

[annabellejorden]

I only really started dressing about 3 years ago.

I had gone on binges before, buying this or that and dressing, but then I would start feeling guilty about it.

After I moved to Portland, and had my own place again, I decided to buy a few things for my self, first a couple of bras, then some panites.
Only recently, I made the decision that when I am home, I wear feminine clothing.

and, I have noticed, I am happier since then.

[Cassandra90]

I always tried on my mom's clothes when I was a kid. just trying on bras and that. I also ended up with a 10 yr old little sister and she had play clothes that included dresses. I would come home after school and sometimes just couldn't avoid the feeling. Sometimes I feel that because I was born with something between my legs, that I was supposed to be a man. I've always been the more sensitive type. And, after my divorce abt 5 years ago, I decided to experiment with my desires and feelings. There's just something that feels right about crossdressing to me. I just have a hard time due to my current religion and feelings I have about religion in general. I'm almost 39 and have been buying and purging over the past three years. Definitely tired of purging! I guess this called purger's regret.

[Teri Ray]

I have been wearing womens things since I was very young (8 maybe 9) but never dressed fully til I was in my late 40's (kids gone and grown) Gosh why did I wait so long.

[Eryn]

I started dressing early in life but never realized how satisfying it is to dress fully until I reached 50.

My story too. Little things for decades, but more as the resources became available.

[juno]

I started after 40, but I liked girl things at least since age 4, and never felt bad about it. However, I have worn sexy men's underwear since my teens, the sort of stuff you can get at ABCunderwear.com. I always felt that men should wear lingerie, I just started out wearing stuff made for men.

I only started full dressing a year ago. I got a cheap clearance wig after Halloween and felt magic when I put it on. I had considered dressing as a female for Halloween before, but figured I was just not feminine enough to try. Once I saw myself in a wig, I was hooked.

[Cynthia Anne]

I didn't start til I was four years old! Does that count for later in life??

[Ozark]

nice post.

[Ozark]

For many years I put on some of my wife's things in secret; her bras and panties. I was always afraid to tell her my desires. I am now in my early 50's, and about 8 years ago I started buying a few pieces of lingerie just to wear to bed. At first my wife was appalled. Well, fast forward. My wife is so kind to me and supportive. I am able to dress now just about anytime I would like. We have a teen at home so I have to be careful. For me, there was a snowball effect. At first, it was simple items to sleep in. Then I wanted to do my nails, put on makeup, get forms, femme clothing, and fully dress. Often, I feel much more comfortable as Mackenzie than the male self. It is very enjoyable to "get in my wife's world" in this fashion.

It's interesting, that somehow when I am dressed, there are such feelings of femininity that I want to express myself more to my wife and be more open and vulnerable with her. She really enjoys the openness and communication.

Mackenzie

nice post.

[Alice B]

Exactly why I started I know not, but did not start until around 62. About to be 69 and dressing more and more.

[sissystephanie]

I am very different from most of you! My first crossdressing was when I was somewhere between 6 and 7 and I wore my sisters pink panties. I am now over 78 y/o, and except for my military service and a voluntary quitting period, I have been crossdressing ever since. My female wardrobe outnumbers my male clothing by at least 3 to 1! My lingerie far outnumbers my male underwear, probably by 10 to 1! I don't wnat to be a woman, but I sure do like to dress like one!!