Wish I'd found my femme side earlier

[somestimeskaren]

It's Saturday night and I'm dressed all made up and enjoying some Irish Whiskey.Sitting here enjoying my Karen time wishing I had realized I had a femme side when I was a good looking younger man.Growing up I was fascinated by female impersonators but never thought about wearing any of mom's clothes.She worked full time and we were home alone all the time but it never occurred to me to do it.I now wish I had . Once when I was 13 or 14 I did talk my younger sister into trying some of mom's different lipsticks on me(anyone remember the mini lipstick samples from Avon) but before we started the guys in the neighborhood wanted to play baseball so I went out to play.Nothing ever happened after that.In my late 20's I started wearing my wifes pantyhose without her knowledge eventually buying my own (remember LEGGS)then a pair of clunky heels.Soon after that I told my wife about wearing hose and heels and she was O.K. with it .We limited it to our sex play.After we split Karen emerged in all her glory and I love my life now, the only regret I have is not seeing how good I would have looked as a girl when I wasn't old and wrinkled. I am getting to the age now where I may have to go shopping for a gray wig .Nah. I think I look a lot younger as a woman than I do as my drab self,I'll stay a brunette.

[BLUE ORCHID]

Hi Karen, Getting older is mandatory, But going gray is optional.

I will be BLONDE as long as they keep making blonde hair die......

[Jasmine Mae]

I absolutely feel the same. I am 38. I'm Single and live alone. I have nearly unlimited opportunities to dress. i too Love my life right now! I often wish that I coul have enjoyed this inner peace with my cd-ing years ago!
I've dressed since I was very young. Never had the time/opportunities that I do now!
xoxo
- Jasmine

[Jennifer Michelle]

Not to brag about it. But I suppose I am fortunate in that I figured out I am a crossdresser at 25 so I still have a lot more opportunities to dress as a young-in.

[Jasmine Mae]

Jennifer!! Yes, You are very fortunate! Enjoy your youth! Enjoy your life!
... take a lot of photos!! Lol
xoxo
- Jasmine

[ronda]

Jennifer and Jasmine you are both lucky to have youth Jen I'm 30 years older then you and I'm having more fun now then I ever did and I have been dressing since I was very young I was in the closet till I was 55

[wanda66]

We are close in age and i know what you're saying, but this is now and you're found yourself, enjoy and live.
Today is a great day .......Tomorrow will be even better

[GretchenM]

Oh my, Karen. Those brand names you list bring back so many wonderful memories, including the tiny Avon lipstick samples. You made me smile real big. I have known about my feminine side, a rather large one I might add, since I was about 6. But my two sides fought like alley cats for 60 years. Sometimes She won, but most of the time He kept Her caged. It wasn't until a little over 4 years ago the He conceded or let her out or just got too tired to fight any more. Now they collaborate in a pleasant dance. Not that conflicts never happen anymore; they do. Just like friendships - they aren't always peaches and cream. I often wonder what would have happened if my mother had accepted my request, at the age of 8, to be a girl. Would I have outgrown the youthful femininity or would I be a transwoman now, maybe with a husband and some adopted kids? Either consequence would have been better than living a life hiding, denying, and suppressing the Her in me only to find she is really a very pleasant identity that the He in me should have allowed to be a party to the whole a long, long time ago.

[Abbey11]

I'm in my 40s and like you Karen have always been a fan but didn't find my own inner fem until the last 7 years or so, I'm having more fun and more content and happy now. When dressing and with makeup you look younger as a female which is an additional bonus

[Billy]

I think the older we get the more we are compelled to express ourselves as we want.

[GretchenM]

I think you are right Billy. And there is some pro literature out there that supports it. The theory (and it is only a theory) is that as hormones change late in life men and women tend to converge with respect to gender definition, that is, how feminine or masculine they are. Sometimes they even seem to cross over each other. Other times there isn't much difference. Thus, the theory part. But one thing is clear. There is a lot of shifting around that goes on after about 60 or 65 and, in general, people in that age feel they have earned the right to abandon the facades of younger life and just be who they are while not really caring that much about what others may think. It is certainly not pervasive, by any means, but it isn't rare either. A lot of times it is secretive with respect to exhibiting their feelings in public, but even that sometimes and often eventually falls by the way side to some degree. I guess the message is, we are all different and our differences should be celebrated and not constrained by the social boundaries of the younger folks (and even our own youth) which are often useful in the working world. But even that seems to be changing among the Millennials. To me, that is all the better. More freedom for all.

[docrobbysherry]

I think the older we get the more we are compelled to express ourselves as we want.

Well said, Billy! I'm over 70. But, Sherry's only about 20 because that's when I began dressing. As long as my health allows, I'll present Sherry in age appropriate looks. Maybe a bit over the 20 y/o she is, but no where near my age!
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[oh to be rachel]

I'd think I'd have a chance of passing as some sexy woman vs Tootsie or Mrs Doubtfire.

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Very very true!

[Becky Blue]

I hear you Karen, I often wonder what would have happened if I had a sister. From age 5 to 8 I regularly played pretend I was a girl games. I asked my mother to put a ribbon in my hair. Had their been young girls clothes in the house I can only imagine I would have been dressing at a very young age and who knows what could have happened.

Becky appeared at 40, now ages 50+ I lament the lost opportunity of dressing and going out in my 20s and 30s.

[Meghan4now]

So did you add a little water to the whiskey? Amazing how that makes a HUGE difference in Irish whiskey.

Yeah I get that. My life would probably be vastly different. But I also cherish the times in my life, so no sense in living in what if town. You can vist, just don't buy a house.

Jasmine made me laugh. 38. Seemed like a life time then, but I'm sure most of us will double that. Not picking on you Jasmine, but you got a lot of youth ahead of you. Make the best of it now

[Georgette_USA]

So did you add a little water to the whiskey? Amazing how that makes a HUGE difference in Irish whiskey.

I have heard that about Scotch from some television stories on the distilling industries.

[Jasmine Mae]

No worries Meghan! I do try to live n love life everyday to the fullest nowadays! Just wish I could have come to terms with all of this, been more accepting of myself long ago! Now my only dilemma is finding a reasonable anti-wrinkle cream for my "laugh lines" Lol

[sometimes_miss]

Once when I was 13 or 14 I did talk my younger sister into trying some of mom's different lipsticks on me<snip>
Nothing ever happened after that

But apparently, it did:

In my late 20's I started wearing my wifes pantyhose without her knowledge eventually buying my own (remember LEGGS)then a pair of clunky heels.Soon after that I told my wife about wearing hose and heels

FWIW: It's not a 'side'. It's all you. We don't have 'sides'.

[Stacey-J]

Count me in with Jennifer, I'm very glad to have discovered this part of me at 26. I'm also very lucky to have a supportive partner + live in a very progressive part of the world. (I don't mean to rub it in)

[Jaymees22]

I really didn't dress a lot until I was 67, but better late than never!!

[ElleStreet]

To those who started dressing later in life: Did you always want to crossdress but never had the opportunity until you were older or did the compulsion to crossdress not manifest until you were older? If it's the former, what stopped you from starting while younger?

I only just started dressing recently but I always knew I wanted to, even when I was pre-teen

[Lana Mae]

If I knew then what I know now! Pre-kindergarden was my first desire to wear a dress! Wore panties at various times of my life. Mostly a male with male life. No regrets! Great wife and kids! Realization only struck at 65! Maybe life would have been different but as I said no regrets! Hugs Lana Mae

[JocelynJames]

Elle,
I don't know about always- periodic urges is more like it. I feel like later on in life for most there comes a time when you as a person feel like you have to put your own needs and wants first . And a good portion of us were either in denial or didn't understand what we were. I had such long , Beautiful hair until 1997 -kind of like yours Elle. Hope that answers your Q

[Krisi]

Life is full of "what ifs". It's hard to separate the thought of being in our twenties in 2017 and the reality of life in our twenties. My twenties were the 1960s. There was no Internet or computers, no on-line CD stores, no silicone breast forms (as far as I know), no commercial hip and butt padding and probably not a lot of decent wigs. Even if all of this was around, we had no way of knowing about it or purchasing it.

In the 1960s, anybody out of the ordinary had to keep it well concealed. Walking down the street dressed as a woman would not have gone well. There's a really good chance that our wives would not have accepted it.

It would be great to be in my twenties in 2017 and be able to dress as a "hot chick", but we have to accept reality. I'm fortunate to look a bit younger than my actual age so I can dress without looking like a bag lady, but life is good and I can buy the body parts I need to look like a woman.

[Karen RHT]

Krisi makes a valid point. Many things were different when those of us who are now "seniors" were young. It's also true that the internet changed things dramatically.

One thing I've learned over the years, is that it's easy to look back and regret. Truth is we can't change the past, we can only do our best in the present and plan well for the future. I plan on enjoying whatever days I have left dressed as I please as much as possible.


Karen