Crossdressing Regrets

[Brenda's Friend]

Ladies, here is an occasion to write about those missed opportunities to crossdress. I defiantly had several of those moments where I could have dressed or it just didn’t work out the way that I dreamed about. Until I bought my own clothes, I stewed about those lost moments for years.

My 8th grade French class was going to do a performance of Cinderella for the French Club. One day the girls who had the Evil Step-Sister parts were absent. My friend John, who was the class clown, got me to fill in that day. Needless to say we were hilarious, and everyone in the class wanted us to do the parts. Girls in the class bought us dresses and jewelry for the performance. For me a secret crossdresser, we didn’t have wigs or shoes or bras or makeup. Oh how I wished I could dress all the way. But my desire to dress was a deep secret and I was too shy to even tell my mother about the performance. I’m sure that if I had asked, she could have provided the missing elements. Oh, at 13 I could have really looked like a girl.

[tamarav]

Rather than focusing my energy on what could have been, I prefer to look forward and expand my opportunities.

Not trying to downplay missed opportunities, but they are history and you are history in the making. Go for the gold and do your best now, you only have the future to make changes.

Shoulda, coulda, woulda. That is what my Marine son tells me when I speak of things I didn't do..... Move forward and enjoy life.

Your way too happy sis,

Tami

[docrobbysherry]

I just hate my old, stringy looking arms while dressed now. If I had dressed back when I was young, they were much more fem looking. And I could have been SUCH a young hottie! How often do I think about that? Well, other than rite now, I haven't!

The rest of the time, I'm concetrating on how I can look better in my pics TOMORROW!:daydreaming:

I'll think more about my yesterdays when I've REALLY old!:heehee:

[Toni_Lynn]

Regrets are a weird thing. Yes, i do regret having missed some great opportunities to crossdress in the past, but then when I look at where I am now, I always say my life is pretty good and where I am is exactly where I am supposed to be.

I guess that needs some explanation. I regret not crossdressing more as a teen, especially after I got a job and started making some money. It was the 70s and fashions then were so mod and cool! I regret not standing up to my mum when she found my training bras and panties when I was age 13. If I could go back to any one time in my life, I go back to that time for just one day, and it would be an explosion of crossdressing and shopping :)

That said, I am happy with what I did do; underdressing at school, my clandestine use of the girls lavatory etc.

Ah, and then there was when a certain advertising sales girl, who was called Bugsy, came into the radio station that I was working at one Sunday. We were the only two people in the studios, and she called me come into the closet where we kept all the old records. It was based that, based on the fact that she had discover som crossdressing fiction books in the rash dumpster near my car and some other telltale signs (bra straps?), that she asked 'are you a crossdressers?' Duh, I denied EVERYTHING! BTW -- the reason she called Bugsy was a reference to a certain cartoon bunny and because she was, er, like a rabbit in terms of the reproductive act.

I regret getting spooked after I was read the first time I went out. I was in Transpitt at the time, and the icy stare that the girl at the food court gave me was enough to cause me to break all ties with group, stay locked in my hotel room for the next 16 hours, and purge everything.

I regret that I didn't persue the girl who dressed as a guy (my one big turn-on) while I dressed as Madonna at the young adults Halloween party at St Cyril's church in Houston Texas. We danced together all night and it was great. We exchanged phone numbers, and then my drinking got in the way and I was never able to follow through, since the booze took over.

Same goes for the fact that I was totally on my own, yet wasted 2 1/2 years drinking instead of crossdressing.

That said, I also don't regret that because when I got sober, I came to appreciate the girl that I am, and realise that I might not be were I am today, I those years, and everything before it not molded and formed me into who I am today! My reward for my sacrifices is that today I can crossdress whenever I want to, be the girl within, can share this with my wonderful wife, and have learned to live and make my choices in life with the sound of Edith Piaf singing 'Non, je ne regrette rien' in my heart!

Huggles

Toni-Lynn

[Deborah Jane]

I guess this pretty much somes it up

sEbgB6X6S5c

[Roberta Marie]

I agree that we need to look forward. But looking back helps us to understand who we are and how we got this far. That helps to figure out were we want to go and how to get there. Problems, though, can arise when we dwell to much on the past, on the would-a's, should-a's, could-a's to much. But if we don't look back every once in a while, we are destined to repeat the same mistakes over and over. Perhaps talking about our regrets here will help the younger girls not make the same mistakes we made.

I didn't come out to my wife until we had been married for almost 30 years. That's not my regret, becasue one of the things that she said in the conversations that followed my coming out was that if I had told her this earlier in our marriage, she probably could not have handled it. My regret is that I just started shavinig my legs this past February. The first time I wore nylons over bare legs, I made the comment to my wife, "I wish I could have done this when I had young, cute legs." So, I regret not being able to shave my legs at a younger age, but I don't think I would do it any different if I had a life do-ever. Because then I would have had to tell my wife earlier, she would have left me, I wouldn't have the wonderful kids and great life that I have now. All in all, I'm happy with the trade-off.

Grace,
Bobbi

[Sarah...]

Regrets...

Pah!

...I did it my way.

In other words, I reckon I made my choices for my reasons at the time, and now I am where I am. And I'm enjoying it.:daydreaming:

Sarah...

[Karren H]

No regrets here.......

[gennee]

None here.

Gennee


:)

[Jessicaparkson]

My only regret is that I don't have any of my friends or family that accept or even tolerate me...

[trannie T]

The only regret I have is that sometimes I dwell upon the thought of things I could have done.

[Tasha McIntyre]

Only regret is that I didn't tell the wife a decade ago (when she was my g/f)

[Veronica 1]

My only regret is that I let my redneck upbringing brainwash me into not accepting who I was until I was 50.

[Samantha Kelsey]

The first time my older brother saw me as a woman he said, "well kid all I can say is you should have done this fifteen years ago". He didn't realize that I was doing it fifteen years ago but in the closet. My biggest regret now is that I didn't come out fifteen years ago.

[CD Susan]

I guess this pretty much somes it up

sEbgB6X6S5c

What a beautiful post Debbs, thanks for posting it!

[KellyCD]

My only regret is that I spent the last 10 years of my life trying to make other women happy by locking up the woman inside me.

[Amy Hepker]

My only regret is that I did not come out many years earlier

[Melora]

This "might" sound kinda bad or Selfish.. But..
2 things..
A) Sometimes marring my wife, because I might be a whole differernt person now. (Though I may actually be dead now if not for her).
B) Not telling her Before we got married..
Sooo...
TO ALL NEWBIES....
PLEASE Please Tell her before you wed her! There are soo many stories out there like mine!
Honesty is essential..

[Phyliss]

I guess I could say that I wish I had started sooner. However having said that, I wouldn't have had the maturity at the time and would have most likely made a mess of it all.
"Growing" up and gaining experience and self confidence had to be the basic building block for me long before I put on my first pair of undies.

I wouldn't call it a regret but there are times when I've planned a day for myself and some customer will call me and I have to go satisfy their needs.

Of all the nerve of some people, don't they understand "it's all about me". :rolleyes:

[Lilith Moon]

Same as most here....I'm not young any more. I had killer looks (and lots of long hair) 30 years ago but was soooo closeted despite having plenty of opportunities to dress.

[Kate Simmons]

There were a lot of times during my life when I "coulda, shoulda, woulda". The important thing is that I am now in touch with myself and my feelings which is what it is mostly about for myself. I have no regrets. Due to a recent death in my family it may come about in the near future that I may not be my femme self as much or possibly not at all. The clothes are the least of it really and family is more important to me. In any case, I've pretty much made my "mark" in the TG community and have nothing more to prove. Still, I reserve the right to look nice if and when I feel like it as it is part of who I am.:)

[morgan51]

not letting Morgan blossom a lot sooner in life I wasted a lot of time. making up for it now . Morgan

[MarinaTwelve200]

I shoulda done what ALL my friends were doing on Halloween in the 60's when we went trick or treating---Dress as "a girl" at age 12 -14 I had the perfect body for it. And it was THE costume atthe time for boys in my age group.---(I had been CDing since age 12---but in secret) Perhaps I felt it "hit too close to home" and I went out with my friends dressed as a "Goul" rather than a "girl" instead.

Lookig back, I KNOW I could have done it without ridicule, I had the perfect excuse, (All my friends were doing it) and no one, even my parents would have faulted me for it---Indeed, I feel that my mother would have JUMPED at the chance to doll me up.---it would have been lotsa fun and a great memory.

But alas, it wasn't to be.

[darla_g]

Ladies, here is an occasion to write about those missed opportunities to crossdress. I defiantly had several of those moments where I could have dressed or it just didn’t work out the way that I dreamed about. Until I bought my own clothes, I stewed about those lost moments for years.

My 8th grade French class was going to do a performance of Cinderella for the French Club. One day the girls who had the Evil Step-Sister parts were absent. My friend John, who was the class clown, got me to fill in that day. Needless to say we were hilarious, and everyone in the class wanted us to do the parts. Girls in the class bought us dresses and jewelry for the performance. For me a secret crossdresser, we didn’t have wigs or shoes or bras or makeup. Oh how I wished I could dress all the way. But my desire to dress was a deep secret and I was too shy to even tell my mother about the performance. I’m sure that if I had asked, she could have provided the missing elements. Oh, at 13 I could have really looked like a girl.

That story just sounds so adorable. I can imagine myself in that scenario.