Regrets?

[laurie103]

In college, I was living alone, dating a bisexual girl who went as a "transvestite" for Halloween. She wanted me to wear the same outfit as her, and I refused, even though I really wanted to. I feel like I missed a huge opportunity to come out. I was too cool at the time, refused to give into who I am. Anyone else have times they could've made leaps and didn't?

[MonicaPVD]

Regrets, I've had a few...
But then again, too few to mention...
I did what I had to do...
I saw it through, without exemption.

[Karren H]

I wish I had kept a date with a local girl in college.... would have learned how to polka! I regret not taking my mother up on her offer to dress me up as a girl for Halloween when i was like 8...

I also regret that our High School Letterman Society, the year before i was eligible (9th grade)... dropped the hazing ritual where you had to dress up like a girl for a day a during school. That last year they did it (I was in 8th) one of the smaller guys got dressed by his mother and sister and you would have sworn her was born a girl. So cute! Come to think about it, looking back.. I's say that he had crossdressed before. just looked way to comfortable! But I missed out on that!!!

Ohhhh and I regret not grabbing my grandmother's awesome girdle collection when she passed away. Think my mother and sister threw them out or gave them to goodwill. Many fond memories of those girdles.... when grandma was at work, and I was supposed to be painting her house... or weeding the garden! lol


probably a few dozen more regrets....

[JenniferR771]

Oh! Me too, my mother offered to dress me up as a girl for Halloween at my school for the day. I refused partly fearing the kids at school would have teased me.
And my mother might discover how much I liked it.
And then in college, my roommate may have figured it out when we shared an apartment.

[Lana Mae]

I regret being naive about all this! If I had understood at a younger age, it might have been different, but...then what about my wife and two children? I guess it was better the way it happened!!! OK, no regrets! Hugs Lana Mae

[Melissa in SE Tn]

Monica is a frank Sinatra fan

[kayegirl]

Not sure if it's a regret as much as I wonder what if.
In my teenage years I had a girlfriend who was, shall we say, a bit of a tomboy. In the 2 years of our relationship, I never once saw her wearing a dress or skirt, although more than once she suggested that I might like to. And yes more than once I did take up her offer. We first met at a climbing club, and even after we had split up, continued to see each other at the club . The thing was that she became increasingly masculine in both appearance and mannerisms,. I lost all contact wits her and the club when I moved away for work, but I do often wonder how things would have been had we stayed together. I should emphasis that I am not unhappy with how my life has panned out since, nor do I particularly regret our parting company, but as I said at the beginning, I do wonder water if.

[SaraLin]

H-m-m-mm. Here's one, but I'm not so sure it's as much of a regret as it is a "what if"

At one point I became close with a lesbian friend, and she knew about my dressing desires - but I never found the opportunity to get my girl on with her around (lots of complicated reasons).
I do sometimes wonder how she would have felt and if she would have dated me - as Sara.
She's long gone (out of state). I've moved on and am happily married now. But every now and then I still wonder if anything could have come of it.

[Angela Marie]

No. No regrets really. I grew up in the 60's when dressing, transgender (if it was even called that) was so out of not only the mainstream but everyday conversation. I married, have two beautiful children, grandchildren, and a wife (second one who is open minded about my dressing). We never know what life would have been like if circumstances were different. If you are a good person, father, husband, grandfather, etc. the positives immensely outweigh any regrets.

[Teresa]

Laurie,
I guess you could ask do you know anyone who doesn't have regrets ? It's what makes life interesting and frustrating at times .

[Amelia_Rose]

My biggest regret is that I did not come out to my wife earlier in our relationship. I've felt more shame over the secret keeping than the secret itself. We've had a long talk about it and she says she forgives me (for not telling her sooner), but finding that forgiveness in myself will take time I guess. I cannot ask for a more loving and supportive partner in life, and the fact that I did not tell her sooner feels like a betrayal of trust and a slap in the face for someone I trust and value so completely.

[Krisi]

I'm sure everyone has regrets, but if we had done the things we regret, our lives might have changed and we might not have the people and things in our lives that we have today.

I switched careers on a whim; I saw an ad in the newspaper (remember those), interviewed and got the job. I met a guy at my new job, started playing music with his band on weekends and met my wife at a place we were playing.

I suppose that's the opposite of "regret", but it's an example of how life changing a simple decision can be.

[BobbiKay]

A few decades ago I was friends with a female coworker. I wanted more from the relationship, but she insisted on keeping it in the friend zone.
In addition to the other attractions, we were of similar builds, so we could have shared a closet.
Yes, I really thought of that.

[Karren H]

we were of similar builds, so we could have shared a closet.
Yes, I really thought of that.

I am guilty of choosing girlfriends in high school and college who were the same size as me so I could borrow their clothes!!

[Jemima Stephens]

I had a Girlfriend who would dress me up and we went for a walk around her village a couple of times which I found exhilerating. She then tried to persuade me to go to the pub in the next town to meet her friends whilst dressed, but I bottled it, both from a being found out by family point of view, but also I was in the Air Force at the time and that would have been construed as Homosexual behaviour which was against the rules at the time.

I do wonder what would have happened if I had taken that extra step 33 years ago!

[Deborah G]

Some years back, I had a long term girlfriend who I am 1000% positive would have no issue with my dressing. In fact, when we were on a trip to Niagara Falls, and I had forgot my underwear, she offered me her panties to wear! Later, on another occasion, she offered to apply make-up on me and then we could go out as girlfriends. Since we were about the same size, she said I could borrow her clothes, and she did not hesitate to try on some of mine now and then. Sigh, I would have none of it as I wanted to be the "macho man". After about a year, she lost interest in me and moved on, despite my attempts to rekindle any flame. Thinking back now, the last 30 years may have been completely different for me if I said "OK" to anything she proposed. Where is the "Way-Back" machine when you need it?

[josie_S]

At least two ex-gfs asked me if they could put mascara on my lashes (i'm lucky that my lashes are full and long) and paint my toenails. Like Deborah, I was too caught up in being macho and pretended like that was the last thing I could ever want...sigh!

Another involves a very good looking French man that was hitting on me at a bar on one of my early outings. I was so nervous and felt so self-conscious that I figured there was no way he was interested in me. I also think--despite the heels, french tip manicure, hoop earrings, cleavage, perfume, make up and LBD--that I was also still hoping, praying, that I could be the macho man LOL

[NancySue]

Of course, but, I too, did it My Way.

[sweetdreams]

The wife and I divorced for a 3 year period and then married each other again. In that 3 year gap we both had relationships with other people. I've shared this story with you before. The girl I was living with during that gap in the marriage actually got turned on by my dressing. Nothing was too much for her. If I got dressed up (MIAD), within about 30 minutes she would grab me by the hand and lead me into the bedroom for you know what. My wardrobe at the time was limited and she would share her clothes with me including making suggestions like which of her blouses would go with my skirt. I also caught her wearing a pair of my panties one time, hmmm?. We split up for other reasons (certainly not my dressing). My imagination runs wild thinking about what it might look like if I had stayed with her. She would have supported pretty much anything I wanted and would have likely initiated things I hadn't even thought of.

[SherriePall]

I don't think I have any regrets. At least not along the line of dressing. I do have a few "phew, that was close" situations where if I had done this or that, I would immediately have regretted doing so.

[Christina89]

My 2 biggest regrets were not being honest with my mother when she first caught me with a stash of some of her clothes. And my second was not telling my stepmother. Her and I had a bond that was similar to that which my mother and I had. I feel that if I told both of them then I could have been a little more open when who I am.

[Sunny_with_a_chance]

I'd say my biggest regret is not exploring this side of myself earlier. I grew up in a really normative male culture with an emphasis on sports and typical masculine bravado stuff.

I'd always wanted to dress, try makeup, even do things like the school play, but shied away from it all because it wasn't 'normal'.

While I am sad I didn't follow my heart earlier, I am glad to be who I am now. I think I did what I had to back then to thrive in that environment. Maybe I would've been happier, but maybe I wouldn't have too. Who's to say!

[c2candice]

Two regrets that are related:

1. I didn’t have the courage at a young age to explore this side of myself when I was single, and had more of an androgynous figure.

2. I didn’t reveal this to my current wife right away in our relationship.

[BLUE ORCHID]

Hi Laurie :hugs:, I regret waiting 72 years to get my ears pierced, All those years of clip-ons,

>>>>>Orchid**O:daydreaming:O**

[Tabitha_Lynn]

Like Christina, I wish I had been honest with my mother when I was caught as a teen rather than pushing further into the closet.

I love my life, today and wouldn't want to give up my family, but often wonder what it would be like if I had been honest with myself and others way back then.

[Cheryl T]

Of course...
There were moments I wish I had handled differently, but it is what it is.
Can't live in the past. I can only enjoy the present and hope for the future.

[CarlaWestin]

I was in a parking lot and behind me was the entire Ringling Brother's Circus train on a straight siding track.
I could see the entire train from end to end. I had my phone but I didn't take a panoramic picture. I didn't take any picture.
That moment will never happen again.

[Star01]

Probably my biggest regret was after dieting down to around 150# and growing my hair out at 53 in 2004. My wife confronted me and demanded that she did not want to see or know about my dressing. This coincided with a rush of guilt, purging, and quitting smoking resulting in a 40# weight gain since that time. I don?t regret quitting smoking but I regret not being able to control the weight gain. I regret my hair thinning out on top and adding the additional hassle of having to wear a wig as well.

[Leelou]

This has been a very interesting and sometimes super fun thread so far. Thanks for starting it, Laurie.

I loved hearing about the stories of moms offering to dress their boys for Halloween and those that did. I wasn't so lucky. I was already a slightly effeminate pretty boy and I don't think mom wanted to put her thumb on the scale in that area.

I also enjoyed the stories of women offering to participate in dressing, nails, etc. and some of us not ready yet. That's also my contribution of regret. I was out to a girlfriend in college. It was all lingerie at the time for me, and therefore with us. She was into to it, and it was a turn on for her and she was buying me stuff. She offered that we should completely dress me and go out. I turned her down and regret it. I just couldn't wrap my head around it--that it would be possible. If I knew then what I know now, I would have known it was totally possible.

It's a regret, but not a deep regret. I love that I came out to a woman so early in life and she was so totally accepting. It set the precedent for me to come out to other women later in life.

[candykowal]

For me, regrets come and go...life continues to move on.
Most of my regrets were in trusting people to accept me as Candice but ended up being used for money, favor, or to belittle.
I regret wasteful spending on drugs and booze, in my music industry circles, causing me to not being able to afford SRS before I turned 30.
I regret purging all my pictures from film from my teen years in high school and college while I was presenting as a girl full time.
I had so many good memories from friends who only knew me as a girl, and a friend.
I only have a few old pictures today, from those friends who found me on social media and sent me their copies.
Returning to presenting as a girl when I can do it without hurting anyone, I have no regrets as they are all behind me.
I've learned my place here in this life and I am happy where I landed.
I am blessed I can still reminisce about my youth and those memories, lessons, and tasks I experienced while embracing my feminine side. :daydreaming: