View Full Version : That OMG moment!
AmyJordan
02-18-2025, 06:08 PM
Hi Girls
So as some of you know I am not your typical crossdresser, that being somebody who from an early age had a keen desire in wearing womens/ girls clothes whether their mothers, sisters or friends.
My sole but admittedly strong interest in women's fashion was simply in liking my girlfriends to look great and moreover as sexy as possible.
In fact my journey didn't start until my wife introduced it into our marriage, I therefore still struggle occasionally in accepting and embracing my situation fully, despite her demands being almost entirely 24/7 I still at times think back to my teenage years of macho pride and I feel embaressed even ashamed of how I am now dressed.
Don't get me wrong I wouldn't change my life in a million years, I am devoted to her and her to me and I am more than happy in making her happy.
So after my recent posts showing a Valentine's outfit I wore for my wife a very dear friend on this site messaged me and asked what I had done to my lips as they looked plumper, then BOOM! my OMG moment I then went into a discussion on how I had applied my lipstick as if we were just two girlfriends chatting about makeup.
Never would have imagined that coming a few years ago.
Have you girls ever had that OMG moment when you've done something you would never have imagined in your earlier life.
Amy x
JulieC
02-18-2025, 09:10 PM
Not quite a "BOOM" moment, but I did have a moment with my (then girlfriend, now wife) when I was educating her about higher end pantyhose. To myself "this is unreal; me teaching an amazing woman about pantyhose!"
Crissy 107
02-18-2025, 09:46 PM
Never would have imagined that coming a few years ago.
I think that sentiment is pretty common here, we help and support each other and accomplish things we thought could never happen but they do.
Sandi Beech
02-18-2025, 11:36 PM
When I was in my 20s, I was terrified of trying to dance in front of anyone anywhere in guy mode. It?s like I was embarrassed for anyone to see me. Now I will wear a wild outfit and get on a club dance platform by myself and be completely comfortable with it. The transformation is really quite remarkable. I cannot explain it. It does not compute, but somehow it?s tied into why I love it now, but hated it when I was young. Weird but true.
Sandi
docrobbysherry
02-19-2025, 01:38 AM
I think I get what u mean? I've had several mind blowing moments of self discovery, Amy. But, like u, I'm not your average CD!:devil:
Since no one here could relate to, or even understand them? I hesitate to post them.:straightface:
Marketa
02-19-2025, 03:21 AM
My biggest OMG moments were in regards to my eyes.
When I got eyeshadows and eyeliner right for the first time and then saw myself in a mirror, I realised I've got quite beautiful eyes actually.
And second one was even bigger, when I put on false eyelashes for the first time (with full make-up) I was totally taken aback, how beautiful and mesmerising my eyes are.
Helen_Highwater
02-19-2025, 04:27 AM
Perhaps the most common OMG moment for many of us is that time you see yourself in the mirror wearing a wig for the first time especially if you've been able to do your makeup first.
AmyJordan
02-19-2025, 06:03 AM
Sherry I don't think you should hesitate to post your experiences, yes your style may be more extreme than most but I don't think any of us are in a position to judge do you.
Amy x
Kris Burton
02-19-2025, 06:06 AM
I think my first photos were the real eye opener for me - when I realized this is really happening. Frightening and exhilarating at the same time!
Crissy 107
02-19-2025, 06:25 AM
My OMG moment was getting pedicures with different pretty colors and being treated like one of the girls by the nail tech and having idle chit chat with the other ladies
I’ve had a few of those moments, the latest was last week. My wife was out visiting friends, I got dressed in a maxi rib knit dress, bra & forms, black tights and flats, jewellery. Wife comes back, looks at me and says “I like that outfit on you” I say “thanks” then she adds “I like it when you get dressed up, it’s fun.”
alwayshave
02-19-2025, 07:59 AM
AmyJordan, when I went to my first CD/TG meetup and realized that there were all theses other girls like me.
Jamie Lynn
02-19-2025, 08:07 AM
Yes! Like some others, it was the first time I did my eyes and eyebrows! I am by no means good or accomplished at makeup, but that time elicited an audible gasp at how good I thought it looked and the possibilities!
April Rose
02-19-2025, 09:09 AM
When I was at the pharmacy picking up my wife, "K"'s medication and the tech asked me a question, and I said "I'll have to ask her" and he said, "Oh, I'm sorry, I thought you were K..."
Jillcder
02-19-2025, 09:39 AM
The one that sticks out in my mind is sitting in a hotel restaurant/bar sipping a glass of wine completely dressed in my cutest skirt and top having a conversation with my waitress as we chatted about cute hairstyles and her husband I remember thinking to myself wow we are talking like a couple ladies out for the evening.
Philippa Jane
02-19-2025, 10:36 AM
One of those moments comes to mind when I was sitting with a number of GG's and being completely accepted. I always assume they know and maybe some don't, but to hear things that as a male you would never be included in.
Sometimes I hear more than I want to I might add.
Cheryl T
02-19-2025, 10:44 AM
For me it was probably the day my wife was complaining about her bras.
They didn't quite fit this way or that and she was wanting to go shopping to buy a different size. I automatically went into a dissertation about the variance of size, that maybe she needed the same band with a larger cup or a larger band with a smaller cup and how cups sizes were equivalent if you went this way or that way doing this and that.
That's when I realized she was staring at me sort of amazed at the wealth of information I had about bras. I just said, "well I wear them too you know".
JesseVF
02-19-2025, 10:58 AM
For me when my wife is getting ready to do a delicate items wash and asks me if I have any bras to include.
@tammileetilliso
02-20-2025, 01:37 AM
I'm curious to know.
CDMargret
02-20-2025, 08:45 AM
I have thank you for asking. In a store with my ever so supportive wife. She comes up to me with a very nice blue silky blouse, holds it up to me and says "This will look good on you". Picked my jaw up off the floor and rushed over to the check out.
chrissy111
02-20-2025, 09:06 AM
Being in a club with my wife dressed and being asked to dance by a guy. And saying yes after some encouragement from my wife.
Debbie Denier
02-20-2025, 03:27 PM
Trying on a dress in a shop wearing a wig, nylons and stilleto shoes. Then showing the helpful CD friendly shop assistant and receiving her affirmation. That was the OMG moment for me.
NjJamie
02-20-2025, 04:18 PM
Amy, great topic question though I cannot just put one OMG moment above all the rest. A few life-altering ones I can recall like they were yesterday are below;
First time fully dressed, from toe nails to purse, perfume, coat and scarf, and going out the front door and driving away from my house, about 20 years old.
First time fully dressed and walking into a mall, business outfit in green and black, low black pumps, had a gentleman open and hold the door for me!
First CD meeting in Hackensack, NJ, the Garden State seems to have a very significant CD population, the night ended at a local Dress Barn which was open just for us.
First time meeting up with a CD friend, at a mall, just to shop and wander around, ended up at an Applebee's. Halfway through I noticed I had forgotten we were all dressed and pretty, she was just a friend and I was just Jamie.
Last one was the day I walked into Sephora for the first time, somewhat casual and nervous but they could not have been nicer!
I can't wait to try to top these, I guess it would be making the pilgrimage to Keystone, hope to see as many of you as possible when I do!
Joanie CD
02-20-2025, 04:41 PM
Several OMG moments (in no particular order):
1. First time putting on fingernail polish (what a magic moment!)
2. First time shaving my legs (I have little leg hair anyway, but it still felt great)
3. First time wearing (fake) hoop earrings instead of dowdy clip-ons
4. First time wearing actual women's prescription glasses instead of my boring male ones
5. First time wearing "real" makeup and not just daubing on foundation willy-nilly.
Heather76
02-20-2025, 09:10 PM
I believe my OMG moment was relatively early on. I was at a Ross Dress For Less buying my first dress. About a week later a woman co-volunteer where I volunteer asked how my wife liked the dress I bought and if I often bought clothes for her. I simply cannot/will not lie and told it was for me as I cross dress. I was 100% accepted and we've had many nice conversations about my hobby since that day. I often show her pictures of my latest purchase when I'm fully dressed and done up in makeup. She has often complimented the outfits and many times has told me she thinks I have great legs. At 79, I'm glad hose hides the spider veins. Anyway, that when I realized there are folks out there who, if they are friends, will accept this part of us.
mollymulligan
02-22-2025, 11:06 PM
For me, it was when i put on my first wig and makeup. I thought I would look similar to my male self and I was totally wrong, I loved how I looked and I flipped a switch in my head. I had a female side of myself that looked beautiful, at least to me and reflected how I felt
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