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On your first time out, what did you wear?

Started by ChrissyRyan, June 11, 2025, 09:11:41 PM

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ChrissyRyan

On your first time out, what did you wear?

How did it go for you?

Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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big kim

My girlfriends top and skirts.  I had some Cuban heeled ankle boots I wore. She helped with my makeup and did my hair in a long Joan Jett shag she put red streaks in
Went well. I ran into 2 guys I was riding with and his girlfriend  refused to  believe  it was me photographed with them
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Mandy Spencer

It was many years ago now - I recall a little black dress, stilettos and fixing on pink adhesive nails. It also involved a train trip and the train de-railed from the tracks quite vigorously. It all happened very fast and I remember wondering if i was going to die and be identified like this. All ended well though.
'Peace and Love'
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Jessica_Rose

We didn't have 'time out' when I was growing up. When I misbehaved, it was usually rewarded with my dad's belt contacting my posterior at a high rate of speed.

Oh, maybe you were asking about the first time we went outside as ourselves? That would have been when I went to my primary care physician to get a form allowing a gender update on my driver's license. I didn't have much to choose from back then, ladies jeans and a long sleeve ladies fleece top. It was frightening, but I survived. The only person who seemed to notice was me.

Love always -- Jessica Rose
Journal thread - Jessica's Rose Garden
National Coming Out Day video - Coming Out
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GCS II - GCS II and FFS w/Dr. Ley
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"It is never too late to be what you might have been." - George Eliot
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Lori Dee

It was a VA appointment with my Primary who knew me pre-transition. I wore a pair of tight jeans, black knee-high boots, and a T-shirt. It was Fall, so I had a light sweater over top. In the waiting room, a Korean War vet chatted me up and asked if I was in the WACS (Women's Army Corps), then commented that I was too young for that. I just smiled and said that when I was in the service, the WAC had been disbanded, so we were all just one Army.

My Primary said she liked my earrings, and one of the nurses said she liked my boots. So overall, it was a good experience.
My Life is Based on a True Story
Veteran U.S. Army - SSG (Staff Sergeant) - M60A3 Tank Master Gunner
2017 - GD Diagnosis / 2019- 2nd Diagnosis / 2020 - HRT / 2022 - FFS & Legal Name Change
/ 2024 - Voice Training / 2025 - Passport & IDs complete
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KathyLauren

Initially, I went out to support group meetings dressed androgynously: black pants, slightly colourful top.  No hair to speak of.

The first time I went out totally femme, to the support group meeting, I wore a dark green patterned skirt, with a green top, and my new wig.  They actually didn't recognize me! 

It was also the first time I used a women's bathroom.  It was an hour and a half drive home, and I had consumed coffee at the meeting, so a pit stop was required.  I pulled into a Petro Canada gas station, walked in, did my business and walked out, without meeting another person.  Whew!
2015-07-04 Awakening; 2015-11-15 Out to self; 2016-06-22 Out to wife; 2016-10-27 First time presenting in public; 2017-01-20 Started HRT!!; 2017-04-20 Out publicly; 2017-07-10 Legal name change; 2019-02-15 Approval for GRS; 2019-08-02 Official gender change; 2020-03-11 GRS; 2020-09-17 New birth certificate

ChrissyRyan

Quote from: big kim on June 12, 2025, 02:36:44 PMMy girlfriends top and skirts.  I had some Cuban heeled ankle boots I wore. She helped with my makeup and did my hair in a long Joan Jett shag she put red streaks in
Went well. I ran into 2 guys I was riding with and his girlfriend  refused to  believe  it was me photographed with them

Nice!

Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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ChrissyRyan

Quote from: Mandy Spencer on June 22, 2025, 07:49:39 AMIt was many years ago now - I recall a little black dress, stilettos and fixing on pink adhesive nails. It also involved a train trip and the train de-railed from the tracks quite vigorously. It all happened very fast and I remember wondering if i was going to die and be identified like this. All ended well though.

That turned out well then, overall.  Great!


Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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ChrissyRyan

Quote from: Lori Dee on June 22, 2025, 08:13:10 PMIt was a VA appointment with my Primary who knew me pre-transition. I wore a pair of tight jeans, black knee-high boots, and a T-shirt. It was Fall, so I had a light sweater over top. In the waiting room, a Korean War vet chatted me up and asked if I was in the WACS (Women's Army Corps), then commented that I was too young for that. I just smiled and said that when I was in the service, the WAC had been disbanded, so we were all just one Army.

My Primary said she liked my earrings, and one of the nurses said she liked my boots. So overall, it was a good experience.

Seems as if that went well!

Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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ChrissyRyan

Quote from: Jessica_Rose on June 22, 2025, 05:15:42 PMWe didn't have 'time out' when I was growing up. When I misbehaved, it was usually rewarded with my dad's belt contacting my posterior at a high rate of speed.

Oh, maybe you were asking about the first time we went outside as ourselves? That would have been when I went to my primary care physician to get a form allowing a gender update on my driver's license. I didn't have much to choose from back then, ladies jeans and a long sleeve ladies fleece top. It was frightening, but I survived. The only person who seemed to notice was me.

Love always -- Jessica Rose


Jess,


I am glad this first time turned out rather benign.  Look back, you have come a long way!

Christine
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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Jenn104

I surprised my therapist- a big, grey, supremely frumpy dress with black boots. I'll add it was back in the clown-makeup days, the stage where I hadn't really figured out less is more with respect to makeup on my face. I felt so good.. I stopped at one store and shopped on the way home.

I am very friendly with my therapist. I've told her she is very good at what she does because how she kept a straight face I will never know.

~Jenn
"I want to be remembered as a woman ... who dared to be a catalyst of change."
                 - Shirley Chisolm

"We need to love ourselves first, in all our glory and our imperfections."
                  - Marsha P. Johnson

"Why not question everything?"
                  - Lynn Conway

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Allie Jayne

I came out to my work colleagues in September 2019, and they were excited to meet their new female colleague, but I had never been outside as myself before, and I told them that they would have to wait a few months until I was ready. Not satisfied with that, they booked me into a "transitioning at Work" seminar in a nearby city, then after I accepted, they said all 6 of them were coming with me.

I planned to go in my usual work uniform, but they then told me they had arranged for me to meet the keynote speaker, and I needed to present as myself so I could get some private advice. I felt so much gratitude for the support they were giving me I bought a new outfit with pants and a nice top, appropriate for a business occasion. This wasn't good enough for the 5 women, who told me they had all agreed to wear dresses on the day to support me. I mean, with people being so supportive, how can you refuse? I chose a black summer dress with a light branches and leaves pattern, sandals with a small 1 1/2 inch block heel, and a black handbag.

I was terrified when they knocked at my house door to pick me up, and a little miffed to find only one of the other women was wearing a dress! I took the first steps out of my house as me, but this was not going to be easy!

The seminar was in another city a couple of hours away, and it was decided we should take the train, so I had to face a station full of commuters, then being stuck on the busy train for over an hour before arriving at the main station with thousands of people milling about! The seminar was in a building a couple of blocks away from the station, so we walked there, but to my horror, we had to pass through a large protest crowd. That was when I noticed the network news cameras pointing at me! To get through to the seminar, we had to pass through a police cordon, and answer questions about what we we doing in the area.

Finally at the seminar, I realised I had actually gotten this far without anybody really noticing me, and I could not have imagined a worse scenario for my first outing! The seminar over, the speaker was mobbed, so I didn't get to talk to them, and we went to lunch at a crowded riverside restaurant. I got lot's of compliments from my colleagues, my boss even suggested I looked so natural as a woman that I should just be myself at work from then onwards.

But this wasn't time to relax, as now I realised I needed to go to a restroom! One of my colleagues came with me and we did our business and checked our hair and faces in the mirror just like the other women in the rest room with us. Nobody screamed and pointed, it was all very normal. The trip home was the reverse of the trip there, except that now it did feel normal. A couple of the ladies told me they were very comfortable with me as female, and from now on I should share the women's restroom at work!

As usual, life is a bit more complicated than that, and it was a horror day for my wife as she felt it was now certain she had lost her husband. My colleagues were visibly disappointed when I came to work the next day in my normal uniform, and I explained to them that if I had worn female clothes to work, I would have gone home to an empty house. I planned to give everyone some months to get used to the idea of me transitioning and it was 3 months before anyone saw me as myself again.

So on my first time out, I truly dived into the deep end and faced so many more challenges than I could have imagined! It was maybe the most important day in my transition, as up to that point, I was drowning in self doubt that I could actually face life as a woman, but, for the first time in my life I entertained the thought that a future for me was possible!

Hugs,

Allie

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Pema

Wow, Allie. What a beautiful, descriptive, powerful story. I know that I can't even imagine the contrast between the extremes of all that you felt that day. You are an extraordinary person. I feel very fortunate to benefit from all that you share here. I mean that sincerely.

Pema
"Though we travel the world over to find the beautiful, we must carry it with us or we find it not." - Ralph Waldo Emerson
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tgirlamg

Quote from: Mandy Spencer on June 22, 2025, 07:49:39 AMIt was many years ago now - I recall a little black dress, stilettos and fixing on pink adhesive nails. It also involved a train trip and the train de-railed from the tracks quite vigorously. It all happened very fast and I remember wondering if i was going to die and be identified like this. All ended well though.

I had the same wardrobe as Mandy first time out in 2013 but, no transportation disasters! All went well... after a lifetime of fear it was all very anti climactic since no one batted an eye... I didn't even have the crowd of villagers chase me with torches and pitchforks!

Onward!

A 💕
"To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment" ... Ralph Waldo Emerson 🌸

"The individual has always had to struggle from being overwhelmed by the tribe... But, no price is too high for the privilege of owning yourself" ... Rudyard Kipling 🌸

Let go of the things that no longer serve you... Let go of the pretense of the false persona, it is not you... Let go of the armor that you have worn for a lifetime, to serve the expectations of others and, to protect the woman inside... She needs protection no longer.... She is tired of hiding and more courageous than you know... Let her prove that to you....Let her step out of the dark and feel the light upon her face.... amg🌸

Ashley's Corner: https://www.susans.org/index.php/topic,247549.0.html 🌻

ChrissyRyan

Quote from: Jenn104 on June 23, 2025, 07:28:33 AMI surprised my therapist- a big, grey, supremely frumpy dress with black boots. I'll add it was back in the clown-makeup days, the stage where I hadn't really figured out less is more with respect to makeup on my face. I felt so good.. I stopped at one store and shopped on the way home.

I am very friendly with my therapist. I've told her she is very good at what she does because how she kept a straight face I will never know.

~Jenn


Thank you for sharing!

Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 
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ChrissyRyan

Quote from: Pema on June 23, 2025, 11:05:19 AMWow, Allie. What a beautiful, descriptive, powerful story. I know that I can't even imagine the contrast between the extremes of all that you felt that day. You are an extraordinary person. I feel very fortunate to benefit from all that you share here. I mean that sincerely.

Pema
Quote from: Allie Jayne on June 23, 2025, 08:06:25 AMI came out to my work colleagues in September 2019, and they were excited to meet their new female colleague, but I had never been outside as myself before, and I told them that they would have to wait a few months until I was ready. Not satisfied with that, they booked me into a "transitioning at Work" seminar in a nearby city, then after I accepted, they said all 6 of them were coming with me.

I planned to go in my usual work uniform, but they then told me they had arranged for me to meet the keynote speaker, and I needed to present as myself so I could get some private advice. I felt so much gratitude for the support they were giving me I bought a new outfit with pants and a nice top, appropriate for a business occasion. This wasn't good enough for the 5 women, who told me they had all agreed to wear dresses on the day to support me. I mean, with people being so supportive, how can you refuse? I chose a black summer dress with a light branches and leaves pattern, sandals with a small 1 1/2 inch block heel, and a black handbag.

I was terrified when they knocked at my house door to pick me up, and a little miffed to find only one of the other women was wearing a dress! I took the first steps out of my house as me, but this was not going to be easy!

The seminar was in another city a couple of hours away, and it was decided we should take the train, so I had to face a station full of commuters, then being stuck on the busy train for over an hour before arriving at the main station with thousands of people milling about! The seminar was in a building a couple of blocks away from the station, so we walked there, but to my horror, we had to pass through a large protest crowd. That was when I noticed the network news cameras pointing at me! To get through to the seminar, we had to pass through a police cordon, and answer questions about what we we doing in the area.

Finally at the seminar, I realised I had actually gotten this far without anybody really noticing me, and I could not have imagined a worse scenario for my first outing! The seminar over, the speaker was mobbed, so I didn't get to talk to them, and we went to lunch at a crowded riverside restaurant. I got lot's of compliments from my colleagues, my boss even suggested I looked so natural as a woman that I should just be myself at work from then onwards.

But this wasn't time to relax, as now I realised I needed to go to a restroom! One of my colleagues came with me and we did our business and checked our hair and faces in the mirror just like the other women in the rest room with us. Nobody screamed and pointed, it was all very normal. The trip home was the reverse of the trip there, except that now it did feel normal. A couple of the ladies told me they were very comfortable with me as female, and from now on I should share the women's restroom at work!

As usual, life is a bit more complicated than that, and it was a horror day for my wife as she felt it was now certain she had lost her husband. My colleagues were visibly disappointed when I came to work the next day in my normal uniform, and I explained to them that if I had worn female clothes to work, I would have gone home to an empty house. I planned to give everyone some months to get used to the idea of me transitioning and it was 3 months before anyone saw me as myself again.

So on my first time out, I truly dived into the deep end and faced so many more challenges than I could have imagined! It was maybe the most important day in my transition, as up to that point, I was drowning in self doubt that I could actually face life as a woman, but, for the first time in my life I entertained the thought that a future for me was possible!

Hugs,

Allie





Allie,


That was quite the first outing.  Thanks for sharing.

Chrissy
Always stay cheerful, be polite, kind, and understanding. Accepting yourself as the woman you are is very liberating.  Never underestimate the appreciation and respect of authenticity.  Help connect a person to someone that may be able to help that person.  Be brave, be strong.  A TRUE friend is a treasure.  Relationships are very important, people are important, and the sooner we all realize that the better off the world will be.  Try a little kindness.  Be generous with your time, energy, wisdom, and resources.   Inconvenience yourself to help someone.   I am a brown eyed, brown haired woman. 

D'Amalie

Some 6 years ago I wore Torrid jeggings, a pink linen untucked top with puff short sleeves/modestly see through lacy shoulders/upper front showing off white bra straps and top of lacy cups peeking, off white Keds, invisible socks (bare ankles), mascara/eyeliner, half inch white gold hoops earrings/heart diamond necklace.  I went shopping in the best mall in the area.  Confident and smiling, walking as tall as 5ft8 can do...

Interestingly, women checked me out more than men.  Yet no sign of "clocking." 
One shouldn't open the book of another's life and jump in the middle.  I am a woman, I'm a mystery.  I still see and hear who I used to be, who I am, who I'm gonna be. - Richelle
"Where you'd learn do to that, miss?" "Just do it, that's all; ... I got natural talent." "I'll say you do, at that." - Firefly
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