Susan's Place Transgender Resources

What was it like for you the first time you put on woman's clothes and got all dressed up?



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The single word that comes to mind is "Magical". The first time I fully dressed I felt like a different person. I felt calmer, more comfortable in my skin and clothes than I'd ever felt before. It was only slightly spoiled by the fear of being caught. I didn't really understand why I wanted to do it, I just know it was something I had to try. I knew it was going to be an ongoing thing and the more I did it, the more I wanted to. I've never looked back. Something that feels so right can't be wrong. No matter what others may think.

Quote from: Aeirs on July 19, 2015, 11:28:30 PM
What was it like for you the first time you put on woman's clothes and got all dressed up?

Enthralled!

barbie~~

Felt good seeing there was something very different about me.

REAL sexual, real guarded/defensive/secretive . . . and confusing.

Mostly passed all that now, more integrated, less fragmented.

"Orientation is who you go to bed WITH

Gender is who you go to bed AS."  -- Caitlin Jenner

Never been a male in a sexual relationship. I'm always "female" -- but it's about relationships, not sexual performance . . . Your mileage may vary. The "line" for me is mostly just open space, waiting to be defined. I go back and forth across -- bump around comfortably in the middle -- now without much thought. "Do these clothes coordinate color/style? Are they functional/practical for the day's activities?" That being the SOLE criteria. Somewhere in the "middle gender" -- not the hetero-normative dyad.

We've dropped the men's Eddie Bauer pocket vest in favor of a black, tablet-size laptop bag, holds what I need, even a .357 magnum, carry permit . . . & seamlessly stylish, practical, integrated, unobtrusive. Doesn't scream "girlie purse!" . . .

Interesting, significant that once "out of the defensive/fragmented me" -- a lot of the sexual dysfunction, fixated fetishes, DISAPPEARED. I became more integrated, less anxious.

Let's note here that I'm 100% service connected and the VA diagnosis is: "Gender dysphoria, paraphilias . . . "

But it's not "fetish" once it gets integrated. That's the progress I recently made in 50 yrs of therapy. I don't feel "dysfunctional/fragmented" and more.

I've never fully dressed, believe it or not.

The first items I wore were mom's denim skirt and her leather skirt.

It felt stress relieving and confidence boosting.

Sensual.

:)

It felt amazing. And it felt so right too.

Like I can finally be me

The first time I tried on pantyhose it was energizing and confusing.  I was 4 or 5 so it wasn't sexual.  I found myself drawn to pantyhose over and over again and eventually I fully dressed in moms things more as a extension of what I was already doing.  In my mind I had to dress up if I was going to wear pantyhose.  But the slip, dress, shoes, hose, wig ect made me feel good.  Then I felt like a fraud, and guilt set it.  It was such a strange mix of good and bad feelings.  More good though which is what kept be going back.

Years of guilt, hiding, and denial wrought a conflicted self into my late 20's.  As I approached my 30's a switch flipped.   I realized that's who I am... it won't change and I finally embraced it.  There's a lot more dots to connect, but dressing has been a mixed bag for me over the years.

Today it's centering for me.  Dressing up in even a skirt and hose is enough to make me feel sexy and alive: like I belong in the world.  There's enough change that my wife see's this and helps make opportunities for me to dress.

I thought it was amazing and felt like it was so special and beautiful and wondered why boys couldn't wear girls clothes all the time because they felt so much better than my male clothes. Boys clothes were so rough and boring but girls clothes were so frilly and soft. It was very arousing as well and sometimes still is.

I just couldn't believe how comfortable my suspender belt and stockings felt.

I could feel my bra straps and band being slightly tight and strappy, and my heels made my legs ache, but I wore my suspender belt & stockings in bed and throughout the next day.

I only took my stockings off after I laddered them following some "robust" activities!   

Suddenly I understood why I would obsess over any girl that wore a skirt or dress to school, I was also very confused and scared.

Crossdressing to me when I first tried it, as an experiment, simply felt right.

Quote from: KatelynBG on August 01, 2015, 01:29:32 PM
Suddenly I understood why I would obsess over any girl that wore a skirt or dress to school, I was also very confused and scared.

Yeah, tough sledding for a first grade kid.

Quote from: Allison Wunderland on August 08, 2015, 02:38:05 PM
Yeah, tough sledding for a first grade kid.

Yeah everyone thought I was the school perv but I didn't learn how to climax until high school.

Quote from: KatelynBG on August 08, 2015, 02:56:58 PM
Yeah everyone thought I was the school perv but I didn't learn how to climax until high school.

I remember being enthralled by the women at school growing up (teachers and students) and the things they could wear.  I find myself admiring outfits out and about even to this day, and I'm fortunate that my wife knows I'm primarily looking at the outfits.  I guess I was pretty good at hiding it, but I felt like a perv at times but really it was envy.

I think the first time, I was too young for it to be a hugely sexual thing but the adjectives make it seem that way.

Exciting(maybe just worried about being caught), sensual(all senses felt heightened), tingly? and as others have said, just right.

Later, when I tried a one piece swimsuit then stockings and a slip under a dress, it was all the same. By then it had a sexual quality as well, but it still felt so just plain right.

Joanna

The first time that I FULLY dressed, I still remember the feeling of calm. Everything felt just right. I felt feminine, I felt the way I always wanted to feel. When I looked in the mirror I saw the girl I had waited over 50 years to see. I cried a little.
There was no one to interrupt me so I spent the evening dressed doing normal things about the house. I had put on makeup for the first time - probably badly but that did not matter.
I will never forget tat first time. It was magical.
It still is magical to dress fully☺️.
Ciara.

I used to steal my sisters clothes after they moved out and did this when my parents went shopping. (And sometimes while they were there O.O). And I was really little, maybe 9-10ish. I'd go into their rooms and wear their old clothes. It was magic, I didn't know why I felt that way, the only time i've ever heard about "boys" wearing girls clothing was that it was sinful. But I just remember feeling so comforted, way more comfortable than i've ever been before. It also felt kinda sensual and tingly and tense (probably because I was so scared of getting caught).

I felt just like a princess looking into that mirror. Now, I can wear those clothes and feel like a princess every day :)

Quote from: Alice Borealis on August 24, 2015, 09:51:20 AM

I felt just like a princess looking into that mirror. Now, I can wear those clothes and feel like a princess every day :)

Lucky you. ☺️☺️

Hi, it was like the cloths i was putting on was completing me, and i enjoy what i saw in the mirror. The change was a perfect fit

amanda

Quote from: Aeirs on July 19, 2015, 11:28:30 PM
What was it like for you the first time you put on woman's clothes and got all dressed up?

The first time? It was when I was three or four years old. I don't remember. Seriously.

As an adult, the first time I got all dressed up and took a pic of myself, I was seriously discouraged. I looked like an overweight guy in an ill fitting dress. I went through a lot of pain and public humiliation until I could pull it all together.

Cindi

Just blew my 8 year old brain...dumbfounded because there in the mirror was that dam girl making all the racket in my head....more of a feeling like I knew I was right...happy, secure, warm...I was to stunned and naive to realise what it meant for me and I knew I would do this again as soon as I could.

Oh, I must add that in high school (early 70's) I purchased girls' clothes to wear to school. Orange velvet hip hugger bell bottom jeans and a button up the front flowered blouse. I had long hair too. I was mistaken for a girl by a teacher I did not know. From then on, I used that outfit to go out shopping for "stuff" that I needed to play dress up. I was very happy indeed that I got no second looks or glances purchasing those little personal items and nice shoes. Sadly, I purged those things many times. What a waste. Had I even known about transsexuals (that's what we were called back then), my life may have been completely different. I thought I was the only one of my kind and such a pervert. Gawd I hated puberty and what it did to me.

Cindi

Quote from: Cindi Jones on August 27, 2015, 03:52:06 PM
Oh, I must add that in high school (early 70's) I purchased girls' clothes to wear to school. Orange velvet hip hugger bell bottom jeans and a button up the front flowered blouse. I had long hair too. I was mistaken for a girl by a teacher I did not know. From then on, I used that outfit to go out shopping for "stuff" that I needed to play dress up. I was very happy indeed that I got no second looks or glances purchasing those little personal items and nice shoes. Sadly, I purged those things many times. What a waste. Had I even known about transsexuals (that's what we were called back then), my life may have been completely different. I thought I was the only one of my kind and such a pervert. Gawd I hated puberty and what it did to me.

Cindi

I hope that with the Internet that the younger kids going through what we did (feeling alone and like a perv) can find help and support and understand who they are much sooner in life.  I took me getting to my 30's to sort it all out.. sometimes I wonder where I would have landed if I'd done that work at an earlier age.

Great question.  It just felt right.  Overall all, a feeling of well being.  Still feels that way today. Y

Quote from: Kerry30Den on August 27, 2015, 10:26:10 PM
I hope that with the Internet that the younger kids going through what we did (feeling alone and like a perv) can find help and support and understand who they are much sooner in life.  I took me getting to my 30's to sort it all out.. sometimes I wonder where I would have landed if I'd done that work at an earlier age.

As a precursor to the internet, I had access to CompuServe. 100kByte modem, a computer that I had soldered together myself, and six dollars per hour. Real time chat with a few others, perhaps a dozen or so at any one time. I could only afford one or two hours per month. But I met two friends there who are still friends. One transitioned and one did not. All the time, I had a spousal type person who'd open the door at will to see what I was doing. But having that contact was so helpful and supportive. It was probably that access which helped break the proverbial camel's back. It's hard to pinpoint that straw, but yeah, that was it. I had access to "acquaintances" around the country. I traveled a lot with my job. I'd keep a packed bag in a storage locker for "her" and make a stop on the way to the airport. Everywhere I'd go, well all the big cities anyway, I had someone who could help, go out with, or just be supportive. It was quite an emotional ride.

I'm thrilled that younger people can now get instant access to all sorts of information, including videos of some very brave young women. Good for them! What a godsend.

Cindi

Confusing. But also soft, delicate and comforting.

Loved it when I was very young,mom's pantyhose.First time out dressed in public when I was 7 years old,decided I wanted to dress as a girl for Halloween,mom was for it and my bio dad said no way.It did happen,an aunt of mine had some clip on earrings I could wear.Mom and I went into a second hand store and found me a cute dress to wear including a pair of shoes.Did my about shoulder length hair and my mom did my nails.My mom and aunt thought I looked pretty as a girl.I still remember it to this day.Mom was told that she had a pretty daughter when we went out trick or treating.Mom still remembers it also.My twin sister Taylor remembers the day too,she was dressed as a cheerleader when this happened.Said I looked pretty as a girl.

Quote from: Alice Borealis on August 24, 2015, 09:51:20 AM
I used to steal my sisters clothes after they moved out and did this when my parents went shopping. (And sometimes while they were there O.O). And I was really little, maybe 9-10ish. I'd go into their rooms and wear their old clothes. It was magic, I didn't know why I felt that way, the only time i've ever heard about "boys" wearing girls clothing was that it was sinful. But I just remember feeling so comforted, way more comfortable than i've ever been before. It also felt kinda sensual and tingly and tense (probably because I was so scared of getting caught).

I felt just like a princess looking into that mirror. Now, I can wear those clothes and feel like a princess every day :)

you go girl! Keep being a princess.

It was a sexual rush for me when I put on my moms underwear, hose, skirt and blouse before cramming my feet into a pair of her shoes.  She was 2 sizes smaller than me. 

Scared, and exhilarated rolled up together and tied with a pink and red polka dotted bow. Not much has changed other than I like all colors of polka dots now :angel:

I was 13. I wanted to go trick or treating so bad, I would have gone naked. We had just moved into a new city & apt complex. Our household goods were in transit. Mom said "If you wanted to go t-or-t so bad, I can put you in one of Shasta's dresses & you go  as a girl!" Not sure if she was serious or not. But I said yes. After showering & dressing, Mom pushed me out the door. It was 630 or so. dark already. All sorts of thoughts were going thru my head plus the cold wind up the dress, across my Naired skin, heavy eyelashes, lipgloss, the bra tugging. All new experiences. I took a deep breath & said "Oh, well" & was on my way. That seems to have helped me whenever I go out 'en femme'. A deep breath & an Oh Well attitude.

In Apr '14 my GF/mentor Vikki decided that we couldn't hide it anymore that I was turning into a girl. So she decided to throw a party. She told everyone that my cousin Bridget was moving to the city & wanted to meet us. She told everyone to be there at 630pm. The day of, she sent met to a Beauty Salon that does CD,TG,TF for a makeover. At 615 or so I was sitting at Vikki's lighted vanity scared >-bleeped-<less. She put her hand under my chin, digging her nails into it, pointed me at the mirror & said that I shouldn't be nervous. She handed me an airline bottle of Seagrams which I downed. She said that she would introduce me at 635. She said to listen at the door. After she left, I locked the door. At 640 I could hear her say "Friends, I have a confession. There is no cousin Bridget. Jul of last year Jim told me that he likes to CD & that he wants to become a girl. My work, Alpha-Medical has been helping him. So I'd like to introduce you to Bridget Yvonne!" I walked down the stairs & stood at the landing. Everyone kind of OOHH & AAHHd. A few said "doesn't look like Jim." Then Sheri, Vikki's stepsister said a few mean things at me but mostly Vikki like "Oh, I guess we know who wears the pants in this couple." etc. I just wanted to kick Sheri. The door swung open & there was Dave, an ex coworker of mine. He says "Who's the chick in the skirt?" Don't know why but I ran into the cold Oregon rainy night. I ran until I got to a park that has a bridge that goes over the river. I sat under the bridge, wondering. Mostly wondering why I didn't dress warmer. I then heard "Jim Jim" I them heard  a girl say "Her name is Bridget, stupid" then I heard "Bridget" I called to then & my sister Shasta shows up. She hugs me & gives me a coat to wear. Others gather & we walk back to the condo. There is cake & Coffee. As I am sitting there, one girl asks Vikki "So how did you feel meeting Bridget for the 1st time?" Vikki giggles & tells them the story. She said that she gave me an hour to change into Bridget. She said that it was either the longest hour or the shortest. She said that as she sat there, she told herself 'If he looks like Klinger on Mash or an extra on To Wong Fu' I will kick his ass! Everyone laughed. She said "He looked actually passable. Bad nail polish job, obviously a wig but passable." A few girls joked by saying "Decided to join the winning side?" I replied "Just had to wait for my uniform."