Most Daring Thing You Have Done Crossdressed?

[Guest Leila]

Wow everyone has such amazing stories I can't even begin to compare.

So when I was in my early twenties and home from college over summer break, I'd often sneak out in the middle of the night at 2am or something when my parents were asleep wearing a skirt and whatever mismatched clothes I had pieced together at the time. It was the biggest adrenaline rush. I remember scoping out the neighborhood since we lived near a trail by the bay. My goal was to get to the trail which is completely unlit and just walk and feel the breeze blowing on my legs and be able to be 'out' in public (well sort of) but the problem was that the neighborhood was very well lit. I had to walk a good several blocks completely exposed to my neighbors before reaching this trail.

I remember working up the courage to do this. I'd sneak downstairs, and really slowly open the front door, making sure I was as silent as possible, and when it opened, the sensor at the front door light would activate scaring me silly. After a few nights only going to the door and opening it, I eventually ventured outside, took a few steps and scurried back in.

Anyway, after goodness knows how many attempts, I finally got the courage to walk outside. I went as quickly as possible to get to the trail hoping no one would see me. The trail goes on for miles and was absolutely freeing to be walking outside dressed. There were quite a few close calls as sometimes other people would be walking too in the dead of the night. I remember hiding behind bushes more than a few times to avoid detection from a group of rowdy teenagers.

Well this one time, I was walking and this car passed with the headlights beaming right at me. It passed then I saw the brake lights go on, and it stopped maybe 40 feet ahead and I freaked out. So I started heading the other way. Luckily for me, no one got out of the car and I went on my merry business but that was scared. It was a huge rush but I remember feeling terribly ashamed and guilty. It wasn't until later when I reflected on it when realized how stupid it is to go walking outside alone in the dead of night. I could have been jumped, beaten or worse.

To all the sisters out there, please be smart and above all be safe.

Hugs,

Leila

[Guest Michaele]

Never flew like Donna Jean during my time over there but all I can say was it was a bit difficult getting changed in the hooches back then. Oh and by the way Donna, I thought that bras and panties were standard wear when in our zoot suits...LOL!!!! I had a flight nurse come up on the flight deck, put her hand on my back (I was reaching over to the lower CB panel by the bunk) and looked at me kind of funny. I saw her again by the galley after I ducked into the underdeck area and put on my shoulder harness. I started adjusting my shoulder harness in front of her. The look on her face was priceless

Yikes I just had a flashback of hanging that 2 inch .38 in the stupid shoulder holster, under the zoom bag on top of a t shirt with a bra under it. Straps all over the place.

[Guest Michellewhois]

Yikes I just had a flashback of hanging that 2 inch .38 in the stupid shoulder holster, under the zoom bag on top of a t shirt with a bra under it. Straps all over the place.

:lol: And I hated it when the holster strap would push the bra strap down on my shoulder or the irritation of the breast straps rubbing together

[Guest ChloëC]

Sometime back in the early 1970's I was living in a two flat. The only entrance/exit was down some stairs in the back (outside) and the owners downstairs were constantly listening or checking or just spying on who came up and down the stairs, as well as listening to every move made above them. I dressed up in a dress, pantyhose, heels, wig, makeup, padding snuck down the stairs and around to the front where my car was parked and drove around town, came back, parked and went back up stairs. This was later in the evening so it was a little dark. But I was terrified.

A few years ago, I did the same thing, but I now live in the country, so I can dress and get in my car with little worry. But I was driving down the country road, coming up to an elevated railroad crossing (just a signal, no gates) and just as I slowed down to look both ways, a car came out of a farm drive right at me from my right side, headlights fully illuminating my car. Deer in the headlights, I suppose. It was about 10PM and dark. What a coincidence. I was in a dress, breast forms, heels, wig, makeup.

I was seriously thinking of going about 20 miles or so to a post office where the lobby was open to midnight and I had a box (near where I worked.) I lost my courage.

Oh, and once a long time ago, I was living in an apartment and walked the trash out late at night through the halls, across the parking lot. I was scared every step.

Sum total of my excursions in 'public' dressed. Of course, for awhile I very occasionally wore lingerie and hose under my clothes and was constantly worried about doing something stupid and winding up in the emergency room. Well, every one of the above times.

Hugz

Chloë

[Guest Donna Jean]

Yikes I just had a flashback of hanging that 2 inch .38 in the stupid shoulder holster, under the zoom bag on top of a t shirt with a bra under it. Straps all over the place.

:lol: And I hated it when the holster strap would push the bra strap down on my shoulder or the irritation of the breast straps rubbing together

DANG!

Yes...I HATED that dang .38 shoulder strap!

It got in the way of important straps!

Dee Jay

[Guest Wendae]

As I think back to Vietnam I remember how hot and humid it was. Rained everyday for the first 6 months I was there. The rest of the time it was hot and dusty.My clothes, crotch and feet were rotting away. Our hooches were not airconditioned nor was there any privacy. I don't remember wanting to get femmed up but, I sure wanted to get a bath in clean water.

I had to laugh thinking of those of you being underdressed. Discovery would have been a quick trip home. The VC would have had a ball if you were unlucky enough to become POWs. You girls sure were gutsy!

[Guest Donna Jean]

I had to laugh thinking of those of you being underdressed. Discovery would have been a quick trip home. The VC would have had a ball if you were unlucky enough to become POWs. You girls sure were gutsy!

Well yeah, that was my biggest concern......

A trip to the "Hanoi Hilton" while in matching bra and panties.....

I woulda been in quite a jam....

Dee Jay

[Michelle 2010]

"Hanoi Hilton"...A different kind of French Quarter, huh Dee Jay?

Dang, I didn't know we had so many crossdressing GI's,

I just remembered the first time traveling for business when young and staying in a hotel nicer than I was used to. I had a Aqua color silky robe I was wearing and put the room service tray outside the door @11 pm... You know what happened...Door locked when closed...no key...

Needless to say, I became a verrry careful crossdresser after that

Michelle

[Guest Michaele]

Michelle,

Isnt the the crossdressers recurring nightmare?

Big Hugs

Shelley

[Guest Michellewhois]

Dang, I didn't know we had so many crossdressing GI's,

Michelle

There were a few of us around back then. If the military only knew just how many of us there were, they might have started an optional issue of those plain jane undies to all of us :lol:

[Sally]

Well it wasn't in Viet-Nam but it was the same era - I was in college sweating out the draft and playing intramural basketball - often wearing pink panties under my shorts - the scariest part was counting the waistbands before you pulled off your warm-ups.

Actually if you had seen some of the outfits that I wore in the 70s you might of thought that I was cross dressing all of the time - platform shoes (yes, even at my height), shoulder length hair - blue flair leg jeans with vertical white and pale blue braiding the full length of them - silk shirts with giant patterns that wrapped around my entire skinny body and even a baby blue belt or the yellow jump-suit - but then so was everyone else.

I thought it was daring at the time - at least Dee Jay did not carry a pink pistol with her.

Love ya,

Sally

So Sally, was this look like Ziggy Stardust (David Bowie) or the O'Jays without an afro that you were doing:) ?

Hugs

Michelle

More toward the O'Jays without the Afro (not very curly hair) - I was not bold enough for the Ziggy Stardust look!

Well, I out grew those days and shifted over to the much milder Hawaiian Aloha shirts!

People assumed that I wanted to be Magnum but in fact I was not aiming for howlee kane (main lander male) but rather just a kamahina wahine (Islander female).

Love ya,

Sally

[Guest JaniceW]

I think we need some Emergency Room stories here.....I know there out there...

Well I did used to wear pantyhose under my uniform when I worked in the ER as a nurse, it's not a bombing run but there were a lot of "bombed" people around.

[Guest Michellewhois]

Sum total of my excursions in 'public' dressed. Of course, for awhile I very occasionally wore lingerie and hose under my clothes and was constantly worried about doing something stupid and winding up in the emergency room. Well, every one of the above times.

Hugz

Chloë

Hun

I think that we have all had those thoughts at one time or another about ending up in a situation that would require us to disrobe at a hospital. I bet it might cause a bit of embarrassment to have a nurse walk in and find one of us sitting there in a gown and panties.

[Guest Daniel Dee]

THe most daring thing I ever did was when recently I bought a backless dress and needed a bra to go with it but didn't have a clue as to what. So one day I was down town, in male attire, and just decided to go into a big store and I went to the lingerie department and just explained to the assistant my problem and she was very helpful but hadn't got the extension straps I needed so sent me to another store. Neither had they so I was sent to a special lingerie shop where the most kind and helful asistant got me what I needed. After that I had no inhibitions about going to lingerie shops.

[Guest Rowan19]

Yelling profanities at a bio male.

[Guest darlene lynn]

Hey

I cant resist commenting to the emergency room. This isnt an emergency room story but it allmost was. I went to family doctor to get meds renewed. Doctor decided to do a physical on me. Which I didnt even think would happen,so I wasnt dressed for it. I was sure doctor felt bra when listening to heart, and when she had me drop my panties for prostate examine, I have no dought that put the icing on the cake for female doctor and ME. By the way she is still my family doctor and has been for about 12 years now so I feel much calmer with her now.

Ha! Ha!

Darlene Lynnette

[Guest Rowan19]

Yelling profanities at a bio male.

The funny thing is I wasn't technically 'dressed' at the time, they all just thought I was male so I went along with it. Hope it still counts.

[Guest Fran]

I took a 500 mile trip in my car wearing C cup breasts and 5" HH. It was in the winter so when I got out of the car I wore a hooded jacket. It fit tight so you could still tell I had breasts and the heels were visible. I did stop for fuel dressed, but removed the breast forms and heels before checking in at the motel. I did go out for a walk dressed that evening. I wanted my head covered as I didn't have a wig, but the feeling was wonderful. I did the same thing on the return trip. I have also taken walks around a park close to where I live at night wearing a hat to cover my head an wearing my DDD forms. I don't wear my heels as they are not for long walks.

[Guest Sarah Miller]

Going into combat probably tops the list! When I was 15 my sister ran away from home to live with our father, this was when I stated dressing up in girls clothes. No one at home for the first time ever when my mother was at work. I found, however, some school uniforms of hers and on a few occasions wore them to school under my male uniform. I had to of course choose a day where there was no sports otherwise all would have been revealed!

Sarah

[Guest laura g]

I'm going to have to chime in on this one, I'm a firefighter and yes I've gone into a burning building wearing a bra and thong! the funny part was i did not even realize i was wearing them until we were cleaning up. i volunteer so we get paged through radios. i was in my room doing homework, dressed in full femme. the page went out and i had a huge shot of adrenaline rush as i do with every fire call. i quickly stripped, left my clothes sprawled out all across my room (with my family home) and through on my male clothes and rushed out the door. i got on scene and threw on my turnouts and went into the house. it was only when i went to take off my coat that i felt my bra under my shirt and i realized i had never taken them off! i was soaking wet with only a thin blue t-shirt on. i looked down and you could see my pink bra. i quickly looked around to see if anyone had seen it. thankfully no one did, and i threw my coat back on. they were all wondering why i didn't take off my coat while we were overhauling! haha whoops!

[Guest Jaded1]

Since this thread came up I have thought long and hard about what would be the best thing to put in here. I think back to all the times I dressed up like a woman and the events that came about. I even (remnants of male ego I guess) dismissed them all as they couldn't ever "one up" some of the others here so they wouldn't be worth mentioning.

And today it finally came to me.

I guess sometimes you really can not see the forest from the trees and it took me looking in the mirror today to realize it.

The most daring thing I have done cross dressed was live 31 years of life pretending to be someone I am not. Putting on the male clothes that were my shield, my armor, my uniform so that the outside world would never have an inkling of what I feel beneath those clothes.

Sure I let my hair grow out and occasionally I would let my fingernails grow a little longer than I was "allowed" by societal norms, but my sharp wit always had an answer for the quizzical minds around me.

See it is now I finally realize that I had things flipped all along. Even though I was born in the body of a man and did a darned good job all these years convincing others that that was me. So much so that I even convinced myself that I never realized this:

I thought that when I put on a dress and makeup and a nice pair of heels, I was "presenting" female. That phrase never really sat well with me and it is because I never present(ed) as female. I AM female. The presentation was presenting as a male for 31 years.

So to close it up, the most daring thing I have ever done crossdressed was attempt to fool myself that I wasn't,

[Guest mia 1]

this is the most daring thing I’ve done admit to myself that I am a cross dresser for life and that I always will be......letting my chest and leg hairs grow out and pretend that I was no longer a c d’r....well I am leaving that river in Egypt and coming home...and feeling good about it all..

very good...

[Guest Hollie W]

2 very powerful last posts there.

I stopped cross dressing when I married 9 years ago. Within 2 years the urges began and I have secretly dressed ever since. I am soon to be divorced and can't wait. Like you Mia, I realise I am a cross dresser for life and things are going to be very different this time around. My first steps...joining a fantastic forum

[Guest toni2007]

I suppose the most daring thing for me, was sending a picture of myslef in full drag to the last living member of my family. ( my sister) with a not that it was who I am.

Toni

[Petra Jane]

I guess the most daring thing I've done was one night I was wearing my bra and panties along with a nightdress. Pretty light sleeper back then as I had only just started trying to sleep in bra & panties, nowadays I struggle to wake up without the alarm going off first!

Anyway, lightly asleep when the phone rang, it was the alarm centre calling to say the burglar alarm at work had gone off and could I attend please. Not a "confirmed" breakin, so the police had not been called but I was required to attend. I stumbled out of bed, pulled some clothes on and dashed out the door to check what had set the alarm off. Got on site, unlocked and went in, looked around, there was no break in, either a bug had crossed a sensor or a notice or something had fallen off a wall passing through a beam triggering the alarm.

Reset everything, locked up and went home. Got in, went into my bedroom and got undressed to find that I was still wearing my bra, panties, smaller breastforms and nightdress! Took AGES to drop off to sleep that night!