Jump to content
  • Welcome to the TransPulse Forums!

    We offer a safe, inclusive community for transgender and gender non-conforming folks, as well as their loved ones, to find support and information.  Join today!

Most Daring Thing You Have Done Crossdressed?


Guest Jessie_Cd

Recommended Posts

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

Link to comment
  • Replies 85
  • Created
  • Last Reply

Top Posters In This Topic

  • Michelle 2010

    4

  • Sally

    2

  • Petra Jane

    1

  • MackenzieB

    1

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 :lol:

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.

Link to comment
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: :lol: :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

Link to comment
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

Link to comment
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: :lol: :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

Link to comment
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!

Link to comment
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

Link to comment

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

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

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... :banghead:

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

Michelle

Link to comment
Guest Michellewhois

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

Michelle

:D 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: :lol: :lol:

Link to comment

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

Link to comment
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.

Link to comment
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.

Link to comment
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.

Link to comment
  • 3 weeks later...
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

Link to comment

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.

Link to comment

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.

Link to comment
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

Link to comment
  • 1 month later...
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!

Link to comment

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,

Link to comment

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...

Link to comment
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 :thumbsup:

Link to comment
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

Link to comment
  • Root Admin

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! :D

Link to comment

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
  • Who's Online   6 Members, 0 Anonymous, 98 Guests (See full list)

    • Chloe Summer
    • Ashley0616
    • Jet McCartney
    • MaryEllen
    • missyjo
    • awkward-yet-sweet
  • Recently Browsing   0 members

    • No registered users viewing this page.

  • Forum Statistics

    • Total Topics
      80.7k
    • Total Posts
      768.3k
  • Member Statistics

    • Total Members
      12,024
    • Most Online
      8,356

    JamesyGreen
    Newest Member
    JamesyGreen
    Joined
  • Today's Birthdays

    1. Dillon
      Dillon
    2. Kaylee888
      Kaylee888
    3. lily100
      lily100
      (39 years old)
    4. Luce
      Luce
      (44 years old)
    5. Luke.S
      Luke.S
  • Posts

    • Ashley0616
      The trans community won't be good under Trump at all. Biden is the one who has done more for the trans community than any other presidents. Last time Trump was in office he was at an LGBTQ rally and his support went quickly away from us because the majority of the voters are anti trans. He is going to get rid of our rights and also come after the rest of LGBTQ.  I don't know where you heard we would be better under Trump.    Trump unveils sweeping attack on trans rights ahead of 2024 (axios.com)   Trump Promises to Go After Trans People if Re-Elected (vice.com)   Trump promises to ban transgender women from sports if re-elected (nbcnews.com)
    • Sally Stone
      Post 7 “The Pittsburgh Years” When I retired from the Army, we moved to Pittsburgh, Pennsylvania because I had been hired by US Airways to work in their flight training department.  The transition to civilian life was a bit of an adjustment, but I never really looked back.  At the same time, I was excited at the prospect of having more Sally time. But with work and two teenage boys in the house, getting to be Sally was a challenge.    The biggest issue in this regard were my sons, as they didn’t know about my feminine side.  My wife and I discussed, in great detail, whether or not to tell them.  If they had known about Sally, it would have been much easier to actually be Sally when I wanted to.  But I still didn’t know exactly where my transgender journey was going to take me, and this uncertainty was the primary reason my wife and I decided it wasn’t the right time to tell them about Sally.  Except for the convenience it would afford me, we didn’t think it was fair to burdened them with such a sensitive family secret if it wasn’t absolutely necessary.  If at some point things changed and it looked like I might be heading towards transition, my wife and I agreed we would revisit our decision.   Despite having to tiptoe around the boys I was able, with my wife often running interference for me, to significantly increase my girl time.  The nature of my variable work schedule meant that often days off occurred during the week when the boys were in school, and on those days, I took full advantage of the time.  Additionally, I had discovered a new trans friend through a local support group, and my wife, ever and always accommodating, ensured I had time for outings with my new friend.    Willa, my new friend, quickly became my best friend, and after only a short time, she and my wife became quite close as well.  With Willa’s help, I would soon discover that Pittsburgh was a very trans friendly city.  Together, she and I made the town our own.  We attended the theater, the symphony, we went out to dinner regularly, and I think we visited every museum in the city.  With Willa’s support and friendship, I was actually becoming quite the girl about town.    Willa and I had a lot in common.  We loved to shop, we had similar feminine styles, and we had similar views and feelings about being trans.  In fact, our frequent and deep discussions about transgender issues helped me begin to understand my transgender nature.  Having Willa as a springboard for all topics transgender, was probably as effective as regularly visiting a therapist.  I would never discount anyone’s desire to seek professional help, but having an unbiased confidant, can also be an effective method for self-discovery.    Exploring the city as Sally and spending time with Willa was instrumental in helping me understand my transgender nature, and would begin shaping my transgender objective.  My feelings about the kind of girl I was and where I wanted to go began to solidify.  Being out and socializing as Sally in a big city like Pittsburgh, taught me I could express my femininity without issue.  I honestly felt confident I could live my life as a woman; however, remaining completely objective, I just couldn’t see giving up the life I’d built as a man.   At that time, I was being heavily influenced by the concept of the gender binary, which had me thinking I had to choose between being a man or being a woman.  It was Willa who reminded me there were no rules requiring gender identity to be binary.  During one of our deep discussions, she posited the idea of enjoying both genders, something she was doing, and a concept that made a lot of sense to me.  I was already living the life of a part-time woman, so I simply started paying more attention to how that was making me feel.    One characteristic that was dominating my feminine self-expression (and it continues to this day) was that when I was Sally, I was “all in.”  When I became Sally, it was such a complete transformation that I truly felt like a woman.  The feeling was powerful, and if I had to describe it another way, I’d say it was akin to an actor, so into the part, they actually become the character they are portraying.  That was me, and I discovered that this level of depth was extremely fulfilling, and that feeling tended to last long after transitioning back to my male persona.  Part-time womanhood it seemed, was actually working for me.    Eventually, a job change forced me to move away from Pittsburgh, but the enlightenment I experienced while living there has shaped the nature of my bi-gender personality to this day.  Even after leaving, Willa and I remained the best of friends.  We had many more adventures, some of which I will detail in later posts.  Sadly, Willa passed away two-years ago after contracting a prolonged illness.  Her loss was hard to take and I miss her dearly.  However, I have so many fond memories of our times together, and because her support helped shape me, she lives on in my heart.   Hugs,   Sally
    • missyjo
      thank you dear. I'm constantly working at adjusting n writing off other people's judgment or input.   thank you n good luck
    • Abigail Genevieve
      Them's fighting words, but I intend to discuss this respectfully, calmly and so forth, in accordance with the forum rules.   Considering the one issue below in isolation:   There is a political calculus that trans folk may be better off under Trump than under Biden.  The argument goes that Biden has created such a backlash by moving so far to the left that red states, in particular, are reacting with a swarm of laws that negatively impact trans folk.  Some of his actions strike many people as clumsily forcing unwanted regulation on people, and some of his appointments, such as the luggage stealing bigender individual, have not helped advance trans folk but rather the reverse.  In a second term Biden would make things worse for trans folk because of the backlash and resentment his policies would create.    Trump likely would have negative impacts to trans folk, as he did in his first term with respect to the military, so it is a set of tradeoffs as to which is worse.   Thoughts?
    • Abigail Genevieve
      Can you dress androgynously? 
    • Ashley0616
    • Abigail Genevieve
      There are trans folk who pass better than some cis people.  People usually aren't on the lookout for those who are cross dressed.  As long as there are no multiple screaming signals and you don't draw attention to yourself you can probably pass better than you think. For example, if you walk into a bank in heels, however, and you DON'T know how to walk in heels, you will attract the attention of a security guard, especially if you are acting nervous. If you wear flats and just go to the bank and do your business like anyone else, it is likely no one will notice, except that there was a customer who was taller than most women are, but then there are tall women, and tall, broad shouldered woman.  I made the mistake years ago of thinking I had outed such, and knew she was a he.  Later I learned she had five kids, and her husband was bigger than she was.  Ooops.
    • Abigail Genevieve
      I don't know much about CNAs.  They report to an RN, right?  Can you somehow bring this up to the RN in a way that does not get your CNA mad at you? I'm not saying you should, but maybe that is a good course of action.
    • Abigail Genevieve
      This is the thing.  A month ago tomorrow is when I stopped wearing m clothing.  Today I feel great.  I do not have dysphoria when I am dressed as and I move as a woman.  I was just thinking about that because I was wondering if I would or will get hit with a wave of "you don't have dysphoria so you might as well dress like a guy. Less hassle with your wife."  Not that she is aware, to my knowledge, that these androgynous clothes are women's.  No desire to "flip", no feeling of need to, just happy identifying as female.  Speaking, in my deep guy voice, with female voice patterns, doing the feminine gestures that come naturally and without exaggeration and at peace.
    • Birdie
      Yes, my brother was born lactating due to absorbing hormones from my mum.    Of course she isn't a nurse, she is a CNA. She should however still have general medical knowledge.
    • Abigail Genevieve
      I agree.  But sometimes unethical conduct must still be legal, because the cure would be worse than the disease.  One problem we have today with the internet is the trolls can gang up on someone and destroy them - we see the with school bullying as well.   He was in the Southern Baptist Convention, and maybe he should have moved his church over to say the American Baptists, who might have been able to help him. A Southern Baptist pastor is king in his church, peerless, which means he could not have gone for help in his church.  And he could not have gone for help from any other pastor in the SBC because they likely affirm the SBC statements on these matters.  I think he was stuck.    I read this when it came out in the news.  Very sad situation.  
    • Carolyn Marie
      One organization that I know of that is dedicated to assisting LGBT seniors is SAGE.  They advocate for, and have services for, all LGBT folks, not just trans folk.  You can find their website Here.  I am not sure what, if anything, they have in terms of financial assistance.  I'll let you know if I find anything else.   Carolyn Marie
    • Davie
    • VickySGV
      This was an angle that I was very suspicious of as well, and may be the hook on which the settlement was hung.      Not at all strange especially if they had former patients who moved there that still owed money on their bills or they were buying hospital supplies from a Texas corporation. They may have business licenses in other states as well.  Small loss, but saxeT shot itself in the foot there since the license was a source of income to the state. 
    • RaineOnYourParade
      Nah it's fine, I'm past the point of really blaming them most of the time. I've gotten used to it, and they could be a whole lot worse.   I'm glad you have a good place, though <3
  • Upcoming Events

Contact TransPulse

TransPulse can be contacted in the following ways:

Email: Click Here.

To report an error on this page.

Legal

Your use of this site is subject to the following rules and policies, whether you have read them or not.

Terms of Use
Privacy Policy
DMCA Policy
Community Rules

Hosting

Upstream hosting for TransPulse provided by QnEZ.

Sponsorship

Special consideration for TransPulse is kindly provided by The Breast Form Store.
×
×
  • Create New...