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Most Daring Thing You Have Done Crossdressed?


Guest Jessie_Cd

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  • Michelle 2010

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Um, Donna Jean honey...That was supposed to be a trump card, not the lead card...

Now I'll have to go away and think of a good lie and come back... :doh1:

Michelle

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.

Flown in a combat zone in Vietnam while wearing a matching bra and panties under my flight suit.....

There ya go.....

Donna Jean

And it's Dee Jay for the win.

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I can't top Donna Jean, but I did wear panty hose under my business suit while working for the chief of police in the 1980's. :D

Carolyn Marie

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Was standing aroind smoking in my garden when my brother walked in, pretended to be drunk and told him we played 'swap poker' at the party i was at previos to this happening (o which i subsequentially had to come up with 'rules' for this fictitious game on the spot) itmight not be flying through a warzone but i still abot crapped it!

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Guest Naomi M

Well, Donna Jean just won the thread. :lol:

Outside of what I've already mentioned in my introductory post, the most daring thing I did was wear a bra to a meeting with a transfer counselor at my college. All in all it wasn't very daring and all went well until we finished and he gave me a pat on the back! I had a jacked and loose shirt but I still think he may have felt it. I seem to have the worse luck sometimes....

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Guest ~Brenda~

Flown in a combat zone in Vietnam while wearing a matching bra and panties under my flight suit.....

Holy Cow!!

Well, my story is a little more pedestrian than DJs :) Years ago, I used to get dressed up and do simple things like grocerie shopping, getting gas, running other errands. I remember the first time I went out dressed to run normal errands (my heart was pounding!!)

Doesn't come close to DJs story :)

Love

Brenda

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Guest kimberly c

Hi, went to a lingerie store in my full female attire,including breast forms,mingled with the sales clerks and two other

women who were shopping, bought some bras and panties, what a rush.

Love Kim

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Guest Julie T

Speechless - what can I say. I feel so plain and boring.

I guess it was getting stopped by a cop on the way home from a GLBT meeting, fully dressed, and I had left my drivers license in my wallet, at home. I knew I was going to jail, but the cop sighed, asked how far away I was from home [20 minutes] and said to me, get out of here. I was just at the edge of androgynous at that time, and to this day have no idea what he thought of me.

Julie

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Daring or stupid? no judgement please!

My first night out ever - dressed in a gown that still is the most beautiful piece of clothing I own. Driving with heels on - less than smooth. Then getting out to walk. On Seattle's uneven sidewalks in the dark. Way less than smooth! But had several blocks of practice. In a seedy part of town. Getting to the destination before anyone else arrived, sitting in a bar feeling overdressed and way visible. And knowing that my car was back down that dark and seedy street. Fortunately, the wine was good, the rest of the CD club showed up, and, aside from that uneasy walk in the dark, the rest of the night was grand!

Pretty much the same story any CD might have - routine after a while, but the adrenalin told me it was the most daring thing that I'd ever done!

Love, Meg

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.

Flown in a combat zone in Vietnam while wearing a matching bra and panties under my flight suit.....

There ya go.....

Donna Jean

Nyah, nyah!

I can actually beat DJ with this one!!!!

I was wearing a red and silver teddy, matching panties, and stockings under my fatigues when my platoon got ambushed the second time in Iraq. Goddess was I glad I didn't get hit. That would have been real awkward to explain!

Tada! Nuclear bomb... Trumped!!!!!

<3

Elena

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War stories in femme underclothing...what a drag... :)

I've had this strong urge to go to the beach with painted toenails but since this isn't Key West...

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

The weirdest thing I can contribute is physicals with a smooth bod.... (((yawn)))

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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

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

That happened to me when I had a seizure in 2002. Luckily the nurse left the room while I undressed. Had a physical a few weeks ago and didn't think about it beforehand. Until we got to the part when the Doc wanted to do the prostate check thing. But by that time I'd already told him I was trans and wanted hrt anyway so I didn't really care.

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Guest Julie T

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

Sally, Miss Pinky is a sweet little purse gun, but I retired her to my little summer purse when I got my bigger gun holster purse, and that gun is silver with black grips, thank you. [me smiling]

Julie

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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

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Guest Lacey Lynne

The 1970s? Eh, they were kind of cool. Actually, on looking back, they were pretty cool overall.

There's only ONE decade in my book, baby:

THE SOARING SIXTIES !!!

Time machine? Anybody got a time machine? Set that baby for about 1962 or so and let's boogie back for about 8 years or so!

Peace & Love :superman: Lacey Lynne

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Guest Michellewhois

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:

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      I so very much enjoy your posts. This one, though, hit home with me for many reasons. I was commissioned in the Army in '77, as well. Like you, I was not overly masculine in the way that many of our contemporaries were. I (still do) cried at weddings, pictures of puppies and babies, when I talked about bring proud of what my units accomplished and was never the Type A leader. In the end, it worked for me and I had a successful career.   This is, of course, your story not mine so I won't detail my struggle. It just took me much longer to understand what the underlying cause of my feelings was and even more to admit it. To act on it.    Thank you for sharing your story, Sally.
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      Post 6 “The Military Career Years” In 1977 I joined the Army and went to flight school to become a helicopter pilot.  To fly for the military had been a childhood dream and when the opportunity arose, I took advantage of it, despite knowing I would have to carefully control my crossdressing activity.  At the time, military aviation was male dominated and a haven for Type A personalities and excessive testosterone.  I had always been competitive but my personality was not typically Type A.  And while I could never be considered effeminate, I wasn’t overtly masculine either.  Consequently, I had little trouble hiding the part of my personality that leaned towards the feminine side.    However, serving in the Army limited my opportunities for feminine self-expression.  During this period, I learned that being unable to express my feminine nature regularly, led to frustration and unhappiness.  I managed these feelings by crossdressing and underdressing whenever I could.  Underdressing has never been very fulfilling for me, but while I was in the Army it was a coping mechanism.  I only cross-dressed in private and occasionally my wife would take me out for a late-night drive.  Those drives were still quite private, but being out of the house was clearly therapeutic.    I told myself I was coping, but when it became apparent the Army was going to be a career, the occasional and closeted feminine expression was clearly inadequate.  I needed more girl time and I wanted to share my feminine side with the rest of the world, so the frustration and unhappiness grew.  Despite my feelings regarding feminine self-expression, I loved flying, so I wasn’t willing to give up my military career.  Consequently, I resigned myself to the fact that the female half of my personality needed to take a back seat, and what helped me through, was dreaming of military retirement, and finally having the ability to let Sally blossom.   About Sally. Ironically, she was born while I was still serving.  It was Halloween and my wife and I were hosting a unit party.  I looked upon the occasion as the perfect excuse to dress like a girl.  After a little trepidation, my wife agreed I should take advantage of the opportunity.  Back then, my transformations were not very good, but with my wife’s help, my Halloween costume looked quite authentic.  Originally, my wife suggested that my presentation should be caricature to prevent anyone from seeing through my costume.  But that didn’t appeal to me at all.  I wanted to look as feminine and ladylike as I could.   To my wife’s and my amazement, my costume was the hit of the party.  In fact, later in the evening, my unit buddies decided they wanted to take me out drinking and before either me or my wife could protest, I was whisked away and taken to one of our favorite watering holes.  Terrified at first, I had an amazing time, we all did.  But on Monday morning, when I came to work, I learned that I had a new nickname; it was Sally, and for the duration of that tour, that’s what I was called.  Well, when it came time for me to choose a feminine name, there weren’t any other choices.  Sally it was, and to this day I adore the name, and thank my pilot buddies for choosing it.   And this brings me to my last assignment before retiring.  I was teaching military science in an Army ROTC program at Mercer University in Macon, Georgia.  I had been a member of TRIESS (a nationwide crossdressing support group).  I wasn’t really an active participant but when we moved to Georgia, I learned there was a local chapter in Atlanta.  I reached out to the membership chair person, and joined.   Because the chapter meetings took place in Atlanta, a trans friendly city, and because Atlanta was so far from Macon and any of my military connections, I felt it would be safe to let my feminine hair down.  The monthly meetings took place in the Westin Hotel and Conference Center in Buckhead, an upscale northern Atlanta suburb, and the hotel itself was 4-star.  The meetings were weekend affairs with lots of great activities that allowed me to express myself in a public setting for the first time.  It was during this time, that Sally began to blossom.   I have the fondest memories of Sigma Epsilon (the name of our chapter in Atlanta).  Because the hotel was also a conference center, there was always some big event, and in many cases, there were several.  One weekend there was a nail technician conference that culminated in a contest on Saturday evening.  When the organizers learned there was a huge group of crossdressers staying at the hotel, they reached out to us looking for manicure volunteers.  I volunteered and got a beautiful set of long red fingernails that I wore for the duration of the weekend.   During another of our meeting weekends, there was a huge military wedding taking place, and imagine what we were all thinking when we learned it was a Marine wedding.  Our entire group was on edge worrying we might have to keep a low profile.  It turned out to be one of the most memorable weekends I would experience there.  First off, the Marines were all perfect gentlemen.  On Friday night and throughout the day on Saturday before the wedding, we rubbed elbows with most of them and their wives in and around the hotel, and at the hotel bar.  In fact, we got along so well the bride invited us to the reception.  Somewhere, there is a picture of me with a handsomely dressed Marine draped on each of my arms, standing in the lobby of the hotel.  Sadly, I never got a copy of it because the woman who took the picture used a film camera (yes, they actually took picture that way in ancient times).    My two-years with Sigma Epsilon was the perfect transition.  I went from being fully closeted to being mostly out.  I enhanced my feminine presentation and significantly reduced my social anxiety.  It also signified the end of one life and the beginning of another.  I had a great career and never regretted serving, but I was ready to shed the restrictions 20-years of Army service had imposed on my feminine self-expression.  My new life, Sally’s life, was about to begin, and with it I would begin to fully spread a new set of wings, this time feminine wings.    Hugs, Sally
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