Your Most Embarrassing Moment While Dressed

[brassieres]

For me it was when I was a young. I told a female about my desire to crossdress. She put make up and perfume on me. Then she went and got both her and my brother and told them what she had done, and they all laughed at me. I was very embarrassed!

[BethCD]

When I was around 10 or 11 my best friend and I were goofing around at his house up in his shared bedroom ( with his sister).
I already had an interest in cd'ing......... we ended up trying on a few things of hers. For him it was a bored day of diversion. For me it was waaaaaay cool.
A few days later we were at my house and he said, what do you want to do???
I said quietly, lets go try on your sister's dresses....
He repeated it to the kids nearby....:eek:
I denied it but, was out to at least him, only if nobody else believed it.
Nothing came of it, but I was worried for years until he moved out of state.
Beth

[KristinSkye]

For me it was when I was a young. I told a female about my desire to crossdress. She put make up and perfume on me. Then she went and got both her and my brother and told them what she had done, and they all laughed at me. I was very embarrassed!

Ouch...that is rough :/ Sounds like you got over it though :)

I haven't had any embarrassing moments yet...primarily because my CD'ing is such a secret though.

[Erin Li]

Probably my most embarrassing moment is not singular, but plural. And it's not when I'm dressed, but when I've just finished dressing. It's when I'm out at dinner or with friends, and my SO tells me I didn't do a good enough job removing my makeup. I feel my face flush instantly!

[sherri52]

During gym class in HS I was forced to strip while I was wearing my sisters side zippered pants. I got out of gym but not the shower. If I wasn't know for being crazy it could have been much worse. Most people were afraid to say something. I mellowed out a little just a little and after 30 yrs in the post office people are still afraid I'll go postal. Can't understand people. lol:heehee:

[Alice Torn]

In an 18 hr period, got followed, stop by a cop, got shouted expletives by guys passing in a car, got OMG'd at by teenagers, and had a man tell his kids not to look, as I gave his car a jump start. It was my very first full day out dressed!

[Susana_93]

I was caught by my mom twice as a child :eek:
The first time was so embarrasing for me that I said I would never ever crossdress again :brolleyes:

[Rachel Morley]

I haven't had an embarrassing moment when dressed yet ... not in the sense of being dressed now that I acknowledge that I am a CDer.

My moment was like yours when I was younger. I swear this is true. I was 16 years old and I was at my girlfriend's house one evening and we were in her room watching TV and just hanging out. I can;t exactly remember why but she thought it would be fun for me to try on some of her clothes. I made up some kind of "oh alright .. if you must" type of remark and let her. She dressed me in one of her bras and a rather feminine blouse and then put some makeup on me. Just after she was done her older sister came into the room without knocking. She took one look at me and started laughing and then said in a loud voice "why is he wearing my blouse?"my girlfriend said to her sister "its not your blouse it's my blouse, you gave it to me, and anyway so what? .. I want him to wear a blouse!" I went really red and felt all embarrassed. Her sister said she could also see that I had makeup on too and that she was going to tell their Mom. I nearly freaked out! :o:o

[flatlander_48]

Almost an embarrassing moment, but not quite:

A friend of my wife's came to visit this morning, but my wife forgot to tell me. When the woman arrived, I was in a turtleneck and overalls, but completely fem underneath. Ordinarily this wouldn't have been a problem, but with the particular sports bra and forms that I wore, there was a fair amount of projection. However, since the turtleneck was black as were the bib overalls, it was pretty stealthy. Stealthy until she decided to hug me!?!? Fortunately I was on my way to the washing machine and had an armful of dirty clothes. Therefore, we couldn't really get that close. Same thing happened again as I was leaving to go to the grocery store. We had to have a Good Bye hug. Again fortunately, I had my coat on and there was some furniture in the way so we still couldn't get that close.

Gee, really surprising that fake boobs were so magnetic! Who knew?!?!

[marny]

Not so much embarrasing but in regard to flatlanders comments, I have had many women hug me while I'm wearing a bra and occasionally with forms. For the most part I know they suspect and ther feeling for it. I have had two ask ' Are you wearing a bra?' and my answer both times was ' You caught me sweetie!' OH! And for the embarrasing part, I have had a couple of men I know unexpectedly pat me on the back and give me some pretty funny looks. Definetly busted.

[Teri Jean]

Okay where do I start...................................this could get to be volumes. How about this morning? I'm sitting in the living room having a cup of coffee and reading the paper. I'm in my nighty and a bathrobe. Normal morning before getting ready for work but this morning I had the day off so it was an hour later than normal.

Now my daughter had called the day before and asked for a short term loan and I had it in an envelope for her. Now here I am and she knows I am 24-7 but the nighty was something she had not seen or wanted to, so when the door to the kitchen opened I got up to see who was coming in, it was locked. Let's say she now has seen her dad in a short satin nighty and bathrobe.

You know those priceless jokes/moments, well her smile and my blushing had to be quite a sight. Ooooops. LOL.

Teri

[Lisia]

In an 18 hr period, got followed, stop by a cop, got shouted expletives by guys passing in a car, got OMG'd at by teenagers, and had a man tell his kids not to look, as I gave his car a jump start. It was my very first full day out dressed!

Now this sounds like a big and crazy first day out! I for one would love to hear that story in detail! :daydreaming:

I guess for me, recently at least, it would be when I was walking around my neighborhood late one night a few years ago. I would usually just walk around the residential streets around my house, running into very few people and they rarely had an interest in chatting me up. But this one night, after a couple of drinks and a little bit too long in the fog, I decided to go around the corner where there was a much busier street(like 6 lanes). I walked in front of a convenience store, and continued across a strip mall parking lot on my way to the sidewalk to continue into the neighborhood.

About half way across the parking lot I though I was home free... I hear "excuse me ma'am"... there was a bar nearby and I recognized the person speaking as someone I had seen leave the bar and drive across the lot, passing me on the way to the store. I sped up just a little and didn't look back, hoping he would give up. I should have known better, since he had already walked 50 or 60 yards after he parked just to get close enough to be within earshot of me! He persisted drunkenly saying "excuse me ma'am" so I decided he would not give up.

I knew that he was drunk, I could hear it in his voice, and after turning around to face him I saw by how he was walking that he should not have even been driving, at all. Knowing that, and that I had a knife on me :heehee: I just turned around, and in my best deep guy voice said "yeah, what you want?"

Oh, s**t you're a dude! and he turned around very quickly, but not without an apology!
I never did find out what he wanted, I am going to assume he was looking for "directions" somewhere. :battingeyelashes:

I was not too embarrassed by that, it was more humorous than anything, but then on the way walking back home, not 3 minutes later I had a cop stop in the middle of the busy six lane road, turn his lights on to block the lane, and pull me over(I was walking!!).

He asked me what I was doing out and I said I was just taking a walk. As he asked me for my ID he obviously realized what was up so he asked me what I was doing dressed as I was. I responded that doing so relaxes me, and makes me feel better about myself.

He replied, "Well, I can't argue with that ma'am, just be careful out here. Some people might not understand." :eek: Wow! Really?! I just couldn't believe his reaction, given that the town I was in had cops that had a well known reputation for being VERY redneck and callous. Some real southern "hard-asses" lol I was very surprised, and also a little embarrassed as I was getting grilled by the police on a sidewalk next to a busy street with a police car blocking lanes!

I have since resumed going out, and am getting more adventurous as I work more on my look. Every time I get a little nervous I remember that night and think "what is the worst that is likely to happen?" :heehee:

Lisia

-edit: wow, I really did start typing this in the intentions of telling a short little story! I guess I type like I talk!

[trannie T]

I've never had any really bad experiences while dressed, several years ago though, I had a bad experience two days after halloween. I had gone out dressed on Halloween and was off the next day. When I went back to work in the middle of the morning one of my employees stared at me laughed and said to everybody in the office, "He's wearing makeup!" I stammered a. "No," and quickly went to the bathroom and scrubbed my face. Nothing more was ever said about the incident and I became a lot more careful when I was removing my makeup.

[Bailey_in_Mansfield]

For me it would have been Halloween 2008 when I went to work as Sarah Palin in order to win my work's costume contest for $100. On my way in, I passed by two little boys, each about five or six years old. One of them turned to the other and said "Look, that's Sarah Palin!" I was pleased at first that the little kids recognized who I was supposed to be, and that I actually passed for being Palin herself.

Then the kid continued, "She's a lot uglier in person than I imagined though."

Open palm, insert face.

[Desiree2bababe]

Had to be when I was walking the streets of Charlotte one Sunday afternoon......a cop slowed and checked me out. I got scared and ran for no reason. They caught me, slung me against their car, busting my water balloon titties. Charged me with failing to head an officer. Spent 3 days in lockup, parents rescued me, walked out in jail pants that were falling down and Mom saw her girdle I was wearing. Very embarrasing.......

[Elsa von Spielburg]

I guess it was the first time I went out in public en femme, to the RHPS, my GF's friend that went with us couldn't stop snickering seeing me in wig, dress, walk in heels (admittedly my first time), etc. Like my confidence needed any help destroying itself.

[KerryLynn]

For me it has to be when i worked at a movie theater. We had white dress shirts and a red vest. Went to the bar after work forgetting that i had a black bra on. Bartender said "You know if your going to wear a white shirt you shouldnt wear a black bra. I wanted to curl up under my stool. But i shruged and said my white one was in the laundry. Two others in the bar laughed at the look the bartender gave me. Oh Same bar following holloween. Dressed up looking damned hot lol one guy asked if the breasts were real and wanted to touch them. God i miss that bra.

[JaytoJillian]

routine police stop when I handed the cop my license and he took a dbl take

[Jilmac]

It happened when I was around 12 (still in the experimental stage). I was playing darts with my friend Jack in his basement when I noticed a basket of clean folded laundry which contained several pairs of his mom's panties. I picked the prettiest pair (pink with white lace ruffles on the butt) and told Jack that I had to use the bathroom upstairs. I must have been up there longer than I thought because Jack came up looking for me and opened the bathroom door and caught me modeling the panties in the full length bathroom mirror :eek: He teased me about it for a long time afterward but never told his mom or anybody else.

[aggi123]

other than getting caught when I was younger, this happened the other day. I was up late and everyone asleep. I figured what the heck! I'll get dressed in a tank top, and pajama pants and play video games in my room. My brother came home at like 3am and immediately came in my room (he knows I dress). He looked at me and said, "is that a bra?". I replied yes and he told me he brought his boyfriend over to give me the heads up. He'd never really seen me dressed up before in person, just the pictures I've shown him. First time anyone has ever seen me dressed.

[Christina Horton]

Well that's a hard question for me cuz I have not nor can I be embarrassed.....Well in drab anyway. The closest time I can to be embarrassed was just before Christmas 08 , I was out Christmas shopping dressed and had on a new white skirt I had bought at Sam club. It has no tie just a stretch waist band. I was walking in the biggest and at that time the most busiest mall around like I all ways shop in. While I was walking the skirt started to slip down I did not feel it drop until it was below my panties. I grabbed for it caught it and put it back into place.

Now like I said MIKE can't be embarrassed but I now think that Christina just might be cuz, walking away looking around I thought " wow I think I might have been embarrassed for the first time ever ." I gotta say it was a neat feeling to almost be, I might just try to embarrass my fem-side just to see what all the fear is all about.

But that was the only time and the closest I have ever come to being red in the face.

[windycissy]

There have been many, but nothing tops the Halloween I went to a costume party in my girlcat costume, and I must say it was pretty cute, I turned a lot of heads and got a lot of smiles on the way through the lobby of my hotel:

http://im1.shutterfly.com/media/47b9cc29b3127ccef88535f4e38300000030O08IatWLlw0aA9 vPgw/cC/f%3D0/ps%3D50/r%3D0/rx%3D550/ry%3D400/

The party was okay, but I made the mistake of drinking a couple glasses of incredibly cheap box wine and some bad munchies, and my costume was getting uncomfortable in the stifling apartment so I left early and started to drive back to my hotel. I started feeling worse and worse and about five miles before I got back to my hotel I threw up all over myself and the car - don't know how I kept it on the freeway! Fortunately, I was wearing a long flowing skirt that caught most of it, but I was a total mess and the car too. Worse, I had valeted it, and had to drop it off at the front entrance to my hotel, covered with puke!

I pulled over just short of the hotel and analyzed the situation, no good options. So I used the arm of my sweater to clean up the car as best I could, saw that the entrance looked quiet, pulled up and hopped out of the car before I lost my nerve. The valet jockey just smiled at my costume and said "Meow" although I'm sure the smell knocked him out when he got in...I put on my best smile and waltzed through the lobby, "Oh look at the girl in the cat costume, how clever she covered herself with goulish yuck for Halloween" I imagined people thinking as I made a beeline for the elevator, thank God nobody was on it and I rode alone back to my suite and staggered into my room. Several New Years Resolutions have been made to avoid a sequel.

[kellyanne]

For me it was when I was a young. I told a female about my desire to crossdress. She put make up and perfume on me. Then she went and got both her and my brother and told them what she had done, and they all laughed at me. I was very embarrassed!
I overnighted with a pal in a motel room and had to explain why my chest, torso and legs were fully shaved - I said I was swimming - he was noy buying.

[Paige Valtieri]

I haven't been caught in the act, but my parents have found my stash of female clothes a couple of times.(the first time they didn't know they were mine, but the second time:o) I didn't think my face could have turned any redder until they asked me if I was gay or something. Needless to say I wasn't allowed to go to any of my guy friends' houses for a long time(of course I still did any way) and no, I'm not gay. But that doesn't mean I haven't been tempted to go bi before.:o

[JulieC]

In an 18 hr period, got followed, stop by a cop, got shouted expletives by guys passing in a car, got OMG'd at by teenagers, and had a man tell his kids not to look, as I gave his car a jump start. It was my very first full day out dressed!

This is one of the reasons why I don't have much desire to go out in public view while dressed. I do go out, to get out of the cage so to speak of home while dressed, but not for public consumption (except to support meetings).

It's not that I'm afraid or overly self conscious of what people can say. I don't really care what they say in so far as it has no effect on me. It's just the negativity of being viewed as a monster of some kind. I don't need that.

[desi88]

walking home late at night in my home town enfem and two guys pll up and say Hi Cutie... i knew them both but not sure if they new it was me... i turned away and ducked down another street...whew!!!.. my sisters also would ask me if i knew where their underwear was... duh!!!! ask mom!!!

[kimmy p]

For me it was amusement more than true embarrassment. One of the first things that my future mother in law ever said to me was what pretty eyes I had, and how pretty of a girl I would have made (If only she knew). After a couple of months of this I finally told her that I would dress up for her on Halloween (a month away). :D
Well Halloween came and with my wife's help I dressed up and headed out to my in-laws, 45 minutes away, with no spare clothes. On the way there my wife casually mentions that her nephew and his family will be visiting from southern Indiana. No problem except that I had never met him, and did I mention that he was Mennonite? :eek: As we pulled into the driveway at the in-laws farm it looked very dark. My wife looks at me and says "ummmm... Mom said that they might be visiting the neighbors tonight". :bonk: In the country Neighbors is a very relative term. I reluctantly drove the 5-6 miles to the neighbors and as I arrived there I realized that they were old order Amish! :bonk::bonk: I tried to stay in the car, but you wouldn't believe how persistent a 102 pound little old lady can be, and I found myself being introduced to the Amish family and her son in law. Which created quite a few really questioning looks. (I guess I passed). :clap: My father in law was having a good time with it, and I nearly jumped through the roof when I unexpectedly felt his hand slid up my skirt. :confused2:
After a short time my wife and I left and headed to the party that we had planned on attending. That went well. I was asked by "friends" if I planned on standing or sitting to go to the bathroom, and I heard one guy yell "Sh!t! I thought that was a girl" (Man I didn't even have a wig. How was I doing so well)? :D
We left the party a couple of hours later and my wife decided that she wanted a couple of movies. So we stop at the video store, which happens to be on the busiest cruising strip for miles, and of course she won't let me stay in the car.:devil: I go into the store with her and NOBODY IS EVEN LOOKING TWICE AT ME! :o Cool! At least until we have to pay for the movies and I have to hand the manager my drivers license for the rental. :doh:I have done business here for years, he's seen me before. But he looks down at my license, up at me, down at my license, up at me. Several times. Finally as he's looking at me I just close my eyes and nod in confirmation. Without another word we get our movies and leave. Was it a bit embarrassing? Yes, but also fun. Hope you enjoyed my story.:tongueout

[angelinamillar]

When I was 19 I crashed my motorbike and woke up in hospital witha broken leg, dislocated shoulder, broken right thump and a bad concusion. The other thing I was was naked except for one of the annoyed arse out hospital robes. Then the realisation set in that I knew when I crashed I was wearing a pair of sheer tights, A black thong bodysuit, Epilated well pretty much everywhere and painted toenails. Nothing was said by the staff but I just always knew that quite a few people out there saw exactly what I was wearing or were told. A few years after that I would over hear comments or rumours, was pretty embarrassing. Still don'y stop me wearing the same, ecspecially at the moment with all this cold weather.

Hugs,

Angelina x

[CDTracey2U]

My last time out...about 4 years ago, the wife and I walked into the local Les/CD bar, we saw one person we knew but thought we could avoid....until we turned around and there were 10 other people we knew...some bi girls, but none knew of Tracey. Kind of funny, one of the guys asked where I was...LOL, needless to say after 30 very uncomfortable minutes, the bar tender let us out the back door. Hopefully soon I will muster the nerve to head out again - man! we went to that bar almost every weekend for a couple years without incident.

Tracey

[natasha_laure]

I've never been caught dressed, but a few years ago a close friend of mine noticed my clear nail polish when I was round at his house and asked about it.

That led to my first outing to a friend in a very unplanned, blurted out way....at the time it was excruciatingly embarassing but he was cool about it.

[sfwarbonnet]

A few years ago I wore clear nail polish to a business lunch with a Professor from U of Washington in Seattle. I was nervous when I noticed it; I'm sure he did too but he didn't say anything.

[lycra shimmer]

when i was in college i used to work nights as a janitor in a small building where i was the only one, so i used to dress a lot while i did my cleaning. i was always very careful to put my clothes away but once i left a pair of really cute but bright pink lace panties in the janitor's closet! the next day i came in and one of the ladies who rented space in the building smiled and said,'Those are darling panties--you wear them anytime you want, hon!" i was embarassed but then i was just overwhelmed with relief for being "outed". i felt totally liberated and it really helped me come out as a crossdresser

[EnglishRose]

Mine will be in about an hour (discovery by mother-in-law) if I don't take off this cheongsam and the rest. I don't want to, though. :sad:

[sissystephanie]

I don't usually embarrass easily, but this time I did! It happened a few years ago when I was fully dressed, but as usual no wig or makeup. I had on a short black leather skirt and bright red satin panties underneath. I stopped at a gas station to fill up. As I stepped out of the car, my skirt (which had a hook and eye closure on the side along with a zipper) came completely apart at the side and fell to my ankles. There I was, standing alongside my car, wearing bright red satin panties and a tank top! I grabbed up the skirt, jumped into my car and drove home to change!! Nobody said anything if they did see me, but it was embarrassing!!

[billiedresses]

was 14 was druged by my fathers boss whom was "MY BIG BROTHER" he dressed me took pics then made me his little gurl . for 2 years 2 3 times a month I spent weekends at his house was very scared he would show pics it affected me greatly but as it turns out now I want to be a gurl go figure! :o :):battingeyelashes:

[danielle.cd]

well i cought myself after the fact: i got dressed and did my makeup and even painted my nails this time and put my new wig that just looked beautiful on me and sat down wondreing what to do

well we needed some toiletries and some other things so i figured ill go a couple of block to meijers and get it what better time its almost midnight and no one will be shopping, i was right and i work up the courage to finally go to a public spot in heels and stuff, i gott every thing i needed saw two workers that didnt even look at me and went to the check out, on my way this old lady worker just stared at me for like two minutes but didnt say anything to me, i made it home going yes that felt great and ill have to try it again some time. i went to the bathroom and as i was coming out i noticed in the mirror that i had missed about a 1 inch patch when i shaved earlier on my neck/ jaw area and you could see plain as day black hair long enough to know that it was beard growth i felt like and ediot and havent went any where dressed since

[thechic]

My Embarrassing moment was new years day had a flat tire, stopped and got out the car,a cop car passing turns around and pulls up behind me and offers help i reply in my normal voice.
then get home to my mothers after the breath test and get greated by may sister and partner.now my lifes and open book.:doh:

[Xenia]

Back in the late '90s, I had a group of gay friends I hung out with a lot. (I didn't mind being the "token straight guy" at their parties, seeing as how they were a lot more fun than most of my straight friends at the time.) One Halloween, a bunch of them decided they all wanted to dress in drag, and asked if I wanted to join them. You can probably guess my response.

So I found myself a cheap dress and a pair of stilettos, and a couple of the guys who were amateur drag performers had all kinds of fun making me up. We all headed off to a big party downtown (the Henri David ball, for anyone in the Philly area). I had a great time, despite being, by any reasonable measure and by a very comfortable margin, the ugliest drag queen in the ballroom.

Of course, that's not the embarrassing part. A girl I'd just started dating had earlier asked me if I wanted to come to her friend Terry's Halloween party. I'd told her I was otherwise committed, but that I'd try to stop by later in the evening.....without telling her about my costume (I figured it'd be a neat surprise, and a test of how open-minded she was).

So, after we were all partied out downtown, my friend Bob and I headed to Terry's place. Bob, feeling a little less brazen than I, was not in costume (party pooper!). We found the address, and as I sashayed into the apartment in my sequin gown, five-inch heels, and faux-diamond tiara, I learned three things:

First, that the girl I was supposed to meet had been feeling sick and had left hours before.

Second, that Terry--the only other person there that I'd ever met before--was passed out drunk upstairs.

Third, that, despite it being a freaking Halloween party fer chrissakes, I was the only one in the entire place wearing any kind of costume.

It was slightly awkward.

[Renee_E]

When I got pulled over at age 17 driving (without a licence) wearing my Mother's shift, panties and bra.

[UASIANGAL]

Wow, these are amusing stories! Sorry, I haven't any.... just a few close calls. Now if there was a thread like " Almost Got Caught" or "Nearly A Heartattack being Outted".... I'd have a few stories to tell!

Kudos to you survivors!

[tricia_uktv]

There have been a number but how about the most recent. I'd just bought my new wig and was walking around town in it with much pride. I could tell it made me more feminine and passable so I was really strutting my stuff.

Anyway, slap-bang in the middle of Manchester I was entering the Arch to Piccadilly Gardens. On a not particularly windy day a huge gust of wind appeared and sent my wig skipping back from where I had come. It was if someone up there knew what was going on and had it in for me. I turned around and inelgantly tried to catch up with it my three inch heels. It travelled only about ten yards but it seemed like half a mile. I eventually caught up with it and put it back on then frantically searched for a shop window to check that it was ok. It was. Funny thing is I blanked out everything so wasn't aware of any adverse comments being thrown at me.