Funniest thing that ever happened to you.

[I Am Paula]

This post is just to share some of those really funny moments crossdressed. Either out and about, or in the privacy of home sh*t happens. here's one of mine.

Back when I was still young enough to pull off the look, spandex skirt, garterbelt and stockings, sky high heels... I pulled up right in front of the night club we were meeting at in my neighbours huge SUV. I decided on valet parking cause this car seemed about 30 feet long, and I didn't want to park it. I opened the door and looked down, I felt like it was 6 feet to the ground. The only ladylike way I could figure to exit this beast was to turn sideways in the seat, and just drop to the ground. Instead of landing daintily, the seatbelt holder beside the seat grabbed the back of my skirt and yanked it up around my armpits, so I hit the ground showing the line up outside the club everything I usually keep hidden under my skirt. I was also stuck!!! A doorman saw my dilemma and rescued me and my clothes, but not my pride or modesty.

Okay girls, let's hear yours (c'mon we've all had one)

[Chickhe]

Beats all the other negative threads...soooo...

Not quite as dramatic, but I once went to a halloween party dressed and it turns out I was fitting in pretty well since I was making my way to the men's washroom and I was grabbed my the arm by a girl I did not know who pulled me to the woman's and she said..oh no, be careful, did you know you almost went in to the men's washroom!!!! I was a bit shocked, all I could do was make a face and mouth thanks... had to avoid talking, but it went okay and my wife thought it was hilarious too! The washroom was packed and I had no issues at all. Later that night there were other funny situations that I'll never forget.

[erickka]

Dressed up for Halloween about 25 years ago, I had no money for forms, so the old water balloons had to do. I was with my then G/F at Mickey D's ordering at the counter when all of the sudden my left water boob exploded! Every one there (including the staff) got a good laugh. I was embarassed, but laughed it off. We sat down and and proceeded to finish our meal, even though I was wet and lopsided!

[Rogina B]

Two Sunday mornings ago,I took a motorcyclist up on his offer to give me a ride the half mile back to where the truck was awaiting fresh fuel for it's filter housing..."Miss,do you need a ride back to your car?"[a one ton diesel work truck lol] So,in my best voice,I took him up on the offer..He thought he had a "chick in a sweaterdress" on the tail of his bike....until...a small delivery truck pulled up next to us and asked directions to a place that my "driver" did not,so,I open my mouth to tell the guy how to get there. In my normal voice,I give the guy directions..and the expressions on their faces was priceless! Now,he isn't sure just "what" is sitting on the tail of his bike,but he knows that I am not getting off! We went up the road,he pulled over by the truck and said "here you go" in a tone that wasn't happy. So,I turned to him and said,[womanly voice] "If I didn't have a bad cold,I would give you a BIG kiss for helping me!" He roared off and I had the truck restarted in a minute..I am still laughing over it.

[Beverley Sims]

I think I have just related my funniest moment in another thread.
I was with a group of GG's about ten in all and known by two of them..
A guy in a dress walked into the restaurant and attention and conversation was diverted to this situation.
A general discussion ensued as to how he looked, likes and dislikes of weird people like this and so on.
I had to pass an opinion that was in the negative for me saying I would not date a guy who did that and what satisfaction does he get out of it.
A couple of the girls started to look at me a little more closely and this made me uneasy.
The two that knew thought it was hilarious and tried to drop me in it.
Then the waiter came and took our order.... Phew! :)

[Chickhe]

Rogina...that is funny, but risky. Anyhow, maybe he will write a song about it.

[Karren H]

A few years ago I was driving home from a business trip enfemme and stopped at a rest area on to turnpike to use the ladies room... pretty quiet when I went into the stall... then an apparently pregnant woman comes into the stall next to me and starts throwing up..... fun.... so I'm about ready to leave and a mother and her 6 daughters enter the restroom.... and stay for like fore ever... I felt trapped.... finally they leave and I figure its safe so I flush only to find my skirt is beige sucked down the toilet.... I sop up what I can and go out and wash up.... and I'm standing there drying my skirt with the hand dryer when this little old lady walks in and asks "having a problem dear?"..... More than you could imagine... lol

[Debra Russell]

My very first and only time out with my wife, we went to the casino - while standing in line at the cafe ordering something to eat and being nervous because the old grouchy lady behind the cash register was giving me the stinkeye - I dropped my purse, dumped our fruit salad all over the floor. I picked it all up and we found a table - my wife went to get some napkins as a cute young waitress came over with a another complimentary salad and said "thats all right sweety here's another one". Embaressing, funny - my wife almost died laughing - I wanted to crawl under the table - ol' stinkeye was still glaring at me, and the whole dinning room was watching :o we did go on to play a little slots -----but that's the last time my wife went with me :sad:

This was still early in my cd'ing and expierence as lacking....fun to look back and remember....................Debra

[lilmissjenny]

last Halloween me and my gf went to a club. i was dressed as a pirate wench and she was dressed as a school girl. we go in and no problems and we even got a few compliments on our costumes. well me and my gf go get a beer at the bar and then we proceeded to walk to the stage and watch the band play. after a few minutes, i get a tap on my shoulder and turn around and seen some guy standing there. i look at him and he has this "oh sh*t!" look on his face as he notices that im a guy. he quickly walks away back to his buddies who all were laughing at him...lol. me and my gf of course laughed too as we thought it was hillarious as well. we left shortly afterwards continuing to laugh about it...lol.

[LadyPilot]

I went to a local swimming pool for the evening swim aerobics class, now I have never been to this particular city pool; therefore, no worries plus the evening classes aren’t too busy. I arrived wearing a dress, hose, bra, etc.. no hair or make-up so I went into the men’s locker room which wasn’t busy and changed into my one-piece swimsuit and joined the aerobics class. After class I went back in locker room to change back into my dress and stuff then headed out to lobby. When I went into the lobby there were teenagers everywhere as buses just showed up for a district swim meet.

[AllieSF]

I have two that both involve skirts. The first was when a group of us were having a drink in a hotel lobby bar close to the theater where we were going to see the play Wicked. I went to the bathroom and tried to be careful keeping my gold pleated and very lady like skirt from dipping itself in the toilet. That evening there was no such luck. I dried it as best possible and then just grinned and got on with life so as to not be late for the play. The second time I was at a nice upscale restaurant with a dear friend here. I stood up to go to the bathroom, but my skirt had other ideas as it decided to quickly sit back down as I was standing up. Thanks to a timely notice from my friend I realized what happened and sat right down to scold my skirt and zip it back up more securely.

[Kate Simmons]

Actually I was in the Army in Nam just ready to come back home from my second tour there. My friend and I stopped in a USO show going on and I got called up to the stage to participate in an act. The guy was doing slight of hand and he made a bra "appear" supposedly from under my shirt.He said "I think you've been over here too long." Little did they know. Right after that they began singing the Beatle's song "A little help from my friends" On cue just before they got to the part "would you stand up and walk out on me", my friend and I got up and left. Their mouths went open and dead silence. The other GI's applauded and cheered us. That made my night.:)

[Tracii G]

Its been a while back and still pretty funny to me at least.
I was at a club enfemme with two GG's and one guy.I had to pee really bad and Tom had to go as well so we head off to the restrooms.We get close to the ladies room and there is a very long line.
I get in line and he goes to the mens room I'm still in line when he comes out so he grabs my hand and takes me into the mens room with me laughing.
We come out and he says was that quickie good for you baby?
The girls in line started clapping and saying You go Girl!!

[Joanne f]

In my early days (a very long time ago) I went to a seaside town with my wife and bought a long skirt which I could not wait to wear so on the way home we had to pass through a very lonely wooded area , so we stopped in a suitable spot , I put the skirt on and went for a walk as I assumed that no one would be around , my wife stayed in the car, I got half way up a long track when I suddenly heard voice's coming in my direction , well I thought " Oh poo" hoisted the skirt up to my knees and legged it back down the track where I saw my wife laughing her head off watching me trying to run in a long skirt and climbing over a 5 bar gate only to find that I had ripped the knew skirt on some brambles :sad:

[MssHyde]

2011 I dressed as a pirate woman captain. i had a few hundred in the outfit being careful with prices. every thing was real the sword the coat, boots etc. I had breast forms, long curly streaked wig a lot of woman's rings and bangles.

I worked a year on this outfit. I was nervous how I would pass and look. we went to a Halloween party. I was selected for best outfit. I was on cloud nine..

I was at the point where I had to pee. I went to the men's restroom. the guys did a double take. that was funny.

then as soon as I come out a couple of women swarmed me. about going into the mens restroom.

I had my cleavage showing etc. I explained to one woman I was a guy, she said "no your not."

she grabbed my breast and said "your not a guy." I showed her my hands she said "your not a guy."

I called my wife over and had her tell her I was a man and also her husband. (she argued with my wife too)

the one woman was dressed as a woman cop. she took out her hand cuffs and said "I'm going to have to write you up,you look like a woman."

it was really funny she had another woman feel my breast afterwards too. to see how real it felt.

I was loving it.
http://i995.photobucket.com/albums/af73/xHDrider/Brandi/1031112343a.jpg
http://i995.photobucket.com/albums/af73/xHDrider/Brandi/setting_party.jpg

[christinac]

Funniest thing that I've ever had happen so far was about two years ago I went for a bicycle ride and I had on a pair of fluorescent pink gym shorts and a white muscle shirt and I wasn't really even trying to be en-femme it was just what was handy at the time. Anyway I was riding down a side street and this car comes up beside me and stays up with me but far enough back where I couldn't see in it without turning completely around. This kept up for about two blocks when I suddenly hit my brakes and the car came up far enough for me to see inside and I see these two eye balls about the size of basket balls and the guy blurts "What the ****!! That ***** is a dude!!" and away that car went faster than a bolt of lightning.

[Sally24]

I have quite a few halter dresses and some of them fit better if I insert my forms directly into the lining of the dress. One of my favorites, a cache' dress that I got for $15, was showing a little wear and had some stitches coming out from that area. I wore it to the club that night anyway as I was in the mood for THAT dress. After doing some karaoke we got onto the dance floor and were having a good time. My chest started to feel a little funny and finally things really felt strange. I looked down and on the dance floor is this big sunny side up egg, NOT. I scooped my form up quick as a wink and stuffed it back inside my dress. The really funny thing is I'm pretty sure I was the only one to notice!!
:heehee:

[Veronnie2]

Being a stocking and garter belt gurl, most of my funny experiences have been related to stocking snafu's. I was going down to a bar at a hotel I was staying at and as I left the room I felt a stocking clasp release from my stocking top. Instead of going back into my room I went to the sheltered ice machine area. I thought no one was around, (wrong) While I was re-attaching the rear clasp to my stocking, and yes, my skirt was hiked up so I could work properly, I looked over my shoulder and saw this elderly man looking at my legs and ass. I smoothed my skirt back into place and as I turned to leave I heard him say..."Thank you very much pretty lady." My response was "your welcome" as I walked away. As I walked to the elevator my smiles turned to laughter. Oh and yes He also came to the bar later with his wife, and kept looking towards me. I still wonder what exactly he was thinking. Veronnie2

[stephNE]

At the time this happened it was frightening, but after it was very funny. One evening my wife gave me a list of things we wanted from the grocery store. So we put the kids to bed, I dressed and went out to a store in the next town. On the way back, I was thinking it was still sort of early and wanted a soda to have while I watch some TV for the night. So I went a bit out of the way by a 7-11 (convenience store). I pulled up slowly checking to see that there wasn’t a big group of people in there. It was almost empty so I pulled in and parked. As soon as I turned off my car, another pulled in and parked in the spot next to me. I looked over and it was a county policeman. My heart was racing! I thought about leaving, but figured then he would surely think I was up to something, so I went ahead and got out of the car. As I approached the door, he moved quickly to get there before me, he opened the door and asked “Hello, how are you tonight?” In my softest voice, I said fine and asked how he was too, and moved quickly to the soda machine at the back of the store. But he followed me and got up very close to me and asked “Nice night tonight, isn’t it?” So I said “Yes it is” and moved on the pay for my drink. He followed me again and before I could pay and get out of there he said “Have a nice evening.” I turned around, smiled, did a little hand wave and got the heck out of there.

The more I thought about it, I wonder, did I pass and he thought I was a woman? Was he hitting on me? Or was I not even close to passing and he just wanted to check me out? Or did he know I was a guy, figured I might be gay, and wanted to hit on me. Hmmmmm. I guess I’ll never know.