Craziest things you've done dressed...

[Marcelo]

I'm sure we all have our stories about crazy things we did while dressed up. Here is one of mine.

In 2013 I volunteered for the Rugged Maniac mud/obstacle run in Ennis, TX at the Texas Motorplex wearing my cheerleader uniform. That was not the crazy part. The crazy part is that, after my volunteer shift, I donned my crappy wig and did the mud run in my uniform. What was cool is that almost everyone was going wild over my costume and asking me to pose with them for pics!

Let me get this straight - I was wearing a cheerleader uniform with a really short pleated skirt (white trunks with red polka-dots underneath) climbing over walls, crawling through mud pits and tunnels, jumping over fire, etc... with all the other people in my wave. It was the only mud run I've ever finished, as well as the easiest one, and I'm sticking to volunteering from now on.

They recently took down the photo albums from back then or I would swipe a few to post. But here is a link to someone's video from that day who got a shot of me at my volunteer station. It's short but I'm on the left side of the video.
https://youtu.be/uNndPT4ChkA?t=8m50s

So what are some of the craziest things you've done while dressed up?

Cheers!
Marcelo

[GBJoker]

I once got completely dressed up and......... played some video games on my computer. Actually, have done that several times.

Hey, at least I answered honestly.

Edit: I suddenly feel incredibly boring...

[Dana44]

Yeah I have played computer games dressed. My SO said crawling under the truck while dressed, yeah I remember that as my diesel truck overflowed on fuel and was dumping we had to put stuff under it and clean it up. LOL was dressed and working with another truck driver that saw it. Wonder what he thought. LOL

[ellbee]

I was once a mistress of gay man who was in a long-term commitment with his (male) partner.

Though I say that loosely, as I honestly don't know just how "open," if at all, their arrangements were.


He knew me as both my guy-self & as my femme-self.

But we only got physically intimate (on multiple occasions) when I was all dolled-up, as I didn't want that any other way.


Believe me, I dug my heels in, pun not intended, the whole process there. Though eventually, with enough time, charm & persistence, he roped me in -- but only because I wanted to be.

I was his for the taking, and for the most part, I loved it. He was my first & only, and I'm glad it was him. It was pretty amazing to be on the other side of things for a change. And yes, we were "safe," of course.


After we stopped seeing each other, I did struggle a bit with all that had happened. I still find it hard to believe sometimes. But, there we go.

And honestly, I wouldn't have changed a thing. No regrets.


Still hetero as a guy -- but I do have to admit now that I'm bi as a chick. It would take me a lot to get there, but I'd *possibly* be open to that again someday, with the right guy under the right circumstances. I really don't know; too tough to say.



Personally, I think it was probably my craziest thing I've done with all this. YMMV


And for those reading this: This doesn't mean it will be typical for you (or for the BF/husband in your life). This was simply *me*. That's all.

Please keep that in mind, thanks. ;)

[docrobbysherry]

I probably have so many I've forgotten them. But, 2 that come to mind r:

Dressing and taking photos in a Vegas casino. They don't let u take photos in any gaming areas and busted me! When they found out I was a hotel guest and checked me out they released me after nearly an hour. This was just before security stopped me!:doh:
265691

Doing a mermaid shoot in my pool. My T friend who's scared to death of water and can't swim was filming. Suddenly, my tail began filling with water. The more I kicked, the more it filled. After a horrendous struggle, I just barely made it to the side of the pool!:eek:
Here I am about to go under again.
265692

[CatchQueen]

I got the book thrown at me for jaywalking while dressed...(well for jaywalking only, being dressed had nothing to do with it lol)...that hurt...doing a video on it soon.

[CarlaWestin]

I did a full brake job on a Ford F150 with some rather large breasts in the way the whole time.

[Lea]

While mild compared to others on Halloween I went out with my wife and mother dressed. My wife knows and is supportive. My mom always wanted a girl so for one evening she had one.

[NicoleScott]

Carla, I've seen shows on TV where they jack up buildings, barges, etc. with big air bags. Just wondering if you ued your breasts to, you know......?

[Heisthebride]

Perform en femme as a member of a burlesque troupe in front of a live audience. I actually do that quite often.

265730

[Petra1]

Changed the oil on my car with 44DDDs.

[CarlaWestin]

Carla, I've seen shows on TV where they jack up buildings, barges, etc. with big air bags. Just wondering if you ued your breasts to, you know......?

No, I had all the right equipment. They just kept me company.

265756

[misschris]

Love seeing all the great pics! Thanks for sharing. Crazing thing I've done? Prolly doing my late night delivery route in a silk camisole and panty and dropping freight using their forklift. It was 4:00 in the morning....no one was there...except maybe the security cameras.

[ellbee]

Doing a mermaid shoot in my pool....


I hope you don't mind me saying so, but I found your story & photo hilarious! :roflmao:

Happy to hear that you made it out okay. And being safe is certainly something to keep in mind with all this kind of stuff.




While mild compared to others on Halloween I went out with my wife and mother dressed. My wife knows and is supportive. My mom always wanted a girl so for one evening she had one.

Awesome! So jealous. Must have been really fun. And keep in mind, this is never a competition... We're all at various stages with this. For some, even simply driving around the block a few times at night for the first time, or whatever, is a huge & crazy thing for them, and rightfully so.




Perform en femme as a member of a burlesque troupe in front of a live audience. I actually do that quite often.

Ugh, that must be so much fun! I could never bring myself to do something like that. I'm really not an on-stage performer, no matter what I'm wearing. The closest I came was simply *considering* being part of a supporting cast for a friend who does drag shows. But I was just too chicken. :(

[Marcelo]

Love seeing all the great pics! Thanks for sharing. Crazing thing I've done? Prolly doing my late night delivery route in a silk camisole and panty and dropping freight using their forklift. It was 4:00 in the morning....no one was there...except maybe the security cameras.

I was doing the Electric Zombie Run in Dallas a few years ago at Community Beer and after my paid shift I went to change in the warehouse. I usually slip on my skirt before slipping off my my shorts but I decided to slip off my shorts first. There I was in their warehouse, if only for a minute, in just my panties on the bottom. I was not far around the corner from the makeup tables and saw no one else but it was kind of fun. Maybe the security guys got a look!

[Alice_2014_B]

Driving to a gas sation fully en femme in broad daylight, short jean skirt and knee-chunky heeled boots.
Aside from that, I've only been out at night.
:)

[Marcelo]

[COLOR="#000080"][FONT=Verdana]Okay, this was almost disastrous but it was probably the most thrilling stupid thing I've done.

My old apartments were great for just walking around as well as walking around in drag at night. I had this crazy fantasy of walking around in nothing but bra and panty (matching) besides shoes and socks. The first few times I did it was in plain bra and panties from JCPenney. Then I found these beautiful and incredibly sexy bright white bra and panty by Gilligan & O'Malley at Target. The panty had fine netting from the hips to the front diamond (pubic area) with roses embroidered on either side. On top of the solid material of the diamond was a ribbon bow. The bra cups were all lace and I stuffed them with cotton balls. I wasn't impressed with the bra but the panty was the sexiest thing I've ever owned! I also had a long brunette wig.

I started out just walking around the clump of units in the back where I stayed. It was pretty safe - even as early in the evening as 9:00 PM. I knew all the little grassy paths between the buildings in case of an emergency. And I ventured out quite a bit in nothing but my bra and panties without incident - even though I did duck from cars on several occasions. I even saw my neighbor's daughter sitting in the breezeway as I passed their unit. I wanted to run by her but I knew she was going through some difficult times and didn't need that.

Okay, I finally got the nerve to cross the parking lot into the front section of buildings and planned on reaching the mailboxes at the entrance of the complex. I was almost there when I heard "look" from a balcony right above me. I looked up and saw a couple sitting in the dark and calmly turned around and walked across the well lit court yard in the middle of the cluster of buildings. I was about halfway across when I saw a cop slowly driving by on the street between my area and the area I was in. It passed on by and I quickly made my way to the street to watch it turned the corner toward the back where I stayed.

I could have probably passed Usain Bolt at the speed I was running - I'm surprised I didn't fall out of my panties along the way. I made my way to my unit by the back way, hid my bra and panties and jumped in bed as soon as I could. It was a fun night!

Marcelo

[julia marie]

I've seen mud runs. I couldn't do them under any circumstances. So, congrats for doing that. Doing it as a cheerleader, many bonus points.
For me, the craziest thing could be taking the step to go to the beach in a halter top bathing suit and actually sunbathing and going into the surf. Did anyone notice that i was different? I don't know. But I did make I used sunscreen on my thighs, which never see sunshine in my mens bathing suits.

[Lorileah]

Marcelo, one would think that maybe you're an exhibitionist.

[ellbee]

Ya think? :laughing:

[Marcelo]

marcelo, one would think that maybe you're an exhibitionist.

Yes, that is correct! ;-)

[arial]

Gone squirrel hunting. depending on the time of day, wearing anything from a gown and peignoir w/heels to a skirt and top with flats.

No camoflage though.

[Judy-Somthing]

When I was 18 I got fully dressed and went out for a walk at about 1:00 AM.
Some guy in a car started driving beside me asking me if I wanted a ride.
I ignored him and he finally drove off.
I suspected he would come back so in my favorite dress I crawled under a car in someone's driveway.
Well I was right, a few minuets later he drove down the street very slowly looking for me.

After staying under the car for about 30 minuets I ran home as fast as I could.
I never went out again!

[Krisi]

I'm not one to do crazy things so I wasn't going to post but I see several posts about going out in public as a woman and I have done that several times. I have walked in the park, down city streets, in shopping malls and put gas in my car. All as Krisi.

Some of us have done a lot more, some far less. If we all inspire each other, that's a good thing.

[docrobbysherry]

Marcelo, one would think that maybe you're an exhibitionist.

Lorileah, dressing has that odd effect on a lot of us otherwise shy, retiring, and invisible in drab mode, guys.:heehee:

[Detroit Molly]

Spent almost the entirety of Mardi Gras 2012 and Mardi Gras 2015 en femme. My band plays Mardi Gras every couple years, so I always take the opportunity to spend as much time as Molly playing and partying down there. Basically I step off the tour bus, put my wig on, and it's go-time.

Oh, and here's a funny story from 2012. We marched a parade called the Box of Wine Parade on Sunday afternoon. It's a really cool, laid back parade but it's called "Box of Wine" for a reason. As we marched, these mostly naked nymphs and satyrs who were the Queen's court kept dancing through the parade with either boxes of box wine or red, five-gallon gas cans full of wine. When a girl wearing nothing but faerie wings, pasties, and a large leafy tutu dances up to you to pour a bunch of white wine into your mouth from a gas can you don't say no.

By the end of the parade I was apocalyptically drunk, and on the walk back to where we were staying I got separated from the band. So here I am walking alone drunk through thronging crowds on St. Charles all dolled up carrying my horn and having no idea where I was. Eventually I just went to a taxi stand and a very cute young man picked me up. He turned out to be Basque, and spent the entire time checking me out in the car mirror, and when he dropped me off he tried real hard to get my number. It was adorable.

[Adron2009]

Ha this thread made me smile at a fond memory. My wife and I decided to go out shopping along Charles Street in Boston one day. I wore a sun dress, the length just above the knee, not to short but not too long. Had a nice pair of sandals with heels and was really enjoying myself and my look. So we find this antique store my wife just has to go into, and of course finds this wooden bench seat she just loves and has to have. Fortunately we had driven my pickup but the question was how does this get to my truck (as there was absolutely no room to get my truck anywhere near the store). So the lady working in the store tells us "let me call the guy next door, he always helps people with stuff." So I am like really, now I have to help carry this thing several blocks down the street with this guy? I just look at my wife with the "really" look. She just starts laughing at me! So this guy and I carry the bench to my truck and I manage not to fall on the uneven sidewalks of Boston with my heels on, quite a feat. So we get to my truck and I had not really thought this through, we put down the bench and the guys just stands there and looks at me like well it's your truck get up in there. So here I am climbing in the back of my truck in a dress and heels and at the same time lifting this bench up while trying to hold down my dress due to a light breeze. Well for those of you who know Boston and the Duck boats along comes one in time to stop at the light and everyone on board is watching me in the back of my truck loading this bench and tying it down! I just smiled at everyone and kept on going. What a memory and thanks for this thread for bringing back to life for me!

[Jamie Erikson]

Craziest thing I did was to buy a piercing gun and a bunch of studs. I proceeded to put 3 more studs in one ear and 1 in the other, then pierced my nose and 3 around my lower lip! Actually got lots of favorable comments mostly about the pain.
Was wearing a full outfit and makeup and high heels.

[ellbee]

Adron, that's hilarious! :lol2:


I would have absolutely died, ha!

[susancheerleader]

You can guess I like the cheerleader thing.

So here I am. 52 year old man. I'm wearing a women's cheerleader uniform. Thankfully it's Halloween so for the most part, that's how it went.
But I got got comments "best costume ever."

[Tracy Irving]

Like misschris, I spent some time doing an overnight delivery route while dressed. Two nights and five different outfits. Shorts, tops and dresses. Many people drove past the stores but only the security cameras were definitely looking...

[Roxy]

Except for a few nite outings around the house and a long drive to a jod site, I don't usually go out dressed. I have dressed at at a couple of theme parties where I feldt safe. One of those parties was the SF Exotic Errotic a few years ago. I was dressed as a big, pink ballerina. Hose, heels, tutu, big breat, bodysuit, and blond wig. Everything. Everybody wanted to get their picture taken with me. Studdly guys, gang banger looking guys, and girls of all ages. It was a little overwelming and scary/exciting at the same time.

[Jane277]

Just last night me and the wife picked up her mother from the airport while I was dressed, we told her I was trying on my Halloween costume lol, after a few minutes I told her the truth and she was very cool and accepting about it, she is the only person besides my wife and myself who knows

[Jeri Ann]

My oldest grandson will be twenty soon. Shortly after he was born Our daughter had serious Post-partum Depression. I suggested that her and her mom go away for a long weekend and I would keep the baby. He was six weeks old. For four days and three nights I was in girl mode caring for an infant. It was amazing. We even went to the grocery store and shopping at a department store. One thing I didn't count on was the fact that that precious little baby was a chick magnet, which caused some uncomfortable moments. There was never an issue, however, because everyone was so drawn to the baby I was barely noticed.
Jeri

[Mgreenva]

I went into Catherine's in drap (under dressed) except wearing 5 inch heels. Tried in an bought a dress. Then It hit me I wanted to wear in home. I asked to use the dressing room again changed into the dress. Said high to a lady shopping as I walked out. There was a guy in his car that watched a man in a dress and heels walk across the parking lot to my truck. On the way home I stopped for gas and even walked in and bought a drink and chips It felt like wow. Absolutely liberating.

[Sarasometimes]

I volunteered to be a model for a professional makeup artist class. I arrived fully dressed expecting to get my makeup done like for a special occasion/wedding instead I find out I'm the model for a drag application (not my area of interest at all). The artist then proceeds to remove my wig to better show the process. There were about a 10 to 12 female students and felt like I what a nude model for an art class feels like only worse. I felt so self-conscious I wanted to run out of there. The students were great, they quickly realized how I was feeling and thanked me for coming and that I should just relax and chill. Well I thought I would be there for an hour or so but 2:30 later the wig was finally place back on my head and teased up big. I was then finally allowed to see what I looked like and it was amazing, absolutely nothing like myself. I then gave the students free rein to take all the photos they wanted. They encouraged me to "Work it girl" and guided me into some fun poses...Not sure I would do it again but in the end it was fun. Scary but fun.

[Marcelo]

I just remembered something really crazy today. Back in 2013 I attended one of those zombie runs where some dress as zombies and try to steal life flags (from flag football belts) from the runners. I was wearing my nice Tigers cheerleader uniform that was a bit too small and the skirt really short. I actually had an athletic brief on order and it came in the following Monday. But all I wore under my skirt was a white granny panty I bought at WalMart.

I thought there was a chance that my skirt might come up enough so that people might see it and sure enough it did - many times! I know because one of the photographers opened a drop box for me and I saw the pics myself. Unfortunately those granny panties looked awful or I would have kept the pics I had posted on Flickr. One of the guys in our posse even mentioned my "panties" at one point that day. The moral of this is that you should always wearing fashionable underwear - especially when wearing a short pleated skirt doing a zombie run.

The next year I did two more zombie runs but those times wearing one of my homemade gaffs under a Star White Vanity Fair Illuminations string bikini. I'm pretty sure I was flashing them left and right but no one shared any pics.

Those were some fun times and I hope to do it again next month at another zombie run.

Marcelo

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[Loveday]

Took a leak in the men's side of the public restrooms in a rest area along I-75. I thought nobody would come in since it was late at night. Well you guessed it, two rough looking characters walked in and saw me peeing at the urinal wearing a mini and high heals, I left real quick, you might say I got my heals clicking, got in my car and left.

[jjjjohanne]

My craziest thing was buying a car while dressed in a skirt, black hose, flats, and a blouse. No makeup, wig, or breasts. Just a man, trapped for a few hours at a car lot with car salesmen. It wasn't that bad. I was treated with respect and I bought a car.

[krissy]

My ex would dress me up then tell me to drive across town and get a newspaper from the ut texas at the time you could only get them near or at the ut of texas .one night i got pulled over by the police .i was all made up i had a nice silk short dress garter and stockings matching panties and bra my ex bought me some fake rubber breast at kress store any way the officer saw how i was dressed told me to get out of car had me face the car searched me then asked why i dressed like this i told him i liked it he told me to take a seat in his car .as i sat there i was freaking out i thought i was going to jail dressed as i was .he asked me what i was going to do if he let me go i told him i would go straight home. he let me go after awhile i hauled ass home my ex just laughed at me and said next time i would have to go walking to store but that was a whole other story. she used to like to put me in embarrassing situations and i did it so i could dress.:daydreaming:

[Samantha_Smile]

My SO said crawling under the truck while dressed, yeah I remember that as my diesel truck overflowed on fuel and was dumping we had to put stuff under it and clean it up. LOL was dressed and working with another truck driver that saw it. Wonder what he thought. LOL

Probably thought to himself "What a weirdo - those boots are SOOOO wrong for that dress" as he finished fastening his suspender clips :D

[leannejacobs]

I once painted my boat while fully dressed in a mini skirt heels the works and no it wasn't at the harbour lol it was in a large shed, other than that I regularly drive a 200 mile journey totally en femme.

[Maria Blackwood]

I once got completely dressed up and......... played some video games on my computer. Actually, have done that several times.

Hey, at least I answered honestly.

Edit: I suddenly feel incredibly boring...

I game all the time while dressed, although it's mainly because I'm in CD mode at all times at home.

And I always play female characters given the option. I couldn't with the new Deus Ex, but it was OK because Adam Jensen is pretty badass.

My CD crazy doesn't get any more interesting than cleaning the garage in one of my maid outfits.

[Jeanettew]

My wife had gone to work early so I completely dressed then got in my car and drove 300ks to port Augusta for business, took me three hours overtaking truck and just feeling nice just outside Augusta I slipped into a parking bay and changed for work just loved it

[abby054]

I went on a late night walk around the block, like many that are described in this forum from time to time. About halfway around the block, I encountered a large, growling dog partially blocking the sidewalk. I just kept on walking as if the dog was not there. The look on the dog's face was priceless. By the way, in drab, I have a phobia of dogs, so bad that my landlord when I was younger told me that he considered denying a basement apartment to me because of the fear that I showed when first meeting his dog.

I went to a music recital en femme and my super nosy landlord (not the same one as mentioned above) and his talkative wife came in and sat next to me. They never recognized me. Or they are great actors.

I went on a week long vacation by myself. I packed a full suitcase of Abby's treasures and never opened it.

I went shopping en femme at the Freehold Raceway Mall one evening. I gathered several items to try on. While in the dressing room, at least four girls, probably teenagers, came in chatty and giggling. They tried on their selections in the next cubicle. They chatted about how they would like to dress up one of their boyfriends, who was apparently waiting outside. They describe what he would look like in the clothes that they were trying on. They speculated how cute and passable he would be. This went on for several minutes and included how they would like to do his makeup as well. I waited until I was sure they were long gone before I exited my dressing room.

By the way, on another day, two years earlier, a SA in St. Louis, Missouri, invaded a dressing room that I was using in drab and evicted me and quite loudly.

[AlyssaJ]

Back in 1997 wore a skirt, panties and black tights to work. Everything else about me was male. I worked in a small office of about 60 employees doing software tech support over the phone. At lunch, I went with two of my female co-workers out to a local grocery store to get some hot food from their buffet. I still remember the odd look of the presumably recently immigrated Asian clerk at the checkout counter. He couldn't help but stare and had no clue what to make of it.

Oh did I mention, the ladies I went to the store with bought me lunch that day :)

[Barbara Black]

My craziest was yesterday, going through the drive thru ice cream shop in full femwear, without the benefit of shaving either my arms or face. But I will top it!!

[Jocee]

Went to a strip club with a couple :) It was an interesting evening!

[IleneD]

I was traveling; a long bicycle trip of some 250 miles, and stayed at a turn-of-the-century 'railroad' hotel in a small (midwestern) town along the trail. Swank, richly appointed wood lobby, interiors like they don't make anymore, etc.
I brought my favorite long blue floral print dress and heels (amazing- of all the things to bring in a camping bag), underwear but no wig or makeup except lipstick. I dressed in my favorite silk headscarf.
I took the elevator to the empty lobby and confidently strode past Alex, the night clerk. He saw. Being a small rural town, the streets around the courthouse square were nearly deserted. I walked a block or so to one of the few restaurants reasonably near. I'd scouted it earlier, and sure enough there were only about 2 tables occupied inside. I elected to seat myself at the outside curb table.
My waitress was outstanding. The conversation naturally broke (about a man in a dress); and by the time my meal arrived she and her wait-staff were buying me the rest of my wine for the evening. Donna, (the waitress), was practically in tears, saying she had friends who were CD, trans, gay, etc.; and she thought me going OUT in public dressed was beautiful; and she thought the dress was adorable. (Loved hearing that.)
When I returned to the hotel, the lobby was still void of guests. I wanted to leave an early wakeup call and approached the lobby desk to address Alex (clerk).
" Yes, Alex. You're seeing what you're seeing. A man in a dress. Now, be a dear and set up a 6am wake up for room 300." The poor lad was beside himself stuttering for a response; something kind and socially understanding. I assured him to not trouble himself. This was all in good fun, and coaxed him to snap a cellphone picture of me (dressed) in the hotel lobby.
The feeling of such freedom was exhilarating.

[Georgette_USA]

Went to a strip club with a couple :)


Was it a female or male strip club. We have a club in WASH DC that has nude male dancers.