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Thread: Craziest things you've done dressed...

  1. #26
    Member Detroit Molly's Avatar
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    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.
    Last edited by Detroit Molly; 09-04-2016 at 12:34 PM.

  2. #27
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    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!

  3. #28
    Member Jamie Erikson's Avatar
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    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.

  4. #29
    tiptoeing thru the tulips ellbee's Avatar
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    Adron, that's hilarious!


    I would have absolutely died, ha!

  5. #30
    If only dreams came true. susancheerleader's Avatar
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    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."

  6. #31
    Senior Member Tracy Irving's Avatar
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    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...

  7. #32
    Member Roxy's Avatar
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    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.

  8. #33
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    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

  9. #34
    Super Moderator Jeri Ann's Avatar
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    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

  10. #35
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    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.

  11. #36
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    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.

  12. #37
    Member Marcelo's Avatar
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    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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  13. #38
    Shy,very very shy Loveday's Avatar
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    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.

  14. #39
    Aspiring Member jjjjohanne's Avatar
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    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.
    I am a man who presents male and wears feminine clothes.
    I blog about my outings: https://joeypress.wordpress.com/

  15. #40
    Aspiring Member krissy's Avatar
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    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.

  16. #41
    Aspiring Member Samantha_Smile's Avatar
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    Quote Originally Posted by Dana44 View Post
    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
    Samantha -x-

  17. #42
    Member leannejacobs's Avatar
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    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.

  18. #43
    Pirate Queen wannabe Maria Blackwood's Avatar
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    Quote Originally Posted by GBJoker View Post
    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.

  19. #44
    Member Jeanettew's Avatar
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    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

  20. #45
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    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.

  21. #46
    Aspiring Member
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    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

  22. #47
    Multi-Blogger Barbara Black's Avatar
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    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!!

  23. #48
    Member Jocee's Avatar
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    Went to a strip club with a couple It was an interesting evening!

  24. #49
    Silver Member IleneD's Avatar
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    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.

  25. #50
    Aspiring Member Georgette_USA's Avatar
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    Quote Originally Posted by Jocee View Post
    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.

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