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Thread: The most daring

  1. #1
    Member MonicaPVD's Avatar
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    The most daring

    For those of us who are part time dressers, what's the most daring or extreme (PG-13) thing you have done in public while dressed?

  2. #2
    Platinum Member Teresa's Avatar
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    Monica,
    While I was part time it's hard to say what was the most daring as every step felt daring at the time .

    Looking back was it was possibly more in private when I took my first photographs . Then it was my first drive , or buying my first shoes or venturing out to get my skin colour checked for makeup ?

    Or could it be when I jumped in my car for the first time in a ballgown to visit my first social function in an open hotel ?

    As I say the list goes on as we progress .

    Is it daring for me now ? Well not anymore because I've left the man behind , I feel once you accept that it's no longer a series of dares , it's my life .
    The real me , no going back.

  3. #3
    Junior Member Diane426's Avatar
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    I think for me it's just being in a mall properly dressed and feeling totally feminine.

  4. #4
    New Member MilenaSometimes190's Avatar
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    Guess going out with feminine underwear under my male clothing.

  5. #5
    Junior Member JennyMay's Avatar
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    For me, at the moment, it is taking part in a support group Zoom meeting. I?m looking forward to going to a meeting when it is (COVID) safe to do so. It will be a big step for me.

  6. #6
    I can only be me Samm's Avatar
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    Going out alone for the first time, which was also my first time to a night club in girl mode. Yikes!

  7. #7
    Reality Check Krisi's Avatar
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    Walking downtown in public and walking through the mall (and getting stopped by one of those sales guys in the kiosk trying to sell some sort of skin tightener). The worst part is when someone speaks to you and you have to answer back.

    Of course, to do any of this I have to drive. Driving is fine but once I almost hit a bicyclist riding on the wrong side of the road at night. That would have been a mess.
    Krisi

  8. #8
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    Attended a lingerie party that was sponsored by a lingerie store. There were about a dozen GGs there. The hostess knew me, if anyone else knew I was not a real girl they did not let on. We laughed, talked and played games for a couple of hours. It was a lot of fun.

  9. #9
    Member jessica33's Avatar
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    During this pandemic lockdown I went to office as Jessica .

  10. #10
    Sunshine Gal AngelaYVR's Avatar
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    I would have to say that all the things I did that felt daring at the time now just feel normal. Some of those things were driving across Vancouver Island and taking a ferry, retrieving my car that had been towed (never a pleasant experience) and performing on stage at amateur drag night.

  11. #11
    Gold Member Helen_Highwater's Avatar
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    There's a few that might possibly qualify. Using a ladies public toilet for the first time as well as walking into the female changing room with 3 items while enfemme. Using public transport is another as you're sort of trapped there sitting next to folks shoulder to shoulder.

    I still think however for me at least the first time I went shopping enfemme would top the list. Exiting the car, putting on my coat, straightening my hair, grabbing my handbag, remembering to lock the car as I walked way across a busy car park and over the threshold of the shop door way I felt a bit like a rabbit in headlights. Thankfully the butterflies, that had felt like eagles, soon landed and I realised that all those good folk who'd said you'll be fine, just do it were right. Which is why those in the first paragraph were just that bit easier to do as the hard bit had been done.

    Just thought of another; while killing time waiting for a train going into a city centre non gay, not obviously LGBT friendly pub for a glass of wine. Standing at the bar I did feel somewhat exposed but hey I survived
    Who dares wears Get in, get out without being noticed

  12. #12
    New Member UsuallyRick's Avatar
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    It is an ongoing list of most daring events.. first was just wearing stuff in privacy of home, then venturing around our rural home.. went out on Halloween with wife and kids to local fire station for community fun spot and kids trick or treating,running into people we knew was a trip.. I was dressed as Lita Ford and tried to get wife to go as Ozzy🤣.. no go.. a grocery shopping trip(s) while family was out of town for several days was fun, along with dress shopping at local WalMart and trying on several dresses and purchasing a dress and some panties.. another was the goodwill store in man mode scooping up dresses and hitting the changing room, that was fun! Got some looks and help/tips from S/A!! It's been mostly subdued for the last year but this ski season I go full girl mode minus makeup under my uniform (ski pants as I work outside all winter) and lately because my normal ski pants are hot pink I have been wearing my favorite Obermayer pants for work as a statement to management that we are short on uniforms and the ones we have are at least 15yrs old so time for them to supply new ones or we will just wear whatever and not look professional as a team... I have been wearing my fuzzy hot pink zebra striped PJs around house and outside a lot and even in public occasionally, I love it!! Can't wait to get fully done up again and go out some more..

  13. #13
    Member Lori Ann Westlake's Avatar
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    I'm not very daring, and I've rarely been out. I guess the most daring thing I ever did was to go through a grocery store checkout alone, hoping I wouldn't be asked a question, knowing my voice would give me away if I answered.

  14. #14
    Aspiring Member Rachel M's Avatar
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    So I order two bras online from Soma with an in store pick up. I showed up early in guy mode to look at them on the rack. The SA asked what size I needed. I didn’t disclose I ordered already. So I’m looking at this bra with doubt it’s not gonna fit in the cups. I look up at the SA and tell her I am actually shopping for myself and asked if it would be okay to try it on. She paused for a moment and the said yes. I told her this is my first time in their store so I wasn’t sure between a 38 or 40 bandwidth. She grabbed both and took me back to a fitting room. She left me to try them on. She came back to check on me and the fit. We were talking over the door then I asked if I could just show her and opened the door. She saw what I was working with and we to get me a smaller cup size. I tried that one as well and didn’t like the fit and redressed. Back out on the floor, I told the SA I was there to pick up my order, but no longer needed it because of the fit. The other SA overheard and was preparing my order so she picked up in helping me. She was able to cancel my order without my card ever getting charged. I asked if they get other men shopping for themselves as I just did and she said yes they do. Great customer service. I think what helped was I kept my mask up the entire time.
    Rachel

  15. #15
    Soccer Mom in Training MsEva's Avatar
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    For me it was driving en femme from my home in VA to PA some 7 hours away. I have done this quite a few times, but have not had the opportunity since my parents passed away some ten years ago. It was always a thrill to make the long drive just as an female on the road.

  16. #16
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    For those of you who have ventured out (I tip my hat to you, obviously Prada or something) 😂

    The most daring I have ever been is wearing tights under trousers, or twice in the dark of night I?ve ventured out to my back garden bins... 🤷🏻*♀️

    Think I should rename myself lamely lamerson

  17. #17
    Princess Candice candykowal's Avatar
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    I suppose going to a new high school for my senior year and being able to present as the girl (I was living as Candice the whole summer) it was a bit un-nerving.
    I was very afraid I was going to be bullied and beatin up my first day. I happened a lot at my old school presenting as a boy.
    Those of you who remember High School in 1979, everyone...boys and girls, had long hair and wore jeans, so I fit in pretty well.
    There were days I longed to wear a skirt and when I did, I got teased a lot by the girls and they would pull on it or hike it up and tease me.
    The girls that be-friended me were more of a worry then the guys. The experiences I learned that year would carry through to college.
    Candice Coleen Kowal ....all my friends call me Candy!

  18. #18
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    For me, the most daring was actually getting totally dolled up on Halloween and buying doughnuts at a Winchell's Doughnut House. I had on full makeup including nail polish, a blond wig, jade green and black dress, and hosiery and heels. Underneath was all the proper undergarments; bra, slip and panty. The counter woman gave me a compliment. With some hindsight and reflection I wonder why my wife did not confront me when I came back into the house. She had to know I was gone and feinted sleeping. Getting ready and leaving had to be more daring than actually buying the doughnuts.

  19. #19
    Aspiring Member Sandi Beech's Avatar
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    Monica

    So as of yet, I guess my wildest thing to date is wearing nothing but lingerie into a bar - more than once I might add.

    There is a picture in one of my posts labeled- Maybe I am crazy.

    Let me just say I needed a drink to relax when wearing just a black maidenform slip, bra, black thigh highs and to top it off, black leather collar and cuffs. I got hit on by a young couple in just a few minutes so that was also crazy.

    I have worn a few variations of the same thing, and the Halloween before covid was the last time. I also had chains attaching my neck collar to wrists. The following night I went to the same bar and the bartender says - I saw you dancing last night. The attention is addictive and I found people were definitely looking. One guy wanted to know if I would go out to dinner with him wearing that. I was like , no way, I live here and likely to see someone I know.

    So Monica - you going to tell us your wild adventures? Haha.

    Sandi

  20. #20
    Gold Member Alice Torn's Avatar
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    My first night time out dressed, i drove around a small town late, and parked and walked around, then got back in the car, and drove back to a town where i had a motel room. and on the way, the local cop pulled me over. It all went fine, He just wanted to know what i was doing walking around a town late, when everything was closed and why my driving was erratic. No ticket. The next day, strutted around another bigger town in a mini dress, dark hose and heel. and was noticed and shouted at, by guys in a truck, and teens. Later in the day, went to a big city, parked and strutted, and got asked for a jump start, by a man with his family, who he told not to watch!! Gave him jump. and he thanked me. Another time, went waliking around a university campus park, and forgot to zip the back zipper on the dress, all the way up. It was only half zipped up, and i wondered why a girl was watching me, from the other side of the road, and laughed. Later, when i tok a back photo, i saw the back of the bra staring back at me!
    IT TAKES A REAL DRESS TO WEAR A MAN.

  21. #21
    Member MonicaPVD's Avatar
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    These are all wonderful experiences and a good cross section of our diverse circumstances. Over the years, I have had different opportunities to do outrageous things, ranging from silly to obscene. However, I must admit that the most extreme thing that I have ever done is to go on a date with a guy who insisted on me wearing a very inappropriate outfit for the occasion. He basically picked out the outfit for me. This meant that the whole night all eyes were on me and, trust me, they were looks of disgust and disapproval. My gentleman friend really enjoyed watching everyone's reaction. He had a great time. To clarify, we went to dinner at a very fancy restaurant and then to watch a play. I was wearing a way too small, and too tight, minidress with 5" heels, fishnet stockings and almost-Halloween-calibre makeup. I looked completely ridiculous and out of place. It was embarrassing for the first 20 minutes and then the rest of the night was like a comedy sketch.

  22. #22
    Platinum Member Karren Hutton's Avatar
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    I don't know.... even though I've done a lot of things enfemme.... going to Casino's dresses, getting trapped in the rest area ladies restroom on the intestate by a woman and her brood of female children and a pregnant woman throwng up in the next stall (almost had my skirt sucked down the toilet too...), drove on long business trips dressed, checked into and out of hotels dressed.. walked around an number of cities enfemme... did many quick gender changes in the family restrooms on freeway rest areas (walk in male and come out female)... Shopping in malls.. shopping in consignment shops... shopping shopping shopping enfemme. And I think that doing any of those things for the first time was daring and extremely exciting!

    The first time I left the house dressed I was 14 and had dressed in the basement when everyone was asleep. All my mother clothes (bra stuffed with socks, girdle, nylons, shoes, skirt and blouse) that I had stashed in an old cistern... but I had no wig so I took a hair net and placed a ton of curlers in it to give the appearance of having my hair set. Snuck up the outside stairway into a cold clear moon lit night. Remember shaking and shivering from the excitement. We lived in a small farming village in Southern Michigan and getting caught would have been devastating. So I took a walk around the block and as I rounded the last corner heading back towards the house, I could see a car's headlights coming up from behind me. I took of running down the street then cut through the neighbors yard, curlers flying and half tripping over my skirt. Made it back home but must have broken every world record that night but no one was watching to record it! None that I knew about! lol
    I'm a lumberjack and I'm OK......

  23. #23
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    Going to a gay bar a few times and getting hit on, kissed deeply in public a few times one wanted to catch a Uber to his motel in town and have his way with me but sadly in hindsight i declined, havent been since COVID unfortunately

  24. #24
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    If I'm honest? Putting in homemade breast forms for the first time in front of my wife...

    She's aware and accepting and all, I'm just very repressed.

  25. #25
    Aspiring Member TheHiddenMe's Avatar
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    Going to see U2 at an indoor arena with about 15,000 fans by myself (and taking public transit to attend). Second was probably seeing Hamilton in Chicago (also solo).

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