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Most Daring Thing You Have Done Crossdressed?


Guest Jessie_Cd

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Guest gailgirl9

Although I am a bit overweight (If you can stand it, a corset from Fredericks can do wonders though!) , I pass really well. As a result, I have gotten pretty comfortable shopping in malls, and trying on outfits. I try to choose the stores where they don't have salespeople "guarding" the dressing rooms. A few weeks ago, I was able to dress for 36 hours straight :) . I was feeling confident on Sunday, and I went into a smaller, more specialty store. I told the salesgirl that I had an important date with a guy who I was hoping would ask me out. She recommended a number of dresses, and evaluated me in each as I came out into the open triple mirror area, commenting on how each dress flattered me or not. One of the other customers even commented on a couple of the dresses. What a thrill!

I didn't actually buy a dress (didn't really have the date :( ), but I had so much fun. I have no idea whether I was "read"- if I was, they didn't show any sign of it.

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Guest Sarah Miller

Well I have now done the most daring thing for me whilst cross dressed. I went out in public for the first time the other night. It was with a large group of Cders on a harbour cruise and dinner at night. I was terrified walking with my friend to the car in the hotel basement, leaving the car, and standing on the wharf waiting for the boat being stared at by guys fishing.

Wouldn't have traded any of it away though. I can not wait until I can go out as a beautiful women again.

xxo Sarah

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  • 4 weeks later...
Guest Annalee

My sister took me shopping, geheesh what a rush!! and yes, I used the dressing room trying on all sorts of outfits, one piece bikini's and you know what? the ladies didn't seem to mind at all, I walked around wearing panties, matching bra and two inch heels, I was so nervous!! but got kinda relaxed when I noticed that's what most of the women were wearing...

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Guest Amanda Whyte

I dont consider myself a crossdresser, but the most daring thing I have done is:

I was living with a friend and his wife, they had no kids or anything and needed the help with expenses. One time they went out of town and I snuck in and dressed entirely in her clothes. I am kind of ashamed in doing it now since I didnt have her permission. Well I was just sitting around the house, when I got the urge to go out. My bravery only went so far though because I put on a rain coat over the clothes. It was the most excilerating and free thing I have ever done.

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  • 1 month later...
Guest Madison_Always

The first time i went in front of my therapist. I was literally so nervous I was about to cry. It went fine though, but oh my goodness was that scary lol.

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Guest StephanyR

Well two weeks ago my wife and I went to Zellers. Canadian store. I always wear nylons and panties when we go out and even a bra. So there we were in the shoe isle and I was looking at some shoes. Of course my toe nails are painted pinkish and the nylons were beige. well I was trying on these high heels and showing them to my wife and she said turn around... I did and just then two girls walked right around the corner and saw me. They just smiled and walked on and smirked.

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Guest StephanyR

The next thing I know the two girls stopped and said very nice goes well with the jeans!!!! I was scared and excited at the same time. My wife looks at me and said he even did an great job on his toe nails!!! The girls wanted to see so I showed them. They were impressed and said I should try some of the womens clothes that would match the shoes. Gawd the scaredness went away and the shock of walking thru the ladies clothes with the heels on!! I said I would look at the clothes and carry the heels to the change room. I couldn't believe how accepting they were.

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  • Root Admin

Way too cool! I'm glad it was such a pleasant experience for you. I'm sure there will be many more. :)

MaryEllen

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Guest StephanyR

I hope not it was nerve racking!!! I was almost caught one other time and that really put a scare into me. I like the idea of almost being caught or even let people wonder but when you either get caught or seconds away from being caught it really gets your heart going!!!!

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Guest kimberly c

Hi Girls, I went out to my favorite lingerie store today fully dressed, when I got out of the car there were about six guys

standing around. Picture me with girls jeans, feminine top multi color pinks, breast forms, feminine sweater. necklace

and high heeled boots. Not even really a stare, just walked to the lingerie store. In the store the sales lady helped

me with new breast forms and I also tried on about six different nightgowns. I tried on a purple full length gown in the

changing room, the sales lady says come out and look in the full length mirror as I did two more ladies had entered

the store, they weren`t even shocked, both said how pretty! Caught but okay!

Love Kim

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Guest rikkicd64

I go out almost every where dressed, my experiences have been great so far, at the grocery store the last two times ,the young men sacking have even addressed me as "maam",it is wonderful. The ladies in the lingerie shop were extremely helpful and they both knew I was a man dressed as a woman, I hope everyone is able to have as good of experiences that I have had.

Rikki.....

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Thinking about StephanyR 's comment on moments that get your heart going. Most daring thing I've done is wear a bra under my sweatshirt a few years ago in the Marines. Problem is I didn't give enough thought to how subtle it would show. Marines are a tough bunch and we tended to give each other cold stares in the hallways. There were a few folks I passed though, I wonder. After a couple hours I had to change...pretty scary for me... Might be a little less dangerous now with 'don't ask don't tell' abolished.

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Guest Hollie W

I love reading how well people treat us when in shops and on the street. This is going to help me when I am divorced and will be exploring my darker side further. Thank you all for sharing.

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  • 3 weeks later...
Guest Kristi Lyn

My only stories include a night that was extremely cold and I had to work. My under armour leggings were torn up from a fight the night before. So my ex offered up a pair of her black tights to help keep me warm through the night. So after getting into my Deputies uniform I went to work in tights for the night. Arrested 5 men that night and my every thought was if they only knew I was wearing tights. The other story was just a few years ago when I started my RLE I was dressing daily but had to go to a job interview. Wore a bra, panties, and pantyhose underneath. Went through the interview and noticed the guy was staring at my crotch. Didn't think anything of until getting in the car and noticing my pant had a huge hole in them at the crotch. Least to say I didn't get the job but he got an eyefull. LOL!!!

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Guest deglerious

Sadly, I've never been out in public, so to speak, where anyone was likely to see me, although I've walked in the deep woods before while wearing a skirt with a turtleneck and jacket as well as four inch high heeled boots. Underneath was a 38J bra (with my own form,) hipster panties, a garter belt and stockings. I've probably gone as far as a mile away from where I changed.

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Guest Jamie Lynn Star

Hey! I live in a small town -main street closes at 1 am - i usally go out dressed in jeans and top boots or tennis shoes-comfy- at times its a dress and heels. One night I was really pretty wearing a dress white sttrappy heels and black hose. As I was heading home bout 3blocks to go I saw a car light behind me. as it got close I saw it was a police car I got a lil scared but walked normally when it got closer it slowed down I heard this woman say" Hey were you going?" As she pulled up and stoped I said "on my way home few blocks " She said "justt checking" and went on her way. I was so relieved that I wasnt taken to jail.. Ive been out more since . I thinik she knew me and not really worried about me being out. cause I havent been stopped since. JLS

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  • 1 month later...
Guest baily

I remeber when I was still in high school and my mom said I could take the care down to the gas station the night before we were going to go out of town. So we wouldn't have to worry about it in the morning. So I put on some drk brwn pantyhose and put them on a pair of sweats and a white hooded sweat shirt. Put a pair of heels in my back pack and a pair of high cut jean shorts. I went out to the car and got in and as I was driving I was so excited to be out in pantyhose. So I pulled into a parking lot that was vacant and pulled out my daisy dukes and black high heels. And took off my sweats. and put on my daisy dukes and black heels. I couldn't believe how sexy I felt and how good the wind felt on my nyloned covered legs. I got back into the car and drove to the gas station feeling a nervous but exciting feeling as cars passing by thinking what if they could see me wearing pantyhose and heels. As I got to the gas station there was nobody there. So I pulled my hood up so you couldn't see my face and got out. I felt so nervous but so excited and went and started to fill the car up with gas. A old couple pulled up and an elderly man got out and was looking at my legs as he was going to get some gas. As I was done. So was the elderly man who went in before me. I went in and grabbed a soda and went to the counter. The clerk didn't even notice me as he was to busy checking out the tv behind the counter. I payed for my gas. As I was leaving I said thanks and was walking out the front. I loved the way my heels sounded on the pavement and the swooshing sound of my pantyhose legs as they would rub together. As I got to the car I opened up the back door on the driver side and looked back and noticed that the clerk was looking at me. I smiled and closed the back door and climbed in the driver seat and drove back home. As I pulled in I changed before I went into the house and went up into my room and was just so excited about my out and about experience. That was one of my daring moments. Tho not as daring as wearing panties and bra in a combat zone. Which is a who new level of daring if you ask me. Very hard if at all topable.

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I didn't do anything daring. I just wanted to dress and go out, so I did.

:D

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Guest amanda_s

WOW Donnajean what colour were they, i don't think anyone can beat you. grade 12 last coulpe of weeks of school wore a bra and panties to school it was 1986 toronto. still don't know why i did it.

amanda

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Guest Marlane

I used to be in a band and one night I decided to dress en femme. I went to the local thrift store and bought everything I needed and some things just for my own enjoyment.

I found a black leather skirt that fit and multicolored sleeveless turtleneck. I stuffed my bra with tissues and bought a pair of fishnet pantyhose at a local store. I got my makeup done at a local department store and had my longish hair styled. I went to venue by myself and had a little bit of trouble getting in the stage door even with my stage pass. Any way, That night I performed before 1500 people dressed pretty much how I always wanted to. My bandmates thought it was great. But it was the 80"s, What can i say......Girls Just Wanna Have Fun!

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  • 3 weeks later...
Guest Melissa~

I went on a back country elk hunt, 12 miles of horse riding from the road, partially CD'ed with painted nails. This was a paid wilderness expedition, week long, no one said a thing even about my painted nails. The hunt was a success.

smallpackout.jpg

That was last fall, moving further forward this year.

By the time I return there I am likely to have transitioned. I doubt that's a barrier.

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      I use my  chosen name online and when ever I can. I play some online game and only go by that name. That is how everyone there know me. Yes it does feel great to be called the name you prefer. 
    • Breezy Victor
      I was ten years old when my mom walked in on me frolicking around my room dressed up in her bra, panties, and some pantyhose. I had been doing this in the privacy of my bedroom for a little while now so I had my own little stash box I kept full of different panties, bras, etc ... of hers. My mom's underwear was so easy for me to come by and she was a very attractive woman, classy, elegant. Well when she walked in on me, she looked at me with disgust and said to me... "If I wanted to run around like mommy's little girl instead of mommy's little boy, then she was going to treat me like mommy's little girl."  She left my bedroom after telling me NOT to change or get dressed or anything and returned with a few of her work skirts and blouses and such. She made me model off her outfits for her and I have to admit ... I LOVED EVERY SECOND OF IT. I felt so sexy, and feminine. And she knew I loved it.  She told me we can do this every weekend if I'd like. It would be OUR little secret. 
    • awkward-yet-sweet
      The usual social ways, of course.  Taking care of my partners and stepkids, being involved in my community.  That makes me feel good about my role.   As for physical validation and gender... probably the most euphoric experience is sex.  I grew up with my mother telling me that my flat and boyish body was strange, that my intersex anatomy was shameful, that no man would want me. So experiencing what I was told I could never have is physical proof that I'm actually worth something.  
    • KathyLauren
      <Moderator hat on>  I think that, at this point we need to get the thread back onto the topic, which is the judge's ruling on the ballot proposition.  If there is more to be said on the general principles of gendered spaces etc., please discuss them, carefully and respectfully, in separate threads. <Moderator hat off>
    • Abigail Genevieve
      People who have no understanding of transgender conditions should not be making policy for people dealing with it. Since it is such a small percentage of the population, and each individual is unique, and their circumstances are also unique, each situation needs to be worked with individually to see that the best possible solution is implemented for those involved. 
    • Abigail Genevieve
      No.  You are getting stuck on one statement and pulling it out of context.   Trans kids have rights, but so do non-trans kids.  That conflict is best worked out in the individual situation. 
    • MaeBe
      I get the concept, I believe. You're trying to state that trans kids need to or should be excluded from binary gender spaces and that you acknowledge that answers to accommodate those kids may not be found through policy. I disagree with the capability of "penetration" as being the operative delimiter in the statement, however. I contest this statement is poorly chosen at best and smacks of prejudice at worst. That it perpetuates certain stereotypes, whether that was the intent or not.   Frankly, all kids should have the right to privacy in locker rooms, regardless of gender, sexuality, or anatomy. They should also have access to exercise and activities that other kids do and allow them to socialize in those activities. The more kids are othered, extracted, or barred from the typical school day the more isolated and stigmatized they become. That's not healthy for anyone, the excluded for obvious reasons and the included for others--namely they get to be the "haves" and all that entails.
    • Abigail Genevieve
      Context.  Read the context.  Good grief.
    • MaeBe
      Please don't expect people to read manifold pages of fiction to understand a post.   There was a pointed statement made, and I responded to it. The statement used the term penetration, not "dissimilar anatomy causing social discomfiture", or some other reason. It was extended as a "rule" across very different social situations as well, locker and girl's bedrooms. How that term is used in most situations is to infer sexual contact, so most readers would read that and think the statement is that we "need to keep trans girl's penises out of cis girls", which reads very closely to the idea that trans people are often portrayed as sexual predators.   I understand we can't always get all of our thoughts onto the page, but this doesn't read like an under-cooked idea or a lingual short cut.
    • Ashley0616
      I shopped online in the beginning of transition. I had great success with SHEIN and Torrid!
    • Abigail Genevieve
      Have you read the rest of what I wrote?   Please read between the lines of what I said about high school.  Go over and read my Taylor story.  Put two and two together.   That is all I will say about that.
    • Abigail Genevieve
      "I feel like I lost my husband," Lois told the therapist,"I want the man I married." Dr. Smith looked at Odie, sitting there in his men's clothing, looking awkward and embarrassed. "You have him.  This is just a part of him you did not know about. Or did not face." She turned to Odie,"Did you tear my wedding dress on our wedding night?" He admitted it.  She had a whole catalog of did-you and how-could you.  Dr. Smith encouraged her to let it all out. Thirty years of marriage.  Strange makeup in the bathroom.  The kids finding women's laundry in the laundry room. There was reconciliation. "What do we do now?" Dr. Smith said they had to work that out.  Odie began wearing women's clothing when not at work.  They visited a cross-dressers' social club but it did not appeal to them.  The bed was off limits to cross dressing.  She had limits and he could respect her limits.  Visits to relatives would be with him in men's clothing.    "You have nail polish residue," a co-worker pointed out.  Sure enough, the bottom of his left pinky nail was bright pink  His boss asked him to go home and fix it.  He did.   People were talking, he was sure, because he doubted he was anywhere as thorough as he wanted to be.  It was like something in him wanted to tell everyone what he was doing, and he was sloppy.   His boss dropped off some needed paperwork on a Saturday unexpectedly and found Odie dressed in a house dress and wig.  "What?" the boss said, shook his head, and left.  None of his business.   "People are talking," Lois said. "They are asking about this," she pointed to his denim skirt. "This seems to go past or deeper than cross dressing."   "Yes.  I guess we need some counseling."  And they went.
    • April Marie
      You look wonderful!!! A rose among the roses.
    • Ashley0616
      Mine would be SHEIN as much as I have bought from them lol.
    • MaeBe
      This is the persistence in thinking of trans girls as predators and, as if, they are the only kind of predation that happens in locker rooms. This is strikingly close to the dangerous myth that anatomy corresponds with sexuality and equates to gender.
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