do you dare yourself?

[jacques]

hello,
Do you dare yourself sometimes in your dressing to push the boundaries or try something new?
Like today - when I went to our favourite cafe with my wife, I was under dressed in a strappy vest top, pink patterned panties, fishnet tights and grey ankle socks with lace tops. No one seemed to have noticed and the world did not come to an end. Yet I knew that I was pushing a personal boundary.
Do you ever feel the need to dare yourself?
Luv J

[Teresa]

Jacques,
Do you know a CDer who doesn't ?

We may dress as females but underneath we are some tough cookies ! What we do does takes balls sometimes , OK some are big steps and some tiny ones but we never stop taking them ! Some one asked recently on the forum are we crazy ? Well maybe a little !!

[DIANEF]

The first time I ever stepped away from the car. It was a real 'you can do this' moment. There have been others, but that was a biggie.

[Tracii G]

Did you have male clothes over what you just described?
If so then how would anyone know what you were wearing?
Hence the reason no one noticed and the world didn't come to an end.

[Stephanie47]

I would not call it a "dare." Sometimes it takes some encouragement. I always look at something with the attitude of "risk vs reward." You tried under dressing. I gave it some thought. The negative of under dressing may be being discovered after a serious automobile accident or a heart attack wearing a bra, panty, garter girdle and stockings and a camisole under my guy clothes. That was my under dressing attire. I gave it a try and found there was zero enhancement of any feeling of femininity. It was actually a major inconvenience to go to a public bathroom, especially if I was wearing pantyhose. Fix that bra strap. I don't under dress anymore.

Decades ago I tried getting dolled up at night and taking a drive. It expanded to parking the car and taking a stroll. I carried and still do carry a bag of my male clothing. If my car breaks down I want to be prepared to change. I did desire to interact with humanoids, and, did that on several Halloweens. Mixed reviews. There is always the element with my evening strolls that I may have a reason to end up in an emergency room. Again, "risk vs reward." I minimize the risks, but, there is always the element of total disaster. Is it work the public ridicule? Embarrassment? Marriage breakdown?

There is a lot of urging on this site to try something. What may have worked for one does not automatically mean it will work for another. Just remember, when someone "dares" you to do it, you are the one left holding the bag..the consequences of your action.

[susan54]

With me it was not so much dares to myself as a bucket list of challenges. I ran out of these years ago and do a lot less dressing in public now. For most people the first time fully dressed in public (nocturnal walks to the post box do not count if no one sees you) is the big one - and when you realise that no one cares the rest is easy.
The challenges included (all fully dressed): out for dinner, theatre, concerts, shopping for clothes and using fitting rooms, bra fitting, personal shopper, 5-days stay in hotel, visits to tourist attractions, leg waxing, pedicure, makeover, colour & style consultation, using ladies toilet (only when necessary, not purely for the challenge), dinner and coffee with female friends, swimming in hotel pool in swimsuit, spray tan, hot tub, having a dress made for me, fashion show. For things like the toilets and the swimming I asked permission first (they knew I as male, as most of the people I encounter as Susan do). The one challenge I did not seek was meeting someone I knew. I even got a kiss on the cheek from her and was not recognised. I do a lot of my clothes shopping as a male and shops in Scotland are quite happy for you to use the fitting rooms. I repeatedly use the same shops and no one has ever even discussed this with the shop staff let alone complained about it (I have asked). One SA even said that if anyone did complain they would be asked to leave the shop. I have never encountered a communal changing room (I hate sport) and if I did I would instantly leave - where woman feel comfortable letting other women see them undressed or in their underwear should always be a woman-only space and a crossdresser is not a woman - the situation is different if you are TS. The world (well the UK bit of it anyway) really is cross-dresser friendly though I dare say you could find problems if you look for them such as going into bars where the customers have tattoos.

I would not regard underdressing as a challenge. I wear panties and tights under my trousers because they are more comfortable - as no one is going to see them there is hardly a challenge involved. If you have an accident and end up in hospital with pretty underwear and painted toes your underwear and toenails are the least of your problems - the real problem is the damage that requires hospital treatment.

Challenges are good. Dares are in a different category and can be stupid if something can go wrong.

[Helen_Highwater]

I suppose daring ourselves is as good a way of putting it as any. It's that "You can do this" moment when you do something that expands your CD'ing world.

Certainly for me it was the first time in a shop dressed. Sat in the car looking towards the shop doors, glancing around to see who was near, butterflies crashing around in my stomach. Then there's that moment, you take in breath, reach for the door handle and step out. Next thing I know it's coat on, bag on shoulder and I'm through those doors. As Jacques said, the world carried on, I lived to tell the tale.

It would be hard not to agree with Teresa; What we do does takes balls sometimes so man up and get on with CD'ing.

[Princess Chantal]

I don’t see it as daring or challenging myself, more of wanting to experience my curiosities and see if it is something to put into stuff to do to keep the crossdressing fun. Like after purchasing my first Victorian type dress and props for the main purpose of an Halloween costume. Then being curious on how it would be to wear it for the steam train ride (tickets bought prior) the following weekend. So went out and gave it a shot, finding that it definitely is something that I wanted to do more of and have done lots of since.
I am like a “Just do it” type of a person!

[Jenny22]

I don't see a dare. I feel a 'have to': outside (twice) coffee with a sister, stroll in a vacant parking lot on Sunday, first drive through for food, two evening walks from a parking lot to a restaurant, a day time walk from a street parking to a house, strolling through a supermarket with a forum sister ... all of these because I had to. Yet, I still have a reluctance to go out solo. I hope this will change after DLV.

[Alice B]

I have been challenging myself and my wife lately at home. I bought some new forms and a couple of pocket bras and have been wearing them to bed and at home most of the past few days. Wearing just regular clothing, no make up or wigs. Just me in a bra and forms that are very obvious. Nothing has been said by my wife, which is a major change in attitude.

[docrobbysherry]

Since I'm a closet CD, I'd say my outings began as, "Dares". But, in the last 4 years I've done things I could never have imagined in my wildest dreams. :D

So now, it's more like Chantal says. (Who has been my inspiration since many years ago. But, don't tell her!)
Now, it's just trying things Sherry's not done yet! Which r becoming harder and harder to find!:straightface:

By the way, Jacques, my "underdressing" stage started and ended in under 2 months!:battingeyelashes:

[Aunt Kelly]

No, I don't "dare myself". I'm not an exhibitionist.

[Princess Chantal]

Oh, Sherry we inspire each other for years!

[2B Natasha]

I don’t now. But I did. When I first felt the desire to take a leap in my presentation and going out. I did dare myself.

I had been dressed up and ready to do it many times. Out for a drive or a late night, like 2am walk in the winter. So I could really cover up completely. I went to a TDAR event in a city away from me. But I could never get out of the car or go in the store or anything. I decided at some point. That I just needed to do it.

To that end. I found a woman on here that lived nearby. Set up a time to go meet up with her. Scared to poop outta me. How was I going to do this! Well. I decided to set up a makeup appointment with a makeup artist to show me what and how to do makeup. Forced myself to go buy clothes. All by daring myself. But that was the easy part. Going to the club we had agreed to meet at was going to be the worst part. All my fear I knew would come to a head. So I decided that I would pack a just in case bag. NO BOY CLOTHES IN THE CAR. That way I figured if something happened I had to stay dressed. I did it. The whole night went fine. Since then. I haven’t had to dare myself to do things. But those first times I sure did.

[MarinaTwelve200]

I've only been OUT a couple of times----Once as a "Gypsy fortune teller" for our Adult Sunday school Halloween party, where I thought I would force and help revive our costume tradition which was falling off (It worked) And secondly as a Contestant at our Church's "Womanless Beauty contest"--A chance I couldn't pass up, especially since 7 other guys were doing it too, gave me "cover". Also I thought some of the real girls would give me ideas for makeup I hadn't thought of, when they did me up.---(Turned out I could have done a better job myself).-------STILL, it took "Bravery" on my part, both times---"Taking a chance" and being rewarded with new experiences (and Highs).

[IamWren]

No, I don't "dare myself". I'm not an exhibitionist.

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what she said

[Lana Mae]

I don't literally dare myself but I do challenge myself! If you do not then you are stagnant and can not progress! Without the challenge to go out that door, you will stay in the closet! It is your journey and you will progress at your rate and you must reach certain goals and they can be a challenge! Just my $0.02! Hugs Lana Mae

[Nikki A.]

The last "dare" I have is to tell my kids. I regularly go out, attend church and have been seen by my neighbors so I guess I'm pretty content. I do dress conservatively and am beyond the age and have no urge to dress sexy. My ideal for Nikki is a nice knee length skirt or dress, nice top and a good make-up job.

[Aunt Kelly]

I know what you mean, Lana Mae, and you're absolutely right. There's a big difference between doing something "daring" and pursuing something because it can improve ourselves; physically, emotionally, spiritually or whateverly. I get that it's easy to argue that a crossdresser is an exhibitionist by definition, but I (and I'm pretty sure, you) don't look at it that way. The satisfaction I get is not attached to the clothes, or the makeup and hair, and it's certainly not dependent on getting some "thrill". Not that there's anything wrong with thrill seeking. Pick an extreme sport and I've probably done it, but for me, at least, gender expression has never been about the thrill. Don't get me wrong. I know that there are those of us who do, but that's just not me.

[Tracii G]

Daring yourself sounds kind of immature.
Set a goal and succeed is a better way to think of it.

[stephNE]

I do like to challenge myself. My wife likes to challenge me too. When she notices something I do, or don't do, she suggests things that I should try.
A while back she noticed that I always carried a purse with shoulder strap. So she suggested I get a hand bag (hand grips and no shoulder strap). It did take a bit to get used to.
Last fall she also asked me if I had ever worn a posture bra. I hadn't. So for Christmas she gave me a long line posture bra. It holds my shoulders back, and boobs out in front - really on display. I've only worn it out once, it is definitely something one has to get used to.

[Tracii G]

Challenge is a good word for it too well done stephNE.

[docrobbysherry]

Who r u calling, "immature", Tracii!?:straightface:

290198

[Beverley Sims]

I just think the expression is incorrect.

I am constantly pushing the boundaries and experimenting with new looks.

Wigs, dresses, tops, skirts and jeans.

Yes some outcomes are disastrous, but life is an experiment.

[Sara Jessica]

Do you dare yourself sometimes in your dressing to push the boundaries or try something new?
Like today - when I went to our favourite cafe with my wife, I was under dressed in a strappy vest top, pink patterned panties, fishnet tights and grey ankle socks with lace tops. No one seemed to have noticed and the world did not come to an end. Yet I knew that I was pushing a personal boundary.
Do you ever feel the need to dare yourself?

Your tree fell in the woods where nobody was around to hear. Oooooh, edgy!

[2BArianwen]

Hi Jacques. You said it was "pushing a personal boundary," so I would congratulate you. Well done. Now, on to the next one...

Rian

[Sarah Doepner]

Dare is as good a word as any for that internal conversation that drives us to the next level. Some will call it a personal challenge or setting a more difficult goal, but in the school yard that was a dare. I've done it any number of times, but rarely called it a dare. It's usually self-described as "This is something I need to do but don't know if I have the courage." One time it was leaving the house in the middle of the night for a walk in the back yard. Another it was standing in line for the ladies room behind a woman with her young daughter (and I REALLY did need to do that one).

However we try to motivate ourselves it seems to always be toward growth in one way or another. The question I have is what drives that need to dare, challenge or set a more difficult goal?

[lingerieLiz]

My liberating dare was to go out with a friend as his date back 60 years ago. What started as a joke entry in a contest kept expanding. Originally, I figured that I would go as an amateurish impersonation. He pushed to go seriously all out. My landlady knew I was a CD and she was a beautician. She offered to do my wig and help with any other things I needed including my makeup. We decided to go as a beach party couple. I tried to have a Sandra Dee look. I grew up wearing my sisters' clothes and dancing as a girl. So I was comfortable wearing a dress and even dancing as one. I had the petticoats and bought a dress that would fit the occasion. We went in a convertible to the event. We ended up winning one of the prizes. No one caught that I wasn't a girl which was very good for me back then. Being a small guy helped.

[Tracii G]

Liz I loved that story. Sounds like you had a great time.
When I was 15 I went to the high school prom as a girl. My girl friends I grew up with coaxed me into it as a gag.
It was my first time dressed as a girl.
This was the late 60's and my hair was really long so they did my hair and piled it on top of my head like they did theirs. Had an extra gown and shoes that fit me so off we went to the prom.
It was a lot of fun.

[Hell on Heels]

Hell-o Jacques,
Every outing seems like a personal challenge.
If you can...think back to your very first outing, while
on your current outing, and realize how far you’ve traveled.
Much Love,
Kristyn

[sweetdreams]

All the time. The last year has been a series of hurdles and pushing the envelope. Pretty much without exception all positive results.

I've gone for a makeover/makeup instruction three times. First in drab and then fully enfemme. This was in a salon where I was surrounded by girls and makup artist all working on making people look pretty. Wow - mind blowing.

On the way home from one of these sessions (the first where I was fully enfemme and makeup on) I headed to one of the busiest local malls. Cruised through there with no real fuss or muss.

Started attending local CD support group on a regular basis. Fully enfemme of course. After every meeting we hit an LGBQ friendly bar. Super friendly and supportive. Once we hit a restaurant for supper. There was about 8 of us. A few raised eyebrows but nothing serious.

Each CD meeting I've tried to push the envelope. Stopped in at a liquor store and made a purchase. On the way home stop in at the local supermarket. Really nothing bad happened. Went about my business as I needed too and no one really cared.

I have more things in mind for stepping out. Learning a lot from members of the local CD group. No one has had a mob with torches and pitchforks chase them. Really very little issue with stepping out. I'm still building courage but I keep pushing.

[Rachelakld]

Sometimes it's a bit edgy (Dare) - 290216

Sometimes, it's just normal life stuff -290217

[Krea]

I guess i don't think of it as daring myself, but more as a gradual progression of what i want to do.

[t-girlxsophie]

Perhaps Dare is the wrong word,but what you did seemed to yourself as a huge step so fair play to you.But for me I don't see any new experiences I go through as Dare's but landmarks on my road to being happy as Sophie,so if it all stopped tomorrow I'd be happy with what i have achieved, but I hope there's many more landmarks to come

[DaisyLawrence]

I do not understand your description of your underdressing in relation to pushing boundaries. I mean what you have on under your clothes is irrelavant, surely. How would anyone know? I dare you to let someone see the fishnet tights next time.

[Michelle Crossfire]

Everytime i go out, i consider it pushing the boundaries. I think that is a statement that summarizes it up for almost any CDer

[Aunt Kelly]

Everytime i go out, i consider it pushing the boundaries. I think that is a statement that summarizes it up for almost any CDer
Not for me. I don't look at it like that at all. Yes, I realize that from a certain point of view, anything a TG person does can be said to be pushing (or crossing) boundaries, but for many of us, that's not the perception.

So how is it that way for you, Michelle (if you don't mind my asking)? What boundaries are you pushing when you go out?

[Shely]

I have been stepping ever so slightly out of the drab for a while. several short rides and walks in full dress. and i always underdress. My jeans are all skinny women's. I have several long sleeve blouses that i wear around. They came from the women's department but don't look overly feminine. And i am constantly thinking how to inch a little more into the female side of dressing full time.

[Dana44]

never dared myself. But maybe challenged myself once or twice.

[candice.aihara]

I'm a sporty / athletic kind of person so, yes, I pushed the boundaries. At my gym I wear feminine athletic apparel: bra top and crops, or an over-sized shirt and tight. On my feet are some sleek and soft coloured running shoes.

[jacques]

hello All,
many thanks for your replies,
luv J

[Scarlett398]

Yep Jacques...Just dared myself last week when I went right out on the front porch of our new dream house in our new neighborhood while full up girled up as Scarlett and took about seven photos of me as Scarlett in broad daylight while everyone was coming home from work. Luckily, no one drove by while I did all seven of photos of Scarlett! How's that for a dare?

Super question by the way! Sincerely Scarlett :heehee: