Biggest Bravest Opportunity Taken, To be Dressed up

In an earlier post we discussed opportunities not taken ! What were some brave opportunities you did take ?

These should all just be fun and funny experiences for everyone involved ! Fun Memories from the past are the Best for many of us

Most of the Opportunities missed involved Women/Girls asking to dress us in their clothes but we worried it would be to obvious we were enjoying it.

Would love to hear from those of you who were brave enough to put yourself in their hands. Were any of you actually asked to put on panties and if

so were they just plain cotton or Girly ? I just don't know How I would react to wearing a lacy bra and panty set in front of a gal or my Mother !! LOL

Also what items did the gals involved seem the most interested in ?

I really wish I knew what was going on in women's heads during these fun experiences

My first opportunity to dress was on the occasion of my 9th grade talent show. Somehow many of the boys in the class ended up doing a drag show. I don't remember much about most of the costumes (except for one guy who dressed as a scullery maid, complete with mop and bucket) but mine still sticks in my mind. My mother and sister, oddly enough were responsible for the costume and everything was borrowed from my sisters wardrobe (she was in her mid twenties at the time).

I wore a platinum blond wig, orange A line mini-dress, panty hose, and heels (it was the '60s, so my sister had stuff like this). I don't remember, but I doubt if I wore a bra or panties. It was the '60s, so flat chested was in. I did the usual waltz across the stage and my only other memory of the event is that one of the older girls commented that I had great legs (I did, and still do, if I do say so myself).

One other detail worth mention is that I attended a Catholic high school. I have no idea how such an event ever made it past the school administration.

Forced femanization is a common dresser fantasy, Robbie. So, for most of us it's only happened in our dreams!:devil:

I had heard of Amanda Rich, this makeup artist in Bethlehem, PA, who did makeovers on CDs, and I so wanted to go. But it would be two-day overnight trip and I didn't know how to do it without telling my wife about it. So, I concocted a business trip to Philadelphia and, naturally, told my wife about it. Phili was close enough to justify driving instead of flying, so I chose to drive.

It wasn't cheap, but it was the best money that I ever spent.

My first wife once encouraged me to try on her bra and girdle. It was an amazing experience that I obviously enjoyed, and in doing so revealed a part of myself that I had not discussed with her.

Beauty salon experiences have always been my favorite CD activity. One year I made an appointment at a salon to get my hair done femininely and to get a set of acrylic nails. Sorry to say I used the 'lot a bet' excuse. Of course, I'm sure that fooled no one and the 4 hour experience I received pretty much showed that they were willing to give me my money's worth. I gave them a picture of a curly hairdo and the hairdresser cut my hair a little and rolled it up on perm rods. i was sure worried about the cut and if she was going to perm it. Then I was put under the dryer for about 45 minutes and a girl rolled a nailcare table up to me and gave me my full set with red polish wile I was under the dryer. After the nail tech finished up, my hairdresser took me to her station. She complemented my nails as she took out the perm rods. Then she spent a long time with a curling iron softening the vey tight curls. Along the way she used a LOT of hairspray. Mu new 'do' wasn't all that great but it was a terrific experience!

I went to New York City a couple of years back, before the pandemic. I went to the 9/11 memorial and the American Museum of Natural History completely en femme. The greatest thing was riding the subway. I got to sit down all the way!

I was wearing a red knee-length knit sheath dress and a burnt orange leather jacket (in October).

The lady at the admissions counter at the museum clocked me (I think), but I was giving her money so I didn’t really care.

I also went to a couple restaurants.

I was a bit hesitant before stepping out of my hotel room, but after that first step, the inner woman took over and I owned it. This is what usually happens when I go out en femme, even though I’ve gone out hundreds of times.

I was volunteered to represent my workplace in womanless beauty pageant. I am single and about 50 years old at the time. I was determined not to miss the opportunity though I was scared to death of what would be said.

I wanted to look as good as I could. I shopped for my own clothes and shoes. I doughty a white and black bias hem dress and 3 inch heels. I did my own makeup. I confided in a female cousin so I could tell everyone she did my makeup. She drove me to the event and took pictures . I won Miss Congeniality. It was unreal to be in front of maybe a couple of hundred local people, many of whom knew me. I received many compliments and I am sure some people figured it out but there were really not any repercussions. I have been out ot town dressed many times since but this time being local really took all my courage!

That's easy...
In the late 90's (not really sure when), while still identifying as a crossdresser, my wife and I decided to visit Las Vegas and include at least one night out for me as Kelly. This would be my first time out in the real-world public (as opposed to the semi-cloistered environment of a support group dinner out.
She helped with my makeup and wig, and when we were satisfied, off we went. I don't recall much of the walk to the elevator, nor the trip down to the lobby. I was petrified. When we stepped out and away from the small crowd around the lifts, my wife took me by the hand and said, "Breathe..., and smile". This I did, and found I was able to walk and actually, finally, take in what I was seeing, typical LV Strip casino; crowded and noisy. As we moved along towards the restaurant, most of the crowd didn't seem to notice anything but two middle aged ladies, which are a dime-a-dozen in LV. But every tenth couple (or so), would stare, mouths agape, turn and whisper to each other, and then turn back and stare some more. Some even pointed, mouths still agape, of course. To say that this was unnerving would be an understatement
Then, an amazing thing happened. My training must have kicked in, and a found myself doing a quick threat assessment. "Safe environment (casino security will defuse a disturbance in seconds), most folks just ignoring me, and the occasional shocked tourist... hmm, tourist." I realized that Ma and Pa from Nebraska were out of their element and shocked to see something so decadent in Sin City. And just like that, these encounters became sport. With each one, I'd give a smile, a wink, and maybe a wave. Their reactions were about a fifty-fifty split between even wider-eyed shock or a suddenly averted gaze.
I would come to realize that the locals and the regulars had pretty much seen it all, hence their almost universal non-reaction. Ma and Pa though, were endless fun. They still are today, on the rare occasion when I find them staring at me from across the restaurant.

The two boldest (vanilla) things I have done dressed is 1) fly to Chicago for two days as Monica, spend 95% of my time there dressed, and then fly back. Changed back into drab wear at the airport. The remaining 5% of that time was spent attending business meeting, and 2) go on a fantastic date that started with a fancy dinner at Top of the Hub in Boston, followed by a pops concert, and ending with cocktails at a fancy lounge. Heavenly.

One of my girlfriends always wore cute maidenform bra and panty sets and had several in baby blue. She would come out of the bathroom with a towel wrapped on her head in her pretty underwear almost everyday. Well one morning she had her folded laundry right next to my side of the bed topped off with lots of her bras and panties , well I decided to go for it and put them on , they felt wonderful. I then wrapped a towel around my head and went in the bathroom and asked to borrow her hair dryer . OMG she fell over laughing and then later chased me around with her finger nail polish ! LOL She said i looked to good in her undies ! Great time

Unfortuntely I tried something similiar with another lady but the surprise did not go quite as well ! I think this cartoon represents pretty much her reaction ! LOL

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I had a girl friend in college that I had told that I like to wear panties and lingerie, but I seldom did it around her. I bought her a red satin cami and tap panty set and asked to borrow it every once in a while and she let me. but I didn't tell her when or if I was wearing it. One night she was in the shower and I asked her if I could do something I always wanted to do and she said yes. I put on the cami and panties and got into bed. When she got out of the shower, she turned out the lights and got in bed with me and ran her hands all over the satin and held me close. That's been the only time.
My mother thrived on controlling me with guilt, shame and fear and there was a period of time when I was a kid, when I did something wrong, she would threaten to make me wear her panties. I don't think it ever happened, but i did sneak into her's or my sister's panties just to see what was so bad about them. I guess it backfired on her. She found a pair of panties in my laundry when I came home from college and told me I was sick.

I remember early in my full dressing mode about 3 years ago I went to me grocery store during the day to shop for groceries.

I could not do makeup and hair yet. I must have been a sight. The things you do when you have no fear.

I could go now but I am smart enough at least to go to a store that I do not frequent 2x a week.

When I was 8 or 9, the neighborhood gang of girls would play a game they called Catch a Boy and Put a Dress on Him! I was not the fastest boy on the block but also was not the slowest. For some strange reason I got caught way more than any other boy and got to wear that green (or maybe blue) satin dress that smelled like it was out of their grandmothers attic. But it felt amazing. I still wonder where those girls are today! Maybe out feminizing their husbands! Lol.

In June of 2020 I was complaining to my wife about something (had nothing to do with us and I've long since forgot what it was). Anyway, she told me to put my big girl panties on and get over it. I thought about if for a couple of days and took her advice. It took me 5 months to tell her I had started wearing panties as a result of that conversation. That's one of the few times I've taken her advice so literally and I'm so glad I did.

When I came out to my mother, she asked to see me dressed.So I obliged full dress , wig bra , panties , nylons and high heel shoes.She was ok with it which resulted in me dressing at her house at least once a week until she passed away. I also kept a wardrobe there . She was very accommodating. However she did refuse to call me by my fem name Debbie.

Robbie, that cartoon is spot on.

Hard to answer a question like this. Just about every step of the way was a big brave move at the time. Now in retrospect it is small in the over all picture. Just one step on the journey.
I think that's the lesson here. Some milestones were the first things I purchased in the mail then in store, first time anyone saw me, first time in public, going to a support group meeting, letting my hair grow, Riding the train to the city, first time I took a plane. The list could continue.
It's like that image of a circle and inside is labeled comfort zone. Then just outside the circle is a dot labeled really fun experiences. Many fun things we do and experience in life are just outside our comfort zone the first time we do them. After that, we expand the circle of our comfort zone to include them.
If I had to pick something, I'd say laser hair removal (full body) was quite a big step. There is no going back. No regrets either. I think this question is asking in a round about way, how big is your comfort zone?

so true Genifer and well said... my comfort zone is ever expanding and my only limitation is myself. I've never bought myself a pair of heels, and today I went to a local thrift shop and boom, done.. no problem, no one cared and that's awesome.

Our church had a WOMANLESS BEAUTY contest a few years ago.---about 8 or 10 other guys were in it including the preacher. I was asked, so I did it too. Since I was not the only guy, I felt "safe", so why not? Besides, I thought I might pick up a makeup tip or two from the teenage girls who did our makeup. ;) (Turned out, I could have done a better job.) I wore a curly long blonde wig and a long purple gown with heels. It was rigged---our 86 year old retired preacher won---But we were all happy and had fun. I did notice an odd thing. A couple of the most UNLIKELY guys (overweight and another old) look remarkably convincing---Not "Pretty", mind you, but realistic. that I did not recognize them when I walked past them as we were getting ready for the event--Remarkable what the right clothes and some makeup can do. There are no pics because the cameraman forgot to put the SD card in the camera--the video was gonna be shown on the next Wed Nite supper. Not EVERYBODY was unhappy. ;)

The first time was when I was 3 or 4 There was no boys my age to play with only girls. One day they wanted to have a tea party with no boys. So, they kept me out I started to cry so the oldest girl(who was about 6) said to get her sisters dress and lace panties and dressed me up. Thats when I knew I want to dress like all the time.

Second time I was in Boy Scouts, and we had to do a show for the parents. Since it was all boys in the 50's and they need a girl for a skit I was elected because I was the smallest. They me put a bra and ruffle lace panties a petticoat with lots of lace nylon hose with Garder belt a silk blouse a full skirt and heel highs. Then they put makeup on and a wig. I had my back to the audience as another boy sang to me a love song. When the song was done, I turn to the audience wearing a Groucho Marx glasses eyebrows and mustache and false teeth. After the show I stay dressed till I got home didn't want to take it off until my dad made me.

Glenda, if your scouting story is fully accurate, I'd have to say that I'm suspicious that there was something more than just a scouting skit going on.

Why on earth would you need to be put in panties, bra, garter belt, or anything that wouldn't be seen by the audience?

Did you get PUT in these clothes, or were you "given" them to change into in private?
Did anyone get to see what you were wearing under the blouse and skirt? Who and why?

I'm glad you liked the experience, though.

I too was dressed up for a scouting skit - but I was just given an oversized dress to throw on over my boy clothes and a mop head to use for hair.
Far less questionable - but yes, I loved even that little bit of "girlie-ness."
And no, it didn't stay on. Sadly, as soon as the skit was over, off came the outfit.

@SaraLin;

As I walked off the stage, I flipped up my skirt with my back to the audience so to show them my ruffle panties. everyone had a good laugh.

For me, the bravest opportunity we take has got to be our first. Mine was to attend a dressing service where I fully dressed including wig and make up for the first time. Nervous as hell to begin with but put at ease by the two GG assistants. I enjoyed 4 hours of being a girl including mixing with other customers browsing in the shop or experiencing the dressing service themselves. I can't wait to experience it again.

About 11 years ago, my wife bought me a series of six, one hour burlesque classes. She came along for support, but the entire class was women except for me. She made sure to contact the instructor first and make sure it was OK for me to be there. The first class was learning how to "strut" in heels. I think my wife was more nervous than I was and thought I should just wear my regular shoes. But I wanted to learn like everyone else, so I popped on my heels and did the lesson just like any of the other girls in class. Lesson two was a stocking peel/chair dance. In later classes, we learned bra removals, feather boas and fans classes and the final week we had a class recital for friends and family. It was awesome and I became good friends with some of the girls who I still see and dance with today. We occasionally reminisce about those first classes and it made some of the women happy to see that I was there not to oggle them but to participate. Some also said it helped them; if a guy is brave enough to wear and do a stocking peel, they shouldn't be self conscious about it either. I love my burlesque gal pals.

I've had a few.

Walking the streets of San Francisco to have a makeover at Sephora, then a year later locally at a mall. Taking the train from St. Louis to Chicago, and then seeing Hamilton. Seeing U2.

Lately, letting my GG friend Michelle post this picture on her Facebook page on Halloween.

My girlfriend in HS who later became my wife, first saw me dressed on our 3rd date. She saw how happy it made me and from then on always encouraged me to dress.

This past Saturday when I went for my first makeover. I was very nervous but I am so glad I did it! The best time I ever had in my life!!!! Nervous as hell beforehand, but so calm and relaxed afterwards!!!

Halloween, and I loved it!