What Was your Best & Worst Experience of being seen by a female in Girly Items

Looking back, my first time being dressed was the best since it was shocking on so many levels. As I have told on many occassions my mother and Aunt dressed me as one of my sisters to fool an old nanny when I was about 7. So my sister wore my clothes and i was put into one of her Lucy style short dresses. Well my sister dressed as me got very little attention but I was overwhelmed by my sisters and the adult women using words like adorable, precious, cute . This went on for several hours, and worst of all when I saw myself in the mirror i looked just like a Girl !


In my early 20s I went to stay with one of my dads sisters while I was on a trip. In the guest room I was staying in it turned out she had extra dresses and a few lovely full slips. When she left to go shopping i couldn't help myself and put on a yellow full slip and a floral dress. Well she had forgtten the credit card she needed and came back and caught me as I was struggling to unzip the dress. Well she howeld with laughter and used the same words, like Darling and precious but in a very mocking way and of course told me she should take me dress shopping. The rest of the time i was there she teasingly threatened to tell my family. Well she never did but I was always scared it would come out when she was around. She would always ask how I liked the dress she was wearing and wondering when I was going to visit again.

There were many more experiences that were good primarily because I lost Bets on Purpose

This is an interesting question because in my case, the best and worst experiences were both in the company of the same woman.

Worst experience:
The very first time my wife (at the time) caught me wearing her nylons. She was not amused to put it mildly. Lots of name calling, coupled with angry accusations/assumptions.

Best experience:
Several years later after our divorce, my ex-wife and I briefly reconnected as friends. We went shopping together multiple times and she actually suggested a french maid outfit with patterned hose. She eventually gave me my first (and only) makeover and stayed for the fashion show

Worst? It seemed like the worst time when my second wife finally agreed to see me dressed. She was calm but very clear that this was more than she could deal with. A few hours later, back in drab she apologized and suggested that it was just clothes, afterall, and I was able to dress around her without objection. The actual worst moment came 18 months later, when she told me she wanted a separation and suggested that I move out.

So many best times, so I'll give you the top 3.

The DC girls "social club" that I'm in meets in the lobby and restaurant, so there are often muggles around.

1. The best ever time was when 4 GGs came up to me and one said, "You girls look like you're having such a great time." "How do you do it?" It took me a couple of seconds to clue into the question. What she really wanted to know was how do I get boobs. So, I took them out, and let her try them on. Then, the second girl wanted to try them on also. By the time they were done, all 4 girls had tried them on.

2. One Halloween we went on a bar crawl. I was dressed in a Hooters costume. What's the second bar we go to? A real Hooters. One of the waitresses asked me if I wanted to go around with them and take orders. I didn't, but probably should have.

3. I was at Keystone and out to dinner with about 30 girls at Carrabas. After we paid the checks, our waitress came around and started talking to us. She said that she was bisexual. I told her that I could be her best friend. I could be a boy when she wanted a boy and a girl when she wanted to be a girl. I invited her to come to the Gala Ball on Saturday night. She did. I actually had a GG date for the ball.

All true stories, and I have witnesses to each of them.

It's hard to pick any single best or worst moment - but here's what I've come up with at the moment...

WORST - probably the time I encountered a bunch of giggly teenage girls at the mall. Whispering, pointing, laughing, etc. I beat a hasty retreat and swore I'd never do it again. Needless to say, I didn't keep that promise.

BEST - I guess I'd have to pick the time I was out at a club with a girl I was dating. We ended up sitting across the table from each other, and I felt this foot sliding up my leg and under my skirt. :eek:
The smile on her face told me who it was.:devil:

The worst was when I was about 10 and my aunt caught me in her clothes while I was visiting my cousins. She never said anything to anyone that I know of but at that age it was horrible.
The best was when I first dressed fully for my wife after I came out to her. I had shaved everything for the first time and was dressed with full makeup. The first time ever with anyone and I expected the worst yet she made it the best.

Best: When I bought my 1st dress from a CD friendly dress shop recommended by support group years ago. I was looking through the rails when the lady that owned the shop asked me if I would like to try some dresses on. Of course I did complete with wig nylons and high heeled shoes. She asked me to show ,her told me I looked beautiful and recommended accessories. I bought the dress, a scarf and a handbag. Worst : Same shop was trying a skirt on in changing room when a lady customer came in with her husband. Felt so frightened. Seem to take an eternity to leave. Eventually did before I left the changing room. I became a regular customer until the shop sadly closed. Wish it was there now . So helpful, inclusive and non judgemental.

Best when seen by a woman was probably when my ex girlfriend dressed me up and did my makeup. She was totally accepting and would lend me her panties and the like to wear. It was great.
So far I don't think I have had a terrible experience. When my wife and I first married she would even let me wear her panties. I guess that is the "worst" experience which was actually a very good experience. :)

Odd that I can't recall a bad experience dressed in front of a GG.:battingeyelashes:

But, I certainly recall my worst of all time. At a T girl event in Vegas one of "us" saw Sherry for the 1st time and screamed at the top of her voice in the heavily populated pool area, "OMG! That's the most ----d up thing I've ever seen!":eek:

My worst experience was when my wife came home early and caught me dressed in everything bar dress, wig and makeup. Even though she knew I dressed and bought me panties etc... she had never seen me dressed before. Her comment that I looked ridiculous hurt me a lot.

My best time was shopping for a full OBG. Upon entering the store I informed the lady what I was shopping for and she was extremely obliging. She chose a few for me to select from and I took one into the changeroom. It was a fraction small and so she handed me the next size up. It fitted beautifully. She asked to see how well it fitted and agreed it was the size for me. I wore it out of the store and felt a million dollars that day as I went about my business all the time knowing what I had on underneath.

Rachael, You did it correctly going to a store and shopping in person. I feel shopping in person with an accepting SA is awesome plus you get the correct size you need.

Best: I have had many good experiences, so many that a best one is difficult to say. Shopping, sightseeing, going to theatres and concerts, dining and music bars, traveling by bus and car...

Worst: coming out to my wife. A truly idiot thing to do. Forty years and counting of trouble. Second worst: Shopping for women?s clothes in drab twenty years ago in downtown St. Louis at Dillards discount store. I was just beginning to venture out of the closet at the time. I found a few items at this Dillards and went to a dressing room to try them on. The dressing room was in a section of the store that was ?closed? to customers, though I failed to recognize this. Just as I was finishing up, a sixtysomething SA showed up and started forcing the door open while shouting and calling for backup. I held her off with a foot under the door until I got all my drab clothes on. By then, her backup help arrived and forced the door. I dropped everything, bolted quickly down the stairs, and out to the street. I was down the block and around a corner before I checked to see if anyone followed me. No one did. I never returned.

My best was being invited to try dresses on in a bridal salon.

My worst, having a woman scream there's a man in the dressing room.
She was a customer that did not know that my girlfriends and I were trying on evening frocks and I had taken my wig off to put dresses over my head.
Not really bad but quite funny afterwards.

Just thought of another Best...
I suppose I was about 22 or 23 and mustered the courage to go to NYC and Michael Salem's TV Boutique.
I guess all I expected was a clothing and accessories store, but I found it to be so much more. When I selected items I liked I was approached by one of the "girls" and she made me feel so at home and asked if I'd like to try the items on. Of course I said yes and she and another sales girl fawned all over me, helping me with the corset and then finding other items for me to try. All the comments were how "darling she looks" and "with a little makeup she'll be gorgeous" and such.
It was such a wonderful experience for a young girl like me. Of course I spent more than anticipated, but it was so worth it.

These good examples really make me want to come out to a decently close female friend I have, but unfortunately we've grown apart the past few months or so, so I don't know if its a good idea.

Really , was in the girls , my very first time, was bricking it, a girl came in and said, "lend me your lippy love" used my lipstick threw it back and walked out, just left me stood there opened mouth

My best was my girlfriend bought me a cami and tap pants set that I could wear under my cloths and sleep in. Also gave a black bra and panties with a black slip.

The worse was when she got mad at me one night she went out front of our house and yell that I was a Cross Dresser as loud as she could.

I was caught by my mom and sister, both times wearing my mom's prom dress. One time I was sitting on the ground reading and my mom walked in on me, I didn't have time to react. I had never felt so vulnerable in my life. Another time my sister came up the stairs and I thought hiding in the closet was a good idea, sort of ironic looking back lol. Another time I lost a bet to my sister and had to dress up, of course it was on purpose lol :shush:

Zoey , welcome to the Forum.

Would love to hear what reaction you got from your mother and sister seeing you in the fancy dress ! Were they mad, or shocked, or find it funny ? What sort of questions did they ask ?
I was always losing bets to girlfriends, did your sister just make you wear a dress or was there more to it ?

Thanks

Best? having a wife that was not only fully supportive but actually nurtured me. Living for almost 5 years as a woman, dang..the list could go on...until she hit meno-stop (not menopause, meno stop). Suddenly she hated it.

Worst? It was maybe 15/16 years ago. I hadn't been out good and solidly 'fem' for years. It was hard to actually as I now had a mustache (that my wife loves). It was the pink fog I tell ya. But the wife was away and the fog hit that morning in a fury. I do still keep myself shaved so there wasn't doing something that she would notice and go BANG over that wasn't a problem. I had a mountain property to go inspect for a bank (vacant and very rural) so I put on a black/white striped crop top, black mini skirt, and white block heeled platform sandals with white bra/panties and a garter belt with tan hose under - I might add the garters stuck out about 3 inches past the skirt hem. Full makeup and put some curl in my hair to boot with the curling iron. I did the drive-thru at a sandwich shop close to where you start up the hill to the property for my pending lunch. I went to the property, got the inspection done, then stopped at a park on the way back. This park I have stopped at many times. In almost every case, I was the only one there. There have been many times I was wearing a very fem blouse and never saw a person. The same was for that day. I got there, no one there, so took my sandwich, big drink and book and headed for a table to sit and read and eat.
I hadn't been there 5 minutes and another car pulls up. OK...I watch them and they go sit at a table maybe 100ft away. No big deal. In the next 5 minutes 3 more families show up, one sits at the next table about 30ft away and the others are between me and the car. I'm now a bit nervous about this. Not too concerned, but, well, you know. All that changed about 10 minutes later. I'm content to sit and wait for everybody to leave. But my body has decided otherwise. Between the big drink and the fired up adrenaline, I am starting to 'feel the need' if you will. Five minutes later and feel the need is now I gotta get to the outhouse in the middle of the park or I'm going to make a mess. So I grab my trash, my book and my drink and head for the outhouse (holding my book over my mouth as I walk by the family between it and my table to attempt to cover my 'stash').
Relieved, I figure my best plan is to just go. So I head for the parking lot, still hiding my mouth, and reach the car. Like a dolt, I hadn't gotten my keys out before I headed to the car. So I had to put down my drink (on the roof), set my book down, and opened my purse to get my keys. In doing so, I had turned away from the park so no one could see my face. What happens? Another car pulls into the park. AND, goes to pull into the parking space right next to me. So what do I do? Drop the keys.
So now I have to squat down to get the keys, the people in the car can obviously see my face and know that the attire and the face don't match. I stand back up and I'm fumbling with the keys to open the door and then it happens. That uncontrolled event you never want. I got in, started the car and sped out of the parking lot stopping about 2 miles down the road at a turnout. And cried. After that was out of my system, I cleaned up and fixed my makeup but my skirt, panties and hose were a mess, I get out of the car and in the trunk I always have a 'spare' outfit. No means masculine, it was a apricot and white floral sundress. I grabbed it, got back in the car and changed, then drove home. What did everybody see? I don't know and didn't really care.
But THAT is my worst day ever

Jenn

Honestly never had a bad experience dressed in front of a GG.
Had several good experiences though:
"That looks better on you than it does on me" when trying on a girlfriend's dress.
Being bought some sexy, silky underwear by the same girlfriend.

I've never had a bad experience as most all of my crossdressing has been in private.

My best experience was a few weeks ago in Aberdeen. It was my first big day out after months of walking practice and doing short trips in public. My plan was to walk about a mile or so through shopping malls and streets and I was incredibly nervous, but it went really well with no stares or glances as far as I could make out. I tried some lovely heels on in a few shops and after an hour or so, headed back to the car park. Walking past shop windows, I could see my reflection and I hardly recognised myself, I glided along totally satisfied with my look.

As I entered the final mall, there was a beggar sat down on the pavement looking as sad as could be. Without even thinking, I took a ?1 coin from my pocket and handed it to him, my false nails gently touching his hand as I let the coin drop. He looked me in the eye and said "Thanks darling." I walked off with a lump in my throat, I had passed.

No bad experience for me, as I am still in the closet.
When I went to the Ren Fair back in April and May, I had many women see me dressed up as a Fair Maiden. No judgment, no strange looks, just acceptance. I'm pretty sure they knew I was a guy too.
My best experience was when I walked into the corset shop and announced that I wanted a lady's corset to give me a girlish figure. The lady who helped me out was just so super friendly and nice. I told her about my crossdressing and we talked for quite a bit as she strapped on my brand new corset. When I looked in the mirror and saw that I had curves, I told her that she had made a dream come true for me, since I had always wanted to have a girlish figure and she helped make that happen. We talked for quite awhile, and she took alot of time to talk to me. I cannot wait to go again this April.

I've only been seen dressed twice by a friend, and the first time was the best. She went through how she does makeup with me, and we got glammed together.

It was also the worst though, because of how I felt to be dressing and going out, which was a major risk.

Best, a few Halloween parties.

Worst, drove into Boston on a summer evening. Wearing a sun dress, poorly applied makeup, and a wig that wasn’t very good. The first two women who saw me burst out laughing. Retreated and drove home.