What's your favorite crossdressing experience you've had?

[MadelineWilco]

Hi all,

When I dress up, I "become" a girl. I go by she/her pronouns, and my name is Madeline. What's your favorite crossdressing experience you've had? Mine was my second time. The first time dressing up was just "meh," but the second time was amazing and just felt sooo good. I put on my brunette wig and full face of makeup, I put on my lacy bra, then, as I slipped on my lacy cheeky panties, my voice all the sudden became flowing, breathy, and extremely feminine, and I cutely and very girly said "Oh, yes, This feels so amazing, ohhh!!" I started finishing up my dress up with my mini dress, fingernail and toenail polish, high heeled sandals, and pantyhose, I looked at myself in the mirror and was amazed at how sexy I looked. I was gorgeous! I said very girly "what a very sexy girl you are, Madeline," and I giggled in an extremely girly way! Last time was not so great, but this time was so pleasing and I was so sexy! I enjoy it very much when I do it, but nothing will ever beat my second time as Madeline, EVER. Share some of your awesome crossdressing stories!

Thanks,

Madeline

[VickySGV]

For me it was nearly 20 years ago when I treated myself to a full makeover at a CD boutique.  I had bought some clothing there two months before I scheduled the beauty appointment.  White blouse and skirt, a wig that was a dark auburn and medium long.  Full face make up, they fixed the wig for me (bangs too long) and then an hour of chatting with other "girls" who had showed up for a weekly dinner party which I was invited to,  Very good dinner of Chicken Marsala in a restaurant decorated with pictures of famous Drag Queens and Gay actors.  Then over to a Trans night club at a famous drag show venue.  Ten years later I realized I was not CD and had to go the full route of transition.  I still have the blouse and skirt, but the one sad thing of the evening was my shoes did not fit and tore my feet up.  It was a present to me on my 49th Birthday.  I am just a bit older than you!!  

[MadelineWilco]

2 hours ago, VickySGV said:

For me it was nearly 20 years ago when I treated myself to a full makeover at a CD boutique.  I had bought some clothing there two months before I scheduled the beauty appointment.  White blouse and skirt, a wig that was a dark auburn and medium long.  Full face make up, they fixed the wig for me (bangs too long) and then an hour of chatting with other "girls" who had showed up for a weekly dinner party which I was invited to,  Very good dinner of Chicken Marsala in a restaurant decorated with pictures of famous Drag Queens and Gay actors.  Then over to a Trans night club at a famous drag show venue.  Ten years later I realized I was not CD and had to go the full route of transition.  I still have the blouse and skirt, but the one sad thing of the evening was my shoes did not fit and tore my feet up.  It was a present to me on my 49th Birthday.  I am just a bit older than you!!  

That sounds so awesome! I know it was a great experience. I'm sorry your shoes hurt your feet, they can be hard to fit. I have relatively dainty, narrow, feminine feet, so a lot of feminine high heels I can wear. 

[MadelineWilco]

Being a girl has to be one of the best things that has ever happened to me. I always thought I was going to be this tough, masculine guy, but nope, I'm a really feminine, cute girl! Even though I'm AMAB and haven't had any surgery or hormones, I'm already a girl in my views.

Madeline

[VickySGV]

2 hours ago, MadelineWilco said:

I'm AMAB and haven't had any surgery or hormones, I'm already a girl in my views.

 

That is all it takes, on this Forum we let you be who you are as you are.

[MadelineWilco]

12 hours ago, VickySGV said:

 

That is all it takes, on this Forum we let you be who you are as you are.

Thank you, Vicky. I greatly appreciate it. I love being a girl. 

[Sally Stone]

I'd have to say my favorite experience was the first time I went out in public.  It was so many years ago.  I was a new member of the TRI-ESS group in Atlanta, GA and our monthly gatherings were weekend long events held at at 5 star hotel.  The hotel was a conference center, so every weekend there were conventions and big weddings.  Expressing myself as a woman in a social setting like that was initially terrifying but amazingly exhilarating.  Those weekend meetings really helped learn to strut my stuff.

 

Hugs,

 

Sally

[MadelineWilco]

9 hours ago, Sally Stone said:

I'd have to say my favorite experience was the first time I went out in public.  It was so many years ago.  I was a new member of the TRI-ESS group in Atlanta, GA and our monthly gatherings were weekend long events held at at 5 star hotel.  The hotel was a conference center, so every weekend there were conventions and big weddings.  Expressing myself as a woman in a social setting like that was initially terrifying but amazingly exhilarating.  Those weekend meetings really helped learn to strut my stuff.

 

Hugs,

 

Sally

That sounds great, Sally! I may go out in public soon if I put on a REALLY gorgeous and very sexy image like I did my second time as Madeline. That time was exhilarating and so pleasurable. 
Hugs,

Madeline

[Guest]

I haven't  went I to public yet . But for my hole life  I felt like I always crossdress as a man . Never felt  like me . I am just me and I'm a woman at heart and sole . The rest is irrelevant. 

[MadelineWilco]

19 hours ago, Kellysinclair101 said:

I haven't  went I to public yet . But for my hole life  I felt like I always crossdress as a man . Never felt  like me . I am just me and I'm a woman at heart and sole . The rest is irrelevant. 

I am an AMAB demigirl myself. I haven’t had surgery nor gone out in public as a girl, but I feel like a girl, I dress like a girl, I call myself a girl’s name, so I already am a girl.

Love,

Madeline

[MirandaB]

I did two makeover sessions in London last summer after decades of delaying.  The second at Boys Will Be Girls has set such a high bar for crossdressing memories it may never be topped. 

[Katelyn]

I had this friend about two years ago, very amazing girl with a really open mind, and she worked part time at this costume shop. So after having come clean with them and her boyfriend, her parents and the tenant in their back yard flat who is also her band member, they all started calling me Lynn (her sister's name is Caitlyn, and they call her Kate so I got Lynn) and referring to me by girl pronouns, which by itself was rather amazing. So one weekend she invites me over early the morning, asks me if I'd like to get out of the house to dress up a little and I assume it's at their house so I shave nice and clean and then head over. I got there and Kate is there, and I learn that she's actually a makeup artist and has unpacked all her stuff in preparation for me specifically. So she asks about my favourite colours and spends almost an hour on making me look spectacular and refusing that I look in the mirror until she's done, which already blew my mind when I saw it. I thought that was the ultimate. 

Then my friend brought up all the outfits and costumes and fantasies I've discussed with her again while gathering her stuff as if they wanted to go out, and then drags me to the car, which made me nervous beyond measure. 

She had arranged to do some spring cleaning after hours at the shop on that weekend so she could have the keys and we could all go try in different thins and take photos in costumes. 

We spent majority of the day there. 

That is my all time favourite memory. I also went to one of her shows as myself after that at a little bar, they had a ladies night special which I was granted to partake in. And I didn't get trouble, looks or lip when using the rest room which was a close second. 

Life can be real good sometimes. 

I miss my friend. 

[Maddee]

Good memories of a woman I lived with when I was 20-22.  I crossdressed with her from day one.  Everything was new to me, and she was the first other person I really trusted with this.

She showed me how to put on stockings, bras, makeup, etc. She was wise and shared with me knowledge of about sex, trans, escorting, porn,  and LIFE....only some of which I could handle.  We shopped and walked about and wore alot of short skirts.  We got in some trouble together, usually her fault

We were both size 4 and shared our clothes.  And envied each other's attributes at times.

Sounds like heaven, but it wasn't. 

But still a treasured memory.

[Dinaki]

I went from male school uniform,  directly to a plisse skirt. Back in my days it was also illegal to be a transvestite ( crossdresser ).

[denise58]

I live in New Zealand and we have charity shops , they are nearly always staffed by kindly older women , most are aware that you are shopping for ladieswear and are generally pleasant, I think it makes their day more interesting if they get crossdressers shopping  ,I have bought some gorgeous items over the years . I have a passion for vintage nylons , girdles ,nylon petticoats , camisoles and double layer vintage nylon nightwear .

I always underdress to excess when shopping at the shops , wearing bra ,granny pantys ,pantyhose,corselette ,camisole and full slip  which can be a bit of a challenge concealing under male clothing , I openly shop for only womens clothes and am obviously a crossdresser , I enjoy the thrill of them knowing im girly , one lady in particular used to put clothes aside for me and then offer them to me as she knew I loved nylon nightgowns, she would also encourage me to buy blouses and skirts also womens shoes and  I could try all these things on in the changing room , I would try on shoes in her presence so that she could see my painted toe nails through my tights , I found it thrilling that she knew , I also wore ladies perfume and one day she said " I have the same perfume that you are wearing ", I would visit the shop twice weekly and loved being there as the shop was decorated in an extremely feminine decor .

 Sadly she stopped working there and the new staff were not as welcoming.

 

[Leesa Metz]

Hi gals!

 

ive had a couple of really great experiences all dolled up.

 

years ago when the family was out of town for the holidays, i shaved especially close, did a painstakingly meticulous time with my makeup, put in a perfect tuck under some raspberry red nylon briefs, hooked a nearly matching bra around my shoulders and filled them with my home made forms before pulling on some pecan shade pantyhose.  i first stepped into a nylon half-slip with 6" of lace and followed that with a gray wool skirt.  i carefully slithered a purple cowl neck sweater on before arranging my chestnut brown tresses and my costume jewelry-dangly earings.  the last of my ensemble was a pair of peep-toe, patent leather heels that were 3" high...

 

i got in the car, went to the local mall and did a little window shopping before the movie i had selected, was scheduled to start.  i popped into the Payless Shoe store and was looking at some strappy sandals for the upcoming New Year Eve (the family would still be gone) and was chatting with the super helpful clerk.  she left to help another customer for a moment and came back to me while i was trying on a pair of bejeweled slip on sandals.  she asked me if i had heard what the other customer had said and i replied that i hadnt.  she went on to say, that the guy (late 30s) had said to her "that lady certainly has a deep voice dont you think?" and the clerk replied to him "maybe so but isnt she just beautiful?"  WOW!  talk about an ego boost!  he had replied "yes she sure is".  i was on cloud 9 the rest of the night!

 

another time was while i was visiting a friend as Leesa, and as we stood facing each other, and she looking me over from my wavy brown locks to the red sparkle polish on my toes, said to me "you look better than most women i know.  your makeup especially your eyes are better than I can do"

 

alas those days were almost 20 years ago.  its a shame that i would scare most people if they were to see me today...

[Jackie C.]

3 hours ago, Leesa Metz said:

alas those days were almost 20 years ago.  its a shame that i would scare most people if they were to see me today...

 

Oh please, you and I are the same age and I hardly ever send small children screaming to their parents. I wish I'd started on my makeup game 40 years ago though. I'm terrible.

 

Hugs!

[Kasumi63]

For many years, I have been going to a Japanese snack bar (a quaint karaoke bar) where I’ve been dressing up for years. I’ve worn Lolita fashion dresses, a sexy kimono dress, and other interesting outfits. Although I was a regular customer, other customers, especially the non-regulars, often mistook me for a hostess and would call me to their tables. Of course, I always played along! Anyway, I think my most popular outfit was my AKB48 (Japanese girl idol group) outfit. (See my photo below.) Whenever I wore this outfit, customers would urge me to sing a AKB48 song, so I learned a couple. That always got people dancing. Unfortunately, I don’t have the outfit anymore. (I wore it so often that it just got too worn out!) By the way, I haven’t been to this great snack for over a year now, because of COVID-19, and I have been transitioning in the meantime, so I think everyone will be quite surprised when they see me again! I can’t wait!  If you’re ever in Okinawa, you absolutely have to come here, so let me know, and I’ll bring you!

[tracy_j]

That's a lovely picture / outfit. I like the Lolita styles although am probably really too old to be wearing any. I am influenced by them though. You probably have not seen this one which I posted here a year or two back. I have not had occasion to wear as it would be too much locally but I had to put the outfit together. Over there, at least in some places, it may be more normal. Lolita dress is rare here, at least in my more rural and small town setting, although I have seen one or two over the years.

 

 

 

Tracy

[Kasumi63]

I like your outfit! That’s cute! Here is one of my Lolita style dresses. Of course, I would never dress like this at work, but it’s fine for the club.

[Kasumi63]

Or this one:

[Ivy]

5 hours ago, Kasumi63 said:

Here is one of my Lolita style dresses.

Nice.   I could never pull that off myself.

[tracy_j]

I just love the patterned white dress Kasumi.

 

Although it is possible to buy dresses like those online I am glad, in a way, that the shops do not sell them locally as it would make me so sad and entice me to buy something I could only wear indoors. On anyone here, cis or otherwise, it would attract lots of attention, probably much of it unwelcome. That is maybe why they don't sell them and are rarely worn. It's strange really as they are not provocative like really short shorts would be but too feminine even for feminine women. Perhaps too 'little girly' for the UK.

 

I do sometimes wear dresses that short though. I have just realised how short the black dress in my photo is. My partner is often mentioning 'bum covers' meaning the short skirts some women wear and is sometimes referring to me. I do wear the dress part (a sleeveless skater dress) over opaque black tights when I go to the shops occasionally, usually with a long sleeved coloured cardigan. It's good to mix and match with outfits so giving a variation with less expense. I wear the shoes in the warmer weather too, but usually ankle boots during the winter when I dress up a bit.

 

Tracy

[Kiera]

 

      I love flouncy, more 60's style "luv child" dresses has anyone here shopped "airydress . com" I cannot believe their flash sale pricing I placed an order just to see if "for real" or not . . they're based out of Hong Kong with warehouses in the US.

[Ivy]

I love “hippie” dresses myself.    I have a friend who had a “hippie boutique” in town for awhile.  She’s given me a few things.   
With warmer weather and (hopefully) less covid, I’m hoping to be able to get out more.