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MadelineWilco

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

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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

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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!!  

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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. 

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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

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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.

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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. 

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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

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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

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Kellysinclair101

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. 

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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

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RhondaS

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. 

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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. 

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Ms Maddie

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.

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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 ).

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