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Like most girls on this site, I wanted to wear panties and pantyhose when I was a young boy, and I have previously posted about getting the opportunity to wear tights in an elementary school play and the time a high school girl friend put makeup on me – but I was not inspired to try to dress completely en femme until my early 20’s. It was seeing female impersonators in a gay bar that really peaked my interest in the whole ensemble – heels, hose, undergarments, a dress, makeup and a wig. Some of them looked so sexy and convincing that I wanted to try! After attending a handful of drag shows, and with the encouragement of a gay co-worker who bragged that he was a regular crossdresser at these shows – I got together with my crossdressing friend and another friend of his and I let the two of them dress me up and take me to the bar – they even talked me into shaving my legs.
How about you other girls – what inspired your first complete feminization?
I got dressed and made up en femme a number of times in secret but my first outing en femme was actually encouraged by my wife after I mentioned I was interested in attending a makeover weekend.
At the time she was still struggling with the fact that I was a crossdresser and had been since I first told her 15 months earlier. In that time she’d been willing to discuss whatever I wanted to discuss and even talk to me about things she was interested in or curious about. She was also okay with me crossdressing at home though with discretion as she was not yet ready to see me that way.
When I mentioned the makeover weekend she said “You should do it” so with her blessing I had a wonderful weekend and made my first venture ‘beyond the gate’ and out into public. I was amazed at the results of the makeover considering that to that time my makeup efforts were primitive, to say the least. After I’d been madeup and dressed in a couple of beautiful outfits for photos the couple running the makeover service said “Okay, pick an outfit for us to go out to dinner in.” After a bit of indecision I chose an outfit and we duly got organised. They didn’t pressure me to go for a sit-down dinner but the deal was that if I didn’t want to eat in the restaurant I had to at least go with them to get the takeaway dinner.
I was both excited and fearful but we went to the restaurant to collect the meal we’d ordered. The funny thing is that I went from “Oh heavens, everyone in there will be looking at me; I think I’ll die” before we walked in to “Hmm, no-one even seemed to notice me. How disappointing…” when we left.
My first venture out fully en femme was most memorable, if for no other reason than when I got home my wife asked if I’d had a good weekend. My affirmative answer was followed by “Did you get photos?” When I also confirmed that she said “Okay, show me. I think it’s time I saw this other woman in my life.” Her reaction was amazing and we’ve just gone on from there.
oh wow Jane;
such a fantastic experience. So happy you had a great time.
now tell me –
what was her opinion of the photos?
Damn, the pub crawl idea sounds great. We just shared a bottle of wine while we went through the photos and talked about the weekend. Did I mention, I got a lot of photos…
Kendra,
I first dressed on my own at age 11 but it was seeing the girls in high school and early college that were my siren call to a more full femininity and it was the first year of my marriage that I first tried full on dressing including wig and makeup. Coincidentally the wig packaging was what outed me to my wife who was furious and almost left me that day. She never accepted or even tolerated Cynthia though and thought she stayed then, she did ultimately leave about 12 years later as I could not stop the need to dress even t the cost of my marriage. Not an easy road we travel but I wouldn’t want to have not been who I really am!
Cynthia
I am so sorry that turned out badly in the long run. Unfortunately not everyone can have a supporting spouse, especially after years of hiding that side of you.
I am fully aware that you can’t give up that side – it is part of who you are whether you express it full or just part time.
Hope things are better for you now.
Thanks Rosaliy! I came to peace with the ex(we have wonderful kids together- and are cordial-the crossdressing is just never brought up) and I’m living OK-if alone..I have ome to terms with my need to crossdress and now just need to figure out if there is more needed or if dressing privately is sufficient( i suspect not 🙂 )
Cynthia
As to what inspired me to go out that first time, well I did not have the experiences you all had. As I have said elsewhere, my early dressing in high school was something I just had to do. It was fun dressing and returning at home initially but after a while that wasn’t interesting. So I took to going out for night time walks while dad was at work. It was challenging and scary to be out as a girl. I felt sort of out of place too with a kerchief on my head but I would have felt worse without something disguising my obviously male hair style. Sometimes I would see people across the street, mostly girls out with their friends. Some looked at me funny, probably because of the kerchief that none of them were wearing. I must have looked as out of place to them as I felt. Still, i continued going out for walks when time permitted.
It was just time. I knew it inside and finally did something about it. It took more than 50 years, but I did it.
While I have dressed completely and in private – at least with the exception of a wig – for most of my life, I’ve always known that being Millie is part of being who I am. But it took until a few years ago to realize that I wanted to share Millie with the world.
So, I went to a transformation service, got the whole package, and nervously stepped out into the world. And when I was walking down the hall at the hotel and my skirt started to slip down I was really scared, but just held it in place and moved on. Got a few glances in the elevator, but I survived, and it’s been a fantastic part of my journey. I’m still not completely comfortable in public, but I am definitely a much happier person now that Millie has the opportunity to appear in public and knows that she will not be terribly embarrassed and will survive with her dignity and style intact.
I always felt more comfortable dressing as my enfemme side.My family too,said don’t give up on anything at all and they see I am completely happy now.Been doing this for 5 years now and no regrets since I have been crossdressing at an early age.
I think there were many inspirations that finally lead to that one first time in public. When I was about 8ish I wanted to be a witch for Halloween, my mother accommodated my by cutting down her wedding dress and making me a white witch costume. Growing up I spent time playing Barbie’s with my sister.
Later I think it was the freaks of the entertainment world that started to push on that nerve. Liberace, Ziggy Stardust (David Bowie for those who don’t know), Alice Cooper, Mick Jagger, Elton John, Boy George, Freddie Mercury.
But like Millie it was time. I hit my 60th birthday and decided I’ve waited long enough to live my life and went with a transformation service. The Portland OR TG scene is phenomenal and the most comfortable I’ve been. I went there with nothing, got dressed from underwear to hair and makeup.
The outcome of that made me realize that I would be more comfortable and happier with my own wardrobe and accessories.As my femme friends here know ,I was rather asexual and a computer nerd and also only 19 when I married my wife Shelley who was 26 and formerly married to a Ken type guy . I was atonished after our wedding , that she was trying to , or , we’ll help me find myself , I never consider myself lost ! Anyway , she would buy ladies pants , sweaters , shirts , jackets , and coats for me that we very men’s type . Slowly , I started growing my hair longer , and wearing it in a long guys ponytail . Then she started having me put clear coats on my nails , and I started wearing little natural makeup . We had a long talk because I was starting to be perceived as a girl . Then I decided to see where this would lead , and started wearing lingerie that she bought me and a sports bra . I was a 34A and then I started wearing side zip pants and ear rings instead of just studs and letting my hair be cut in a long pape boy style . The real change came when I started wearing French nails ( and toe nails ) and I started wearing brackets and ladies rings and necklaces . OVS I was know being perceived as a lady .. Then I was plain that my transition was totally femme , and totally started wearing my hair in very feminine hairstyles and wearing pretty makeup . Then I started wearing pencil dresses , skirts , and ballet flats and Mary Janes and taking hormones .
Karyn,
First off I’ve been meaning to tell you-absolutely gorgeous! I know many women who would kill to look as good as you do. SEcondly how fortunate you were to find someone who saw within you the beautiful butterfly that was hidden inside the caterpillar you were previously. Finally I love that you went with your heart and let yourself become the feminine person you were obviously meant to be. Thanks for sharing your stories and I hope that one day more of us will find someone as loving and accepting of us as your wife is of you.
Cynthia
I can’t recall the first time I dressed up but I can transfer what got me into it. I was a young little bit and .. excuse my potty mouth… My mom would always bring men and women over very late at night, we wold share a room so I would pretend I was asleep, when she brought her friends over and well we only had one BIG BED so I got to hear everything and see everything every single time 😍 , I would get crazy erections and wouldn’t know what to do. I just remember seeing my mom getting dressed with special clothes(lingerie) and start acting really dirty. And I would watch everything and the idea of wanting to be like my mom started to flourish. I wanted to feel like her I wanted to feel as beautiful as sexy as her, and one night she brought a guy over.. but he was different he wasn’t trying my mom rough line the rest of the guys that’d shed bring she was reading him like a little girl and he was liking it. She took out her toys and started penetrating him.. I don’t know what to THINK I es really young really horny he wrote her underwear and acted line a woman…every since I’ve had that FANTASY and I’ve always dressed with women clothes
After my divorce i started to explore more deeply my feminine side and now have a supporative Girlfriend I love feeling feminine taking a nice hot bath and smelling wonderful and love wearing my dresses and shoes and just the ability to look and be ginger I dont have any support in my small town except for my girlfirend who will soon be my wife i always loved womens clothes and shopping felt jelous when clothes shopping with my wife and before that the ladies i would date now i love picking clothes and makeup out for myself and just being my alter ego ginger i am looking for support and friends to help walk me through
Here’s my story, it’s fairly typical. I was about 4 or 5, had the urge for whatever reason and just started. It wasn’t until I was about 7 or 8, that I knew that being a CD was socially unacceptable (1982-83) in the eyes of my family, but I pressed ahead because hose made me happy. Over time I experimented with a variety of different clothing articles. As the years progressed I became more adapt at hiding it. Had a boyfriend when I was 19, he was the first to know my little secret, he wasn’t supportive and so I played it straight until one night my wife dropped a massive bomb, so I revealed JoAnne. It almost led to a divorce, but acceptance came slowly,and now I’ve found peace in my life.
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