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I was about 20 when I started and wore a pair of my gf’s panties, then I was left alone in a friends house and saw his mums satin panties and felt the need to try them on and it took off from there

It all started while house sitting for the neighbors while in the bathroom I noticed a pair of nylon panties! Not really sure why I felt compelled to try them on but I did and I couldn't believe how amazing they felt and I knew that I was gonna be wearing these for the rest of my life and then I got an erection and I had to find more. I went into my friends mother's room and I was overwhelmed with all the nylon lingerie I tried on soft cup bra's, camisoles, full and half slips stockings and garter belts (it took a long time trying to figure out how to connect them lol) it was incredible and I knew it was wrong, I took a few of each except for panties I took several pairs. I hid everything under my mattress and I would put on my newly acquired lingerie and I thought it was really wrong to enjoy wearing these things but it felt I honestly belonged in these I tried to ask mom and neighbors why did some actor's wear women's clothing.? They're doing it for laughs and I said do people who aren't actor's wear women's clothing? And they said yes but they are crazy, weird, sick in the head, child molesters and should be in jail to get help. Remember this was late 60,"s early 70's and crossdressing was not tolerated so I didn't have anyone to talk to and as I started dating again I would see if it would be accepted and I never found anyone so I stayed hidden until I was 56 years old and been through 2 marriages and several live-in"s I decided that I will not hide anymore!!!!! And then I met a woman I knew SHE was THE ONE I was scared to reveal my secret but if we're gonna be together she deserves the truth and I told her everything and I would give her however long she needed to think about it. About 4 days later she called me and I was praying that honesty is the only way to have a fresh start and she said that she investigated and she accepts my ccrosddressing lifestyle and we'll try it and we're getting ready to celebrate our 7th anniversary and I have never been happier there's a few other incidents that I will share later

instantes at 14 years old trying mons lingerie. I just happened.

Kate's Hideout...

It all started accidentially with Kate.
Kate loved to play only dolls in her childhood to big surprise, wonder and upset for all around... No other toys attracted her. Carresing dolls and puting them to sleep around was the first sign that Kate was misinterpreted by doctors and was getting wrong education and upbringing...

At the age of 13 she started look into her Mother fashion magasins to discover a serious conflict between two fashion parties: Midi in her time and bright era of mini that suddenly died before...Kate got interest in fashion.
She could not undrstand why, why the ladies around just abandoned mini...that caused so much arrose in Kate...

So she started drawing and scetching skirts she would love to wear... She still remembers those styles she was inventing many many years ago that came to life quite recently only and always brought her smile of her child dreams...

So one day she got interested was her Mother a member of Midi or Mini party? It was a serious test...
Surprise was Mam belonged to both...
But her ellegant wedding dress still at the wardrobe was stuning truth of Victorious Mini underground...

Kate could not resist the beauty of shiny dress with hundreds little buttons one to one from very short bottom to the very english top of that magic dress...

So Kate tried it, and then the tights, and then the hills and even lipstick...

Until one day she was caught and found to be Kate in her doll playing Soul...
To much stress and pain for her parents who tried all necessary cures...

Kate became a sleeping beauty for decades... Dreaming of the passionate Love with another Princess. Love in dresses that will suddenly reveal Kates extraidinary clitoris elongatus as doctor finally diagnosed it...A revelation to be for a happiness and pleasure of her Loving Princess...

After decades of searches and tries... Kate decided just live peacefully for her own pleasure and bought beatiful tights to try again, then after a pair of beautiful boots and two beautiful skirts.. One Mini and one Midi...
To her surprise she enjoyed both... to travel in the trains...

She still does not understand why but she became a member of both Mini and Midi parties too as her Mother...

I started dressing from the age of 12 i used sneak into sisters room and wear her dresses
Would love to meet up with other crossdressers for gurly fun time

Didn't crossdress until my late teens/early twenties. And then only once, tried it for a sexual experience.
From what I can remember, whilst being extremely erotic, making love to a woman whilst dressed as a woman, but it was also strangely comfortable. Didn't think that much about it, and buried it, denied just how I felt whilst I was dressed that way. In part that was down to my own insecurities, and generational stigma/views surrounding transvestism (as it was known back in the day).
I have body dismorphia about my ankles (as a male they're way to thin), and quite recently over a scar from a biopsy I had on a cancerous growth just outside of my lung, where they had to put a drain in my chest to catch any blood that may have been leaking. (Cancer is currently in remission after receiving radiotherapy last year).
Fast forward 30yrs, a misinterpreted comment from my gf (her exact words were "I could **** your arse right now") now me being a dirty minded fucker, immediately thought about being pegged by the woman I love, being used in that way by her, it was an immediate turn on.
It quickly became an obsession, I fantasised about it constantly. Even going as far as buying a strap on and a strapless dildo for her to use on me. At first she thought I was bisexual or even homosexual, took me a while to explain to her that,whilst I was almost desperate for her to peg me, in no way shape or form do I find the male body to be sexually attractive, and that I was only sexually interested in women (especially her).
Only to find that she wasn't comfortable doing it.
So I became frustrated, and as frustrated men do, I turned to porn, to **** myself off watching women **** their man in the arse. Whilst scrolling through a porn site, one day I came across (literally as well as figuratively), a video, and there was this male dressed as a woman, wearing a short black skirt, a blouse, and suspenders bent over a table whilst a woman was fucking him with a strap on. He didn't look uncomfortable or ashamed by the way he was dressed (or by the fact that he was getting fucked). My mind made connections that I thought were long forgotten, stirred up strong feelings and emotions that I couldn't explain, why was I feeling this way?
The more I thought about it, the more confused I felt. A week or so went by, and I tried talking to my gf about how I was feeling, and that I wanted to try being feminised. However she refused to listen or even talk about it. So I brutally ripped the proverbial plaster off, one morning after a Nightshift. I bought some lace panties, and a pair of suspenders, and wore them as well as a lace teddie negligè, belonging to my gf, under my PJs, and after I had a couple of JD's and coke, we went to bed, and I laid next to her.
OMG, it was the single most erotic experience of my life, my whole body was tingling, and felt like it was on fire, we started to kiss and caress each other, until she felt what I was wearing through my PJs, although she didn't know what it was. She jumped out of bed, in shock, and asked me what I was wearing. So I showed her, the look of disgust on her face hurt so bad. I was expecting to feel guilty and ashamed. But I didn't feel that way at all, I felt complete, like I had found a missing part of me, that I didn't even know was missing. I felt so comfortable and relaxed, so unashamed. And so fucking horny, (I won't tell me how many times I wanked off that day), she left the room, but I didn't take them off as I felt so comfortable, so confident in myself. Next thing I know I'm trying some of her clothes on (we're more or less the same size), it just felt right, and familiar.
Sadly my gf and I are no longer a couple, although she is very supportive of my female persona (Dion). She just can't/doesn't want to see me in heels, skirts & dresses.

Started aged 12, whenever I was home alone I’d sneak and wear my older sisters clothes

At the age of ten I first tried, then next time around 28 but came out about it 3 years ago

Michelle from Glasgow. My girlfriend got me started 3 years ago. Have only ever dressed with her. Now id love to dress with someone else.

My first CD experience was at 15 years of age (mums panties) felt amazing but was a one off recently been watching CD and trans porn which has awoken the feeling , my first real CD was a week or so ago and was so good , I have now decided to explore this side of me and have starting enjoying purchasing some sexy bits

started wering my moms Pantyhose,girdles and heels at age 5. and grandmothers whenever id visit. From age 7 to 15 my Aunt Jean would dress me totally enfemme the entire time id visit her. I LOVED that!

I remember I was 8 or 9, and I got a closed friend. He invited me to his room to check out some adult books. We can't help to play oral at last. Then on the other day, he invited me to spend a night with him(her), he borrowed some tights and lingeries and dresses from his sister. At beginning, I love to touch her legs in tights, in the 2nd round he asked me to put on these stocking and boots even the vest, I knew I would never stop wearing pantyhose from that monent on.

I had my first bi encounter during my first ever sleep over when i was in 1st grade, it was my best friend. Well soon after we continued our playing and when i was 11 i one day saw a pair of his lil sisters oanties in bathroom. I tried them on and from that moment on inwas hooked. Even today am sooo haopy that i thought about wearing those cute lil white with pink trim panties. love how my lacy thongs feel!!!!

For me, it was a sort of challenge... i'd been out with my girlfriend to see a band at the local tech college and she was moaning that she had guys groping her - i said so did i! I've always been quite "petite" and in the 70s i had hair down to my waist, wore tight jeans and floaty shirts so... she said "you should see what it's like in a skirt!" and i muttered "yeah, right..."
Next time i arrived to take her out to see some bands, she had her older sister's clothes laid out waiting for me! After she'd helped me dress, done my makeup she let me look in the mirror and WOW, this is how i'm meant to be!
We went out (i was bricking it...) and i loved the different attitude i got from everyone, it was like i was the girl i'd wanted to be when i was at school, but grown up, i'd known since starting secondary that i wasn't "one of the lads".
We had a brilliant time, and yes, i did get groped more in a short denim skirt than i had in jeans! Anna and i ended up sat on a guy's knees in the bar between bands, and i ended up driving him home (he was trollied!) and we got invited in...

I started wearing silky half slips when I was 8 years old, my mum and grans slips. It was such an amazing feeling with the silk and lace. I was hooked on them.

How I started to dress my sisters used to dress me up and put make up on when I was 7ish i loved it but they used to lock me outside when they did it. Then I did it for a while around 13-15 and stopped. I thought I never would dress again untill I was 22 my gf asked could she do make up on me and ever since that it opened the door back up and still to this day at age of 25 still going strong and couldn’t ask for any more support from my gf she encouraged me a lot and when I dress I feel amazing it’s like weight gone off my shoulders. My next goal is to feel confident going in public!

Found a bag in a field once when i was walking home from school, i opened it and inside was brand new lingerie, garter belt, stockings, panties and bras, i took it home, snuck it into my room and began to put in on, it was so erotic, i began sleeping in the lingerie, been wearing panties and lingerie ever since.

Following on from my previous post I suppose the spark was there from when I was young. I remember taking a fancy to my mum’s orange cardigan then later having to wear girl’s pyjamas a few times as money was tight. One winter’s day I was dressed in girls tights as it was really cold that day having come out of hospital after an operation on my feet. That led onto nighties and the rest,as they say,is history