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

Started dressing at 12 yrs old. Well i say dressing but wearing sisters underwear was about the extent. It wasnt till i was 15 i experienced my first dress up and that was it, hook line and sinker!!

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!

It all started for me when i met my wife 17 years ago , when she first moved in with me , she would do her best to try and put make up on me which i didnt want. But after 5 years later we was jokin and messin about my moobs sayin that 1 of her bras would fit me , so i went to find them and try them on , i found a bra that fitted nicely it was a 42 DD. The wife came up to see on how i was getting on and saw how i looked , i even found a pair of her panties to put on over my boxers , my wife then pulled me on to the bed and snogged my face off after that i took them off and didnt bother after that. It was only until 4 years ago back in 2020 when we had the lock downs as me my wife had a walk down a road at the back of my house when i was tryin to sort out my balls from sticking to my legs when she says what are you doing me beain me says im just sorting out your panties that iv got on. With a very shocked face and a sweet smile she asked if i had but i didnt. That put the idear into my head so when we got back i went to the bedroom put on her sexy panties and went to show her. She loved it and we made out. Its was at this point i started to think about crossdressing , i chatted to my wife and she was ok with it. When i started to dress up and put on the make up and wig to seen the new me thats when i started to feel diffarnt and right. Now i can only dress up when i can as family life gets in the way , i feel very strongly about be female and i still need that curage to see the docs to be refurred to gender clinic and to be put on HRT.

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

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