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First time crossdressing

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By *adison 71 OP   TV/TS
19 weeks ago

torrevija in Spain costa blanca

I first started crossdressing when I was 13 used to use my mum and sister underwear then as got older got my own many times I felt guilty and tried to stop but then start again I think it's part of me anyone else had same think and would like to talk text me from Tanya x

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By *ichelle999TV/TS
8 weeks ago

colchester

I was 12 started with my sisters party dresses and frilly knickers then onto my mums clothes and first time in stockings I also felt guilty but it was an obsession which has led to a lonely life keeping g it a secret xx

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By *rytonTV/TS
8 weeks ago

Chatham

Not sure when I started but stop for a long while. Finally joined this site to actually try dressing and touching my first cock.

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By *aucey04TV/TS
8 weeks ago

Bletchingley

My journey started in a very similar way.

As a young adolescent teenager I used to try on and enjoy wearing my mums panties and stockings.

Fast Forward too many 'lost' years

I had retained my interest in lingerie and when I retired at long last I had the opportunity to rekindle that long suppressed desire to wear lingerie.

I started to regularly 'dress', just panties at first, but very soon added stockings, suspenders and a bra and began to thoroughly enjoy my fem side.

That enjoyment that was hugely reinforced when I had my first meet wearing lingerie under trousers and a shirt.

My 'pleasure' was further enhanced when I took my first cock, a pleasure which I continue to pursue as often as possible either outdoors or when I can accommodate.

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By *adame BootsTV/TS
8 weeks ago

Tetbury

Not until I had a place of my own about 25.

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By *ady CharlotteTV/TS
8 weeks ago

staffordshire

I was 11 going on 12 when i started, mum had some lovely lingerie, i used to dress in her things at home, and then eventually used to sneak stuff out and dress in the local woods, her shoes fitted perfectly too.

not stopped since, although i dress less of late due to work and lifes general shit"!

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By *fcdTV/TS
8 weeks ago

Southend


"I was 12 started with my sisters party dresses and frilly knickers then onto my mums clothes and first time in stockings I also felt guilty but it was an obsession which has led to a lonely life keeping g it a secret xx"
I was the same, with the addd bonus of a wife that knew but hated it and often used outing me as a threat. A few years ago I started having some therapy for various issues and one thing that was covered was my fear of anyone finding out. The therapist suggested just telling people and taking away the (thank fully now ex) wife's power. She thought I'd be surprised how much the world had moved forward.

Much to my surprise and happiness, all my friends both male and female were fine with it. One female friend cried her eyes out at the thought of all my years of shame. My male friends were all "and?" or in some cases jokes like "It can only be better than your male dress sense". Obviously you know your friends better than me but I can tell you, the relief of being able to be openly me with all my friends is so liberating. I don't dress around them but they've only ever been supportive with one admitting to the same.

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By *ortheastFarmerMan
8 weeks ago

Newcastle

Started at 17 with a dare. Was basically a Halloween party, I went as my female friend, wore her clothes etc, she went as me.

From there got my own stuff, hid it well and just continued. Nothing fancy or over complicated, just enjoyed it.

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By *erlin55Man
8 weeks ago

Pembrokeshire


"I was 12 started with my sisters party dresses and frilly knickers then onto my mums clothes and first time in stockings I also felt guilty but it was an obsession which has led to a lonely life keeping g it a secret xxI was the same, with the addd bonus of a wife that knew but hated it and often used outing me as a threat. A few years ago I started having some therapy for various issues and one thing that was covered was my fear of anyone finding out. The therapist suggested just telling people and taking away the (thank fully now ex) wife's power. She thought I'd be surprised how much the world had moved forward.

Much to my surprise and happiness, all my friends both male and female were fine with it. One female friend cried her eyes out at the thought of all my years of shame. My male friends were all "and?" or in some cases jokes like "It can only be better than your male dress sense". Obviously you know your friends better than me but I can tell you, the relief of being able to be openly me with all my friends is so liberating. I don't dress around them but they've only ever been supportive with one admitting to the same."

Good for you and your photos look great

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By (user no longer on site)
8 weeks ago

How old was ur sister id love wear stuff like thar

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By *ummerTV/TS
8 weeks ago

I am in Spain, not

I do not consider myself to be a crossdresser, I wear clothing and present as myself, not a steroetype.

The fact this site requires us to select from a limited choice compels me to identify as a CD/TV.

I was between 6 and 8 when I stole a pair of pretty knickers from a neighbours daughter.

Obviously I was pre pubesce@nt so nothing sexual, I just liked them, I also stole a pretty lightweight material skirt next as I liked how it moved, plus some pretty socks and a flowery top.

I loved going deep into the woods wearing them running about with the skirt wafting and lifting, I liked feeling pretty.

The neighbour's mother figured out stuff was missing so told my mum, who found them in my room. I was told off and banned from the neighbours, nothing was ever said again.

_______________________________________________________

Once I began buying my own clothes I would have to shop in the youths section, due to being so small, plain pastel colours were okay but most of it was juvenile macho designs.

One day I was trying to find white cotton trousers in Benetton to wear on holiday, they were all mens and too big for my 26" waist, even with a belt the seat, crotch and thighs were too baggy, the assistant suggested I try on a pair in a female size 6, they fitted perfectly.

After I figured out female sizes fitted me it opened up a new world of opportunities, I could buy the prettier clothes I preferred, it was liberating.

I liked the lacey lingerie on display, but it isn't designed for male anatomy, so I chose cotton briefs in pastel colours with pretty designs, I already bought white socks, now I could buy lighter coloured and flowery patterned socks.

I never bought skirts or dresses as I knew I that would draw too much attention and I would be seen as dressing like a woman, I didn't feel like a woman or want to copy what a woman looks like, I just liked pretty things, I liked the style of girls of my age in casual clothing but I didn't feel or want to be a female.

I wear size 6 shoes so it wasn't a problem getting footwear, heels didn't appeal but colours other than black or brown did, gold buckles and other design elements that made them prettier attracted me.

Long hair was the fashion, makeup wasn't of interest, I was baby faced with naturally long eyelashes so I guess I looked either androgynous or a feminine guy

I did get called names occasionally so chose my outfits to suit the environment I would be in, a lightweight nylon rain jacket was my invisibility cloak.

Nobody really has an opportunity for self expression in the work environment, what I wore was just a uniform to me, other than less masculine footwear that was acceptable to their requirements, I blended in, it made my choice of clothing away from work more liberating.

I wore a fine gold necklace that always got remarks that it was a woman's, I would just say it was an 18th birthday present from my parents, purposely omitting to say that I chose it. I wore more feminine jewelry after I came out, I always liked painted nails but only began painting my nails much more recently. I prefer lighter scents and perfumes to the heavier mens.

__________________________________________________________

Stockings and suspenders look as sexy on a masculine guy to me as they do a woman, they frame the thighs, buttocks and groin. I wear them as they are sexually exciting to the viewer, not because I associate them with a female.

Many guys like a smooth, twink physiqued bottom but are put off effeminacy, and by what they consider female attire, especially underwear.

Having to hide that is not being true to myself, I chose a CD/TV profile so they know up front I am effeminate.

Unfortunately there is a limited number of guys interested in someone who isn't 'convincing' in their eyes, so once again I find others wanting me to comply with their expectations rather than just be me.

I am left with a choice of to either comply or limit my choice of sexual partners, so I have outfits for their sake, not mine.

_______________________________________________________________

It all stems from the binary gender narrative, hence why I am passionate about defending the right to identify how you wish.

I am not Trans in the way it is seen in society.

I am male by sex but I do not fit their narrow gender perspective of a man because of how I dress and present myself, nor do I meet their gender criteria of a woman because of my sex.

But they want me to fit one or the other.

Identifying as gender neutral and daring to be part of the extended acronym is even offensive to some, as evidenced in this forum.

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By *ebecca2000TV/TS
8 weeks ago

highlands

I started at 13. Used dress as sister. Had long hair so used tie it back. Her stuff was so nice. I felt so girly. I used go out as her.. That was the beginning for my adventures with men xx

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By *fcdTV/TS
8 weeks ago

Southend


"

Good for you and your photos look great "

Thanks

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By *DAnnetteTV/TS
8 weeks ago

Daventry

I was 21/22 when I first slipped into some panties. As a teenager I was fascinated by my mum's Grattan and Freman's catalogues with all those pages of lovely lingerie, but apart from wanking to them I never raided my mum's knickers drawer. Then in my early twenties I bought a few stocking fillers for my gf Bev one Xmas, including two pairs of satin knickers. She never got them as I slipped on a pair and got a raging hard on and so my story began.

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By *S25biMan
8 weeks ago

Hartlepool

[Removed by poster at 29/10/25 15:29:18]

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By *S25biMan
8 weeks ago

Hartlepool

Was playing strip poker and one of the forfeits was to dress in my friend's sisters undies. Ended up giving him a blow job.

Started my interest in girlie undies but for me was a way of being submissive and humiliated. Would be different if I was convincing but am never going to look feminine.

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By *q oralistMan
8 weeks ago

Torquay

First time I was in a hotel bedroom in London, wife had laid some sexy nylon on the bed and she went in the shower. I was changing and out of impulse picked them up and held them in front of me looking in the mirror, that led to slipping my legs into then - immediate hard on. I kept them on and we went to the see a play that evening, all through it I kept getting hard.

Soon progressed to bras, suspenders and stockings,nighties etc been hooked ever since, could get hard just walking through a lingerie dept. Many years later before I met up with another guy with similar tastes we were feeling each other up and it led to me sucking cock for the first time.

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By (user no longer on site)
8 weeks ago

I was young

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By *laire cd 123TV/TS
8 weeks ago

Welwyn

I was probably 13/14 first started with my mums best friend some of her outfits were so sexy but extremely classy and that look 👀 has always stuck with me 👠💋

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By *axNorthMan
8 weeks ago

Sutton

Only recently started trying it and I’m loving it so far, can’t wait to get some more slutty bits

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By *jh59Man
8 weeks ago

Hinckley

Early teens putting my mother's stuff

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By *ose_QuartzTV/TS
8 weeks ago

Berkshire

Teens like most, I bought my own stuff usually from littlewoods , M&S etc. Once I started my apprenticeship I progressed to buying outfits in Brewer street & Old Compton Street. I used to get costumes from a shop down the Cambridge Heath Road I think it used to be called East of Eden. Also every November I’d go to Erotica exhibition at Olympia which was out of this world for fetish stuff with lots of Trannies strutting around lol I also just started going to the Philbeach Hotel in Earl’s Court in my very early twenties and in typical fashion it closed it doors lol ….anyway here I am now 😂

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By *ldmanMan
8 weeks ago

Rawcliffe Bridge.

Mine was given to me.

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By *erlin55Man
8 weeks ago

Pembrokeshire


"Only recently started trying it and I’m loving it so far, can’t wait to get some more slutty bits "

Looks really good on you I must say 🥵

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By *sobel19791979TV/TS
8 weeks ago

Close by

I was in my teens sisters underwear and from there I have dressed on an off with a few memorable encounters

Back again last month and feel d*unk with the pressure it gives me x

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By *amesmbi47Man
8 weeks ago

Norwich

I started when I was about 45....

Had a shower one morning and there was clean washing on the bed which included one if my wife's gstrings.... Without thinking i just put it on and got an instant erection...

I then slowly progressed from being a straight guy to one who prefers guys and trannys....

I do often wonder though that if the washing hadn't been on the bed that morning would I have gone down this path....

Either way, im pleased I did.

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By *dstefiMan
8 weeks ago

Solihull

Not my first time, I'd dabbled before, but the time that convinced me I was a total crossdresser ...

When fairly young in student days I moved into a rented house that had just been vacated by a group of student nurses. It hadn't been left particularly clean or tidy, but in amongst the general mess was a huge cache of worn, discarded underwear. Variously stained and torn knickers, bras with damaged or missing clasps, stockings, tights, the odd suspender belt etc.

Somebody else was due to move in and share but not for a couple of weeks, so for that fortnight I had free rein to live out my every hot fantasy about dressing and spent every waking minute in the grubby lingerie, looking at myself wearing it in the mirror, trying every item on and of course wanking myself stupid into it three or four times a day.

That everything was pre-worn and cast off kind of gave me carte-blanche not to afford it any respect and as there was so much I didn't bother washing any, just kept pumping my permanently erect cock and then-abundant semen into panty gussets, bra cups, stocking and tights feet until every single item was stiff and encrusted in my dried-on spunk.

The day the other tenant moved in and all the evidence of my fevered kinky fortnight of constant masturbation had to go into a black bin bag was a sad one, but I'd changed for good now and knew I'd be now be a lingerie addict for life.

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By *ustPeekinMan
8 weeks ago

Alresford

About 11. First of all it was just cotton knickers. Just looking and feeling. Then trying them on. After a while it come came clothes too. School uniform. I was hooked.

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By *rookeTVTV/TS
8 weeks ago

Linwood

I was handed a carrier bag in a cottage containing a cheap blonde wig a bra, pants , tights and some red heels and asked to put it on the rest is history

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By *araLovesCumTV/TS
8 weeks ago

Gravesend

In my teens. Started with a friend I played with he dared me to wear his mums stuff which I did. We played while I was in it and I loved it. Never looked back. Met a guy at uni who liked me dressed as his gf when we fucked. Afyet that for many years it was just occasional until Covid gave me more time to expand.

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By *axNorthMan
8 weeks ago

Sutton


"Only recently started trying it and I’m loving it so far, can’t wait to get some more slutty bits

Looks really good on you I must say 🥵"

Thank you 😈

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By *illmanimp1972Man
8 weeks ago

pitsea

I must say I've never actually tried although certainly been thinking of it

Any volunteers to help

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By *llie74Man
8 weeks ago

Pyle

Same as most of you started with mums and sisters late 80s and 90s

Mum was a nurse old style dress uniform and had full 80s clothes like fur coats and red heels that fitted when my sister had nicer underwear and bigger shoes so when I grew up I used them. She was a student nurse the white dress with yelllow strips.

When I moved in my wife’s feet were the same and mine so used her clothes in secret.

Only dressed once outside in Greenhouse Newport loved it

Just need more chances to dress

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By *erriTV/TS
8 weeks ago

Hastings St Leonards

What started dressing as a young girl when I was nine years old I enjoyed dressing as a young girl it made me feel nice and I'll still dressed now as a woman and I'm a pre-op trans woman now old female hormones and waiting toward the operation down below I did not dress to be sexy I've just dressed to be myself as I've been more happiest since of been a female and anything else for the last five years I've lived over female 24/7

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By *ylonplesureTV/TS
8 weeks ago

Stone (staffs)

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By *osie888Man
8 weeks ago

Bathgate

exs and steps dots , loved washing day

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By *DAnnetteTV/TS
8 weeks ago

Daventry


"Teens like most, I bought my own stuff usually from littlewoods , M&S etc. Once I started my apprenticeship I progressed to buying outfits in Brewer street & Old Compton Street. I used to get costumes from a shop down the Cambridge Heath Road I think it used to be called East of Eden. Also every November I’d go to Erotica exhibition at Olympia which was out of this world for fetish stuff with lots of Trannies strutting around lol I also just started going to the Philbeach Hotel in Earl’s Court in my very early twenties and in typical fashion it closed it doors lol ….anyway here I am now 😂"

The Philbeach! You have sparked a memory there! Oh wow! I had some great times there back in the day.

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By *inkysub64Man
6 weeks ago

Manchester

Only started dressing wish I had done many years ago. Would love to find a regular friend to share ideas and fun together

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By *ungusMan
6 weeks ago

gidea park

Only just started to wear lingerie for first time love it feels so good

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By *ungusMan
6 weeks ago

gidea park

Like to find someone local to help me

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By *mandaWhenDressedMan
6 weeks ago

around

Every time I try and think of when I started dressing I then remembered something earlier.

We moved houses a lot when I was growing up so remember dates quite well.

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By *suckcocks666Man
6 weeks ago

Birstall

An ex gf got me to wear her rocking and suspenders for a fancy dress party, I've loved it ever since xx

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By *oe trinityMan
6 weeks ago

Leeds

Used to hear mum in the next room after my parents split I could hear everything through a heating vent that connected our two bedrooms I used to wear her tights n lay there wanking myself silly

She used to go to a nightclub called pussycats in Wakefield on Thursday nights used to wait for the sound of taxi pulling up n key going in lock so exciting

I so much wanted to be her that’s when istarted dressing iwould fantasise about getting caught

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By *axNorthMan
6 weeks ago

Sutton


"Used to hear mum in the next room after my parents split I could hear everything through a heating vent that connected our two bedrooms I used to wear her tights n lay there wanking myself silly

She used to go to a nightclub called pussycats in Wakefield on Thursday nights used to wait for the sound of taxi pulling up n key going in lock so exciting

I so much wanted to be her that’s when istarted dressing iwould fantasise about getting caught "

Incredible legs 😍

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By *cottishstevexMan
6 weeks ago

Edinburgh

Similar here , early teens gazing for Xmas presents in mums catalogue , always drawn to underwear pages ,such a turn on , this led me to rummaging in drawers etc, never looked back

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By *appylondonMan
5 weeks ago

West London

For laugh my first girlfriend (age 19) dressed me up in her underwear, bra, knickers and camisole. We both found it incredibly horny and we fucked like rabbits while I was dressed.

After that I’ve worn women’s underwear and lingerie now and then for fun and sex. Some girlfriends found it hot, some not. I’ve yet to have sex with a man while in lingerie, much to my annoyance.

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By *hubSub87Man
5 weeks ago

Grimsby

Like a few others I started with mums underwear, loved the feel of them. I've been on and off over the years but I keep coming back to it

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By *ustPeekinMan
5 weeks ago

Alresford

When I was 11. School uniform.

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By *i_cd_4_uTV/TS
5 weeks ago

Stockport

Same as a lot here, started sisters and mums stuff. First around 10/11 was sistres school tights and swim suit, was somthing about the smoothness that got me excited lol Then onto underwear and mums lingerie x

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By *ll foxMan
5 weeks ago

WORKSOP

I started when I was about 13/14 !

Sisters things really

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By *acyboyTV/TS
5 weeks ago

Southampton

I started around 10/11 wearing mums nylons. Obviously i kept that love a secret from my girlfriends over the next few years although I did have two separate girls that introduced the idea of me wearing their panties for our regular sexy fun. The funny thing with both of them is that I think they got a kick out of thinking they were making me do something that I didn’t want to do. Of course the truth was that I loved wearing their sexy panties whilst we had fun. I just couldn’t show it too much. With one of them I was also “coerced” to wear her tights under my jeans.

I later had a fling with a married woman who memorably confessed that she really wanted me to wear her stockings and suspender belt whilst we made love. She was worried I would think her kinky and go off her! I “reluctantly” agreed to do so leading to fantastic sex. I swear I do not recall ever giving any of the females and idea that I was already secretly wearing lingerie for home alone wanking sessions!

I’m so happy and lucky to be married to a woman that has no problems with me wearing lingerie and even occasionally buys me new panties or hold ups etc. she also takes many of the images and clips of me dressed in lingerie. When I’m dressed she does not find it a turn on for herself but does enjoy the fact that I get turned on if that makes sense?

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By *unman3268TV/TS
5 weeks ago

kirkwall

Started at about 14 when still living at home. Great when folks out and had the house to myself. Carried on all through my life.

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By *ack4more500Man
5 weeks ago

Muff

I started with my mums and older sisters tights years ago

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By *dstefiMan
5 weeks ago

Solihull


"When I’m dressed she does not find it a turn on for herself but does enjoy the fact that I get turned on if that makes sense?"

Perfect sense, that's exactly how my wife views it too. We're lucky men!

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