FabGuys.com forum: What started you down the path of crossdressing

By *atexlover50 OP Man
4 weeks ago

Barton upon humber

I will start.

I was about 15 and was looking through a porn mag. Yeah that long ago. I remember seeing a woman wearing a German army uniform.

She stripped down to the usual stockings, suspenders and a bra.

I was more turned on in what she was wearing then looking at her figure especially the stockings. Though I wounder what they would feel like on.

After getting over my nerves I bought a pair.

Rushed home and made sure no one was in. Just opening the packet and feeling how silky they were felt amazing.

I quickly got undressed and after several attempts I managed to get them on without a ladder in sight.

Just looking at myself in the mirror and seeing my stocking covers legs I knew from that day on my life would be different and I wanted to explore all females clothing.

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By *althazar_LSMan
4 weeks ago

calne

I first did it back as a teen. Wore a pair of tights and from there on and off I’ve been wearing female clothes when the chances have presented. I always wear women’s underwear have for years now and often wear women’s casual clothes I don’t wear dresses often but on occasion at home I might.

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By *ottom_only_CDTV/TS
4 weeks ago

Near Glasgow

Covid lockdown, boredom and lots of time on my hand.

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By *atexlover50 OP Man
4 weeks ago

Barton upon humber

I also wear sexy knickers all time. Much more comfy.

I have several dresses from cloth to latex.

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By *atexlover50 OP Man
4 weeks ago

Barton upon humber

Started to see me then partner who is my wife now so I stopped dressing. One day I told her a has a thing fur stockings. Now it's snowballed so I wear lots of things as she likes me dressing.

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By *ressed4fun03TV/TS
4 weeks ago

Leics/Warks

In my late teens I house sat for my recently divorced lady boss to feed her dog whilst she was away.

I spent a week sniffing, dressing and wanking in her lingerie.

On her return she grabbed me for a quiet word, she noticed id been through her drawers and asked if id been stealing from her.

In the end I had to admit id been jacking off in her underwear, she said that she was going to pay me for what I did but a couple of days later when on shift with her she handed me a bag and told me it was my payment for looking after the dog.

It was full of lingerie, basques, stockings, baybydolls, knickers, bras, hold ups etc.

She had me wrapped round her finger from that day on and was a fantastic tease.

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By *adame BootsTV/TS
4 weeks ago

Tetbury

My love of high heels started me off, then slowly worked up the body until I am what I am now.

During the summer of 2020 I promised myself that I would do more with it and now go out with others and have a little bit of fun here from time to time.

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By *ell61TV/TS
4 weeks ago

Hatton

It was my Aunties white stiletto shoes and stockings, that stared me off

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By *avebiuk99Man
4 weeks ago

Kings Lynn

I was asked to wear some of my wife's lingerie whilst on cam with another guy, was feeling horny so I went along with his request.

Never in a million years did I think that it would turn me on but it did and I've never stopped wearing it ever since that day.

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By *vsindyTV/TS
4 weeks ago

A place where sheep are warm, or Burnley.

What started me????? My stepsisters panties getting mixed up with my own underwear. Was going to return them, but when I felt them I thought, "why not".

Don't know why I thought that, until that point I never even thought about wearing clothes of the opposite sex, but something just clicked as I put them on, I knew this was me.

Soon (very, very soon), I was wearing her tights, bras, skirts and tops, dresses....even managed to slip into a pair of her strappy heels. It was when I first wore her suspender belt and stockings that I fully realised what a rabbit hole I had fallen down.

Needless to say, she (like most women do) realised someone had been rummaging in her drawers, and this was confirmed when she caught me red handed....well, more cock in hand as I was masturbating furiously whilst wearing her black bra and panties, stockings and suspenders

So yes...its all her fault, she is to blame I turned out to be a cock loving crossdresser

bless her lovely heart xx

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By *fcdTV/TS
4 weeks ago

Southend

No idea why but I’ve been fascinated by knickers pretty much from the off. I’m told as a five year old I’d go rummaging in the hamper for them and once I hit puberty I was trying on my mums and sisters. Once I started work I bought my own though.

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By *itherMan
4 weeks ago

Leeds

I once tried the full thing - stockings, suspenders skirt and blouse and makeup. I don't look the part at 6'4" and 21 stone so haven't bothered since. Nice young slim things can be very attractive.

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By *ustPeekinMan
4 weeks ago

Alresford

Started off with knickers, then it was swim suits and then school uniforms.

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By *amesryan692024Man
4 weeks ago

kilmallock

My neighbour who introduced me to cock on cock fun.brought me to his house wen his wife was out and dressed me up

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By *lueEyesKinksterMan
4 weeks ago

Cheltenham

School play .. wore a pair of black tights. That first encounter with nylon .. never to be forgotten. Still slipping into tights and stockings forty years later.

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By *appylondonMan
4 weeks ago

West London

Aged 19 with my first girlfriend, while fooling around naked she dressed me up in her knickers, bra and crop top for a laugh. We both found it really really horny and we had sex with me dressed like that.

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By *amieforfun1973TV/TS
4 weeks ago

bognor regis

I think I’ve always enjoyed lingerie and high heels, Littlewoods catalogues were always enjoyed (those that know, know) and then internet chat rooms got me into wearing things for guys, I was curious and loved being told to wear the wife’s stockings etc and it has devoted from there. Now I have my own things and live to dress up for sexy chats or to meet a man and play x

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By *enry77Man
4 weeks ago

ayrshire

I had access to my aunt's clothes when I used to shop and garden for her. Found some of her knickers on the bedroom floor and couldn't resist. Put them in my pocket and took them home. After that I took lots of her clothes without her knowing and stood in front of my bedroom mirror in her clothes wanking

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By *tephanie SomtimesTV/TS
4 weeks ago

South Derbyshire

My aunt started me off.

She loved fancy dress and on Boxing Day each year she would dress me up in something.

I remember one time it was a pirate with a patch another time a soldier wearing my dad's beret.

However on this occasion we went upstairs to find something and on mum's bed was her suspender panty girdle.

She dressed me up in that with some stockings and paraded me around in front of the family.

I loved it, I think it was all the straps etc.

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By (user no longer on site)
4 weeks ago

Grandma's stuff on floor

My curiosity got the better of me

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By *ikey_KentTV/TS
4 weeks ago

Gillingham

I loved sering girls in tights when I was at school, so first dress up was sisters black tights and her school uniform

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By *nchsolentMan
4 weeks ago

Fareham

The clothes were provided for me I was told to get changed. I didn't want to do was persuaded!

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By *anm56Man
4 weeks ago

Barrow

My mum ! She had a fantastic collection of lingerie and one day I tried her tights on then discovered more stuff basques etc

Been dressing on and off since I was 14

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By *tephanie SomtimesTV/TS
4 weeks ago

South Derbyshire

"I loved sering girls in tights when I was at school, so first dress up was sisters black tights and her school uniform "

I had to wear my sisters green tights for a school play and loved it.

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By *ikey_KentTV/TS
4 weeks ago

Gillingham

"I loved sering girls in tights when I was at school, so first dress up was sisters black tights and her school uniform

I had to wear my sisters green tights for a school play and loved it."

I bet that was really nice

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By *dstefiTV/TS
4 weeks ago

Solihull

My mum's petticoats and slips at a very early age (way before I ever started masturbating; I just liked how the smooth satiny fabric felt, and the elasticated waistbands).

Then the usual fascination with the lingerie pages in her mail order catalogues once I'd started wanking.

One time I moved into a rented house that had been recently vacated by a bunch of student nurses and had the place to myself for a couple of weeks before somebody else moved in. They'd left discarded underwear everywhere (stained panties, laddered stockings and tights, frayed bras with missing clips) and I had the most frenzied fortnight of continual wanking, wearing everything and looking at myself in the mirror, cumming in and on every piece of underwear four or five times a day till it was all absolutely encrusted with my dried-on spunk. Had to bin it all when the other tenant moved in, which was a wrench. And have been addicted to lingerie ever since.

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By *ankatallcostsMan
4 weeks ago

Solihull

I found the pleasure of satin when I first started wanking at 14. For some reason on entry into the bathroom, I seached through the wash bin, and found my moms satin underslip of which I gently rubbed across my erect cock. The feeling was incredible, and led me to wank into my mother in laws satin bra later on in life. I was already having an affair with a lovely lady and arranged to meet another, whom I'd shagged before. I bought her a pair of satin Frenchies, but before we could meet, my wife found them hidden and asked questions. My answer? - "they're mine as my fetish for satin is so great". So now she knows I love satin and I wear it for her.

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By *ustPeekinMan
4 weeks ago

Alresford

An obsession with the softness of girls’ knickers compared to the tighty whities I had to wear to school. That led me to the knicker drawer and later to dressing in girls school uniform.

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By (user no longer on site)
4 weeks ago

Glamour.

Nice to wear high heels.

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By *yrdresser30TV/TS
4 weeks ago

Ayr

"Glamour.

Nice to wear high heels. "

Yes it is x

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By *heffbagMan
4 weeks ago

Rotherhsm

Started early as had airing cupboard in my bedroom so used to wear mums slips at night and try bras on

Dressed once for my first lad I had fun with in his sisters uniform

Time has moved on and I sometimes dressed but now I work alone and dress every day there with my own wardrobe. Just enjoy the styles and feeling of it x

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By *racycockloverTV/TS
4 weeks ago

Central London

I went to a park which was a cruising area at night to suck a Cock for the 1st time.

I met a guy there and he took me back to his flat,he asked me to wear stockings and suspenders for him.

That was 25 years ago and I still dress up now.

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By *cunnyAprilTV/TS
4 weeks ago

Scunthorpe

When my wife left I saw a few women but then remembered that I like men also so I start with that, gradually men asked me to wear panties, then stockings and gradually fully dressed, mostly because men wanted me to. After a while I realised that getting dressed up put me in the mood faster. Now I will do either, I have two profiles on here one for each

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By *toxyMan
4 weeks ago

Bicester

Wore some sexy lingerie after finding mum’s naughty drawer

Years later an aunt by marriage used to dress me up in lingerie as did an ex gf

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By (user no longer on site)
3 weeks ago

After watching the sexy Ladyboys of Bangkok.

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By *issy SiMan
3 weeks ago

Horsham

Borrowing my sister's and mother's cardigans and wearing them in public

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By *shubMan
3 weeks ago

manningtree

wearing my mums tights and they felt so good !

Used to slip on a pair, get into bed and squirm around in them until I came.

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By *orny747Man
3 weeks ago

andover

Wearing my mum's underwear

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By *ippaTTV/TS
3 weeks ago

Hedge end

I started at the age of eight, wearing a pair of tights I loved the sensation on my leg's,

Now I'm a complete slut for dressing up.

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By *ampell1Man
3 weeks ago

Liverpool

Sisters an auntys underwear

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By *olly SwallowsTV/TS
3 weeks ago

Exeter/London

Was a dare by a female friend and uni and never looked back xx

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By *appysfTV/TS
3 weeks ago

ash

I started in my teens, watching porn and thought I preferred the sight of cock more but liked the pvc cloths of women and thought I’d see what it’d be like pretending to be the woman, feeling so horny dressed gets me right in the mood x

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By *unboytoyMan
3 weeks ago

scotland

Simply putting on my ex’s used knickers my cock got uncontrollably hard .

Was simple as that

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By *ckermanMan
3 weeks ago

newport

When i was teenage i used to like getting naked in naughty places, we had a boarded floor loft but not a proper conversion. I and my dad had a model railway up there so wasnt usual to be in the loft.

I used to go up and get naked listening to family in the rest of the house. But one day while rumaging found so old maybe 1960's dresses of my mums. Felt so kinky slipping one of those on and seeing my hard cock poking the front out.

Thats was it for some years until i met a photographer who wanted me in lingerie, and i discovered i enjoyed dressing up in lacy panties and hold up stocking. Its been a while though, not a regular thing for me

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By *elenaCDTV/TS
3 weeks ago

In the sticks Somerset

At the age of 15 parents away for the weekend, looking through a mail order catalogue, got to the lingerie section, got a bit aroused especially suspenders and bras. Wondered what it must feel like, so raided mother's lingerie drawer found an open bottom full girdle with suspenders pulled it on and wow so hard just had to wank. Spent the rest of the weekend wearing it. And wanking!

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By *uriouslyColMan
3 weeks ago

colchester

There’s always been a part of me that’s always wanted to be female, who enjoys being feminine. My first experiences were about 15 years ago, and the moment I tried it, I felt so happy but it felt so right. That lasted a few weeks then in moved in with my gf. Now fast forward to today and I bought a skirt and a pack of panties.

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By *mandaWhenDressedMan
3 weeks ago

around

Remember a few of us at school would forget our PE kit and have to do it in just out pants. The girls knickers were so colourful and looked great. Soon realised my sister's were similar so I had to try.

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By *ub bd4Man
2 weeks ago

Bradford

Started as a bit of self humiliation during COVID, rough as. Then moved and most guys in Bradford are more into sissy sluts

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By *dstefiTV/TS
2 weeks ago

Solihull

This happened donkey's years ago when I was at university.

So there was a Rag Week disco on at the students union, fancy dress themed. I knew a bunch of girls (as drinking buddy type friends, wasn't going out with any of them), and I tentatively suggested going in drag. Fay, the most outspoken and fearless of them, thought it was a brilliant idea and offered to do a full clothes swap as we were similar sizes.

They did a full makeover on me, Fay and her friends Sian and Anne. Lent me a dress, holdup black fishnet stockings, black bra (with some more stockings stuffed in to give me an outline), low heels I could walk in, and even a pair of Fay's black lace panties (I hadn't dared ask for them and was going to wear my own pants, but her attitude was go big or go home; I said she was fearless), then styled my hair as best they could with some clips and accessories and did my makeup: foundation and blusher, eyeliner, mascara and lipstick.

I wouldn't say I was completely passable as a girl but it was close enough for an evening out, and such that I felt more comfortable using the ladies' toilets at the disco. Walking on the city streets in the evening in a summer dress, feeling the sensation of Fay's tight, brief panties barely covering my cock and balls and ass, her bra around my chest and the fishnets on my bare legs was quite something, as was walking in heels and the way they naturally seem to make one's hips sway in a more feminine way. Of course I was immensely turned on, and had to wait till I got home much later to masturbate a couple of times at the memory, but the friendship we had was of the sort where this was all just a great laugh rather than anything that would turn sexual.

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By *ylons22Man
2 weeks ago

Tipton

youngest memories were probably at around 8 years old with my mothers friend visiting, always wearing american tan or coffee coloued tight, use to sit on the floor and spend ages watching her leg movements.

then at 13 i discovered my mothers secret box of nylons, knickers & suspender belts etc... hidden in the bottom of her wardrobe, as soon as i had the house to myself i curiously headed straight for her collection & emptied the contents onto her bed, i then selected a pair of black fishnet stockings, black suspender belt & matching knickers.

after slipping them on the wrong way of course, knickers under the suspender belt instead of over the top, i stood in front of her full length mirror completely amazed at the sexy look & feel, my cock instantly sprang into life & never felt so hard.

3 good hard wanks that day & have been completely addicted ever since, I'd head to her secret box whenever i could & dress in her stuff, sometimes I'd spend the entire night laying in bed in her gear wanking away, never cum on any of her stuff sadly as i was so worried about getting caught.

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By *enry77Man
2 weeks ago

ayrshire

When I started wearing panties and stockings more than 60 years ago it was so exciting that I used to cum almost as soon as I'd pull them on. Whenever I use panties that font belong to me and wank I always think of the owner whoever they are

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By *reddi400Man
2 weeks ago

ayr

"When I started wearing panties and stockings more than 60 years ago it was so exciting that I used to cum almost as soon as I'd pull them on. Whenever I use panties that dont belong to me and wank I always think of the owner whoever they are "

yes very similar here, started with mums underwear when about 10

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By *ngietimeTV/TS
2 weeks ago

cambridge

When first married....being surrounded daily by my attractive wifes femme world. Slipped into her things and have dressed since.

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By *eniReesTV/TS
2 weeks ago

Pembroke

Wearing bra, girdle and stockings while sitting around with my cousin and her older friend while they tried on their clothes for Saturday night out

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By (user no longer on site)
2 weeks ago

Learned from RuPaul Drag Show.

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By *athCDTV/TS
2 weeks ago

Morpeth

Seeing my older sisters baby dolls negligee, I was about 12 and tried the knickers on first, I had an erection but didn't know about wanking, so I would rub the end of my cock and I would get this gorgeous feeling, then the shame, I vowed never to do that again. I didn't know it at the time I was having dry climaxes and later at school when my class mates were talking about walking and cumming, I joined in, as if I knew. I couldn't wait to get home and work my foreskin over the helmet and then I had this gorgeous feeling again and I realised I'd been having dry wanks. By this time I was producing cum. So I started wearing my sists slips then her bra and knickers girdle with stocking. I thought when I met my late wife and got married I'd be able to stop. Ha ha after 6 months I told her and she welcomed Kathy into our bedroom the rest is history

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By *ackie5665TV/TS
2 weeks ago

Wisbech

I must of been about 13 and became fascinated by my sisters knee length white boots. I tried to put them on but they were a bit too small so I put on a pair of her tights to see if that made me more slippery. It worked but it was the feeling of the tights that set me off on this wonderful lifestyle.

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By *arrie cardieTV/TS
2 weeks ago

Southampton

Lived in a block of flats and mum and her friends used to meet up for coffees, and a chat . All of them would be in there late 20s I guess. They didn't bother getting dressed, just in their quilted dressing gowns. Got a bit hot in the flat so off came the dressing gowns to reveal gorgeous nylon and chiffon nighties. They looked amazing and as soon as possible I tried on my mums short black nightie, I was hooked xxx

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By *ifun1Man
2 weeks ago

Bath

Started with dressing up games at a friends house, knickers,tights,dress and a pair of strappy wedge heels. Soon got into wearing mums american tan tights,found a peep hole bra too and especially loved strappy heels. Found older guys at local cottages liked it too.

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By *laretv42TV/TS
2 weeks ago

BRIDGEND

I was jealous of the girls becoming women discovering their sex and how to use it

Growing breasts becoming shapely and the attention they had by wearing nice clothes

I found my mams lingerie drawer when i was about twelve the original wonder bras and thongs

Fifteen she asked me if i had been wearing her lingerie

Denied it all but wanted to say yes xxx

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By *allyridesTV/TS
2 weeks ago

Swindon

Was 20 years old and went to a party. Got a bit pissed and started dancing with a girl(well that's what I thought)

Started snogging and discovered her extra bit!!!. Carried on and lifted her skirt. Found her stockings and knickers so so sexy and when I sobered up wanted to wear them. And the rest is history xx

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By *dlegs2024TV/TS
2 weeks ago

Northampton

I started when I was 14 wearing my mums stockings and suspenders luckily she had quite a lot of them so I was in kinky heaven! Over the years I’ve worn ex girlfriends, sister in law and even my ex mother in laws! Just love the way stockings and suspenders look and feel. Now I have my own and dress at every opportunity!

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By *ammy aka SammyTV/TS
2 weeks ago

Bedford

Really don't know ,I was dressing in girls clothes as I remember as far back as a 10year old kids .kinda just felt natural, never understood why I got laughed at and beat up so much until my late teens. Bearing in mind there was very little in the way of sex education and no such thing as the internet. Now at age 74 I still don't really know why ,and ive never wanted to be a woman hey ho xx

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By *egancdfunTV/TS
2 weeks ago

Waddington

My story is a bit weird. I had an aunty that seemed prim and proper but used to leave her finest lingerie hanging around. I was mid teens and would feel them but do nothing else.

I then went to rocky horror dressed for a bet and loved it.

Fast forward then military and at stag functions we all got dressed up and mine got more realistic each time (married) everybody loved it.

Then a few years s a go I did it for me!

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By *ayne DesireTV/TS
2 weeks ago

Gloucester

"Covid lockdown, boredom and lots of time on my hand."

Gosh! You are really good at it in such a short time. I find Scots trannies the most attractive

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By *ayne DesireTV/TS
2 weeks ago

Gloucester

"Really don't know ,I was dressing in girls clothes as I remember as far back as a 10year old kids .kinda just felt natural, never understood why I got laughed at and beat up so much until my late teens. Bearing in mind there was very little in the way of sex education and no such thing as the internet. Now at age 74 I still don't really know why ,and ive never wanted to be a woman hey ho xx "

I started dressing at two and a half and chasing men at that age , too. Cannot believe how i was when i look so far back.

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By *ottom_only_CDTV/TS
4 days ago

Near Glasgow

Lockdown, used to a top only who was into tgirls and dressers. Had a regular cd who's clothes I kept secretly for her.

During lockdown out of curiosity I started trying them on. This led to me exploring my feminine side. Went from just dressing to full makeup up and smooth body. Then the ultimate, to becoming a total bottom.

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By *ose_QuartzTV/TS
4 days ago

Berkshire

I was always fascinated by magicians assistants in my teens. It must of been the fishnet tights and leotards etc and how they would always find themselves tied up or sawn in half in one of the boxes where at the end you would see their legs dangling 😂 I also do a lot of artwork that nearly always involves pin-up girls that heavily influenced me as well. As you can see I’ve been dressing ever since lol

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By *ollyMan
4 days ago

Downham market

First I tried knickers, then tights and it made me feel so sexy and feminine. I don't get a chance to dress up very often but when I do I love it, wig, lingerie, skirt, lipstick etc.

I've had a few fantastic meetings with other cds and a beautiful trans. It felt so natural for me x

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By *q oralistMan
4 days ago

Torquay

Trying on my wife's sexy panties and finding ti got me hard. Graduated to suspenders, stockings bras and see though nighties

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By *andaTV/TS
4 days ago

Worcester Park Surrey

Always loved lingerie on women, then through porn started looking at trans ladies all dressed up. Watching them have sex and then a switch went inside me.

I then started having sex with trans ladies until one told me I would be better as a trans lady with my figure.

I then went out and bought my own lingerie and loved the feeling. Tried my wife’s dildo, which felt amazing. Then bought bigger cock shaped dildoes and then I was addicted. I got fucked by men and loved it and also started HRT estrogen every so often.

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By *atalieCDTV85TV/TS
4 days ago

Bury St Edmunds

I've always appreciated women's clothes and had always wanted to try, so when I got my own place I was able to start.

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By *ssexrob99Man
4 days ago

Broxbourne

I was on holiday one of the evening entertainment nights was a cross dressing thing which I really didn't fancy but the group we was in thought it would be a great laugh my girlfriend I was with kept on saying it would be fun so I ended up in stockings suspenders a skirt bra and a white blouse trousers was I got a amazing erection getting ready and it just wouldn't go down she had to give me a bj to try and get rid of it that never worked so the inevitable happend she got on top and rode me like hell eventually it subsided and we managed to join in the fun but all night her hands were up my skirt having a feel we had to go off for a fuck twice then back at hotel room she wanted me to stay dressed all night she couldn't leave me alone every night after that on holiday I dressed up in her stuff.

Been hooked ever since

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By *illin32Man
3 days ago

here

Mine was same school play I think I had one of my first hardons on stage

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By *ustPeekinMan
3 days ago

Alresford

An obsession with the softness of knickers which led to me trying them on. From there to dressing up was a short step.

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By *i_cd_4_uTV/TS
3 days ago

Stockport

Sisters school tights and swimsuit x the soft feeling was amazing x was around 10/11

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By *dstefiTV/TS
3 days ago

Solihull

One more story from my formative years. Wife and I went to a live Rocky Horror show in Bristol. Fancy dress as one of the characters is the thing with RH, but I was still a bit too timid to go as Frank N Furter in drag, so we went with me as preppy Brad and wife as slutty Janet.

When we got home I realised I'd done it wrong, having seen so many blokes out and dressed in lingerie, so asked if I could put all her gear on: black basque, gloves, fishnets and heels. We then had the hottest, dirtiest sex we'd ever had up to that point and I felt so right, dressed up as a slut and cumming like one.

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By *ig3Man
3 days ago

Maldon

When is was 13 was round a mates house the laundry basket was in the toilet opened it up there were loads of his mum's knickers in it just had to investigate

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By *ipantyMan
3 days ago

kilmarnock

remember seeing my friends mum walking about in stockings and suspenders in front of us

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By *ichelleclassyCDTV/TS
3 days ago

Shaw

Just after I got married at 21 my wife had sexy lingerie so decided to wear her Basque and do my makeup and it felt amazing did it a few times before stuff got in the way and only got back into dressing when I joined the site and I absolutely love it nothing better than doing your makeup and wearing sexy clothes and underwear and having fun xxx

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By *atty70Man
3 days ago

leeds

Few years back a guy asked me to wear panties for him, was so turned on by it I carried on

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By *d sometimesTV/TS
3 days ago

Melton Mowbray

Older sister had a big dressing up box in her room for her and her pals to play with her. When she didn't have any pals to play with her she would dress me up to play her games. I soon loved the look and feel of the clothes and feeling feminine.

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By *ost and lust fuelledMan
3 days ago

st.helens

I was obsessed with my friends very sensual mum. She wore stockings and suspenders and such amazing heels and skirts.

I found myself looking through her underwear drawer and stole a pair of hold ups and used to wear them as well as play with myself in them

Later, i had a girlfriend who was very domme and liked me to wear panties

The final and biggest drive being a domme i met years later making me dress for her on clothes owned by a previous sissy and sucking the cock of another of her subs

The drift to matching my subby bi side with crossdressing being complete from then on.

Even though ive had a loss of confidence and a break from crossdressing this year i know its just a matter of time before i start again

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By *ark81777Man
3 days ago

Cardiff

My brother started dressing from an early age wearing mums things and now fully transitioned.

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By *elanie_welshTV/TS
3 days ago

Newport

I must have been about 12/13. Was hanging the washing up on the line and stopped when I got to a white satin tanga of my mums. It felt so different I was amazed at the silky softness. I felt a stirring on my pants.

I took the pair went to the bathroom, locked the door and tried them on. OMG the feeling was amazing as I slipped them up my legs, I had a raging hard on by the time they were on and experienced my first orgasm. I made a real mess of them and panicked that I would be caught, so washed them quickly and hung them up.

After that I was hooked, I would take her panties from the wash basket so I wouldn’t be found out. Found her wedding lingerie up in the attic, slipping on her stockings, g string and basque I knew I always wanted to dress.

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By *ini1440Man
3 days ago

STOKE-ON-TRENT

Started by always looking at the underwear pages of the old catalogues, then when around 15 started babysitting for my older sister at her house.

She always dressed nice and one night i found her underwear draw omg babysitting from then on was amazing x

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By (user no longer on site)
3 days ago

Glamour.

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By *hilup2Man
3 days ago

Pulborough

For me it started when I wore tights and skirt belonging to a classmate in a school play and developed into borrowing girlfriends panties to wear and wank into and one of the best moments was realising I could squeeze into the velvet dress of a girl I was living with at university.

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By *ighlands fellaMan
3 days ago

thurso

Went to a fancy dress party I was dressed as my gf she was dressed as me.

It turned her on seeing me like that so I kept doing it for her

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By *uffolkboi0709Man
2 days ago

Lowestoft

Mine started as a kid. I had an older sister which meant I was essentially a dress up doll for her. She once dressed me head to toe in a bra,dress etc which i think was probably the trigger.

In my teens i then started wearing some of her Lingerie and couldnt get enough of it. Stopped for a bit when I met my wife but pretty soon started wearing hers. She caught me a few years ago but its now gone full circle and she dresses me too

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By *oodsman2Man
2 days ago

Galashiels

Ex left some lingerie behind when we parted. Curiosity got the better of me so I tried some on. Immediately loved the feeling and felt so horny. Still love getting into something lacy or silky when I can. xx

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By *ampell1Man
2 days ago

Liverpool

In my teens looking at my aunty underwear stockings

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By *ldmanMan
2 days ago

Rawcliffe Bridge.

I was asked by an old guy if I'd like to try some female clothes on, and did so.

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By *ike 57Man
2 days ago

clonmel

did he dress as well?

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By *ldmanMan
2 days ago

Rawcliffe Bridge.

No. He wasn't into dressing, only dressing me, and then undressing me.

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By *eicester38Man
2 days ago

Leicester

I was 16 and started trying my aunties thongs and bras on when I used to be at her house alone

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By *tuart333Man
2 days ago

STAFFORD

never thought about it for mayself until a guy asked me to dress for him - he had the clothes for me and when dressed I felt like a slut and loved it

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By *laretv42TV/TS
2 days ago

BRIDGEND

Its an escape from a boring drab male world

And i become very bi as soon as i open my knicker drawer i need to be used like a girl to get felt up and to please a man xxx

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