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When did you start to crossdress and why ?

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By *ustina OP   TV/TS
1 week ago

cardiff

When I was in my late teens, I occasionally used to like trying on my mother's bra, corset and tights but didnt think too much of it. Just my little secret.

Fast forward to my early thirties, when I started seeing men. I enjoyed letting my gay side have some fun but there was something missing. I needed to feminise myself whilst carrying out these sex acts.

A bit of make up here and there, a bra underneath my shirt and stockings underneath my trousers. It was quite exciting at the time but I knew I could really look the part if I put my mind to it. That entailed a visit to a shop in Walthamstow to buy breast forms, a wig and get fitted for a bra. The experience was exhilarating and the ladies in the shop were so wonderful and understanding.

I've had some fantastic meets while dressed and made up. Nowadays I will dress if I get the urge. Otherwise why would I be contemplating buying a breastplate. However, I now sort of prefer being naked between the sheets, especially with the right man.

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By *aySub99Man
1 week ago

Northampton

at 16 I just wanted to feel cute and have fun like that.. ordered my own stuff and got some makeup from Boots and tried things out.. really enjoyed it, and the attention

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By *nchsolentMan
1 week ago

Fareham

Master told me to

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By *orcsmatMan
1 week ago

Kidderminster

I have dressed up and in public, but only on a couple of occasions.

I have put pen to paper about those.

If anyone wants to read them, message and I'll send a link.

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By *ubsissyforuMan
1 week ago

nr Bourne lincs

My 1st meeting was with a cd. And I found it really turned me on. Since then I love dressing up xx

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By *dstefiMan
1 week ago

Solihull

I'd always messed about with my mum's underwear when I got the chance but my big turning point was moving into a rented house that had just been vacated by a load of student nurses and left a bit messy. Cast off underwear everywhere and I had the place to myself for a couple of weeks before another tenant moved in, and in that fortnight I absolutely wanked myself stupid in those unwanted panties, bras and tights till every item was crusted in my dried on sperm.

No going back after that

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By *islut39Man
1 week ago

grantham

Early Teens, used to wear my sisters underwear and stockings. Turned me on a lot and used to stroke whilst like it, fast forward to 20’s and started to wear heels thongs and stockings with an ex and she got me into pegging too and now for the last 4 years I’ve bought all my own stuff, have breast plate and wig and dress as often as I can. I absolutely love it

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By *atty70Man
1 week ago

waterloo

Early teens for a neighbour and then on and off in my twenties, I only dress if I’m

Asked to

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By *oxy 11Man
1 week ago

Doncaster

I was in my early teens started with mums and sisters clothes

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By *ylonplesureTV/TS
1 week ago

Stone (staffs)

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By *othslutTV/TS
1 week ago

London

I like lingerie more than men’s underwear and it escalated after I found out guys liked me in it.

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By *irty DeniseTV/TS
1 week ago

Penzance

I first started dressing as a young boy in mums clothes as we did back then dressing up.

My mother always wanted a girl so I was treated as one. When puberty hit I was into dressing up in mums lingerie and I soon discovered my gay side with a neighbour who took my virginity.

Mum got fed up with me pinching her lingerie so she bought me my own and it went on from there.

I love the feel of silk and satins next to my skin.

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By *rookeTVTV/TS
1 week ago

Linwood

a guy in a cottage wanted me to dress in the stuff he brought in a carrier bag, i liked it and never looked back x

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By *ustPeekinMan
1 week ago

Alresford

I was about to 11 when I started to borrow cotton knickers from sister and girl next door. I’d always been obsessed with the softness of the material! From there it was a short step to wearing them. After that it was swim suits and school uniform.

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By *elenaCDTV/TS
1 week ago

In the sticks Somerset

Parents went away for the weekend when I was 15.

Found mothers open bottom full length suspender girdle in the washing. Curious how something tight felt to wear so tried it on, instant erection. Rest is history

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By *ustcurious778Man
1 week ago

Bridgend

Found a sheer red babydoll in my mums drawer and took it to the bathroom to try on. Never looked back. Now always prefer to be wearing satin and lace

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By *al423Man
1 week ago

Stoke-on-Trent

I was 12, me and I mate got caught wanking each other by his older sister, she made us wear her underwear and suck each other off or she’d tell our parents

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By *irtytrukkaTV/TS
1 week ago

barton

I dressed for a boyfriend in my teens

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By *o90Man
1 week ago

South Oxon

Aged 10, I found a pair of my Sister in Laws panties in the wash basket and decided to try them on ( no idea why) but there was also an aroma that got me hard immediately. So girls panties became my thing for a while then I generated to full dressing, which I occasionally still indulge in.

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By *oodsman2Man
1 week ago

Galashiels

When I split with my ex gf she left a few lingerie items behind. Curiosity go thte better of me and I tried them on. Felt so horny straight away. I haven't gone full cd - lingerie only until now - but I wouldn't rule it out in the future x

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By *punky knickersTV/TS
1 week ago

Flintshire

An older lad used to dress me up in his sisters knickers and tights then got me my first suspender belt and stockings

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By *ontylad87Man
1 week ago

pontefract

Ex gf got me into it, she started to dominate me!

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By *aulBiBottomMan
1 week ago

nr Longbridge

Knickers and tights on the radiator when living at home, tried them on and that was it some of the best wanks had, then as I have got older buying my own and wearing for edging sessions and then with guys when meeting if they also enjoyed.

It's an additional thing that many guys enjoy, to feel stockings on me and on others is so fucking horny

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By *isa220TV/TS
1 week ago

Greenock

When camming for guys guys wanted me to wear wife lingerie her panties at first never looked back dress now most days

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By *ate500TV/TS
1 week ago

Newcastle/Durham

It all started for me back in 1980 at a fancy dress party as one of Charlie's Angels. It was just a laugh but secretly fucking loved everything about it.

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By *lueEyesKinksterMan
1 week ago

Cheltenham

School play at 16, wore black tights. Have never looked back. Still addicted to nylons 40 years plus later.

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