FabSwingers.com forum: First/early crossdressing experiences?

By *iss Sophiebelle OP TV/TS
15 weeks ago

Reading

Hi - anyone want to chat about their first/early crossdressing experiences?

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By *iss Sophiebelle OP TV/TS
14 weeks ago

Reading

Had some lovely private messages since posting this...any more?

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By *ndyelyMan
14 weeks ago

chatteris

Mine was in a allotment shed with step dad's mate

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By *nly1meMan
14 weeks ago

here there n everywhere

wud love to hear more x

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By *urabriteMan
14 weeks ago

stafford

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By *usie pTV/TS
14 weeks ago

taunton

My first experience was a good few years ago, I decided to dress late one night had collected up a bit of gear from charity shops mini skirt etc and bought some stockings and suspenders in a party shop so got dressed up and went cruising to a known layby with cottage down in Devon, it was about 2 in the morning there were a couple of cars parked up but couldn't see anyone so after a bit went into the cottage for a pee was startled to see someone in there so went into a closet and when I came out he was stood there wanking his cock in clear view he said suck me so I did then another guy came in and started feeling me up in the end there were five guys in there they had me stripped to stockings, suspenders and knee length boots only, ended up in a cock frenzy, spunk everywhere fook knows where they all came from at that time of night when I came out it was 4 o clock lol. The whole situation was crazy really but cock brain had taken over and what still surprises me even to this day is the amount of masculine guys who partake of gurl pleasure even with some of us who are fairly masculine ourselves.

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By *tephanieuktvTV/TS
14 weeks ago

bristol

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By *he_13th_ghostWoman
14 weeks ago

Swindon

I used to dress up as male characters for things and years later I realised I was transgender male.

I remember just feeling more confident and safe inside my skin when I cross dressed.

I went to a friend's uni party and it was *dress like the opposite gender* and I went as a man and it just was the real start of everything slotting into place.

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By *ednesday 2023TV/TS
14 weeks ago

Stortford

Like most, I started as a teenager in panties and stockings, it wasn't until my 40s I decided I wanted more, First pair of heels a bought, stood up and it was an instant YES! follwed by the thrill of slipping on a skirt, then wig and make up.

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By *hisismeXXXMan
14 weeks ago

Welsh Wales

I’ve posted before about an ex of mine when I was 18-21, who really opened my eyes to a whole world of kink. Older woman, boss in work. Looking back from my perspective now I was taken advantage of really, but I certainly didn’t care, I was young, dumb and full of cum as they say.

At one point she suggested she’d like to see what I looked like in women’s underwear and I went with it for fun. So she dressed me in her lingerie that night and boy did it turn her on.

So we progressed quickly to her making me up while wearing her lingerie to then her buying me a basque of my own, before we’d go shopping together for matching lingerie which 30 odd years ago did raise a few eyebrows.

We’d wear the same outfits at home, then it progressed to going out for runs in the car to ‘lovers lane’ areas (what I know now is dogging spots) with us in just the outfits. Then, we started going out for the night with our matching lingerie under our clothes - me dressed for a normal night out but sexy lingerie underneath- and we couldn’t keep our hands off each other.

Dressing up never really did anything for me personally, but her going wild for it certainly did!

That leads us to another story, when we went on our first holiday, to Playa Del Ingles and the most wonderful encounter with an incredibly sexy TV that ended with my partner wanking me off over them. The incident that awoke a life long passion for all things trans…

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By *enuinebiMan
14 weeks ago

Wellingborough

Dressed by an older family friend some fifty years ago

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By *ikerbitch777TV/TS
14 weeks ago

thirsk

My first time was a family friend as he caught me going through his wife's panty draw. He told me t pick sine lingerie then put it on n go down stairs in to the living room. I picked black suspenders stockings panties n bra. Then went down as he had told me too..... x

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By *exy dee 69TV/TS
14 weeks ago

Manchester

I did a fancy dress dressed as female dress panties makeup lipstick nails I was helped by two females looking okay i had longish fair ginger hair didn’t win after went to the bar a guy was sat on stool putting his hand on my back asking me questions name etc I was just playing along my friends we’re looking he moved and one leg was rubbing my against my thigh I didn’t move I just didn’t want him to get embarrassed if he found out his hand was rubbing against my back and down to my bottom one of the girls walked over asking if I was okay took the drinks he smiled and asked what we was doing later I replied drinks some dancing and rubbing my hip against him some late night fun I could see him now getting excited i went back to my friends he looked at me I felt his eyes checking out my bum I smooth dress add a little wiggle we left I went got changed one girl friend help me change asi strip I got excited she smiled and rubbing my penis slowly and sucking me went on the balcony and had sex she said after I should dress more often we met the rest I tee shirt shorts keep them white panties on I forgot to remove the nails paint feet okay in trainers pink so what much later going to hotel some guys got talking one asking me what the nails was about I explain he said dam missing a fun night it was a laugh did you look good I don’t know why i said this but ( yes who could resist a girl in a white dress white panties pink finger and toe nails and smiled still have the panties on we both new something was going too happen he said you’re pink fingers would look nice around my cock let’s find out by the pool we go there I pulled hi shorts on pants down too hold and make him hard wet I pulled my shorts down but left panties on pleasing him rubbing my mouth on his wet penis slowly rubbing it in my mouth letting it play on my tongue mmm could taste the cum I started playing with my penis he lay on a sun bed I climbed on him rubbing my penis slowly against his he took hold and then rubbing them together moving up to his mouth ?? he succeeded in making me cum

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By *usie pTV/TS
14 weeks ago

taunton

A couple of these tales deffo need more expansion and I am sure the divine missophiebelle has something to tell us all.

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By *ndrea54TV/TS
14 weeks ago

cambridge

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By *ressuploverTV/TS
14 weeks ago

Cardiff

Always loved the look and feel of satin lingerie, stockings, etc. An ex left some behind and I gave them a go…

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By *onkoMan
14 weeks ago

here and there

Not especially

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By *aulaC2022TV/TS
14 weeks ago

Clare

Mine was when my neighbour flashed her panties at me maybe accidentally. We were both 13. After that I went in to her drawers and tried on what I found. I ended up trying on her mother's stockings or her tight dresses.

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By *ickylouCouple
14 weeks ago

Will be at the UTB social in Birmingham tomorrow

fully dressed in the red lingerie from our pics with male clothes on top. Vicky last time kept exposing me as we talked to people

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By *tephanie 9090TV/TS
14 weeks ago

BISHOP

During Covid, my OH was working for the NHS and I was bored. Stephanie awoke and she tried on some OH's outfits, and to her surprise most of them fitted. Shoes were a challenge, too small. Being dressed was amazing and Stephanie started to order online. Stephanie arose and her world changed soo much. Stephanie is here to stay.

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By *ini1275Man
14 weeks ago

stoke on trent

"During Covid, my OH was working for the NHS and I was bored. Stephanie awoke and she tried on some OH's outfits, and to her surprise most of them fitted. Shoes were a challenge, too small. Being dressed was amazing and Stephanie started to order online. Stephanie arose and her world changed soo much. Stephanie is here to stay.

Wow you look amazing x

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By *harlotteBrooke9TV/TS
14 weeks ago

Manchester

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By *indacxd2000TV/TS
14 weeks ago

Knocklyon

My sisters red panties just had to be tried on.

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By *atin braTV/TS
14 weeks ago

bristol

mine was my older sisters satin push up bra i was about 17 and then after that it was her knickers . suspenders im sure she knew cus she would make random comments .. and then i just bought my own

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By *andycd20000TV/TS
13 weeks ago

limerick side of ennis.

I started with my Mum's and Sis panties. Never looked back

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By *aracd69TV/TS
13 weeks ago

ivybridge

I started with the lodgers stockings, she was a trainee nurse always wore hold ups or suspenders so had plenty to my disposal, tried on the hold ups instant hard on so put a stocking on that to never looked back just wish i had more oppituinites to dresd

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By (user no longer on site)
13 weeks ago

A couple of years ago a fbuddy took her panties off and past them to me and told me to put them on. I wore them as she sucked my cock through them. I loved how they felt on and how I feel through them. So I wear the wifes when she's out

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By *uiteCurlyMan
13 weeks ago

Glastonbury

There are too many to relate. It’s difficult when you spend a lot of your life not wanting to be a boy. Oh well x

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By *itginger101Man
13 weeks ago

Termonfeckin

I started with my mother's tan tights and sisters g strings, still love to wear lingerie

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By *tephbicdTV/TS
13 weeks ago

Northamptonshire

Got caught by my partners uncle dressed in panties and stockings at her mums house ..he was doing decorating didn't know was coming round until I saw him in the doorway of the bedroom wanking as I was on the bed stockings suspenders panties short silk nightie on licking a pair of used panties..he stripped off walked over to the bed offering his cock to my mouth and said open up or I will tell ..my first crossdresser experience

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By *othinglikesinMan
13 weeks ago

Dumfries

First time was somewhere around 15/16 and a female friend dared me to wear her pants and tights, will never forget the feeling, opened up a whole new world….

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By *nly1meMan
13 weeks ago

here there n everywhere

"Got caught by my partners uncle dressed in panties and stockings at her mums house ..he was doing decorating didn't know was coming round until I saw him in the doorway of the bedroom wanking as I was on the bed stockings suspenders panties short silk nightie on licking a pair of used panties..he stripped off walked over to the bed offering his cock to my mouth and said open up or I will tell ..my first crossdresser experience "

nice x

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By *umblebiMan
13 weeks ago

ayles

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By *en4funoxonMan
13 weeks ago

Banbury

Those first few steps are amazing and frightening in equal measure. Then you realise you want more height…….

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By *om.stockingsMan
13 weeks ago

mold

Playing dress up and found a pair of tights and have been hooked ever since that day

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By *icki222TV/TS
13 weeks ago

Lincoln

I’ve gone so far down this rabbit hole I’ve given up trying to get out! Let’s be honest girls we don’t want to anyway do we.

The pleasure gleaned from pulling on a pair of FF nylons far outweighs the slightly guilty feeling that we shouldn’t be doing it. Yummy

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By *iss Sophiebelle OP TV/TS
13 weeks ago

Reading

As someone asked - it involved a borrowed pink thong and matching bra, and I was soon showing off online...

Love to chat on this topic one-to-one, If anyone wants to share in private? I'm unshockable

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By *ayk15689Man
13 weeks ago

Wolverhampton

Use to wear sisters stuff in early teens. Bras. Panties. Nighties.

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By *harlotteBrooke9TV/TS
13 weeks ago

Manchester

That’s hot

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By *dstevebiiTV/TS
12 weeks ago

birmingham

Mine was pre aranged after chatting to a guy. He ask me if i would wear hes wifes stuff for him . Best sex ever. Been hooked since

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By *atietvsheffTV/TS
12 weeks ago

Sheffield

Started at an age that is considered an unlucky number, first it was mums tights and stockings, then my sisters when she got to 17/18 and started wearing sexy undies and stockings, after that it was my girlfriends undies and stockings, we married and she often borrowed mine when she had none herself to wear, and then the wife started to not want to be involved when I dressed, she started wearing stockings and suspenders for work and not just evenings out, then the discussion she wanted a divorce as it turned out she had been shagging her boss, 2 months after she told me she was also pregnant and needed the divorce quick and if I objected and didn’t do as she asked which was basically give her everything she would expose me to my family and work mates as a sissy, I complied as I couldn’t take the risk she was bullshitting, so I had £53 in my bank account when I’d remortgaged and given her everything she wanted. Since then I’ve always Bought my own and the wardrobe just keeps expanding, several times I’ve purged when I got divorced or new relationships started and then broke as I couldn’t risk them finding a wardrobe of women’s clothes and heels. Now I’ve stopped purging, too expensive and I know Katie will never disappear as much as I’ve tried over the years when relationships break down because of my desire to be a woman when I need to be. My favourite times are when I femulate my partner, I buy us matching outfits and I mean matching, everything, undies, legwear, heels, dresses, skirts, tops, jewellery, perfume, everything the real woman wants as the outfit I buy 2 of so while she is out and about being a real woman I wait home as the beta female awaiting text messages about what effect the outfit is having on admirers, etc. depending on who she is out with sometimes she shares a taxi home with friends so I have to stay inside others she will be in a taxi on her own, she will text 30 mins of so before and say she harms run out of money for the taxi fare and tells me I have to go out into the village to the cash point and get some money out then walk back to the house and await her pulling up, I am then to walk back down the drive to the taxi, the driver then hears her says “she will pay” motioning outside his cab, he turns his head, looks Katie up and down, opens the window, looks closer says the price, I take my purse out of our matching handbags and pay him. She gets out of the cab and he can now see 2 “women” in exactly the same outfits, the only difference is she is blonde and Katie maybe dark hair, sassy pink wig or blonde highlighted depending on what was required by my partner before she went out., the drivers faces are always a picture, sometimes they get bold and say things like “do you want a real man luv”…..

femulating the real deal wxactky is so horny

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By *iss Sophiebelle OP TV/TS
12 weeks ago

Reading

"Use to wear sisters stuff in early teens. Bras. Panties. Nighties. "

I think a few of us can relate...

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By *ndrea54TV/TS
12 weeks ago

cambridge

Femulating mmmm i like it

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By *dstevebiiTV/TS
12 weeks ago

birmingham

Mine was with a guy who asked me to wear hes wifes stuff . Been dressing ever since and love being dressed

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By *ihullfunMan
12 weeks ago

hull

Mines to naughty to put on here, due to my age at the time

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By *ritneyfearsTV/TS
12 weeks ago

london

Juat my sister's tights and knickers, I owe that girl a lot x

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By *iss Sophiebelle OP TV/TS
11 weeks ago

Reading

Anyone around for roleplay chats about this tonight?

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By *lisonTVsissyTV/TS
11 weeks ago

Torrevieja, Spain

It all began with my Mum's tights, panties and swimming costumes. Then I began collecting from various sources

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By *iM4kinkMan
11 weeks ago

San Antonio

"My first experience was a good few years ago, I decided to dress late one night had collected up a bit of gear from charity shops mini skirt etc and bought some stockings and suspenders in a party shop so got dressed up and went cruising to a known layby with cottage down in Devon, it was about 2 in the morning there were a couple of cars parked up but couldn't see anyone so after a bit went into the cottage for a pee was startled to see someone in there so went into a closet and when I came out he was stood there wanking his cock in clear view he said suck me so I did then another guy came in and started feeling me up in the end there were five guys in there they had me stripped to stockings, suspenders and knee length boots only, ended up in a cock frenzy, spunk everywhere fook knows where they all came from at that time of night when I came out it was 4 o clock lol. The whole situation was crazy really but cock brain had taken over and what still surprises me even to this day is the amount of masculine guys who partake of gurl pleasure even with some of us who are fairly masculine ourselves. "

i would and still do get sooo insanely hard up for dirty, aggressive use from hung Dom men. i've done REALLY FILTHY stuff too and loved it. Scared myself at how fucking filthy i was.

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By *iss Sophiebelle OP TV/TS
10 weeks ago

Reading

"It all began with my Mum's tights, panties and swimming costumes. Then I began collecting from various sources"
LOVED wearing swimming costumes when I started - lots of fun in sexy bikinis

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By *andycd20000TV/TS
10 weeks ago

limerick side of ennis.

My sister had lycra panties and I found them and put them on. I was very young but was hooked then. I used my Mum's too

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By *ony 529Man
10 weeks ago

coventry

I started very young with my mom’s stuff then progressed onto my sisters. This was back in the 70s with camisole sets tanned, Stockings and can’t stop

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By *oodymonsterMan
10 weeks ago

Near Shrewsbury

I started young with my siblings underwear and clothes and on a family holiday I would wear my aunts and cousins.

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By *rinwin69Man
10 weeks ago

STOCKPORT

Started with a mates sisters knickers, saw them and xouldn't resist putting them in my pocket, took them home and slipped into them...hooked ever since!

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By *r_enMan
10 weeks ago

Hartlepool

Started young with family members stuff.

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By *iss Sophiebelle OP TV/TS
9 weeks ago

Reading

So many sexy stories - if you've like a more detailed conversation - I mean really detailed - do message me...

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By *onkoMan
9 weeks ago

here and there

A long time ago in a household far away....

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By *ravellingcdTV/TS
9 weeks ago

Ayrshire

My big sister always wanted a little sister and then I popped out, she would look after me and dress me in her pink frilly dresses to take me for walks outside. My family have loads of pictures of me in her dresses including her school uniform and gym slip. She would do my make up, dress me up as Cinderella and we’d put on pantomime shows for the family at Christmas which was recorded on video.

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By *ndreacdxxxxTV/TS
9 weeks ago

Derby

Mine I have shared on here previously

I had got dressed out 1 night in a services in my car and then stopped at a layby with a public pay phone (long time ago) what happened next was amazing and still excites me nearly 15 years laters

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By *ingeriefetish69TV/TS
9 weeks ago

North East

Mine was caused by my mother and my aunt. Aged 11, I was pushed into an open air swimming pool fully clothed. The only dry clothing was my cousin's tennis dress and a pair of her cotton knickers. I had to put them on and walk to the car, and was shocked to find they felt so nice I was getting hard (I'd been humping my pillow and messing my pyjamas for about a year by then). The hem of the dress against my bare legs was even more exciting. I spent the 15 minute car ride trying not to leak on the dress - it was too late for the knickers. Got back to where we were staying, ran upstairs and got under the covers. My cousin came in to get her dress back, and pulled the covers back to demand her knickers. Her eyes widened when she saw my bulge, and left saying I could keep them. I was a hot, sticky mess 5 minutes later.

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By *nly1meMan
9 weeks ago

here there n everywhere

i’m interested in this good start

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By *ini1275Man
9 weeks ago

stoke on trent

Oh yes

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By *ingeriefetish69TV/TS
9 weeks ago

North East

It's not my thread - that was my first xding experience - I'd need the permission of the OP to describe how I descended further onto trannydom.

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By *ingeriefetish69TV/TS
9 weeks ago

North East

If anyone wants to know more about my journey into depravity, please DM me.

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By *iss Sophiebelle OP TV/TS
8 weeks ago

Reading

Still getting some quite wonderful messages on this topic - very eye-opening! A whole generation who couldn't stay out of their mum's lingerie drawer...

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By *anyaTgirlTV/TS
8 weeks ago

manchester

My sisters guides uniform xx i asked for my own for xmas obviously i didnt get one xx

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By *ony 529Man
8 weeks ago

coventry

"Still getting some quite wonderful messages on this topic - very eye-opening! A whole generation who couldn't stay out of their mum's lingerie drawer..."
. I have to help my hands up to that one

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By *ryton 123TV/TS
8 weeks ago

Chatham

Been occasionally crossdressing for years, it's only very recently iv wanted dress up and play with another man.

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By (user no longer on site)
8 weeks ago

Started with mums and sisters like everyone else , now years later I wear every day and still love it

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By *unand games69Man
8 weeks ago

Cwmbran

Started when an older relative looked after me. He exposed himself to me, he was wearing tights under his trousers.

He made me feel his cock which was my first real sexual experience.

He then made me wear tights. The feeling was immense. I love wearig lingerie and playing with men and women when dressed.

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By *iss Sophiebelle OP TV/TS
7 weeks ago

Reading

Do message me with more details boys - don't be shy!

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By *nly1meMan
7 weeks ago

here there n everywhere

mmm love to grope older in nylon

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By *eresa_cdslutTV/TS
7 weeks ago

Bodmin

I had always thought of myself as straight-then-walking the dog in the woods one day I walked past a parked camper van. A voice from inside asked if I would like a glass of cold white wine. It was a hot summer day and I was thirsty. A transvestite inside put a large full glass in my hand and as I drank she pulled my shorts down and started to suck me! She asked me to fuck her as soon as I was hard. Well I was hooked and the camper van was there every day. She soon had me dressing and meeting her friends and going to parties dressed!

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By *idechickTV/TS
7 weeks ago

here and there ; )

About 13/14 trying my sisters knickers on

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By *tephanieuktvTV/TS
7 weeks ago

bristol

Just pre teen wearing my mums knickers & tights trying to pose like the readers wives in fiesta

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By *lderman500Man
7 weeks ago

sleaford

First time was with a older guy when I was in school he got me to take his trousers off and he was wearing stockings and suspenders no knickers he got me to wank him felt great after this first time I would meet him at his house dress in knickers stockings and suspenders and he would play and fuck me can’t get enough even now xx

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By *hatsthisMan
7 weeks ago

Newcastle

Such an interesting read

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By *vorgoodun84Man
6 weeks ago

shropshire

I started by taking my step moms sexy lingerie, id dress in a matching bra pantie suspender belt an stocking before my dad would take me back to mums, then when at mums a friend an me used to sneak into a barn an dress in these outfits an wabk over each other

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By *ingeriefetish69TV/TS
6 weeks ago

North East

"I started by taking my step moms sexy lingerie, id dress in a matching bra pantie suspender belt an stocking before my dad would take me back to mums, then when at mums a friend an me used to sneak into a barn an dress in these outfits an wabk over each other "

My wank buddy used to dress me in his older sisters undies and school uniform, then wank me off with the hem of the skirt. I'd then tit wank him with the bra (stuffed out with her soiled knickers), and end up with 2 lovely sticky messes all over me.

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By *ednesday 2023TV/TS
6 weeks ago

Stortford

Fiesta and Esc*rt readers wives, happy memories x

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By *llSxy4UTV/TS
6 weeks ago

London & Hastings

It first started with tights & nike pro leggings, now its full feminisation. Oops

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By *usie pTV/TS
6 weeks ago

taunton

Some of these latest confessions are very interesting

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By *iss Sophiebelle OP TV/TS
5 weeks ago

Reading

Agreed Susie! Always open to talk more privately...

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By *ervyOldManMan
5 weeks ago

Here and There

I was a very young age when I went into a family friends house and caught him as his alter ego Rachel.

I had to do a double take as he was very convincing

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By *irm_hand69Man
5 weeks ago

Blackpool

Good looking sissy x

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By *irm_hand69Man
5 weeks ago

Blackpool

Good for you , what you feel inside is matter , I just read your long profile , and looking at all your pics good looking sexy curvy man x

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By (user no longer on site)
5 weeks ago

I was 13, and tried on my mums swimsuit and panties was hooked after that

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By *rive 101Man
5 weeks ago

uxbridge

I started with my mums and a few cousins knickers and panties

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By *edseethruMan
5 weeks ago

douglas

House sitting with my best friend while his parents and sister went to Spain on holiday

Amazing week ! Great memories

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By *iss Sophiebelle OP TV/TS
4 weeks ago

Reading

Sounds good _edseethru. was it mum's or sister's?

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By *laire4490TV/TS
2 weeks ago

northallerton

My first bi experience was in the Scouts .An older boy used to take me into the outside toilets and suck me off. I was dressing in my mothers clothes before I went to school. Would then have a nice wank

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By *hatsthisMan
2 weeks ago

Newcastle

"House sitting with my best friend while his parents and sister went to Spain on holiday

Amazing week ! Great memories "

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By *iss Sophiebelle OP TV/TS
2 weeks ago

Reading

Any more confessions? Don't be shy...

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By *ursendr1Couple
2 weeks ago

worcs

Tried on my mums tights and sexy underwear felt great, then nothing for 25 years

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By *iss Sophiebelle OP TV/TS
1 week ago

Reading

Anyone want to chat about this right now?

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