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How i started dressing

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By *1ch1e OP   Man
2 weeks ago

York

In my late teens (18) I found a liking for dressing in women’s underwear, my mums, and used to have some incredibly hot wanking sessions whilst my parents were out of an evening. Id never thought of myself as being gay before as i’d always fancied girls so it was quite a shock to discover i enjoyed using women’s underwear rather than just admiring them in magazines !

It started off when I can across some of my mums stockings in one of the draws. I instantly loved the touch of the sheer nylon against my hands and I’d use one to wank off, being careful not to leak my cum onto them lest she notice. I’d always loved seeing women in stockings whilst flipping through, and wanking off, to the Kay’s home shipping catalogue so I thought I’d try a pair on one evening my mum and dad were at the pub.

The sensation was amazing. I adored the feel as they rolled up my legs and was immediately hard with a raging hard on as I stood naked except for the black stocking in my Mum’s bedroom full length mirror.

After that I found a suspender belt, an old pair of her silk knickers and as soon as I had some alone time in the house, I’d parade around the bedroom admiring myself in the undies until I had unloaded my hot juices!

Things started to get more horny as I used one of her bras, padded out with socks, a slip and then eventually skirts and tight blouses.

Shoes were more difficult as my feet recharger than hers but i did find a pair of heels that i could squeeze into and totterxarounc the empty house in.

Then I started experimenting with nail varnish, painting my toe nails and finger nails bright red which added to my outfit and sexed it up enormously. I’d spend ages carefully painting each nail, blowing and drying then as a real woman would.

Make up came next, I loved the taste of lipstick , smell of powder puff and feel of eyeliner as i stared in the mirror and did my best at glamming my face up . My ears weren’t pierced so I found a pair of gold clip ones and crowning glory was an old long brown wig I found in my mums wardrobe which she hadn’t used for years.

The transformation was amazing to my eyes. I thought I looked the right side of slutty even if my amateurish attempt at make up wasn’t up to much. The really amazing transformation however was in my mind! I felt like a real sissy when I spent the good hour or so getting ready and had strong desires to have sex with a man like a woman would, sucking his cock and being fucked on my back like a really sissy it. I these fantasies he would be a large dominant man who would dress me up and then use me for his pleasure in the back of his car or in his wife’s bed whilst she was out! The orgasams were so intense.

Wanking just wasn’t enough by that point and I wanted to know what it felt like to have a cock deep in me. Not having the guts, wherewithal or knowledge to find this imaginary lover, I started penetrating myself with carrots and candies, using shaving foam as lube and fantasising that I was on my back , my liver with a large belly pinning me down, a hand around my throat and a long hard cock pounding my ass.

Of course as soon as I’d climaxed and the lust drained from me, I’d have to go through the laborious process of tidying up, putting all the clothes and underwear and jewellery back so it wouldn’t be missed and then start with the nail polish remover and make up wipes to transform myself back into a teenage boy before they came in the door.

i’d get so exited on the days they were out and as soon as they had left the house i’d be grabbing my outfit and applying my make up and using my makeshift toys!

Remarkabley my psrebts were blissfully unaware of my fetish although I did have one close call when they came home early and i was still in the process of cleaning up. Fortunately they stayed down stairs and i pretended i was doing homework in my room. I still had my wig, undies and make up on and if they came in my room i would have been caught red handed or more accurately with my pants down which wouldn’t have been easy to stomach in an irish catholic family! i managed to replace everything in my parents bedroom and clean myself up before they came up. phew. I had however forgot to replace the knickers which i’d accidentally kicked under my bed in the scramble and which my mum questioned me about a few days later after she found them whilst cleaning my room. I just swore I didn’t know and thought maybe they had fallen out of the washing basket. A lame excuse but my mother seemed to buy it and would never have dreamed her lovely son was a latent sissy slut who loved to cross dress and taste cock.

I had no illusions that I was in anyway convincing or that I could get away with dressing and venturing out in public in search of sex back then. I did occasional wear knickers and hold up black sheer stockings under my jeans on nights out, to the ignorance of my friends, but didn’t get to use them in earnest with an older men despite hoping i might one night get seduced on my way home from the city by some sleazy character after a submissive slut.

This carried on for about a year then girls came on the scene and I parked my dressing in favour of more conventional heterosexual relationships. Occasionally though I did wear my girlfriends knickers without their knowledge. I guess once you open that box it’s hard to close fully!

I did eventually get the opportunity to dress for an older guy who fulfilled those late adolescent fantasies by treating me like a real sissy slut in his hotel room a few years later when I rediscovered my CD urges and the joys of submissive gay sex.

happy and exciting days

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By *ita99TV/TS
2 weeks ago

bognor

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By *nchsolentMan
2 weeks ago

Fareham

I was told to dress in what was provided

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By *vsindyTV/TS
2 weeks ago

A place where sheep are warm, or Burnley.

Ahhhhh, the illicit thrill of wearing someone else's lingerie and stockings....such a buzz.

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By *harlotte39cdTV/TS
2 weeks ago

rochester

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By *rc.186Man
2 weeks ago

GRANTHAM

I started very much the same way

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By *ylonplesureTV/TS
2 weeks ago

Stone (staffs)

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By *ichelle999TV/TS
2 weeks ago

colchester

My dressing started at 12yrs old with my sisters party dresses oh god the feeling mmmmmm xx

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By *erriTV/TS
2 weeks ago

Hastings St Leonards

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By *esley 60TV/TS
2 weeks ago

PERTH

I started by wearing my mums aswell

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By *ibby BrownTV/TS
2 weeks ago

cannock

I started at an early age wearing my grans panties and tan tights, also my mom's sexy stockings and undies, up until I could afford to buy my own

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By *regABCMan
2 weeks ago

blackhall

Never done it but open to a guy trying to dress me up

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By *ampell1Man
2 weeks ago

Liverpool

Started with my sisters auntys in my teens

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By *ubkinkarineMan
2 weeks ago

southampton

Brings back the horny lovely memories of slipping into mum's hot lingerie and admiring myself in the mirror especially how good and big my cock looked in her panties

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By *erry55Man
2 weeks ago

Portlaoise

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By *cotssissyTV/TS
2 weeks ago

falkirk

Surely most of us started that way. And as you said, once tasted it’s impossible to go back. So many purges, so many purchases

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By *arriedbidad2020Man
2 weeks ago

Grays

have tried it once in her stockings and suspenders for another dad

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By *illgossardTV/TS
2 weeks ago

Abergavenny

Oh yes please.. I've been enjoying ladies clothing for my whole life.

Of course the focus starts to move on to what you do with the woman you create.

And so we search for a lover.....

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By *mberflameTV/TS
2 weeks ago

Birmingham

Practically identical to how I started. XxX

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By *Paul200Man
2 weeks ago

Kelso


"My dressing started at 12yrs old with my sisters party dresses oh god the feeling mmmmmm xx"

I was the same, I had 3 sisters so plenty of choices

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By *ashtoolMan
2 weeks ago

belfast

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By *oe trinityMan
2 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 wanting to get caught dressed n helpless on the floor

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By *oxy 11Man
2 weeks ago

Doncaster

I started at 12 with mums and sisters

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By *issyswichTV/TS
2 weeks ago

Gateshead

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