Tag: crossdressing

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An Unexpected Guest

Another Fantasy of Mine…

I'm wearing my polka dot dress, stockings, suspenders, boots. Tidying the house and general day to day stuff. I hear a knock at the door, so go to answer it. The man at the door is broad shouldered, maybe 6ft, jeans, long coat to his knees, looking d…

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The leaving party

What should have been a night out with my friend turned into my first gang bang…

It had been several weeks since I'd been expertly fucked by Steven, my friend and I kept up our regular meetings although I desperately wanted another night with him, especially after what he did to me, and remembering how dominant he was which I rea…

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A Day in the Garden

Summer. On my knees the garden, wearing white blouse, backless leather skirt, no underwear, stockings, and thighboots. Busy weeding, arse bare to the sun with the skirt having no back of course. I hear footsteps approaching but continue working. The …

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Finally my sissy dreams are realized

My friend seizes his opportunity to sissify me…

After that memorable night with my friend I tried to process it, I wasn't gay? I did have a girlfriend. I didn't fancy men but a man dressed in sexy slips and nighties and dresses, well they definitely caught my eye and I did enjoy that unexpected ni…

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Accidental Anal

An unexpected night for me…

Although this happened a long time ago I'll never forget my first experience so I'll write this as best as I can remember, I hope it invokes memories of your first experiences.This happened unexpectedly when after a night out on the town with my long…

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You're the Wife Now!

A message from an older house wife who wanted me to be her replacement in more ways than one...…

This is not a story as such. It is a message request I received from a lady from this site who is part of a couple. Ever since I received it, it has become my biggest fantasy.I had been on a different swinging website for a few months and found the e…

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First Time Fucked as a Crossdresser Part 2.

Or how I became a crossdressing cockwhore…

My friend says "this is 'Jack', a workmate. Told me he fancied trying some MMM fun and it's your birthday soon. 2 birds, 1 stone". Jack looks at me and said "You never told me he was a xdresser". Mate replied "I just found out". Jack undressed, he ha…

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First Time Fucked as a Crossdresser

When I was 30 I went to a Rocky Horror show with a friend. She wanted me dressed as Frank so loaned me a basque, stockings, suspenders and thighboots. It felt very odd being out like that. After the show we went back to the hotel and I fucked her sti…

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Dressed up and used

Cinema visit..…

Finally decided it was time to visit cinema dressed up,knowing it would be dark but also a thrill knowing I was out dressed like a slut.Dressed in a short pencil skirt,black hold ups,sheer blouse and bra,with blonde hair cascading down my shoulders,I…

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Crossdressing at the charity shop…Pt1

Crossdressed pleasure…

It had been sometime since I had been out shopping for let’s say fetish items.. dressed underneath my trousers in satin and nylons I made my way to the side street charity shop.On entering just one other person present and the shop assistant… I made …

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Crossdressing

Dressed up in the changing room…

On a shopping trip recently I decided to pop into the local charity shop.Just one other looking around and an assistant behind the counter,I browsed and slowly made my way to the womenswear section,flicking through the skirts I came across an extreme…

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Coming out to Trishas Friend

Being used by two women…

I sat on the edge of the couch, my legs covered in shiny, tan tights. White wilk thong and matching bra, black high heels shoes and a lovely white silk thigh length dress a friend of Trishas had bought it as a gift for my girlfriend. Trisha was my g…

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Sissy gets fucked

This morning, Sissy got up to see a note from Mistress stuck to her chastity cage bag saying “Put this on Sissy, we are going to have a dressing up day today and then we are going to fuck” Excited, Sissy put her cage on straight away, looking forward…

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A journey of transformation. Part 1

I was frequenting gay dating sites for many years now, but it was only a curiosity of mine, to see other men naked and read stories about their encounters. I began returning more and more often, absorbed by gay fantasies, to the point I imagined m…

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Sissy Slut for Gordon

Sissy Chrissy gets back on cock after a long time off it.…

I sat eagerly awaiting the arrival of my new friend, the Nero Coffee shop in Ashford was busy and nearly every table was occupied. We had been exchanging messages and spoken on the phone over the past two weeks. Gordon had suggested we…

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It all went wrong

Girlfriend found out about Amy…

So I was led through to Saffi's bedroom naked by her mother, Amy explained that Saffi had a boyfriend but he couldn't make her come in bed, he had mainly watched porn to learn his sexual technique and thought that being aggressive in bed, choking her…

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Why I cross dress and what I'd like to do

My bi fantasy…

So the reason I crossdress is simple. I love the look and feel of womens underwear. I'm under no illusion that I look good in it but that doesn't matter. I do it for me, not anyone else. I like to wear hold ups and thongs or g-strings and no trousers…

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My first experience with a cross dresser

I looked through the toilet door his pants were around his ankles he was wearing black stockings…

My story goes back a bit when we all could have fun in cottage toilets , exciting cock fun , I have sucked been sucked and wanked off so many times , plus I have watched the action wanking off.My story is the first time I had fun with a cross dresser…

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Dogging and Crossdressing in the woods

Caught dogging with a sexy voyeur.…

I arranged to meet a busty young lady for some, outside, sexy fun. Her online profile caught my attention, especially the photos showing off her big boobs covered in cum. A friend had told her of a dogging spot not far from Derby at Woodlands Roa…

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Don’t talk in your sleep

it’s a bloody good job that the wife has no idea what my dreams involve, that was the initial inspiration behind this fantasy story, hope you enjoy.…

I woke to find my wife Sophie staring at me in a really odd way.“Wow! What was that all about”? She asked“What was what all about”? I asked totally confused by her question “Your dream!”“What on Earth are you talking about”?“You were blatantly e…

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Crossdressing in the dark pt 3

Satin and nylons…

My knees were red once master had finished with me,i stood up wobbling after being used my jaw ached,good girl another load in your tummy..i looked up and licked my lips..yes master i replied. I started to remove my clothes and gather them up,leave t…

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Crossdressing in the dark pt 2

Satin and nylons…

...I felt vulnerable but willing as he guided me into the bathroom,he turned the shower on,in you get he said,i hesitated,now he instructed,i stepped in the water soaking my blouse through,my skirt clung to my nylons and the water penetrated everythi…

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Gate guard sucking and undies fun with my sergeant

He sent me some hot porn , normal and bi - I wanked myself silly…

I am currently in the Army , i am single but i have always been bi curious , ive had a little play here and there but nothing to full scratch my itch . That all changed over the christmas period last year , i was on a week long security / gate guar…

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Crossdressing in the dark

Satin and nylons…

Having got friendly with a crossdresser over time exchanging chat he asked if i wanted to meet one evening at his home,the thought excited me,knowing we both had the same fetish.I was late leaving due to work,i had packed my case with my slutty cloth…

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Gardner at night

Risque…

This was outside a travel lodge with a Gardener I was travelling overnight, so I drove dressed in the evening, parked at Hopwood services M42 and changed about 8pm parked up at the back, I stripped completely off, then pulled on my tan stockings, 8 …

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First Time Crossdressing

Where it all started…

I have been meaning to write this for a while but never got round to it This is my first crossdressing experience and I promise it is totally true. Back in 1988 when I was just a young lad of 18, my college had a rag week and a fancy-dress day. My be…

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Beginnings 4

The missing fourth instalment…

I arrived home and after supper went to my room, the bag of lingerie was lying on my bed. I removed the black lace and silk garments and examined them. Black stockings with a garter belt, matching lace panties and a silk slip. I picked up the panties…

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Beginnings 7

A continuation of my voyage of discovery…

The previous episodes are available to read from my profile…. Enjoy I virtually ran home after work that night. I didn’t have much time before I was to meet Patrick as we had arranged. I quickly showered and went into my bedroom to dress. The bag co…

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SW Crossdresser Adventures Pt2

Layby Double Dose…

Back in the summer of 2019 I'd been desperate to get out and have one of my early Sunday morning dressing sessions. I'm talking up at 5am, wash and makeup, dress up, pop some male clothes over the top and take my large handbag with wig, heels, additi…

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First Time Anal while Crossdressing

A true event…

I wrote this about 20 years ago and thought it could do with a rewrite to add some missing details. I had to pick up my touring caravan from the site in the highlands after leaving it for my pal to use. I left work early and drove up. When I arrived…

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