sissy truck driver. Cross Dressing

night work…

Before my retirement I was a long distance lorry driver,, The image expected is of a masculine,strong person,I was physically strong to do the job but very weak emotionally,I have always been a closeted gay,Having two seperate lives as it were,although my fem side would sometimes show,Once my days work was done i would for a layby,picnic area known for gay cruising,One gets to know them over the years,My cab was large and well fitted out. I alway… Read more

First crossdresser Cross Dressing

Not what you would expect in a tight white dress.…

When I was in my twenties we used to go to a club in Soho called Madame Jo Jo’s. The first time I went I thought the waitresses looked so tall and glamorous. I was with a lovely long haired girl and we had swapped jeans as she liked the rips in mine. Hers were indigo and I liked them and as she was very tall so they fitted fine. We were dancing and I felt someone touch my bum. I looked round and it was a petite blonde girl in a tight white dres… Read more

More than one thing rises Cross Dressing

Baking bread with my boyfriend…

Last Tuesday I went to visit my boyfriend, Ray. I manage to visit about once a fortnight. He very much enjoys a "lady with a bit extra"!

For this visit, he had asked me to show him how to make bread, as his previous attempt had not been special. The great thing about baking bread is that there are long periods between stages when you have to find something else to do.
I arrived about 10:30 and spent half an hour douching, doing my makeup and… Read more

Sissy in pretty polly tights. Cross Dressing

Cock in the Park.…

In my 20's l use to love going to a certain park in huddersfield where there was lots and lots of cock action.
Not just during the day but also at night. I loved to wear my sheer pretty polly pantyhose and a pair of silky pantys under my jeans.
I use to love the glory holes, sucking on cocks of all sizes and getting plenty of lovely hot spunk in my eager sissy mouth. I use to wear a bit of lippy to...while sucking a hard cock my own little siss… Read more

Sequel Caught by my Sister in Law. Cross Dressing

Confused disappointed. Part…

I answered the phone Hi Mary trying to sound confident and relaxed but my knees where trembling and my heart thumping wildly. I thought she knows what I have been up to. But no she told me she was coming home for a month in ten days time and she had a surprise for me. My mind racing. Confused as to if I wanted her home or not.
My mind going back to the conservation park in St Helens. The threat of the two men expecting me to turn up next week.… Read more

Bi the way Cross Dressing

Emptying my load…

So I’d finally tried the bi side
Sucking Dom’s 10” cock with some assistance from Katie
By now Katie was escorting after a guy she met via swinging had encouraged her to join a site
She was getting plenty of cock
We still swung but less frequently and we’d met a couple of bi guys
If she had a client that fancied trying his bi side
I’d get to join in
But I’d still never had a guy all to myself
One who wanted to suck as w… Read more

Full turnaround Cross Dressing

It's strange the way things turn out !…

I'm 61 years old now with a beautiful 18 year old crossdressing lover. His name is Simon ( or Simone ) . Slim with very little body hair. He lives with his parents but comes to visit me 3 times a week. I buy his clothes. His underwear. He has a boyfriend the same age as him . Am I being used or am I using him ? I don't know. All I know is that it works for all of us.
This is a story in itself but not the one I want to tell now.
I find it stran… Read more

Sharing Big Ron. Cross Dressing

If only !!…

I has a feeling my ex was cheating on me if, l encouraged her enough as l knew my little sissy dick was useless to her !! She wouldn't admit to it though so l just use to fantasize about her getting fucked by a Big Cock.
If she'd have admitted to it and told me about Big Ron well l would have begged her to bring him home so we could have shared his massive 10"..
Oh l would have loved to have sucked, wanked.licked, worshipped that Big beauty...b… Read more

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My 19 year old female Lodger's Dirty Washing Cross Dressing

The day I got caught with her used undies!…

I have a female lodger who is aged 19. She has been at my place about 3 months.
She is pretty and fresh faced, but carrying a few extra pounds, she is size 18-20.
As I was in ‘male mode’ I told her about my transvestism from the start, even when she came to first view my house. Being a modern student - she explained that she is not perturbed by it and is very open minded.
We got on really well from the start, and she saw me dressed up aft… Read more

Never assume your alone in the woods Cross Dressing

Caught…

I thought I would share this memory from years ago.....

I used to drive to/from work past a piece of common land, wooded with trees, shrubs and a few clearings. Nowadays its become known as a meeting spot but years ago in my youth, it was quiet, especially early mornings. I would often stop and adventure in the woods.

I used to dare myself to strip off and walk naked in the woods, gradually getting further from where I left my clothes. Ver… Read more

Hotel meet as a closet crossdresser Cross Dressing

Crossdresser agrees challenging but fullfilling encounter with a stranger…

Late spring and early morning Spanish sunshine heralded the start of a new and promising day.

As the online radio played memorable tunes from a while back and so provided welcome listening, I wondered what the new day might bring.

When I opened up my mailbox there as usual were the protracted conversations from those who are full of desire though still uncertain about meeting, requests for just one more image from picture collectors and all… Read more

A day in the country Cross Dressing

A new experience…

It had been some time since my last encounter and I had since purchased a nice red basque which improve my figure no end. I was keen to wear it and show it off so I went online and browsed the ads. One particular one caught my attention, it was as a guy who said he was straight, was looking for anal or a BJ and had a 11" cock.

Up until now the largest cock I had ridden was 10" so I was eager to break my record so contacted him to see if he wou… Read more

foursome Cross Dressing

lingerie…

im gaz, 54 and a bi crosser dresser, i love meeting guys and c/d , ive met the same gay guy quite a few times, and last week he texted me to say he had a couple of friends coming to stay and would i like to play, we arranged for the saturday night at 9 o’clock, i showered and put on matching red lace and satin, bra, suspenders and panties,black stockings and leather micro mini, under my clothes, it took 20 mins to drive to kevs house, he opene… Read more

All grown up - part 2 Cross Dressing

A weekend of discovery…

After tasting my cum on Trina’s lips we had a breather and a drink before she took me upstairs to her mothers room.
I laid on the bed looking at the tight leather clad arse of Trina as she rummaged through the drawers in the wardrobe. I asked her what she was doing and she said she was finding me something to wear and as everything she had would be too small she thought she’d find something of her mums.
Jean, her mum had always been on my… Read more

Once a Month Annabella Cross Dressing

fact or fiction will let you decide…

Once

Once a Month Annabella
Annabelle gorged hungriy on the cock in front of her, she had face time to thank for this, shock at the time, but many happy endings now.
As she opened wide to engorge fully she chuckled at the red lipstick clinging to the end, “better wipe that off before you go home darling “, “wipe it yourself slut” came the gruff reply, must admit she loved dirty talk as she sucked harder, and took all of her man insi… Read more

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All grown up - part 1 Cross Dressing

A weekend of discovery…

My wife and I had lived next to Jean and her son Ian for about 10 years.
Jean had become friends with my wife and we saw her often, but not enough to be annoying. We hadnt seen much of Ian in the last few years as he was at uni, and to be honest we never saw much anyway. Quiet lad who spent most of his time in front of a computer.
Anyway, Jean and my wife had booked an evening away to see a London show leaving me at home for most of the weeke… Read more

two crossdresser Cross Dressing

a meet with bev…

I awoke early thinking of meeting Bev and what to wear. I shaved trying to get as smooth as possible and started to get dressed. I slipped on my white basque and slowly rolled on my black stockings with a red top on them clasping them on to my basque. this was followed by a pair of white knickers, short white mini and black top. Once i put my heels on I was ready and waiting anticipating how things would go. Soon the text messages starting com… Read more

Neighbour secret is now my pleasure Cross Dressing

Neighbours secret passion lead me astray…

Having just read "my neighbour shares the same hobby" I am eager to share what happened to me last Easter.My wife Joan and our next door neighbour Carole went away for a girly spa weekend in London leaving Colin and myself much to our own resources. He suggested I came round on the Saturday for lunch and to crack open his latest batch of homebrew.
Over lunch and good few glasses of drink he asked what I normally did when the wife was away, I sa… Read more

What Should I Do Cross Dressing

Meeting but should I dress?…

I am a happily married guy who has cross dressed in private all my life, my wife (Sue) is an elegant sophisticated lady dresses like mother of the bride to go to the shops.

We live quite a affluent lifestyle and enjoy travelling the UK. I have been a member here for many years always joining the crossdressing chat rooms some cuckolding rooms, I am not at all bi.

For the past 4 years I have regularly chatted with another guy my age in much t… Read more

Sequel Caught by my Sister in Law. Cross Dressing

Confused disappointed.…

It was almost ten months since Mary caught me dressed and forced me to stay dressed as a woman or leave her house humiliated and publicly known as a sissy crossdresser.
I had imagined every scenario you could imagine mostly having some sort of sex with Mary
Absolutely nothing happened she just checked I was dressed personally or by security cameras she had installed.
I had not been able to meet anyone and only rarely able to release my frustra… Read more

This Sissy misses Humiliation... Cross Dressing

Just Memories now !!…

In the end my ex left me for Big Ron..l mean you cant blame her.. he has a lovely 10" to satisfy her compared to my sad little sissy dick...but l do miss being dominated and humiliated so much.
Tears running down my face as she puts me in a girdle, or suspender belt..then rolling nylons up my legs...my sissy cock rock hard n wet as she calls me a " pathetic sissy with a useless little cock " reminding me how much she loves Big Cocks..l use to t… Read more

Is this the real life is this just fantasy Cross Dressing

It’s just a fantasy story…

I was on holiday in the West Country last year with my wife Julie and we decided one day to take a walk in the woods close to our hotel. We wandered for a while sticking mostly to the bridlepath though occasionally risking the muddy paths worn by more serious walkers. I was busy taking photos of flora and fauna (hobby of mine). To be honest I hadn’t taken much notice of what Julie was doing, she’d wandered on ahead of me along one of the mudd… Read more

Humiliated in my pink suspender belt. Cross Dressing

Sissy in pink.…

My ex bought me a lovely pink suspeneder belt on line which had a pouch for my little sissy cock..
She would put it on me while giggling away and then fasten my gorgeous chocolate ff nylons ( re _ inforced heel )to it all the time reminding me what a useless little dick l had.
Then putting lippy on me and tieing a neck scarfe around my neck she would laugh even more as my cock was aroused and leaking plenty of pre cum in the little pouch.
She … Read more

My neighbour has the same hobby as me Cross Dressing

Secret CD'ing is spotted over the hedge…

Well, how lucky can I get. My next-door neighbour has the same interest as me, I’ve just found out.

Been a hot few days leading up to the long holiday weekend and like most people, I’ve been out in the garden, planting and tidying & trying to catch a bit of sun. I do love my garden & being quite secluded at the end of a close, I can get out the back and virtually everywhere is not overlooked, except a little bit by next door from an upsta… Read more

A trip on the moors Cross Dressing

The next chapter…

I experienced excitement when dressed in womens clothes and felt very sexy. Somedays I would dress as a respectable woman and others I wanted to act like a whore. Certain times of the year the feelings grew stronger and I just had to meet others although the risk of being exposed was real it excited me too. It was the beginning of Summer and I felt so horny in the hot weather I decided to make contact with someone online and arrange a meet on the… Read more

My journey begins with Master T Cross Dressing

A sub bi guy gets owned in the office…

Master T is a guy I’m looking at meeting soon so this will have to go in fiction for now, but any advice on whether I should meet up with him and what should happen when I do. Any thoughts would be much appreciated....

I’d been chatting to Master T for a while who was married to a gorgeous Nubian princess. He enjoyed watching his wife enjoy herself and she had enjoyed the company of well endowed bulls over the years. Master T was submissi… Read more

Dressed for the Occasion Cross Dressing

Crossdressing…

On Friday, I had a very important meeting with my Manager and an outside agency. For such occasions, I love to wear some sexy underwear; its such a massive turn on and keeps me concentrating (maybe not always on the meeting) lol.

One of the secretaries (Clare) is aware of what I like to do, it’s a long story how she found out, I might tell it sometime.

For the meeting I went shopping for some new underwear, as normal I ended up in M & S. … Read more

My inner self Cross Dressing

The day I discovered a new me…

When I was younger my best man returned for a visit from Australia so his sister decided to throw a welcome party. As we hadn't seen him for some years we decided to surprise him by me dressing up as a woman to see if he recognised me. I was roughly the same height and build as Vanessa so she looked in her wardrobe for a sexy dress and lingerie and a lovely blonde wig. She and her other sister spent an hour giving me a face over and when finished… Read more

Crossing the line - self realisation Cross Dressing

Embracing a desire…

She was out, shopping, I think. It is not important. What is important was that I was at home. Alone. Unfair temptation, I think. Her top drawer was not closed properly; something was stopping it, something black and lacy hanging out. I recognised a pair of her panties. Black, lace front, satin rear. I remembered when they caressed her curves. I remembered the rough lace on my tongue, the aroma and taste of her excitement.

It was unfair to ex… Read more

End of Year Crossdressing Cross Dressing

Dressed for a day…

Last evening I had the opportunity to get dressed, Sue had gone with a friend to London for a dinner and theatre trip left at 3 not expected home till nearly midnight.
So I planned the day to be a girlie day had a leisurliy bath with the wet shaver to really remove every last body hair. Smooth all over , cleaned every nook and crevasse, borrowed Sue’s body lotion and slipped my chinos and f shirt on, and waited for Sue to leave the mornin… Read more

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