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The Lighter Side of Crossdressing - C'est tout !

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Posts: 101
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Topic starter
(@Anonymous 94145)
Estimable Member
Joined: 1 year ago

“Puss In Boots” what’s it about? - I do not or never want to know. The following will explain why.

We all ask the question of when was the first time one ventured to wearing ladies items.

Mine is from an innocent “game” of Puss In boots with my older sister. We did not know what we would do as part of the charade but it meant one of us using some sort of prop. The prop was a pair of my mums boots - quite long Black and in Suede - just the job ! Too small for my sister - but fitted me. I was to be the main character. 

I put them on and instantly felt a surge of euphoria, I was trembling and felt like I had an electric shock. I am 7 or 8 years old and of course not understanding the “Awakening” thought it just was thrill of having the lead role. We played for a while with little direction as we both did not know the story. 

I so enjoyed wearing the ladies item, in hindsight now know why and never have forgotten the feeling of my first fix.

I never want to actually read or watch the Puss in Boots story as it would not hold a candle to the thrill of my own version of the tale. I still do not own a pair of Boots.

 

The next occasion was not so euphoric but funny nonetheless……..

There is  a very popular comedy entitled “Father Ted”.

It tells of the trails and tribulations of two Catholic Priests “Exiled” to a small Irish island. This springs to mind as I was thinking of an episode that always makes me laugh. Sadly I cannot remember the exact episode - I would bet on it being called “The Mainland” - forgive me if I am wrong though….

Set the scene :- Two older ladies are having a gentile afternoon tea in a small typical tea shop.

The conversation would border on gossip and the such.

One of the ladies said “ Did you hear about Mr” ( cannot recall the name) ?

Second Lady “ No what’s happened?”

First Lady “ He has been burgled again !”

Second “ Oh No! Not again, is he alright?”

First “ Oh yes he is grand - they did not take anything but they forced him to dress as a woman and when the Police arrived they said this is the forth time that he has been a victim of “Forced Transvestism !”

 

Forced Indeed and know the feeling

My Parents were keen Caravaners in the seventies. This involved having great adventures in a home from home 50 or so miles away from where we lived! 

The Caravan was embarrassing as my mum had placed giant Disney characters on the sides - Therefore “ Pimping her ride” ( In her mind at least).

Myself being a hip 9 year old who was into Bowie, Roxy Music and realising that after the Puss in Boots episode, also liked to take a walk on the wild side! 

I was therefore repulsed by the conformity of such a cheerful socially accepted decoration.

As part of the great adventure, we would “Wild Caravan” which sounds salubrious but sadly meant parking up in a lay by overnight on a busy dual carriageway that would usually have a view of a Petro Chemical plant nearby.

It was a home from home and after a very sunny English day. Mum decides to do a wash and in that commanding way of saying they had, said “get them off, they need washing”. Compliance was assured and off they were. She washes all of my smalls for me and puts them out on the washing line contraption that someone would have been proud to invent and we all went to bed in our aluminium home.

Now then, English weather, often discussed and never predictable. It rained all night after such a lovely day and my smalls were not going get get dry soon.

So no smalls then !  Mum has always got the answer though:- “ You will have to wear a pair of your sisters panties” -( It must be said that dressing then was still a lightly treaded path and was furthest from my mind in this situation ). 

She holds up a pair and commands “ Put these On” ( Compliance assured again )

My sister protests as to the the possible contamination of the male but is quickly placated with an offer of a new pair. 

They were the frilliest panties I had every seen, in a cream shade. They looked awful and felt even worse when worn. They were itchy and felt wrong on me - so not a pleasing experience and certainly not to be included in my ever pleasant cross dress memories.

Great, feel weird and uncomfortable. 

In the same lay by, another adventurous caravan is parked behind. As was the norm, we all congregated with total strangers and swapped tales of their adventures and what wonderful Petro Chemical plants they have parked near in their travels and of course the weather !

Mum pipes up with “ Oh the rain was terrible last night and soaked all the washing I had on the line  - He ( points at me ) has got a pair of his sisters knickers on as all of his undies are wet!” Oh the shame of it ! The other owners two kids were giggling ( as I would have).

My world comes down all around me at such a personal announcement. I drop my head and make my way back to our caravan in a walk that is akin to an ending of the Incredible Hulk TV show. 

I start to sob and alike to a Buddhist chant, do that mumble that kids do and a bubble forms on my nostril.

My mum comes over to tell me to stop being such a girl ( she started it!) and stop sulking.

She explained that its only clothes and that they don’t know you anyway.

 

Funny of how that is still relevant !

They were still really itchy though …………

Jillian XX

 

 

 

 

 

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10 Replies
4 Replies
Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4019

@justjillian Moms are great, eh? 🥰

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette Oh yes, always dropping you in it haha

 

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Lady
(@leainvancouver)
Joined: 1 year ago

Prominent Member     Vancouver, British Columbia, Canada
Posts: 379

@justjillian we should all have been so lucky to have a mom like yours that not only encouraged your wearing of dainty panties but seemed to think nothing of it! My mother was more into shaming us for doing anything considered out of our place. I had two brothers and would have loved to have had an older sister who could have taken me under her wing. 

Lea

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@leainvancouver - Well she had raised 4 girls and 3 boys - me being the baby of the family. So by the time she got to me I guess she would have seen it all.

Having 4 sisters certainly taught me a lot.

Jillian xx

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Posts: 3446
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

I was also in a large family with three sisters and a brother and crossdressing was a taboo. It was quite a cacophony getting everyone ready for school. I was about five and in the melee mum in a fluster put one of my sisters school blouses on me, my whimpered protest fell on deaf ears as she topped it with a jumper and said no one will notice and no one did. I was lucky to have had sisters as we did play dress up and no one minded.

On another occasion I was entering a Carnival fancy dress and was going as a Roman soldier. I had the armour but mum and dad were trying to figure the 'skirt', mum produced a red dress. They tried to fold the top down around my waist but it wouldn't sit so mum said I'd have to wear it as a dress with the armour over it. Did I mind? Not at all as I paraded along. A couple of boys exclaimed to all what I was wearing but I didn't care, I was loving it, well when in Rome...

I wonder what my family would have said if they found out there was secret dressing up too. 

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1 Reply
Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@ab123 I like the cacophony of the morning school rush - I can indeed relate to the “It’ll have to do” remark that was oft said by my mum. It must have been like hearding cats.

The Roman soldier was a great idea - this Is why I alluded to the “Forced Dressing” accidents 

Thanks for reading

Jillian XX

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Posts: 379
Lady
(@leainvancouver)
Prominent Member     Vancouver, British Columbia, Canada
Joined: 1 year ago

What lovely stories of your mothers! You were blessed to have such wonderful female role models around you.

Great story telling too! Thank you for sharing these delightful anecdotes. 

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1 Reply
Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@leainvancouver 

Thanks for reading them, I am sure you can understand that it is the first time I have been able to share such things without the fear of someone looking sideways at me.

Jillian XX

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Posts: 3446
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

If someone hasn't given you the sideways look Jillian you haven't lived!

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1 Reply
Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@ab123 Ha - yeah 😌

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