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The Lighter side of Crossdressing Pt2

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

So, we have all a story regarding the issues with acceptance form SO/OH's. 

I have two more (Hopefully) amusing tales regarding my Current and Former SO ( don't worry, no more after this)

Latter first :- So if you have read my previous post, I was with my still lovely lady for 25 years. She knew that I dressed but did not really get involved, that said - she was cool with it or at least tolerated.

Anyway, there were 4 of us couples who decide to go for the weekend at a holiday camp where they had expired 80's bands playing. One of the lads said " Hey we should dress as women" My heart jumped but I never said anything but everyone else said " Great idea, what a laugh". Before you knew it, the girls had already decided of who would do the makeup, wigs, shoes and clothing. Suprise to me they all agreed on the slutty look. I tried not to be too enthusiastic but my gosh - I could not wait and was light in the head with excitement.

So comes the night, dressed to the nines, the girls made a great job at making us passable and I am out as a woman finally ( although unofficially, being not Jillian). I was on cloud nine all night and it was great to feel such a way but tried so hard as to not show how much of a buzz the night was.

The only problem was deciding which rest rooms to use AND we still had to go to the bar all the time as well !

So much for equality eh?  

My current SO had never been to Thailand, I have been lucky enough to have travelled to many places around the globe and suggested that she would love it ( she did ) 

So we are in Koh Samui and of course shopping for her "Genuine Fake" Handbags, we had doing this all night and she was getting good at bartering - so this could take some time.

She sees some more bags in a shop, I said I will wait outside and people watch for a bit. Along come four lovely dressed Lady boys, they say hello and stop to chat. Not sure if they are plying thier trade or not - perhaps just chilling. Anyway they find out which Football team I support and we are all on the street just talking sport. She comes out of the shop and says "what's this?"

I say in my usual joking manner "Its not what it looks like" she laughs out loud and gets the phone out and instruct us all to line up for a photo. Great photo, big smiles. An hour later she has updated her Twitter status with the hilarious post "I leave him for 5 minutes and this is what he gets up to" 

So she was all in for me hanging around with the ( let it be said NOBLE ) ladyboys. When it comes to accepting my trying some clothes on and making a mess of my makeup - she's not that sure.

Of course the mistake we make is thinking we are all thinking the same thing. Little steps though xxx

Jillian xx

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3 Replies
Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@justjillian I wonder why your friend said, “Hey, we should dress as women” just to go to a concert….?? Maybe he…

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@chanel Hi Chanel.

Maybe He - does dress and if he does well good luck to him as I know what you tend to go through.

No - it was not just a concert, its was a weekender at a typical British holiday camp ( likened sometimes to a Cold War Iron Curtain Gulag but hey, fun is where you find it .

So got there on the Friday - had a dance and then on Saturday night - Had a dress on ! Nice slinky Blue number, my lady did the makeup and so I could not really ask one of the other girls if I could keep the dress as that would have let the cat out of the bag 🙂

All items were donated to charity shops.

 

Thanks for the reply

Love Jillian 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@justjillian ohhh, I thought maybe he had the same thoughts…😀

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Posts: 3245
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 4 years ago

Great story. I have had those moments in the past when the opportunity to dress comes along, especially dressed looking very much a girl. I understand that feeling too.

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@ab123 Yes, its nice to share and know that someone actually understands how one feels.

Thanks for that x

 

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Posts: 3797
Lady
(@harriette)
Illustrious Member     Toronto, Ontario, Canada
Joined: 2 years ago

I would like to have more pleasant interactions with people when dressed. I have had a few with a couple of sales clerks, but they are gone, now. I related my rather unpleasant NYE interaction with somebody who had been drinking, but because I dress subtly, it is either too subtle to get noticed or nothing except stares happen at all. 

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

Estimable Member
Posts: 101

@harriette

Yes - I read you post about the time on the bus. Thats beer for you, thats why I gave up drinking years ago because I realised that I was indeed nowhere near the Funniest, best looking, best dancing, toughest guy in my town LOL………….. 

You did the right thing and its always best to ignore as best you can

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Posts: 827
Baroness
(@river)
Noble Member     New Hampshire, United States of America
Joined: 1 year ago

Great story please dont stop writing them. I was at a Halloween party and one of my friends wives suggested we all do a gender swap party. I got very excited but then The idea was shut down 🙁 bummer ah well .  I wish I saw more CDs out there or maybe I just dont notice.  Cheers RC

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

Estimable Member
Posts: 101

@river Oh I would have been gutted if they had pulled the plug on the idea. One of the lads did have his doubts about being beaten up in the Rest Rooms ( it was rougher in the 80’s/ early 90’s) but we soon calmed his fears by saying “well don't mess about in there then!"

Thanks for liking my stories, they are true and never had the chance to share them. 

Keep your eyes peeled for part 3……..

Love 

Jillian xx

 

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