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The Lighter Side Of Crossdressing

24 Posts
9 Users
74 Reactions
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Posts: 101
Lady
Topic starter
(@justjillian)
Reputable Member     Lancashire, United Kingdom
Joined: 11 months ago

Seeing as being new to this site has energised me and made me feel so less awkward about the joy of dress, I thought I would just do a few positives :-

I grew up in the 70's/80's as a teenager - big deal I hear you say. What I am grateful for though is the happy accident that I am so glad it happened but never of course planned for the event.

The Sixties, Seventies and Eighties was a melting pot for new music/cults ( I started in 76 as a Punk and have a very diverse taste in music because of those times) 

Now the magic bit - it was perfectly acceptable to have you ear pierced and if progressive like me, had both done ( only because the norm was to have your left ear done, but Gary Numan had his in the right ear. So I had both to be hip.

Years later, now that I fully dress - I am always grateful for my piercings - so I do not have to wear clip ons etc and of course being as certain age -  I never get asked why I have 3 holes in the left and one in the right, its accepted that is what you did in those decades. I have also crossed the equator but sadly no one has mentioned that.

Now the next one is that it not always doom and gloom to dress. 

My former partner and I were together for 25 years before we called it a day and still best friends. Dressing was not one of the reasons.

I was 20 and she was 27 when we first met. She had so much more life experience ( even though at 20 I thought I knew it all) . She looked like Linda Evans and on few occasions in the month would surprise me by being hosed and heeled, She said she felt ultra sexy when she did it ( I knew what she was on about - see I did know it all)

Fantastic ! This went on and never got boring, she used to floor me with the way she looked and it was everything I wanted. UNTIL - here we go, yes you guessed it - I told her about my dressing. She was okay and even once did the makeup for me not too bad then? 

What I did notice though, was that I was not the recipient of her surprise alluring sessions anymore. This is when you need to communicate and use the humour that is installed in us as a coping tool. So I asked her why no sexy surprise any more ?

She replied that since I told her, she would think that I would be wishing I would be wearing the gear instead and put her off the whole thing. Now honesty is alway the best way regardless. I replied that when I see her like that, I am very much Hetro and aroused with Jillian being very much asleep (comatose to be exact). She sighed and went oh okay. Not sounding to convinced to be honest. 

This is where I had to use a comparison with humour as to how she made me feel:-

Me - You know I play guitar in a band and gig in bars ?

Her - Yes

Me -  What's my bands name?

Her - Oh I can't remember ( Never could remember, but to be fair did change the name often)

Me - You know who Jimmy Hendrix is ?

Her - Yes of course, love him!

Me - Well, when I am dressed like a woman, I can be compared to an okay guitar player in band that you cannot remember the name of. When YOU are dressed up - you are Jimmy Hendrix and beyond anything I could attain to !

A week later - she's back ! Hosed, Heeled and feeling super sexy again.

Its not always negative 

Jillian x

 

 

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17 Replies
Lady
(@leainvancouver)
Joined: 12 months ago

Prominent Member     Vancouver, British Columbia, Canada
Posts: 373

@justjillian I grew up in the same era when Bowie and many other performers were gender bending and breaking norms. It was a great time! 

I also had partners who would get dolled up in lingerie, heels and stockings and it turned me on to no end. It took me a while until I realized that I wanted to be wearing lingerie, heals and stockings too! Now I do and I love it. 

 

Lea

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@leainvancouver

Thanks for the reply - interesting times indeed. I am the youngest of 7 and have been influenced by the older siblings taste. My first ever LP was “ The rise and fall of Ziggy Stardust” when it first came out, I was about 7 or 8 and still have it. I always was called weird by my friends because when you take records to school, they took singles of Suzi Quattro and other Pop icons. Where I would be bringing in Roxy Music, Bowie and Black Sabbath lps. I still was proud though that my teacher wanted to borrow my Roxy album- I could not say no as it was called “ for your pleasure “ but hope that they were not worried that I was listening to a song on the album “ in every dream home a heartache” ( if you know it you will know what I mean regarding its content).

I have four sisters and although I learned many skills from them of how to treat and talk to girls, often wondered if their influences instilled the urge to dress. I have now of course come to conclusion that it’s not a choice or part of influencing at all. It’s part of my persona and was never a choice and accept my alter ego with more understanding as I get wiser.

it has often been overlooked at the social element of any teenage cult. The best example being the Punk explosion- to us,it did not matter what colour, orientation or even sex you were, as long as you loved the music, we loved you.

I have always said, don’t care what you are, as long as you are happy.

“Do anything you wanna do” - Eddie and the Hot Rods

Jillian xx

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3416

@justjillian I have all Roxy Music, but I don't know what you are referring to regarding that song. I just liked their music, Jillian.

It would be difficult for artists to cover Roxy Music's music, but I have recently heard some amazing covers of the Rolling Stones' "Paint It Black, even Blondie did a fantastic version of "Fragments". Actually made me sit up in my concert seat. All of these covers were very imaginative. RM was imaginative on their own.

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@harriette - it is about a man who has his dream home but only has a blow up doll for love. I am sure if I had kids and they listened to it would have awkward conversations pending.

very overlooked band especially when Brian Eno was a member.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3416

@justjillian Ah, yes, the blow-up doll. I forgot about that. Not quite so bad as some other lyrics that I have heard, though. 😱

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@harriette yes agree there are many but as an eight year old and not even knowing what a blow up doll was ( I grew up in the countryside).

I have been listening to Leonard Cohen since I was a kid. Overlooking the obvious connotations of his lyrics, example “ And now, I hear your master singYou kneel for him to come“ hit me like a train the other day, I know that song word for word and never occurred to me it’s hidden meaning until lately.

life’s rich pageants and always learning eh?

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Lady
(@leainvancouver)
Joined: 12 months ago

Prominent Member     Vancouver, British Columbia, Canada
Posts: 373

@justjillian That was the time when songs started appearing about changing genders of which Bowie was the master. Good times. Music has always carried me through good times and bad times. A friend asked me tonight if I would rather be my age now in the 1970's or today. I immediately said, the music was much better then! And those Roxy Music album covers! 

Lea

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3416

@leainvancouver Yeah, I bought the import versions for the covers. 🫣

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@leainvancouver Yeah the UK covers were far more risqué 

xx

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3416

@justjillian I just listened the music. It was rare for me to delve further into it before the Internet.

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Baroness
(@chrisfp99)
Joined: 2 years ago

Famed Member     London , Kent, United Kingdom
Posts: 1566

Harriette, I play keys in four bands and in my main one we used to do an awesome version of Virginia Plain, sung by the drummer rather than the singer xx.

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Guest
(@Anonymous 94505)
Joined: 11 months ago

Estimable Member
Posts: 225

@justjillian Great times and great music. Oh and that gorgeous girlfriend, I really did want to wear those 80s clothes. Wonderful colours, styles.

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@melaniejames Oh lovely ! They were great times and yes the clothes were fancy indeed. I had longer hair than my girlfriend at the time ( down to my shoulders and highlighted as was the norm for the 82/83’s trendy Male) Fact is we spent more time arguing as to who would get to use the hairdryer first. I would argue that nine would get all frizzy if to done quickly. She used to wear my Levi’s all the time but I don’t think she crossdressed 🙂

 

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Guest
(@Anonymous 94505)
Joined: 11 months ago

Estimable Member
Posts: 225

@justjillian It was a time of blurred genders. I also had longer hair which was useful as buying products was harder then. Later in 80s worked nights and dressed days.

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Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@melaniejames I was still very young and I was a chef which had the split shifts , so dressing was very rare as too many distractions - clubs, girls and drinks to name a few .

One positive from my lady nicking my jeans all the time was I actually wore hers once ( as you say Blurred Gendering ) this is when I found out that I was a size 12 uk - oh those were the days - size 16 now but was very happy when a 14 fitted me the other week - Result x

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Guest
(@Anonymous 94505)
Joined: 11 months ago

Estimable Member
Posts: 225

@justjillian Agree on that many distractions back then.

Love the denim myself and only fair you shared with your girl.

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Ambassador
(@alexina)
Joined: 11 months ago

Famed Member     Fife, United Kingdom
Posts: 1756

@leainvancouver Exactly how I feel when I see an attractive (to me) woman in nice clothes and heels. I am both attracted and jealous!

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Posts: 1983
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Not just words, but actions are important as well. I agree that it is essential to keep an open dialog about out dressing, but more importantly how important our spouses are to is. But, showing them that is just as important. My wife and I have always had great intimate experiences, but besides telling here how sexy she looks "hose and heeled", I make sure to show her incredibly turned-on I get and make sure she is more than satisfied in bed.

She does the same for me when I am :(hose and heeled.")

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1 Reply
Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@jjandme thanks for the reply. Totally agree about projecting of how they make you feel.

the door has always swung both ways in the respect. 
Although I do not see my ex much anymore, I did meet up for a brew with her ( a brew over here is a cup of tea, not beer - sorry if you already know that) she moved away and so met up as I was in the area. We still look each other in the eyes and reciprocated altercations prevail still. So still at ease with her, do not flirt as we are done. But I liked it as we were talking when I said “ you know, sometimes you still take my breath away when you look at me with those Blue eyes”

She replied “ I know”

‘Nuff said. 
Jillian xx

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Posts: 1648
Baroness Annual
(@d44)
Famed Member     New York, United States of America
Joined: 5 years ago

Good story Jillian.

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Posts: 101
Lady
Topic starter
(@justjillian)
Reputable Member     Lancashire, United Kingdom
Joined: 11 months ago

Thank you Fiona, I am just now trying to celebrate my dressing with a touch of humour ( like for example when I said to myself after putting on too much eyeliner - “ at least Dusty Springfield could sing and get way with it “

God knows I beat myself up about it for so many years but now realise that it’s a gift to explore your other self and hey! Love doing it and one of my favourite sayings is :- it’s only kinky if you don’t like it 😀

Jillian xx

 

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Posts: 1831
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Jillian -

Thank you for your story - it was nice to hear how you were able to calm her fears.

XOXO
Suzanne

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1 Reply
Lady
(@justjillian)
Joined: 11 months ago

Reputable Member     Lancashire, United Kingdom
Posts: 101

@cdsue Believe me - the pleasure was all mine - she was my lady after all and all I wanted was for her to happy. Nice to be nice xxx

Jillian x

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