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Thread: Crossdressin fantasies

  1. #1
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    Crossdressin fantasies

    I know that this has probably be mentioned before, but am just curious to know do any of you have a fantasy when crossdressed and if so, what is it? I have this fantasy about being dressed as a office secretary/receptionist in a long skirt outfit (i.e. black jacket, white shirt and a long black skirt (either pencil skirt or any other long skirt, black tights and boots.) working for a female boss.

  2. #2
    Pirate Queen wannabe Maria Blackwood's Avatar
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    I have a couple, but one would violate decorum, I think.

    The other one is just fanciful silliness about being a pirate queen.

    IMG_0916.JPG
    Behold Captain Maria- fashionable and fabulous scourge of the high seas.

    My crew and I would sack the artificial floating cities that these billionaire Silicon Valley geeks are always going on about building because they just can't stand living amongst us mere mortals who don't devote our lives to the vital national interests of chat and photo sharing apps with stupid names.

  3. #3
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    True to my name, I love horses and equestrianism. My fantasy would be to wear a ladies 1890 era riding habit with hat and veil and riding sidesaddle on a big horse, on a fox hunt or something similar. Lots of pics online showing this style. Other fantasy would be to squeeeze into a tight mermaid dress and show off.

  4. #4
    Platinum Member Beverley Sims's Avatar
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    When walking down the Boulevard in Hollywood my mind wanders and I would like to look like some of the impersonators that frequent themselves outside Graumman's and other spots along the walk. Some of them are done up well.
    Work on your elegance,
    and beauty will follow.

  5. #5
    Pirate Queen wannabe Maria Blackwood's Avatar
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    Quote Originally Posted by equestrifemme View Post
    True to my name, I love horses and equestrianism.
    I like the cut of your jib, stout hunting lady, and the mermaid thing could be used to distract enemies. I need crew for my pirate ship. Can you handle a cutlass?
    Last edited by Lorileah; 01-27-2017 at 01:19 PM. Reason: you didn't need the whole quote to reply

  6. #6
    Member Periwinkle's Avatar
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    Mine is probably a bit silly... But when I was a kid, I used to want to be like Cardcaptor Sakura. She was a magical girl from a TV show I absolutely loved. Not only did she have magic powers, but she also had a best friend who was constantly making her new pretty costumes to wear! She wore something different in every episode. As lame as it sounds, I've always wanted to be in her shoes; going on magical adventures and wearing cute new outfits.

    She's probably the reason I'm as into clothing as I am, because I remember my love of crossdressing really spiked when I discovered the show in fourth grade. I just kept trying to find outfits I thought she would wear on her adventures.

    My sense of style has broadened since then, and I feel like I have a much less fanciful style now. But even now, very occasionally I'll still see something and think, "This is totally something Sakura would wear," and I won't be able to pass it up. It seems that even as an adult, I can't completely let go of that old childhood dream.

  7. #7
    Pirate Queen wannabe Maria Blackwood's Avatar
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    Fantasy should be silly sometimes. You can come have magic adventure on my pirate ship.

    Seriously, I saw Cardcaptor. She could sink any Spanish frigate that tried to get all up in our business. Yeah, they laughed in the taverns of Portobello when I said I was hiring a sorceress. They're not laughing now! The treasure fleet awaits.
    Last edited by Maria Blackwood; 01-27-2017 at 12:35 PM.

  8. #8
    Isn't Life Grand? AllieSF's Avatar
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    One of mine was to be on stage for the first time as that super popular woman singer who shows herself for the very first time to her fans, and more importantly to her family and friends. I know that this one is a very big fantasy because I cannot sing!

  9. #9
    Gold Member NicoleScott's Avatar
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    Some of your pirate fantasies should be rated "AARRRGGHH".
    Hope I spelled that right.

  10. #10
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    Another one i Have, and this may sound more than a little bit silly, but I also have this thing about being on a boating trip with four other female friends. All of us in long skirts and short sleeved tops. We all sit down together to have our lunch and the our boat is suddenly hit by rough waves. The boat rolls about and our food goes all over us, completely ruining our beautiful skirts. All four of us then stand up together, disgusted at this.

    [SIZE=1]- - - Updated - - -[/SIZE]

    Aye Cap'in

  11. #11
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    Mine is simple: to be totally accepted by my dear wife. We are getting ready for bed and undressing. I'm sitting on the edge of the bed and about to remove my bra when she says "let me unhook you"; she unhooks my bra, I take it off, slip on my nightgown, and off we go to blissful sleep in each others' arms. Nothing could make me feel more accepted than that. Alas it will likely remain, forever, a fantasy.

  12. #12
    -1.#QNaN Lydianne's Avatar
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    @Shirley:

    So all four of you stand up, disgusted . . .

    *ahem* . . . . and?!?? Are you just gonna leave that story there?!?? . That's gotta be against the rules, Shirley, surely! I need more! .


    @Nicole:
    Haha! .

  13. #13
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    I go to dance classes with the wife. So quite simply instead of me having to lead, she does and I am dressed accordingly.

  14. #14
    Aspiring Member Joyce Swindell's Avatar
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    It's funny how our fantasies change as we grow older. Mine now is simply to spend my life dressing as I feel like dressing that day without any concern or worry over my presentation. This is truly a fantasy in every day life but I may be able to take a week vacation and accomplish this one. Which would be pretty kool too!

  15. #15
    Pirate Queen wannabe Maria Blackwood's Avatar
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    For those of you on the fence, just know my all CD crew gets the snazziest uniforms in all the seven seas.

    IMG_0918.JPG

    We kidnapped Karl Lagerfeld and forced him to design them under threat of bad taste.

  16. #16
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    Must be interesting having fantasies.

  17. #17
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    yes it certainly can be alright!

  18. #18
    Member Evie82's Avatar
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    One of them I've touched on in another thread - being a Viennese opera diva like in the movie Amadeus. Those dresses and costumes are to die for! Plus the general elegance of the period and the wonderful music makes that one of my favourite fantasies

    My other big fantasy is my wedding day... more specifically the one my partner and I want to have the right way round! I can spend far too long looking at bridal gowns! *sigh!* One day :-)

  19. #19
    Stop that, it's silly.... DIANEF's Avatar
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    When in my late teens and early twenties I wanted to be an 'air hostess', jetting off to glamorous places around the world and living the high life. Loved the outfits of course but the life style was also so appealing.
    Here today, gone tomorrow....

  20. #20
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    I had an accepting girlfriend years ago. Used to let me wear her clothes and sometimes bought me underwear. Never had sex while dressed though, and she never saw me with wig and makeup. I would simply love it if we could have sex while fully en femme. Strangely enough I never have the same fantasy about my wife.

  21. #21
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    No of course not. Wouldn't you be? And YES, there IS indeed more to this. Okay then no problem. So, here's how it unfolds: As I said, me and three of my friends, Karen (Blonde), Adrienne (Red Hair) and Audrey (Brunette) are all on a weekend sailing trip down at the local sailing marina.
    Our boat is a small enclosed cabin-cruiser with just barely enough room for all four of us to sit together.
    Audrey and I sit opposite Karen and Adrienne. Just above Adrienne's head is a cupboard with broken door. We're all dressed in long skirts and long-sleeved tops.
    Our dinner is the dirtiest, messiest, greasiest dinner that one can think of.
    Everything goes well and we're all really happy. That is, until, we all gather for dinner.
    We have just finished pouring four glasses of red wine and are about to drink it, when a heavy swell suddenly occurs.
    We all watch with consternation as our plates and dishes start sliding about on the table.
    Karen gasps suddenly as one of the deserts slides off the table and into her lap, splattering cream and custard all over her skirt. She lets out a slight moan and looks up to Audrey as if to say, "Ohhh!!"
    Audrey and Adrienne, however, both grin at her.
    The boat rolls again.
    I notices the pepper pot sliding towards the edge of the table. I reach out to try and grab it but end up putting the sleeve of my top into the half-eaten susages, eggs and chips dinner; the rest of which lands into my own skirt leaving a big dark stain on it.
    Audrey frowns as our arms hit and she ends up spilling her glass of red wine all down her front.
    Adrienne laughs and points at the three of us but stops when the cupboard door above her suddenly swings open and four eggs go flying out of it towards her.
    She closes her eyes and frowns as they land on her left shoulder with a squelch. She looks down at her shoulder as egg yoke trickles down her top and into her own skirt.

    After a few minutes we all take a deep breath. Then, we all stand up together very slowly and carefully examine ourselves. We all look at each other and frown in disgust at this."

    There you are. It's a bit long I know so appologies for that. The whole point of this is that we get our clothes absolutely filthy and dirty. Getting dirty is pretty much the theme of this story.

    Is there anything else you'd like to see with this.

  22. #22
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    My fantasies are usually about some of my actual life opportunities to crossdress. In my real life I always turned down any invitations to crossdress, but in my fantasies I imagine what if....

    For instance, my first real job was in an office where I was the only male. Even my boss was a female. There was one girl my age who never wore a dress to work. One of the older ladies was encouraging her to wear a dress to look more professional. Her response was, "I'll wear a dress to work when Confucius does". This brought laughter and as they considered this proposal. I said something like, "our boss would fire me for causing a disruption at work". Just then our boss (she was listening outside the door) walks in and says she wouldn't fire me, and she thought it was a good idea. This caused more laughter and several others in the office encouraged me to take up the challenge. Unfortunately I made up a couple excuses and the office dropped the challenge. In my fantasies I imagine what would have happened if I accepted the challenge. I would let the ladies give me a full make-over and I imagine the jokes and fun we would have at work.

  23. #23
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    DianeF I had a neighbor who was an air hostess and from what she said it was just a job and not all that glamorous.
    Long hours short layovers of only 8 hours so no time to hit the town just enough time to get dinner clean up then sleep 4 hours then get ready to go again.
    They had to be back at the plane 2 hours prior to scheduled departure time.
    Her main route was Cincinnati Ohio to San Fransisco then San Fransisco to Hong Kong China.
    She made $1,500 a week but never had time to enjoy the money which was pretty much my life being a truck driver.
    Always on the road over 100 hours a week.

  24. #24
    Crossdresser-At-Large BillieAnneJean's Avatar
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    My fantasy is that I can do this and look like a woman when I go OUT enfemme. I know I am fooling myself. I wish I was more believable. But I do my best and have fun. So that works for me.

  25. #25
    SJW and Proud of It! Christina D's Avatar
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    Depending on what I'm wearing, I sometimes fantasize about being in a riot grrrl band, probably playing bass guitar. I've always loved 90s riot grrrl rock (especially Sleater-Kinney, Hole, and Chicago's own Veruca Salt). I actually do play bass as well as regular guitar, keyboards, and sing (though I've never sung in my female voice), so I guess I COULD make it a reality...if I wasn't so bad at being in bands. :-x
    "I'm just a girl, what's my destiny?/What I've succumbed to is making me numb/Oh I'm just a girl, my apologies/What I've become is so burdensome/Oh I'm just a girl, lucky me/Twiddle-dum there's no comparison" - "Just a Girl" by No Doubt

    "The unexamined life is not worth living" - Socrates

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