Crossdressin fantasies

[phili]

I have too many to count- but I'll go with walking the waterfront boardwalk on a sunny Sunday afternoon in a light summer dress and heels. I am sure I am going to fulfill this one! I'm sort of worried I don't feel ashamed, scared,- just anticipating how much fun it will be and how long I have wished I could do it.

I also fantasize that I will have a friend with me and we'll be chatting away, and stop and talk with others, and people will be happy because I'm happy... oops- well that's where this qualifies as a fantasy- although when I did go to my ceramics teachers' open house in my white lace dress she gave me a really warm hug- twice! The warmth of those hugs meant a lot to me.

[Jeanettew]

Mine is pretty simple i want a total make over

[Nadia Wren]

I like Evie82's Classical period fantasy.
Lately, I've fantasized about having my portrait painted by an art student. Actually both, in drab and en femme. Then sending the femme portrait to a thrift store far way and having them try and sell it. I'd keep the drab one for my family, but the though of people wondering about the femme portrait would be funny.

[Lydianne]

Thanks, Shirley! I appreciate it. I wanted to see which way you would take it. The ultimate serial culinary disaster- and getting disgusted about it- fantasy. I approve! .

- I was kind of hoping that maybe the other three would have blamed you and turned against you .
- Maybe they would have ambushed you, thrown you overboard and abandoned you; leaving your clothing, shoes, and make up ruined .
- Maybe a particular pirate ship might have been in the area .
- Maybe the madame captain would have taken you aboard, given you some magical new clothes, new shoes, and a total make over .
- Maybe you would have joined them and embarked upon a mission of exacting law & order upon the high seas in high heels .
- Maybe you might have paid a visit to a certain small, four-man vessel and food-stained crew with which you might have been earlier acquainted .
- Maybe said crew would have seen you, felt envious, and pleaded to join you .
- Maybe you would have accepted; maybe you would have respectfully declined...

Maybe in the director's cut edition .

( btw, more space for food on a pirate ship ).
Cheers, Shirley!

[Tania75]

My fantasy increases with how likely that it actually will happen. In my younger fashionable years, I went to the hairdressers and got all sorts of treatments, colors, and curls, and went to the beauty salon for a mani/pedi and facial, and in both cases, I'm sure the ladies secretively pushed me to see how far I would go.
At the end of the day, I would be cut, colored and curled, with painted toenails, tinted eyelashes and shaped eyebrows, but somehow at the end of the day, just looked like a guy with a fashion sense, such was how good the young ladies were.
My fantasy was, that given that I shared a house with two ladies at the time, they would carry on the theme, and dress me in their clothing and fuss all over me.

[leotard fan]

i have lots of fantasies. for exemple: next week i will buy a tinker bell costume...

[Abbey11]

When I was younger I wanted to be Rupaul, still do, love her style .... And success

[DIANEF]

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.

Oh yes, I know that now but back in the day it really appealed to me. Now I wouldn't even consider doing it. I think the outfits were the main thing, I also liked nurses uniforms (proper 70s-80s style) but that's another job that many could not put up with.

[Lily Catherine]

Many of what I considered fantasies are plausible with sufficient preparation, training and in a few cases money. Here're some that wouldn't be.

Prerequisite: living full time (an actual possibility unlike the below situations)
- Being married in church, in the presence of my immediate family, as the bride. Enough said.
- Being baptised as Lily

Prerequisite: reliving the past (truly impossible like eating the sun)
- Reliving my entire life having been born female
- Failing which, attend my school prom, voluntarily, presenting as female.

[Julia Welch]

A three or four-some while dressed with hot GGs ... I've done it as a male, but would love to try it enfemme ...

[ShirleyN]

A three or four-some while dressed with hot GGs ... I've done it as a male, but would love to try it enfemme ...

yeah. I have something similar to this. which is the ultimate schoolgirl fantasy and having a three-some with two of my female teachers both naturally in long skirts.

[sweetdreams]

Common theme would be being forced to do it by someones intent or by circumstance.

Earliest fantasy was when I was about 9 or 10. I fantasized about somehow ending up in a remote girls boarding school. I would perform various chores but I was pretty much the only male there. As time went on it seemed so much more practical for me to just start wearing the same clothes as the girls.

Now it's similar. Tied up and dressed like a girl. Forced to be a maid.

A real life story that spun my propeller was when I stumbled across Andrej Pejic. Andrej was a male model originally from Bosnia and his family emigrated to Australia when he was about 8. He was always fairly feminine in mannerisms and dress. He became a male model when he was 17. Somehow, someone thought it would be an idea to put him in a dress. He looked gorgeous as a girl. I was so envious. He also modeled lingerie including bras. Here's this guy getting paid big bucks to cross dress and strut down catwalks not to mention working alongside all of the female models. Not too surprising Andrej is/has transitioned to Andreja around 2014. Damn it if he wasn't living my fantasy and making a lot of money doing it.....

[Evie82]

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'll join that band! Shame you've called bass already, but guitar and keys on offer :-)

[Scarlett398]

Mine is dressing up as Scarlett just like the photo in my profile picture with my wife wearing a similar outfit and then go to bed (both of us fully dressed) and make love for about three or four hours working around our clothes without taking anything off while making love! Just keep workin' around the clothes while trying everything we've ever done in our bedroom while making love over all the years we've been married!....Thanks for reading my post and that was a really great idea for discussion!..Scarlett

[Kandi Robbins]

I have the fantasy that I walk into a bar, sit down and am treated just like any other customer. Oops, never mind....done that!

Ok, ok, I have a fantasy that I am trying on wedding dresses with other future brides around and conversing with them and their families....darn it, done that!

My real fantasy is taking a beauty class with a bunch of women and no one treats me any differently.....oh yeah, that did happen a few times.

Seriously, I have the fantasy that everyone on this forum that wants to go out, to be themselves, gets the courage to do so. I've been blessed with the courage to do whatever I want. Go out ladies!!

[ShirleyN]

"Thanks, Shirley! I appreciate it. I wanted to see which way you would take it. The ultimate serial culinary disaster- and getting disgusted about it- fantasy. I approve!."

Great!. Glad you like it! Have to admit, I would never have thought of the whole concept of a pirate ship. I'd be thinking more along the lines of a coastguard lifeboat, captained by a crew of four other women, who would rescue the four damsels in distress; one of whom would be (in the fantasy) my partner, a GG.
"I was kind of hoping that maybe the other three would have blamed you and turned against you.": Well, we HAVE gotten ourselves into a awful, embarrassing mess, haven't we? Personally, I think Audrey would possibly be blamed the most as it was her who arranged to whole trip and insisted that we all wear long skirts (her own personal fetish).
For my part, I'd be the one who'd have to do all the washing and ironing in this case, something I wouldn't actually mind doing!
To be honest, the whole point for me was to just get to the point of where our clothes get stained and ruined and then our reactions to it.
"Maybe you might have paid a visit to a certain small, four-man vessel and food-stained crew with which you might have been earlier acquainted.": Not entirely sure what you mean by this, though I think I understand.
My two favourite parts are:
"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!!""
I like this because I can almost see that frown of disgust on Karen's face as she looks at the mess on herself.

"Then, we all stand up together very slowly and carefully examine ourselves. We all look at each other and frown in disgust at this."
This is probably the most interesting image for me as, even though you can see the four women doing this, I really don't exactly know why I like it. I also think that each of us would have, a smiliar, yet slightly different reaction. e.g. Karen might lean slightly over the table, I might examine my sleeve, Adrienne may put her hand up to her shoulder to examine the egg stains and Audrey would probably hold the ends of her top and look down at the large red wine stain on her top.

"Maybe in the director's cut edition:" Deffinately. I DO plan on writing a full-length version of this story if you're interested, so I'll let you know when it's done.
Again, many thanks!

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Another crossdressing fantasy which I keep constantly having involves me and two of my female friends, bursting out of our long skirts in a she-hulk like way. I love the whole idea of the material ripping and the three of us giggling like naughty girls. Sexy!!

[Lily Catherine]

I'll join that band! Shame you've called bass already, but guitar and keys on offer :-)

Seeing you've called all of that, I guess I'll play the drums. Heh.

[Christina D]

Well, usually it's easiest to meet at the drummer's house. What time works for you, Lily?

[DIANEF]

On a musical note (see what I did there....)I had a a fantasy of being fully dressed and out in some club, and getting up on stage to belt out some rocky number, Nightwish or Within Temptation style. I do have a half decent singing voice and can hit quite a high note if I try.

[Leslie Mary S]

Fantasies? I have a few. First and foremost is to have a body that will fit into a dress size 2. I am tired with this size @ 20.
To be accepted as a world class photographer and fine Artist. (a possibility, but time is running out).
To do a guest on stage with RuPaul.
To truly know who "ME" is.
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Actually I am mainly left-handed but on occasion I have painted right-handed. This was shot in my small bedroom

[XemmaX]

i have always loved the idea of being a dominatrix. being in command of a dungeon sounds do much fun.

[Lily Catherine]

Well, usually it's easiest to meet at the drummer's house. What time works for you, Lily?

Unless you don't mind me playing on a crude set of electronic drums, and you don't mind having limited breathing space, I'd prefer to meet at a rehearsal studio with equipment rental.

On a musical note (see what I did there....)I had a a fantasy of being fully dressed and out in some club, and getting up on stage to belt out some rocky number, Nightwish or Within Temptation style.

I do this all the time when driving, except not dressed. I think it'd be a bit dissonant were I dressed (doubly so since this is Within Temptation we're discussing here...)

[CynthiaD]

I'd like to go to the opera at all of the world's great opera houses dressed to the nines. (En femme of course.)

I'm gonna do that.

"Pretty soon."

[Swimtran]

My fantasy is to become a woman, be it magically, surgically, or miraculously.

[Contessa]

Mine would definitely think I would be thinking to far into fantasy land. I would like to do a role on Law and Order:SVU. But I don't want to be the criminal I want to be a full time cop about to retire since I am so old. And they need me to catch up with a perp. Some how I just want to be important for some part of the 44 minutes of the show. When it was over I would want them to ask me to come back if they ever needed me again. That would just be a fantasy to meet Mariska and do something good again. I would wear a beige skirt suit w/ a white blouse some where the show. I can see me running down the street in a pair of heels and catchling up to the perp and taking him down. Then I would make a comment about putting a hole in my hose and suit.

The ending would be my girlfriend would be the lawyer for the defense and we would leave together even though she had just loss the case.