By Mona

A light-hearted look at the trials and tribulations of learning to cross dress based in large part on my first-hand experiences (and maybe yours too?)

Just sit right back and enjoy this tale

of men who love to dress

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Most started at a tender age

but why is anyone’s guess


For many it’s a troubled route

spent battling the urge

The lovely clothes we’ve all thrown out

in cycles of binge and purge


Panties, bras and silky slips

how we love the feel of them

Even under drab men’s clothes,

a girl can still feel femme


But lacey satin lingerie

is not made to fit most guys

At online stores we agonize

did we order the right size?


Our butts and hips we must enhance

with pads made of soft gel

We wear enough damn padding

to play in the NFL


When nature calls you will recall

there’s a man bit you must free

But when you’re wearing pantyhose

do you stand or sit to pee?


Cross dressing is laborious

so many things to learn

The work is not so easy

girl’s passing must be earned


Necklaces are nice to wear

but we cuss to beat the band

While grappling with those tiny clasps

made for so much smaller hands


Garter straps that don’t stay tight

and zippers that won’t slide

And blouses with small buttons

that fasten on the wrong side


With lipstick and eyeliner

every girl must find her own way

We aspire to be Beyoncé

but will settle for Doris Day


Overdo your lips or eyes

and you’ll come to see real soon

That you look much like The Joker

or a very ill racoon


Most girls brush on mascara

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to emphasize each lash

But touch that black goo to your face

and your look goes in the trash


False lashes are the devil’s work

and you will scream and cry

When you glue the third one in a row

to the middle of your eye


Once your makeup is perfected

‘cause you haven’t used too much

You’ll want to don a pretty wig

as the final crowning touch


Just be sure that rug is good and snug

or in horror you will shout

When it takes flight in a gust of wind

As you’re strolling out and about


In stockings, tights or pantyhose

how we love to show some thigh

Sliding up our just shaved legs

we shiver and feel high


But jagged nails on hands or feet

will quickly spoil the fun

When that pricey pair of sheer thigh highs

is ruined by a run


Let’s flaunt our legs in a tight miniskirt

the girl inside will cry

Like a pricey runway model

she wants to catch your eye


Yes, those models in their lingerie

are so proud to strut their stuff

But a hairy back in a bustier

is a sight that’s pretty rough


Then there’s very pretty dresses

how we love to wear them all

From simple frocks to evening gowns

for wearing to the ball


But be sure a dress can stretch enough

to accommodate your frame

‘Cause twisted limbs and cries of pain

are best left to a rugby game

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Once you’ve finally squeezed into that dress

you’ve lost more than an hour

And you’re sweating so profusely

That it’s time for another shower


Yes, it takes many hours to perfect your look

then of course it never fails

You look down at your hands and see

that you’ve lost three press on nails


Lady’s shoes are not like men’s

there’s such a vast array

From platform pumps to Mary Jane’s

it’s hard to find your way


But every girl soon comes to know

when shopping at the mall

Why worry about the choosing

go ahead and buy them all!


There’s thigh-high boots and strappy heels

and stilettos to the sky

To walk in them is quite a feat

for the average stocky guy


You’ve got to learn to take small steps

and be careful not to sway

If you hit the ground you may hear the sound

of an ambulance on its way


A corset is great for achieving the shape

of a woman instead of an ape

Just take a deep breath and suck in your gut

‘til your mouth goes all agape


It will deliver an hourglass figure

some curves that will help you sashay

But lace it too tight and for breath you’ll fight

and your face turns blue by the ending of the day


Who knew brassieres were so complex

they mystify most newbies

Seems you’ve got to have a PhD

to choose the right pair of boobies

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A really nice set of voluptuous breasts

is surely the ultimate prize

But too many girls think that bigger is better

and choose an outlandish cup size


Oh the rolls of tape that have been used

for some cleavage to create

But after ripping off that sticky stuff

the pain will take days to abate


So, let’s hear it for us guys who dress

though so many don’t know why

At least we can relate to the girl on date

who hopes to impress her guy


There’s so many ways we can stumble

and I’ve come to see at last

A girl has to strive to come fully alive

so that one day she will pass


To end this tale of angst and woe

let me state without a smirk

That becoming the woman of your dreams

takes a lot of damn hard work!

Alright Girls, now it’s your turn! Please use your own creativity and write us a funny stanza that would perfectly fit into this hilarious poem! We are looking forward to your responses!

 Or Girls, pick the one stanza from this poem which directly hit home to you and may have reminded you of a funny short story you would love to share with us!

 Thank you for reading this poem and possibly providing us with a funny response of your own……..Sincerely, Mona

Please go all of the way to the bottom of this page to leave your clever and entertaining responses! Thank you!


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On-and-off CDing since early teens. Long stretches without any urges but here in my advanced middle age Mona has emerged in force. She's a high-spirited gal who shall no longer be denied. It's both thrilling and a bit intimidating because I don't know where she's planning to take me. Although I only get to dress every now and then, I'm having great fun and just enjoying the ride. I'm happy to have found this welcoming and supportive community and hope to get more involved as time allows.
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Christine V
Christine V
3 years ago

I loved your article and I envy the pretty girl in the picture who’s standing in front of the closet in that pretty dress

Martina Rae
3 years ago

This poem is wonderful! Funny, clever and so true! I know many of us have shared lots of these experiences. I’m going to have to study it for a few days so it can fully sink in. Hopefully I can come up with a stanza of my own to contribute.
Thanks Mona and thanks to everyone else that may have contributed!

Geraldine Mac
Active Member
2 years ago

Loved the poem. How about this little add on:

Dressed up, makeup on, wig now steady,
just need a necklace and I’ll be ready.
But can’t work the clasp, need a closer look,
to see if it’s a lobster or a fishhook.
Or is it a push, toggle or spring ring,
or a box, barrel or bayonet?
I wish it was a magnet!


Rachel Briony Shropton

I agree with Christine. Lovely article which is so right and I do envy the pretty girl in the picture. Wonderful words. Thank you. Love Rachel X

Susan Talbot
Active Member
1 year ago

Mona thank you it’s such a beautiful poem. Ooh I am so jealous of the pretty girl standing in front of her closet. If only to be young again. Susan

1 year ago

Wow, Mona!!!    LOL with your poem full of truth and good sense of humor. Thanks for sharing with us. 

Active Member
1 year ago

Although it was 3 years ago, that Mona wrote this verse
It still rings true in every line and things often get worse

Would love your thoughts, please comment.x
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