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
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
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
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
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!
More Articles by Mona
- Proud to be a Goodwill Girl
- My Season of Doubt and Shame Part 2
- My Season of Doubt and Shame: Part 1
- Media Review: Casa Susanna
- Mona Says Yes to the Dress


Latest posts by Mona (see all)
- Proud to be a Goodwill Girl - October 24, 2021
- My Season of Doubt and Shame Part 2 - January 24, 2021
- My Season of Doubt and Shame: Part 1 - November 21, 2020
- Media Review: Casa Susanna - November 8, 2019
- A Hilarious Look at the Challenges Most Crossdressers Will Face - April 12, 2019
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
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! ❤
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!
Zsazsa
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
Thank you, Rachel – so happy to hear that you enjoyed the article and that it resonates with you. I had a lot of fun writing it.
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
Thank you Susan – glad to hear you enjoyed it.
Wow, Mona!!! LOL with your poem full of truth and good sense of humor. Thanks for sharing with us.
So glad you enjoyed it, Anna. I had a lot of fun writing it.
Although it was 3 years ago, that Mona wrote this verse
It still rings true in every line and things often get worse
Very good, Smartina. And yes indeed, it can and does get worse…it is a steep learning curve for sure.