A Hilarious Look at the Challenges Most Crossdressers Will Face

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!

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• Bio
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Mona

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.

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

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