From late March through the end of September it’s Australian Rules football season and of course it happily coincides with the cooler months that allows for Caty to emerge in “all her glory.” To repeat what a wise old CD once said, “Crossdressing is a winter sport.” My SO and her sisters grew up as, and still are devoted supporters of one of the teams in the comp and when the fixture came out earlier this year, oh joy oh joy, the above lovely ladies decided on a weekend away to watch a game about 100k’s out of Melbourne.

This of course meant Caty could book a makeover and a go shopping day. My regular makeup artist is away working on a stage show, so I ended up with a lovely lady in Melbourne’s southern suburbs named Meg. Quite by coincidence, the charity I work with is also based in that area, and I am a frequent overnight guest at a block of self-contained apartments down there.

My beloved knows but does not want to know about Caty, so in order for the above to work, I always have to revert to the guilty as sin “pack of lies” about what I’m doing whilst I am away. I hate doing it, but what is the alternative? So thus, with the usual spin, I found myself all set up in the apartment on Friday afternoon, ready for the makeover on Saturday morning.

Visit Transgender Heaven

Of course, once the “do not disturb” goes on the door it’s time to get my gurl on. I was soon into my lingerie for the afternoon and for the evening meal. A relaxing meal then early to bed in nice warm comfy pj’s and sleeping braless, which of course is one of my favorite femme pastimes.

Up early Saturday, check that I have everything and check again. Underdressed, and in my favorite bra with everything but forms attached, it was a 15 minute drive to the artists home with suitcase in tow. Walk in her front gate as the male me; walk out 90mins later as Caty. It was probably the longest time I’ve ever spent being made over, and this was all due to the fact she only had natural colour false nails, and I needed three coats of polish on them. Such pampering as a lady “does your nails” for you!

Here I mention again, that in order to get the false nails off easily, I use the little double sided sticky pads first, then the nail glue, followed with the nail. Meaning, that when taking them off you are just pushing them off the sticky pad, otherwise you have big strife dealing with the glue!!

So all made up and dressed, it was time for photos in the back yard. I was very happy with my outfit, especially since I’ve never tried wearing a scarf before. For some reason, some of the photos came out a bit blurred, but over all I was happy with my editing. My expanded male tummy caused problems with my skirt falling, but safety pins helped there. Somewhere under all that frippery and finery is a bald “more than 3 score and ten” male!!… And ain’t that half the fun of it all!!

En Femme Discover Woman Within

OK, out the door, into my car, and on the phone to see if I could still make my appointment for a femme bra fitting at Lisa’s Lacies in Seaford, Melbourne. This was to be my shopping highlight of the weekend, but I was running late from the makeover. Unfortunately, no bra fitting so it was off to the shopping centres. For some reason, my suspender belt and stockings would not stay in the correct position, so in both centres it was just a quick walk up and down while window shopping.

In Kmart I had a really nice Caty moment. A woman came around a corner and just about knocked me over. She backed off and said “sorry dear.” In that brief moment I must have looked like her granny!

Saturdays being very busy times in these places meant long walks from the car park, with a blister on one of my toes to prove it. But hey, I’ve worn those clumpy heels before without a problem!!

Those of you like me, who go out driving in gurl mode, will agree that the feelings of your arms against your own breasts as your drive, and holding the steering wheel in the correct 10 to 2 position, with lovely pink nails in your line of vision, are special times indeed—not so in drab!

So it’s time to head “back to the ranch.” My keycard to allow me to park would not work, so the receptionist comes out with her card to let me in—Caty sits there in all her glory! I wonder if this made the Shift Report that night, and frankly I don’t care if it did! I’m a good “regular” there, and I am neither the first or last CD that has ever stayed there.

Exceptional Voice

I enjoyed another night of a pleasant meal and more very good Australian Chardonnay. By this time, I’m not only thinking female but feeling it, too. Thoughts such as, “I feel like I have breasts all the time” go through my head. Sunday and check out time comes all too soon. But before then, it’s again one of my favorite femme pastimes. Yes, I know it’s naughty to leave your makeup on overnight, but hey, when I get up next morning at least I still look “femme”.

Although in drab for the drive home, underneath I was still Caty. I arrived home mid afternoon via my storage unit to drop off most of Caty’s gear. With my beloved not due home until midday Monday, Sunday night meant another restful night as Caty. But not before washing some of Caty’s other lingerie and hanging it on the line overnight. I had intended to be dressed again in private Sunday afternoon, but events transpired to prevent that, namely the desire for a good pizza for dinner; it had to be collected in drab.

My beloved does not have that many “away trips” these days, so I’m not sure when the next one will be. What I do know; it was my third complete makeover and shopping/dinner outing in the last twelve months and I can’t wait to do it all again!

Especially, if next time, I do get to Lisa’s Lacies for that en femme bra fitting….

Happy dressing everyone!

Caty Ryan.

More Articles by Caty Ryan

View all articles by Caty Ryan
The following two tabs change content below.

Caty Ryan

"Mature aged" crossdresser living in Victoria, Australia Love all things feminine especially classy lingerie and formal gowns. Have a long standing passion for period wear and own three lovely replica period gowns, 2 1700's and one American Civil war replica. Love to chat via e.mail with anyone with similar interests

Latest posts by Caty Ryan (see all)

5 1 vote
Article Rating
Notify of
Inline Feedbacks
View all comments
Rozalyne Richards
Active Member
1 year ago

Hi Caty thanks for sharing your story with us x the only time I get to let Rozalyne out is when my wife is away too, the last time was at the beginning of September for a few days it was fantastic being Rozalyne with knowing that I knew I wasn’t going to be caught, unlike you I have never been out either shopping or for a meal, i hope that i get the chance to do both in the future, it would be so lovely to have a makeover with a professional photo shoot then go to a venue… Read more »

Active Member
1 year ago

Great story Caty thanks for sharing , Always love reading them

Active Member
1 year ago

Caty, what a great story…thank you so much for sharing…
I too dress when the opportunity presents itself…my wife
knows but prefers not to participates with my dressing en femme… Kathy plays cards twice a week … I have a 3 hour window to put my “gurl” on… On two occasions I have had a makeover which I love to be pampered…. Thank you for listening..Leonara

Anne Preuss
Active Member
1 year ago

Dearest Caty, I loved reading your story. Like you, I long for those moments when I can dress as my SO does not know of my dressing, nor would she accept. It was a 10-day mission trip in 2017 when she was gone and I plunged down the rabbit hole, ordering silicone breast forms, padded girdles, bras, clothes, a wig. It was decades in the making but those 10 days allowed me to reflect upon, accept and love who/what I really am. Then came another 10-day trip for her in 2018 and my experiences and prowess as Anne grew and… Read more »

Alexis "Lexi" Moon
Active Member
1 year ago

Great story! I feel your pain about not having time…my son ended up living at home while going to college, so he’s around all the time. Luckily, I still travel for work, and I’ve gotten fairly comfortable with bringing my girl stuff with me. Plus, I actually feel safer going out in a strange city, where I know I won’t bump into anyone I know!

Morgan Staar
Morgan Staar
1 year ago

omg…I had to do a double take…you look very much like my aunt Julie…


Morgan Staar
Morgan Staar
1 year ago
Reply to  Caty Ryan

yes,,,the gown pics especially the mother of the bride gown remind me so much of her,,
She is my favorite aunt….but never gave me sexy leg shot like in your pics…lol

skippy1965 Cynthia
Trusted Member
1 year ago

Re CDing being a “winter sport”, I wrote an article a while back on that subject

Thanks for writing such a thoughtful article Caty!

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account