By Caty Ryan

Via Cross Dresser Heaven I have established a lovely friendship with a wonderful “younger” lady namely Dani Richmond. Dani and I have met for “underdressed drab” coffees for several months now, but she, unlike yours truly, has never been out in public before as Dani. So in order to correct this state of affairs, she arranged to have Celeste from Transformations by Celeste do our makeup and thence for us both to venture forth into the wide world.

Prior to this, Caty had done her usual book two nights, self-contained accommodation routine at another location closer to Celeste other than at her usual S.C. “bolthole”. Go there the day before in “drab”, set up the room, not to return until Caty and Dani were ready to do so after the “outing”… (Though Caty did go there on the morning of the makeover to be “underdressed” before Dani picked me up and drove us to Celeste’s abode.).

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Dani initially only thought she had the courage to do the initial “park walk debut,” but as the day wore on, her confidence grew and a lot more positives occurred.

Thus we arrived at Celeste’s. Yet again, Caty experienced that wonderful pampered feeling of a woman doing her make up for her; so relaxing… Once mine was completed, it was Dani’s turn. I adjourned to the living room to do my nails—(as in double sided sticky pads on first then nail glue, then the nails.) I always feel better with these on my big, male hands; without them, they are a bit of a giveaway.

Winter in Melbourne is a great time to “rug up.” So as not having been the Clever Secretary for at least a year, it was my outfit choice for the day. With the exception of a grey long sleeve top/pink scarf everything else was black—skirt, jacket, heels, shoes etc. Dani opted for winter smart casual; she chose an olive skater dress, black tights, grey scarf, and tan ankle boots.

With our makeovers completed it was time for Dani to “rise to the occasion.” Blackburn Lake Park in Melbourne’s eastern Suburbs was the venue for her debut. We walked for about 500 m as many people passed us both and never batted an eye. We were just a couple of sisters out for a winter stroll. Walking back past a crowded playground gave Dani the flutters, but again, no one took a scrap of notice of us.

So now emboldened, it was off to a nearby local, smallish shopping centre. Target and Harris Scarfe are good stores for us “mature ladies.” A stroll through those two was a must. Dani’s had a moment when a car load of family members pulled in right beside us as she was locking her car. There was at least one teenage girl amongst them who I bet could spot a CD a mile away, but again, nothing happened.

With our shopping trip completed, it was time to go “back to the ranch.” There was more wordless interaction with the general public, especially in the lift going up to the room, but no one screamed, “Oooohhhh, they are blokes in a dress!”The balance of the afternoon and early evening were spent at a photo session, as well as in nice long girly chats, followed by dinner and drinks. Afterward, Dani returned to “drab” and went on her merry way.

This left Caty alone to enjoy an early night and a peaceful night’s rest, after partaking in Caty’s routine of enjoying some ice cream. Caty enjoyed her night as her “self imposed leave pass” was not due to expire until the afternoon after our makeovers. Although I did not think any of the people we saw during our day picked us as crossdressers, Dani begged to differ. She said it happened at least three times…..

Happy dressing one and all…




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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
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Rozalyne Richards
Rozalyne Richards
3 years ago

Hi Caty thanks for sharing your story with us x I wish i had a friend like you that would take me in hand and show the wonderful times of going out en femm, the close’s I’ve been out is late night drives in my car, my top dream is to attend a venue near to me and have a full makeover as well, i would love to wear a nice sparkly party dress with heels and some nice lacey lingerie, hugs Rozalyne x

skippy1965 Cynthia
Trusted Member
3 years ago

I love hearing stories about girls formerly afraid to go out who venture out their first time. I was in that position just four years ago when I made my first run through a drive thru. Since then I’ve gone to six cd/tg conferences, concerts, movies, dinner,shopping–even lying cross country. It gets easier every time. Whether someone “locks” you or night, s long as they don’t make rude comments or point and laugh I count any time put a success. Congrats to Dani and thanks to you for helping a friend venture out!

Trusted Member
3 years ago

Caty a very elegant lady.. You are amazing..thank you so much for sharing.. Happy holidays and happy & healthy New year… Leonara

Trusted Member
3 years ago
Reply to  Caty Ryan

I love your sense of humor…”under elegant” suits you fine… I forgot you are experiencing summer… Although we are in our winter temps have been above normal ..
However, my “under elegant”. Includes the usual padded panties, cami’s , and pantyhose or thigh hi’s…be well.
Hopefully you wil experience break in the weather and you can show us the latest choose to be the elegant lady that you are.. Be well…Leonara…

3 years ago

Hello Caty and CDH community,

I am the Dani that made her public debut under the very experienced hand of Caty. After months of encouragement, she finally had me stepping out and experiencing that femme feeling that we all seek.

I promise I will write an account of this adventure from my point of view and publish a pic or two for all to see me for the first time, albeit, I might be wearing my security sunnies.

Thank you Caty, you are an amazing girlfriend.


Gail Bingyi
Active Member
3 years ago
Reply to  Dani

Go girl

Amy Myers
Noble Member
3 years ago

What a wonderful experience for both of you. I’m so happy for you, and esp Dani to have a mentor like you.

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