Susan's Place Transgender Resources

Hi I'm Samantha, I have been interested in crossdressing since my teens and now I'm 45 I have finally plucked up the courage to act upon it. It is so difficult to start though, I'm struggling at the moment to find the right look and to be truthful it's overwhelming. I'm hoping this site is a good place to start my journey. I have read some posts on here which are inspiring and I look forward to making the journey with you all. All my love Samantha x

May I ask what you mean by "act on it"? Have you not dressed since a teenager and now you want to revisit that or does acting on it mean you've dressed occasionally in private but you want something more significant like going out in public?

Regardless of your answer, it's never too late. We all have our unique paths and they can be very different to the next trans woman or CDer. And at 45 years old you still have a lot of time to explore that side of yourself.

Hi Samantha!

Thanks for the wonderful introduction. I am glad my welcome message found you. For me, when I first came out, I subtly began changing my wardrobe. First, just women's jeans, then tennis shoes, then different tops. Then added jewelry, a bit of eyeliner and concealer. Then added a wig and spent more time with makeup. I just went slow and upped the game a little as my comfort level increased. Most people will not pay attention to you if you are just blending in. What draws attention is excessive makeup (bright colors) and clothing that is inappropriate for the situation (sexy, formal, flashy, etc.) while grocery shopping. For those who are into drag, this might be okay, but it wasn't for me.

You can also check out our Cross Dresser Forum at: https://www.susans.org/index.php?board=23.0

And now I will step aside and let our members help you.

Quote from: Jillian-TG on Yesterday at 07:03:46 AMMay I ask what you mean by "act on it"? Have you not dressed since a teenager and now you want to revisit that or does acting on it mean you've dressed occasionally in private but you want something more significant like going out in public?

Regardless of your answer, it's never too late. We all have our unique paths and they can be very different to the next trans woman or CDer. And at 45 years old you still have a lot of time to explore that side of yourself.

For me it's always been alone in the bedroom kinda thing looking in the mirror admiring the look, have worn lingerie under my normal clothes but would like to step out further. I have started to go to a local place where on a Saturday they have a crossdresser transgender night, so iam starting there to build up to one day going out as a woman and doing womanly things like shopping,lunches etc.. I just want the look to be right where I feel great and womanly before i do. At the minute iam looking into shape wear and dresses to give me the figure I desire and to cover up my manly attributes. I seem to spend most of my time browsing trying to find what iam looking for. It's so hard 😫, I do look forward to the day when it all comes together 😊. Thankyou for your time in responding to me, it really helps x

Welcome and so glad to hear you're ready to explore this further. With regards to finding looks I totally get that! I'm still experimenting after a few years. To be honest I just copy the looks I see online as best I can or buy cheap second hand as if it doesn't work it's less of a loss.

What's apparent is that learning everything many cis women learn over years in a shorter time frame is hard work and deffo comes with some faux pas!

I think you're already doing well by the sounds of it getting out there to the CD night you mention. I built up similar but at furry meets. Not long later was getting out much more.

Charlotte 😻

Hi Samantha,

Welcome to Susan's.

Lori had some very good advice.  Just start by dipping your toes in the waters.

-Paulie.

Welcome Samantha!

Thanks for visiting with us and please return often!

I suggest for figuring out what to wear in public that you pay close attention to
What women you age, size, and build typically wear, seasonally adjusted.
Know what look you prefer, and think seriously if that look would work for you in public.

Also:
  Do not spend lots of money right away on clothes.  Get the basics, nothing outlandish.
  Try to simply look like an ordinary woman your age, not a glamorous runway model.
  Go to Sephora for a makeup lesson and basic makeup.  Do not buy tons, a good concealer for sure.
  I suggest starting with androgynous clothes but to move to women's jeans, hiking shoes or sneakers, penny loafers, maybe a women's Polo or T shirt, and sweater.  Maybe a ladies Oxford shirt.  I would skip crop tops!
  Undressing garments are up to you, no one can see them.  But many bras are not that concealable if that is a concern.  Perhaps it is easier to not see a t shirt bra than other bras.
  Go slowly, move from androgynous to a slightly feminine to a more and more feminine appearance.
  For a wig, if needed, go to a wig salon.  They can be a big help.  Buy cheaper ones first.  You can order online if you prefer.  Try some styles that you like.  Some colors you may like but they really will not suit your complexion.  Try wig styles with clothes at home before venturing out. 

I also suggest contacting a transgender or specifically a cross dressing support group.
They sometimes have makeup sessions, clothing exchanges, have someone to go to stores and shop with you for female clothes and shoes, and can be otherwise helpful.

Look for many responses here from others, some may be of help for you.

Chrissy

If it were me I'd just buy some women's jeans, a blouse or a slightly feminine top, some women's flats, a bit of jewelery and whatever minimal makeup you are comfortable with then go to the cd/tg night and find a few friendly ladies and introduce yourself. I guarantee you won't regret it.

I recently went to a lady gaga concert presenting as male. Small silver hoop earrings, silver braclets and watch, lady gaga womens tee, womens exercise shorts and fishnet tights.

It was a great night and I don't recall ever having so much female attention.
It was an experience. One woman asked if I was going to the show as she thought I always dressed like that. Another came up to say she liked my outfit and that I wss the gayest guy there.

I was quite flattered by that and my wife pointed out I'm not gay, I pointed out I really wasn't the gayest person there but thanked her for the attention. Her husband and two younger companions were quite embarrased by her but I didn't care.

If you are lucky enough to have a safe space and be among a supportive crowd just do it.

Don't wait until your 6 decades in as you will regret opportunites not taken.

But be safe!

PS. This was my first time out with my wife and friends in anything other than full male attire

Hi Samantha, and welcome to Susan's Place!

Thirty years of carrying this quietly, and now you're stepping forward at 45 - that takes real courage. The overwhelm you're feeling is completely normal. You're essentially learning in months what many cisgender women absorb over decades, so please be patient with yourself.

I love that you've already found a local CD/TG night. That's genuinely one of the best ways to build confidence in a supportive space before venturing into everyday settings. The women there will likely have practical advice about what works for your body type and where to shop locally.

A few thoughts on finding your look:

Start with fit over fashion. Shapewear and well-fitted basics will do more for you than the most gorgeous dress that doesn't quite work with your frame. Many of us spent money on things we loved on the hanger but never wore twice.

Thrift stores are your friend early on. You can experiment without the sting of expensive mistakes. Once you know what silhouettes and colors work for you, then invest in quality pieces.

Watch women your age in everyday settings - coffee shops, grocery stores, work. Notice how most women aren't dressed glamorously; they're comfortable and put-together. That's your target, not the magazine cover.

The "right look" you're searching for? It evolves. You'll find it not by waiting until everything is perfect, but by trying things, keeping what works, and letting go of what doesn't. The confidence you're building at that Saturday night will translate to daytime eventually - one step at a time.

We're glad you're here. Keep asking questions, and enjoy the journey.

With love and support!
— Susan 💜