What did you struggled with when first dressing?

[Jessie Mae]

April Rose (btw, beautiful name!), glasses are also a pain for me. I got a 5x or 10x (can't remember) magnifying mirror.
With my face about 3 inches away, I can see well enough without my glasses.

[April Rose]

Thanks, Jessie! I have one of those too, but it's still an exercise in frustration.

[Dressing up]

My issue years ago was dressing appropriate to the environment I would go out to. Back then, my opportunities to dress were more limited and when I did I wanted to go out somewhere. I wasn't out to anyone back then except my wife and I had much less free time when the kids were young. When I got some free time, I would doll up with dresses and makeup and then think about going somewhere neutral like a store or get gas for the car. My makeup skills were awful and my clothing choices were not appropriate for the venue.

Now I have more time to dress and I usually dress very casual and run my errands for the day. From a distance, few notice me until they get close.

I agree with some above, I may never get the hang of false eyelashes or liquid eyeliner. I do love the liquid eyeliner look though.

[Amalou]

I too had trouble with dressing appropriately. One of the funniest occasions was when my wife came into the bathroom to see how I was getting on with the wall tiling, to find me standing on a stepladder wearing a pastel yellow miniskirt, bra and breast forms!

[Marianne S]

What did I struggle with when first dressing?

Getting the zipper up and down at the back of the dress!

[Patti Remick]

I dont remember having much difficulty when I dressed at first because I was 7 or 8 years old and I was dressing in my older sisters (I had two) older clothes from when they were my age. So everything fit me very well and was very age appropriate. I found putting on their clothes to be quite easy and natural. Perhaps I struggled a bit with the fact that when I looked in the mirror I looked a lot like my sisters. But not too much or a struggle as i so wanted to be a girl.
Luv and hugs
Patti

[Star01]

Star , the eye makeup thing is a no win situation for me; can't see what I'm doing with my glasses off, can't get at it with my glasses on!

That is exactly what I struggle with when applying the eyeliner but the rest isn't too bad. My hastily purchased costume store wigs are junk so they make me feel lousy whenever I put them on but I will resolve that soon.

[Andy1087]

For me almost everything involved with dressing is a struggle. Like I said before the only thing I have gotten right is pantyhose and panties. Everything else about dressing is a challenge for me. Make up, getting the right size in clothing so much so that I have not bought any clothes in years. I have dabbled with dressing over the course of 30+ years and all my failures of my attempts makes me very frustrated and upset with myself. This whole thing has been weighing pretty heavy on my mind of late, so much so that I have trouble sleeping some nights.

Andy

[Amalou]

Andy, that is so sad that you struggle to find the right size clothes.

Have you tried buying online from a store that offers free returns? We have several here in the UK which I buy most of my femme clothes from. I can order say two different sizes of a dress (for example) and return one, or both, if they do not fit. Also they have online sizing guides which help you find a size which should be close to a decent fit.

I wish you much better success in finding clothes that fit you well.

[BTWimRobin]

So far I'm struggling with everything:
- with my own acceptance
- coming out to my wife
- going shopping
- figuring out what size I am
- creating my look
- dry time of nail polish
- finding shoes that fit
- and I haven't tried makeup yet

The only thing I haven't struggled with is walking in heels. It feels so natural.

Whether I am struggling or not I am enjoying my journey.

[melaniethecd]

This reminds me of how awkward something as simple as putting a bra on used to be. Lining up the clasps, making sure the shoulder straps aren't twisted, etc. Slipping my arms in and hooking it behind my back is second nature now.

[Karmen]

Mostly makeup, but walking in heels and buying female clothes or shoes was also a challenge at first.

[Jenny22]

For you girls that have vision problems trying to put on makeup, Google .. Makeup glasses .. You will find several different types that might benefit you.

[Sabrina133]

Like many here - self loathing and questioning by sexuality and gender. It took many years to come to accept myself for who i am.

In terms of dressing itself - make up. It took lots a time and experimentation. It wasn't until i met a drag queen who spent time teaching me the art of make up that i got good at it.

[Judy-Somthing]

I also say struggle with "Self acceptance and guilt" and still do!

Back in my teens I had many purges where I would rip everything up so I couldn't rescue it from the trash later. ARRRRRRRRR

Back in my teens, finding nice heels that fit.

This Self acceptance and guilt seems to go hand in hand with cross-dressing.

[KrissyCD]

Like many others here , self acceptance and makeup. So many of you here are just stunning. I do not get to practice as much as I would like. I watch videos and such but nothing is the same as practice. I wish I could just do a makeover or transformation day and see what a professional can really do. Would make me feel so special.

[candice.aihara]

What did you struggle with when you first dressed?

Not knowing what matches. Eventually, though, I could put myself together in a lovely outfit both in look and feel.

[Jane G]

Simply relaxing and being me. Age has it's benefits.

[Sissy_in_pink]

Yep, makeup was the biggest hurdle for me, I still only do the basics, anything fancy forget it.

[Connie D50]

Like some other (Self acceptance and guilt) sometime the guilt was so bad I would be sick. However I would be looking for the next chance to dress a day later. Again the internet (crossdressers.com) was a big help for me.

[donnalee]

After spending 3 hours trying to draw straight brows with an eyebrow pencil, I had to give up anything past lipstick. I was endangering my sight with a eyebrow brush due to shaky hands and could not see where to put them.

[Rachel05]

The guilt and lack of understanding how to understand something different, no Internet forums back when I started and I definitely felt awkward and different, that was a struggle

Then it was bras, fastening bras for a start and also how to have them not show beneath your shirt

[Sarah Charles]

Learning in isolation without understanding what I was really experiencing was most difficult. I had to use the language that was available at the time and it was almost always negative or pathological, none of which helped. After that it had to be liquid eyeliner, false eyelashes and figuring out why a size 14 by one manufacturer was a 12 or a 16 by someone else.

[tmonsivais]

Emotionally, shame, guilt, and self-acceptance. As for dressing, tucking where it actually feels comfortable and give me the look that I want.

[valerie anne]

The final realisation that I really wanted a bra, stockings and red lips.

The terror in ordering these online, fearing my order would be rejected.

The wait for the delivery, dreading it would go next door.

The relief of opening the parcel to reveal the sexy, girly things, and the joy of fastening the bra, to find that with a bit of padding, it fitted!

That first parcel, that first bra left me shaking!