What did you struggled with when first dressing?

[Brandie.n]

What did you struggle with when you first dressed?Then one fine day you was doing it like normal forgotten you had to struggle with it?
Me first,my struggle was hosiery every time i put on tights or pantyhose I would twist the leg.I would have to take them on and off until I got it right.I could put on stockings and wind up twisting the leg lol. Today I was playing dress up and put on my hose and it hit me I got over that hump.I can put them on the right way now but,I don't remember when it clicked and started putting them on the right way..

[Tracii G]

Make up for sure.
I know lots about make up and how to apply it correctly now but I still mess up sometimes and get it all wrong.

[docrobbysherry]

My face!:doh:

I nearly quit dressing before I'd really gotten into it. A hot, young woman's shape with the face of a homely old man!:sad:

Then, Halloween came and I tried on a female mask!:heehee:

[Jean 103]

Self acceptance and guilt.

I still remember as it wasn't that long ago.

As far as dressing it would be false eyelashes. I still have problems. Lucky my lashes are ok so I just use mascara.

[Helen_Highwater]

Brandie,

Shoes, trying to squeeze my size 9's into my GF's size 6's.

Makeup as Tracii says was always an issue. It wasn't until I had a foundation match that I realised I'd been using one too light and so veered more towards a clown face.

Now thankfully I've learned to put on a workable face and in about the same time it'd take the average GG. Still can't get to grips with liquid eye liner though.

[Sarah Handy]

Walking in heels and still struggle.

[Bobbi46]

Lipstick! when was too much too much! now I put my lippy on and then close my lips over tissue until the surplus has come off then there is no problem with cups and so forth

[alwayshave]

For me, it was then and still now, eye makeup.

[Angela Marie]

I agree with Jean. Self acceptance and guilt; which I am still plagued with from time to time. As for the other issues; as many have stated makeup. It is an art form; which I still struggle to master.

[EyoN]

I reckon many, including myself, struggled with make ups (and especially eye make-ups).

However, I personally also found it difficult to conceal wide shoulders and chest, as well as low waistline, and it really comes to picking the right cloths. Even if the cloth is just the right length, it is almost always too tight somewhere.

[Madilyn A.]

False eyelashes, getting my wigs just right, finding heels in my size, and sufficient time to dress and enjoy myself .

[GretchenM]

Guilt about doing something I "knew" was wrong but couldn't help myself or stop. It was a deep internal drive and it scared the crap out of me. Did it anyway. I was only 7 years old, that was 1952. And I suffered the consequences when I got caught. Drove me into a very deep closet for 60 years. Now, no guilt - it is a part of who I am, warts and all.

[gailprice]

Yes, make up for me. Eyes were the worst.

xx

[BrendaPDX]

Makeup, then and still now.

[Davina Katherine]

Makeup; eyes (hooded) and lips (thin). And self-acceptance.

[Zoeytgtx]

Brandie:

In the beginning, a lot of guilt and self loathing. Completely denying it was NOT ONLY the dressing. Of course, learning how to do eye makeup and liner on my hooded eyes.

Five year later, I happily understand I?m TG and unashamedly go out in public and I present quite nicely according to my GG friends. It?s all about growing into who you really are and accepting it.

Hugs, Zoey

[Amelie]

Men. How to deal with men. I knew guys were trouble but it seemed that since I became a girl I met a whole new breed of men. And it was a struggle learning to weed out the psychos.

Make up was easy for me. Just took a pic I liked from a magazine and copied the look to my face. I already was using artist brushes to paint so I knew how to draw a straight line with the liner.

A minor struggle was trying to find goth clothes back then.



PS- Finding a job as a t person was a struggle.

[Majella St Gerard]

Make up was tough, but I got that down, liquid/ gel eyeliner I can not do though. Heels are not that hard to master (under 5 in.) unless you have a balance problem

[NancySue]

My first experience was with nylons. It was fun but, I struggled with slipping them on correctly. Then finding time to wear them again along with some guilt and fear of getting caught. I?ve overcome guilt and fear long ago...thanks to my wife. Currently, putting on my makeup is always a venture. As with life, I have good and bad days.

[CynthiaD]

When I first started buying my own dresses, it took forever to find the styles that looked good on me. My local thrift store has a whole rack of my mistakes. (Well, they could if they put them all together.)

[Cheryl T]

Jean 103 nailed it.
It was the guilt and shame for me. I loved the clothes, could dress with ease even with seamed stockings, I was walking in heels when I was about 8, but removing the clothing and feeling all that guilt and shame was the worst.
It was decades before I was able to accept myself.

Now the challenge is makeup for an older gal. Eyesight requires glasses so eye makeup is my nemesis.

[Stephanie47]

My first interest in wearing women's clothing was in the early 1960's. I struggled with just the concept of wearing women's clothing. Back then the word on the street, i.e., society, was any man wearing women's clothing was a homosexual. However, the word homosexual or gay was not used. All terms were derogatory. This brought about a lot of conflict since I lusted after girls my age and unattainable starlets on the movie screen. Any way, the early years were filled with self loathing, disgust, hate, confusion about myself. Obviously the internet did not exist back then. There was no printed material around for a kid to read. Even the local library hid behind the librarian's desk the copy of the Kinsey Report. If all you had to worry about was trying to put nylons on then you are lucky. That was the least of my problems back in the 1960's.

[Star01]

The first time I dressed I was too young to understand what was going on. At first it just seemed like a one time incident and as bad as I felt I obviously wasn't going to tell anyone. Well, here I am about 56 years later at 68 and I guess that it wasn't just one time after all.

Today my biggest struggles are applying eyeliner as I need to wear reading glasses and I have always had trouble shopping for girlie things in guy mode. I went into a thrift store yesterday with my nails clear polished and star earrings while underdressed in a thong, looked at the women's shoes, looked at the ladies browsing the dress racks, freaked out, smiled and said hi to the clerk and left.

[Jenny22]

Too much self gratification, and the post shame of it. Much later, my need to acknowledge that I was true TG.

[April Rose]

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!:wall:

Since my first memory of being attracted to women's things was also my first memory, my earliest trouble was overcoming the feeling that I was bad and queer and going to hell.

[Davina Katherine]

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.

[Stevie Allyn]

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! :D

[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

[Stevie Allyn]

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 Doepner]

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!

[JuliaGirl]

Makeup to this day.

[Victoria_Winters]

For me I have to say it is the makeup and embarrassment... I used be very embarrassed by dressing. Now I am at the stage in my life where I saw why the hell should I cam what other people think!

I still struggle with makeup. I?m entering the world of Being. Drag Queen but I want to look like a real girl not a clown. So I am working still to get better at makeup. This weekend I am learning how to do a nice smoky eye!

[Lana Mae]

Definitely eye make up! I even had instruction and can't get it straight!
My being naive about all this until I was 65! Yes I realized much of it but did not apply it to myself! Oh, yes it is me alright! LOL
The decision to start HRT!
Seriously!
Hugs Lana Mae

[Taylor186]

Finding time to dress without discovery while deeply in the closet.
Finding a safe, non-obvious, hiding place for my things.

[Fran out]

Initially it was trying to understand my urge to try on female clothes followed guilt, confusion and questioning my sexuality.
The top two are:
Where to store my female things
Make up..... I'm still struggling and need help here

[Desiree2bababe]

Makeup without a doubt!

[AllyCDTV]

Eyeliner. I love an intense Arabic style and I usually wind up screaming, "good enough" after spending way too much time struggling with it. I also have to take 2 tries to get false eyelashes in the right position.

[xEvelyn]

Voice has always been the hardest part. I still avoid interacting with people because it is so incongruent.

[Nic J]

Something that i had difficulty with at first was finding the right type of female clothes to suit my figure. (i don't use forms/padding)
Fortunately i am short and skinny and my hip to waist ratio is very good compared to most GMs, but even so i quickly discovered that some clothes that looked great on women didn't look good on me.
I had some great guidance from my wife about garments to try and have now found certain looks that suit me.


Initially it was trying to understand my urge to try on female clothes followed guilt, confusion and questioning my sexuality.
Yes, i had the same feelings of confusion, shame & guilt when i began experimenting with CDing, altho in my case i was always clear about my sexuality.

[mbmeen12]

That I was initially a sexual delinquent and was far from the normal. After a while, I realised it was the vanilla world that was in denial of their true selves.

As to the dressing, the epiphany on why I cant hook a bra from the back.... large man arms dont stretch like a nat gg.

[JuliaGirl]

Finding time to dress without discovery while deeply in the closet.
Finding a safe, non-obvious, hiding place for my things.

OMG, this.

[fun4metoo2004]

Makeup. Still struggle with it.

[Davina13]

Oh yeah,make up for sure is a struggle. But I keep at it,I have to get better eventually.
And I always clip my bra in the front and spin it around.

[crissy7]

clothes never a problem.makeup used to be ,but not so much now.

[Maid_Marion]

I got a free tube of lip gloss from VS. You may want to try some if you have trouble putting on lipstick or just want something a little less obvious. I've been putting it on before going to work.

Marion

[Allyssa66]

Buying fem stuff to wear

[jacques]

Hello Brandie
finding the right sized bra was not easy. And then learning how to wear it!
luv J

[darla_g]

I've practiced makeup consistently and watched tons of videos on techniques . Whenever i dress i have a specific makeup look in mind.

I struggle with certain heels. 3" heels is my limit or i basically can't walk

[prene]

Makeup,
clothing that fits my tall figure,
Guilt and self-acceptance,
Finding a accepting GG,
Men ... arg

[Maid_Marion]

Some heels are designed only for looks and are terrible for walking.
I studied the reviews before choosing what to buy.
I've gone shopping in heels.

[AllyCDTV]

I got a free tube of lip gloss from VS. You may want to try some if you have trouble putting on lipstick or just want something a little less obvious. I've been putting it on before going to work.

Marion

Great advice Marion. I used to struggle with lipstick all the time. Tried lip gloss a while back and haven't used lipstick since.

[Natalie5004]

I tried False Eyelashes today for the first time. What a joke. Man they make looking like a woman tough. I am gain a lot more respect for what women do every day. My hat is off to them.
I will practice my eye lashes more.

[Kelly Pearson]

Always eye liner for me.....still struggle sometimes

[BaliGirl]

Here is what I've struggled with:

- Guilt and shame about enjoying cross-dressing. Self-acceptance.
- When I started cross-dressing as a teen, fighting myself to not do it when I had the opportunity. I could only cross-dress when I was alone at home, and it was hard to predict when this would happen. So when I was alone, I tried not to do it. Mostly failed.
- The fear of getting caught. I played it safe most of the time, but one time I risked putting on a front-close bra when I wasn't alone because I'd never done it before.
- Guessing clothing sizes. I'm not brave enough to shop in stores, so when I started buying clothing it was a guessing game about what would fit.

[MonicaPVD]

In the beginning! I have large feet and when I first started it was nearly impossible to find women's shoes larger than 10 or 11. When you did find a pair, they looked like they were designed by Dr Who. That was a struggle. These days everything is a click away.

[Vicky_Scot]

At 12 my real struggle was trying to hide my lingerie etc so my mum did not discover it when she cleaned my room. X

[Teri Ray]

Like others I would say I struggled with "why do I have this desire" then accepting my desire and behavior. Whew...…… I did want to dress up and for the life of me I could not ever understand why I did. Oh and eyeliner.

[Angie G]

Getting the eye liner right. :hugs:
Angie

[shellybme]

False eyelashes, getting my wigs just right, finding heels in my size, and sufficient time to dress and enjoy myself .

ditto! The struggle lol

[APRIL0401]

I have always had problems zipping up my dresses.
Also have problems trying to tie a perfect bow on my dresses that have them.
That's when I wish I had a understanding SO to help me.

[Rhonda Jean]

Ignorance is bliss. Hard as it may be to believe in this day of unlimited resources, 40+ years ago I really didn't have an ideological struggle with it. I felt pretty free to be different and was largely unaware of the huge implications.

As far as in-practice struggles, if I was looking back at old pics I'm sure I'd say I struggled with makeup, but I didn't think I was struggling then. Eye shadow was blue and lipstick was red. I wore pancake makeup, and lots of it. GG's did the same thing back then. Heavy foundation was the norm. We didn't agonize over perfection, and were not really aware of what perfection would even look like. I wore my makeup about like other women did. I don't think anybody ever heard of contouring. I remember my first pro makeover in about 1985 I was told to make a "V" with my fingers out from my ears and apply blush there, then the jaw line, then above my brows, then right in the middle of the top of my forehead. I had more blush(ed) than not, and I thought I looked like a supermodel. I'm sure if I could see those pics now (that my ex has) I'd think I looked more like a clown.

Less knowledge, less struggle.

[countrygirl]

For me it is makeup as I don't want to look like a clown. When I first started off I looked like one. It has gotten better. Still not where I want to be but I feel comfortable enough to go out. I am still wanting help some to bring the eldery lady that I know I am out. One day I will be able to do that.

[Kelli_cd]

I'm struggling with weight. I want to look good in a dress, not look like I'm pregnant.
I can look okay in tunics or loose tops. And skirts are probably right out for now.

[lingerieLiz]

I think acceptance in the 50s. When I moved away from home I thought people looked down on me. I was lucky. I worked for an upscale store and some of the women recognized my desires for women's clothes. Lingerie was hard in the beginning, but one of the SAs had a friend at a lingerie store and told me she would be happy to help me pick stuff for my "sister". The break through was when I went to a movie with a friend as Sandra Dee.

[candice.aihara]

For me it was back closure bras. Ah, such sweet innocent times. :)

[Joanne108]

Looking like a woman. I feel that I have gotten better! I had to figure it all out myself. The last time I dressed I took pictures as usual, and several of them looked outstanding. So the progress continues.

[MonicaGirly]

Makeup was hard but a lot of fun and heels just took practice.

For me the hardest(and scariest!l part was figuring out how to get out of a bra!
Particularly when I first started as a thirteen year old who only had 30 minutes home alone before anyone got home. One time pretty early on I really couldn’t get out of it and I heard a car door shut in the driveway.

Talk about an adrenaline rush!

Luckily I escaped just in the nick of time, but I’m sure many of us have had similar close calls.

[Kay J]

For me i was 6 or 7 years old and it started with my moms nylons and panty girdle the nylons were just to long so i would attach pass the welt onto the stocking it self i will never know how many stockings i put runs in but i know a lot and yes my mother did know but i don't think she told my dad thank God.

[MarinaTwelve200]

Shoes and hair Mostly-----Cheap wigs were not around when I was starting out at 13 or so in the early 60s----An while I was my mother's shoe size--her shoes were too narrow for me.-----But scarves and hats could hide my short hair and since I never went out shoes (though desired) were not needed.

[Christina89]

honestly with a bra at first. i used a bikini bra for the longest time before i learned how to use a real bra. lol

now it's mostly make-up

[Dana Marlena]

Finding heels in the right size was always tough - that and false eyelashes, it took me a while before I could get my eye makeup just right

[RochelleCD]

When I first started I had trouble figuring out how to put on a bra, hook in back/hook in front and rotate, if I hooked in front I would have it upside down half the time. I can do bras easily now , make up is my bane.

[fun4metoo2004]

Makeup. Hair. Fashion, although the GG friends I have tell me I dress better than them.