Shopping is scary, but then gets easier.

Hi All,
This is my first post and I hope it is not out of line. I've read many of the shopping threads and the ones that went where I'm going are a few years old. Hopefully, reading about my recent experiences will help others.

I'm in my early 50's and have been secretly wearing my wifes dresses on and off for the last 35 years. About a year ago I decided to finally tell her. All I got in response was "just don't do it in front of me". I then told two very close female friends. They were both very supportive and one has even been shopping with me since!

About 3 months ago I was travelling alone well away from where I live. For many years I had looked longingly into the womens clothing shops and the womens sections in the department stores. Well, on this trip I finally decided to bite the bullet. It was now or never. I walked into a Big W and tried to browse the dresses without looking like a pervert. It was extremely nerve-wracking and I had to walk out after a few minutes. But, what a rush!

I then wandered around a bit and walked into Target. This time I though 'no turning back'. I browsed through the panty section and picked up two pair. Then went to the dresses and quickly grabbed a nice maxi. I was too scared to even worry about sizes. I just wanted the experience. Going through the checkout with these 3 items was another rush. The middle aged woman serving didn't give me a second glance.

So that was done. I then walked around the centre some more looking into the windows of the specialist womens shops. Even went into a couple briefly but quickly escaped again. Walking past a City Chic shop I was enticed by the lovely dresses on display. I went in and spent a good 10 minutes browsing while the SA dealt with the other customer in the store. When they left she came and attended to me. she asked a number of the usual questions. In the end I gulped and said "it's for me". She was great! No adverse response at all just so lovely and helpful. She insisted that I must try on some of the dresses I'd been checking out, and even brought more to me in the dressing room. I walked out of there on cloud 9. It was so liberating.

After this experience I had to have more. I've since been shopping at least once a week. Walking out of the dressing rooms wearing a dress to check myself in the big mirror and not caring who is looking. (Only with the ok of the shop staff. We need to respect them and their business) I've walked into a lingerie shop and had a bra fitting, and later bought the suggested bra. Then another time I wore that bra under my t-shirt when shopping so that I could see how the dresses looked with breasts. Walking through the shopping centre as a male with breasts was quite fun.

Now I want to relate this weeks shopping experience. Three wonderful moments that are worth sharing.
1. I went into a TS14 shop and the two female SA's could not have been more supportive. At first one of them was hitting me with the normal questions. 'Who was I buying for'. Then the other came over and suggested I try these shoes because they were wide fitting. She knew! Again, they were both lovely and insisted that various items would suit me and kept bringing things to the dressing room. They even offered to give me a private experience after the store closed, where they could bring me items and try various combinations without worrying about being seen.

2. I went into a little womens shoe shop. The young lady knew immediately that I was looking for myself and suggested various pairs. Maybe she had seen the stockings I was wearing. We had a great chat and she even pointed me to a local CD support group that has public meetings.

3. Shortly after in another dress shop I was browsing while the SA attended another customer. As that customer left, two more ladies entered. The SA called out "Hello girls". One of the customers said "that's a man over there". The SA said "no, that's a girl too". I laughed so hard and told her she was correct. Such a fun moment.

So, what I am trying to say in my long winded post. Shopping gets easier and is well worth getting into. I haven't spent a lot of money but I've had so much happiness. Go for it!

Hi Angela,

Thats quite a story but I sure do admire the courage you have shown. I'm still largely an online shopper and its stories like these that will get me to my first shopping in town in the near future. Thanks for sharing and take care!

Hi there, and welcome to the forum, Angela!
What you say is so true! It was such a nerve shredding experience shopping for my Amy side the first few times, but it got better and easier with practice. After I came out to my wife last year, one of the first things she did was take me shopping (she's so sweet!). She's a bit of a shopaholic herself lol. She created a monster, now we both can't hardly walk past a clearance rack!

Once the genie is out ... watch your bank account, that's usually the first place she hits. :rofl:

And I thought I was the only one. haha.

I would spend....what felt like....hours wondering around Walmart with a dozen items in my shopping cart only so I could sneak in a 3-pack of panties. I'd watch the cashiers and customers, waiting for a lull in the action to head to checkout. So sad. Then I would choose only the cashier that had that "I don't really care" look and wait for her register to open. Sweating.....literally sweating......scared that she was going to need a price check. I'm 49 years old, for heavens sake!

Acting like a teen buying condoms for the first time.

I'm so happy to have found this forum. I used to use all of these worries and fears to put myself down. Call myself a coward because I couldn't buy a stupid pair of panties at walmart. Sit in my car, cursing myself for being so pathetic.

Since coming out CD to my wife, though....all of that is gone and I feel......literally.....reborn. Starting a new chapter in (our) lives.

What a great story Angela! I'm glad society is becoming more accepting of people. I can only hope that when I break free of buying exclusively at one thrift store, that I'll get a similar experience.

Hello Angela, this had given me some incentive. It's great to hear that you have overcome the great of accepting the help from SA's. I think I need to accept that to. It has come easier for me at the box stores like Walmart and target. So maybe it's time to venture out and really get some fun shopping going. It's tough to me that after all three societal negativity going around where I come from and UN accepting parents, bible belt and all to open up. But anyway hurray your having fun. Maybe it's time some more of us just did it like you have.

As you have found out SA's are very helpful to make a sale, many are very accepting if not they will not serve you. The fear we all feel at first is just unfounded and being open helps others to help us. Be careful shopping can become an expensive vice. It is so much fun especially when presenting as a woman, just another girl out and about, enjoy yourself.

Angela,

You could not be more correct! I think you will agree, women love is girls! Girls that will share themselves like women do, girls that will engage just like another girl.

I have had wonderful experience after wonderful experience with the SAs in many women's stores. Some have become good friends, many hug me repeatedly (not a bad thing). All you have to do is be honest, open yourself up a little and they will just fawn over you. Look, we all in some way want to be, act like or be treated as a woman. If you just go with it, that's exactly what will happen.

Kandi

Thank you for sharing your post. If you have a Dress Barn in your area, try shopping there. I'm also getting to the point where I'm going to tell the SA's that these are for me and I would like to try them on. I already do that at Dress Barn.

Hi Angela and welcome to the forum! Thanks much for sharing your great adventure and yes, it does get easier as your confidence builds. Just continue having fun.

Cheers

Isha

Hi Angela,
Big W, TS14, City Chic; it's obvious you're an aussie girl, what part of the country are in in?
City Chic is a favourite of mine, I love the designs of their dresses and lingerie.

A great story!
Welcome...I am pretty new here, too, and I have found what I have been looking for!

I am inspired by your shopping courage! I just recently started to shop. I picked the Walmart with the self check outs first. After buying panties and camisoles, and tights, I have begun to underdress and shop at the local goodwill. I have purchased outerwear twice after using the dressing rooms to make sure I like what I am purchasing. It was nerve racking, and, thanks to all the support here, I was able to do it.

Last night, I bought my first bras from a VF outlet. It was the first time I was at a regular clothes shop (not goodwill.) The cashier asked if I wanted the bras off the hanger. My voice was a little weak, and I was able to say, "yes, that would be great, thanks." I look forward to the day I am as comfortable shopping for women's clothes as I am for drab!!

Peace
St. Eve

Good for you! There is absolutely no substitute for shopping in person, for a lot of reasons. Firstly, it's a ton of fun, isn't it?

Also, I totally agree with Kandi. SA's who are not just helpful but enthusiastic about helping CDs seem to be in the majority. And they are lovely when you are open and receptive to trying on anything. At my favorite store, the ladies have arguments over who gets to serve me next and are even upset when they learn they missed one of my appearances. It's a major boost to my confidence and I have learned tons from them about developing my personal style.

So, now that you've discovered the joy of shopping for yourself, keep at it! The more of us that get out there, the better it is for all of us!

Good for you. I went through the same thing a number of years ago. Yes it took a while to get comfortable, it's no holds barred.

Hi Angela, Welcome to our forum, When you are here you are home.:hugs:

$$ Be careful $ it get$ real Ea$y Real $ qui$$ck $ :daydreaming:

Angela,
Your so right it does get easier !
I went shoe shopping this week and tried every excuse not to do it, in the end I told myself to grab some cash and get out the door . I had a great time talking to SAs and trying on shoes and not one negative comment or strange look ! I still always ask first if they have any objections but have never been refused.

Quote:

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Originally Posted by Amy Fakley

Once the genie is out ... watch your bank account, that's usually the first place she hits. :rofl:

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Um, I resemble that remark, Amy. :D:o

Welcome Angela!!

Angela, I sure can relate to the experience of lingering (loitering?) outside of women's clothing stores in the mall or walking through the Women's department wishing I could stop and shop--or wishing that I was in the club that was allowed to go in. MIt is not very often, even now, that I find the courage to shop openly and only then on the other side of town or while traveling. But I will agree that the times I have admitted that I was shopping for Nancy and tried on clothing in women's stores has been truly wonderful. Enjoyed your post. Welcome, Nancy

Yes, it definitely becomes easier. You might encounter an SA who might not want you to try on anything even if you are the only one there but do not allow those times to discourage you. Just move on and enjoy!!!

Hi, Angela, glad to read you have had such positive experiences in shopping. I’ve been building up my nerve about browsing in women’s departments. The first time I looked around in a thrift shop, I could hear a woman behind me say “OK …” . I made the assumption she was commenting on a man browsing ladies jeans and capris, but I don’t know for certain. Since then, I’ve tried to be less furtive, just try to “own it” as some express it on these forums, and browse naturally. I have not yet had the nerve to actually try things on and most of my shopping has been at Wal-Mart and Target where there are lots of people milling about anyway. I did buy some nice underwear at JC Penny, and the associates seemed to think nothing of it. It does become easier the more one does it. However, I’ve looked in the window of a local Dress Barn as I’ve passed by going to other stores, but have not yet gone in.

Hi Angelia, After that thing at Walmart a long time ago that I posed about, I find that whether in drag or drab, they just want your money and treat you well at Walmart, payless shoes, dress barn and any where you go is okay and dang the clothes you buy are yours and they help you buy it.

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Originally Posted by Amari

Hi Angela,
Big W, TS14, City Chic; it's obvious you're an aussie girl, what part of the country are in in?
City Chic is a favourite of mine, I love the designs of their dresses and lingerie.

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Hi, City Chic is my favourite as well. Have been in about 6 different shopping centres and the ladies were lovely in each. The clothes are oh so nice. I must have tried nearly everything!
I'm in Queensland.

Thanks all for the welcome and nice responses. I hope my story inpires others to go for it. I must agree with the 'pink fog' warnings though. Watch those dollars!

On Tuesday I ALMOST walked out of the shop wearing the dress I had just bought. It was so tempting. But then, when I got back to the car I decided to get femmed up for the drive home. I needed to stop for petrol on the way home and did it wearing a black dress, stockings, heels, bra (filled), and necklace. All with my man head sitting up top. hahaha I didn't care! The attendant and other customers gave some funny looks but nothing negative. Mostly smiles.

Wow, that is a great story on getting started shopping for yourself. I am not at all courageous enough to do it YET! I have said in other places that my SO is very supportive and as such she ends up buying most of my things. All of those things were undergarments and on a couple of occasions I have been with her. Of course nobody looks twice at a man and woman together buying lingerie and hosiery. Once or twice I have even bought hosiery by myself but I have never bought anything that was obviously for me anywhere other than online with one exception. She and I were at our local Walmart and we had been talking about buying me shoes before this. In fact, about a week before this we had been at DSW looking for shoes in my size and used a cover story with the SA about needing a pair for a young man in a theater production. I felt sure he saw through the story but he did a good job at not letting it show. And even talked about how they get a lot of men coming in to buy shoes and that the young man need not feel self-conscious about it. (I took this as him telling me it was okay to be accepting of who I am and what I like.) We however did not find anything in my size that we felt comfortable with. I broke my ankle in a motorcycle accident last year so high heels are out. But I digress, at the Walmart I was still too embarrassed to openly shop for women's clothing items for myself. So I was trying to figure out how to be sure if a pair of shoes I saw there would fit me. This tip may be helpful to others who are still unsteady about shopping publicly for themselves. I tried on a pair of men's shoes and checked the Mex size of them. I discovered that men's and women's shoes do not have different sizes in Mexican sizing. So a men's 28 is the same as a women's 28. So if you know your Mex size you can shop for most shoes very easily. Mind you, we do not live in an area with a large Hispanic population, so it would seem that Mex sizing on shoes is simply becoming more popular since almost all of the shoes had American and Mexican sizing, or American and European, and some had all three.

An update to my story.
As the weeks have gone the desire has grown to go dressed in public. I've wanted to walk out of the shops wearing clothes I've just bought but wasn't quite ready. Yesterday I did it!
In a major shopping centre I went into one particular shop and the lovely SA had me try on just about everything in the store. I fell in love with a skirt and top combo. I was already wearing a bra and carrying some lovely shoes with me, so I put them on while I paraded in the outfits in the big mirror outside the change rooms. I told the SA that I really wanted to walk out of the shop dressed up. She said "why not, just do it".
After about 5 minutes of nervous shaking it was time to bite the bullet. I purchased the items. She took the tags and made the sale and I walked out into the shopping centre faking confidence while inwardly terrified.

Here was this obvious man head sticking out of a skirt and top with prominent breasts. I wanted to rush back to the car but forced myself to keep window shopping. There were a few odd looks but no drama. I littls while later I walked past a shop that had wigs. Went in and tried a few on and bought the one that suited me best. Now I could walk around with a little more confidence. Still a man on close inspection but not so obvious now.

From here I thought "why not go the whole way?" and found a nail salon. Got some press on nails applied and painted a lovely red shade. Now we were cooking! Into a beauty shop then for some matching lippy. Hmmm, how am I going to apply this? That led to my first visit into that forbidden world of the female toilets. Standing there at the mirror applying the lippy with ladies washing up beside me. What an experience.

I then spent the next couple of hours in full female mode and didn't care who took a second look. So liberating and exhilarating.

The pink fog hit badly though. Spent hundreds of dollars to get the look, but the good thing is that I now have all I need so shouldn't need to shop much any more.

So glad to have met this side of myself.