Let myself get caught out for the experience of it.

[Diversity]

After reading so many posts where people have been caught out while shopping and more often than not nothing of any negative consequence occurred, I decided to build up my courage and experience what it would be like to be caught out. Sooooo....
I went shopping dressed in male mode, but underdressed with panties and bra, wearing girls jeans, a males button-down long sleeved shirt and natural-looking lipstick.
I went to the lingerie section and spent time trying to find a bra in my size, but to no avail. An older, bored-with-her -job, SA came over to me and asked if I needed assistance. I told her I wanted to buy this particular kind of bra (showed it to her) but couldn't find my size. I told her the size and after several minutes of looking without success, she went to the back where stock is kept and a shortly returned with two bras. I told her I'd take one and purchased it! She was polite, but never smiled or made any sort of negative remark. Just transacted the sale for which I thanked her and went on my way.😄
I then went to the cosmetic section and got into a conversation about moisturizers with a young and pleasant SA. I told her I have never really treated myself and now that I am retired, I wanted to 'come out' more and enjoy what women have been continually enjoying all their lives. She gave me a big smile and said she thought it was great what I was doing!
Ultimately, about $400.00 later, I purchased some great products for facial moisturizing and skin care. I thanked her and told her how perfectly she had made her lips and asked her how she did them. She said with a good lip liner and a very steady hand. She offered me her name and told me she worked nearly every day in this department and if I was interested in learning anything more to feel free to come back and she'd be glad to help me! She never made any negative comments about me wearing a bra, or asking about cosmetics, lipstick, lip liner, etc. for my use.
I left very happy, and wanted to post my experience, as so many others have done, because I gained the courage over years of reading everyone else's posts, to do this for myself. I hope that my post, may give someone else the courage (and joy) to experience what I experienced just the other day.
Good luck!
Di 😘

[jenn]

Thank you. That is a wonderful post. I shop for myself in drab all the time and rarely get any reactions at all.

[Diversity]

Thank you Jenn. I now believe this to be so, having experienced it for myself and am going to enjoy shopping so much more!!!
Di

[Nadine Spirit]

And just like that you taught yourself that it is just that easy! Good for you!

[Teresa]

Diversity,
It's so good to hear you had a nice time shopping.
You don't say how old you are but I was expecting more hostility as I get older but they appear to ignore it, so maybe I should too.

I had a similar experience with an older SA but I just kept chatting and eventually she came round then when a coworker appeared we had a bit of fun, her parting words were I wish my husband would buy me underwear, I looked across at the SA who had served me and smiled then suggested she told her who they were really for !

[Maria 60]

Nothing wrong with a happy story. Sounds like you had fun and it was great the hole story had nothing but positive. Good for you it most have taking a lot of courage. Steps forward, that's what it's all about.

[Robin414]

Great post Di, I love inspirational stories! It takes a lot of courage to 'come out' like that (been there, several times) but it takes soooo much weight off....like sooo much! 😀

Way to go Di!

[binair10]

If I get negative reactions when I shop in male mode, I cross that shop off my list. Plenty more to go to to see if I get a positive reaction.

Julie.

[MarciManseau]

Way to go, girlfriend :) Keep up the good work and I'm sure you'll have tons more great experiences.

[karen inside]

My favorite is wearing heels around the house (tile floors) and the cell phone rings. Of all my female friends that have called- only one asked me about the sound of heels they could hear while i was walking around the house...told them it was my "dress" shoes. I like being devilish...inherited it from my mum.

[mechamoose]

$400 dollars?

Yikes, were you buying Dior or something? (If so what was what? Two compacts and a couple of brushes?)

Maybe I'm just cheap, and wince at a $15 bottle of polish. That is extravagant, honey.

I'm sure you are worth every dime :)

- MM

[Beverley Sims]

I have been honestly shopping for years, I do pick the moments to do it though.

Why take unnecessary risks.

[Tina81]

Diversity,
I'm curious about your wearing a bra. I've worn a bra as well but it wasn't filled and worn a sweatshirt and coat so it was nearly impossible to tell I was wearing a bra. I've also thought going in drab with women's jean and pumps with breast forms/bra to Dress Barn. Wondering what kind of reaction I would get? Has anyone else ever done this?
Tina

[Diversity]

Yes it was Dior' Total Capture and a bottle of their follicle treatment. They are a birthday gift for my wife. Can't wait to give them to her. We have never splurged on this before but I wanted to see what it's like. As I know she'll share it with me 😄

- - - Updated - - -


I have been honestly shopping for years, I do pick the moments to do it though.

Why take unnecessary risks.

Hi Beverly,
I did it because of all the posts I have read, where people have said they had positive experiences. I wanted to take myself out of my comfort zone and see if I too, would have a positive experience as well. Also I enjoyed the thrill of it all! It was fun and I have gained a bit more confidence to do it again.

[CONSUELO]

As many here have said before, all you have to do is be polite and pleasant. The Sales Assistants just want to make a sale not a moral judgement.

[Stephanie47]

Happy for your pleasant experiences shopping. It should have gone as you expected. The only exception I have to your post is the lead, "Let myself get caught out for the experience of it." Getting caught always infer the person perceives some negativity to what they are doing. You could not have been "caught" because you were doing something that you felt was right. But, I know what you meant.

[Abbey11]

Hi Diversity, glad you had a great experience, sounds fun!

[Diversity]

Happy for your pleasant experiences shopping. It should have gone as you expected. The only exception I have to your post is the lead, "Let myself get caught out for the experience of it." Getting caught always infer the person perceives some negativity to what they are doing. You could not have been "caught" because you were doing something that you felt was right. But, I know what you meant.

Hi Stephanie,
What I meant by 'getting caught' was to know that I actually was speaking with, and buying from, a sales assistant who knew I was a man in women's underclothing. I got the opportunity to learn from experience what so many others have posted in the past - that for the most part the sales assistants do not make fun or embarrass you. They simply carry on with business as normal, and either let you know that they know you are a cross dresser or they don't acknowledge this at all. The challenge I am now overcoming is with the fear I had about being embarrassed in public. What I am finding is that the sales assistants appear to be more accepting of us, than I had thought.
Thank you for you comments. I appreciate you and everyone taking the time to reply.
😘
Di

- - - Updated - - -

Hi Tina,
In answer to your question, I wear a bra without any breastforms. Since my football days have long passed, my chest has softened over the years, and I wear it with a sense of pride and good memories, happy to let it be, as it really isn't too bad, in actual fact. What it does give me, naturally, is a full B cup, which is good enough for me.
So when I wear a bra under my shirt, the 'bumps' show. I wear a patterned shirt do they don't show too much when I go shopping in male mode.
Hope that answers your question about me wearing a bra on this excursion. 😁
Di

[lingerieLiz]

Since I wear a bra much of the time I can tell you that they will show from time to time. Never had much of a problem. I have worn C cups often although Bs don't show as much. One day I was going up on an escalator and noticed a woman looking and studying me. Then it dawned on me she could see the projection as I was wearing a c cup. Funny part was if she followed me we would have ended up in the lingerie dept. I don't wear forms and rarely wear chiclets. I often wear blouses and leave the top two buttons undone. From time to time I've bent over and people have seen the top of my bra. Under Tees and sweaters I wear foam cup bras as they give a smoother look. They also leave little to guess about.

[CarlaWestin]

Well, if you desire the exhilaration of being out dressed and caught, you need to change your look and venue. Try a little more endowment, flashier makeup and a miniskirt. Then go to a non retail establishment like, I don't know, an office building or something. SA's have a polite protocol to customer service and only mutter the word "freak" after you walk away.

[Janet Bern]

Tina
I usually wear my bra with forms, pantyhose and a slip under my regular clothes and go shopping
with a loose sweater or jacket no one knows I am underdressed. I go to Dress Barn and outlet stores
regularly and have had no problem at all. In fact I also go bra shopping at Soma, Maidenform and Bali outlets
Usually in their off hours ... mornings or around dinner time. Never had any problems

[Samantha981]

Thanks for sharing your trip! I've shopped for makeup in both full male mode but with nude lipstick or slightly underdressed with all male clothes, a bra and lipstick and mascara with a bit of eye shadow. Usually in that case looking for a help picking a single thing like lipstick or eyeliner, etc.
It always goes just fine, never made uncomfortable. If they ask who is it for (they usually don't) I'll say 'for me' (well a few times at first I didn't expect the question and chickened out and said for the SO - that's OK, part of the learning!). They just get down to business and help find a color that goes with my tones. If anything, I make sure to shop in male mode or underdressed off peak or away from home - more recognizable of course :heehee:
Samantha

[Diversity]

Actually yes, it was Dior! Their rose petal based skin care products are expensive, but in truth, they really do make a difference, and within s few days they cleared up a dry patch of skin I had between my eyebrows.
It was a big splurge for me, but I wanted to do it. As they say, you can't take it with you when you go!
Di

[Alice Torn]

And, i bet the SA like seeing a $400 ring up, too!

[Sophia143]

From my experience, sales people will at worst be put off a bit and a bit snippy. The vast majority of my shopping experiences en femme have been rather cordial when it comes to sales people. They are at work and most likely won't get weird with you. I've had some nice experiences while out shopping, just having conversations with sales people about anything. One cashier at Total Wine chatted me up for 20 minutes after I checked out, just to talk. Interestingly enough, I'm been substantially more nervous going shopping for feminine things when I'm in boy mode.

Good for you to have a new experience Diversity.

[ReineD]

SAs are wonderful especially when they make a sale!

We've had a few stories over the years of surly SAs not taking kindly to men using women's changing rooms, but I don't think this is the norm. One time though my SO walked into an Ann Taylor (or similar ... can't remember the exact store), with me following a few minutes later. I headed to a different section of the store than where my SO was. The SAs did not realize we were together and I caught then snickering and nodding towards my SO. We were the only ones in the store. I gave them a long, cold look and they stopped. No doubt if we had bought anything, they would have been nice as pie.

[Sophia143]

I did sales for a few years ReineD. One thing of many that I learned is you treat anyone who walks into your store as a sale even if they tell you they are just looking or have no interaction with you at all. You make a living in sales by selling, not driving away potential clients. Whoever you dealt with in your experience might want to seek another profession since driving potential customers off seems to be their forte, not good business. I'm sorry you and your SO had to deal with that.

[ReineD]

Thanks Sophia, my SO never noticed and I kept the incident to myself. I tend to look people in the eye a lot when we go out together, and so I catch more reactions than my SO does. Had I headed straight for my SO when I entered the store, I never would have seen the snickering and we would have been none the wiser.

I do need to say that virtually all SAs and wait staff we have dealt with have been professional. If they found humor in my SO's presentation they've had the good grace to not show it to us.