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The Lighter Side of Crossdressing Pt 3

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Posts: 101
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Topic starter
(@Anonymous 94145)
Estimable Member
Joined: 1 year ago

I know, I know - I did say in the previous post that it would be the last.

I guess I am like ( and sure we have all met) The “ I must just tell you this one last story” Sorry xx 

BUT…………………...

I used to work in the town centre, so at lunch times would often go for a wonder around the Record stores and shops. My lady knew this and therefore found me to be a handy foil for picking up stuff for her. Of course I did not mind at all. One of them was to go to the department store and she would say to me “ Can you get me some tights?” To which I would say “ Oh the Lycra mix 15 denier Nearly Blacks ?” Either yes or show me the packaging for another kind. The mission was set………….

I found things out about all this experience. One of them is that it did not bother me one bit if I was shopping for ladies things if it was for her. Secondly come to conclusion that the nerves I had when shopping for Ladies “Smalls” for myself was indeed self imposed. I mean what makes me so important that the cashiers would spend the day chatting about the time when a Man came in and bought a Bodyshaper and Garter Belt ? 

So all good, positive “who cares” frame of mind - Until…………….

I was in line getting her some Nearly Black stockings for her ( My Favourite colour as well ) and besides they might have even been for one of her sexy surprises. To be fair mind, she often wore stockings and it used to drive me mad and could never stop looking at her legs. I am sure she knew this and in some alluring Siren like trick managed to get me every time. We all like to look our best though don't we ?  

I digress - stood in line waiting, big queue and only one serving -  5 behind me. My turn to get served. The young cashier ( or at least my age - I was young once too) picks up the Stockings and says “ Oh are we having dress ups tonight ?” Great - everyone heard that and I was embarrassed, she did not mean any malice I know but you sometimes think if people can see if you are a dresser. Well I did anyway then.

I panic, and quickly say a resounding “NO” but not sounding convinced myself……...

I wish I could go back now to that exact time and be the person I am now who would answer the question she delivered by “ Yeah, can do - what time you coming round? “ 

Next week in the same store with a shopping list from my Lady , no meltdown and remember - everything is temporary. 

 

So, my lady and I and many friends used to Hike and climb ( big to us) mountains in the UK.

Proper gear was expensive then and she had a waterproof fleece that was ace but cost an arm and a leg. it fitted me as well. She was forever telling me to get it off and since we did not have much money, would have to wait until we could get one for me.

The time came when we could spare another arm and leg to get one for myself - went to the store ( 50 miles away was the nearest stockist - no online then ). Being very careful as to not get the same colour as hers, I found one my size and ambled over to the cashiers desk.

The shop was a cosy family run shop where they still spoke to you and heard conversation rather than “Beep - Beep”.

So the cashier was the Son of the owners. Mum and Dad were stood behind, observing him as he was being trained. Nice lad, chat, chat, chat - the parents giving nods and smiles in agreement of polite conversation.

Cashier :- "Oh they are great these are…."

My lady :- "Yeah - ( points at me) He keeps stealing mine and have to get it off him frequently”.

Me : ( Big Smile) "Yeah she’s always catching me wearing her stuff !"

I look up for the agreement and warm nodding of the parents as to the quality of my joke but all I got was Mum shoegazing and Dad looking embarrassed. At least the Son got it and laughed! 

Might have touched a nerve - as you know, we are not the only ones.

As an epilogue to the stories - I am fine when I shop for girls things now. Sometimes though, even now get a meltdown when there are people stood next to or in front of what I want to look at and I just walk out the shop and invariably go back in later. 

When you think about though. It’s only like when you are in the supermarket and someone either stands or plonks the trolley in front of the Frosted Flakes you wanted.

The same thing 

Jillian x

 

 

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7 Replies
Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@justjillian Don't worry about any story being your last. I will keep reading them. Things change, so there will always be one more story. That's one reason that I will keep posting stories. Somebody may learn or benefit from them in the same way I learn from your stories.

Nothing is more constant than change. We just have to be willing to change, too.

I am slowly changing by being more bold, more confident, more experimental. I want to get better, so change is necessary to get there. Having been in retail sales for quite a few years, handling my retail buys shouldn't be a problem. For the most part, I am cool buying in person, but I know that I can do better. Being self-conscious at the cash register can be daunting, but we survive long enough to go home, get dressed in what we bought and look in the mirror. That's a win.

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette - Yes I think we take ourselves too seriously and although we may not know it. The “Condition” we have is harmless. Compared to what I get up to when I am riding a motorcycle and don’t even give it a second thought. Dressing is a pretty tame pastime in the whole scheme of things.

I guess we all need acceptance , not only from others but from ourselves. I personally am so much happier since I had a chat with myself and this site is really Heaven …………

Jillian xx

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(@bianca)
Joined: 8 years ago

Noble Member     GB
Posts: 1264

@justjillian Thanks for sharing your story Jillian. Been there in both instances. 
When I first started I was totally paranoid. Hid stuff under a newspaper and used self service tills whenever they were available. Waited until Valentines Day or Christmas to buy stuff like lingerie, under the cover of

‘it’s a gift’😂

Now I am totally up front and open, sometimes even willing the cashier to ask me, wanting to tell them it’s for me. 

Last time I bought a bra I was disappointed to be served by a male as I wanted to ask about a little hook on the back of one of the straps. I later searched online and it turns out the little hook is to hook the shoulder straps together at the back, turning it into a racer back bra, great  for halter neck tops/dresses. Every days a school day, especially when womenswear is concerned!

 

B x

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Baroness
(@river)
Joined: 1 year ago

Noble Member     New Hampshire, United States of America
Posts: 827

@justjillian If you stop posting stories what the heck will we read and have to comment on 😉 Only time I ever bought anything out is at Halloween.  so I dont have any reciprocal stories on this except even then buying a wig or something I would barely look the cashier in the eyes and  looking all around like I stole something. ill say Im surprised when people at checkout would make any comments though.  one would think that would be greatly frowned upon by management as its bad for buisness.  but human nature I guess.  Oh and years ago they had these boobs in spencer gifts that were for a guy they hung on the wall and bounced and danced to music like one of those billy Bass things. not sure if this is in the UK. but they looked and felt pretty real and were natural size so this was "my first boobs" even then this was intended for men I was embarrassed as I had other plans for it.  lets just say I never put batteries in them and they never made the wall  🙂  Cheers RC

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@river The Boobs thing is great ! I would have probably put the batteries in as I am a kind of “what’s this button do?” Guy.

I would have done the same thing with them as you and if I had such imagination but sadly never saw them over here lol.

In the UK folk are a little more familiar, guess it’s because we are an island race and it was pretty common for the cashier to sometimes have a comment. Not so much these days mind you. As you pointed out it’s bad for commerce. I do miss the challenge though. I am sure that all of this anxious shopping is self imposed. The thing is now that I care less and have a snappy rejoinder waiting for if anything is said.

I was in a posh underwear shop once and bought some Fully Fashioned stockings and they were not cheap. The very friendly lady assistant says to me - they are a big size - is your partner tall like you ? - I knew what she was saying so just replied “ Yes, she even looks like me”

We laughed and she took the money - everyone was happy.

Thanks for reading and your encouragement 

Jillian xx

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Baroness
(@river)
Joined: 1 year ago

Noble Member     New Hampshire, United States of America
Posts: 827

@justjillian Oh I saw it work in the store many times lol. RC

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

Posted by: @Anonymous 94145

I used to work in the town centre, so at lunch times would often go for a wonder around the Record stores and shops. My lady knew this and therefore found me to be a handy foil for picking up stuff for her. Of course I did not mind at all. One of them was to go to the department store and she would say to me “ Can you get me some tights?” To which I would say “ Oh the Lycra mix 15 denier Nearly Blacks ?” Either yes or show me the packaging for another kind. The mission was set………….

If anyone needs some cover while shopping in drab for female clothing for yourself, create an illusion that sales clerks can easily accept and use to justify you being in a women's environment doing something a woman normally would do.

Carry a piece of paper, a list. Write down what you need and if a sales clerk asks if she can help, refer to the list as if you aren't sure of what you need and you don't want to make a mistake. Doing this should change the whole dynamic.

Nowadays, you can do it with a phone and have a picture of the real deal ready. There is no mistaking what we need, this way, since men are visual creatures, right?

 

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Posts: 1413
(@finallyfiona)
    Leighton Buzzard, Bedfordshire, United Kingdom
Joined: 1 year ago

I'd have happily come out with that 'wearing her stuff' one in the years before Fiona, self-deprecating and ironic at the same time, that should have worked a treat 🙂  But then I'd not have twigged why the parents' reaction.  

Just been to Tesco for some makeup remover wipes.  No problem, even picking various packs up and having a close look to check they do waterproof, and check the ingredients etc.  I would have loved a browse through the cosmetics stand at the end of the aisle, but didn't feel I could do that ... yet 🙂  Those things are also security tagged so even the self-service till isn't self-service any more.

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Posts: 101
Guest
Topic starter
(@Anonymous 94145)
Estimable Member
Joined: 1 year ago

Thanks Fiona - Yes self service is great but do admit today after buying some false nails again (they were on offer) I went to the self serve and there were two young girl assistants standing to help. I thought to myself, please please PLEASE go through smoothly without needing the girl to tag it through. All good,  went through okay but still have wobbles even though I have been shopping for years 

Jillian xx

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Posts: 139
Lady
(@butteryeffect)
Reputable Member     Preston, Lancashire, United Kingdom
Joined: 2 years ago

It is just what goes on in our heads, I find I can buy make up and women's clothes in December because I tell myself that people will assume I am buying Christmas presents. I probably couldn't do it in much of the rest of the year though. Not that anyone cares either way

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Posts: 101
Guest
Topic starter
(@Anonymous 94145)
Estimable Member
Joined: 1 year ago

yep - know the xmas shopping excitement, not because it was seasonal but for the self indulgent “get the stuff I have been eying for ages” trip.

Its not so bad now and they really don't care and even if they did - Who cares anyway x

Jillian x

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Posts: 3273
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 4 years ago

It was always a barrier with myself back in the day as men only bought towards Christmas and maybe a birthday. I don't think anything surprises the new generation.

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@ab123 Agree completely, it has certainly got easier. Maybe if it goes to normal ( like I am when I buy a can of WD40 or something) . I have to admit though, although it’s sometimes stressful, it’s always a buzz when I have actually plucked up the courage to take them to the cashier. Maybe I will miss that - who knows ?

Love Jillian xx

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Hostess
(@ab123)
Joined: 4 years ago

Illustrious Member     Surrey, United Kingdom
Posts: 3273

@justjillian It's all a learning curve and you'll get used to it. Unrelated to this a crossdresser who was in their seventies was in drab going through airport security. Stopped for a routine check the lady guard asked for his I.D. and on seeing the age was amazed saying he looked 20 years younger, 'You should see me in my makeup' he said as he took back the I.D. and left.....

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@ab123 - I am looking forward to being so bold, I guess the embryonic stages of this was per my joke in the shop. Cannot wait x

Thanks as always 

Jillian xx

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Posts: 873
Lady
(@mary)
Noble Member     Sydney, New South Wales, Australia
Joined: 4 years ago

I was trying on a pair of sandals and copped a glare from another lady.

I said my wife's feet are 1 size smaller than mine. And if they are a little tight on me, they fit her. 

She (Indian origin) said why doesn't she buy her own. I replied she is helping her family clean and pack up all the Christmas stuff and can't make the sale. But I can.

Oh she said. Wish my husband would be so considerate. 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@mary Oh cracking answer - I might use that one

Thanks

Love Jillian xx

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Posts: 81
Lady
(@sarahl)
Estimable Member     Kalamazoo , Michigan, United States of America
Joined: 2 years ago

When I first started buying wemens clothes 7 years ago I would hurriedly make a selection if I was by myself.  If my wife was with me I would ask if she thought my niece would like it. She knows it's for me. I would say that for anyone else that was paying attention to me. Now I don't care. I freely and calmly shop for whatever I want wherever I want. I never use self check. I don't work there.

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@sarahl 

I am certainly getting better and less worried over what may be thought ( as I alluded to - what makes me so special?) .

I just need to be a little more patient with myself and stop having these silly doubts and wobbles 

Thanks for reading

Jillian xx

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Posts: 1287
Ambassador
(@leonara)
Noble Member     Long Island,, New York, United States of America
Joined: 9 years ago

How buying women’s clothes have evolved over the years… I was the Christmas and birthday dad who bought in the store (way before online buying ) dresses, sweaters, and tops so mommy would have presents under the tree and a package to open on her birthday… Fast forward.. my wife and I are empty nesters now and we exchange gifts for one another. Since I am a “serious” CD… Christmas now affords the opportunity to for me to buy in drab) for Leonara as well’s my wife… my wife a petite 8 and I a woman’s 10… invariably the sales associate would mention that there are different sizes…. I nonchalantly say “I Know” lol hmm let the SA guess.    My New Year’s resolution will be Leonara will shop en femme hmm let the SA guess then.. thanks for listening..

Happy New Year ladies.   Leonara 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@leonara 

Get it completely and will say yes if asked “its for me” but no one is really bothered are they, its only our inner self that feels that we are not being complicit with society.

Not sure about shopping fully dressed, not even at the stage where I will walk around the block yet. That is not at the forefront of my desire ( just as well as I know I will struggle in 4 inch heels )

Thanks for reading

Jillian xx

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Ambassador
(@leonara)
Joined: 9 years ago

Noble Member     Long Island,, New York, United States of America
Posts: 1287

Shopping fully dressed and your walk around the block can be on our bucket list… its nice to think about it lol Leonara xo

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Posts: 14
(@alwayshave)
Eminent Member     Hastings, East Sussex, United Kingdom
Joined: 1 year ago

About 2019, I was buying 4 items shapewear in a sale – in a store where you queue with your items then get called forward, also in this store they always shake each item out and fold properly, so we’re all going to get a good look at each item – and that the few seconds I don’t like.  So, stand in queue and see four clerks; I think please not either of the very cool looking 25 y/o dudes, please not the really attractive young lady, pref the older clerk with grey hair.    

I got the one of the 25 year olds – so four underwear items all laid out waiting to be folded, we all know what they are and then the till system goes down – 10 minutes – nothing else to do but stare at items until system let me pay for them. Joy.

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@alwayshave Oh gosh,that sounds just like the thing that would happen to me and would be my worst nightmare. But hey with experience comes wisdom. Never worked in retail so have often wondered if they actually notice what they are selling as might be just another commodity.

Thanks for reading and commenting

Jillian xx

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

Posted by: @Anonymous 94145

@alwayshave have often wondered if they actually notice what they are selling as might be just another commodity.

Oh, we looked, but it would depend on circumstances.

I worked in a sporting goods store in which we had one customer come in a buy a whole bunch of swimming caps at a time. We never figured out why he did this. We weren't sure that we wanted to know, either. 🤪

 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette Oh that’s good to know. You got me thinking of the swimming caps now ! An innocent one would be the purchase of Sock Stockings ( or Pop Socks as we call them over here) excellent boot liners when Hiking and so facilitated wearing socks overneath them would prevent blisters - Used to buy them all the time with no worry’s 🙂

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@justjillian Pop socks

Translation: ankle-high, up to knee-high, stockings.

Sounds practical.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@alwayshave Murphy's Law in action. 😬

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Posts: 2022
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Like most I used to be nervous when shopping for ladies items (clothes, lingerie and the worst pads). Over time I have gotten to where I don't care. I now buy whatever my wife or I need and don't worry. 

XOXO
Suzanne

PS - please keep your stories coming - they are a joy to read and do stimulate conversation

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@cdsue Thank you for the kind encouragement - its appreciated XX

Love Jillian xx

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Posts: 55
(@wend77)
Trusted Member     isle of wight, Isle of Wight, United Kingdom
Joined: 4 years ago

Hi Jillian 

to me the feeling of buying womens clothes etc was a bit tense when i was young even though i used to buy my girlfriend (now my wife ) tights regularly,  as time went on you get use to things, and even though my wife is on board with my dressing i find buying bras, panties etc not too bad, when we are both together i will look and investigate underwear etc before we buy. so even though i look around to see if there is anyone o know istill purchase what i want, do you still play the guitar ?

Love your stories

Wendy

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Posts: 1413
(@finallyfiona)
    Leighton Buzzard, Bedfordshire, United Kingdom
Joined: 1 year ago

Seeing this thread again reminds me, I was in a charity shop in male mode with the OH on Saturday.  At the bottom of the window display they had these purple leather high-heel boots, must have come well over the knee if not right up the thigh 😮  On the way out she pointed them out to me (I do wonder if she suspects, you know 🙂 ) and one of the other male customers reacted too.  Straight away, I turned to him and with a grin said 'If those are an 11, I'm sold!'.  Of course what I should have said was, 'Tempting, I've got the perfect skirt to go with those!'.  I just love how the truth makes the irony stronger, even if no-one else knows it 🙂

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Posts: 101
Guest
(@Anonymous 94145)
Estimable Member
Joined: 1 year ago

I was in line at Payless and the store was almost totally empty except the customer in line in front of me- who I can see is a CD in full girl mode. The 2 salespeople make a few  insensitive jokes about the pumps she is buying and she pays and leaves. Now it’s my turn and I put my red pumps on the counter to pay and the sales clerk announces to the other sales person who has walked away- I need you to check the price of these red pumps for this customer, as he holds them up in the air and laughs. I tell him the price is on the box. After I pay and leave, the CD is waiting outside and we have a nice chat, and she invites me an NYC CD meeting the next week! I attended and had a lovely time.

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11 Replies
Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@chanel Its not nice that they make jokes and sure that no harm is intended, I guess its the real meaning of ignorance. They are not to know but its still a downer when you are the subject.

Sometimes though nice things happen like your chat and invite to the meeting.

Stronger together and this is why this site has been so much of a help as everyone has the same issues. 

I just always try and see the bright side.

Thanks for reading

Love Jillian X

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@justjillian I was only slightly embarrassed because I knew the store was basically empty. It did seem unnecessary to have a laugh at my expense- but, I didn’t care. I just wanted to get those red pumps home to try them on!!

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@chanel Yes its the thrill of the chase really I think. I am always elated when I leave the shop after my self imposed “ordeal” 

It's not always bad eh? ( almost never in my experience x) 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@justjillian Well said! The excitement we feel when we first step into the store en femme….love it!

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@chanel So, I am curious. What made the other CD think to wait for you outside of the store? What was the "tell"?

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette As I  walked out of the store, she said Hello and said she noticed that I bought a pair of heels, and asked me directly if I was a crossdresser. I said I was and we talked for a little while. We laughed about always going to that Payless Shoes location because it was always empty. Unfortunately, It closed within a year from our meeting!

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@chanel Thanks. I thought that it would be something like that.

We used to have a Payless store near us, too, but they pulled out of Canada years ago after their second bankruptcy. Nowadays, we have The Shoe Company chain nearby which was bought out by DSW.

However, my first high heels were a Payless pair of size 15 that I found in a nice thrift store. The only time that I ever wore them outside, in a mall, a young sales clerk asked me, "Are those from Payless?" I was flabbergasted how she knew. She said that her mother had had a pair. Small world or what?

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette That's wonderful! What did you say?

Also, have you tried DSW? There is a new one near me and I am curious- but it might be too close to home for safety. Let me know if it’s worth trying.

 

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

@chanel The closest DSW to us is not all that close, but I know where to find it and have bought from it once. It is a pretty large store, in my mind.

The Shoe Company is closer to me and I try to support it when I can. I need wide shoes, though, so the smaller store is a problem.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

Posted by: @Anonymous 94145

@harriette That's wonderful! What did you say?

I don't remember exactly, but we did discuss "things". After all, it was obvious that I was a tall male wearing 4" heels in public. 😁

Also, forgetful me, I got distracted and left my cell phone on their couch when I left the store and went walking around the neighbourhood. I had to go back to retrieve it and deal with them again.

 

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Guest
(@Anonymous 94145)
Joined: 1 year ago

Estimable Member
Posts: 101

@harriette oh my! I hope overall it was a positive experience. At least you looked good in your heels!!

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