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Dear Friends,
What was your first purchase in person? I’m sure we were all nervous and fearful during our first purchase. Wary of stares and dreading the inevitable interaction with the cashier at the end.
Was there a exceptionally helpful salesperson whom helped you? Was it a success on the first try or did it take several tries?
What was your last in purchase purchase? Lets reminisce and celebrate how far we have come.
Nostalgically and with all support,
The Bluest BelladonnaThank you Belladonna, for this topic.
I have already shared some of my expriences in the last 48 hours, so I’ll stick to the first and the last.
The first was horrible for me, but actually quite uneventful. After passing through the isle nervously for at least 5 times, I quickly snatched up the package of panties and put them in my cart, moving away to ‘safety’ fast. At the cash register, I just put the panties (bright pink, in a box but very recognizable as ladies underwear) on the conveyor belt and tried very hard not to look at the cashier, while having a heartbeat of 180 and sweat trickling down my spine. She scanned it and said nothing, didn’t look at me, and that was that.
Today – dressed in drab – I bought a make-up set, a make-up brush and a black dress. Very visible, very obviously for my use. Next to me there was an elderly couple that gasped and looked at me very surprised and so did the cashier. And I just looked at her, smiled, told her “debit card please” and put the items in my bag, slowly and deliberately. That really felt like a triumph… although my heart was still racing like crazy… I’m not Supergirl afterall 😉
Hi Belladonna,
My first fem purchase was over 50 years ago. I decided to purchase a bra and panty as I had outgrown my moms. So I rode the subway to the city and went to the bargain basement. It was so crowded that no one cared about a teenaged lad buying feminine underwear. Sure I was nervous but I was in and out as the line moved quickly past the cashier.
Alice
It’s so long ago, circa 40 years, so it’s hard to pin down just one purchase.But it would have been a bra and pants set from either a “value” chain store like K Mart or a small independent lingerie shop. I also remember buying an open bottom girdle from a Woolworths store in Sydney.
I used to do work interstate travel, so I would buy the above before I left and dump it before I got home. “My how times have changed”
Back then, quite a lot of lingerie was made here in Australia and for the sentiment of it, I still have two bras than were made here. A white “Hickory” in 16B, which of course does not fit me anymore and a “Warner’s Richness” in 16D, which would fit with an extender, but hey I have so many more lovely younger bras, why bother with the “oldies”
These days I buy what ever I want and keep 90% of it and have no qualms about doing so in person, (preferably en femme after a bra fitting)..
Happy dressing
Caty.
PS Back then and still now we had/have a bra brand, “Hestia”… Short for “Holds every size t…..t in Australia”.
My first in person shopping experience (as Sophie) was with Glamour Boutique in Fairfield, NJ. I scheduled an appt to try some things on. The whole shopping experience was perfect. The staff there was amazingly helpful and made me feel completely at ease.
I have since made a second shopping trip there and it was even more perfect than the first.
If you are in North Jersey/the greater NYC area, I would highly recommend Glamour Boutique.
Sophie
I use to live down in south floridah. We had a place named “Secrets in Lace”, which has since moved on. They catered to cross dressers, strippers and anybody else that was in to pornography or some kinky stuff. I bought my first baby doll and foam breast there. I went back several times. Once was a lady working, once a guy (the owner I think, but was nice) and the last time was a tranny. They were all really nice and let you try on stuff as well. They spent time with you. Most of the other shops in town were your standard porn shops with toys and dvds for sale or rent.
Lisa
Belladonna,
I don’t remember exactly when it was, probably when I was around 19 or 20. My first purchase was a pair of pantyhose at a drugstore. I can’t remember any specific details, but I’m quite sure I was terrified that everyone in the store, even those who hadn’t even seen me, were aware that I was buying them.
Most recently, I bought some new panties at Kohl’s. There wasn’t as much “cloak & dagger” behavior in my actions, but I still (50 years later) had a slight case of butterflies in my stomach, although I had done it many times.
In between, my most memorable shopping experience was at an Ulta store. perhaps 3 years ago, I was surreptitiously browsing for a lipstick that very closely matched my natural lip tone. A sales associate asked whether she could help me find anything. I told her I was looking for a light shade and sheen of lipstick, not specifically stating it was for me. She spent ten minutes, or so, leading me around the store, swiping and comparing different tubes of various brands on the back of my hand. I had let her know by then that it was for me. When I thought we had found the perfect one, she even asked if I wanted “try it on”. Talk about heaven.
My first in person purchase was a package of panties when I was in college.
the last purchase was two bras.Two memorable purchases were shoes. My first pair were a used size 15 with 4″ heels. Still one of my most comfortable shoes. The cashier had attitude, but I went through the line and purchase unscathed.
Soon after, the next pair I bought in Nordstrom, with no real plan except to try on shoes and get fitted. By chance, the sales clerk was very helpful and supportive. Getting the fit right, getting the shoe right. I found out that Nordstrom was supposed to be inclusive. Some staff were more inclusive than others, but I thought Vicky was amazing. Nordstrom evacuated from Canada, though, a few months ago. 🥴
Otherwise, I don’t get bothered about shopping in person anymore. The clerk’s either want my money and are willing to do what it takes to earn it respectfully or they don’t. Not my problem.
My first purchase was at a Fredericks of Hollywood. I was walking past the store in the mall and noticed a lovely red bustier in the window. I decided at the spur of the moment to go in the store and tell the SA I wanted to buy it for my girlfriend. (It was close to valentines day). The young lady who waited on me asked if I knew what size she was? I replied that she was about the same size as me. She then said “Honey is it for you?” I replied “You caught me.” Was so embarrassed. She then offered to measure me to find the right size. She was so nice. I ended up buying the bustier and some fishnet stockings. It was a wonderful experience!
For any new crossdressers, you can learn from this example, so that you don’t place yourself in the same position.
Make an accurate and useful list of your relevant body measurements before going shopping in person and use a small, cloth measuring tape to see if something that you are interested in is in the ballpark or not. It will save you trips to fitting rooms or having to return items after trying them at home.
Dear Harriette,
I wish I received this advice as a young crossdresser. I ended up with “tie up” bras and “stretch panties” because I had no concept of lingerie sizes.
The worst case scenario was I didint answer, froze and walked off in embarrassment. I soon figured out some key sizes and the endeavors were slightly smoother.
Thankful for the guidance, with a warm heart
The Bluest BelladonnaI quickly learned that I needed sizing info at hand, Belladonna, if I was going to even consider buying something marked in arbitrary sizes. What really does a size 9 mean?
Whip out your measuring tape and compare it to your notes. Update your notes if you find a discrepancy. I carry mine around on a hard card in my day bag and can figure out most items in less than a minute.
The hardest part of fitting something without trying items on, so far, is dealing with unforgiving, non-stretchy material – dresses that you have to put on over your head, shoulder and long sleeve widths, and waists that don’t match a male shape. Just try getting these things right while ordering on-line. I can easily nail most waist sizes now, but finding long enough inseams is more of a supply problem, not measuring.
My first in store purchases were in guy mode with my wife. She was so supportive and I was such a jerk, mainly because the nerves! So quiet and standoffish…we kind of stopped those outings because it was not fun for either of us. Damn I should apologize to her again right now!
My first solo in store purchase was at dress barn in guy mode, many years later. I felt compelled to concoct this elaborate story about how I was shopping for my wife because we were going away for our anniversary; what a waste of mental energy!!
Over the last three years I have gotten “comfortable” (within limits) shopping in girl mode. I live in the northeast, and the places I go the SAs do not care. Generally they want to help and of course are looking to make a sale. I try to get a sense of flow and attitude within two minutes when I walk into a store. I also tend to pick smaller stores where it is women only and no kids. If the SA greets me warmly I will stay and usually say “just looking” then get comfortable, then ask questions. It is such a rush to try on clothes in girl mode and get feedback from the SAs!!
Also yesterday I was traveling and stopped in a lingerie store in Vermont in guy mode (recommended by someone on this site). The owner was amazing!! Told her what I was looking for, she asked if it was for me, gave me what I asked for and another item she recommended, and let me use the fitting room! Simply amazing, and I never would have found the place without the recommendation from here!
Valerie
Dear Valerie,
The first few times are naturally very nerve racking. The shame and embarrassments hits hard even before entering the store. Im glad your overcome the initial fear; blooming with confidence! The rush of the experience is breathtaking too!
If possible, after you apologies to your wife. Please thank her on behalf of all crossdressers, as her support and care for you has build a better world for all crossdressers.
Thankful and blessed,
The Bluest Belladonna
I do not remember exactly because I used to buy nice lingerie for my wife ever since we started dating, so I was often buying lingerie. At some point, I bought something for myself, but do not remember when or what it was. Sometimes I would buy something for her, other times for.myself, so it all blended together.
I do remember the first time I openly bought something for myself and got fitted for it. It was at VS. I was looking at bras and the SA asked what size she was and I said it was for me and I didn’t know my size. She chuckled a little and thought I was kidding, but soon recovered and said she would get someone who could help me. Soon a very helpful SA ushered me into a dressing room did a measurement and I was soon trying on bras. It was a blast and she handed me over to another SA who was also wonderful. After I had settled on a bra we were soon back on the sales floor picking matching panties in front of all the other customers.
Dear JJ,
What a wonderful encouraging story! A great and helpful sales assistant makes all the difference for the first experience.
Thankful and blessed,
The Bluest Belladonna
As for my latest purchase, I bought a cute tee shirt a few weeks ago off the discount rack at a mountaineering store. I didn’t try it on since I knew my size.
The last time I tried anything on was at a Columbia Sportswear store and I tried on a dress with no issues and bought it and a similar one a size smaller for my wife. At check out, the cashier asked if I realized they were different sizes and I just replied that I did and left it for her to figure out why I was buying different sizes.
My first in-person purchase was in drab. I was in Las Vegas with my sisters, and they helped me pick out a souvenir outfit. A top that said “Las Vegas” across the chest and a pair of pink pants. My first en femme purchase was less than a month later. I bought a dress at Macy’s. I tried it on in the dressing room to see if it would fit me. You can see me wearing that dress in a photo that I will post on August 18.
After consulting the wayback machine, pretty sure it was pantyhose. I call it the “lurking” era. That expanded to lingerie and some clothes “for my wife” but always paying in cash to hide the purchase.
Fast forward 40 years, the first time I did a full en femme shop I ventured into a Dress Barn and the salespeople couldn’t have been more helpful and accepting. They explained what styles would work best and would check on me in the fitting room and bring more dresses to try on.
It was such a pleasant experience and I could pay with a credit card!
I did end up at a cash machine but only to get enough to go back and give the SAs a big tip.
The first time is so much easier now with self-checkout available in many stores, no need to look at a cashier or wonder what they’re thinking! And we have the option of buying online with no one having a clue what you’re buying or who it’s for.
But my first time was about 45 years ago, buying a package of nylon panties in Walmart. I was so nervous, shopping late at night when I was least likely to run into anyone I knew. And I would wait until there was a cashier with no line so I could check out as quickly as possible with as little interaction as possible.
Although these days I buy most of my clothing online, I still enjoy shopping in person when I can. My most recent purchase online was a Playtex bra in a different color than I already had. My most recent in-person purchase was a full-length nylon slip at a local dry goods store near my home that sells a little of everything and has a pretty good selection of clothing for men and women, including lingerie.
My first in person purchases were a skirt and blouse. I didn’t know my size so guessed at it and got pretty close. When I came out to my wife and started dressing again a few years ago I started in person shopping. My first purchase was panties at Wal Mart. I picked out a size and style and went thru the check out to pay cash. I didn’t get any looks or anything. Since then I have purchased other lingerie, a skirt, blouses and shoes. Some by myself, others with my wife helping. I haven’t tried on any clothes in the store but have tried on shoes. I have also started shopping at thrift stores.
XOXO
SuzanneMy very first purchase was pantyhose and yes I was super nervous and very young at that time. My first purchase of femme clothes was many years later as I started to want more. Then the first time I came clean to the sales associate that I was shopping g for myself was just after I came out to my wife. It was a great experience as she was super happy to help and super happy I told her my secret. Now a days I shop while in male mode , presenting as a male but dressed in all women’s clothes and fully dressed.
My first in person purchase was pantyhose and I was super nervous/scared. I went to the store with a list of things to get. And walked down the isle saw my size and it and put it in my cart I under my other things as fast as it could. Thank goodness for self checkout though I definitely was too nervous to go to the regular checkout.
As for my most recent purchase jau some nail polish.
My first time was in a lingerie store near my house. For several years I walked in front of it and admired the beautiful clothes until one day I got the courage and money to come in. A Lady helped me look for a sexy corset. I don’t know how I had the will to ask her if I could try it on. I was so nervous and excited. The Lady got a bit uncomfortable and she called another woman. The latter was so nice! She let me try it on and even asked me if it was the right size while I was in the fitting room. Of course I bought it and thanked so much the other Lady. It’s a shame I lost that corset in one of my several purges of youth.
I started buying my own wardrobe just a couple of years ago after i found CDH. Growing up I only had brothers, so the the only opportunities for trying things on were my mom’s and grandma’s clothes. I married young and would try on my wife’s clothes when I had the chance, but most things didn’t fit well. After finding CDH I got uo the nerve to go to Walmart and bought some tights. Just grabbed a pair off the rack and headed to the self check line. Rushed home to find they were too small. Went back and found a larger size but didn’t want to face the return counter, so the first set went to Goodwill. I have bought many things since, online and in person. Last purchase was a Torrid front closure t shirt bra. Tried on a couple to find something I liked, brought my forms with me. SA was very helpful. It’s been quite the journey the last two years.
I had two purchases that stood out in my mind. The first was the purchase of some tights at a department store. I of course knew my size. As I checked out, the SA commented on how unusual it was for a man to know what size hose to purchase for his wife. HA!
The second was also a hosiery purchase. I bought some thigh highs, again in a size appropriate for me. The SA paused to ask if I was sure about the size (jeez, I’m not that big!!) and I said yes I am sure. Suddenly it dawned on her that these were for me. She asked me to wait a second, dashed back into the supply room and came out with a pair of garter hose….basically a wide lace waist band attached to thigh highs. They were super cute. She explained that these were returned by someone who had opened the package and realized they were the wrong size. She offered them to me for free since they couldn’t sell the opened merchandise. I thought that was sweet of her.
Answering this question goes back to my origin story involving Christine 1.0. Wanting panties similar to the pink, white, powder blue and white nylon ones she frequently and accidently gave everyone a glimpse of back in school I happened to find them in the local 5 and 10 store in town. I didn’t know whether they were exactly the brand she wore but in my post-pubescent mind they were close enough. As for acquiring them, well when I was asked I just said I was buying a gift for my sister, and as I had 5 sisters that was apparently enough of an excuse.
Christine
…and even today, despite the fact that I had long since purged the original set of Christine 1.0 inspired nylon panties, I own a more recently acquired set in my current size in the same colors since the only other way I remember her is with my copy of my high school yearbook from the year I graduated in 1982 and the pictures therein.
Christine
One of my earlier purchases was pantyhose, press on nails, and fake eyelashes from a drugstore. I remember putting a box of Kotex in the basket in case anyone looked at what I was buying they would think “he must be buying for his wife”. Like anyone even cared!!
another time I was away for a night and taking the opportunity to get en femme. I forgot to pack my makeup bag, so I went to the drugstore and bought all the basics. The cashier said “what a good husband that you know everything your wife uses!” I replied “yes I am” in my best straight face
My first purchase was from a small specialist lingerie store in a small North West Town in the UK. I bought a beautiful set in white satin, throughout the purchaser my heart was racing and I’m sure the lady behind the counter didn’t believe it was for my ‘girlfriend’ but I completed the purchase and loved wearing the outfit.
While my first purchases were probably pantyhose, I can’t remember anything specific.
After a hair appointment, I stopped into Kohl’s in the same shopping center and saw a nice black skirt on the clearance rack. I thought about it for a bit, but passed. But as the day went on, I really liked that skirt. The next day I drove back to the same Kohl’s and bought the skirt, which I still have to this day. It is a knee length circle skirt with an elastic waist. It is now getting a bit loose on me (I recently lost a lot of weight due to illness), but if I take it in at the waistband I should be able to get more use out of it. I was nervous bringing it to the cashier, but it was really uneventful, either from the cashier or the customers on line.
My last purchase just happens to be from the same Kohl’s. Just last week I stopped in just to see if anything caught my eye. I wasn’t expecting anything, but found an above-the-knee black skort on clearance. It was a tad big (they didn’t have any smaller sizes) but having a string at the waistband means I can pull it in tighter to make it fit. I had no issues and no anxiety bringing it up to the cashier. She even gave me a discount when I told her I wasn’t interested in signing up for emails from them (I don’t shop there often enough, and when I do it’s more often at the clearance racks anyway).
My first in-person purchase was when I was 24 years old and in the Army at training course at Fort McClellan, AL. I ended up buying two Playtex bras at a mini post exchange one afternoon. I bought two because I thought I would give myself away by just buying one. I was absolutely terrified that someone would question what I was doing, but no one seemed notice, or if they did they they certainly didn’t say anything.
I remember it almost perfectly. It was in 1968 and I bought a white lace slip and matching panties from every girl in England’s go to underwear store, Marks & Spencer. As an aside I doubt there is one woman in England who doesn’t have at least one item in their underwear drawer from M&S. The slip was sort of empire line and only came to about 2 inches above the knee. It was the 1960’s and at the time mini skirts were all the rage. The shop assistant who helped me with the purchase was a young girl, probably about 18 and I remember she was so kind and put me at my ease, at least somewhat. My next purchase was in a local specialist lingerie store and I bought a lace (I was very into lace) bra/pantie/suspender belt (garter belt) set in a sort of pinky nude colour. With both purchases I was reasonably lucky about sizing but it may have been that the shop assistants deliberately chose sizes that would fit me. I was young and slim in those days and I’m pretty sure that in both cases I bought a 36B bra which fitted pretty well. Ah those were the days. Was I nervous? I was petrified!
I remember my first in person purchase like it was yesterday.
I had started university, and received a student loan. I thought the loan was free money (it isn’t); I was starting to get too big for my mom’s stuff, and I was getting bored with her clothing as she barely buys any. This was when internet for home was super expensive (like 2400 baud was the fastest), so I had no way to research sizing at all. Nor was my parents going to spring for internet access. Size was based off of what fit me from my mom’s closet, and maybe go up a size or 2 from there.
I had my own car so I drove out to kmart, knowing there would be no SA around. This was perfect, as I just wanted to browse at my leisure without any SA coming around and asking if I needed help.
I wound up buying quite abit of stuff, swimwear, body suit shapewear, spandex aerobic wear w/ spandex leggings, … all considered vintage now.
Hardest part was going up to the till to pay. I thought browsing around the women’s section was nerve wracking enough, it hit me when I had to go up in person to pay for all my goodies. I was starting to sweat, and at the end I asked if they had a gift box. I paid for my loot, said thanks, she gave me my gift box, and out I went.
I honestly can’t remember the last item of clothing I bought in store; maybe it was a swimsuit in a sporting goods store ? I usually buy my stuff online now.
Great thread!
My first purchase was a pair of black pumps at Payless. I was shaking like crazy until the SA said enjoy your purchase!
The most memorable was at Torrid 2 years ago ( in drab) and the SA asked if I wanted to try on the dress I selected. Of course I said yes! Definitely, my go to store now!
My first in person purchase was at DSW. I had just begun to actively CD, about two years ago now. I was there in drab, and of course I had to window shop over in the ladies section. I saw a pair of block heel sandals by CL on sale, and as Flip Wilson’s Geraldine used to say I owed myself a try on. There were a few people in the store, but I took them to the back and tried them on, walked about a bit – felt good! I was not seen as far as I know, and I went to purchase them at the front counter with a gift card.
Of course it was not a clean getaway. There was some question about the balance on my gift card and a line began to form behind me, as other customers began to observe the dude buying the rather large block heel sandals which looked like they would fit him perfectly. I gave up and used my regular credit card, and left the store far more stressed than I needed to be.
The incident would not have fazed me now, as I have made many purchases in stores often en femme – but this was my first. I think about it every time I put on those sandals, which is frequent since to this day they are my favorite dress shoes!
Hello Kris,
Congratulations for ‘passing through another ring of fire’.
Ya know, we can attempt to pre-think ‘what can go wrong today’ and try to be ready for it and then God throws us a ‘change up’.
Darn it, if I wasn’t in Kohl’s, completing an Amazon return, being issued a receipt which included a Kohl’s future-purchase discount. Likewise in drab, I took the ‘long way’ to exit, of course, through the ‘Woman’s’ section. I noticed a gorgeous cross-body handbag in magenta. The check out line was long enough to give me time to think up a ‘purchase excuse’ in case I needed one. It’s my turn, the clerk, a young woman in her mid to late twenties commented, “This is definitely your color”. Forgetting my pre-planned purchase excuse I said with a smile, “Do you think so?” Why, thank you”. I found my heart beating a little quicker as I exited the store.
Isn’t it those small things, those tiny obstacles, the unexpected, sometimes the things we create and place in the way that cause us to be a nerve-wrecking mess?
It is definitely a ‘growing thing’ but leaving that ‘comfort zone’, even momentarily, requires a bit of mental toughness and a smidgeon of courage. You did it. I did it. We all can do it.
With Love
Thea
A green halter top dress.My wife was with me and let me pick it out.She said I looked good wearing it trying this dress on.Bought it after that
It has been so long ago for me but I think it was a nite gown. I went to another town close by where I was thinking no one would know me. And I was nervous as hell!!! LOL But then I got to where I would buy pantyhose and once in a while some panty’s. Then I discovered the JC Penny’s and Sears catalog and then would do catalog orders by phone and was still nervous going to pick up my orders. And now online is GREAT but I do buy in person a lot now like Walmart. I always go and see whats on the clearance racks and if I see a cute dress, in fact I just bought a cute dress a month ago. I did come up with a ploy when I was younger, I would always buy a birthday or Christmas card or some kind of girlfriend card thinking it would throw off the suspicion…. LOL
Hello Becky,
You made me think and then roar with laughter regarding your last sentence, especially the about making a purchase “….thinking it would throw off the suspicion”…I’m still laughing, and not at you but about a instance of mine.
I always attempt to plan the right time to paint my nails. I simply cannot go en femme and decide to paint them moments before I’d to go out for a drive or whatever. Recently, I thought I had planned for a solid 72 hours of en femme. This time I painted my nails the night before. So I did. This one morning I discovered I needed to do some personal banking business and I needed to go inside for teller assistance. I wasn’t going to wear COVID gloves or gardening gloves this time. I rallied all the confidence and bravery I could find and set out for the bank. The teller was an attractive young lady, maybe in her thirties or forties. As I passed the paperwork over the counter she made the comment,”I love your nails”….My heart began pounding as it usually does when confronted en femme, but as I looked down to re-admire the work I had done not noticed I was wearing my ‘World’s Greatest Grand PA” t-shirt…Becky, how lucky was I to have been wearing an article of clothing, and as you perfectly stated in your note, “thinking it would throw off the suspicion”. I graciously thanked the teller and with a sense of relief said, “I’ll tell my grand daughter”. The teller said with a smile, ‘I know’.
Now that the pressure was off, I gave notice to the teller’s nails. They were absolutely beautiful. It wasn’t until toward the end of our business did I muster the courage to comment on her nails. They were oval, lengthy,glossy and glittered. After clearing my throat, I said with a smile and a return of compliment, “..OH and by the way, your nails are simply stunning”. Her reply, a gracious “Thank You, I’m meeting friends after work”.
Becky, I hear you loud and clear about being ready to “throw off the suspicion” but I think if we swallow hard, learn to calm down, and converse in our usual, polite, sincere, and personable manner, we challenge fear and reduce it to its lowest case. It (fear) will eventually disappear. You won’t need to ‘throw off suspicion and I won’t need my t-shirt. I guess ‘practice makes perfect’ Ya think?
Loved your story, and pardon me for my long winded response and type-o’s.
With Love,
Thea
PS …and nice to meet you.
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