What was the first clothing item for those of the "opposite gender/sex" did you wear?
A. Undergarment.
B. Outer garment.
Hey, no replies yet, so maybe this'll inspire others to contribute.
Outer - and it was quite a while before I tried inner. Years, even.
Condensed backstory is the first time I tried on clothes that weren't conventionally worn by my sex was as a kid when we swapped clothes around to see what we looked like in them and what it felt like to wear clothes of another sex. So it was a mutual thing and most of the interest was on the girls' side, but I remember feeling that something deep inside was more comfortable with this than the rest of me said it should be. It was definitely an inflection point, not that I realised it at the time, but I couldn't ever quite get it out of my mind.
Outer. I had a skirt I had liberated from a bag of old clothes and I wore my sister's jeans to School a couple times.
I was raised on a ranch with three brothers, so I had little opportunity to experiment.
My first recollection was shopping for thermal underwear for an upcoming camping trip. All of the men's long underwear were too expensive. I could afford it but refused to pay that much for underwear.
I decided to go to a different store. On my way out, I walked past the women's department and they had women's thermal tops on sale. I felt the fabric and it was soft so I bought two packs. I was amazed at how warm and comfortable they were. I still have them and still wear them when it gets brutally cold out.
TL;DR Underwear
Quote from: Lori Dee on September 27, 2024, 08:46:17 AMI was raised on a ranch with three brothers, so I had little opportunity to experiment.
My first recollection was shopping for thermal underwear for an upcoming camping trip. All of the men's long underwear were too expensive. I could afford it but refused to pay that much for underwear.
I decided to go to a different store. On my way out, I walked past the women's department and they had women's thermal tops on sale. I felt the fabric and it was soft so I bought two packs. I was amazed at how warm and comfortable they were. I still have them and still wear them when it gets brutally cold out.
TL;DR Underwear
It is nice that you still have them and that they fit.
Chrissy
Quote from: ChrissyRyan on September 27, 2024, 10:01:19 AMIt is nice that you still have them and that they fit.
Chrissy
They are very lightweight and stretchy, so they work well under sweaters, sweatshirts, fleece, etc.
Quote from: Lori Dee on September 27, 2024, 10:15:13 AMThey are very lightweight and stretchy, so they work well under sweaters, sweatshirts, fleece, etc.
Terrific!
Chrissy
Quote from: Lori Dee on September 27, 2024, 08:46:17 AMI decided to go to a different store. On my way out, I walked past the women's department and they had women's thermal tops on sale. I felt the fabric and it was soft so I bought two packs. I was amazed at how warm and comfortable they were. I still have them and still wear them when it gets brutally cold out.
How many ways are there into this? I bet we all found out in different ways, right?
Quote from: TanyaG on September 27, 2024, 10:27:56 AMHow many ways are there into this? I bet we all found out in different ways, right?
Likely so. Could be some interesting stories shared.
Underwear ( midis, thongs )
Before I brought them. I was questioning if it was wrong. So I asked my local charity ( switchboard) to see if it was okay. Then I had a feeling I was going to get stopped in the supermarket. So every since brought underwear 🌈 and so far ( Thongs, midis, shorts, full briefs)
A white pair of stockings, closely followed by barely black tights. Then thick opaque tights as they hid my legs hair and I used a navy blue bath towel as a wrap around dress. It wasn't until uni I was able to buy a dress.
Sometimes I pull out different outfit possibilities and look at them, at times laying them out on the bed. Guys do not do this I do not think.
We just have many possibilities of what to wear as a woman, this makes for important decisions to be made. And make them we do. I have no complaints about this.
Chrissy
Pantyhose that I stole from a department store, I was too embarrassed to purchase them. They felt dam good when I got home to try them on.
Under. And who doesn't forget their first time ;) In my mid 50s now and I"m guessing it was around 18 yrs old and my heart was racing when I finally got the courage to walk into a lingerie outlet store (over-runs etc)...it was like I had just strolled into heaven. I must've picked a good time (prob early Monday morning) because it was fairly quiet. The item in question was a full slip in black and that's all I purchased. Half the thrill for me throughout my on/off again CDing journey was the actual purchase of fem apparel and the assistant's reactions etc. Not much talk back then but just a slight frown and a neutural tone lol. Of course as the years have gone by so the stores have become more accepting and helpeful to gurls like us I'm pleased to say :)
* Sorry OP, I thought you asked for first item purchased.
Quote from: CD4Eva on February 25, 2025, 04:52:44 PMUnder. And who doesn't forget their first time ;) In my mid 50s now and I"m guessing it was around 18 yrs old and my heart was racing when I finally got the courage to walk into a lingerie outlet store (over-runs etc)...it was like I had just strolled into heaven. I must've picked a good time (prob early Monday morning) because it was fairly quiet. The item in question was a full slip in black and that's all I purchased. Half the thrill for me throughout my on/off again CDing journey was the actual purchase of fem apparel and the assistant's reactions etc. Not much talk back then but just a slight frown and a neutural tone lol. Of course as the years have gone by so the stores have become more accepting and helpeful to gurls like us I'm pleased to say :)
* Sorry OP, I thought you asked for first item purchased.
I am sure they (or the store owner) appreciated the additional sales revenue too!
I like wearing a nice, dark jacket with a solid white top and a longer pleated skirt.
But I also like wearing a T, jeans, and sneakers!
I'm kinda surprised at replies so far. My hubby's first 'experiment' was Mom's bra. Most of our CD friends started in the lingerie area.
Eileen
A North Face women's down jacket, size small.
Quote from: Eileen on March 16, 2025, 12:28:31 PMI'm kinda surprised at replies so far. My hubby's first 'experiment' was Mom's bra. Most of our CD friends started in the lingerie area.
Eileen
We are all different, so we have had differing experiences.
I would think that undergarments may be tried first then outer ones. But, it could have been a top or bottom tried first. After all, it is interesting to see what we appear like wearing the clothes of our correct gender, and you cannot see much of the undergarments unless that is all you are wearing. But wearing what's underneath and cannot be seen while out may be the reason many try those first.
Chrissy
I will be wearing very nice professional office clothes tomorrow.
It may be quite a busy day.
Chrissy
Hi All
Underwear (briefs floral pattern)
Hugs
Sarah B
Pantyhose. It was pantyhose and tights that started it all. Then it was "wouldn't pantyhose look better under a dress?". If I was told I could only wear one opposite sex garment, it would still be tights.
Quote from: Lovertights73 on May 06, 2025, 01:52:52 AMPantyhose. It was pantyhose and tights that started it all. Then it was "wouldn't pantyhose look better under a dress?". If I was told I could only wear one opposite sex garment, it would still be tights.
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@Lovertights73Dear Lovertights73: ONE more thing that can be done......If you feel comfortable doing, please find you way to the INTRODUCTIONS board ...
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Hi LovertightsMy name is
Sarah and I would also like to formally, Welcome you to Susan's Place!
I see that other members of Susan's have also welcomed you as well.
Other than tights, which I wore a long time ago when I was working in Sydney, what other clothing do you like?
Once you feel comfortable here, it would be appreciated if you add a little bit more about yourself in the other forums and threads. I would appreciate it very much as, I'm always interested in learning something new about new members.
In addition members of Susan's will more than likely will discuss problems or issues that are similar to yours as most have experienced these issues as well.
Take care and all the best for the future.
Once again, Welcome to Susan's Place!Best Wishes AlwaysSarah BGlobal Moderator@Devlyn @Jessica_Rose @Mariah @Northern Star Girl @Lori Dee @Lovertights73
Quote from: Sarah B on May 07, 2025, 10:29:48 PMOther than tights, which I wore a long time ago when I was working in Sydney, what other clothing do you like?
I have really only tried dresses with tights.
Sloan
It is nice to wear comfortable women's clothes, that is for sure.
Chrissy
For me it was shoes. I found a pair of these flower child VERY 70's era leather sandals in the the spare bedroom closet. They belonged to my Mom. I was 12 I think? Afterward in was anklets (I felt these to be VERY girly for some reason). When I moved out at 18 I bought a pair of cheap heels at Walmart at 3am. I was mortified and the clerk couldn't care less (laugh). An ex-girlfriend left a skirt at my place and one day I tried it on I decided it was awesome. Haven't really looked back since.
Well, the first ever thing before I knew that I was who I was (at 5 or 6), was a lovely princess dress and loved it.
After that a ballet maillot...and ever since loved the maillots and swimming suits :D