Susan's Place Transgender Resources

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