Notifications
Clear all

Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.

Join Crossdresser Heaven today to participate in the forums.

My first time wearing a bra: How did you try on a bra for the first time?

144 Posts
53 Users
322 Reactions
1,637 Views
Posts: 81
Lady
(@orcharddwee)
Estimable Member     Staten Island, New York, United States of America
Joined: 5 months ago

When I first started crossdressing, I didn't bother with a bra because I didn't think I would have the flexibility to reach behind and put in on.

And then one day, I was watching Reanimator, a horror video nasty from 1985. Amidst the copious gore, there is one scene where the main actress, Barbara Crampton, after making love gets up in front of the camera (gotta have those bewb shots for those horny teenage boys in your audience) and puts on her bra. How she did it was she put in on in reverse, with the cups in back and the hooks in front so she could easily fasten it, and then when fastened she would pull the bra around, put her arm through the straps, and set the bra in place. It was my eureka moment and it's the technique I use to this day. Thanks, Barbara!

Reply
5 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080
(@valentina16)
Joined: 2 months ago

Noble Member     Worcester, Worcestershire, United Kingdom
Posts: 972

@orcharddwee I do the fasteners up and pull them over my head, like a jumper. A bit manly perhaps, but it always works quickly and reliably. Taking it off is just the reverse, and that has got me out of a couple of undercover scrapes. However, I can now undo a bra in an instant, a simple flick-pinch of thumb and middle finger. So quickly that on certain intimate occasions, I have to deliberately slow things down to become all manly & useless fingers & thumbs 😬 Oh the joys of being underdressed…🤣

Reply
Lady
(@julie51)
Joined: 1 month ago

Estimable Member     Chicago, Illinois, United States of America
Posts: 80

@valentina16 

Cool😎 ME2 I do the same thing l love the pullover option💕

Julie

Reply
(@valentina16)
Joined: 2 months ago

Noble Member     Worcester, Worcestershire, United Kingdom
Posts: 972

@julie51 We be bosom pals then! 💚☺️💚

Reply
Lady
(@julie51)
Joined: 1 month ago

Estimable Member     Chicago, Illinois, United States of America
Posts: 80

@valentina16 Happy Valentine’s Day’s to everyone 💕

Reply
Posts: 1080
Lady
Topic starter
(@marieclaire2)
Noble Member     London, United Kingdom
Joined: 4 years ago

I remembered that some time ago I wrote an article here at CdH "The first bra we never forget". I invite everyone to read and comment.

Reply
1 Reply
Managing Ambassador
(@ellyd22)
Joined: 2 years ago

Majestic Member     Norfolk, United Kingdom
Posts: 5409

@marieclaire2 

Here's the direct link to that article:

The first bra we never forget! – Crossdresser Heaven

Reply
Posts: 110
Baroness Annual
(@girlyboy9020)
Estimable Member     Maryland, United States of America
Joined: 2 months ago

I tried on my sister’s red training bra when my mom and sister went out for an errand and I was left home alone at age 13 🙂! I instantly felt very happy and relaxed!!

❤️ Ashlyn

Reply
1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080

@girlyboy9020 Very good. It's not very common to see red training bras...

Reply
Posts: 972
(@valentina16)
Noble Member     Worcester, Worcestershire, United Kingdom
Joined: 2 months ago

So, how to put on a bra: a friend told me (!), an alternative method to help make sure all clasps are connected is to clasp it up and pull it over your head like a sweater. Perhaps a bit of a laddy non-femme approach, but quite practical. Conversely, it is a quick and possibly a more discrete way of taking a bra off quickly ‘under cover’ to pull it off like or even with a sweater. This I guess can only apply where the breasts are artificial. So my friend said. 😉

Reply
2 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080

@valentina16 It's a practical way that can help a lot of people, but I think it's more feminine to put your arms through the straps and close the hooks at the back!

Reply
(@valentina16)
Joined: 2 months ago

Noble Member     Worcester, Worcestershire, United Kingdom
Posts: 972

@marieclaire2 Yes, it’s a bit laddish, if that description is at all appropriate wearing a bra.

Reply
Posts: 33
(@Anonymous 100872)
Eminent Member
Joined: 1 month ago

I learned watching my wife, She would take the strap and hook the hooks in front of her, the spin the bra around to the hooks were in back the run her arms through the straps...voila!!

She also had bras that were designed to hook in front. I called those front loaders...lol...that;s what i prefer.

Reply
1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080

It's a practical way that can help a lot of people, but I think it's more feminine to put your arms through the straps and close the hooks at the back!

Reply
Posts: 135
Lady
(@samanthaj)
Estimable Member     Cambridge, Cambridgeshire, United Kingdom
Joined: 4 years ago

Yes I remember the first time I put on one of my mums bras as a young teenager, it was a yellow Gossard wonderbra and I even managed to fasten it up at the back, not as flexible nowadays as I have to fasten my bras at the front then spin it around. That was it, every time I found myself in the house alone it was straight up to her underwear draw then picking out a bra, knickers and tights and wearing them for just long enough that I didn’t get caught. That one encounter with a wonder bra set me on a life long journey to where I am today as Samantha 

xx

Reply
2 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080

@samanthaj Mom's lingerie drawer is Heaven on Earth

Reply
(@kimberlyannvictoria)
Joined: 4 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 515

@marieclaire2 OH yes it is!!!!

Reply
Posts: 7
Lady
(@mbtrooper)
Active Member     Austin, Texas, United States of America
Joined: 3 years ago

My first bra that I tried was my sister's training bra. She is one year older than me and when she reached that certain age, my mom took her to get her first training bra. I remember it being something special in which only my mom and her went to the store. You could feel it in the air that something was going on and my sister was excited about something.

When they came home, my mom had a couple of bags from some other stores (don't remember, it could have been groceries), but my sister had her own bag and went immediately to her room. She came down soon and I went upstairs to use the bathroom. When passing her room, I saw the bag on her bed. I went in and took a look. There were two training bras in the bag and the empty packaging of another one.

At this point, I was already trying on her panties and dresses, so I was excited to try this new item. It was hard to contain my desire and had to wait until the next time I was "sick" and stayed home.

On the day I was home alone, I went to her panty drawer and saw one of the training bras folded up. I still remember it was a light blue bra. Then I saw her hamper. Peeking out from under a shirt I saw part of her training bra. I moved the shirt and there it was. It was a very light color of pink with a darker pink bow sewn to the center front. I remember it being cotton with a tiny lace border at the top.

It was a pullover, so no clasps. Under that was a pair of her panties that closely matched the bra. I instantly knew I had to wear it. I pulled it on over my head and it fit. It wasn't tight, but I could feel the snugness around my torso, reminding me it was there. I put a couple of socks into the bra, but it didn't look right and I took them back out. I then pulled on the panties. Seeing the closely matching panties and bra set my future desire to want to match bras with panties, which I try to do. 

I wore the set the rest of the day along with a pink dress of hers. I didn't want the day to end and felt so good wearing the training bra. To this day, I still have a fondness for bras or bralettes that look like training bras. I wish I could find some, but I am have a 44 inch chest. Unless it's made to fit, I'm not finding any. 

Wow just looked back and I wrote a lot. I'll shut up now!

Reply
4 Replies
(@kimberlyannvictoria)
Joined: 4 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 515

@mbtrooper Wonderful story!!! I think all of us girls can relate to this story. For me I remember both of my sister's getting the Leggs pantyhose eggs from my Mother and wondering why I didn't get one.

Reply
Lady
(@mbtrooper)
Joined: 3 years ago

Active Member     Austin, Texas, United States of America
Posts: 7

@kimberlyannvictoria Thank you, I also remember my sister getting tights and different types of panties in different colors. She got some in cotton and some in nylon. Us boys were just handed a package of white Fruit of the Looms. I remember thinking how unfair it was.

Reply
(@kimberlyannvictoria)
Joined: 4 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 515

@mbtrooper Yes I agree we should got pretty clothes as well

Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080

@mbtrooper I also started with my sister's training bras, but I had never tried anything feminine before and I had to put my arms through the straps of a white training bra and fasten the hooks in the back lol After all, I wanted to know why and how the girls at school were starting to wear those!
I liked it so much that I secretly wore them more often. Although I wanted to have my own bras, I was a bit jealous of their girls being able to buy and wear them naturally...
(Over time, I started trying panties and other things...)
But your experience was unforgettable: everything in pink! I remember when I put on a pink bra for the first time: I felt like a princess!

Reply
Posts: 972
(@valentina16)
Noble Member     Worcester, Worcestershire, United Kingdom
Joined: 2 months ago

My first bra adventure was a slightly (ok, very) tipsy encounter, after a wedding, staying in a hotel room with my GLW. Now she is a small lady, almost (but not quite) 5’. As she is a mere 38 belt size and I am a tight 44, comfortable 46, it was quite a challenge trying on her bra. Yes, it was taught, yes, it might have broken (do bras snap/break?), but boy was it hugging. The bra was hooked and so was I. ☺️

Reply
3 Replies
Lady
(@mbtrooper)
Joined: 3 years ago

Active Member     Austin, Texas, United States of America
Posts: 7

@valentina16 So what led to you trying on your lady's bra?

Reply
(@valentina16)
Joined: 2 months ago

Noble Member     Worcester, Worcestershire, United Kingdom
Posts: 972

@mbtrooper I didn’t then have any of my own.

Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1080
Posts: 41
Lady
(@dee2)
Trusted Member     Iowa, United States of America
Joined: 1 month ago

I did not have any sisters. As a child, the one thing that I found access to is panty hose, so I tried them on and wore them under my pants a few times. As an adult, I bought a bra online. It fit me and the feeling was heavenly. I lost that bra in a purge. I have since purchased more. The ones that fit well are sports bras. 

Reply
Page 3 / 3

©[current-year] Crossdresser Heaven | Privacy Terms of Use | Link to usContact Vanessa | Advertise with Crossdresser Heaven

 
[kleo_social_icons]
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!