How to bring up needing a bra to wife?

[RJG1979]

Hey fellas!  I'm pretty self conscious about my boobs and have had them since junior high, now am 41.  I measure a 44D in women's sizes & a 48A by Herroom male sizing.

I've talked about my boobs with my wife & told her how self conscious they make me feel, the bounce & jiggle,, and my nips always showing through my shirts but the conversation kinda stops there.
How should push this conversation forward & not freak her out?

[Dale Warnio]

 Bounce, jiggle, nipping out, those are all things women deal with, so I’m sure she empathized even if she didn’t say more.   Sounds like you want to start wearing a bra. If so, I suggest you ask her how she would feel about you trying wearing a bra and if she could help you,  including measuring your bra size.

Also,  since you said you were concerned about not freaking her out, I suggest you not mention to her that you’ve already measured yourself for a bra. 

 When she measures you as a D cup, I’m sure she’ll be very impressed and she should understand that you are too big to be going around braless. 

 Please let us know how it goes.

What are Herroom male size?

[curiousk]

Hi.  I think that due to the fact you have brought up your discomfort to your wife, the next step is talking about a solution to the problem.  If you are not able or willing to have surgery, then discussion about wearing a bra is the next discussion.  
I’ve had that conversation with my wife and luckily she is supportive of doing what’s comfortable for me.  It’s an uncomfortable conversation to have, but well worth it.  I wear a bra every day and comfortable doing so.  I went for a fitting and even send her pictures of the bras I tried on.   
Good luck!!

[blad]

My wife told me I needed a bra more than she did, but I already knew that.

It was a good starting point.

[42CSurprise!]

I think asking for help is a good way to go forward.  You've identified the problem and as others are saying, what you need is her help and support in finding a solution.  I can't imagine someone who loves you would want you to suffer.  Yes, this is an awkward topic to bring up but those come up in every relationship.  Working together for a solution that you both can live with is healthy.  You need to share your vulnerability, which isn't always easy for men to do... but honestly, that is a big part of what intimacy is all about.  Its not only what happens in bed... but what happens sitting at the kitchen table.  Good luck sorting it out.  There are many here who've found their way through this territory who will support you.

[Traveler]

Yes we will!

[bikerbob]

My wife had already pointed out to me that I was starting to look like a B cup so she was aware of the problem.  About this time I started borrowing one of her soft cup underwires for mountain biking.  We both have 42 chests so her bras fit me even if I don't fill the cups like she does.  It felt so good to not hurt that I was hitting bumps on purpose and knew what I had to do.

I kind of eased into the subject by asking her to buy me a sports bra for biking, which she did.  I was surprised at how much better I felt, even with a cheap bra, and started wearing it around the house.  After a few days, I told her I had been wearing it.  She hadn't noticed so I figured if I can fool a woman, I can get away with this.  Once we got to that point, it was easy.  I started mail ordering bras that other people on the forum had suggested and eventually arrived at a size and style that works for me.  Now I own more bras than my wife does but she seems OK with it and even borrows one of mine now and then.

I have been wearing mostly pullover leisure bras every day for nearly 4 years but have been test driving some underwires lately.  Once you get over thinking everybody is staring at your bra, you don't even think about it.  Once you try it, you won't go back to not wearing one.  Let us know how it goes with your wife.  We have all been there.
 

[Dale Warnio]

Underwires give good support, also nice lift and shaping 

[Goodnplenty]

I would ask her for help or advice.  It's a proven persuasion technique that people are wired to help others.  And when you frame it as help or advice they feel more involved and vested in finding a solution.  Also you can't just bring it up out of the blue.  Seeing how it's winter in most places you could wait until a particularly cold day and complain about nipple sensitivity and ask for help addressing it.  I never mentioned bras to my wife until one day she found mine and I told her that my nipples were so sensitive and painful in the cold weather that I needed something to ease the pain.  She never even questioned my need because she knows how painful cold nipples are.

[boobs are normal]

If too subtle the conversation will never start. The only way to bring it up is to "grow a pair" as they say and make a start.
I found a reference back to our daughters when they were my size.
I merely asked whether she would have told them they didn't  need a bra.
All I then did was to say that mine needed support and for the same reason. 
The lights went on!
Apart from needing a little reassurance  that there was no hidden agenda all was sorted after giving her a bit of processing time and the chance to ask a few supplementary questions.

I short order we went bra shopping together and have now happily progressed to sharing any clothing we fancy that fits from each others  collection - we are the same size except height.

I should say that outwardly  I present as 100% male - beard and all so when I occasionally wear a denim mini skirt in lieu of shorts I  am an obvious a man who wears womens'
clothing  on occasions and could not be mistaken for a crossdresser as is usually understood

[blad]

I think the first reaction of a typical wife is to evaluate if wearing a bra is not part of some bigger issue, and not just functional for breast support.

[gmast]

 when I occasionally wear a denim mini skirt in lieu of shorts I  am an obvious a man who wears womens'
clothing  on occasions and could not be mistaken for a crossdresser as is usually understood

I'm obviously not woke.  Please explain how a man that wears womens' clothing such as a mini skirt is not a crossdresser, an then explain what you think is a crossdressing.  Thanks. 

[boobs are normal]

Gmast

I reject the title of crossdresser for virtually everyone on this site who, for varying reasons, uses clothing from the women's aisles.

Using such clothing does not make one a crossdresser.
If you can stand the shock, take a cursory look at the pictures and conversations on such sites as crossdresser heaven.
Crossdressers make themselves as feminine as possible false boobs, tights heels etc etc and when caught short would make their way to the ladies restroom - they would look out of place anywhere else.

I would ask you not to not even imply anyone on this site is a crossdresser In the normal accepted definition of that word. It is slur and frankly shows sloppy use of the English language. 

I am just wondering if you would even dare call women in trousers crossdressers? Please do not misuse the term against men.

I have Scottish blood - I suppose wearing my kilt is off limits from your norm?  It is after all a skirt .
Get a grip

[gmast]

You seem to have confused the terms transvestite and crossdresser.

[boobs are normal]

Gmast
I will stop after this post otherwise this whole topic will get diverted.

I am not sure where you live but if you are in the US, it may be just a classic case of us being divided by our different usage of a common language.

No, I am not confused at all
I am not sure where you live but if you are in the US, it may be just a classic case of us being divided by our different usage of a common language.
I am English and refer to the  Oxford English dictionary (in this case the learners edition which gives rather more expansive definitions )
A transvestite is defined as someone who "enjoys dressing as woman" . Men on this site wearing bras are not wearing them for enjoyment but for practical reasons nor are they wearing them to be womanly. We are NOT crossdressers or transvestites. They are often (especially in the early days) not enjoying it and are certainly not dressing AS women
When I wear a skirt in hot weather it is because it is cooler ..... PERIOD.

I find transvestite just as offensive as crossdresser they have the same meaning. Look at a thesaurus  and you will find they are synonyms !! The other options are even more offensive (closet queen, drag queen etc etc) and should not be used of anyone on this site. It is highly inappropriate

If you can't grasp that I will leave you to argue with yourself

Call Scots transvestites or crossdressers and you will have all the clans after you.
If you do the same for women in trousers you will have the whole feminist movement after your blood