My attitude is quite adequate, as a person has the right to dress as they see fit. I personally prefer to wear something that will bring a little discomfort and even pain. It’s my personal fetish obsessharness something like that.
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Can you elaborate a little bit? How do you get discomfort and pain from a bra @bettyvilliams1 ?
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Sexterminatrix will occasionally get me to cross-dress for her viewing pleasure, bra included. I even invested in some lifelike breasts to fill the cup properly and enhance her experience. It may sound strange to others, but as it usually leads to receiving a good pegging, I’m not complaining at all! Next step is to find me some classy high-heels that aren’t too pricey to complete the ensemble.
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Are the “life like breasts” the simple form types that fit in the cups or a harness type? I have some questions about this depending on your answer.
Just simple form, standalone types. I feel having a breast harness AND a bra would be too many strraps going on. 
Agreed. If I am fitting the man boobs I go small on cup size but I do have a silicon pull over boob set that requires I wear a C cup as well. No straps, it’s a pull over thing with fake boobs attached. It looks better than it feels with perky nipples and all. No straps. More of a cropped t-shirt thing.
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Good for you! There are plenty of classy, affordable heels in larger sizes these days
Really been enjoying the bras my wife bought me . They are see through and with the bra extenders fit pretty well . I just wish one was pink to match the super cute , sexy panties I bought that were tailer made . You would not believe what we paid for two pair with shipping from half way around the world . A matching bra would be great .
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@Oldman price aside are the sexy pink panties (knickers) worth it? Are they your new fav underwear now?
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Just got them and only tried them on . Person who makes them get measurements soft and hard and then makes them . Took weeks from ordering to receiving . Kind of waiting for getting tan . We both think they are cute and hot , hot pink mesh and lite blue trim and tiny bows , two in front and one in back . When I get a bit more tanned I will post photos . Also have several bras I have not posted .
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I wear a bra to work most days and it is usually lace without underwires/padding etc etc.As you say,coupled with a dark top and no one ever notices.It is the thought you are wearing it which at first makes you think you stand out like a beacon.Some days i wear a lighter top plus jacket giving an occasional hint of what is underneath but even then no one ever seems to notice,does feel really nice and sexy though.
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First couple of times I wore lingerie properly (and by that I mean chose it and purchased it specifically for me as opposed to just mucking around with the OH’s stuff) I felt as though everyone would know what I was doing and on top of that be very judgemental, ridiculing or sickened by it.
But once you get comfortable, physically and mentally, with wearing bra, knickers and so on you’ll also realise a couple of things….
No one will know (unless you want them to)
And even if they did no one will care that much.
And if they do, just tell them it’s your “thing” and none of their business.
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Sounds fantastic @Oldman , looking forward to seeing the pics
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@Neversaynever how about doing a practice run of wearing a bra underneath your dark polo out & about on a none work day maybe to the supermarket or such like to see how others around react and how you feel about this prior to then wearing to work?
Just a suggestion but it might give you the confidence to try it, and lets face it you could always slip into the toilets and remove the bra if you suddenly changed your mind.
Hope this helps 
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Just to echo what @Mid-50s_kiwi said, the trick is to ease yourself in to it gently.
Don’t think you’ll wear a full-on basque and stockings first time and not feel more than a little nervous! I know I did.
Couple of suggestions……try starting with just knickers first as these are obviously far easier to keep concealed, then once you’re at ease with wearing the bottom half, add a matching bra, again slowly at first….maybe just for a short walk from home, or for the journey to work then take it off once you get there?
Also think about your choice of lingerie/underwear. Some types will show up more than others (this isn’t just a male lingerie problem by the way…girls have it to). Have a search for things like “tee shirt bras” or “invisible” underwear as these are designed to be as non-revealing as possible.
And finally, make sure you get a good fit. Measure yourself properly and, although male dimensions are significantly different to female ones and so you might be at the very edge of lingerie size ranges, don’t guess. It’s dead easy to think “Well my (female) OH is a 34c so I’ll just get something a bit bigger than that”. Lingerie sizing doesn’t work like that, bras especially. Before simply saying “bigger” you need to think “in what way bigger?”
It’s another thing I like about lingerie and wearing it. It’s not as simple as just clicking on “XL” or whatever and makes the whole experience much more involved and thus much more rewarding.
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The heavier the shirt the less one will see. Bra under a sweat shirt will never be seen. Bra under a T with a light jersey won’t be seen. Bra under a t will be seen.
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I’ve always found Nudi Boobies are great way to add a bit to the front without it being particularly obvious.
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I think the question being asked was how to make lingerie less obvious, not more! 
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Happy to dip out of this one!
Received my LH order a few days ago . Bought Coquette Stretch Lace Bralette and a Plus Sized Peek-a-Boo White Lace Bra and Crotchless G-String . Surprisingly the peek a boo fit all the way around , I really like the exposed nipple . The Bralette was way too small , so my amateur seamstress skills came into play . I cut the back in half and added in two thin black elastic straps ( formerly part of a garter ) about 4" long . Then I relocated where the back of shoulder straps attach as far to the middle as I could . I think it is now one of my favorite bras . Hopefully I can get to taking photos soon . Other bras I have I use the bra extenders and they fit much better . I think they would be better if I relocate the shoulder straps in toward the middle . I still want a few of the silky and or sheer bralettes with lace . But they are crazy expensive . However several are label men’s , price goes way up . Another word that jacks the price up is Bridal .
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