My husband needed new underwear. So, off to the store I went, after I dropped him off at work. I got him a pack of tighty whities, something I wore when I was trying to fit in as a male. It wasn't the first time I had to buy him some underwear, but it still made me feel uncomfortable. I wonder ... could that be compared to when a man shops for tampons?

What is the most uncomfortable purchase y'all have made?

Yeah that would be uncomfortable for me also. One time i bought an athletic cup for our son and that was not a pleasant purchase for me. ( i did all my sports without one and never was injured down there)

I used to happily buy pads for my wife and was always the only guy in the feminine products aisle at the drug store. My brother was appalled. To me it was no different than buying kleenex. He would also get all pissy when I would routinely ask for help or directions. NOW I know why these things didn't bother me the way they were supposed to.

I used to buy feminine hygiene products for my wife.  It never bothered me at all.  I figured that any man who wasn't man enough to buy something for his wife that she needs was a pretty pathetic specimen.

On the other hand, buying women's underwear for myself before I came out, that was a bit uncomfortable.

Buying any women's clothing made me very uncomfortable at first when I couldn't go shopping in women's clothes and I couldn't be sure that people read me as female. After I had some women's clothes to wear and was quite sure I passed I solved this by going out shopping as female Strangely the closer I am to full-time the less problems I have with buying women's clothes as a "man".

My most uncomfortable almost buy was when I was not full time and just going to therapy pre-hrt. I felt like everyone was watching me and I was hot and flush.

Quote from: Lynne on August 11, 2016, 05:06:02 PM
Buying any women's clothing made me very uncomfortable at first when I couldn't go shopping in women's clothes and I couldn't be sure that people read me as female. After I had some women's clothes to wear and was quite sure I passed I solved this by going out shopping as female Strangely the closer I am to full-time the less problems I have with buying women's clothes as a "man".

Oddly enough, I never felt weird buying women's items. It just feels weird to me, buying guy stuff when Phillip is not with me in the store.

Like a number of the other respondents to this thread, I no longer have any uncomfortable feelings buying feminine items even though, at present, I still present as male.  This includes both female items for myself and feminine hygiene items etc. for my wife or daughter.  That said, I'm still not at the stage where I would feel comfortable going into a boutique type shop where I'd feel more conspicuous but the larger high street chains present no problems nowadays.

As it happens, I was browsing the women's sections in a clothes shop and shoe shop yesterday.  I did get a strange look from a very young (probably mid-teens) assistant while admiring a dress but I guess, at that age, she'd not yet got the maturity or knowledge to understand.  After her double-take, she just moved on and left me be.  In the shoe shop, where I'd previously just had sneaky looks at the women's section on the way to the mens, I stopped for a proper look and, after maybe half a minute, surprised myself that I'd become a little too interested for someone in guy clothes!

The other thing I've found is that, since coming out to my SO (without going into too much detail, I had to as I thought she'd found something of mine (she hadn't) and, as a result she gave me the ultimatum to quit or she'd throw me out), I've now got no excuse if she asks me to go and buy something for her or my daughter so I just get on with it.

Amanda

I can't really remember any uncomfortable purchases for a fair while if I'm honest. Maybe people are just being nicer...

All joking aside, I think that once I was over the fear of looking a bit "odd" it just stopped being a problem.

Having said that, I have bought some very uncomfortable items


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  For me buying anything in women's apparel for myself was always an uncomfortable thing. Especially panties, bras, or shoes.
  On the other hand buying women's sanitary products was never an issue. I grew up wit 4 -5 sisters being at home and this was a very common task I was requested to do.


  Hugs,
    Jeanette

I recently bought a pack of hair ties, would've needed them anyway if I was presenting male since the official story is I'm growing my hair for the trendy man-bun. But given the truth I still felt a bit like I was being watched intently, of course I wasn't.
That said, I've relaxed a bit since coming out to a few choice people, no longer worry so much about feminine body language popping out occasionally for instance. I've got a long road to unlearn my bad habits of hiding.

I actually found it uncomfortable buying guy stuff. Purchasing things like razors and shaving cream just makes me feel really awkward.

At my age I have stopped caring what anybody thinks, clothes, pants bras I just get them, went in Boots as they do foundation matching, assistant did not bat an eye, just found correct one for me.Bought tights and stockings in my local grocery  store no problem.