I want to be able to wear boxers, but I can't buy them on my own (my parents pay) and I don't know how to ask them about it. It would be kinda awkward to just go "Hey, dad! Can I buy some boxers?"  Does anybody know how to ask? I would prefer to ask over email, since I choke up when I try to talk about anything TG related. Any ideas/successes/failures on the subject? Any help would be appreciated.

I "stretched the truth" on mine when I was in high school...told my mother I needed new underwear as my old ones were getting too worn out, and I couldn't afford to buy them myself. She gave me the money and I went out and bought boxers. Most parents won't come inspect your underwear drawer afterward ( ....even though mine actually did, as she had a feeling I would do something "weird" like that).

Hmm I live on my own so can buy whatever I want. I'm not really sure how to ask for something like that without having to explain.

I used to tell my mom boxers were comfy to sleep in. It worked fairly well, but then I was buying my own clothes from the time I was 14. It could backfire, of course, if she decides to go out and buy you some girly pajamas.

SD

I would die if they bought me girly pajamas.   

I have told them that I'm TG, but it's still awkward. That's why I'm having trouble with it. I suppose I could just ask for some money to go buy new underwear. That's not really unreasonable, but my worry is that they'd eventually find out and then I'd have to explain more than if I had just asked in the first place. And I'm pretty sure they'd find out (i.e. I bend over to pick something up and they see my boxers). Man, that would be awkward, but probably kinda funny.

Well, if they ask why you weren't just up front in the first place, you could just explain that you were afraid of their reaction, or just didn't think about having to specify. I mean, normally people wouldn't have to specify what type of underwear they want to purchase. And it's something that they'll have to deal with anyway.

Or just say screw it and go commando.

Meh, I like boxers because there's a lot of room to breathe and its a certain freedom from the dreaded panty I wore for so long. Though I don't have anything hanging and swinging there (yet ) so I might reverse that eventually...though boxer briefs I do have for when I feel like packing.

For reasons I don't understand sorority girls seem to like wearing boxers, and so do a lot of the girls I work with who have to bend over and pick stuff up all the time and I guess get tired of the lace sticking up over the top of the pants.

Quote from: Chris the Wookie Slayer on November 16, 2009, 02:12:56 AM
Or just say screw it and go commando.

I suppose you're right. You wouldn't need to specify what kind of underwear you were buying in any other case. In fact, it would be kinda weird if you did have to say what kind of underwear you were buying. 

Well, my sister wanted to buy a thong, and my parents were ok with that; my step-mom even went with her to buy them. I think it's just as awkward for them to think about their daughter wearing thongs as thinking about their transgendered child wearing boxers. That seems to make sense, at least.

When I use to wear women's underwear (better than saying panties) I found that they'd pinch and cause discomfort around my thighs. Because of that I started wearing boxers and am now much more comfortable.

And that can be the reason you want boxers right there. Just say, hey the ones I have now are driving me crazy so I wanna get some boxers.

Quote from: Osiris on November 17, 2009, 01:22:37 AMWhen I use to wear women's underwear (better than saying panties) I found that they'd pinch and cause discomfort around my thighs.

Yeah, for me men's briefs are waaaay more comfortable than women's underwear (never called them panties as well). I wear boxers to bed but I could never wear them as underwear. Too uncomfortable for me.

I wear boxers as shorts in summer. They're way more comfortable than regular shorts, they look like shorts, and they come up to my waist instead of just over my pubic bone like most women's shorts do. You could just say you want some boxers to wear as shorts, except that you probably live where winter is on its way! 

Just save up your lunch money or allowance... and go out by yourself and buy it, get a ride from a friends mom or dad, and go with a friend... if you want to hide it... if you don't mind telling them straight forward then, just say that you want to try out boxers.

Is there a cool family member other than your folks you could ask?

Maybe Santa could get you some this year haha. Really tho it would be cool to have a big brother so to speak that could mail you some. Not sure how you would explain that to your folks later but its an idea.

Tell them you want to buy your own underwear. You're probably old enough that saying it's embarrassing to have your parents buy them for you.

If they give you crap about what kind of underwear you're buying, give them a weird look and ask them why it matters what cut of fabric you want to cover your butt.

Briefs are way better than women's undergarments anyway, they don't splice your @ss-cheeks in half.

And like someone else mentioned, boxers are great for sleeping in! they're soft, comfy, and cheaper than women's 'sleep shorts'.

@ Osiris & Radar: Doesn't putting the word "panties" in paranthases kinda defeat the purpose of not calling them that? 

@ Squishy: It never really gets that cold here; you could wear shorts in the winter and be plenty warm. I miss the rain. 

@ CodyJess: That is true that it's just fabric, why should it really matter?

Nowadays when I think about womens underwear I can't help but think of it as a conspiracy. For some horrible reason, whenever I used to wear them I would get horrible, horrible wedgies ALL of the time! 'Boy' shorts were the WORST! Boxerbriefs and boxers were marginally better, briefs an improvement on that, but recently I've discovered the JOCKSTRAP. When I wear them, I never get wedgies, EVER, because... Well, since there's no fabric covering your ass, there's no fabric going UP it. I also supports my prosthetic really well, so I don't have to worry about it flying around in my pants/ending up sideways when it isn't glued on.

As for advice, I remember my dad acting kinda funny when I asked him about boxers when I was in my teens, too. I'd just tell them it's for sleeping purposes- I mean, especially if you have friends over or go to friends houses, explain to them that you don't need anyone seeing you in panties under that circumstance. I've known girls, even, who wear panties and put boxers on TOP of them during sleep overs, for modesty. Boxers are more acceptable to wander around the house in when it's hot- I imagine parents could empathize with that, as most of the ones I've met would rather not see their kid running around the house in panties! Too revealing!

Cairus thats great I just spit coffee all over my laptop reading that.    I'm going to get a jockstrap tonite now. I have a few pair of old navy boxers I like to wear to work but my fav choice is briefs by Joe Boxer.

Unforgiven where are you that it stays so warm in the winter?