Jerking off... in boxers?

So you're lying in bed, getting horny, JO is inevitable, you get pumping, slip out of the underwear, now the messy part -- do I cum on the sheets, all over myself or in my other hand, or into my underwear? Easy answer, I change underwear daily so blast off into what is going into the laundry anyways.
I've been jerking off into briefs since I was 12 by wrapping them around my dick and going to it. I grab a pair from the laundry basket and let it rip. As PinkSteel stated, they're going in the laundry anyway.

2 years ago, my default underwear changed from briefs to boxers. I can jerkoff in boxers while I'm still wearing them. Makes for some fun sessions at the computer. If I don't J/O in my boxers, I have to use baby powder to cut the friction. I made my dick bleed over the weekend by pounding it dry. The only wet lube I use is soap in the shower, and I prefer a dry method when I get off.
 
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Not trying to highjack this thread but the feeling of jerking off inside a pure woolen sock gets me off. I have to stop after 3 strokes of cum because the feeling around my glans is soooo intense. Try it and tell me its not the most erotic feeling..... mmmmmmmmmmmm
 
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Okay I'm not exactly sure if this is something new or something old but, whats the deal with jerking off in your underwear? 2 of my friends do it and don't ask me how i know this but so does my dad. Is this like a trend or something? Does anyone here do it? How did you find out about it?

Dude - jerking off in your underwear simply means more clothes washing and spending more on washing machine powder and hot water
Why waste money? Jerk nude
 
my friends and I used to do it while in school. Like homeroom or at the lunch table. You pretty much have to be wearing jeans or not cum a lot to get by with it.
 
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my friends and I used to do it while in school. Like homeroom or at the lunch table. You pretty much have to be wearing jeans or not cum a lot to get by with it.
Hey Digbychris: Nice avatar photo. Would love to see a larger version. Looks hot!
 
When ever i jerk off, i take evything but my underwear off, then i lay on the floor (on the stomach) in a very clear space, the I move my legs back and forth realllllly fast and it feels amazing! less of a mess too. And, you don't have to use your hands. Easy peasy.
 
i've always done it in my boxers or basketball shorts. feels good and contains the cum, so it doesn't shoot all over me and my carpet/walls, etc.

Only downside is the cum stains will fade your boxers, shorts, etc. over time.
 
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