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How long can you keep a cigar in your mouth while smoking?

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No long. 10 seconds or so. I tried to keep one going while shoving snow last winter. Smoke in the eyes, drooling all over the place. Dropped it in the snow a couple of times because my gloves were fat. Not pretty. I won't try that again. Shovel snow. Stop. Start smoking. Or better yet: make seventeen year-old son shovel snow and I smoke like a mofo.
 

StogieNinja

Derek | BoM June 2014
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I've found I can go a while with a toro if necessary, but I much prefer being able to remove it. Hence, I will smoke while mowing the lawn, but not weed-whacking.
 
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I'm with everyone else. Too long and either smoke burns my eyes/nose, I accidentally inhale, I drool all over myself and/or the cigar, and so on.
Swallow the drool, squint, if it's putting off a lot of smoke, press your tongue on the cut end when you breath.

I dunno...I have no problems keeping a cigar in my mouth until it's time to tap off some ash.
 
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It's not easy nor very pleasant but I smoke while working in my shop sometimes. If you're indoors it's no problem, smoke goes one way and you breathe air in from the other. Sometimes I hold my breath for a few seconds or I tilt the stogie upwards so I can breathe fresh air. Also, holding it by the corner of your mouth pointing away from your face allows you to get some nice fresh puffs of air in a pinch. You can breathe through the side of your mouth instead of your nose, sometimes that works too since smoke coming off the foot goes straight up. So yeah, I can pull off the Clint Eastwood look if only temporarily.

Sometimes I'll inadvertently inhale a little and it goes to my head for a bit. No problem, just set the smoke down for a few minutes and if I have to relight, so be it.
 
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I have no issues keeping for a few puffs. Say 5 minutes or so. Smaller sticks no issue at all. If it smokes like a chimney then might have to take care how or where smoke gets blown.
 
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I've frequently seen a guy doing yard work around the corner with a cigar in his mouth for like 10 minutes. He is literally my cigar smoking idol.

I can hardly take a pee beside my fire pit without choking on smoke. I don't retrohale, so the smoke going up my nose isn't the most pleasant thing haha
 
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