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Cutting Your First Cigar
All cigars are "capped" to protect their freshness and to keep the tobacco leaves from unraveling before they are smoked. All this means is that you'll have to cut off a chunk so that you can smoke your cigar. When you buy your first few cigars it's a good idea to go ahead and buy a guillotine style cutter while at the shop. They cost about $5 or less and are a good little investment. You don't want to ruin a good cigar by using something else to cut the tip of the head on your cigar because it could cause the rest of the cigar to begin unraveling.
I've seen too many guys trying to look cool at parties trying to play the role and biting off the head of the cigar... problem is they don't look very cool a few minutes later when their cigar is falling apart in their hands. Biting the end of an expensive cigar is just dumb and it could ruin a perfectly good cigar which is a party foul so don't do it. It's best to cut about 1/16 or 1/8 of an inch in to the head of your cigar with a decent cigar cutter. The head of your cigar should have a slightly visible cap; see if you can find it. If you can see it just make sure you don't cut beyond that or anywhere near that to play it safe.
Lighting And Smoking Your First Cigar
It's best to light your cigar with wooden matches and if you really want to smoke like a pro you'll have some cigar matches made of spanish cedar wood on hand. A butane lighter will also do but won't look as cool. Those little butane torch lighters work well but you have to be careful to not let the flame hit the cigar. Once you have your lighting utensil, place the cigar in your mouth and bring the flame close to the end of your cigar. You don't want to actually let the flame hit the cigar you just want to bring the flame close to the end of the cigar and then suck the flame into the cigar as you puff in through the cigar.
As you puff on the cigar you'll want to begin rotating the cigar until the entire end is completely lit. If you have a big cigar yo may have to rotate it a few times. Continue puffing on the cigar with the flame lit until you get a nice easy draw. Most people don't inhale the cigar smoke you basically just lightly draw the smoke into your mouth, taste it and then blow it out.
The speed and pace that you smoke a cigar with is also important. You don't want to smoke it too fast because it'll burn too hot and that'll negatively affect the flavor. On the other hand if you smoke a cigar too slowly it may go out. You can smoke a cigar as far down as you like but at some point you'll notice a different flavor and that's when you can put it out.
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