Might be my last dumb questions

Answer me this. Is your pipe new? If it is an estate, the bitter taste could be oxidation. If thats the case check this out.
http://www.puff.com/forums/vb/general-pipe-forum/272622-cleaning-oxidized-stems.htm
As far as cake goes, just don't scrape the walls of the bowl with a knife or anything like that. If you must clean the bowl, use a pipe cleaner dipped in 151 rum, or any 80+ proof libation. The higher the proof the better. You can also twist a dry paper towel up and use it to gently wipe the bowl out. Hope this helps.

You can see the cake - the carbon layer inside the bowl.
You can trim down the cake when cleaning the bowl by using a reamer or the "spoon" part of a tamper or Czech tool. You shouldn't be using anything sharp inside the bowl.
As for the tongue touching the opening in the bowl, I think the bitter you are getting is normal. You just learn not to do it.
And don't be too impatient for responses - your OP has been there less than an hour!

I don't really pay attention to when it's formed. But you'll get a black build up in your chamber. I've heard some old timers around here say they used to coat it with some honey to build up a new pipe, but I've never tried that. Whatever pipe I smoke during the day, I clean it out when I get home with pipe cleaners. If there is some heavy build up I use a tiny scraper that I used to use to check spot welds on cars. Whatever works I guess.

You should clean your pipe with an alcohol after every smoke. I use rum, often the old tars are bitter. Some smokes are juicier than others, if you experience bitterness it can also be that you have too much fluid build up in the stem, just tap the end of your stem on your hand or better yet on a cloth, I often just use my pant leg and the extra will come out. But also as you smoke the tars formed can be bitter. If you are smoking a pipe that has an oxidized stem that will taste more like aspirins and needs to be cleaned. But in that case the exterior of the stem will taste bad and not just the end.

Cake happens. For briar that's a good thing, but for meerschaum and other alternate materials, it isn't.
The black carbon buildup on the walls of the bowl thickens over time, and if you're smoking the bowl all the way to the bottom each time, it should be somewhat even. When it gets too thick (I've read stories on here of bowls you couldn't get a pinky finger into because the cake was so thick) or uneven, you can trim it down. Personally, I use a simple reamer like this one from Cup O' Joe's. Other than a really abused estate pipe I got, I've only ever reamed one other pipe. It's not a weekly exercise, that's for sure.
On the bitterness, be sure to run a pipe cleaner through the stem after ever smoke. Deposits in the stem can make their way into your mouth and ruin a perfectly good smoke.
Simon

After smoking a new pipe everyday for about 2 weeks, lightly run your finger on the inside of the bowl. You will feel that it is becoming textured. Sometimes you will be able to see small bumps of carbon on the insides of the bowl. Cake is forming. Most seem to feel that a 1/4 inch of cake is ideal.

You should clean your pipe with an alcohol after every smoke

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I personally think this is over kill. Good use of pipe cleaners after - and maybe during - a smoke will handle this. Using alcohol to clean every now and then is all that's needed, in my experience.
I should have mentioned using pipe cleaners regularly in my original post in this thread. My bad.

I agree with Jud. No need to over do the alcohol. Unless it's the cocktail hour.

Bigvan said---No need to over do the alcohol. Unless it's the cocktail hour.
Now that mad me grin. Good stuff. :rofl:

Cleaning after every smoke will give you a pleasant experience every time. Just running pipe cleaners helps, dipped in alcohol all the more. And we mean just through the stem and shank, no need to wipe out the bowl unless you smoke something that you just hate, might be a good idea to fold a pipe cleaner in half and use the rounded part to pick up any loose ash or dottle. Cake will form and it will be noticeable, but it takes time.

The bitterness you are tasting may be the tobacco juices inside the stem. If you get your tongue a little inside that slot (that's what she said) you will get a bitter taste. Think bong water, but tobacco. ::
If your pipe starts to gurgle then be careful, a mouth full of this stuff is foul.

Bitterness could be the tobacco juices in the stem or if it is an estate with a vulcanite stem it could be oxidation. If it is an estate then you might want to soak the stem in oxyclean and give it a micromesh treatment. If it is juices in the stem maybe just clean the stem and shank with alcohol. I agree with the comments that alcohol is over kill but only if you are having no problems. Remember alcohol can take off stain so be careful outside the bowl.
The carbon build up will be black but don't worry too much about that. It will come with time. Ream the bowl with a paper towel and clean the stem with a pipe cleaner for normal use.

jsiddle, After reading this & some of your other questions (tongue-bite even though smoking slow, no flavour from your aro etc) I believe there may be one answer for all of them.
Your pipe is still new.
It can easily take 20+ smokes for a new pipe to start to behave itself and begin performing as it should.
I've just been reminded of this because like a damned fool I've bought 3 new pipes and am breaking them in all at once. Smoking my regular tasty, no-bite tobaccos in the same way I always do has so far resulted in me barely being able to tell which I was smoking & one day getting blisters on my lip. 8O Things are starting to improve now though.
Sometimes I'm amazed that any of us stick at this thing when every time we buy a nice shiny new pipe we have to endure this hell!!! :roll:

+1

You are going to get (and have already gotten) a ton of responses, some of them conflicting.
My advice?

Do NOT clean out the bowl while breaking in your briar. It will take 10 to 20 smokes for it to be broken in. The cake should be about the thickness of a dime or nickel, and once it's established you will need to ream it every now and then to keep the cake to the thickness. Do NOT be overly fussy about this -- just ream it when it starts to get thick enough to be bothersome while loading.
You should run a couple of pipe cleaners through the stem after every smoke, and sometimes even during the smoke. The bitterness could be caused by all kinds of things. Just cleaning the stem regularly should help it out. You do NOT need to thoroughly clean your bowl after every smoke, although some guys insist on doing it (I imagine that would hurt the build-up of cake anyhow). I've got dozens of briars and have been smoking for 20 years, and have never had a bowl burn out or go "sour" or rotten or whatever. Every few months, it's a good idea to thoroughly clean the bowl with alcohol (I use rum), which help keep it sweet and fresh. If it's tasting bitter or nasty, you might need to let it rest for 2 to 3 days. Some guys will tell you it needs to rest after every single smoke (smoke once a day, basically, and then let it lie empty for several days). I disagree. I smoke my briars multiple times a day without problems and then let them rest for a couple of days, which is how most smokers did it in the era of our fathers/grandfathers. You can get by with a rotation of only three briars, or just use cobs to fill in the rotation.
Anyhow, to sum up: Clean regularly with pipe cleaners. Once it's broken in, clean the interior of the bowl with alcohol every few weeks, and let it rest for at least 2 days after every day of use. That should really help with this kind of thing.
You're going to get all kinds of advice here. Take notes, and try whatever seems to make the most sense. I really wouldn't worry too much about it, though. Your briar is not a Ferrari or some high-performance machine that needs an oil change every five hundred miles! It is a TOUGH piece of briar wood that is designed to take punishment. Briar pipes aren't invulnerable, and you do need to keep them clean, but they aren't in any way fragile.

js, this is what I do after every bowl. I take a bristle pipe cleaner and run it through the stem, making sure it gets clean. I then take a fluffy pipe cleaner double it and run it around the inside of the bowl to even the cake and get loose tobacco. I blow out through the shank to get rid of anything loose that is left behind after rubbing with the cleaners. I then take as many bristle cleaners as it takes to clean the shank. I will double the cleaner to make sure it is scrapping the walls good and thereby cleaning the shank. After 5-7 bowls in that one pipe, I will then use Everclear, shank brush, bristle cleaners, stem polish and wax to clean my pipe. I have found that this system keeps my pipes tasting fresh and clean and I have never had a pipe go sour on me. There are lots of video's on how to properly clean a pipe, I would recommend watching them, pipe maintenance is crucial if you want your tobacco to taste great. You don't have to worry about reaming for a long time, but you will eventually need to get one, I use the senior reamer, it is the easiest to use in my opinion. You also need to invest in tons of pipe cleaners, bristle and fluffy. P&C has the best prices on the BJ Lngs which is what I prefer. I buy the 100 count fluffy and the 80 count bristle and I buy 500 plus at a time of each. I go through tons of these keeping my pipes clean and fresh. It usually takes 1 fluffy and 6 or 7 bristle cleaners after each bowl.