I love sketching digitally! I do everything digitally to the point that I don't like doing traditional stuff. It also saves me money since art supplies are expense and I need to spend money on other things instead D:
EDIT: I FORGOT TO ADD A SUGGESTION. I think just doing it over and over is a good way to get used to it. There's no need to spend money on a Cintiq! (or try to get one that's second hand, they should be cheaper that way)
I use a pencil brush in Photoshop (on a wacom tablet) that replicates the experience and tactile feel to an incredible degree. The only difference is I'm looking at the screen rather than a piece of paper. Add to that the ease of erasing, resizing and distorting, digitally sketching is a no brainer for me.
The cintiq part was a joke but I don't want a cintiq for 1 reason replacing it. I currently have an Intuous Pro and I like the fact that I can draw from a distance or just pay a few bucks and get a cheap replacement. I think I should probably get a monitor instead of using my small laptop screen.
So I decreased my problem some what by doing this.
Thank you all for the help. I'm going to focus on using one software and see how that pans out. I'll post the illustration I tested this on if anyone wants to see it.
I updated already still feels the same, I like having my pencil as barely visible as possible so I can layer my sketching. That's what I do traditionally
I'm accustomed to sketching in Paint Tool Sai or Photoshop, depending on what stage of the page I'm in.
It's a matter of practice: I found it extremely awkward when I started.
Gosh. I have the opposite problem. I'm so used to sketching digitally that I feel weird when I hold a pencil. I got so used to drawing digitally that my traditional work is so... 'meh'.
You could change the settings on your tablet (like changing pressure sensitivity) or experimenting with different brushes in order to get a feel for something you like. 
But aside from that, practice goes a long way.
Getting used to sketching digitally took me a long time. It feels very different from sketching with a pencil, that's for sure! I feel most comfortable sketching in SAI, too, out of all of these programs - though that's all I tend to use it for these days, since I've made the switch to Manga Studio.
I do have a cintiq, which helps a lot - but even with that, it took me months to get used to it, so it's not really about which tablet you have, but how much practise you have.
That's important. Avoid the pure white backgrounds for digital sketching/drawing. They just "burn" your eyes.
About the cintiq issue for those who are thinking about get one, but they don't want to sell their souls to the devil because of the price, in addition to look for one on ebay, there are some more affordable alternatives like yiynova or bosto (i've got one).
I've had a wacom tablet since middle school snd now im 22. I've been drawing on them ever since. It still feels weird and awkward I can sketch a lot longer on paper than on computer I don't know why. 1
it may help if when /sketching/ you use a certain kind of brush/pen texture. i have a pencil setting on sai that makes sketching and drawing feel more natural.
i have to admit, theres something really nice about drawing on paper that sometimes i miss, but the undo button beats it every time.
Well even the alternatives cost quite a bit morethan an intuous. I am well aware of alternative cintiqs but wacom has that patented technology which does not require a battery powered pen. In addition driver dupport is something that worries me about these cheaper alternatives .
But those brush textures dont they just make it look more like real drswing not feel like it? I rarely use undo when sketching digitally just like how i don't erase tradtional sketching.I use erase not undo. I find doing undo very limiting in creative flow.
I haven't ever had a problem with sketching digitally. It definitely feels better in SAI but I used to do it in Photoshop CS2. As long as its something with pressure sensitivity.
I had trouble inking digitally until I got a tablet screen PC, because doing the very detailed work would always frustrate me when I'm looking at the screen instead of at my hands. For a while I actually printed my digital sketches on paper and inked them by hand. So my experience was pretty much opposite of most people's, b. ut maybe I'm just weird like that
This is what I'm using right now:
It's a convertible laptop that behaves like a tablet when it is closed, but the screen has actual pressure sensitivity and uses wacom drivers. It is definitely not as good as having a cintiq, but since you can pick up a used one on Ebay for like $150 it's not a bad tool.
Up side: it is portable, you can travel with it and have all your art supplies and computer in one piece, plus it's cheap.
Down side: the memory is very limited, so working on large files is heinous to impossible (I work at 600 dpi with no problem but if I go higher, it crashes). The HD space is pretty negligible, too. I couldn't store music or anything excessive on it aside from my art files.
I'd pay good money for an updated version of this kind of computer with more power, but I think maybe they went out of fashion since the Cintiq became accessible, because I haven't been able to find one. I'd definitely rather have a cintiq to use with my strong desktop computer, but it's not in my budget.
Anyway, using this made inking more of a breeze. I like looking directly at what I'm drawing.
@ghostnxs Oh, okay! I found sketching on a regular tablet awkward, I know that; I had one for years, before I upgraded to a cintiq. It wasn't until the cintiq that I felt really comfortable sketching digitally - but when I went back to a regular tablet (like, when drawing at school), I found I was more comfortable with that than I'd been before the cintiq.
I think it's all a matter of finding what works for you. If changing the colour of the canvas/brush works, then go with that! I know I always feel more comfortable when sketching in blue or red than in black.
It's a matter of habit, I guess. I've been doing digital art for well over a decade, with tablets of different sizes and make. I'm pretty used to sketching digitally, whether it's an Intuos or a Cintiq. I feel like inking is more troublesome digitally though. I'm tempted to try Faith Erin Hicks' way of doing the comic pages by printing out her sketches and inking them, but I neither have the time or the facilities >_>
I find it odd that you dislike Clip Studio more than Photoshop. The only reason I finally switched from SAI to Manga Studio was because it felt the same while having more features. Photoshop is incredibly awkward for drawing for me, though Kyle's Brushes help with that. (I'd also suggest Frenden brushes for Manga Studio: D)
I kind of agree, as I sometimes feel weird sketching digitally as well. This often results in me making a lot of mistakes and bad decisions on whatever I'm working on. I get used to it after a bit of warming up and practicing though. I also agree that SAI is the easiest to sketch in...
The awesome thing about digital media is that it's easy to correct mistakes if something doesn't look right. In the end my digital works usually look better and more refined than my traditional stuff.
I felt that way a few years ago and I thought traditional would always be my forte but now it's the other way around. Now I find it more comfortable to sketch digitally.
Although I still draw traditionally, it doesn't feel the same as before. Now that I'm digitally based I realize what a pain drawing traditionally is. The erasing takes up time, you have to gather all your materials and find good lighting and you got to be extra careful with ink. Not to mention always having to scan things :/
The best thing you could do is find a brush that emulates the type of tool you use and practice. Soon enough your hand will be used to all the strokes and it'll gradually get easier.
