I'm pretty flexible for a guy who's 6'3 and 101kg (222 Ibs), although I can't do the splits yet, but I'd like to one day. I
don't know how but I've always been naturally flexible... however, a physiotherapist told me that's a bad thing as it can lead to injuries a bit easier. This could be how I've hurt my muscles in my back twice and tore my right ACL (the centre ligament inside the knee). But lately I've put on a lot more muscle which can prevent such injuries, or at least reduce chances... but while I'm still decently flexible, I'm not as flexible as I used to be. Flexibility is important in Judo.
On the flip side, my flexibility once saved me in a Judo competition. I fought a former wrestler, he grabbed me in a head lock, bent me over backwards while twisting me. The video footage looks horrific, somehow though my spine didn't snap and I ended up beating the guy in the end. It hurt like hell at the time.
As for stretching, I like to hold each stretch for thirty seconds. I do it to the point of discomfort, but not pain. If you feel "pain", reduce the stretch. What some people like to do is hold the stretch for thirty seconds or so, then stop and relax for about five or ten seconds, then do the same stretch again for another thirty seconds, but this time stretch a little further. I stretch maybe five times a week, always before exercise, but some people do it daily, and even twice a day. Is this bad? I'm not entirely sure.
There's a few stretches you could try...
One stretch you could try is sitting on the ground, in a sort of cross legged/mediation position, but don't cross your legs. Basically, take hold of your feet with your hands and make sure they're close to your groin, or as close as you can. With your elbows on your knees, try and push your knees down to the floor, as far as you can. When your knees can touch the floor, you can then go further by keeping your back straight, shoulders back and leaning your torso forward, like you're trying to bend down toward the floor. The goal of that is to get your face as close to the floor as you can.
You'd know what a lunge is right? The leg exercise? You can do a stretch where you lunge forward, but the leg behind you, don't put your knee or shin on the ground, instead keep off the ground and try to lean forward as much as you can. Keep your back up straight and your hands on your hips. When you get better at this stretch, you can go further by putting your forward leg even further.
There's one stretch which is hard to describe, so I'm sorry if it sounds retarded. One of the instructors at the Wing Chun club I used to train at called it the dolphin stretch. He said he used to do that stretch back when he did Taekwondo, to help prepare for the splits. Sitting on the floor, one leg is out forward and one leg is out backward. Your forward leg is bent at the knee and is flat on the ground, and your backward leg is also bent. In a sense, it looks like a 'running stance'. Your back is also up right straight, hands on the floor. The idea is to kinda try and get your legs stretched out as far as you can, eventually slowly getting your legs more straighter and less bent.
Couple of other quick ones.
Stand up straight, extend leg forward onto something (like railing, a table whatever), reach forward for toes, lean torso forward and stretch. If you have someone with you, you can do this stretch by having them squat, putting your heel or calf over their shoulder, then they slowly start to stand up and bring your leg up higher. When you feel the stretch, get them to stop in that position and hold.
Lie down on the floor. Bring one leg up into the air aiming foot at ceiling, grab the back of your knee (back is still on the floor), bend your foot back to feel stretch, relax forward, repeat.
Again lie down on the floor, bring one leg up but bend your knee as much as you can. Take hold of your knee, and try and bring it up as close as you can to your body, aiming for your chest. When you get better at this one, do it standing instead.
Keep doing the current stretches you're doing too, but just bump the stretch time up to thirty seconds instead. Think about doing a second set of stretches too - hold for thirty seconds, stop and relax (for five to ten seconds), then do the stretch again by try and stretch a little further.
I don't really want to do this as it'll be kinda weird, but if my descriptions suck, I can upload photos to try and help.
As for time... I have no idea. I guess really it'll depend on how often you stretch (how many times a week, how many times a day) and how long you hold each stretch for.
Good luck.