Very complex subject stretching. Soreness may depend on a few factors such as: how long you've been doing it, your physical conditioning, technique, post stretching activity, supplements and any injuries you've had before.
As for how long you've been stretching, generally the newer you are at it, the more sore you'll feel the next day. This kind of goes hand in hand with physical conditioning.
Technique is crucial. You should consult a manual or video to show you exactly how to do it, if you haven't done so already. "Bouncing" when stretching, also called ballistic stretch, can actually do harm and cause small and numerous injuries to various structures. Over time, this can lead to restricted range of motion. So you definitely want to make sure and NOT BOUNCE during the stretches. Take it slow and be sure to keep breathing throughout the movement. There is no need to try and force the stretch in my opinion, since this can actually have a negative effect in the long run on various structures.
For post stretching activity, be sure and drink PLENTY of water every day, but most importantly after stretching. Stretching can loosen waste material from cells and tissues and if there is not enough water in the system can give increased soreness and a similar feeling of "hungover". This is the result of the waste toxins not being eliminated if there is not enough water to flush them out. Stretching should not cause immense soreness, but should let you know that you've been doing something.
As for supplements, you might think about adding some vitamin C after your stretching workouts since it can reduce lactic acid buildup, scavenge free radical by-products of wastes in your blood, and help in repair of tissues.
If you've had injuries before, you should definitely take it easy on those areas when stretching. Injuries can cause the fascia (cobweb-like structures that hold muscles and other things in place) to heal in a different pattern than they were originally designed. This can cause adhesions and limitations in range of motion. So take it easy on any muscles or joints that have been injured significantly in the past.
As far as stretching goes, I stretch for a VERY long time before I work out. I don't push it, I just make sure everything is warmed up and moving with as little resistance as possible. Even on days when I am sore I still stretch as much as possible, perhaps more. Depending on what type of stretching you are doing it will somewhat depend on the need to stretch on "off" days. However, there is nothing wrong with doing a little stretching every day provided there is no reason that it shouldn't be done.
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