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If it goes in all the way (you pushed the applicator in you and then you pushed the little stem in...it is in properly. Maybe you should try a different brand. The Playtex Sport style is fantastic!
Also, leakage always seems to happen from time to time with tampons
It may be best to wear a very light pantie liner just in case.
Also, taking a tampon out, in my opinion is always worse that putting it in. It does feel kind of awkward doesnt it? The best thing to do is deep breathing stare a single object and take your time removing the tampon. Rushing will make it really hurt. Treat your body right! 
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How do you put in a tampon correctly?
 



How do you put in a tampon correctly?
Hi, I have had my period for about a year now and pads are really starting to bug me. I tried putting in a tampon a couple times and I could still feel it. I heard you weren't supposed to so I was wondering if I was putting it in wrong. Also, after about...
two hours my tampon leaks a lot even if my flow isn't heavy. I was wondering if that was also another sign that I'm not putting it in properly. When I go to take the tampon out, even if it's fully soaked it still really hurts, probably more than a tampon should. Any advice?