I found this on a website.
Here's How:
Relax! Try not to worry about inserting the tampon right the first time. If you are tense it will make insertion harder.
The best time to practice inserting a tampon is during the heavy part of your period. The tampon should glide inside your vagina easily without any discomfort.
Decide if you prefer to insert the tampon standing or sitting. If sitting is your preference, sit on the toilet. If you want to try standing, putting one foot on the bathtub helps.
Hold the tampon applicator in your right hand if you are right-handed, or left if left-handed.
Use your thumb and middle finger to hold the bottom of the larger, outer tube.
Point the tip of the applicator toward your vagina, facing slightly towards the back. The smaller tube should be pointed away from your body.
Use your other hand to open your vagina.
Place the tip of the applicator at the opening of your vagina.
Gently push the smaller end of the applicator in until it is completely inside the larger outer tube. This pushes the tampon into your vagina and out of the tube.
With your thumb and middle finger still on the outer tube, release the smaller tube and let the strings dangle freely.
Gently pull the two tubes out together.
Dispose of the applicator according to the manufactuer's instructions.
When you are ready to remove the tampon, gently pull the withdrawl strings down and forward. The used tampon may be flushed down the toilet.
Tips:
Lubricating the rounded end of the tampon with a water-based lubricant such as K-Y Jelly can make insertion easier the first few times. Don't use petroleum jelly.
Always read the manufactuer's instructions throughly before using any type of tampon.
If the tampon feels uncomfortable it is probably not inserted far enough into your vagina. Try again with a new tampon.
http://womenshealth.about.com/c/ht/0...0965684522.htm
I'm really getting embarrassed now... 
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