i have been using a cupping set and love it! The nipples are stretching a little and i hope to see them longer soon. i would absolutely LOVE to be put on a milking machine! That would be great!!!! 

try a milkmaschine do it every 4 or 5 hours a day for about 20 minutes it will help and nipples will get larger after a while,it really works. i did it before

i developed blisters which were very painful and annoying to my master...i wouldnt go any longer than 10 minutes...but everyone's skin is different

I agree with just about all the advice above but we have found that women differ in how easily it is to blister the nipples.

We suggest pumping every day but not more than for 15 minutes at a time, in some women less, and not more often than 3 trimes each 24 hours.

Application of a nappy rash ointment helps prevent any soreness in many women.

Most important, in our opinion, is that you caress your nipples with oil or face-cream or your own arousal syrup a number of times a day. 

Further toi my earlier reply look at these for some ideas and more information about how to use the "O" rings http://forums.newart.com/phpbb/viewtopic.php?t=22946&start=75 the best pictures illustrating this are about 2/3 the way down page 6

Vaccuming is the right way to go here. If you leave the vaccum on it will cause the skin and tissue to stretch. If you use o-rings or something of that sort be sure NOT to leave them on for extended periods of time or have them to tight because they do cut off blood flow and can cause serious injury to the body part involved. Standard rule for applying a turnicate (such as o-rings or tied body parts) type device is to loosen the turnicate every 10 to 15 mintes to allow the blood to circulate. I have seen longer periods but it's better to be safe then sorry and have a nipple go dead or have to be removed because of tissue damage.

I've found these to be quite useful....one of my nipples was a definite 'innie' and now it pops out very easily!!

 

https://www.nipplefunwear.com/index.php

 I suggest starting with the shorter ones but ordering the longer ones as well...that way when you fill up the shorter ones you are ready for the longer ones.

 The site is very informative as to how to use them as well!

 Have fun!

Hmm... ok. I can definitely try that!

Do you know if you go longer then 15 minutes does that help or hinder or really not make any difference?

yes the longer the better, be careful not to induce "water blisters" though and if you do it several times a day you can also induce lactation. You may find useing rubber "O" rings round your nipples to keep them, long for a more extended period helps too!

I have heard the same excact thing about using a "Snakebite Kit". I read somewhere ( I forgot where? ), that if you use a "Snakebite Kit" on your nipples EVERY single day for like 6 months straight, then eventually your nipples will become longer and/or fatter from the daily "Snakebite Kit" usage.

HeadMaster way works,but like he says:It takes time.

    my masters have used a snake bite kit on my nipples,it did streach them quite far,it didn't last, they have just always used rings that fit around my nipples and or tying them for long periods, i am sure that has made them longer,