I wouldn't suggest using any common household items as lube. It might sound gross, but you can use your saliva. It's natures lubricant. As for the painkillers I don't see why it would be dangerous, but I don't see why they would be necessary.
you might want to go buy some lubricant... saliva can be handy but it dries pretty quickly. i'm not really familiar with that kind of thing, but i think they make special anal lubricant. i've never seen it, but i've never looked either... if not, i'm sure regular ky or whatever would do.. i wouldn't suggest butter or any other household products
I would stay away from house hold items too. There are some that could cause yeast infections in women. The best thing for anal play is anal ease or any kind of water based lubricant, either or KY or WET. Condoms are great for actual anal sex. Especially for the first couple of times. The condom can make it easier and once she gets used to it you can have regular anal sex. Be careful and take it slow. Anal sex can be lots of fun. But it can hurt a lot only if you rush it.
Buy some proper lube. Don't use any painkillers, with enough lube it does not hurt your partner. (all you need to do is to spend couple of minutes preparing for a proper anal sex). Alcohol acts as a painkiller, that should be more than enough.
First take the pain killers. Then drink lots and lots of alcohol. Lastly, apply the anal lube when she is starting to go into a slight coma and I promise she won't feel a thing... Jesus where are kids learning sex education now days... wait... your 20 and not a kid so thats even worse...
No seriously, go to a drugstore, wally world, Walgreens, whatever, and get some silicone based lube and a enema (might want to get them at seperate times if you get embarrassed lol. IF YOU DON'T GET EMBARRASSED, run to the pets area and pick up a can of cat food. That will have the checkout person really eyeing you then lol.
Silicone based lube is the best for anal sex or play (unless your using a silicone toy but then you can just put a condom on the toy). Waterbased lubes can cause internal discomfort if you are allergic to the ingeds (whatever that sugar crap is called gly something). To test it just put a glob of it on your finger and stick it up your hole. What 5-10 secs. If it burns like hell then you are probably allergic to it. Just relax and it will stop in a few mins. If you can't take it, just go sit on the pot.
Anyways, use the enema a few times and flush her out good unless you are into playing with poo (hey some people are lol). Tidy up. Use plenty of lube and mess around. Just go nice and slow with the playing so she can get used to the new feelings and learns to relax her ass. It will probably take a couple of times and days before you can do any major GNP on her ass.
P.S. Oh BTW, if she stuck a marker up her ass halfway without any lube AND enjoyed it, it ain't the first thing and first time she's put something in her ass
phonics - I <3 your scarasm! It had me laughing. =D
Anal is painful, i have to say.... so go slow on her at first and for a while! I also noticed girl laying on stomach isn't as bad as doggy style (that sounds so bad - but it controls how much a guy can enter too) and the best idea is use LOTS of lube or saliva.