okay, i know this is the anal sex thread, but because you mentioned olive OIL, i feel the need to mention this here and now.
DON'T USE OIL WITH CONDOMS EVER (evAr)!
Google for "oil-based lube condom"
Here are two links that came up. Please read for an explanation since I've had a little to drink and don't feel like explicating.
http://www.mypleasure.com/education/...estions/18.asp
http://www.coolnurse.com/sex_faqs19.htm
And this is important why? Because you should always use condoms when doing anal. Always.
WHY?! Google "anal HIV"
http://www.cdc.gov/hiv/pubs/faq/faq22.htm
I'm too lazy to find a link that properly informs you of my point, but my point is this: You are more susceptible to transmit an STD to someone receiving anal than with any other orifice because of how the anus/rectum/intestines function. BE SAFE.
I will go pass out now.