DO NOT go for hookers.Even if you do with condoms, you can't get rid of STDS that spread through skin contact like warts.They are pretty fucking disgusting.
See link
http://en.wikipedia.org/wiki/Genital_wart
They might ruin your life forever.Just stay clean and wait for the right woman.Do not push it on her and wait till she is ready for that.Some women don't like anal so if that's the case, you need to respect that.Sex is something that should go on after both partners are ready for it.If one is not, it's a sort of rape.
There's no point worrying.If you are that desperate get a fleshlight butt.
It's the closest you could get for less than $100 and a long term investment.
http://www.fleshlight.com/fleshlight-toys/vibro/vibro-pink-butt-touch/
Try it, it gives almost the same feeling and hang on till you get someone with whom you could do anal.