Even today anal is still a bit of a taboo, more with the older generations then the younger but most girls will simply say "No" to anal and that'll be that, which is a great shame as I think anal is probably the pinnacle of all sexual acts and a sign that a couple love each other enough to do it correctly.
Anal takes a lot of trust, communication and knowledge of each other's body language to do right, but once you've felt the amazing feeling of balls resting on your butt cheeks as his cock throbs, filling you with his cum that you can actually feel hitting the walls of your ass you'll wonder why your not being buttfucked every waking moment.
This is a guide for men, women and couples into how to get started. Anal sex is not for one night stands in my own opinion, so I'm assuming you know the person you doing it with well.
Being an anal lover a lot of the things here I no longer do. I wear a buttplug most days so he can easily fuck my ass when the desire takes him (and it feels amazing knowing that no one knows you have something in your ass while at work). It's not uncommon for me to come back from work, take my bottoms off, kneel on a chair and tell him to lick and fuck my ass. Feeling him cum in my ass gives me such an awesome orgasm my head goes light as if it's some kind of outer body experience. For newcomers I recommend using a buttplug the same size as his penis though I personally use a slightly smaller one as I like the tiny twinge or pain as his head pops into my ass, and the feeling of him stretching me as he slowly pushes his full length into me.
Anyway, onto the guide...
First your going to need to go shopping. Lube is important, the first time we tried anal (all those years ago) we didn't use it - to say the least it didn't go well... Personally I use Liquid Silk. It's not too goopy, plays nice with toys and has the staying power. Sadly it's also one of the pricier ones out there. Some shops do lube specially for Anal, no idea what the difference is but if the price is right it also does the job.
Your also going need some buttplugs, I suggest getting 3 different ones but you could probably get away with 2. You want the smallest one you can find, one a bit bigger, and then one about the same width as his cock. Make sure they all have flared bases.
You should start "training" your ass about a month before getting fucked in it, it'll make the experience a lot more enjoyable for both parties. I find the best way to push a buttplug up your ass is too place it on the floor, lube it and your butthole well, and squat over it, lowering yourself onto it, and then pushing it fully in with your hand. Don't push it in in the tampon insertion position - your ass will be too tight.
Wear (when I say wear I mean have in your ass) the smallest buttplug for at least 2 hours a day for about 4 days. Then move onto the next size up and wear that for as many hours a day as you can for a week or so (9 days should do it). During this time make sure he plays with your ass a lot. Have him eat you out every night and get him to lube a finger up and play with your ass, lightly penetrating it and towards the end of the week pushing his whole finger up there (feels especially good if he does it just as you cum).
However I have discovered that not everyone's asses like fingers. No idea why but if your one of these people get a slim dildo. Nothing big (and nothing too floppy as this will make pushing it in harder) and use that instead.
It's now time to wear the biggest buttplug. If pushing this in hurts stay on the previous one for a while longer. Wear this buttplug for as long as you think you need to. When you can push it in easily for a few days have your man push 2 well lubed fingers into your ass (have his fingers lightly overlapping, not side by side). If this causes no discomfort (or very little) have him finger fuck your ass while licking you out as many nights as you can.
Note: All anal finger fucking should take place with you on your back, with your knees up towards you and without a buttplug in you.
