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.

Now it’s time to let him push that cock inside your ass. Personally I have one big anal orgasm upon taking his whole length, lots of small constant ones while being anally fucked and one giant outer body one when he cums. Not everyone is the same. A friend we often play with has 2 or 3 medium ones while being anally fucked and a big one when he cums in her, but none upon being filled at the start.

You’ll want to be on your back, knees up towards you with ass very well lubed, make sure to lube up the inside of your ass as well. Let him play with your ass for a while, make sure everything feels fine – if it doesn’t put it off for another day and train your ass some more. If everything seems to be fine move on ahead.

Have him plaster his cock with lube and rub it’s head against your asshole. Spread your cheeks with your hands for him so he can better see your asshole, it’s going to be very slippy down there so the more help he has the better he’s going to be able to push in at a good angle. Mentally this will also make your ass feel more open, I have no idea if it does actually open your ass up more but every little helps.

Have him push an inch in, leave it there for a while, remove it, wait 30 seconds, push a bit more in, leave it for a while etc. It’s a good idea to play with your clit as he does this to help you relax. Eventually he’ll have pushed his whole cock in, let it stay in for a while and play with your self before he removes it, and then pushes all the way in in one slow stroke (this is the bit I normally have a damn good anal orgasm).

Now have him begin to slowly fuck your ass, small thrusts and nothing more – your don’t want most of his length leaving your ass and being pushed back in yet. Always communicate, if your saying nothing he’ll begin to ask if your okay and men’s nervousness can ruin the mood. If it’s good ask him how it looks seeing your ass stretched around him, tell him how big his cock is in your ass, how you love being filled by his cock and all that. If he’s going too fast or too deep tell him.

Even though your the one being ass fucked, for the first few times you also need to be one in charge. Tell him when he can fuck you a bit faster. For the first time I’d stay in the missionary knees towards you position and always suggest starting in it for a good while. Whatever you do make sure he cums in your ass, condom-less feels better as you’ll get to fill his cum hitting the walls of your ass and flooding you but if your having safe sex still keep him in there as the pulsing of the cock as it cums feels fantastic.

After he’s came and you’ve both recovered it’s time for him to slide out. Even after years after buttfucking this bit still feels weird so prepare yourself. If your not using a condom it’s time for the not so fun bit (unless you have a kinky friend who’s thirsty) of going to the toilet and pushing that pint of cum out your ass.

After you’ve had anal a few times (continuing to wear the bigger plug throughout the day) you can try other positions. As stated before for your first 20 or so times I suggest you always start with you on your back and then change to a new position. On your side with him kneeling behind feels really good. Doggy feels good and looks really good for him but your ass will be tighter in this position so take note! If you want to make him cum his brains out looking over your shoulder and saying something like “I want you to pump my ass full of your seed” as he’s getting close to cumming will do it. Doggy also allows you to play with your clit really easily as well, though if you’ve never squirted before this might change that!

However I find the best position is girl on top squatting above him and really fucking him as hard as you can. Save this position towards the end as it’s hard to do for long periods of time. Not only will this make him blow his load in a few strokes it also allows you to really feel him cumming. As he cums drop your ass onto him hard so he’s balls deep and the feeling of his cum shooting into your ass with drive you wild. Just make sure to stop yourself from falling as it can make you light headed.

If you have any questions about anal, be sure to ask me.

This guide was written for a M/F couple (with instructions to her – didn’t really notice that until I finished mind) but of course can be used by M/M couples or M/F and F/F couples where she is penetrating.

Although poo is much higher up than most penises will go there is a chance that he may get some on him. It’s always a good idea to nip to the loo a few hours before a buttfucking and personally I use a Douche to clean my ass with warm water on occasion.