I'll always maintain that if a guy wants to play with a girls ass then he should try his own out first. Seriously!
Two reasons, 1. You'll have a good idea what you need to do to your lady, and what not to do! 2. You'll learn how you both can enjoy anal. Below I've copied a post I made elsewhere in response to another 'anal' question, first I'd like to add a little and expand.
The reality is the ass is a sensitive area and has muscles in that are delicate, force them and they'll hurt and you damage the tissue around them. Do this to your girl or yourself and you'll be put off for a long while.
It takes a lot of working starting very small with loads of lube for the first timers. LOADS of lube! Did I mention f**king LOADS of lube!!! Even those (myself included) who play with their ass all the time or regularly have anal sex can't always get things in like you can with a pussy.
My best advice is to try and start with a slim vibe, maybe during or after vaginal sex. As mentioned already you have to be 100% happy with your partner and trust them implicitly. And stop means stop!
During the good times with my SO, anal sex was regular, probably 8 times out of 10 times we had any sex. And we'd be at it several times a week, so even then with what you could call a 'trained' ass we'd still need to work up with either a vibe or a finger then 2 then 3 etc. AND LOADS OF LUBE!
Doggy position is best I've found. Use plenty of lube (did I mention that) and start small and work up, you may have to take an hour or more, or not even get to taking a cock the first time. One trick is to find a vibe that you're / she is comfortable with in her arse, then in doggy position have vaginal sex, as he pushes he'll also push the vibe at the same time, this will get you used to the in-out motion and also used to the depth of penetration, another issue to consider. The depth you take will alter with the position you are in. Also with the vibe he'll get as much fun as she gets.
Doggy also allows for her to push back onto him, very good for first timers or getting back into it. Also girl on top allows her to control everything. Try using vibes and toys first, starter or trainer kits with a slender vibe (the vibrations obviously add pleasure but help things relax), try butt plugs, sometimes it takes a while just to get used to the feeling of something in there.
And for those worried about mess, think about! If your getting to the time of day your needing to go then, well.
Clean, clean, clean! Get an anal douche maybe. If you not used to playing with your arse then this could be a bit difficult to start with but using a neutral soap (nothing too perfumed) or shower gel, or even a moisturiser. Start cleaning around with your finger, then using the soap as lube slide a little one in a touch, this will help clean and relax your ass. When I'm getting myself worked up for some arse play I take a long shower and use a shaving gel (I normally shave down there first) and use that to clean my ass as it has great lube qualities, often I can get a couple of fingers in there, loads of gel and loads of rinsing ands then a little moisturiser.
Maybe for some it could be a good idea to try playing with your arse while alone in the shower, relaxed, warm and wet with loads of gel type soap, squat down a little and try inserting a finger or suitable smooth toy or waterproof vibe. Take things easy and at your own speed.
Anyway, here's what I wrote before:
Well, first up is getting things in there. The anus needs some warming up, you can't just go slamming things in there.
And it needs lubrication as it doesn't produce anything like what the pussy does.
Forget what your seeing in porn films, that's all BS.
Anal is different for different people, some won't even consider the idea.
The anal area has many nerve endings and can (and does) respond well to stimulation.
I can only go off what I have experienced with a woman, but when done right i.e. in time and working it up slowly with loads of lube, they can enjoy it just as much as vaginal sex. Sometimes more, apparently orgasms from anal are very different!
As a guy I like my ass played with, I use toys and in the past have had strapon sex. Again, you can't just go whacking things in there, you need to start small and use lube, loads of it.
When you hit the prostate you really find out about male anal play / sex.
Tip for the guys, if you want to try anal with your woman and she's new to the idea too. Then try playing with your own ass first, maybe in the shower. You'll get an idea then of what it's like to get in there.
If you go in too fast and heavy with your woman you'll hurt her and put her off for life.
If your starting with fingers, trim your nails. Try getting a slim vibe, this WILL work wonders.
Anal play is amazing for both of you and it should be reciprocal.
Tip for the ladies, if you want to wow your man during oral or a handjob, try sliding a well lubed finger in there or a slim vibe.
And if you are a girl that likes cum, this is a sure fire way to increase his load.
For me it not only feels tighter but it can 'grip' in a different way, hard to explain really. I enjoy it when the head of my penis is sliding back and forth through the sphincter muscles, this can really get me there quick.
Additionally there is the psychological 'taboo' 'dirty' sex thing too, sometimes this heightens the intensity for some.
Overall it is just a way of gaining more pleasure for both out of sex. Note (for guys) BOTH!
And guys, seriously, some of you need to loosen up and let go of your hang up's. Let her play with your ass, you won't regret it.
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