Anal sex

Well, I'll try to give you some tips that once helped me very much.
The first thing is always a good anal, non-numbing lubricant. It's really very-very important. Then start with a small butt plug which will gradually stretch the asshole and allow it to adjust to the feeling of something inside it. The next step would be slim anal dildos to acclimate to penetration and thrusting. And then, when you are ready you can move up to your partner's penis.
I'd say the key is to learn to relax the muscles when you're getting ready for penetration. If you can do it with a toy, it's likely that you will be able to do the same with your partner. Reply

If someone hasn't already told you, the key is to push gently OUT while he's pushing in... that relaxes things...strange as it seems Reply

Agreed.
My rules for anal play are:
1. Lube
2. Relax
3. Communicate Reply

Excellent points already made. You can never have too much lube for anal sex- reapply often! Reply

a) LUBE LUBE LUBE (ie, I agree)
b) You don't have to start with a toy or a plug. Have your partner glove up one of their hands, add some lube (and then maybe a little more), and try rubbing the anus. Then, slowly and gently, push one finger inside of you. Work it in and out. Once you get accustomed to that, then you can work up to two, three, sex toys, penises, etc. Just remember, starting slow and small, and wanting more, is WAY better than starting too big and just hating it out right!

And I agree with Jimbo. I mean, we all know my slogan: Communication is key! Reply

The keys to a pleasurable anal play are RELAXATION, PATIENCE and of course LUBRICATION (the more - the better).
If you're intending to combine anal fun with masturbation then there's nothing better than exploring anal area with the tip of you finger, by rubbing it against the rim and afterwards slowly (VERY slowly) gliding the finger in.
In case you want to try that with your partner I would still recommend you to try it first by yourself, so, when it comes to "action" there won't be any "surprises" for you. You already know what it's like. Been there, done that.
And as both, Jimbo Jones and Essin'Em mentioned, if you do it with your partner keep saying (otherwise giving clear signs) whether you like what or not and what you like and what you don't.
If you looking forward to use anal toys, then anal beads and plugs for beginners would be the best choice for you. (and never forget about the lube)

Wish you a good time.
Reply

Compared to any other new exploration, everything lies, first of all, inside your mind, desires and fantasies merge with social taboos and personal moral rules. Listen to your instincts, they will tell you what to do.
However, luvrication is a MUST at this point. Reply

When doing it with a partner there's nothing more important than communication. Communication is key! - Essen' Em is definitely right. Reply

Some really important info already, but I have one little tip for you too. This isn't key, just a tip. A vibrating toy can really help if you're having trouble relaxing your anal muscles or just want some added pleasure. Just make sure that you pick something with a flanged base if you're planning on inserting it. I like to just slip a vibrating bullet into the finger of a latex glove (cheaper than wasting a condom) and just using it to massage the area as a good way to warm up to anal.

Also don't forget hygiene, condoms are a good idea with anal play unless you are using a toy that is pure silicone and can be sterilized (metal and glass can also be sanitized by boiling or dishwashing). Condoms are always important is it's a penis that is doing the penetrating, there's risk of UTI, and it's always better to be safe than sorry.

Have fun and play safe! Reply