So I know nothing about anal sex...

Helpful topic info on Anal Sex:

How regularly do you and your partner engage in anal sex?
Regularly? Whenever the mood strikes? Never?

ANAL OR NOT???
I HAVE CAME ACROSS A LOT OF WOMEN WHO DOES NOT LIKE ANAL SEX.WHAT WOULD YOU PERFER ANAL OR NOT?

Any embarrassing anal sex stories?
I've heard a few horror stories but have been pretty lucky

Good toys to warmup for anal sex?
After searching through the topics, I haven't really found much related to this. What are some good toys sold on EF to warmup for anal sex? I'm...

how do u prepare for it?
what is your routine to get urself clean b4 engaging anal sex?

Wife and I were off and on about getting into anal play for a while. Let me tell you once we did we never looked back. We started with plugs, which not only give enjoyment for the back end, they also enhance regular sex while left in. Actually me wife will now rarly have sex without a plug in. Also role playing changes, sometimes my wife will strap one on and give me the pounding. Like I said we are a pretty normal couple that were worried about trying the anal stuff at first but boy did it change our sex lives. Go for it and have fun!

Relax, use lots of lube and be patient. Regardless of you you are using a single finger or a 3 inch plug these basic rules always apply. You the saying that "shit happens?" Well with anal play this is simply a fact of life. You can greatly reduce the chances by taking an enema an hour or so before play time and you can also wear nitrile gloves as well. Having a towel handy is always a good idea too.

Your butt is designed by nature to push things out. So anytime you try to put something in it will react and try to expel it. Think of of it as a gag reflex in your butthole. Once you get used to a finger or two, a small dido and even a butt plug your butt will stop trying to push these things out immediately after being inserted.

When you first begin and as you increase the size of the toys that you use you will get a feeling like you really have to poop. As long as you did your enema and waited for the "second wave" (a whole other thread in itself) you should have no worries. This is where relaxing and enjoying the feeling counteracts the panic of thinking you have to go to the bathroom. You will most likely try to go anyway and sit there with nothing happening except for maybe a little bit of lube leaking out.

Find toys that you will be comfortable using. I HIGHLY suggest silicone, metal or glass toys for anal play so they can be cleaned without worrying about harboring any unwanted germs. There are shapes and sizes in all of those materials to fit any budget and butthole out there.

There are a lot of us on here who enjoy anal play A LOT. I used to be weirded out by the idea of sticking things in my butt and now I am using a 2.5 inch plug during playtime. We all started out somewhere and if you ever want to anything you don't feel comfortable sharing with the general public you can send me a message on here any time.

Books. Library. <3

Tristan Taormino films are excellent anal resources!

Think about what your plans are. Some people go into anal stimulation with the intent of having penis-anal sex or harness/dildo sex, others just want to play around with small toys. As people have noted there are different types of toys: plugs generally stay put and give you a full, "bumpy" feeling (they do move around a bit). Probes are thin, long toys that can be thrusted, and the you can always use dildos as well (provided they have a flare, otherwise they can get away from you).

Anal play doesn't even need to include penetration. You can use a vibrator or finger rubbed around the outside of the anus. If you want to play around with anal stimulation, fingers are still a good way to start. No matter what lube is your friend, as it makes any sort of anal play safer and much more fun (even external stimulation).

There's a Tristan Taormino book called The Ultimate Guide to Anal Sex for Women that's a great resource for anyone, and it is tasteful and doesn't have pictures of naked people or sex acts, just some line drawings. It covers just about everything for both sexes, so I have no idea why they put the "for women" in the title.

I'm also going to pitch in that even if you don't use condoms for regular sex with your partner, it's even more highly recommended and some doctors insist that it's mandatory to use condoms for anal sex. Because your anus is not self lubricating, there's more of a likelihood that something might tear (although lube and going slow should lower this risk significantly). I especially remember the early days when my boy pulled out and I sat dazed looking at the bloody condom in awe and pain. We should have been going slower but I'm a masochist so I was kind of asking for it and while we agreed it was hot, we learned to listen to our bodies more. Apart from any bleeding though, the anus has different bacteria than the vagina and the risk of transmitting things jumps significantly. Even if you're fluid-bonded, I recommend a condom.

It is also good to note that he should not double dip. Or go between your ass and another hole. Oral to ass is fine. Pussy to ass is fine. Ass to pussy or ass to mouth is generally a bad idea. There's some argument if this is an absolute no or more of a guideline in order to avoid vaginal infections. Most of the infections you can get from it are minor and people tend to make a bigger deal out of it than I think is necessary but it's better to be smart than sorry. If he's going to go back and forth (or she for that matter), they should change condoms.

Lube. Going gently. If he's having trouble entering, it helps to push a little bit as if you were making a bowel movement, which tends to open the sphincter up and can actually make initial insertion easier. It's a little counter intuitive and it's just that little bit. Continuing to do that will let him in, but push him right back out.

Do not use numbing agents. Some people argue that it lessens the pain but the pain is your body telling you something. It's like turning off the fire alarm system because you suspect there might be a fire and you don't want that annoying noise. Listen to your body. Relax and work through it.

I know I just made it sound like a lot of pain, but it's different for everyone and it's very rewarding! I wish you luck.