Tips for anal penetration?

Contributor: cbmb716 cbmb716
Related to: 
My fiancé keeps asking to try anal but it is always excruciating for me. Are we doing something wrong? Any tips for how to make this more comfortable?
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Contributor: GingerAnn GingerAnn
Useful topic breakdown on Penetration:

Urethral Pain - Frustrated
I know I've posted about this before, but I have a lot of pain around my urethra during penetration and I am so, so, so frustrated! 2 days ago, I...

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I have been having some vaginal tightness while having sex with my girlfriend, which makes penetration pretty difficult despite the fact that it is...

Ladies, can you orgasm from penetration alone?
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anal toys for double penetration
I am interested in finding a toy for double penetration. I looked into a bunch before I was a little overwhelmed and undereducated. What would you..

If spooning, do you always find yourself on the same side or do you switch it up?
I just find it more comfy on my left side...vaginal or anal penetration. Once in a while, I am laying right side down, but NOT very often. Do you...
Contributor: ShadowedSeductress ShadowedSeductress
Generally a penis is too big to start with. It was very painful for me at first too. Then I started experimenting with plugs and small dildos to warm myself up. Lots of lube helps too. Just relax and go slow.
Contributor: Incendiaire Incendiaire
Practise by yourself with toys, until you can comfortably take something slightly bigger than his penis, then sex with him will be a breeze.
Contributor: MrWill MrWill
They've pretty much covered it. Play by yourself first... and if it isn't something you enjoy tell him. You don't HAVE to have anal sex.

If you do like it, try small toys and work your way up. The sphincter is very elastic and once used to relaxing anal can be VERY pleasurable.
Contributor: jennifur77 jennifur77
Make sure you're using enough lube. And if you think you've got enough lube, add some more. Then add a little more for good measure. Lube is your friend.
Contributor: Gunsmoke Gunsmoke
My wife was as reluctant as you are. After 23 years of no - she finally agreed to try. I wouldn't say she loves it - but she asks for anal play no and anal sex doesn't cause her any pain.

It takes time, and lots of lube - and a bit of determination on your part to find what works. Start with fingers, then small vibes, then a butt plug or two. By the time you can accommodate a 1.5" diameter butt plug, you are about ready to try anal sex.

I also suggest that do anal play with your husband - the pleasure/pain he experiences will help him understand what you are experiencing. What's good for the goose - is good for the gander. In fact it was a couple of years of anal play on me that convinced her to try it out for herself.

Read/watch what's available from Jaia or Tristan Taormino - they have good guides that you and your partner can use. They use to carry them on EF - but you may have to search for them on Amazon.
Contributor: AmethystQueen AmethystQueen
We start with one finger, then two fingers, then insert himself, always making sure there's enough lube.

One other thing you might want to try is practicing opening up yourself with butt plugs before you're going to do anal. Then it probably won't be so hurtful for him coming in because you're already open. You'll probably need to work up to one his size, but getting used to wearing plugs, especially right before anal sex, just might help make anal fun for you.
Contributor: Herzer Herzer
I agree with most of the previously comments but I'd actually recommend starting with a tongue. Some light then harder rimming action always helps my wife relax and open up.

If he's asking for it he might also want it done to him and be too reluctant to ask. Try rimming & gently fingering him the next time you go down on him and see how he reacts.
Contributor: sexyshae sexyshae
Originally posted by cbmb716
My fiancé keeps asking to try anal but it is always excruciating for me. Are we doing something wrong? Any tips for how to make this more comfortable?
All great reply's. Make sure you're cleaned out that can make it very uncomfortable. Start with small toys and front stimulation to relax. After you become comfortable get your fiance to enter half hard, much easier for you. Make sure you control the situation for your comfort at first.If he listens to you that will make you more comfortable and confident for the next romp. If he is longer, anal will be much more comfortable than vag. There is no wall for him to hit and he'll find numerous great inside spots. Have fun take it slow and start by yourself first, then move to the next step. Hope this helps.
Contributor: Bubba29 Bubba29
read this article and follow it closely. it should help A LOT.

Contributor: Gasmiclady Gasmiclady
After 5 years I finally gave in and gave anal a chance. We have tried probably 8 times with about 3 of them being enjoyable for me. I don't love it though. I highly- highly- recommend starting with finger play- maybe while he's playing with your clit. Then as you open up and get comfortable you can lube up and try. You absolutely have to be relaxed so if you're not in it mentally it's going to hurt.
Contributor: cmm cmm
Just get some plugs to dilate with.