Reddit reviews The Ultimate Guide to Anal Sex for Women, 2nd Edition

I would start here so you don't do any more damage... And this possibly the best lube ever and on all counts better than menthol lotion

A few ideas:

1. Start by getting a copy of Tristan Taormino's The Ultimate Guide to Anal Sex for Women, 2nd Edition. It will tell you how to do it safely, without him hurting you. Also, it can really help to hear about anal from other women who love it.
   
   
2. If part of your worry is sanitation or the mess, get some FC-2 condoms. They are perfect for buttsex. Unlike regular condoms, they protect you from abrasion while giving him lots of friction and sensation. And they eliminate the possibility of smelly stuff or cross-contamination.
   
   
3. Get a graduated set of buttplugs and/or anal dildos (the kind with a flared base so they can't go in too far). Practice inserting an FC2 in your butt. Once it's in, slip your finger inside and feel around a little bit. Practice gently pushing out and relaxing. Then insert the smallest buttplug and take some time getting used to it. Work your way up to a dildo that's almost as wide as your BF's cock. When you can do that comfortably, you're set to try him out.
   
   
4. Ask for something in return that makes sex better for you, so this isn't just about his needs. We've had a couple of recent posts about the joys of full-body erotic massage, which can be a fantastic experience. If, after some careful experimentation, you find that you CAN have anal without pain, then it would be entirely reasonable to say that you're willing to end a luxurious, highly orgasmic yoni massage with anal sex. The advantage of doing it that way is that you are far more likely to enjoy having anal after you have already reached peak arousal and had multiple orgasms by some other means.
   
   
5. Speaking of orgasms, I suggest always having your favorite strong vibrator handy and using it as much as you need to reach orgasm during anal. We usually put a bolster under my hips, with me face down and my clit resting on the vibrator. Trust me on this: it makes it much easier to enjoy anal if you're both getting off every time.
   
   Anal isn't for everyone, and you should be confident about saying a hard no if you try it and you really dislike it. But I think it's reasonable for him to ask you to give it a fair try, and it would be a shame to miss out on some great sex because some ignorant teenage boys hurt you.
   
   Enjoy!

I you're just starting out wearing a butt plug for longer times is too much.
Start out gently. Stimulate her pussy and or clit with fingers, vibrator, tongue, while you slowly and with a lot of lube play around her asshole and then insert a finger or small toy. When you stick something in her, go slow. Don't move around the first minute, but wait for her muscles to relax.
The amount of lube you need is: if you think it's too much, take a little more and that's the right amount.
Read Tristan Taormino's book or see the film.

tl;dr go slow, lots of lube

[Guy input]:

Get this:
http://www.amazon.com/Ultimate-Guide-Anal-Sex-Women/dp/1573442216/

But to your questions:

• Go slower. Just fingers for a while. Maybe a butt plug.
  
  
• Enema, about an hour before. http://www.optimalhealthnetwork.com/1.5-Quart-Economy-Enema-Kits-p/0HEconomyEnemaKits.htm
  
  Some people find it fun/kinky to administer enemas to their partner.
  
  
• Typically, on your side, with your upper leg drawn up to your chest.

Can I make a book suggestion? Taormino addresses many of the fears and taboos women often have about anal sex from a woman’s perspective, head on, and supportively. Before reading it, my SO wouldn’t ever consider anal, and though we don’t have it all the time now, we certainly have it a satisfying amount. Let the book be a guide for your discussions.

https://www.amazon.com/Ultimate-Guide-Anal-Sex-Women/dp/1573442216

This is an older post and discussion with a lot of good tips about getting started with anal:

• I need advice on anal sex
  
  I second the recommendations for Tristan Taormino's Ultimate Guide to Anal Sex for Women, 2nd Edition and for the FC2 "female" condoms, which completely eliminate the need for prep and the worries about making a mess.

Here are three books all by the same author. This is the best I can do, the last one is written for women but has some good information, and yes a week isn't nearly long enough to learn this, and you might not ever do it.

http://www.amazon.com/Ultimate-Guide-Kink-BDSM-Erotic/dp/157344779X/ref=la_B000APS9US_1_2?s=books&ie=UTF8&qid=1377358061&sr=1-2

http://www.amazon.com/Anal-Sex-Position-Guide-Mind-Blowing/dp/1592333567/ref=la_B000APS9US_1_6?s=books&ie=UTF8&qid=1377358061&sr=1-6

http://www.amazon.com/Ultimate-Guide-Anal-Sex-Women/dp/1573442216/ref=la_B000APS9US_1_3?s=books&ie=UTF8&qid=1377358061&sr=1-3

Anal sex done well never needs numbing. I really don't recommend using Anal-ese or any other numbing gel. It does numb but that also means you cannot tell if something goes wrong. Unlike the vagina, that area is not 'designed' for penetration, the walls are thin and relatively easily damaged.

If you want to continue exploring this, check out Tristan Taormino (www.puckerup.com) and especially http://www.amazon.com/Ultimate-Guide-Anal-Women-Edition/dp/1573442216r. Accurate information from a sex-positive educator.

https://www.amazon.co.uk/Ultimate-Guide-Anal-Women-Guides-x/dp/1573442216

Relevant

>just didn't sit well

Unintentional comedy :)

Buttplugs aren't really meant to be moved. They give you the experience of being filled, but not of being penetrated per se. You might want to try a thinner dildo while masturbating. Only caveat here is to make sure it's long enough. Otherwise you'll have to re-penetrate the inner sphincter repeatedly, and that can be very unpleasant.

It's also possible, sadly, that anal isn't a thing you'll find pleasurable. Not everybody does. But before jumping to that conclusion, I'd read "The Ultimate Guide To Anal Sex For Women" as it's a great resource.

Good luck!

I'm not entirely sure (not being a woman) but if you want to know about women and anal sex, you should check out Tristan Taormino's 'Ultimate Guide To Anal Sex For Women, it's supposed to be excellent.

Hmn. You guys need to work on your communication skills, it sounds like.

For one thing, talk with verbs and nouns, not adjectives or descriptors. Be specific about what you think and feel, and describe things literally ( know this can be a bit intimidating, but go with me here). Use "I statements" instead of "you statements" (talk about how you feel rather than judging the other person or projecting your perceptions on them).

For example (during a non-sexually charged time with SO):
It is far more helpful to say "I've faced harsh judgement in the past for [specific actions here], and since then I've felt insecure and uncertain about doing anything different or new during sex with you. When this and this and this happened, I have felt discouraged and "weird," and I've had a hard time initiating anything since. I would like your help thinking of things I could do and that we could do together that would bring variety and excitement to our sex life."

It is not helpful to say things like "That's weird." This is a vague and, yes, judgmental statement. It's more helpful to say "I think anal sex can be dirty and gross, and don't like the idea of getting poop on my penis (dick, whatever). What exactly do you find exciting about this?" Or simply "Thanks, but that doesn't really feel any better."

See Nonviolent Communication.

I would highly suggest researching anal sex, and maybe even the book The Ultimate Guide to Anal Sex for Women, because from personal experience, anal sex can be fantastically amazing, and practiced in a safe, fun way.

I hope this all helps, good luck!

Ass play feels good for everybody. If you think it's gross, then have him use nitrile gloves/condoms and you've just cut your transmission risk factors.

There's an entire book on anal sex for women:
http://www.amazon.com/Ultimate-Guide-Anal-Women-Edition/dp/1573442216
(There's also one for men.)

She even did videos and things on pegging: http://www.goodvibes.com/display_product.jhtml?id=8-7-ML-1201

You need to get this book.

If you are in that much pain, he likely has no fucking idea what he is doing, saw it in porn and thought it looked interesting.

Anal is kind of the Varsity level of sex. It takes a long time, skill and a lot of patience. Guys who watch porn and see it, have no idea that those women are fluffed and aroused for hours before they film the shot.

You can't just jam it in there, you have to get relaxed, aroused, thoroughly lubed, then slowly work on opening up the anus with fingers and toys before you ever get around to PIA.

By the time you are ready to put in a penis, there should be pain and definitely not any bleeding.

And if you don't like it, it's not something you should be doing just to make someone else happy. That is not a good sign for your mental health.

Read The Ultimate Guide to Anal Sex for Women by Tristan Taormino.

You might want to pick up Tristan Taromino's book https://www.amazon.com/Ultimate-Guide-Anal-Sex-Women/dp/1573442216

I think she has instructional DVD's too.

And I'm glad he was into the idea, sounds like you might have found his sex drive again right there!

This book is great!

You need to respond by buying her this book.


The Ultimate Guide to Anal Sex for Women