Masturbation does make you a better lover because, as you're well aware, knowledge is power, and getting to know your body is the first step to achieving wonderful orgasms, whatever hot spot you choose to apply pressure to.
If you want your girlfriend to really start liking anal sex, tell her to start practicing the technique on her own at first, so that she knows how pleasurable it can be.
Nowadays most experts agree that if a woman can reach orgasm through her own efforts, she can then learn to climax with a partner during love play or intercourse. Learning to climax through masturbation gives a woman confidence and satisfaction- and also educates her on how she likes to be touched and stimulated. Once she knows these things, she can communicate them to a loving partner.
Masturbation is that more important in this case, since anal sex is really a technique that needs to be mastered correctly in order to be fully and completely enjoyed by both parties.
Before you two get on to the anal routine I'm describing in this book, in order for your girlfriend or wife to be truly prepared for the act, I strongly suggest that she engages in some sort of anal self-pleasuring session so that she learns how her body works, what to expect, what turns her on and what not, where to stimulate more and where less, etc., thus making sure that she has a clear picture in her head of what the whole act is meant to be.
Getting to know her anal area on her own at first will make it easier for her to enjoy this erogenous zone with you. If she incorporates anal masturbation into her private self-indulging routine, she'll enjoy the awesome sensations of anal sex with much more intensity.
During her next solo session, tell her to explore her own body in minute detail, particularly the anal region. The best way to begin exploring the possibilities is in the shower. Using a hypoallergenic cleaning bar, she should soap up her fingers and massage the area surrounding her anus. She could also use a long-lasting water proof lubricant.
She should take her time in this kind of exploration, allowing herself to get turned on while relaxing her anal sphincter muscle for nicer, easier penetration.
If you want to help, make sure she's in a relaxed space, free of interruptions, so that she can note her likes and dislikes.
Here's a step-by-step guide of anal masturbation that you can pass on to your girlfriend, so that she knows exactly what to do in order to transform this into a pleasurable breaking point for anal
Start by applying lubricant to the anal opening and your finger (Note: if it's your first time, your anal might be tighter and you'll need to start with your pinkie). Caress and massage the area with your finger until you feel a pleasurable tingling and your mind and body go in sync, urging you for more. Slowly start inserting your finger.
As your doing that, you might notice that your initial sphincter muscle will begin to spasm, resisting penetration. Breathe through any desire of squeezing the anal opening shut, and try and remain relaxed. Instead, take control and squeeze your anal sphincter muscle. This will allow you to feel the difference between a relaxed and a clenched rectum, plus it will help you prepare for your full finger insertion.
As your anal opening relaxes, push your finger in a little deeper, just up to the first knuckle. Take a break here as your anus gets used to the sensation. If you are experiencing any pain, remain still; if the pain doesn't subside, remove the finger slowly and either add more lube and use a smaller finger or take a rest from this activity and play with your other hot spots for a while.
When you're ready to start again, breathe deeply and as you exhale and the sphincter muscle relaxes, slowly and carefully slip your finger deeper inside, pressing against the front (stomach side) rectal wall.
After one or two minutes, if you feel excited enough, begin to thrust in and out of your anus… deeper, faster, slower, it all depends on how you want and how you like it.
You can also use a toy specifically designed for anal sex play (see chapter 13 for more about anal toys). These are smooth, free of sharp edges, and no more than 5 inches long. Most are tapered- thinner at the top than the bottom- so the anus gradually dilates when you insert the toy. They also have a flared base to prevent complete insertion of the toy. (Explanation: Unlike your vagina, your rectum is not closed at the top, and objects can be sucked inside. Every emergency room physician has stories about the strange objects he or she has removed from someone's anus. You don't want to be coffee-break conversation, do you?)
In order for you to gradually become more accustomed with the toy, try stimulating your clitoris and vagina at the same time. Some women love the full feeling of having both their erogenous zones put to work. Also, the muscles that are stretched by the toy are the same ones that contract during orgasms, so you'll be experiencing far more intense climaxes.