My girlfriend and I have tried to have anal intercourse before, but she always finds it too painful. We have never quite managed it as a result. Help!

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First, and foremost, not everyone enjoys anal penetration. You may
follow all of my advice, and still never get your girlfriend to enjoy
putting stuff in her bum. I'm in no way a porn hater, but it is
important to know, that the joy of shoving huge things in tiny
assholes is not as common as porn would lead you to believe. But, if
she is turned on by the idea of anal sex, and willing to try, you're
off to a good start! I also always say, if you want to give it, you
should be willing to take it. The male g-spot (aka p-spot) is most
easily accessed anally, so you may want to get in on this fun too!

To begin, lets learn a little bit about bum-holes.

#1. The anus does not lubricate itself, and spitting, or re-
distributing pussy juice doesn't count. I recommend silicone lubricant
like Pjur Eros (http://condomshack.com/shop/pjur-original-100ml-
p-156.html) for anal play because it's super slick, and doesn't dry up
and get sticky like water based lube can. Not using lube can lead to
friction and tearing of the delicate anal tissue, which will make your
girlfriend less likely to ever let you back there again.

Never use numbing lubricants like Analeaze, your bum feels pain for a
reason, it's telling you to slow down and/or lube up. Using a numbing
lubricant may make anal sex possible once, but her days of pain
afterwards will ensure you never get it again.

#2. The first thing in her vagina wasn't a dick, so the first thing in
her bum shouldn't be a dick either. Pussies are extremely stretchy,
but most people start with fingers before they try to fit a dick in
there. Bum holes are much less flexible, so let's start small there
too. You can use your finger(s), or small, soft toys to ease her in to
the sensation of anal penetration. Most bum toys start small, and
gradually get wider. The Sassi Bendi Dome (http://condomshack.com/shop/
sassy-bendi-dome-p-250.html) starts as small as a fingertip, but is
almost 5" around at it's widest, making it an great anal trainer.
Insert it slowly and gently (with lots of lube), as far as your
partner is comfortable with, and with time she'll be able to take it
deeper, and deeper.

#3. Most women have to be really turned on for anal play. Don't get so
focused on her bum that you neglect everything else. Stimulating her
clit and vagina effectively, may increase her want for anal play. Make
sure you listen to your partner, and pay attention to what works, and
what doesn't. Whether or not you ever make it down the back alley, it
will make sex much better for both of you. When you've gotten her so
horny with foreplay that she's going to explode, her body will be much
more receptive to your penetration. In contrast, if you fumble around
her clit for a minute, then try to shove your dick in, her body will
be much less accepting.

When (if) she's ready for anal sex, don't go for doggy style. It seems
logical but, positions where she's totally relaxed are better.
Spooning is great, because she can relax all of her muscles (and
sphincters) and control how deeply you penetrate.

Never go from back to front! Even if both of you are STI/STD free,
there is bacteria in bums that should never end up in vaginas. DO NOT
put fingers, dicks or toys back in a pussy after they've been in a
bum! An easy way to be safe and clean is to use gloves and/or condoms
for anal play, that way the bacteria can be easily thrown out, leaving
you a clean hand or dick underneath. It's way less of a hassle than
washing thoroughly with anti-bacterial soap in the middle of your fun.
You should also never use sanitizing gels like Purell. They are almost
pure alcohol which is drying and irritating to genitals.

Also, keep in mind, some people will enjoy anal play, but not anal
sex. She could learn to love rimming, fingering, and toys, but never
be able to handle full penetration and thrusting. Or, she could end up
loving it, you never know....