• It may be easiest to use your middle finger due to its longer length. Wash your finger well with antibacterial soap beforehand so that you don't introduce anything that could cause an anal infection. Use lots of lube on your finger.
• Alternatively, pop a latex barrier on and apply lots of water-based lube to your finger and anal opening.
• Breathe in and tense your sphincter muscles, as if to stop defecation. Once you can feel them it’s easier to control them.
• Breathe out and bear down to open your sphincters. Gently move your finger into the anal opening. If you feel your sphincter muscles tense around your finger, hold still and wait a while until they relax. Breathe in and out deeply to relax.
• When the contraction eases, breathe out, bear down to open the muscles again, and move your finger in a bit further.
• Once you pass the anus and enter the rectum, explore different types of stimulation of the rectal walls, like moving your finger gently in and out, or in a circular motion, or stroking the walls.
• A curved vibrator or dildo or a crooked middle finger is ideal for stimulating the prostate or G-spot a few inches in, through the front rectal wall (the belly button side).
• As with any type of sexual exploration, if it hurts, stop. 

• It is important that the recipient is highly aroused before you go anywhere near his or her anus. This is because the anus is much more receptive to touch when the person is already highly aroused.
• Both recipient and penetrator need to be gentle and patient.
• Be sure you trust your partner implicitly and can communicate openly with him or her before agreeing to anal play.
• Before you start playing as a couple, discuss what expectations both of you have to make sure you are clear with each other.
• Penile penetration should come last. Start with gentle stimulation using a finger or slim dildo or vibrator. The light touch of a finger is probably ideal for your partner’s introduction to stimulation of the anus.
• If you are providing finger stimulation, ensure your fingernails are short and smooth. Pop a surgical glove, finger cot or condom over your finger(s). This will provide protection from infections and prevent the anus being torn by rough skin or sharp fingernails.
  
• Use lots of lubrication. The anus and rectum do not produce any lubrication the way a vagina does, so you will need to use something – saliva, vaginal fluid or a good quality anal lubricant (preferably water based as oil-based lube may remain in the rectum for some time and destroy latex condoms on contact). Avoid lubes with nonoxynol-9, which can irritate and damage rectal tissue. Apply adequate lube to the anus and to the penetrating object.
• Anal penetration is almost always uncomfortable at first but once the sphincter muscles have relaxed, the discomfort subsides. Massage the anal opening gently with a finger using lots of lube.
• It is crucial that the receiver takes control of how and when penetration occurs, and controls how quickly you graduate onto larger objects or deeper penetration. This means the receiver should ease onto the penetrating object, rather than the other way around. See the useful tips in the preceding paragraph on how to start with solo anal play.
• Anal penetration can be uncomfortable if the receiver clenches their sphincter muscle so it is important to relax. A useful trick is to push out your anal muscles as if starting a bowel movement – this causes the sphincters to relax and open.
• The anus needs a more gradual approach than the vagina, and it may not be able to take the full length of the object, nor vigorous thrusting.
• Communicate with your partner as you proceed, checking frequently to find out how they are doing. Ask, “Is this okay so far? Does it hurt at all? How does it feel?”, etc. If you feel any pain, tell your partner immediately. You should feel able to stop altogether at any stage.
• If inserting an object such as a butt plug, use one with a flared base so it doesn't get lost up the rectum. This is because the sphincter muscles can ‘pull’ any inserted object deeper into the rectum.
• Use toys that are flexible enough to follow the curve of your rectum if inserting them further than four inches.
• While stimulating the anus, maintain genital stimulation simultaneously as together, this will transform the entire genital/anal area into a highly aroused zone.

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Sources of information:
“The last lovemaking taboo lifted?” – Brian Alexander at www.msnbc.msn.com/id/17285757
302 Advanced techniques for driving a man wild in bed – Olivia St. Claire
superhotsex – Tracey Cox
The Big Bang: nerve’s guide to the new sexual universe – the writers at nerve
The Good Vibrations Guide to Sex – Cathy Winks and Anne Semans

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