Before putting any object into a person’s anus use common sense. And for those of you who are at a loss of what common anal sense is keeping reading.

• Listen to your partner.  This includes both verbal and non-verbal cues. What does she/he verbally say? Has she/he told you she/he wants to experiment with anal stimulation? Does she/he like having her/his butt touched. Does she/he get more excited as your finger brushes along the tip of her/his anus?
• Never try something on a partner that you would be unwilling to have tried on you (unless specifically requested).  
• Always use retrievable objects. Can you imagine having to rush to the emergency room and explain to the on-call doctor that you have part of a cucumber stuck up your butt?
• Be clean. Wash all your tools with antibacterial soap and hot water before inserting them into your partner. You can also disinfect your toys by soaking it in hydrogen peroxide (full strength) for 15 minutes.  
• Always use smooth objects.  Anything sharp or jagged runs the risk of puncturing the anal canal. This not only causes pain, but also may lead to infection and other complications.
• Avoid rigid objects. Flexible objects will enable you to maneuver through those curves in the rectum (and there are many of them!)
• And most importantly, be realistic. If this is the first time experimenting with anal stimulation start small. Your fingertip is more than sufficient and will definitely create a rise. Fisting, and other such forms of anal-play are something that takes time to learn how to do / receive.  Trust & experience are something that only comes with time and practice. There is no such thing as an overnight expert.  No one is good the first time they have sex. Everybody is slightly uncoordinated and miss the social cues that teach us about a partner’s body.  Give yourself time. You have the rest of your life to perfect these techniques. Let yourself savor the moments of each ‘new’ thing that you try
• To begin experimenting with anal pleasuring
• Both partners must be willing.
• Experiment with a finger, or an anal plug
• This will help the insert begin to get comfortable with this new sensation. At the beginning of anal pleasuring, take a deep breath and relax. The more relaxed the anal muscles are, the easier it is to insert a finger, penis or anal plug. Lubrication will help the entry process and will reduce the risk of tearing the inside lining of the anus. Saliva and water based lubricants work well. According to Jack Morin, author of Anal Pleasure and Health oil is a recommended method. Having spoken with several sex educators, I have heard mixed opinions about this recommendation. Thus to be SAFE, I recommend using water based lubricants and/or saliva.
• If something hurts, STOP.
• s*** Happens.  It is an Ass after all.  Have some wipes handy around and reassure you lover it is no big deal.