June 13, 2008, Newsletter Issue #120: First-time Anal Sex: Men

Tip of the Week

Men tend to have more reservations about anal sex, due to the (unfounded) concerns that enjoying it may question their masculinity. Even those men who agree with digital (finger) penetration my draw the line at other objects like butt plugs and dildos being introduced.

Regardless, here are a few tips for first-time anal play.
Try it the first time during fellatio.You partner should be sure you are well aroused.Using a decent amount of lubricant, coat the anus as well as one finger (usually the middle one). Be sure fingernail is clipped short and has no jagged edges. An alternative is to slip a condom over the finger.While continuing fellatio, your lover should trace around the outside of the anus, stimulating the nerve endings there. (Most men find this to be arousing enough, but it gets better.)Slowly ease the finger into the anus, stopping briefly after each knuckle, until the entire finger has penetrated him.Begin to draw small circles with your finger inside his rectum. Some men may not enjoy in-out movements, but you can always try both to see what works.Prostate Gland Stimulation: Curl your finger toward the front of his body (as if gesturing, “Come here.”). As you continue with oral stimulation of the penis, press and stroke this area. Sometimes just constant pressure does the trick.Always be on alert for your lover’s guidance and communication. Remember: This is not a conquest; it’s supposed to be pleasurable.

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