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First, a problem of nomenclature. Be sure you know which term your man prefers, which will likely provoke many giggles on both ends. It's like using the word "penis" or "vagina" in bed. You might not know it, but even Wikipedia agrees that the taint is a highly erogenous area. It's got plenty of nerves running through it for both men and women which is why women often get a raw deal when they tear in childbirth.
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How To Touch A Man Between His Testicles And Anus To Make Him Orgasm Fast

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How to Have Anal Sex for the First Time: A Beginners Guide | GQ

Dick Butt was created by cartoonist K. Green in for his webcomic Horribleville. Then I go and draw the stupidest thing. I thought, What is the stupidest thing? And then I had my answer.
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Oh No! This Guy Broke His Dick During Butt Sex

Every man's biggest fear is seriously fucking up his junk while he's fucking someone else. OK, well, every man's greatest fear is an orifice that bites, but after that it is doing something that is going to make your cock and balls fall off your body like an over-ripe fruit. During a recent sexual encounter he totally screwed up his nether regions something horrible and was basically laid up for a week with searing nut pain. Here is his story. It will give you nightmares.
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This is an article describing in extremely explicit terms aspects and frustrations of anal sex, including those that involve feces. Specifically, those elements of anal sex that I have rarely to never heard anyone talk about outside of the confines of extreme privacy, due to their uncomfortable nature. I have noticed in male-female relationships that there are two things Boyfriend Zero has fucked up for everyone: oral sex and anal sex.
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