In some circles (pun completely intended), I go by the title "Unholiest of The Unholy Hole Stoppers". Those circles just happen belong to my girlfriends. And yes, I did give myself the title. And yes, I do make them call me that. #privilageofrank
Let me start by saying, "I love the buttsex." It ranks in the top 5 of my favourite pastimes. If given the choice between "sneakin' in the back door” and saving a kitten from a burning house, I'll always choose 'Option A'. No hesitation. The cat is probably the reason the house is on fire anyway. Screw that cat. However, you can't just whip it out and shove it in. As with everything in life, there is a right way and a wrong way. If you do this wrong, you could seriously injure someone.
If the person you are canoodling with has never had anal penetration, some work up to actual anal sex is probably in order in order. Butt plugs can be used to help your partner become accustom to having something inserted into what has traditionally been an exit only. Start small and don't push it with the amount of time it's inserted. Gradually you can work to larger plugs for long duration's. Eventually, they will get to where they can handle your massive manliness with grace and style.
Fingers also make a great starter tool and warm up device. If you're a bit squeamish about using your fingers, most drug stores sell latex finger cots. Think of them as condoms for your fingers. By the way, I highly advise utilising both finger cots and regular condoms if this is a partner you aren't already fluid bonded with. Safety first. The butt-sex does not prevent the spread of disease.
Lube. Lube. Lube. Lube. Lube. I only get so many words here, and I was sorely tempted to just repeat "lube" 500 times and turn in my assignment. You can't have too much lube. Find a quality lubricant (not the warming kind, I know what you sadistic bastards were thinking) and apply generously.
Start slowly and give them time to adjust to your enormity. I've heard from multiple partners that it sometimes helps to have them push against you as opposed to you entering them. Just keep in mind that you are placing them in a very vulnerable position, and potential a very painful one. If you ever want them to allow your horse back in that particular stable, you'd better be conscientious and safe.
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