Oh, the naughtiest of naughty places! Anal sex is often the final frontier for the sexual adventurer. Remember kids, it's all about lube in the tube...too much is almost enough.
So, the most important thing about going where no man has gone before is communication with your partner. I've also been told by my knowledgeable hairdresser that enemas are key for a safe and clean ride. Of course, that is optional, but I would recommend it because there's nothing wrong with being clean while being dirty...
Another important necessity to anal sex is being aroused. After plenty of foreplay and ONLY after plenty of foreplay should anal sex be initiated.
After getting your partner wet and wild, turn her/him onto their knees. Make sure that you have plenty of lube nearby. I'm not talking KY here, but quality lube like Astroglide. Drip lots onto your finger and around the anus and insert your digit(s). This is necessary to loosen up the muscles for penetration. Also, you can consider purchasing a butt plug which gets the anal muscles ready for heavy loving too.
After your honey is comfortable with your fingers doing the walking (and please do ask), lube up your penis and inch your way in. Don't ram in like a Viking conquerer, boys. Some have said that a quicker entry reduces static/electric friction, but I have to disagree. If you want to avoid friction in your relationship, then don't down that road. Have her relax. By the way, did I mention that lots of lube is essential?
Go slowly and let her guide the speed. Don't try to speedrace your way through here. And though this will be a tight fit, think about astrophysics, men and hold onto your load. Add more lube as needed and don't stress out if events don't arrive at their full fruition. I am also a fan of the money shot on the back, but do as you will.
Another important point is that you do not want to insert anything that you have put in her anus into any other orifice--that's the most direct route to any infection which will assure you celibacy for a little while. And, if you're not a monk, that's no fun.
Till next week, meet all your needs and desires.
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