Start With A Lubed Finger If you browse the rectal intercourse Preparation Guide here, youвЂ™ll understand that it is best to try penetrating your self ALONE first having a little finger covered in lube to make sure you arrive at observe how your sphincter responds to it. Then you can get your man to do the honors this time if youвЂ™ve already done this a few times and have a good idea of how long it takes to relax around your finger. Then i recommend that you try it alone first while following these instructions if you havenвЂ™t done it by yourself yet.
He has to use a little lube to your tip of their little finger and some more to your ass. Next he has to gradually slip their hand while you give him feedback, telling his to go deeper or to stop moving or to SLOWLY pull out (pulling out fast can cause some pain, he needs to do it slowly) inside you, millimeter by millimeter,. You deeper and deeper with his finger, it should feel reasonably comfortable as he slowly penetrates.