External Prostate Massage
A big issue for most men is anal stimulatino. Most men think that if you massage the anus or male g spot then you are totally gay. This is a totally false belief system that stops to most guys not expernceing intense male g spot orgasms.
Prostate stimulate can be done externally by massaging the perineum, or for more pleasure by internally through anal penetration. I like a soft touch on my external prostate area as well as internal anal touch.
Try external prostate massage before you take the next step of anal insertion. Experiment with a light touch or a heavy touch and see what works for you.