We had tried pegging but it did not seem to do much for either of us. I did not/could not ejaculate from penetration alone. Likewise it did nothing for my wife. I think we both saw it as more of a power transfer/humiliation deal.Â
She felt it was more work than it was. Worth for her and since there seemed to be nothing going on for me not it was worth it. Â
Then she bought a double headed dildo a few weeks ago. Game changer. She is now able to get off while I am penetrated.
At first it still did not seem anal did anything for me. I think because she was now getting pleasure I no longer felt like I needed to cum. About the 3rd time while she was using it with me I had my first prostate orgasm? Hands free and lots of ejaculate. Wow. Hard to describe the feeling. Unbelievable amount of ejaculate.
Now it has become a common practice. Not every time but maybe once a week.  We do a kinda lesbian like scissors thing. I ejaculate most times. Still caged so always hands free. Seems to work like a ruined orgasm for me. Cum but no full blown orgasm? So common for me to cum more than once during.
Highly suggest trying it.