You can try to slowly insert your fingers into his anus and move upwards to the top of the prostate gland in the anus and then slowly pull your hand out while putting steady pressure on the prostate gland while you give him a blowjob, and you should feel him get harder in your mouth to the point of him cumming and if you do it right he would have cummed in your mouth so much, it’s a form of prostate milking which the male cums when you do it right and it should feel like his balls has been drained of cum.
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@Sexy_Redhead Just a question. What is the goal? Is he all about cumming in your mouth? Is it you who wants him to cum in your mouth?
As @our-adventure-bed mentioned, this is fantastic but it may get old soon. Looks like you are onto something and having great success so great work. Just be careful it doesn’t become mundane with only him getting pleasure. I’m not sure it’s fair.
Unless of course the next task is him making you squirt from vaginal torture! Then tell him to get practicing!
Sounds like you are having a great time. Keep it up!