Stamina training until multiple orgasms and male squirt 05:45
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How to make him cum twice
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It shouldn't, as the erection closes off the bladder fluid exit and opens the sperm exit. That said, repeated milking, particularly with the cock in a downward position, can blur the lines. Stimulation post orgasm can cause the relevant muscles to relax and allow bladder fluid to pass. There's also the whole sub-subject of prostate swelling, (Internal and external), which can affect the natural control system. A lot also depends on if the bladder was emptied prior to the play session, non empty = increased pressure and urgency.
