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Stimulate your G-spot. Once you've tapped into regular orgasms, the key is prolonged stimulation of the urethral sponge. How To Make Yourself Squirt During Sex · 1. Get your bed ready just in case. · 2. Try to relax, and give yourself plenty of time to get turned on. · 3. This is where ejaculatory fluid comes out when you squirt. It's not That means that for lots of folks, it's possible to squirt over and over again more or less indefinitely. Me and my boyfriend have to use lube to counter this. As a man it seems I wouldn't know shit I know but just relax as much as possible. 1. Go it alone. The first step in learning how to ejaculate involves masturbating. My research has shown that strengthening your pleasure.