Start by stretching the glans a few times. Feel free to spread the opening wide. Massage and squeeze the glans and shaft. Be gentle but firm. Massage out a lot of pre-ejaculate. When the cock is ready to be penetrated, don't forget the lubricant. Insert the dilator carefully and play with the cock and its opening. Vibration can be extra hot. Here we finish with a sensitive handjob where the sperm leaves his glans with very nice pumping strokes.