Get yourself worked up using fingers or a vibrator, as you're nearing climaxing start rubbing the well lubed dildo again your pussy. As you experience the climax exert pressure on the dildo enjoying the sensations of it starting to penetrate your pussy. Keep steady pressure until it becomes uncomfortable then let up but keep rubbing and start attempting to insert it again, going slow, don't ever force it, just let your pussy slowly adjust to it until you secede, it may take several sessions but in time you'll accomplish your goal.Note: use plenty of lub, warm up the lub and dildo first before using as it'll feel much better and facilitate entry. Have fun and keep us updated.