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Having had two c-sections and being told I could never expect to have a vaginal birth, I internalised the idea that I would never use my body in this way and that conditioning is hard to overcome. Also...well I don't know how else to put it, but a rather uncooperative vagina over the years, I was sure I would tear top to bottom. I tend to tear and bleed a little during normal vaginal sex, but I had an 11 pound 12 oz baby and no tears.
Pretty cool eh? Also Jenny Blyth's book Birthwork has some lovely stuff about looking after your vagina. When you do the perineal massage, you are not trying to 'force' your body to 'stretch more', it's more about confidence and awareness. So, let it be gentle and soothing, and notice when you are holding tension in your abdomen and chest. Then, use your breath to soften by gently exhaling ... letting the tension drop away as you exhale .... and you soften down there, too ... then you an gentley resume the massage. It's a great skill that works well for birth, too.