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The first little-known fact is that during pregnancy less oxytocin is released in response to nipple stimulation than when a woman is not pregnant.5
But the key to understanding breastfeeding during pregnancy is the uterus itself. Contrary to popular belief, the uterus is not at the beck and call of oxytocin during the 38 weeks of the “preterm” period. Even a high dose of synthetic oxytocin (Pitocin) is unlikely to trigger labor until a woman is at term.6
Instead, the uterus must actively prepare in order for labor to commence. You could say that there are two separate states of being for the uterus: the quiescent baby-holder and the active baby-birther. These states make all the difference to how the uterus responds to oxytocin, and so, one can surmise, to breastfeeding. While the baby is growing, the uterus is geared to have a muffled response to oxytocin; at term, the body’s preparations for labor transform the uterus in ways that make it respond intensely to oxytocin.
Rule of thumb is that if you experience contractions while expressing/breastfeeding or any nipple stimulation.. even sex I would imagine! (lots of oxytocin then too :) ) is to stop what you're doing and see if the contractions also stop. It's generally thought that nipple stimulation won't get labour going unless your body is already ready to labour, so I wouldn't worry too much.