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I have found three positions that work for this: lying facing each other or lying with you behind her – both these mean that only part of your penis will penetrate her; or with the girl on top lying flat. Sitting up will hurt, definitely. However, by lying flat she can completely control how much goes in and get clitoral stimulation as well. These positions work better than lubrication alone because the problem is your penis bruising her cervix, not lack of lubrication.
