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I had similar issues with a girl friend long ago. With the pain of the first few attempt, she was very gun-shy and that made it much worse. She’d involuntarily clench up and that was that.
May I suggest lots of foreplay. Get yourself off, first, without penetration. Then you and she can play with a, less-than-intimidating monster-cock; it's easier to remove the gun-shyness when it's flaccid. Excuse my crudeness but with it flaccid, you can try and stuff it in there and let it grow to fit... Use lots of KY…
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~micah
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