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You need to loosen up your gf, not her asshole. I'm guessing she's pretty nervous about how it's going to feel to have a cock pumping in and out of her ass. And so that nervousness causes her to completely tense up.
I'm not exactly the most" assfriendly" person I know. Do this a couple of times and soon the outer sphincter muscles will start to loosen up. Introduce the trainer. Have her insert it (so she