Providing that's a standard beer bottle you're holding, I can see at a glance that your cock and it's head are a nice size but not so big that it should make your gf sore. So what's going on? For a start, I'd advocate against using ice in her pussy because as it quickly melts and becomes water it washes away her natural lubrication. Instead, I wholeheartedly agree with previous posters - use plenty of foreplay, and don't be embarrassed to use some extra lube.
But I want to ask a question or two: What kind of soreness are you talking about here? Is she experiencing painful jolts - like you're bumping something tender - which could be an infection, or is her soreness something that feels more like abrasion? Either way it could be that she has a cervical erosion or something so it might be an idea for her to show it to her doctor. Another possibility is that she isn't really relaxed about having sex. Intellectually, she might be right there with you on this, but subconsiously, she might be inhibited for some reason (ie. her upbringing, a previous bad sexual experience, something else) and she isn't really managing to relax properly. It can lead to an involuntary tightening of the vagina, causing painful sex. This is surprisingly common, and needs to be taken seriously. It can be successfully treated with appropriate therapy.
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