Does it feel better to do it with out a condom?
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Condoms
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yes... but use a condom anyways.
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my girlfriend is not a virgin but i am and shes on the pill and cuz its my first time should i wear a condom
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Yes, you should, every time. Even if she is on the pill and takes it regularly, you should to be safe, and for protection against STDs.
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first of all it protects from STDs. Second, it helps put comfort in knowing there's an extremely small chance she's gonna get pregnant.
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Yes, but pregnency and STDs are an omnipresent threat. It's also harder to enter without a condom (you need more lubrication-natural or otherwise). Finally, sex is pretty damn good with a condom, so enjoy it safely.