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Nerves can be the biggest factor the first time. It can cause her to tense up, which can make penetration very painfull. The nerves killed of my erection when I first tried it. The solution is easy, be relaxed at easy. It's never wise to immediately begin with a penetration (it doesn't matter how much LUBE you use). Fingering (try using more fingers to stretch her a little bit) and oral stimulation were for me the best ingredients to get my girl in the right and very horny mood). She told me she only felt a second of discomfort before feeling very very nice.
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