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I have to agree with Acetylene here. Eros is key. Sphincter control is next and to avoid learning bad habits you need to go slow. If you have to apply more force to get it to go in then you are doing it wrong. Focus on aim and angle and then apply a small amount of steady pressure. What you want to avoid is overpowering the sphincter quickly. The tip of the penis does not taper along with the shaft so it feels uncomfortable on the sphincter if you pull out too far while thrusting. Once you are in it is mostly a function of how much and what quality lube you have.
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"It better be funny" 
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