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As you go. Always pay attention to your partner to indicate whether or not he or she feels comfortable. Slowly attempt to push your finger (or plug) slightly inside the anus. Do not use force - stop immediately if your partner complains of discomfort. If it is difficult to enter the anus, you probably need more lubrication. The first time you try this, the receiver may feel a bit of pain. Anal sex is not for everyone, and if you feel uncomfortable stop and perhaps try again later. Think of this process as training for later ...
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