Message: Advice for Anal Virgin Wanting to Try

Anonymous: I’ve had sex with a lady friend of mine who is kinda naughty. Though only oral and vaginal. She is a scared anal virgin but willing to try. Next issue, she is on the fence about us filming ourselves. How can I make the anal and video happen

Those are entirely separate issues, and the latter is not within the subject this site focuses on. For trying anal, there are many guides out there on how to have anal for the first time. You and she should read through as many of them as you can find. The basics:

  1. Always use lots of lube. Lubricate both the anus and the object about to penetrate it.
  2. Use smaller objects before trying to penetrate her anus with your penis. Try a finger to start with, and slowly work up in size with multiple fingers as she is able.
  3. Go slowly. If anything hurts, she should immediately tell you and you should stop. If you stop in place for a moment, the pain or discomfort will usually fade as she gets accustomed to being filled with something that size. When she’s comfortable again, you can continue. Early on you may need to start and stop a lot, especially as you’re increasing the size.
  4. Don’t try penetrating her with your penis until she can comfortably fit an object (or several fingers) the diameter of your penis.
  5. When you do have actual anal sex for the first time, she should be on top so she can control the speed and angle of penetration.

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