So we’ve had a talk about what we could try out, what we want etc.
So he’s open to the idea of having anal sex and doing anal play. He isn’t exactly thrilled (at least not yet) but that’s mainly because it’s new to him and he’s a bit nervous. I myself have some experience from it. I’m always clean so that isn’t an issue.

My strategy is this:
He doesn’t have to do anything new actively himself – he’ll just feel the plug inside me while fucking.
Before he comes over, I’ll put a plug in me. At some point before dinner I might reveal it to him, or I might wait till he initiates sex and then I’ll let him know about it.
This way he doesn’t need to get stressed about having to do something, he can just enjoy the new sensation inside me.

He likes surprises, so I figured out that this could be fun and maybe get him turned on even more.
How does this idea sound, is it okay or too much? Is there something more I should take into account?

8 comments
  1. Lay him on his back, grab his cock, and lower yourself onto it while you slide it in your ass. Then lean back and ride him. Tell him to let you know when he’s about to cum, then ATM to finish him off.

    He’ll be ring shopping by the end of the month.

  2. Get on top during PIV. Lift up and put him in your ass. An ex did our first anal that way and it was great.

  3. > This way he doesn’t need to get stressed about having to do something, he can just enjoy the new sensation inside me.

    This sounds like a good way to take some of the pressure off of him. I’d recommend letting him know before he initiates sex, maybe as part of some blatant flirting/teasing throughout the night. If you can get him to associate anal with your arousal/pleasure, he’s more likely to be interested rather than anxious.

  4. Not too much at all. It’s a great start.

    At some point you might also try inviting him to use his finger/thumb during doggy. One gets a deep appreciation for the feeling of the area with the hands.

  5. He’ll feel it alright. It will feel very tight. He’ll likely get off early. But it’s something you don’t need his consent for because it’s your body. If he likes it see if he’d be open to moving it in and out with his thrusts.

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