Chasing Me Chasing You

An uncollared submissive struggling through depression, motherhood, and the constant craving of her next orgasm.

Popping the Cherry

So I lost my anal virginity last night. Is that a thing? I’m sure it’s not. And those of you that have been doing this for a good decade or so will just laugh at this milestone. But for me, this is a big deal. I’ve been training for a few weeks now. Sir has been pushing me quite hard. We were going to start earlier in December, so I could be ready by 2015, but life happened.

I was just excited that it didn’t hurt as much as I thought. It actually felt pretty good. I don’t know what that says about me. That I was silly enough to think that it would hurt, or smart enough to be happy that it didn’t.
So that was my Friday night. Several orgasms and my first anal intercourse. Hope you all had a nice night too. I’m looking forward to the rest of my weekend. We’re staying in as it is still negative temperatures outside and in the forecast. After a few job applications I am hoping to curl up with a book and some coffee. Baby cuddles and quickies sound like my perfect Saturday afternoon.

3 Responses to “Popping the Cherry”

  • ara

    I felt the same, wondering afterwards why I had made such a big deal of it in my head.

  • Florida Dom

    If it hurt at all, he probably wasn’t using enough lube. Tell him you really need lots of lube and then you will love the way it slides in and makes you feel kinky and submissive.


  • His slut

    Some days it hurts, some days it doesn’t. I lost ‘that’ virginity with Master. I’ll never forget it. Welcome to the ass club!


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