Listen up, fans of interesting sex challenges. This week’s guest blogger has a kickass idea for you. He’s written some fabulous guest blogs here before, including a delightful piece about where he wears his wedding ring, what a prostate orgasm feels like, and his quest for the perfect butt plug. So I’m delighted to welcome him back today to mark the start of a fun sex challenge he’s set himself for the month of November. And no, it is definitely not the one you’re thinking of…

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This gorgeous femdom dating fantasy is written and read beautifully by The Barefoot Sub, and originally appeared on her website. Note that it contains pain, spunk-milking and pegging.

Dating, what a nuisance it is. Or maybe it’s the looking for a date that I find so awful? Having to network, usually online, initially before meeting for a coffee at a neutral location. So much posturing, posing, preening. Being vulnerable and allowing others to see the real ‘you’ appears to be actively discouraged. So very far removed from who I am, not to mention being the opposite of what I want in a partner. That all changed when I met you.

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This fabulous piece, in which you get the prostate play you requested, is written and read by Molly Moore and originally appeared on her website. 

You are such a good boy for me. I like it when you do as you told, like today, for example. The message I sent you on my way home read: “Be naked on the bed. Use the under-bed restraints and attach the ankle cuffs. I will be back at exactly 1pm. Be ready.”

And you were.

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The first time I make you come is just for me. I’m not even going to bother taking off all my clothes. I’ll just yank my knickers to one side, hop on your erection the second it’s hard enough, and ride your dick till you fill me up with spunk.

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I don’t know if I’m allowed to just invent a piece of sex etiquette, like I’m the editor of NSFW Debrett’s, but if I were allowed to do that, I’d suggest an etiquette rule like this: if you’re fucking someone with a butt toy in, and you have the ability to hold it there while you pound them, you absolutely should. So for instance, if we’re fucking doggy-style, one hand laid on my butt with a steadying thumb against the base of the plug (not pushing in, just holding still) will calm my anxious mind and mean I can focus on the shag rather than the worry that I’m about to inadvertently shoot it across the room. This rule brought to you by a woman who – no matter how safe the butt plug or how secure it feels in my ass, the second you start to plough away I will immediately panic that my lubed-up arse might accidentally blast it at your stomach like a rocket launcher. My top concern with anal toys is not whether they’re going to get in, but whether they might just slip out. That was my key concern with the Hot Octopuss Plex, and why I tested it in ways that may seem silly to you, but which for me formed vital anxiety-calming prep before I (hopefully) get to use this during sex.

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