Dear Mistress Maeve,
I'm writing on behalf of me and my partner, as we need some assistance in the "back door" area, if you will.
I am a 34-year-old female without much anal sex experience. He is a 37-year-old male whose ex-girlfriend could apparently fit the Goodyear Blimp into her anus without so much as a drop of lube. I, on the other hand, am having a very hard time getting his penis into my ass and keeping it there. It just plain hurts! I've tried to "just relax," but that doesn't work. We get it pretty much all the way in, but it's more painful than pleasurable, so I ask him to take it out. Mistress, I want to have anal sex! What can we do to make it work?
From Pain to Pleasure?
I like a girl with good anal will and determination! Just remember, you're not a failure as a partner if anal isn't your thing, so be sure you're engaging only in sex acts that make you both feel good.
That said, if you're bent on taking it like a champ, I can offer these points of anal insight:
Lube: When engaging in any kind of anal penetration, always use lube to avoid injury. If you think you're using enough lube, add more for good measure — you can never have enough.
Preparing the way: The anus can be a very shy creature, puckering up if spooked. Don't go from having nothing in your ass to having the full girth of your guy's member. Foreplay with his fingers or a small toy will train your inner sphincter to relax.
Position: Positioning is key to relaxing enough to receive anal. Forget doggie-style or you being on top (way too tense); try lying in a spooning position with him entering you from the side. Or let him enter you from the good ol' missionary position where you can lie back and relax.
Gaining entry: When the time comes for insertion, take it slow. Don't allow him to enter you, pull all the way out and then enter you again (ouch!). Instead, allow him to enter you about an inch, then ask him to apply gentle pressure while you slide back onto him. Once he's in, remind him to be gentle — no slamming the back door (at least not until you're feeling more pleasure than pain).
Lubed and ready,