First, if you're easily offended, I don't suggest that you read this (unless you want to feel offended, you masochist!). Now, for those of you still with me, this is the most useful article you will ever read.
Every time I approach my girlfriend with my desire to defile her asshole, to rip her up, to make her an anal whore, to sodomize her till she cries I get the same answer: "tomorrow." Then tomorrow I get a reprise of the "no" refrain and wonder if I'm in some kind of endless no-anal loop. It's depressing--I'm stuck in an endless promise of tomorrow. Also, I know that in many ways she means well: she wants to please me, doesn't want to disappoint me, yet isn't sure she can tolerate taking my big cock up her ass. How can I change her mind? How can I make her want it?
SETTING IT UP
There is a lot of skill involved in getting her to let your big cock up her tight ass. It's no small matter. It hurts, it leaves her constipated, sore, and walking a bit strange, it scares her, and it's one session without the sure pleasure of clitoral stimulation. So you need to do a few things, most of them unrelated with sex. First, you need to addict her to all that princess stuff you are capable of. Get her dependent on your compliments, little baby words, and whatnot. Then pull it away. Subconsciously, make her aware that you could start up a relationship with someone else, and make her realize that she needs all that sugar that drips effortlessly out of your mouth. Subtly, make the connection that if she gives up her ass, she'll get more sugar than she's ever seen. Note, this must be done subtly, subconsciously, or she'll feel cheap and feel like you're trying to use or disrespect her. If she catches on to what you're up to, you're in a shitpile of trouble. So do it right.
"You're my little princess baby," you say and stroke her hair romantically.
She says, "I love it when you talk to me like that."
You, imagining your cock up her ass, blurt, "Why don't you spread that asshole open so I can fuck it?"
She pulls away and looks at you like you're a dirty pervert. Which, of course, you are.
as opposed to
"You want to be my little princess, baby?'
"I want to be as close to you as possible." Massage her asscheeks. Then, kiss her neck and ears gently. Show her she can trust you to be soft and gentle. This will overcome the fear that's holding her back. Now you are ready to see if this is your chance: stick one finger in gently and say: "You can be my little princess." This makes the connection between princess and ass-fucking (the essential link). If she doesn't deny you, you're in. Simply say: "I'll be gentle, don't worry."
(see the difference?)
This is the key: set up a relationship where she feels like she may lose you if she doesn't keep you happy and then make it seem safe and not scary. Once she's going to give it to you don't get all out of control. Be slow, rub her asshole, lick it, lube it up. Take your time with everything and when you start, don't force it in. Let her come back into it. Getting the head in is the hardest part for her. At this point, follow all convetional anal sex wisdom. My service to you is the persuasion/coercion of your girlfriend/wife.
Now, once you're all the way up her ass, she is all yours. There's no turning back for her, so fuck her ass as hard as you like and tell her that she's your anal pig.