trey, how do know when its ok to piitb? and should you ask first?
lol. I don't know what's worse. The fact that I have never seen the acronym "piitb" yet I knew instantly what it meant. Or that I don't even have to think about this as all. Because I have already given it years of thought. I must put a disclaimer out on this answer though. Seeing as how all girls are radically different from one to the other. But I still think that in general, we can come to a consensus on this one.
Ok. You
can ask first. You have to feel your girl out to really know the answer to that one. It's a gamble. Maybe she is actually willing to do it with you, and you just made that a lot easier. Or maybe she finds it repulsing and never wants to talk to you again. A more likely scenario is that even though she is turned on by anal sex in porns and secretly thinks about trying it, she will say no way and don't even try it. Which puts you in a situation because obviously you are still going to try. But you lost your innocence in the situation because she already said no, so she can legitimately be mad at you. It's a roll of your dice on the asking. I have asked 1 night stands and it actually worked one time.....but only one time. None of them ever walked out on me though. I have gotten a finger up there on multiple one night stands though. Which brings us to the root of the question.
How do you know when
she is ready. Because obviously you were born ready. Assuming that we are talking about long term relationships here and not one night stands ( because obviously me being me I know that you are in a long term monogamous relationship ) A lot of guy would say that putting it in her butt pretty much seals the deal that you own her. So it would be logical to use reverse logic and if you have hit the point in the relationship where she totally depends on you and appreciate you for the provider you are, you could probably go for it. But think life can be much simpler than that. Especially since I am attracted to independent minded females.
The key is to not rush it. You gota spend some time down there eating her out anyways right? RIGHT? Because if not, you are already fucking up. So while you are down there, slip your tong down a little bit lower and just see if she likes it. She cant get mad at you for that. I'm sure she thinks it feels good. But may say no because she is uncomfortable and insecure about the idea. So its also probably a good idea to try right after she has hygiened. Just let her know that it really turns you on. That she shouldn't feel insecure. Do whatever you have to to accomplish this. Stick your tong all the way in there and look happy about it, Smell her farts, eat her shit, whatever it is that you have to do to let her know she can relax, do it. Once you get that down, you move on to fingers. A lot of times you can do this on your very first attempt too. Get down there and really get her wet. Go to town on eating her out, and finger her at the same time. Get your fingers super lubed. Then when you know that she is really getting into it and maybe about to cum, slip a super good lubed index finger right in there. Swiftness is the key. You can't be slow about it. Chances are she will be so relaxed and so focused on her vagina that she wont even know what hit her. Except an amazing orgasm with the help of her anus. This is huge because now she knows that it doesn't have to be all painful, and might even be pleasurable. If you can keep her on board from here, its still a long road. But the uphill part is flattening out.
Start practicing getting her to relax the sphincter. Get her comfortable with the size of one finger. Then move to two. Then three. After 3, she is probably ready for the cock. Just keep reminding her that this is something that is really a big deal to you. Chances are she loves you and wants to please you so she will stay on board. Don't be forceful, she has to be able to relax. Be sure to have tons of lube on had at all times. Seriously, never be without a lube pack in your pocket. You never know when she might just want it. It takes time and dedication. And she will probably want something in return. So fucking buy the whole box set of all the seasons of sex in the city. It will be worth it. Good luck and god speed
P.S. if all else fails. Find a gay guy. They like this sort of thing. Just be sure he advertises himself as a "bottom" and not a "top" or else you might suddenly be sympathizing with your GF in a way you never though possible.
