Alright, so I have had anal sex before with my ex.

and me and my boyfriend want to have anal sex but his penis is like twice the size of my exes.

It hurt with my ex but we didn't use lube lol clueless.

This time I am prepared with lube ... *dances*

Will it still hurt?

or any tips for making it less painfull?

why on earth would you put it in the title for
i meant to use the big penis thing discreetly
you based the WHOLE thread about it

*RAGES*

But yes, this does turn me on greatly

I wouldn't do it, but you know...It's because I enjoy my working sphincter. If you don't mind having your butt destroyed, I see no reason for you not to move foward with this idea.

Just remnember, the anal sphincter is one of those parts you take for granted...Until it's GONE.

I hope you two are both regulars when you split up, it's gonna be hilarious.

Only newbs like anal sex. Go ahead and try it...see what happens. I'm willing to bet you guys won't be very fond of it after a few tries(at least the girl). I know girls that like their assholes poked etc, but very few that actually have experience with it and like it. Oh god the thoughts that crowd my mind with anal are some of the most horrible thoughts ever. Shit just falling out because your muscles/hemorrhoids get stretched so far it just comes out like diahrheah, hemorroids falling out of your ass to name a few that I've personally seen. Oh god...I don't understand why any respectable girl would rather have a cock shoved up their shithole vs. their vagina anyway....and the guy should feel the same. Unless for some reason the girl's asshole is actually nicer than her vagina...*shivers*.

Edit: Also, there's nothing you can do to subside the pain. You've gotta wait til dat asshole is stretched out far enough to be able to take an ass pounding regularly.

First off, are you guys retarded? Honestly, the information that has been given is a load of crap, and biased.

Here's the real scoop on anal sex, and anal play.
First, it is very enjoyable once you get past the mental idea of having something in your bum. The anus actually has more nerve ending closer to the surface than the vagina. The anus also gives the best angle for hitting the female and male G-spot.
Second, it doesn't destroy your ass. Just like your vagina, the anus is made of a stretchy skin that can more than manage a penis. The anal sphincter is a muscle, and it's actually good for it to be stretched, as it improves elasticity of the muscle, thus improving it's function as a terd cutter. You won't get hemorrhoids from it either. Actually the friction will cause your ass to toughen up, reducing hemorrhoids. I'm a guy, but I've used toys probably bigger than most guys cocks in my ass to stimulate the prostate. So far there isn't any damage at all, and I actually crap better. As a bonus, it's very unlikely I'll ever develop prostate issues later. My ex loved getting drilled in the ass too. She said it was so much more intense, and she came so hard with it too. As a bonus, anal sex also agitates the digestive system making things move much more smoothly, especially if you have constipation problems. Another bonus is that you'll never get pregnant.

Here's a technique to improve the experience.
You have to work up sizes by stretching your sphincter until you reach the desired level of elasticity. Just like I wouldn't expect you to be able to do the splits right away, but if you stretch every day, eventually you'll be able to do the full splits. Anal sex is the same. Your best bet is to use progressive butt plugs. The start out small, and then get larger until you've reached your desires size. Eventually you'll be ready to take that big dick.
Then, just try and relax those muscles and use adequate lube. Some women are fine with spit, others use a glycerol based lube. The trick is to ease it in slowly at first until you reach the required depth or it won't travel further. And then just increase speed to whatever you're comfortable with.

This guy knows what he's talking about. I can vouch for it.
Just like to add that if you don't like the idea of getting dirty, wash the bum with an enema before sex and wear a condom, which is also lubed further.
I recommend baby oil as lube so as not to degrade the condom.

I am sensing a lot of gay in this thread.....

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you are 100% right!

To answear your original question. Yes it will still hurt, but if you use enough lube it will be fine. When taking it in pretend like your pushing out to loosen the mucle. The more tense you are , the more it will hurt. Good luck.