It was her idea...she liked to have it and used it to accomplish it....Not like I was forcing her...I prefer the other hole...coconut oil works excellent as well.
Like I said, numbing the pain is a bad idea in my opinion. You have to listen and understand that pain to ensure proper safety.
I'm with cbcrazy on that one NEVER use numbing lube. That usually leads to more injuries than it is worth. C/S, Rev J
make sure she's relaxed, some lube maybe (i still need to attempt). me and my girl have done so before, we've stopped recently because it hurt the last time if i remember correctly so she's been staying away from it (though i hope we try again soon, have lube now! hah) just slow and steady.
My length is not much issue (6.5) but I have a mushroom head and this makes deepthroating nearly impossible for my girlfriend. When it comes to anal, RooRshack is completely right. It really helps to take a crap, pardon my french. It doesn't have to be a big one but there needs to be a cleansing so to speak. After my girlfriend does her business, she cleans up and that in itself aids to loosening it up. I then use two finger for massage and insert a below average size dildo, which is to say I don't think many real penises are that narrow. That stays in her for about 2-10 minutes depending how much work I want to do on her vaginally. When I take it out it's a great indicator if everything is spotless. In which case I lube up my dick (dildo was obviously lubed so her asshole should already be slick) with baby oil. I then gently by quickly insert the head to get it in there and then work slow with the shaft until things become easier. Of course we don't have anal too often, maybe 5 times a month, but we usually have anal twice in the same day about once a month because once we've gone through all that work and her asshole is now relaxed, it's going to be an easier ride the second time, preferably within 2-3 hours. This is where it might be fun if we plan ahead as I'll plug her butt after cumming inside so the second time I'll just be adding in.
Its a mindset for sure. Relaxing is key! Do whatever relaxes you most. Even if its a glass of wine or some smoke ;-)...Lube is obvious and spend some time getting use to being played with. Toys, fingers or whatever. Good luck ;-)