^^^^ yea never use anything in your pussy or ass that's not ment to go in there.. learned that the hard way.. vegetable oil.. yup not so good lol.. sounded like a good idea when I was drunk lmao...
I think personally that you went too fast. I think you should not go to straight penetration. Start out with your tongue. It is the least threatening object to put in her ass to get her accustom to anal stimulation. I have never heard of a tongue making a girl cry from anal. After the tongue then move to fingers and small anal toys, and finally your penis. I feel that you have kind of blown your chances at anal, since she cried and seemed to have a terrible experience. You will be lucky if she gives you an opportunity to try it again. If she even lets you attempt it again, it will be even harder now since she has the memory in her mind of anal being painful.
I've done that before and to be honest I like it. But she usually doesn't want me to because she's afraid of it being "dirty". Only immediately after showering will she ever let me do that.
That's the only time I do it too. After my girl cleans her ass, she takes a shower, then I eat and fuck both her holes until we both cum.
The same thing happened here. I tried anal sex a while ago. I always had this anal fantacy (probably watched too much porn) and she'd really loved me. So one night we decided to give it a try. Before you guys start to laugh at me, I admit I was a moron at that time. We did not prepare for it, after 5mins virgina sex, I simply moved to there. I entered her from the back, probably just entered 2 inches, She called it off. Well, she felt pretty bad about it, and she washed off my dick and gave me the best head I've ever had. After that I figured it out, it is a trade off, no anal sex, better other services. I have no complains.
Ive tried, and failed. I need to be more patient, but of the times "we've" tired, the mor foreplay and preparation, the much better the results. I learned also, position matters alot. Suprisingly, doggy is one of the worst ways to start off. Missionary and what not is much better as it doesnt automatically tense the muscle.s
I've often been puzzled by the way that porn movies make Anal Penetration look pretty much as straightforward as Vaginal Penetration. Being Bi I have been in the position where I've been able to experience Anal sex with both men & women, and for some reason, anally penetrating a female is far easier than penetrating a male. I don't know the reason for this - perhaps it's to do with the difference in the design of the hip bone, or the fact that the penile tissue isn't getting in the way, but I've always found that anally penetrating a male is not at all easy. Even after plenty of preparation with fingers, actually managing the penetration is a real problem, even with plenty of lube - in fact, the lube can even be a problem, as it can cause the penis to slip away from the rectum as soon as any pressure is applied in order to make the initial thrust. When I'm giving Anal, things aren't made easier by the fact that I have a generous girth, but the same thing applies when I am the recipient. As far as positions are concerned, I've always found the easiest (least difficult?) position to be Spoons. If you're not familiar with this position, it's where the recipient lies curled up on their side, either with both legs tucked up, or just the upper one, with the male lying beside them, approaching from behind.
Although I have never anally penetrated a man, or have ever had my ass penetrated, I can see how penetrating a woman would be easier. Think about this. If you have a big girthy penis, such as you say you have, when the hole stretches to open in a woman ass, the wall can stretch open further because it shares a wall with another empty space, the vagina. So the anal tube has room internally to expand because it shares a wall with the vagina which is an empty space, that would provide more room for the anus to expand. For a man, it shares a wall with the prostate and the rest of the male genitalia, that wall is solid and provides less room for the anus to expand, unlike the woman's ass that has a open space for the vagina on the other side of the anal wall. Just my .02,