So Tight

I've done double penetration before. The problem is, the men you're with will often have little regard to how you're being dominated - the "hormones"(?) they have often mean they are rough on my vagina and rectum. DP is good, but be careful :/

So long as it dosen't happen at that 'time', everything should be alright.

Stinkhole, come on! she can have an enema before penetration to clean it up!

As for tightness of the anus, it's just exaggeration.

I wonder about that.

She's a anal virgin, as far as I can recall. It might bleed, like the vagina.

:unsure:

My Ex was into BDSM. Let me just say, those were not the greatest of times. Have you ever been one woman in a room with five naked, horny men? I went along with his BDSM for a bit (It was tame then), then one day he brought some assortment of toys, ropes, a whip, and four other people into it. :/

I can understand that, although me and the missus get kinky from time to time.

She likes to dress up in an Imperial Japanese Naval Uniform and call me a 'dog', and an 'idiot'. I used to hate it at first, especially when she later started punching me like the bullies back in my high school during sex with the outfit on. But I have to admit... it's kind of hot. The pain's become kind of a 'combustible' turn-on.

Fendom generally isn't bad, as the men seem to like a dominating woman. That's why I'm lesbian now - woman are far more considerate sexually - they actually understand troubles you might feel at times.

We do try futa every now and then ;)

Despite being a lesbian, you still go for the futa?

Well, that's something we don't see every day... [size=7](but it's kind of understandable?)[/h]

Like I said, women are far more considerate - to tell you the truth, a foursome with other woman is one of the greatest experiences of my life. We sometimes use hands (and feet) to help each other, but strap-ons (and double heads) are fun with other women. BDSM with other women is often a mixture of pleasure and fun, instead of that with men which is fear, pain and perhaps pleasure.

I've got a picture of me and some friends doing the Triforce. It's a pretty fun position ;)

what ethnicity is the girl?

Had this problem before, hitting the womb can hurt her if your not careful :P

Use some toys to help with the width, the more relaxed the sex is the better, get some lubricant to help with it sliding, Sounds stupid but depending on your stamina and how long you like the sex to go on for just use the tip of your dick, if she's sensative around the sides that'll be even better for her as well.

The more you have sex the easier it'll get :)

Read this doujin : https://www.fakku.net/viewmanga.php?id=2780

Same problem as yours

A girl can bleed from vagina during first time having sex, because her hymen gets torn = blood.
But a girl doesnt have a hymen in the ass (doh), so no, she wont bleed if you dont fail.
So, use lots of lube LOTS. First finger her (and do some rimming if both of you are willing) till she can relax a bit. Then put the tip of one of your fingers in (to the first knuckle), play with her a bit and when she's relaxed again, go deeper with your finger, and again play. Do that till your finger is in and then you can try the same with 2 fingers or a very small toy.
All the time make sure you're using plenty of lube and make sure you do everything she tells you. And just move into bigger toys (or use more and more fingers if you dont have toys) till she thinks she can take your superhypermega cock in her. And again, do it SLOWLY, even if you want to cum fast. If she tells you to stop, you stop. If she tells you to pull out, you pull out.

Also, in my experience the best position for anal if you want to prevent getting hurt is spoon. She can be in totally relaxed position. Like in doggy style shecant totally relax, or if she's on her back, she still has to keep her lower body up a bit. So yeah, at least for me spoon is the most pain free position for anal :)

-Just so you know, you have to work it up. Use even more lube than vaginal sex and start with gentle fingering. Then a sharpie, then a small dildo, then a bigger one, then your cock. She has to really relax to enjoy it, otherwise she will bleed.

-That aside, how tall is she? The average sized western woman is actually supposed to be able to take a pretty big penis. When a female is fully aroused the uterus lifts-up and the vagina distends past the cervix. sure she may be smaller than average, but if you're only getting 1/4 of 9" in then there's something wrong. As said before, get some edible, water-based lube (oil melts latex, but if you go bareback then use baby oil, the vitamin E is good for your skin).

-Really get into foreplay. Try 69'ing and make sure she has an orgasm first, if that doesn't get her ready...Like I said, when she's truly ready she should have little problem taking at least 3/4 your penis.

My advice would be to try cowgirl.. when she's on top she'll know if it hurts or not, she'll know what to do (eventually). you'll just have to concentrate, haha.. and obviously dont forget the foreplay first.