Ok so I just started a new relationship within the past 6 weeks. This dude is a freak. I was previously in a 5 year relationship, and before that, a 6 year relationship. In those two relationships combined, I never did the things me and this guy accomplished this weekend. He tied me up so that I was immobilized and choked and I loved it. But he's really into anal, and I've done it plenty of times before, but it always has the same results: pain, bleeding, and me unable to go to the bathroom normally for days and passing mucus.  We didn't use lube, which was obviously dumb, but even with lube, I still find it painful. What am I doing wrong? How can I relax? And also, what can we try next? I'm in love! I've never had so much fun and felt so free.

for her to be on her back with her legs up over the guy's shoulders.

And yes, use plenty of lube.

I hope that helps.

Anal penetration shouldn't hurt, cause bleeding, or any of the things you mentioned.  If you really want to be able to have anal sex with him, you're going to have to do some work on your own and tell him to slow his role fucking you like that until you're physically able to deal with it.  

Anal toys, plugs, and the like can really help.  Buy several sizes of butt plugs, starting with a very small plug.  Get used to that one; wear it around, play with it. Use it while you masturbate, use it while you have regular sex.  once you get used to it, go up in size.  Train yourself to be able to to have anal sex in a comfortable way!

Also: always use lube.  Always.  Whether its silicone or water-based is up to you (i prefer silicone personally), but always always use lube.  The more the better.  Think there's too much? add more

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Hi have to agree with MissErinBlack...  
First off you have to prep your ass before you actually are with him.  Play with your ass with different size toys,, use lots of lube.  before you play, a good enema can help keep everything clean and prep as well. It feels good and helps the lubes glide better.  
Slow him down, have him rub your pussy with his fingers, your legs over his shoulders. You can get to the stool fucking later.  That is sitting on the stool bending almost flat, ass in the air. He will rock the stool and go deep.  
The key relax and stretch it out first, lots of looby....

I'm all for rough and animal play but not when it comes to anal sex.

Your partner needs to know that there are real concerns about anal fissures and tearing.  If you're doing a lot of bleeding, and you're not using lube?

I'm just shaking my head.  You're a sex worker?

Your body is your frigging TEMPLE!  Look.  Enjoy the guy.  I'm already not liking him because it's sounding like he's actually hurting you and either not caring or oblivious.

You're asking for opinions and you're getting one from an older woman who worries when reading stuff like this.

Take care of you.  Step back.  Decide how you're going to go forward the next time you're having sex with this guy and the possibility of anal comes up.

The others have offered some good advice.  I would suggest going REALLY slow.  Telling him to stop when he first puts the head of his cock in your bottom.  Let your sphincter muscle get used to his love muscle.

YOU control the penetration.  Not him, at least not until you're more used to it.

And the tearing and not being able to poop properly afterwards?  Don't do that to yourself.  Well, not again.  

Your bottom isn't like your pussy.  It doesn't stretch and then go back in the same way.  Not trying to be gross but wanting to help.

Be smart.  Then, have a blast with this guy, and write again and tell us EVERYTHING.

I just think that there are a lot of places to go, and explore, without physically doing yourself harsh, potentially permanent, harm.  (My old adage is a little hurting is good.  Harming someone is bad.  Syntax.  I know.)

Good luck.

Best,
Elisabeth

All rears are not the same and permanent damage can be done.

'mon.  I recently had a wonderful time with a girl.  Used lots of toys of ascending size and lots of lube.  When the time finally came I slipped right in and she was delirious

ive been with several women that were not anal fans prior as apparently guys seem to think just using lube makes it ok to shove it right in...

Getting someone to really enjoy it takes time, patience and lube...If I really want to fuck someone in the pooper, during foreplay I'll have her lay on her stomach and slowly and deliberately make love to her entire backside from her toes to her neck and ears...I'm very confident and it passes through cause I take my time! I'll kiss and lick every inch of her, usually I'll grab lube and really get my cock wet along with her entire ass so when I'm on top of her, I can really grind my hard cock between her cheeks while I'm kissing and licking her neck and ears and shoulders its a long slow process...by the time I'm at her ass, I'll eat that ass, lick it, kiss it, tongue it (obviously she needs to be fresh out of shower)..,.
Ideally a vibe of some sort for her Pusey while I'm eating her ass....I will use a finger or too slow.y into her butt while I'm eating it too ....you'll know when she's ready,,,,,her ass will be begging to get fucked..then I lube up again...at first I've found either mish with her feet on my chest or shoulders seems to be the easiest or spooning ....I slowly just put the head of my cock right on her brown eye and let it sit there...soon she will be bucking a little really wanting it bad...then slowly move inside inch after inch...once I bottom out, I'll just leave it like that for a little.....need to fuck it very slow and I usual,y just go in and out with a couple inches..short slow strokes...you'll know when to start speeding up...nothing better then cumming in an ass while she's orgasming

Charlie Glickman is my go-to guy for anal sex info. (Disclaimer: He's a friend. Anti-disclaimer: I don't receive anything for providing plugs for him, no pun intended.) Making anal sex awesome is kind of his niche in the sex ed world. He recently published "The Ultimate Guide to Prostate Pleasure", which is obviously intended for men, but he has many other resources for everyone. You can find him through Google (try 'Charlie Glickman anal').