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I can’t do anal because it hurts.

I’m all for being open minded and doing things to please my partner but I just cannot tolerate anal. It hurts… BADLY. There was one occasion where I stuck it out and he managed to get about halfway in and thrust maybe a handful of times before I was crying and he stopped, that’s the farthest we’ve ever gone (and I bled for two days afterward). Even small toys hurt back there, I can’t do it.

I’ve told him I feel bad that I can’t please him that way. I’ve told him how much it hurts. He’s felt my body trembling from pain, he’s seen me cry from it, he knows I’ve had so many bad reactions that the subject of anal gives me anxiety. But he still tries, a month or two go by and he’s trying to penetrate me back there with a finger, his dick or a toy. I ask him to stop and he tells me to let him try, he tells me it’ll be different, he’s even given me guilt trips by asking things like “can’t you try one more time for me?”

How do I make it clear that I’m done trying? I can’t take it. Maybe that makes me a terrible girlfriend or sex partner but I can’t do it, it hurts too much.

Venice’s response to anal hurts
If you bled for two days after trying anal with a toy, that sounds pretty bad. But believe it or not, it’s not that uncommon (but also not good), and judging from experience, it may have been caused by a several things. Little / Not enough lubrication – sometimes when the sphincter is lubricated, but not inside beyond it or around it, anything that is inserted (penis or toy) can get pulled in and cause tears.  “Tensing up” – if you and your body/mind (including ass muscles) are not receptive to anal, you will clench and make penetration painful. Communication – as long as you’ve tried, and you said you did, that is a positive step. But making you feel bad will make you hate anal even more.  Talk about it beforehand; if he tells you that he wants to try anal moments before sex, then you’ve both failed. The only way you can make anal sex pleasing to you is if you are willing and ready to do it. And of course, there has to be some prep on his part. He should lick your ass, tongue-fuck it, and suck your rim.  All those things will show you that your ass is an area for pleasure, not pain. Anal sex hurts at first. When I have anal sex, my orgasms are better – they’re more sustained because my clit doesn’t get sensitive. I can have multiple orgasms, and they’re brought upon faster because the pressure and more intense feeling of this hidden erogenous zone. 

Ryan’s response to anal hurts
Short answer:  If he doesn’t understand that anal hurts, clone his dick with a clone-a-willy and fuck him with his own penis until he bleeds.  See how he likes that.  I hated it and learned to go slow and easy the hard way!  Literally.  If he is pressuring you to try something during actual sex, he may not be the type of man you want to invest more of your time with.  A good boyfriend will respect your wishes.  The worst time to communicate about sex is during actual sex.  Sit him down and talk to him about your feelings when neither of you are horny or caught up in the moment.  Specifically him.  Most importantly, if you are bleeding during anal sex, he isn’t doing it right to begin with.  You should never be bleeding during anal sex, ever.  He shouldn’t be asking you to do anything that he has no idea how to do to begin with.  

Compromise answer:  Maybe an answer most people disagree with, but relationships are about communication and compromise.  Set a date, maybe his birthday, that you will be open to try new things with him, as long as he lubricates properly, goes slow, and stops when you ask him to stop. Trying something once a year wouldn’t be a bad idea for all couples.  Maybe something you didn’t enjoy last year, will be much better this year, especially because it is planned out properly. Our bodies change.  Our tolerance changes.  And even our tastes change.  Maybe having a date that you can mentally prepare for will help you.  Spontaneous anal, especially when it hurts your feelings he asks you after you have expressed to him you don’t want it, will never be a pleasant experience.  Ever.  I have no doubt in my mind that the one thing that makes anal pleasant, above all, is having a positive attitude about what is happening, what you are giving him, and embracing the sensations. That goes for any sexual activity.  I am pretty sure all of us naturally do not like the sensation of something going up our anus.  But because of our attitude, our willingness to experience various sensations our partner can give us, we turn that weird sensation into something positive.   And if we know it won’t happen for another whole year, it’s easy to be enthusiastic and enjoy yourself.  Worrying that if you like it or try to enjoy yourself, he may want anal much more and you will have to bite the sheets every night, seems to be a big fear with women.  So they shut down.

Long answer:  Would you prefer he just never asked again?  I don’t agree with the idea of “Never ask me again because my answer will never change.”  That isn’t how communication works.  I am guilty of the same thing your boyfriend does, but not exactly.   I wouldn’t put pressure on Venice during sex.  However, I would talk or text Venice during the day and ask her if we could try anal that night.  When we first met, she was open to anal and told me I could have any hole I wanted on her body, whenever I wanted.  It’s so easy to be open to everything, when you are so in love and everything is perfect.  As the endorphins and high from our new love wore off, she made it very clear she did not enjoy anal anymore.  It hurt.  I can still remember the car ride where she laid it out in plain English for me, “I will never enjoy anal, no matter what.  It’s the one thing in this world I will never like doing. If you want to do it, do it, but just know it will never feel good to me.”   I believe this is when we made a compromise that it would be something we try on my birthday only.  However, on my birthday I would feel so guilty because I knew she hated it, I would ask her to play with her massage wand on her clit while I slowly work my penis inside her.  Sometimes I would just stick my head in only while she played with herself, worried putting myself all the way in her would be totally unpleasant for her.  In the end, because it was my birthday she would be open and positive, she would openly tell me she had the most intense orgasms she had ever felt. Saying that had risks.  Like maybe I would suggest we do it more than once a year.  She made sure to let me know, “The orgasms were good, but I still hate anal.”

This issue became more of a tug-of-war, rather than something she really hated.  She hated that I wanted something she expressed to me that she didn’t want.  She hated that I would still ask her to have anal sex with me when she told me she wasn’t into it.  She hated the idea that if she told me it felt good, I would want it more from her.  And although I do not have the answer to a woman changing her perception on anal, I do know that with time and life experiences, we change.  Anal sex is now a part of our normal sex life and Venice has all of her best orgasms during anal.  Sometimes she will use my dick in her ass just to feel the sensations she needs to have more intense orgasms, but once she cums, I stop because I had already came earlier or don’t want to ruin her moment.  She went from hating it with a passion, to needing it to get off and have more enjoyable orgasms.  Like I said, people change.  Keep an open mind and don’t get offended because he asks you to try something that you feel you already made clear to him you aren’t interested in.  Your answer isn’t a life long response he should respect and never mention again.  That’s not how healthy relationships and good communication work.