I’m 21F and my boyfriend is 25M. We’ve been together for a while and overall communicate well, but we’re stuck on one issue. He wants to try anal sex, and I don’t feel ready or comfortable with it.
For context, I’ve never had anal sex and I’m scared of the pain and the idea in general. We tried light anal play with fingers once, and I didn’t enjoy it. Since then, he brings it up about once a week asking if I’ve “thought more about it,” which makes me feel pressured even though he isn’t being aggressive.
What I’m specifically looking for advice on is how to communicate a firm boundary in a way that:
- makes it clear I’m not ready and may never be,
- doesn’t turn into an ongoing negotiation,
- and helps him understand that my discomfort isn’t something he can convince me out of.
If you’ve been in a similar situation, how did you phrase it, and what helped stop repeated pressure while keeping the relationship respectful?
49 comments
Ahh. No means no. He needs to wait until you feel comfortable though.
Maybe next time he brings it up sit him down and explain how even though it’s something that he wants it isn’t something that you want right now and how his constant asking if you’ve thought about it more is adding pressure to the situation and not helping. Tell him that if (and if may never come) you are ready to try then you will approach him with it not the other way around. You have to be clear and firm that his constant asking isn’t ok and is upsetting to you
Tell him to stop coercing you
I outright told my boyfriend he can touch the outside but absolutely nothing is going in. That’s that. He accepts my boundary because he’s not a r*pist. You should be able to tell your boyfriend no and he should accept it. If he doesn’t then he is not safe to be with.
Say no, and tell him to stop asking.
Bringing it up weekly is aggressive.
Ask him if you can do him first. If the answer is no from him, then your no should be acceptable as well.
Tell him no.
Pretty much thats it.
You don’t seem to understand how disrespectful he’s being, if you’re worried about hurting his feelings. You really don’t get how wrong and gross this is.
Shut him the fuck down: “I don’t want to do anal. No. Stop asking me and stop bringing it up. This is not a debate. You’re being disrespectful. Never bring this up again.”
Offer to get a strap on so he can try it first.
Why are you worried about “hurting” him or somehow damaging his trust? Those concerns make no sense at all. He’s no longer going to trust you because you don’t want to do this specific sex act? Just be clear and say you don’t want anything up your butt and you’re not changing your mind, so he can either accept that or leave.
If you want to really hammer the point home, you can tell him he’s more than welcome to buy a dildo and fuck his own ass.
Maybe you would feel more comfortable if you tried it on him first… yeah… then when he says no, bring it up alllll the time. Best of luck. He’s a dink.
Edit to add: maybe buy the strap on and have it with you so he will really think about how that might feel…. Not judging though, I like anal.
He needs to stop talking about it. By doing so, he is passive aggressively pressuring you, and unless he’s stupid, he’s aware and is purposely trying to wear you down.
Tell him anal is *never* happening, he needs to accept it, and you will walk away without an answer any time he mentions it.
He is damaging *your* trust right now. That should matter more to you.
setting a boundary about something you don’t like sexually is never something that will “damage trust” if you’re in a healthy relationship.
if you have *never before told him* that you don’t want to have anal sex, then tell him. once. “I do not want to have anal sex now or in the future. my boundary is firm, don’t ask me again.”
if you receive any additional pressure after having told him the first time, dump him already and find someone who isn’t a total loser.
The problem might not be the way you’re communicating it. The problem might be that he’s not taking “no” for an answer.
Say “I want a relationship where I feel safe and not pressured into sexual acts I don’t want to engage in. Do not ask me about anal sex anymore. Do not bring it up to me ever again. Not as a joke, not as a what-if, not as a thought exercise. If you bring it up again, my trust in you will be damaged. If you value this relationship, you will respect this.”
If your partner respected you and cared for you, you would not need to give this speech. I wrote this out because I don’t think you are ready to accept what his behavior says about him and his feelings about you. Telling your partner you aren’t interested in anal isn’t “hurting him” or “damaging trust” (wtf?) in any way and only a manipulative person would suggest otherwise.
No is a complete sentence. If he keeps pressuring you then tell him to kick rocks because a person who loves you wouldnt pressure you into anything. Just say “No. I dont have any interest in anal sex. If that is a problem fo ryou the door is right over there”
You told him no.
He’s not accepting your no and trying to weasel his way into your butthole despite you saying no.
This is 100% dealbreaker behavior.
Honestly, I would break up, OP. Your boyfriend doesn’t respect your ‘no’ and is trying to wear you down. This guy is a loser you’re better off without.
Hey so I stayed with someone like this for a long time. He wouldn’t take “no” for an answer but otherwise had this whole thing about what a feminist he is and how important consent is to him. Yet when it came to practice, he often completely ignored my “no”. I didn’t realize how messed up it was until I got out of the relationship and started dating someone who never pressured me and just accepted “no” as a complete and final answer. You deserve to be treated with respect.
**NO** is a complete sentence
If he can’t respect that without getting angry, he doesn’t respect you
He’s emotionally manipulative and won’t stop asking because your butthole is more interesting to him than your personality
Fuck his feelings. Stop worrying about his feelings when he’s only concerned about using you like a fleshlight. I’m begging you to realize that you’ve already told him you do not want this and his refusal to stop asking IS SEXUAL COERCION. He knows he’ll eventually be able to wear you down. Someone like him is not even going to make it nice for you. He’s concerned only about HIS pleasure.
Don’t have this conversation again. Just leave him.
It’s really gross that he keeps pressuring you. Have you mentioned that to him at all? I mean really, who wants to date a sex pest.
“I’m not interested in doing anal.”
If he pushes back on that or tries to negotiate, then the response changes to: “I’m not interested in sex with you.”
So you’ve already told him you’re not comfortable with it, and he brings it up in conversation WEEKLY? Jesus. I’d be afraid he would “accidentally slip it in” with the way he’s obsessing. He is trying to wear you down, and he doesn’t care about your comfort or enjoyment.
First of all, I want you to know that a boundary is something you put in place for yourself, not for other people.
Second of all, “I’m not comfortable trying anal, I don’t know if I ever will be, please stop bringing it up because it makes me feel like you’re not listening to me and you’re only using me for sex” should really be all you need to say.
ETA
Third of all,
>what helped stop repeated pressure while keeping the relationship respectful?
Ma’am, repeated pressure isn’t respectful. He’s not respecting you or your relationship. Don’t get that twisted. Don’t let him act like you’re the one being disrespectful.
A person doesn’t have to be aggressive to make you feel pressured! Stop invalidating yourself OP!
The thing is… A boundary is only a boundary if there’s consequences and a boundary does NOT need explaining!
You need to put a foot down; tell him to drop it once and for all. If he doesn’t (which I doubt he will) you need to give him a consequence.
If I were you this is break up worthy. No man who loves and respects you will try to coerce you into doing anything you do not want to. Period.
Also: HE is damaging trust. Setting a boundary is not. If a partner doesn’t respect your boundaries he sees them as obstacles to overcome and he does NOT respect you.
Or…. https://freebooksmania.com/2021/01/why-does-he-do-that-pdf-free-download-by-lundy-bancroft.html
All you should need to say is, “I am not, nor will I ever be, interested in anal. If that is something you need in a relationship, then we aren’t compatible.”
If he keeps pressing it after that, well you set a boundary already so you leave. Because someone who doesn’t respect your boundaries, especially sexual ones, is a bad partner.
If you really want to throw him for a loop, “I am not, nor will I ever be interested in having anal sex where I am the bottom. If you would like, we can try a strap on so you can experience it though.” Because he should be willing to try something he wants someone else to try. (This is a joke and just a nuclear petty option).
You said no. You communicated. You shouldn’t need to be any clearer.
To clarify, if you’re with the right partner and they are gentle it won’t hurt. If you’re with someone who is not gentle or someone that forcibly penetrates you anally it is a pain you will never forget mentally or physically.
Do not feel guilty for protecting yourself. If you don’t feel safe after saying no get out of the relationship. Now.
Edit: spelling
NO is a complete sentence. Assuming he has 2 working ears, he hears you and he doesn’t care about your feelings or discomfort, he’s a pig. Yes there are women that enjoy it, but they are the minority. He’s watching too much porn where anal appears “common” when it’s really not. Tell him he needs to try it first and see how he likes it.
No is a full sentence. If you saying no “hurts” him, he’s the issue. He is not entitled to any part of your body.
Edit to add: what’s he’s attempting here is coercion. Coerced consent is not consent. You said no. He needs to be an adult and respect that. If he won’t, its time to walk away. His behavior here is a big red flag, do not ignore that.
There’s various instagram and tiktock videos explaining how sexual coercion is rape. Perhaps send him one of those? Or perhaps get his mother to explain to him why bullying someone into a sexual act they don’t want to perform isn’t acceptable.
Or, better yet, dump him. You’re too young to settle on a man who wants you scared, uncomfortable and in pain for his own pleasure. Raise your standards hun.
He is being sexually coercive. You need to stop being concerned about his feelings and set a firm boundary that no means no and it won’t be discussed again.
Telling him you are not ready implies that one day you will be. Is this true or were you pushing off what you consider a difficult conversation? You need to tell him you don’t want to, might never want to, but if you change your mind you will let him know. If he continues to ask after being that clear you need to leave the relationship because he’s not safe.
You told him. If he keeps trying to coerce you, cut and run.
OP just tell him this magic phrase “You First!” Then start happily babbling about this ginormous strap on you will get to peg him with!
Fair Warning: There are some guys out there, that will LIKE this idea!!
Sadly my experience is, because you haven’t actually tried it, that he won’t understand whatever you say. Nor will he stop trying to negotiate terms and ways of trying. Not if it’s so intriguing that he asks so regularly.
I think your best bet is to be kinda tough and say ”It may happen in the future, it may not. You asking on a regular basis won’t change it, nothing will. You need to let it go.” And make him understand that it’s now effecting you in a negative way.
But yeah, it’s very hard to get someone to stop wanting something, with arguments that may not be true because you will only know from trying. His argument would be that it’s possible to make it pain free with lots of preparation, which is true.
So again, I think being a bit tough here is the way to go.
He’s literally harassing you instead of respecting your very clear NO!
Don’t date men who refuse to accept NO for an answer.
He wants this because he knows you don’t want it. He wants to force you to do something you don’t want because that gets him off.
He wants you to be in pain. This isn’t love and he’s not a good man.
Please value yourself more and break up if he won’t stop harassing you about it.
If he respected you he would respect your No
If you won’t save yourself and break up with him then at least tell him to never bring it up again or you’ll leave. Then do that.
Disrespectfully, fuck his feelings. If he wants to try anal he should let you peg him first…. asking once a week??? *Jesus christ*
I wouldn’t stay with a man who wouldn’t respect clear boundaries. Nothing is more of a turn-off than someone refuses to respect a boundary.
I have no idea why you are worrying about being hurtful or damaging trust when he clearly doesn’t respect your boundaries. You said “no.” That should be enough.
Tell him you’re not interested in anal and if he doesn’t drop it the relationship is over. Then if he doesn’t, dump him.
Honestly, I would just dump him before he ” accidentally slips” and then “couldn’t control himself”. We’ve read that happening too many times on here.
Genuinely, I’d offer to buy a sex toy and say you’ll penetrate him with it. See how quickly this conversation stops.
Because who the fuck KEEPS ON ASKING after MULTIPLE, never mind 1 no? He’s disrespecting you.
Anal is something that you have to 100% be into for it to be enjoyable. You need to be relaxed and when you’re tense it can be very painful. No means no. He needs to understand that.
This isn’t hard, OP. You simply tell him No. “No, I’m not interested in anal sex. If I change my mind I’ll let you know. In the meantime, please don’t bring it up again.”
If he refuses to respect you, and continues to try to pressure and coerce you, that should be an instant dealbreaker and the end of the relationship.
This gets brought up on various subs not infrequently.
Is your boyfriend into pegging? If not, then ask him to explore his own feelings of what would happen if you wanted to peg him, he was not interested, but you kept bringing it up to see if he would reconsider?
How does saying no damage trust? I dont understand. You dont want to, so tell him it’s off the table and not up for debate. If he asks again, you dump him. He’s the one being a creep, not you.
You already communicated your boundary. He doesn’t care.
The “in-between” answer is to give him a date about 8 months in the future.
Say, “We can talk about anal again after American Thanksgiving.”
The better tactic would even be: “We can talk about anal again after American Thanksgiving, and if you bring it up again in any way before then, you are choosing to break up with me.”
My bet is that he’s going to try some line about how guys “need” anal (like they need a BJ or multiple partners) and that OP is hurting him by not meeting his core masculine needs.
Nope. Nope nope nope. The next step is it will “accidentally ” “slip” into the wrong hole when you are in the middle of sex. Oh he’ll be really sorry for hurting you, he’ll apologize a million times, and you’ll genuinely believe it was a mistake.
Honestly I’d just break up. You just aren’t compatible. That’s fine, not everyone is.
“I have said no enough times now. You need to stop asking for it, no will still be no. You’re breaking my trust in you, and making me afraid to be intimate with you altogether.”
And stop having sex with that r*pist. He WILL try to force himself there once you tell him, whether my way or any other way.