Seeking Tips for Easing into Anal Play Comfortably

Vivian251

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Sep 23, 2024
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I'm in a committed relationship with my boyfriend, and we’ve been together for over two years now. But sometimes during intimacy, I get really anxious—especially when he goes all the way out and back in quickly. We’ve had a couple of ‘slips’ in the past where he’s accidentally slipped out and then gone back in too hard. Every time that happens, it’s insanely painful, and I’ve ended up almost passing out or even throwing up afterward. It’s such an instant mood-killer.

So, I’m wondering if anyone else has felt this kind of anxiety about it? Is it normal to be this afraid of it happening again?

We’ve talked about it, and he’s really understanding, but I just want to find something that might help me feel more relaxed. I’ve noticed that there are some plugs available to buy, and I’m wondering if it might be worth trying out—would starting with the smallest size be the best way to go for training myself a bit?
 
I learned a long time ago that with anal the Lady sets the timing and tone

She is in control. Not in any sort of D/s way. She is the Captain of the team and guys are expected to follow
 
Unacceptable. You're supposed to be enjoying it, not crying or puking.

I don't criticize you for wanting to do more by yourself to try to fix it (it often seems like the easier route) but this really does sound like an "us" problem, maybe even just a "him" one.

In fact, I'm going to reassure you: That you let him back in means you're giving as much as a recipient ought.

Sorry if you wanted a magic bullet, but there's none I see. You deserve his devotion--you've already paid for it. (Ow.)
 
If I hurt my wife during anal I would feel so bad and I’d never try it again, if it’s not great for both then it’s not worth doing.
I have no desire for her to do something painful or uncomfortable for me because it’s something I wanted to try.
Also anal sex isn’t that spectacular, not worth her not enjoying it.
 
I just want to find something that might help me feel more relaxed
You can feel more relaxed, but nothing is going to prepare you for the battering ram you're describing or allow you to "ease" it in there when it's hammering like that.

Don't make this your job. He needs to get it under control. I can't believe he's still doing this after seeing you repeatedly pass out and puke from it.
 
Get a strapon and show him how it feels!
A lady that I play with at the moment is very wary of anal but was happy for me to do the deed because I have a lot of experience but primarily because I've been fucked and I know how it feels from the other end.
 
I'm in a committed relationship with my boyfriend, and we’ve been together for over two years now. But sometimes during intimacy, I get really anxious—especially when he goes all the way out and back in quickly. We’ve had a couple of ‘slips’ in the past where he’s accidentally slipped out and then gone back in too hard. Every time that happens, it’s insanely painful, and I’ve ended up almost passing out or even throwing up afterward. It’s such an instant mood-killer.

So, I’m wondering if anyone else has felt this kind of anxiety about it? Is it normal to be this afraid of it happening again?

We’ve talked about it, and he’s really understanding, but I just want to find something that might help me feel more relaxed. I’ve noticed that there are some plugs available to buy, and I’m wondering if it might be worth trying out—would starting with the smallest size be the best way to go for training myself a bit?
I've had two horrible experiences with anal and I've never been able to get past the mental block. It's ok to not like anal sex for whatever reason. And if your bf is pressuring you even though it hurts you enough to make you pass out/throw up, then he sucks and you should move on.
 
A lady that I play with at the moment is very wary of anal but was happy for me to do the deed because I have a lot of experience but primarily because I've been fucked and I know how it feels from the other end.
I have a story like this, basically an "I will if you will" type scenario.
 
I'm in a committed relationship with my boyfriend, and we’ve been together for over two years now. But sometimes during intimacy, I get really anxious—especially when he goes all the way out and back in quickly. We’ve had a couple of ‘slips’ in the past where he’s accidentally slipped out and then gone back in too hard. Every time that happens, it’s insanely painful, and I’ve ended up almost passing out or even throwing up afterward. It’s such an instant mood-killer.

So, I’m wondering if anyone else has felt this kind of anxiety about it? Is it normal to be this afraid of it happening again?

We’ve talked about it, and he’s really understanding, but I just want to find something that might help me feel more relaxed. I’ve noticed that there are some plugs available to buy, and I’m wondering if it might be worth trying out—would starting with the smallest size be the best way to go for training myself a bit?
First get some numbing lube and next make sure he knows that you control what happens if you want to stop stop. Talk about what feels good. I now love anal sex and at first was really not into it but over time and a loving husband that always respected my stops and gos and let’s try this I have become a real anal pro. Don’t give up it can change your sex life for the better but if he can’t understand he needs to listen to you and your body maybe you do need to take it off the table.
 
I'm in a committed relationship with my boyfriend, and we’ve been together for over two years now. But sometimes during intimacy, I get really anxious—especially when he goes all the way out and back in quickly. We’ve had a couple of ‘slips’ in the past where he’s accidentally slipped out and then gone back in too hard. Every time that happens, it’s insanely painful, and I’ve ended up almost passing out or even throwing up afterward. It’s such an instant mood-killer.

So, I’m wondering if anyone else has felt this kind of anxiety about it? Is it normal to be this afraid of it happening again?

We’ve talked about it, and he’s really understanding, but I just want to find something that might help me feel more relaxed. I’ve noticed that there are some plugs available to buy, and I’m wondering if it might be worth trying out—would starting with the smallest size be the best way to go for training myself a bit?

My wife is the same way. Getting it in to her ass is painful, the after it’s in I stop for a second until she’s ready. Then she loves it. But I’m not ok with hurting her so I don’t ask to do it. Every once in a while mostly when drinking she will ask me to. We use lots of lube. We have a lube injector that we use also.
 
Having been lucky enough to have my husband of over a quarter century, we have begin relearning anal play after a brief stint or two some years ago.

Our suggestions are simple and easy to implement.
1. Communication is most important. Verbal feedback or hand signals are necessary for the man to understand what you are experiencing.
2. Lube! When you think you have enough, add more! The exception being numbing lube. Don't get me wrong, it's great at the start to take the edge off, but it will affect HIM too. You could easily get poked painfully if he's too numb to feel where he is on the out/in stroke. The lube I prefer in quantity is the Wicked gel relaxant lube. It works to relax the rings so that they're not so tight and subsequently painful. The 3rd lube we like, esp once things get rolling, is Wicked Hybrid. It's less prone to drying out.
3. Toys in first! Start on the smaller side with toys. But toy in before boy. My husband enjoys watching me take the toy, and he switches them out for the next size up at his discretion. He them checks if I'm ok, assuming I have a shown negative reaction. We use a combo of verbal and hand signs for me to communicate with him.

4. On those times where the angle for penetration is not right for me and I lurch fwd, he knows something is wrong and stops moving and asks me. Once he adjusts the angle of penetration, it stops hurting.

You mention the problem for you is when he pulls out completely and then slams back into you. Does he slip out accidentally? Or is it possibly deliberate and he likes the powerslam re-entry? Or is he just too excited and focused on his feelings/impending orgasm? Two of those you both can work together to resolve. One of them would make me refuse anal with that person.
 
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