Seeking Tips for Easing into Anal Play Comfortably

Yeah I didn’t read any of that. I’m a woman. I hate anal sex. All the numbered lists in the world won’t change my feelings on it.

OP may be the same.
I understand, I am not trying to advocate anal sex; I am only trying the indicate what is involved. What is involved may make a couple decide that it is not for them.
 
The list post was very TLDR and a lot of it was not relevant to the question.
Key things are lube, both you and the one who is going in, and prepare the way by using a smooth, moderately-sized, skinlike-surfaced butt plug until you feel comfortable. As well as lubing, use a lubed condom. It all helps.
 
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 have no real advice, I’m no expert. I didn’t really know any of the guys very well, that I did it with. And we didn’t use a huge amount of lube either. But I was very keen to do it. If you are struggling so much, I am wondering if you really want to do it. Perhaps you should avoid it all together. Good girl for giving it a good go, but don’t make yourself ill over it - physically or emotionally/mentally. Just don’t do it. Or take a break and only try when/if ‘you’ want to. Good luck
 
Anal isn't one of my favorite things so take my advice with a grain of salt I suppose.
Like others have written...
Lube. When you think you have enough, add more.
Go slow.
You should be the one in the driver's seat. Not your BF.
If there's pain. Stop. It's the biggest reason we don't do anal except for small toys, fingers, plugs, etc., while hubby and I are "gettin' busy".
I'm not a fan of numbing gels. I've always felt that there's a possibility of injury that might be masked by it. That's just us.

MP
 
Unlike Bond I enjoy anal. Bond does give good advice too. the receiver is 'in the drivers seat'...totally! Add lube and go slow.
 
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?
Our anal sex life is also not harmonious
 
Ours is starting to be quite enjoyable for both of us, after the age of 60. She said it's because there is some foreplay and I think it's also because I've switched to pure coconut oil as a lubricant.
 
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?
If it is a mismatch problem with vaginal penetration, dilators can help with the training.
 
There's only one thing you need - a considerate boyfriend.

If you're already doing anal and he's not doing it right, and you've talked about it, he's not as understanding as you think he is. You need to train him, not you.
Absolutely. You train him or no more pucker!
 
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.
This isn’t a mood-killer it’s borderline assault. Any guy who did that to me would be history very quickly.

Anal sex isn’t something to be approached lightly or without due care and consideration. It appears your BF has neither.

Said as someone who enjoys anal as part of her sex life.
 
I do think that the idea of any guy having to agree to be pegged by a woman before being allowed anal sex with her is inherently sound. And fun as well!

And you guys have prostates too, even more stimulating.
 
I do think that the idea of any guy having to agree to be pegged by a woman before being allowed anal sex with her is inherently sound. And fun as well!

And you guys have prostates too, even more stimulating.
Absolutely - I just need to find a lady that is into pegging! Surely not much to ask is it? Well, actually it's akin to trying to find a bloody Unicorn!
 
Absolutely - I just need to find a lady that is into pegging! Surely not much to ask is it? Well, actually it's akin to trying to find a bloody Unicorn!
I can’t claim to be an afficiando. Had one partner who liked it. My SO, not so much. Then he’s perfect in every other way 😊.
 
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