daddysprincessdiana: My husband and I used to have anal be our main kind of sex that we had. I would wear a butt plug every day, and we would only have vaginal sex if we forgot what it felt like. Then in March last year it started to hurt. Really badly. And we had to stop. Since then we’ve tried every couple of months, but it’s gotten to the point where even my smallest plug hurts. Do you know what could have caused this or what I could do to make it stop hurting? I miss anal

I’m sorry to hear that, that’s terrible. What sort of pain is it that you’re experiencing? Is it a sharp, stinging pain, a burning pain, or something else?

It could be a hemorrhoid or fissure that hasn’t fully healed or keeps getting irritated again.

It could be a sensitivity to the sort of lube you’re using or one of its ingredients, which can cause a lot of pain for some people. If you’ve tried multiple lubricants and it even hurts with natural lubrication as well, that may not be the case.

It could be a combination of factors with one primary trigger initially as well combined with falling out of the routine and things that were once easy because you were more relaxed and in the habit of doing something are hard to get back into now even if the original issue has healed.

Ultimately, I would suggest visiting a doctor about the issue to get a better understanding of what the cause is and see how you can proceed forward from there.

k-azile: Would it be good training to leave a plug in while you sleep?

Absolutely, so long as it’s a comfortable plug and has a safe design with a base wide enough to not slip in. If you’ve never had that issue before, it should be fine. It might take multiple nights before wearing it all night is comfortable enough to do, or it may work right away.

Anonymous: Are there medical reasons why someone can’t have anal sex? I’m a guy and have a fair bit of personal experience with anal sex but my gf is an anal virgin. We bought an anal training kit with three plugs in it and she can’t get beyond the smallest plug because she says it hurts too much. Any advice apart from the obvious like relaxing and using lots of lube?

Some people may have various conditions that make it more difficult, but most people can get to the point of enjoying anal eventually if they’re willing to put in the time and effort. For some people, that’s an incredibly quick and easy process, while for others it’s slow and challenging.

As a general rule, start where it’s not uncomfortable or painful for her. If she can use the small plug without it hurting, focus on that for now. Don’t advance to the next plug until she’s totally comfortable with this one. Combine some other things like rimming and light rubbing or fingering to help her relax. Add clit stimulation if she enjoys that and try to get her to start orgasming in combination with anal stimulation and/or penetration.

Then, when she’s comfortable with and enjoying the small plug, try the next size. If it still hurts, go back to the smaller one or try something a size in between (this could be a finger/thumb in some cases) before trying again. Go back and forth until the plug can fit in without pain. Repeat this process as needed.

slutty-sissy-slave-jessica: Thank you for your answer to 24/7 plugging. Do you have a recommendation what size and length you should end up with for 24/7 plugging? What would you consider best if their is no problem concerning pain etc.

That really depends on your goals. If you just want it to be something in your ass and feel good, it would depend on your personal level of preference for size, and may be on the smaller side of things.

Something like an Njoy or jeweled plug (though the latter have a base shape that isn’t always comfortable for long-term wear) can be good for a small plug that doesn’t do much active “stretching” but just remains in place in your ass and does help a little bit with relaxation and warming up just by its presence even if its size isn’t as big a part of it.

If you want it to be more of a training plug as well as good for long-term comfort, something like the silicone Tantus Ryder, an Implicit Creations plug, or a glass plug with a thicker neck might be more appropriate.

If you like to continue pushing your limits bigger and bigger while also being really comfortable long-term, a bigger Implicit Creations plug, a Tantus A-Bomb, or something from Square Peg Toys or elsewhere may be appropriate.

It can be hard to say where someone wants to “end up”—I would choose a plug that’s an appropriate size for where you are now, possibly pushing a little towards the larger end if you want to go bigger. In the future you may find yourself wanting something bigger, at which point you’d look again for an appropriate size from there.

Since everyone’s so different in this regard, I often recommend going to a local sex toy shop if you’ve got one available so you can look at the size and shape in person to make an appropriate judgement. I recommend sticking with only silicone, glass and steel toys, none of the cheaper materials—especially for plugs.

slutty-sissy-slave-jessica: Is it save to wear plugs with thin necks (like jewel plugs) full time 24/7?

Yes, absolutely. The only concern with long term plugging is that the base is wide enough that it doesn’t slip inside unintentionally and that it stays comfortable. If it starts to hurt, you might take a short break or figure out what’s causing the pain/discomfort, but otherwise feel free to plug as often as you like. It won’t hurt you as long as you listen to your body and adjust as needed.

Bigger plugs with thicker necks are fine to wear long-term as well as long as they’re comfortable. It won’t cause issues, even long-term. It will help relax and “stretch” your ass, but anal muscles default to a closed state, so even if it can stay open at a very large size with a plug, it will close back in its resting state when not plugged.

Anonymous: I’ve rarely done anal and never done anal only before but Anal Only April was too tempting to pass up, especially since the first was Easter. I brought it up to my husband ahead of time but I bought a bunny tail plug and after Easter festivities were over and the kids went to bed I surprised him with a Playboy Bunny outfit. We’re planning on the whole month but for tonight I’m happy I’m going to bed wet and with a load of cum in my plugged ass.

Sounds like a sexy way to kick off a fun challenge! Keep us updated on how it goes.

Anonymous: I wore my butt plug to class for the first time today. Sitting there with it pushing against the seat while I tried to remain as attentive as possible made me sooo wet. I can’t wait to do it again. I’m thinking about wearing it in the shower and overnight tonight so I wake up a horny, dripping mess. Are there any problems with doing that? I’m fairly new to butt plugs.

Isn’t it so much fun to wear in public and feel your ass full and sensitive and occupying your attention?

There’s no problem with wearing a butt plug long term or overnight. If it starts to get really uncomfortable, you might take it out, but otherwise go for it. Sometimes, some people can’t go all the way overnight with one immediately and it can take a little practice, but try it and see how it goes!

Anonymous: Hey I’ve been following you for a while and I can’t help but agree with you about your views on anal sex. When my GF was into it I absolutely loved giving it to her and I’ve always loved anal porn. Today I had the house to myself and decided it was time to try her butt plug as I edged and it was AMAZING. I can see why it’s addictive now. I nearly exploded when I could take it with ease (didn’t take long). Why have I waited so long?! Question is, do I tell her? I’m a (straight) guy btw…

Anal pleasure can be a lot of fun for women and men both. I’m not one to say that every man needs to receive anal stimulation if he wants to have anal sex with women, but I encourage anyone to try it if they’re interested.

As for telling her, that really depends on your relationship and how you think she’ll react. I always lean towards being honest and open, and if it’s something you enjoy and want to pursue further, you should share it with her.

You also mentioned that you used to have anal sex with your girlfriend when she was “into it”, which suggests that she isn’t anymore and you no longer have anal together? Why not? What changed?

Anonymous: How will I know when I’m ready to get a bigger butt plug for extended wear? When I’m comfortable wearing the one I have for long periods of time? And how big can I go for long term wear without worrying about having to clench to keep it in?

Exactly, if the plug you have is comfortable and easy to wear long term, you might be ready to try going up in size to a bigger plug.

How big you can go is very dependent on your current level of ability and comfort and the general shape of the plug. It’s more the ratio between the widest and narrowest part rather than a maximum size that dictates long term comfort and retainability. There are people who use plugs over 3″ wide at the widest point and 2″ at the narrowest long term, and find that comfortable. So it really depends on a lot of factors.

Anonymous: Quick question: how can I increase the size of butt plug I’m able to take up my ass in a fairly timely fashion? Would love to be able to tell my boyfriend my ass is ready for him right off the bat rather than having to spend time stretching me out for a bit first

Masturbate anally on a regular basis, in addition to frequent plug wear. Use fingers and dildos, and keep pushing your limits with size. As you keep doing so, switch to a bigger plug once your current one is regularly comfortable to insert with ease.