Anonymous: I lost my anal virginity first and I regret ever straying. But after quite a few years mistakenly having vaginal sex, my husband has decided I’ll be strictly anal from now on. I couldn’t be more excited. But I’m really nervous I’ll become weak and touch my clit. He tends to go away for work once in awhile and we can’t afford a chastity belt. Would you happen to have any suggestions for ways he can ensure I won’t touch even while he’s gone? Your blog is very inspirational btw 🙂

I think a healthy approach is to recognize that habits can be hard to break and people slip up from time to time, and that’s a normal part of the process of reaching your goals and changing your habits. Do your best, recognize if you’re slipping towards an old habit. If you catch yourself partway through touching your clit, stop yourself. If you do end up touching your clit or using it to orgasm, own up to it, think about whether it was worth it, and dive back in to not using it going forward, trying to last longer without it the next time. If you and your husband have the sort of dynamic this would be appropriate for, you can come up with punishments that you feel are appropriate for touching your clit.

That said, there are things you can do to help. Focus on anal stimulation instead. Wear a butt plug often, use your fingers and a dildo to masturbate anally, and any time you feel the urge to touch your clit, play with your ass instead. If you get that urge while playing with your ass, play harder. Fuck a toy deeper or go to a bigger size, etc., and use it to motivate you to chase anal pleasure instead.

You can also experiment with numbing cream/gel like Orajel if you really find it hard to resist. A small amount applied to your clit will numb it for an hour or so.

Congratulations on getting back into the anal only lifestyle, it sounds like it’s exactly the right thing for the both of you!

The original poster responded:

Thank you for replying! He got a really evil smirk on his face after reading the orajel suggestion haha

Anonymous: How do you get a metal plug with a round jeweled base to be comfortable? Just lots of practice? The plug itself feels great but the base really hurts my skin.

Those plugs, while great for shorter term use, aren’t as ideal for longer term wear because the wide, round base with an often sharper edge can dig into your skin and start to become uncomfortable or hurt over time. I’d suggest looking for something with a T-shaped base that’s a bit more ergonomic to wear for longer periods of time and use the jeweled plugs when you want to dress up and use it as part of a sexy outfit or show off to a partner.

Everyone’s built a little differently, so finding a plug that’s perfect for you can take a little time sometimes, unfortunately.

Anonymous: There are so many of them, but If you could name them, which are the 5 best butt plugs to wear all day?

Different plug shapes and sizes are ideal for different people, and different people have different abilities and needs, so making a “5 best” list for plugs that applies to everyone isn’t really possible. People can’t even agree on the best material for long term wear! Some prefer steel, some glass, some silicone. Some want something small and comfortable, others want something that still pushes their limits and stretches/trains their ass somewhat while they wear it.

I would suggest looking at the steel Njoy Pure plugs, silicone Tantus Ryder and A-Bomb (for a larger option), silicone Implicit Creations Core Plug, and some of the smaller Egg Plugs from Square Peg Toys.

Anonymous: Hey I’m the anon with the couples question. I’ve seen this happen with guys who want their girls to try anal. My view is I wouldn’t ask anything of someone else that I wouldn’t do to myself. So I would say take the initiative and try a plug or something too. That way it’s not one sided. I’m still curious if anyone has any ideas as to how a straight couple could both do AO… Thanks 🙂

For some that’s a viable option, and if it interests a man to explore receiving anal play himself, then that’s fine and good, great even. But not everyone is interested, and there’s nothing wrong with that either. Sexual relationships don’t have to be completely balanced in that manner in every circumstance. A man can be a fantastic anal lover for his partner without needing to get fucked in the ass an equal amount.

babybat127: So I’m pretty new to anal in general, and my Dom wants to go anal only. We’ve tried denial before and I really liked that so we’re twisting the two together and not touching my pussy much if at all, and tart touching my clit. But like I said… I’m new to anal. I know to ease into it, but I can only wear my plug for an hour or two. How do I make it easier to last through the day with it?

Sounds like a lot of fun for the both of you, and I’m sure you’ll have a good time with it!

As far as anal training and becoming more comfortable with it, you have the general idea already of easing into things. Wear your plug as long as you comfortably can. When it gets uncomfortable, take it out. The next time you do it, see if you can go a little bit longer. Keep pushing your limits and you’ll be able to go longer bit by bit over time. You can also try wearing your plug overnight, which helps you go for longer periods but without consciously noticing it as much while you sleep, so it’s easier to stay plugged. Depending on the sort of discomfort you’re experiencing when you have to take it out, it’s possible you just need to add more lube and reinsert. You can try that too, and see if it goes back to being comfortable after a few minutes removed and new lube added.

Good luck, have fun, and feel free to ask more questions if and when you have any!

Anonymous: My girl and I decided to try anal only April. She wasn’t sure at first but we’re only a week in and she’s already wearing a plug to work sometimes. I don’t think we’ll ever go back.

That’s great! If you’re both already this into it and don’t think you’ll go back, it just keeps getting better, so you’re probably really going to love it by the end of the month.

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.