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.

Anonymous: Hello! Can I ask you about butt plus for bigger girls. If you have any knowledge on that. I have a Jewell plug but it feels like the base is sliding inside me if I let go. I wrapped some cord around the base just in case but I’m really worried it would slid up. Any advice please?

Some jeweled butt plugs have rather small bases similar in width to the widest part of the plug, and if the plug itself fits inside comfortably, the base can slide in fairly easily as well. That’s probably not a really serious concern, as you should be able to get it back out quite easily if it were to happen, but if it bothers you, you might try a different plug with a differently shaped or larger base.

Anonymous: Butt plugs have the tendency to slip right out of me. They don’t stay in place and pop right out especially while walking. It’s not that I have a stretched asshole cause I only do anal occasionally and don’t use dildos in it. Maybe I just need a bigger, rounder plug? Maybe mine is just naturally more stretchable? Any advice?

This is pretty common with smaller plugs and with plugs that don’t have a big enough difference in size between the widest and narrowest parts, or if the neck is too short. Try looking for something a bit bigger or with more of a size difference in that regard.

Also, just in a general sense, assholes don’t really get stretched, despite the common use of that terminology, it’s more that with use and practice you can gain increased elasticity and relax more easily, which might make it seem as if one is “looser”, but that’s not really the case, and having more frequent anal sex/play/butt plug wear often actually helps to strengthen anal muscles.

Anonymous: I got myself a couple of plugs & tried them out, & HOLY SHIT, I never thought I’d like having my ass plugged this much! My boyfriend put the smaller one in my ass while he fucked me a few days ago, he fucked me in the ass for the 1st time last night (had to end it halfway through cuz I wasn’t super used to it & felt like I needed to use the bathroom) & when I drove him to the bus station last night I put in the larger of the two plugs & ? I was a dripping mess. Suggestions for things to try?

Yay! Isn’t it great?

I’d suggest continuing to use the plugs regularly, start putting them any time you masturbate or do anything non-anal to further develop that association between anal stimulation and other known pleasure sources, which will have the double benefit of making anal keep feeling better and better, and training your ass with the plug so anal sex keeps getting easier. Outside of masturbation, keep slowly pushing your limits with them, wearing one for as long as it’s comfortable to do so, then taking it out and trying again another day to go even longer. Keep repeating that process and you’ll keep getting increasingly comfortable with it and want more.

I’d also suggest continuing to try anal sex and other more active forms of anal masturbation more often. If it was only a bit uncomfortable and felt like you needed to go to the bathroom rather than outright being painful, you’re in a great place for your first time having anal, and with more practice you’ll be able to really enjoy it.

Hope that gives you some ideas. Feel free to update or ask any other questions you might have.

Anonymous: I’m looking into getting a butt plug for long term wear. What material would you recommend? I read one of your posts that suggested that it have a wider bulb and a narrow neck to the base, but that ones with jeweled bases (the most popular ones and the only ones I can seem to find online) aren’t particularly comfortable for long term use. What type of base would you recommend? Thanks for in advance, I can’t wait to train my ass for my boyfriend.

In many ways it can come down to a bit of personal preference and anatomical differences that vary from person to person, so it’s hard to give an answer that’s going to be suitable for everyone. Avoid materials other than silicone, steel and glass, though. A lot of lower grade materials can cause irritation or have toxic ingredients.

Silicone is softer and pliable and so some find it comfortable in that regard compared to having something totally rigid, but it can have a bit more friction so you notice it as lube dries out a bit more, depending on the surface finish of the silicone. Silicone toys can sometimes have issues with silicone lube, so are often limited to water-based and oil-based.

Steel and glass are rigid and smooth and often require less lube or can manage to stay comfortable longer as lube dries/gets absorbed. Some prefer the firmness of these materials, too.

Some possible options to consider are the Implicit Creations Core Plug (silicone, shaped for comfortable long term wear, multiple sizes), the Tantus Ryder (silicone, comfortably shaped, 1.5″ max diameter), and the nJoy line of plugs. T-shaped or loop bases are often going to be the most comfortable, and you want to avoid things with sharp edges. If you have a local sex toy store, I’d suggest going in and looking at some in person to get an idea of shape and size.

Finally, jeweled plugs can be very sexy and a lot of people like seeing them and wearing them, and even if they aren’t necessarily the best design for comfortable long term wear, they can be well worth having anyway to use in appropriate situations. And some do wear them fairly long term anyway.

Hope that helps some, and good luck and have fun with your anal training!