quietsilentlove: Thanks so much, I didn’t know about the push while I insert something so that’s a new bit of info. Also will the jewel plugs work too I keep reading mix reviews on them about long term wear. Or should I stick with a softer material? Or should I just buy one of the kits that has the three different sizes? And do you have a favorite lube you prefer?

Jeweled plugs can look sexy but are often not comfortable for long term use. They also have a very narrow neck, generally, so once they’re inside they’re not doing much to stretch and relax the anus itself. Perfectly fine to have one as a sexy accent, but I wouldn’t use it as a primary training tool. Some of the training kits can be fine, but I find that using fingers to train instead is easier and then invest in a good mid-sized plug instead that you’ll want to keep using for a long time.

Lube is a bit of a personal preference. There are plenty of good water-based lubes, silicone lube can be great but cannot be used with silicone toys, and coconut oil is popular with a lot of people.

Anonymous: I’ve always been interested in anal, I even bought plugs. However, I can never wear one for too long because I end up feeling dirty. Do you have any tips that could maybe help me be more dedicated?

Dirty in the sense of hygiene or feeling bad/ashamed?

If the former, go to the bathroom before and you’ll be okay most of the time.

If the latter, it can take some time to work through. Always tell yourself there’s absolutely nothing wrong with what you’re doing. It’s important to consciously believe this—but that’s often not enough, and people can still feel bad after doing certain things even if they enjoy it and don’t have any rational reason to feel that way. Being aroused tends to keep that feeling of doing something wrong away, and then there can be a crash after you orgasm where you feel shame, even if you have no reason to be ashamed about anything.

To start out, put in your plug and masturbate while wearing it. After you orgasm with it in, try to keep it in for as long after as you feel comfortable doing so. This may not be very much time at all at first, which is fine. The important thing is to try and keep pushing that limit. As you get further along with this, you’ll get more comfortable with having something in your ass in general.

Another alternative is to experiment a while with keeping yourself in a longer term state of arousal through either edging or ruined orgasms, neither of which give the same amount of crash as a normal orgasm. These aren’t necessarily for everyone, though, but may be useful in the short term just to provide you with a period of time to experiment with anal play while being more aroused and thus more open to it.

Anonymous: My bf loves to fuck my pussy. Should I anally service him more? Should I just beg for anal every time we have sex? Should I beg him to try my ass only for a fortnight? Please tell me how to be a better anal slut and help him appreciate my ass more.

Let him know that you’d enjoy having more anal. Communication is always a good start. You can suggest trying No Pussy November (coming up in just a week) with him. Wear butt plugs around him and when you have sex so he knows you like having something in your ass. Helping others appreciate the joys of the anal only lifestyle is a very positive thing!

It’s nearly that time of year again, so start making plans! If you already enjoy anal and going anal only is something you’ve thought sounded interesting but haven’t tried yet, this is the perfect opportunity to give it a one month trial run and see how it goes before making any bigger decision about it.

Those who are already anal only could choose some other variation on it, such as going the month without clitoral stimulation, or only edging clitorally with no orgasms unless they come from anal.

Those who do not yet have experience with anal can take the opportunity to train and practice over the course of the month with fingers and toys, working up in size until you’re ready for anal sex.

As always, feel free to ask any questions along the way or share your plans and progress!

Anonymous: Hello! So anal only August was a bit of a fail for me and my Master… We both got very busy so I didn’t achieve the gape we were both aiming for by the end of the month 🙁 but I am determined to try again! I am currently sitting here plugged with no intention of taking it out until bed time 🙂 if I stay committed, I can achieve the gape we BOTH want!!!

Glad to hear you’re sticking with it. It’s a process, and it’s not at all uncommon to drop it and come back later to try again.

Anonymous: I’m 4 days into being locked in chastity now, with no plans for future orgasms unless I can learn to cum anally (I’ve sort of had anal orgasms before, or something along those lines, but I can’t easily reproduce them). Before the full chastity I had about 50 days where I never came unless I had a plug or dildo in my ass at the same time, which I really enjoyed and I feel like I could do that forever. But now I’m upping it to full on anal only, and I’d like to be able to do this forever too.

misslutification: Yay!… Don’t give in. Thats the hardest part for me. My clit throbs for attention constantly. One of my followers told me when my clit throbs and my pussy aches try to keep fucking my asshole. Everytime i get horny to play with my asshole. It really helps actually. So when i get horny instead of thinking “touch pussy” i think “touch my ass”

silvercrow503: Hello I need training advice. My hopeful sub is embarrassed by the idea of having something up her ass constantly. Any ideas on how I could reassure her and make her more comfortable during the starting phases of the plug training? Thank you

If she’s just starting out, she shouldn’t really even being considering wearing a plug all the time. It’s fine for that to be an eventual goal, but initial training should focus on making it comfortable and enjoyable, the hopeful outcome being that she ends up enjoying it enough she may become excited about the idea of wearing a plug more long term. Start just with anal play (fingers and/or toys) during other sex acts she enjoys and gets pleasure from, then slowly have her wear the plug at other times, perhaps while masturbating on her own at first, then sometimes around the house for half an hour at first, and working up in time from there.

kinkyflo: Hello again 🙂 Im getting annoying yet?? Since I’m really loving my plug and the feeling of having my ass full I wanna buy another one and since you are the expert I want to know if you could help me… I’ve seen the princess plugs all over tumblr and I do think they are beautiful but Im wondering which material is better stainless steel or glass? Specially for a long period of time. Thank you so much!

Questions and requests for advice are never, never annoying and always welcomed from everyone!

Both stainless steel and high quality glass can be good materials for plugs. Some people have a fear of glass breaking, but I haven’t ever heard of that being a problem with a properly constructed plug. Both are hard materials with no give to them, obviously, which is a different experience from something softer like silicone, but a lot of people love it. They’re both also quite slick and so can stay comfortable longer without needing to reapply lube as often, something other materials may not do as well.

The majority of jeweled plugs are going to be stainless steel, but there are some glass ones too. Due to their huge popularity, there are a lot of cheap and poorly made ones flooding the market lately, so shop around a bit. The cheaper ones may work fine, but be very careful to check for defects from the manufacturing process that may create a sharp edge or burr before wearing it.

Also consider that a jeweled plug may not be designed for long term comfort if you want to wear it for an extended period of time. That doesn’t mean they’re bad at all, and you can certainly wear them comfortably for quite a while, but you may want to consider a different and more ergonomic design if you’d like to start wearing plugs long term. If you enjoy plugs, no doubt you’ll end up with a collection of several different ones for different purposes!

kinkyflo: My anal plug just came in the mail!!! Is my very first and I´m super excited and I wanted to share it with you since I´m taking notes from all your tips and getting all aroused with your post 🙂

I’m so glad! Good luck and enjoy, I’m sure you’ll have a lot of fun with it!

Anonymous: Since taking your advice on butt plugs, I haven’t even had my butt plug for three days and my ass is ready to take a very big and very thick cock. I’m ready to go anal only. 🙂

I’m glad to hear it. I would also suggest using a dildo in training, because while being able to fit a certain width plug is an important part of the process, you do also want to train for the in and out motion of sex. Keep it up, and take the anal only plunge.