Anonymous: How long is too long to wear a butt plug?like what if I fell asleep with a tail in?

As long as it’s comfortable. If it stays comfortable, it’s fine to keep in. The more you do it, the longer it will feel comfortable to keep it in.

Anonymous: I actually have a couple questions if you don’t mind 🙂 Q1. I’m looking to stretch my hole and create a cute little gape, how do you suggest going about this? I know to use plugs but I’m not sure how many times and for how long! Q2. My Master and I are thinking about participating in AO August, however, we haven’t done much sexually in quite some time. I’m craving it but not sure if I could handle a whole month. Some tips? Thank you! 🙂

1. A gape is something that becomes possible as you gain greater muscle control and can relax at will, generally in combination with recent anal sex or play to help temporarily relax the other involuntary muscles around that area. Just keep training with plugs and dildos as regularly as is appealing to you. Wearing a plug while you walk around and do other things can really help develop muscle control as you retain it and keep it inside you. It’s up to you and your body how long you keep one in per “session”. Do it for as long as it’s comfortable or you are otherwise able, then take it out and put it back in at a later time. Over time, the duration you can comfortably wear a plug will increase. You also, of course, want to make sure you have a plug that’s comfortable to wear for longer than a few minutes and which stays inside easily and comfortably without wanting to pop out all the time. As you stick with this, gradually increasing the size you can fit, you’ll be able to relax more easily, and as you can do that, you’ll find yourself able to gape your ass.

2. Anal August doesn’t have to be a whole month of anal. It can serve as a first introduction to anal only of whatever length works for you. If you’re worried about a whole month, try a week or two. (And you could of course continue after that if you wanted.) Anal August is something that’s been around for a few years now, unrelated to and before this blog existed, and isn’t strictly Anal Only-specific. If you end up enjoying whatever duration of anal only you try and then want to go for a full month, keep an eye out for announcements later this year for the third annual No Pussy November, an actual full month anal only challenge. (Or try it on your own anytime!)

Hope that was helpful in some way, and feel free to ask more if you have any other questions.

Anonymous: You seem to quite knowledgeable in all things involving ass play, hopefully including using butt plugs and training your ass? I have a lot of questions and do not know who to ask. I’ve got a bit of experience in anal, but I want to train my ass to accept a dick more easily. Right now, it’s a slow entrance with lots of lube before we can get to the good stuff. So I’m wondering where do I start, how long to keep it in, and what to use, etc? Thank you.

Anal training in the long term and anal warmup before sex in the short term are both really quite simple in theory. You start with something small and work up in size. When the transition to something larger feels uncomfortable or hurts, you’re not quite ready to go to that size yet and should either go back to the size you were using before or a size in between for a while before trying again.

Train as often as you can and feel up to it. Daily is fine if you’re able to do it, but a few times a week works as well. If you injure yourself at any point by sizing up too quickly, however, take a break from the training for a few days to a week.

You want to have a few different toys, both plugs and dildos of a few different diameters. Don’t bother with anything too small—tiny plugs don’t stay in place, and you can use your fingers to warm up at that size instead, plus you’ll outgrow small things rapidly. Get good quality materials—silicone, glass, stainless steel. Every time you masturbate, have something in your ass at the same time. Wear a butt plug when having other sorts of sex.

As you do this more often, you’ll develop more conscious muscle control and can loosen up “on demand”, as it were, by pushing out as if going to the bathroom while being penetrated. Chances are you already can do this to a certain extent, but the ability increases with training. Not all muscles in the anus are able to be controlled consciously, however, so wear a butt plug for 15 to 30 minutes before having sex and it will also greatly aid penetration with a partner.

kinkyflo: I’m so glad I found your blog, I really like anal sex but I want to be a better anal girl. I just bought my first plug to start training and Im super excited and all the amazing advice you give is making me even more excited, since now I have a better idea of what to do.

I’m glad to hear it! I’m sure you’ll have a lot of fun with the anal training. If you have any other questions along the way, be sure to ask.

Anonymous: Anal sex with the last few partners I’ve had have been dirty/messy experiences. When i look down and see it happening it’s about as big a turn off as they come for both parties. I love fucking a woman’s ass but I feel like the reality of anal sex is very different than the super clean porn we see online. Do you have any advice on this?

Anal in porn is alway preceded by anal douching if not full blown enemas. In reality, while most people will be mostly clean most of the time assuming a healthy diet, etc., there is always the possibility of encountering fecal matter unless also doing anal douching beforehand. Some people don’t want to encounter any sort of mess when having anal and so douche every time. If done correctly, just flushing out the rectum and nothing beyond, this can be very effective, but too much or too deep and it can create a greater mess as well as pose a potential health risk if done too deep too excessively due to creating an imbalance of good bacteria essential to the digestion process. So I highly recommend reading up on the pros and cons of doing such a thing.

Otherwise, healthy diet, go to the bathroom an hour to 30 minutes before, and insert a butt plug 30 to 15 minutes before—the last helps with warmup and “activates” the colon a little bit, which can help move anything close by along that might potentially cause a mess during sex.

Anonymous: Isn’t it so satisfying to have the large plug stuffed in your asshole? It’s like it immediately turns your cunt into a faucet! I love that feeling!

scaredfeminist: Haha yes that’s so true! Just a moment of discomfort shoving it in, and then my brain scrambles and my mouth waters and my cunt swells!! It’s amazing the effect it has. Honestly anal is more pleasurable than vaginal in many ways. It’s like vaginal was just pushed on us for puritanical purposes and anal is like the purest form of pleasure for everyone.

alexamindslave: i completely agree. ANAL is the purest form of pleasure. it is literally the best sex. you should ALWAYS masturbate with something inside you. if you keep doing it, you will eventually actually crave that moment of discomfort because your body and brain will know what pleasure is just about to happen.  i am so addicted to anal i keep something inside me almost all the time. sleeping. work. all. the. time. i literally cannot imagine going a day without something inside me. anal forever!

Anonymous: is bad to leave a plug inside my butt all day? (taking it out just for the obvious and lubing).

Not unless it hurts. If it hurts, you should take a break. Otherwise, you’re fine. It’s not going to cause any sort of permanent looseness or anything, but it could put pressure on nerves depending on how it’s shaped and what positions you’re sitting in, etc. Plenty of people do it without issue, though, so give it a try and see if it works for you. One plug might be uncomfortable all day while another might work just fine.

Anonymous: lately i have been having lots of anal sex but always its kinda awkward and painful at the begining so i have been thinking about buying an anal plug, any recommendations on how to pick one or other methods to keep my fuckhole loose?

Butt plugs are great, both for additional play and for training purposes. As with any sex toy, you want to get one that’s a body safe material. Silicone, stainless steel and glass are all good for this. I would generally recommend silicone starting out, but everyone has different preferences. Note that with silicone toys you generally cannot use silicone lube. The Tantus Ryder is a good small/medium plug to start with—about 1.5″ diameter at its maximum—and only about $20. It’s a good shape for longer term wear if that interests you, but it should work well as a warmup before sex as well. Over time you may want a larger plug as well, and there are plenty of different good options out there. Pretty much all Tantus products are great, but there are other good brands as well. Just stay away from the cheaper materials, especially jelly. They can cause adverse skin reactions or worse.

You don’t necessarily want to (and won’t) actually stay loose all the time, the key is training yourself to be able to relax at will, and then going through a warmup process beforehand each time to ensure you’re relaxed and ready for sex. For many, a butt plug worn for 15 to 30 minutes before sex, often during other foreplay, works great for that purpose.

Anonymous: Sitting with my pussy clamped shut and my butt plug in just scrolling endlessly through your blog. Best night I’ve had in a long time.

Excellent, I’m glad to hear it. Keep it up and have fun!

sillysexystupid: My butt always feels so empty after plug time is over. I’m barely on day 5 of Butt Month, but having something inside my ass feels like my new normal.

That’s the idea. Before long it may be all you want, and if you do it right, you might even learn to need something in your ass in order to cum.