Butt plug

Relax, go slow, use plenty of lube.
Start with a finger or two before you insert the plug.
Listen to your body, if things starts to feel dry back there, take it out, add more lube, and re-insert it.

 

It probably won't help if you have to have it in this week, but one thing that made a huge difference for me was the discovery of anal lube as opposed to conventional lube. Really thick gooey stuff that just stays there - it's more expensive but worth it and available in most adult shops as well as online.

You may also find it easier if you lie on your side and bring one knee right up to your chest when putting it in the first couple of times.
Good luck.

 

Go for short periods initially too. You will find pressure begins to build, that is your body’s way of trying to behave normally by expelling whatever is back there. The period when you try and expel will increase over time.

it shouldn’t be painful, when you start to feel discomfort, remove it and give yourself a break.

 

You might also want to wear tight fitting pants to hold it in place when walking or working in the garden

 

Take it slow, use lube and if it gets painful or uncomfortable take it out, build up slowly (0: well within the time you’re permitted).

As someone else mentioned, tight pants will help if you’re moving around a bit, amazing how hard it is to get in and how easy it will come out when you’re not expecting it.

 

1- clean that hole
2- lube, lube, lube
3- start small, work your way up to what she wants in there
4- go slow and easy while 'breaking in'
anal play takes some getting used to. my holder get's a kick out of having me plugged, her favorite thing is to lock a plug in so I cannot do anything about it being in there and have to request permission to unlock whatever is holding it in.
This thread doesn't seem to be about the why.. but for me, she enjoys being 'full' herself with dildos and plugs, so, she frequently locks 'intruders' in herself with her belt, and likes me to experience the same thing, and it be because she wants me to do it.

 

Probably a bad idea to have it in for an extended period of time if you have never had one in before... Unless your keyholder is under the impression you have experience with things like this... maybe she needs a bit of a reality check. Sorry man.

 

If you're going to wear it for a while doing stuff, I've found that a plug with a narrower base is more comfortable and sits better between your butt cheeks. She bought you a medium, but you might want to go out and get yourself something smaller, to begin with.

Also, please don't cheap out on the materials. Please look at products made of medical-grade silicone and such. They're much easier to clean.

 

I'm sure you can achieve what she is asking, but doing it by THIS weekend might be overly ambitious. Ideally you should start with a small plug and work up in size. Likewise You should start with short sessions and work up to longer and longer ones.

For your own safety, you need to take it slow and listen to your body. If you feel pain (not discomfort) then something is wrong and the plug should be removed. After the source of the pain is identified, and the problem addressed, you can try again.

If you are new to anal play, then I cannot stress enough ...Lube is your friend ...You should never feel dry inside, if you do remove the plug and add more lube. Once the plug is safely and comfortably home in your butt, you can wipe away the excess lube with tissue and get dressed.

 

A few words on anal play for a beginner:

(1) it is possible to injure yourself in a way that makes it really difficult to engage in anal play in the future. Go slow! Use a finger or small toy, give your muscles time to relax and get used to the insertion, then fuck yourself a little to get them looser and more open. ONLY when you can push in with no problem and no feeling of stretch or pain should you move on to something bigger. If you can't easily reach your ass to play with it, you might need to ask for your Mistresses help, a good Domme should be willing to facilitate an honest request for help in fulfililng her wishes (especially when not doing so can incentivize a sub risk injury).

(2) Like Alana said above, lube is your friend. Water based lubes can kind of suck, dry out, and become tacky. Silicone based lubes are generally the highest quality, they stay wet and they don't wash off easily. Gun Oil is a great lube for anal play. Natural oils can also be really good, coconut oil especially (and it's also the cheapest lube option by volume).

(3) BUT be careful with your toys. Each toy should come with a description of what it's made out of and what lubes you can use on them. A lot of toys are silicone or rubber and can be degraded with silicone or oil based lubes respectively. And you don't want the veneer of a toy to come off inside your butt. If you can't use a certain kind of lube on a toy, just put a condom on it to protect the surface of it from the lube.

Finally, this is not sponsored content, just a sincere recommendation. If you and your Mistress are going to start enjoying the pleasures of your butt, you should try the Aneros Helix plug. It's incredible, it's a butt plug designed to let you massage your own prostate by flexing and relaxing your PC muscles. It's both pleasurable, and it helps you learn how to control your muscles down there, and where and how to manipulate your prostate. I tell AMAB people that it helps them "find their cunt" and learn how to work it.

https://www.aneros.com/product/helix-trident/

And most importantly, have fun!

 

I’ve found a tight fitting diaper keeps the plug in (no room for it fall or push out) and the diaper absorbs all the dirty lube that seeps out of the sides of the plug.

 

That's cool. A lot of the store bought especially lower end plugs suck for long term use. One available online and through Amazon if you want ships relatively quickly is called bootie by fun factory. It's not large but is more suitable for long term wear. And it's design targets the prostate very specifically. You would have no issues with this one slipping out either. As long as she's on board I'd go with it. The thought was awesome but I wouldn't wear that one too long. More suited for shorter bedroom sessions.

 

I agree, anal lube is game changer!

 

+1 on the Aneros Helix - I am wearing mine right now. All my other plugs give different sensations, but this is the one where I can manipulate it just by clenching. It's also easy to manipulate by hand, and heavenly when a vibrator like the Wand is held against it.

 

Take your time. Short periods at a time. (Anal Training ) and the right size plug. You don't want anything to long to start. I went through anal training 5 or 6th months ago and I am now to the point that 8 hrs is nothing and I forget that it is in. If you go through the right anal training you will be doing chores with it in. IT TAKES TRAINING . You need to show her the many responses from this post that say that. Well good luck .

 

It is not unusual to leak a bit if your plug (or anything else) is rubbing against your prostate. Some of us enjoy the feeling
A little more lube might help it slip right in.
A Warm moist towel is handy to wipe away the excess lube once it's in.

 

I think I said you need to start out smaller in length

 

yep that is totally normal. Welcome to the fun side ;-)~

 

You may be trying to do too much too soon.

Plugs come in a LOT of different shapes sizes and materials for a reason. Your best bet may be to find the same plug in a slightly smaller size. Once you can wear that plug without any discomfort, remove it and immediately replace it with the slightly larger size. (You can find training sets of 3 or more plugs made for this purpose)

I think once you have satisfied your Keyholder that you have conquered that plug, you may want to ask her to let you explore your options with different shapes and materials. My guess is that there is a better plug for YOU out there.