Anal Stretching Routines
 

You are to wear your biggest buttplug (that fits) in your ass at least 6 hours 4 days a week for a month. In addition, you are to fuck your ass for 15 minutes with your 15 cm dildo to loosen you up and then grab your 20 cm dildo and use your ass for 30 minutes. After this hot little session grab your inflatable butt plug, insert it and inflate it as much as you can and hold it for 30 minutes. Do this 5 days a week.

From what I read on your blog you dislike uninspired dares. You also dislike to submit and please strangers, so my dare is about pleasing you. Out of sheer selflessness, of course :D

First of all you should open your toybox and look what you have. Grab your steel plug, 5.1cm butt plug, numbing lube and your huge purple plug. You'll also need your whore paddle. The steel plug shouldn't be much of a problem for your trained asshole, so just put it right in. Carry the toys to the bathroom and lay them beside the bathtub.

Start filling the tub with water and use some girly bathing solution. Something with unicorns or fairies this kind of stuff. The most annoying thing taking a bath is to wait unit the tub is full, isn't it? You should make your waiting time a bit more pleasurable. Go on all fours on the bathroom carpet and spank your ass with the paddle. I don't give you a number of spanks, but as long as the water is running your will continue spanking your ass.

With your ass red and warm put the black plug on the rim of the tub. Lube it with heaps of numbing lube and sit down on it. One leg in the water the other leg outside the tub. You probably just want to slip in the water and relax but you are not allowed to, until your ass swallowed the plug to its base. When it slips in, let yourself slip in the water. Relax and enjoy how full your ass feels. Rub your clit under water while you rhythmically clench down on the plug. Feels amazing right? But you know very well that you are not allowed to go over the edge.

Time for a bigger challenge. Get your ass out of the water and pull the plug out. But do it very slowly and try to prevent that your shpincter clenches. Your asshole should gape open, a stretched out hole, that can be fucked any time. Use a lots of lube again, maybe you can even get someting in your ass, when you stay open like that. Grab your purple monster plug and push it against your already stretched asshole. Push until it hurts than stop and release the pressure a bit, when the pain is completely gone start to push again. Do this a few times. Hold the plug in with your hand and slip in the water again. The base of the plug should rest on the tubs floor. Let your body weight push the plug deeper.

I want you to imagine a very sexy girl sharing the tub with you. Close your eyes and feel her soft skin on yours. She is kissing you passionatly and pushes you down on the plug. There is pain of course, but all you can think of is this breathtaking girl and her soft lips. You are whispering in her ear to push you down without mercy. Continue to fantasize about her while you touch your needy pussy.

Finish your bath, but never let the plug go from your asshole. Try to dry yourself without letting it out. Go back to the bathroom carpet and pull the plug slowly from your ass. Take a pic of your gaping hole.

You requested a routine, since this bath was such a nice experience, this is how you'll spend every bath you take.

Omg thank you! This is wonderful! It's the first time I'll have a bathtub in my life so I'm definitely gonna be doing this!

For those wondering... She is real, a true anal slut, and very easy on the eyes.

Here's a quick morning routine for you. When you first wake up, before you pee, do this.
Lay out your plugs in a row. Number them in your head from left to right. Roll a die or use something like @roll to roll the number of plugs. You will try to work the winning plug into your ass for the next 15 minutes. If you succeed, it stays in until after your morning routine. If you fail, you must swap your ass with the slut paddle a number of times equal to the roll result.

Thank you all! I'd love some more ❤️

I am in my new apartment! Please give me some anal rules :D

Ok now that u are in your new apartment, u will christen each room, u will pick an object from each room and stuff it up your ass and fuck it for 10mins.

While rather uninspiring, pens are a good easy way of measuring progress. Choose a day, say a Sunday, and insert as many pens as you can. After training all week, insert as many as you can on the next Sunday.

If it is more, then you have a clear visualisation of progress. Repeat this over the course of the year.

How about this: whenever you want to cum, you have to have something in your ass.
Get an average of how many orgasms you had per week in the last months.

If it's <10 per week:
You get one "free choice" orgasm per week (so you can put whatever you want in your ass for it), for any additional ones you have to sit on your purple plug for some time: 10 minutes for every orgasm you've already had this week.

If it's >10 per week:
Same as above, but you get to start with three "free choice" orgasms. For any additional orgasm, you'll have to either follow the rules above except add 5 minutes per orgasm, or fuck your ass with a dildo while edging once for every orgasm you've already had this week before you're allowed to cum.

Bonus rules:
For every tongue or dick/strap on (worn by another person) you've had in your ass any given week, you'll get one free orgasm next week.
While having sex with someone, you're free to cum if your ass is filled by something, but this Orgasm will count as five for your masturbation counters.

At the end of every week, track the amount of orgasms you had in a blog post, and if you wanted to cum more but couldn't

Have fun ;)

Sadly I can't do this because I am owned and in constant orgasm denial!

That's a bit sad for my dare but makes the rest of this thread even better 😁

Wow Max1328 that is a hell of a dare, I'll try to get inspiration from it. The obvious best implement for some good anal stretching is the inflatable plug but you don't list what it's smallest size is so I don't know how possible it is to wear for an extended period of time. Assuming that the inflatable plug is, at its smallest, in the 4.1 to 5.1cm range hopefully the following dare works for you. If not, you can substitute the inflatable plug for a selection of your other plugs as you see fit. I've found a similar looking inflatable plug and it's minimum diameter is 3.1cm, so there is some research to my assumption.

Cleaning is an important part of having an apartment, doing dishes, vacuuming, putting away clothes, or washing used anal toys. A few times a week, you are going to pretend that you are a cute little maid cleaning your master's house. If possible, dress up like a slutty French maid or as close to it as you can. Of course as a slutty maid, one of the most important parts of your uniform is your plug. After getting your maid uniform on, you will insert your inflatable plug, give yourself a good spank on each of your ass cheeks to get them rosy, and pinch your nipples to try making them more prominent. You will then start cleaning with the pump from the inflatable plug hanging from you like a proper anal whore's tail. As you clean, you will routinely inflate the plug whenever your mind wanders away from your duties as a maid. When you inflate the plug you will imagine that it's your Sir squeezing the pump. He has been sitting nearby, working while you clean and has noticed you're slacking. Walking up to you, he squeezes the pump, he knows the only way to get a buttslut's attention is through her ass. Of course Sir also likes to pump the plug up sometimes just for the fun of it, as he walks through the room, the sight of the pump dangling from your ass is just too good an opportunity to pass up.

You will clean until your Master's house is clean. If you reach your limit you will keep track of all the pumps that you would have done but didn't, the next time you clean you will start by adding those pumps back in. If you cannot train yourself to either keep better attention or, more likely, to take more pumps, you will accumulate a backlog of pumps. This will result in you spending the entirety of your cleaning task at maximum inflation which will surely speed up training.

Let me know if any modifications need to be made. I hope you enjoy the dare and that it serves it's purpose. As a side note, if you would like a task that involves cleaning out your ass with an enema, let me know. Enema's are a kink of mine, but you said you hate them, but then also don't list them in your dislikes or limits so I have no idea if they are fair game. I assume that you only use them for cleaning yourself before anal but you do include it in your toy list so I don't know. Maybe you do them frequently regardless and would like to find a way to make them at least a little more fun? Let me know.

This one seems wonderful! I will have to give it a try, I hope the butt plug will be staying in because the base isn't big enough, so it keep slipping out when it is pumped! I will let you know if it is possible to wear it while I'm standing :)

I have done only 3 enemas in my life and I really really hated it! I wouldn't say it's a limit but a heavy dislike for sure that I don't want to be doing haha

If the plug won't stay in on its own, I would suggest trying out a rope tie. Maybe something like this? You can skip the knot in step 8 if you need and then add a step 9.5 where you run the two pieces of rope on either side of the inflatable plug's hose.

If you ever decide you want to take more enemas, for example you want to start depth training, It would be my pleasure to work with you to find ways to make them more enjoyable.

Do you have any particular parts of your routine that you want 'spiced up'?