Sissy Sorority - Anal guide

This anal guide is designed for sissies who are just started experimenting with anal. For those who do have a lot of experience, do read it because there is a lot of usefull information to be found.
The guide is seperated in weeks. In total this guide will take you 6 weeks to complete. After the 6 weeks you should be a anal sissy pro. If not you can always take things slow and take your time with every step.
So what will you learn in this anal guide?
– Techniques
– What to use
– Different ways
– Sweet spot
– Cleaning
– Anal with others
– Much more

There is a total of 6 different lessons you will complete. After studying your lesson you will do your homework. You have to do your homework for 7 days in a row. After the 7 days, you can move on to the next lesson. It’s very important you do not skip and stick to the 7 days training. This way your brain will get used to the motion and never forget. If you skip parts of the training your brain might just forget it.

An important first lesson is: Repeating is key. Practice as much as possible during the next 6 weeks. And after your training is finished it is super important you maintain your practice.

Week 1 - Finger and preperation

Week 1 – Study:

For this first week, we will start from the absolute beginning. To start off this week you are going to use only one finger to explore your body with. The ass is a vulnerable part of the body and by experimenting in this training you should always be careful. A few things to keep in mind are: Pain, damage and preparing for anal

So the first topic we will talk about is how to prepare for anal. In a later study, we will go over the fact of how to prepare for anal with someone else.

So for the first week, we are just going to use our fingers and some lube, but an important thing to keep in mind in advance is that you always think about what you will need this session. Because if you don’t there is a big possibility you have to run to the bathroom to grab your dildo while you are playing and nobody wants that. So always make sure you have everything you need within range.

Another thing you have to know in advance if you already experimented before you should know this. The first few times you start with anal it will hurt. And not just a bit. Even if you will just use one finger, it will hurt. So always keep that in mind, especially in the beginning.

The last study we will talk about before you can start doing your homework is damage inside your anus. This is an unfortunate moment that can happen to all of us, there is a possibility you might get an irritation, open wound or even worse. Now, this doesn’t happen that often. But before starting your homework I have to give a disclaimer: Don’t use any sharp or breakable objects while doing anal. It’s extremely dangerous and can give a whole lot of problems for a long time.

Week 1 – Homework

Now it’s finally time for your homework for the first week. So like said before in the first week we are just going to start off with the fingers and if you want I recommend using some lube. So ideally you will repeat this every day for at least half an hour. If you have the time and endurance just go for a longer period of time. It is understandable you can’t keep going for half an hour for the first week, so if you can’t just stop for a moment and try again after a few minutes. Ones you get used to the pain it will go easier.

So we are just going to start off slow, so lay down on your back and just start fingering your ass. Don’t forget to use lube if this is your first time. Just gently push in your finger. If it hurts that means you’re making progress. Now slowly push your finger in all the way.

Now that you are in it is time to take it back out again. So ever so slowly start taking your finger out of your ass again. This might feel a bit funny and even familiar. Its almost the same feeling as when you have to use the bathroom just a bit different. Now that you’re out again its time to repeat this process over and over. Keep doing this for the recommended time of 30 minutes. 

If it hurts too much to take it out every time. Just try to leave the tip inside and then start pushing again. This way your anus doesn’t completely close so it hurts a bit less. If you don’t feel any pain what so ever, thats good! Just keep on doing what you are doing.

This is your training for the first week. I want you to repeat this every day for 30 minutes straight. And next week we will see if you can manage more fingers at ones. But for now, this is your homework for the first week.

Week 2 - More fingers and shaving

Week 2 – Study:

As you might know, it is important sissies have shaven legs 24/7, thats not a question but a requirement. But this rule doesn’t apply to the legs only. Your private area should be just as much shaven at all times. Every time you want to continue your anal training, it is super important your anus and ass are shaven at all times. Body hair is manly and the exact opposite of your goals.

When you shave you’re not just going to use your standard razor. No, you will get a fresh pair of lady razors at your local drugstore. Did I tell you it is only allowed to get the razors in person? Don’t just order them online and be done with it. No, just go out to the drugstore and get over your fears.

Now its time to talk about your anal training again. If your ass still hurts after the first week, you might want to slow it down a little. If you’re not experiencing any problems so far you can just keep going. This week we will take it to the next level. Now that you’re used to the feeling it is to start introducing more fingers.

Week 2 – Homework

So like said before it is time to introduce more fingers to the play. Now that you explored your first times with anal and stretched it all out a little. The next step, of course, would be to make it a bit more challenging and more tight.

So as a start, you are going to grab everything you will need, which is nothing more than your lube. Now just start off again with just one finger again. This is just to get it all open again. You will notice when you get more experienced you need to spend some time opening up your hole again. Of course the more you do this, the faster it will go.

Now that your first finger is in and you are used to the feeling again, let’s see if you can fit in a second finger. This might be a bit tricky at first but if you stretched enough in your first week this shouldn’t be a problem. You will keep doing this for 30 minutes every day, just like normal. But at the end of the week, you have to be able to use 3 fingers at the same time.

If you can’t get 3 fingers in at the end of the week, just take things a bit more slow and try a little longer. Continue to week 3 when you are ready for it. Not because the guide tells you to.

Week 3 - Eating and dildo

Week 3 – Study:

As you have been playing around for the last 2 weeks it might have caught your attention that not everything is as clean inside like you want it to be. This is because your eating pattern is very important when you do a lot of anal. Mainly because your body needs a few hours to go from eating to the end of your intestines.

The big problem here is that the time in between is different for everyone. You can find out how long it takes for you by trial and error. There is not really a better way to find out then just to try over and over again. For most people, this time is about 15 hours. So if you do a lot of anal in the evening. Make sure you do not eat too much before lunch.

It’s not just when you eat, but also what you eat. Eating fast food will go through your body within like 3 maybe 4 hours. While a healthy salad takes way longer. Make sure to keep this in mind when you want to do anal. Of course, when you play by yourself it isn’t as bad as when you play with someone else. But it’s always best for your hygiene to prepare for it no matter what.

In a later study, we will also go over everything you have to keep in mind and prepare for when you do anal with someone else. But for now, we just keep it to you playing with yourself.

Week 3 – Homework

Now that you are more educated about the eating patterns, it is time to put it to good use. So this week you will have to invest extra much time in finding out when you can and when you can not eat. Of course, a week is not even near enough time to find everything out. So even after this week, you will have to continue doing this for a long period of time.

Just keep a little scheme about what you are eating, when you are eating and just as important how much you eat. A little tip is the more healthy you eat the better it is for not just your body but also your intestines.

Also, it is time to introduce a new toy this week. You have played with your fingers for long enough. It is time to get something bigger. So for this week, you will be using a dildo for the first time. If you already have experience that’s great.

There are more than enough dildos in various sizes. If you have a bit more experience you can just start out with a bigger dildo, if you haven’t there are a lot of starting kits on the market. These are perfect because you will receive a few different sizes. You can start with the smallest one and work your way up.

Just like normal you will be penetrating your ass 30 minutes every day, but now you will be using a dildo instead of your fingers. At the end of the week, it is expected you can at least take in 4 inches and a width of about 1 inch. If you’re not able to take that much for half an hour straight you might want to take a bit more time then just a week. You can just continue when you are all caught up.

Week 4 - More and more toys

Week 4 – Study:

Going into week 4 you already learned a lot about anal. But we’re not done yet. This week you will get more familiar with different types of anal. Of course, your fingers and dildos aren’t the only toys you can use to please yourself. So today we will be going over a few different alternatives for you to use.

So the first item would, of course, be a buttplug, Buttplugs are used for anal when you want to extend into a longer period of time. You can just insert the buttplug, get dressed and go on with your day. You will have an amazing feeling in your ass while no one else around you knows about it. In this weeks homework, we will also be using a buttplug.

Next to the standard buttplug, there are also lockable plugs, these can be used for anal and give the control to someone else. Definitely a fun game to try out sometimes with a partner you trust. The electro plug is another variant, and like the name says it can be used to give you a little electric shock when you’re playing. This is not for everyone but is a fun toy to experiment with sometimes.

Now next to the dildos, plugs, and fingers there is a last little thing we didn’t talk about. We did talk about a few fingers but not about fisting. Most people will know that this just means sticking your whole fist into your anus. Now, this isn’t as easy as it sounds. You will need to practice a lot before you will be able to get your whole fist in there. But ones you can, it is a magnificent milestone. Also, fisting is a lot easier with someone else. Fisting by yourself just isn’t a comfortable position. When someone else does it they can get right in front of your ass and give a lot more pressure.

Week 4 – Homework

Now that you know a lot more about toys it is time to move on to your homework. Of course, we didn’t go over every toy, there is still a lot more like for example the anal beats. But the main toys all did get their moment of fame. So for this week, we will get more into the buttplugs.

The buttplug is a beautiful product. It comes in many different sizes and variants. And because the buttplug market is so flexable there is something for everyone (who is into anal of course). So you will have to find out for yourself what fits you best and stick to that product.

Now what you will be doing for this week is a bit more intensive than previous weeks. You will remain penetrating your ass for at least 30 minutes a day. You can do this with your fingers or choose to use a dildo. But after you are done you have to get your buttplug and penetrate your ass with the buttplug. I suggest you leave the plug inside your ass for about 2 to 3 hours every day. If you want to go longer you are more then welcome.

Now there is a little disclaimer with this homework. A lot of people always say it is dangerous to leave in a buttplug for a few hours straight. But with a lot of experience, I can tell you nothing bad ever happened. But if you think it is not healthy to leave in the plug for this long then just don’t do it.

Week 5 - Anal with a man

Week 5 – Study:

Anal with a man, this topic has been shoved to the end more and more. Mainly because it is a whole lot harder to have anal sex with someone else then it is to have with yourself. There is so much more to keep in mind, so in this study, we will be going over everything there is to know when you have sex with a man for the first time.

Just keeping all the extras aside of course what makes this super hard is the fact that you will be having sex with a man for the first time. You will have to put your mind to it to actually do this and not have any regrets afterward. Sometimes it’s good to think about an action before you actually do it. Just ask yourself if this truly what you want. Because if not it is a good reason to wait or just cancel completely. 

Now I know you sissies and you all dream about this so let’s just go on with the next step. When you have sex with a man a few things should always come to mind. Safety, hygiene, and trust. These 3 topics should be taken care of at all times, because if they haven’t you put yourself and your partner in danger.

So let’s start off with safety. Now that you are the one in the more vulnerable possition it is always extremely important you take good care of safe sex. Both parties should always be tested for HIV or you should let him wear a condom. This is so important and so easy to just neglect. DO IT!

Now the second part of sex with a man is hygiene, when you play by yourself it’s fine when a small thing goes wrong. But when you’re with another man this is a whole new story. Don’t forget our previous study about eating. This will take you far but you’re not there yet. Just before you will have sex its smart to flush your ass from the inside. Just go to the bathroom for a moment and prepare yourself.

There are 2 options to clean your ass from the inside. The first would be to use an anal shower. Of course, not everyone has this and for them, there is a second option. You can also use an enema. Just look it up on google. You can use these to spray water in your ass and clean yourself from the inside out. A good way to measure if you are actually clean is to have at least 3 sprays of clear water coming out of your ass.

Yes, yes, yes this study is long I know, there is just one more thing we have to discuss before you are ready for your first time anal with a man. The last topic is trust. I know, so cheesy. But don’t underestimate trust. You and your partner will be extremely intimate, and if someone takes advantage of you when you’re so volnerable you will have such a bad experience. And a bad experience is the last thing we want. We want you to have fun with your partners, and not be scared away from ever doing anal again because of one man. So big tip: If you don’t trust him, don’t have sex with him!

Week 5 – Homework

Now that was a long study. I hope you have taken everything in and maybe put it to use with another man in the near future.

Now for your homework this week. It would be a whole lot if you can manage to have sex with a man for the first time this week. It’s understandable this isn’t possible for everyone so if you can’t it’s no problem.

Next to having sex with someone you can also keep doing what you did last month. A lot of penetrating with your dildo and stretching with your buttplug afterward. You can keep doing this for the rest of the week and maybe even get a bit more creative. Use different sizes, different toys and maybe different techniques.

Find your sweet spot, everyone has one and ones you find it I’m sure anal will become even better for you. You are halfway your course right now. Just keep going for a little while longer.

Week 6 - Anal stimulation

Week 6 – Study:

Week 6 is going to be the last study. After this you have learned about everything there is to know about anal. After this week you will still get homework for the next 4 months but the study ends after this part.

So the last study will be one of the most fun ones so far. It is something every sissy dreams about but not many sissies are actually capable of doing it. I am talking about cumming just by anal stimulation. Not a moment of hand and penis contact. Just your toys and your anus that will make you cum. But how?

The hard truth is that you just have to practice a lot. This isn’t something you just do the first time. But there are a few tips to share which might help you get there faster.

So the first thing is your sweet spot, you have been asked last week to find your sweet spot. This wasn’t just without a reason. Stimulating your sweet spot makes you horny and turned on. This is different for everyone. There even is a possibility you can only hit your sweet spot with just a few toys.

Another tip is mindset if you focus your mind on all that stimulation that anal penetration brings you it will make it a whole lot easier to actually cum without touching yourself. Finding the right mindset isn’t easy either but you will just have to try it out.

Week 6 – Homework

So this is probably going to be the hardest objective to complete for most sissies. But it’s also one of the most fun ones. When you have this technique under control you will find out there isn’t a better sensation in the world.

You probably know what you will have to master this week. You will cum without touching yourself. You are not just going to try, but you will master it at the end of the week. And if you can’t just take more time to do so. It is a feeling every sissy has to feel at least ones in her life.

Keep the tips from the last study in mind while achieving this goal and you will succeed. You can continue to the next homework ones you mastered it. Like said before the studies end here. From now on it will be homework only. Congratulations sissy, you now know everything there is to know about anal. The only thing you have to do now is to get full control. The only way to do so is by keep practising.

This Post Has 14 Comments

  1. Adrian Dunbar

    I would love to try anal now

    1. Sissy A

      Any tips for fisting? I would like to try it myself but i cant put more than 3 fingers inside.

      1. Mallory

        I have gotten 5 in but never past my knuckles. But I can fit something that is wider than my fist in my butt. It’s hard to fist yourself

  2. Jo

    Heya love the work you done so far !!!! Keep it up <3 xx

  3. New girl

    How do I lose weight quickly to get a slim passable body? Most important.

    1. Amelia


  4. Sissy A

    I want to do fisting myself but i cant put more than 3 fingers inside. Any tips?

  5. Joe

    if you want to try real dock you could always try to get violated frim a gang bang

  6. Maxine Monroe
    Maxine Monroe

    It’s Day 1 of my Anal Training. So look forward this journey

  7. Gogo Mendez
    Gogo Mendez

    Well, I managed a week. It wasn’t difficult either, I’m already a bit stretched. While reading the other posts here, I noticed that most people announce their success here after the entire anal training. Most people worry that after the 3 fingers, the fist thing starts and they can’t get their fist in accordingly. I’ll make it easy for myself, I’ll use my plug in the form of one hand. That seems to me to be the easiest. That may take a while for me. I will start with Lexion 2 soon. P.S. Message created with Google Translate.

    1. Gogo Mendez
      Gogo Mendez

      Hello everyone, week two is over. everything works like clockwork. When I’ve finished week three I’ll report back here. P.S. Message created with Google Translate.

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