Sissyrulez Small Steps for Aspiring Sissies: Part 3 – Anal Training Part 1

Hello once again to all of my sissy followers! Today I’ll be discussing the next step in my series of small steps for aspiring sissies. I hope you all read my first two posts about panties and cum, and hopefully you’re all wearing panties and eating cum every day!

Today we’re doing some anal training! Yay! Are you all ready to stick things in your ass? Don’t worry, we’ll go slow. For this step you’ll need a traditional vibrator, I say traditional because I don’t want you getting anything to crazy, it’s important that you start off slow, that’s why it’s called anal training, we need to train your boi pussy so it’ll one day be able to take big cocks. Second you’ll need a small butt plug, yes small, once again we need to train your boi pussy. Now since this is only part one, you’ll only need a small butt plug; however, some of you may want to get what they call an anal training kit. Usually they come with three butt plugs of different sizes. This may be good to get because eventually when I do part 2 you’ll need to have bigger plugs. If you can’t afford them though, just get one for now. Finally, and most importantly, Lube. Get Lube! Oh my god is it important. I don’t know how many times I’ve heard of new sissies going out to meet a guy for the first time, and then coming home with a bleeding boi pussy because they didn’t train their ass and they didn’t use any lube. Now if you don’t have money to spend on these things, you’ll have to improvise with stuff around your house. If you’re a broke college sissy like me, try saving up little by little.

One more thing you’ll want to get is a way of cleaning the inside of your boi pussy. Yep, that’s right I’m talking about enemas. Now you all won’t need to buy some crazy expensive machine. In fact some of you may not even want to use one at all in the beginning, however eventually I would recommend you use something if you are frequently putting things in your butt, and you want to be clean from inside out. I recommend just getting a simple silicone enema bulb. You can get one on amazon for like 7 bucks (I’m sure it will come with instructions). I’m not going to talk about enemas for the rest of the lesson, but I wanted to mention them briefly.

Now for the fun part! Now some of you may already have started playing around with putting things in your boi pussy. For those of you who haven’t, here’s what I want you to do: Next time you play with your clitty (I’m sure some of you are still jerking, don’t worry, you’ll be rubbing soon) with the other hand just slip in a finger and start fingering yourself. Before you put it in remember to rub some lube on your finger and massage it around and into your asshole. ALWAYS USE LUBE! Never forget to use lube, you’re going to need it especially with the initial training. Once you start to get looser move to two fingers, and then three. Keep doing this as you play with your finger until you can consistently get 3 fingers in. Now some of you will want to go to four fingers, which you can, but don’t force it. We need to train your ass slowly so it gets used to taking bigger things. It won’t want to take your whole hand right away! So once you can get 3 fingers in consistently, I want you to start making yourself cum with three fingers in your boi pussy. If you’re still jerking that’s fine, this lesson is about training your ass, we’ll talk about training your clitty another day ;) Also if you’re already eating your own cum I want you to eat the cum when you cum this way as well, if you’re not there yet no big deal, like I said, this lesson is about your boi pussy.

So once you’ve cum with your fingers up your ass 10 times(Space them out, please don’t do this all in one day!) I want you to get your vibrator. That’s right sissy, you’re moving on to real toys, Yay! Now with the vibrator I want you to do what you did before, fuck your ass with the vibrator while you play with your clitty( and of course use lube). Remember to go slowly at first, I can’t stress the importance of this enough. So use the vibrator while playing with your clitty until you cum, and just like before do this ten times, remember to space these sessions out! Now after you cum I want you to get your butt plug and stuck it in your boi pussy while it’s nice and loose. I want you to leave it in as long as you can, and please please please remember to use lube. If at any time you feel strong discomfort, please take the plug out for safety reasons. Mild discomfort is to be expected since you‘re not use to having things in your ass. At first you’ll probably only going to be able to keep it in for at most 30 minutes. Eventually as you’re boi pussy adjusts you’ll be able to keep it in for hours at a time. For safety reasons I wouldn’t recommend keeping it in for longer than 3 hours. Sometimes I’ve worn one all day and been fine, but I wouldn’t recommend you do that.

So for this next part I want you to fuck yourself with your vibrator, without touching your clitty at first. Start a five minute timer and then begin to fuck your ass, once the timer goes off you can start touching your clitty until you cum. Once you do this 10 times I want you to set the timer for 10 minutes, and then 15, and so on, doing each 10 times. The goal of this is to be able to make yourself cum without touching your clitty. Once you’re able to cum in this way, I want you to keep trying this until you can come by only anal stimulation consistently. Remember to use lube and put your plug in after you’ve cum.

So keep working your boi pussy until you can cum solely by anal stimulation. Remember to use lube and your plug. This is essentially it for Anal Training Part 1, for those of you who can’t wait to put more things in your ass, I’m sorry you’ll have to wait for part 2. Unfortunately for you my next lesson will not be Anal Training part 2; next lesson will be on shrinking your useless small cock into an appropriately sized tiny clitty! Remember to be safe with your anal training and take it slow! I wish you all the best of luck, stay tuned for my next lesson Sissies!