30 days training
Learn to enjoy anal wholly within 30 days
Anal pleasure
You will be taught to do anal in a sissy way
Slow & gentle
Feel calm and relaxed while entering an exciting sissypussy life
Proper sissy masturbation
You will love anal way more than stroking your clit
SissyLover Academy Boost
The class will give you 10 anal skill credits to be added to your sissy training book
No toys needed!
However, purchasing this class will grant you a discount code to buy your very own first anal toy 😋
- You’ve watched video after video of sissies bouncing on cock, and you’ve always wanted it to be you. But when push comes to shove, something has always stopped you from feeling good about being fucked. Well, this class is going to help you change that.
- Whether you’ve tried putting something inside you before, or are a total anal virgin, this class is here to slowly, gently encourage you past whatever discomfort you have, so that you don’t just like anal play – you love it!
- Our tried and tested schedule has taken hundreds of sissies from a place of discomfort, or disinterest, and turned them into eager anal whores. Don’t believe me? Just read a handful of the reviews on this page.
- You’ll learn to release any shame that you may once have had about anal play – exploring this fetish in a way that is both safe and encouraging. Girl or boy, gay or straight, everybody has an asshole and everybody can learn to love gently fucking themselves to oblivion.
Alexa –
This was fun and really good for someone that is not experienced in anal. Thanks to this I started to learn to enjoy anal without risk to rush things. Now heading toward the expert one.
Linda –
The course was okay. A lot of it felt like repetition and was a bit too easy for me. I viewed myself as anal novice so I thought this was the best course for me. It was not.
I can however see that if you have never done anything anal this course could be useful. I feel tempted to try the anal expert course but I am worried that it will be too hard for me. Maybe an Anal intermediate level course would be great.
In conclusion a great course that was too easy for me.
Natalie –
Super fun course, as they all are on this site, but great intro. Now I can’t wait to start the advanced course
Josie –
Excellent advice on how to strengthen and stretch that favorite sensitive spot! If you need good instructions on how to get your boi puss ready, this is an excellent starter!
Vianna –
The course was fun and I had lots of learning on it, only thought, it was a bit short and not suitable in my routine
Silver –
I thank you all for teaching me and making me the sissy I am ment to be thank you all
Shellybabe –
It was a fun intro and I learnt a lot about myself.
I definitely need more practise and progress onto bigger toys because the course went too fast for me, trying to fit it in with normal life.
I would recommend the course as an intro.
Thanks though.
Octavia Fae –
Great course for beginners and any other sissy that wants to learn more about anal and build better habits. I have continued my shower routines and am looking forward to taking the expert course.
Honey –
I’ve been following the academy for some time and really getting into my studies and I decided to treat myself to some extra courses. Overall I had tonnes of fun, some elements I’d already put into practice since becoming a sissy but I’d deffo recommend it! The only downside I probably have is that I’d wish my lessons would of come quicker!
Johanna –
I loved the course and how it got me to love anal. It had the right speed introducing all the new stuff.
Elise –
Never looked more forward to taking a shower ever before. It gives you everything you need to make sure you’re progressively taking more into your pussy, but also making sure you’re doing it safely and take care of your hole. At the end of the course you’ll have a fun shopping trip~ Looking forward to the expert course
Malvina –
This class is perfect for beginners, i mostly enjoyed it and keep doing it on a daily basis after the class is done.
I can howerver recommend adding some more cleaning instructions for preparations early on, it got kinda uncomfortable at some points.
But all in all a good and fun class i would recommend for all sissies like me.
SissyNinja –
It was very much fun. I think I’m now ready for more anal stuff and let pleasure myself with a strap on. It’s very good to lern the basics and now I’m thinking to make part two.
Rancy –
It was okay overall, but it felt a bit weak. It seems better to increase the intensity by tuning together with advanced.
Patricia –
As a straight man, I Patricia already had experience with plugs and dildos before the course, especially since last year my mistress let me fuck her more often with the machine and a larger dildo, also with depth, diameter and speed, but I wanted to get better and actually I should do the expert course but in order to get off to a good start you should first take the beginners course and I will now deepen some of the exercises and then get the expert course. Dildos of different sizes have already been ordered so that I can practice. Since I now spend more time with my Mistress, I’m really looking forward to her strap on or a nice fisting.
The beginner course made a lot of things more understandable and therefore easier
Best regards
Pati
Emily –
This class was so much fun and really helped me to practice better anal play. I’m now enjoying daily the pleasure of anal play and can’t wait for the next one
Jordan –
This is such a fun class. If you’re new to anal play, this is a good, slow intro. If you were an anal player and need to get back into it properly, this is also a fun time! That was my case, and it was very fun getting my pussy back to work. This offers a lot of solid advice, and the activities you do for the class are easy. I finished the class weeks ago and I’m still doing my daily exercises for fun.
I would recommend this class to others and already have recommended it to a friend!
Remember to use lots of lube, fellow sissies. 💜
I plan to continue my studies with more toys and I want to take more classes from the academy this summer. 🙂
Evelyn –
An excellent course that allowed me to discover more about myself in depth.
Lexi –
This is perfect for beginners. It teaches how to play with my anus step by step without additional purchase. I really enjoyed the course.
Madison –
A great class for any who are even just curious as to whether they might like anal or not. I was not positive how my feelings about it were gonna be but now I’m learning how much I LOVE IT! Totally worth and makes it easy to follow.
Liz –
It makes fun and you become good skills for anal pleasure
Jenna –
I wish he would talk more about stretching and talk more about big dildos.
But i likes the training
Nikki –
I really enjoyed the class.
Once the lectures started they came fairly regularly. The instructions were concise and informative.
It was easy to follow and a pleasurable experience. I plan to sign up for the advanced class soon.
Nikki –
I love the sissy academy. Friendly stay, so many resources they offer to learn from, and very encouraging. I’ve been doing anal since I was a kid and took this coarse in hope of correcting bad habits and to improve my game. Nothing I was taught was worth and I love the community atmosphere these individuals provide. Hopefully they can help me navigate the complexity of my sexuality, gender identity and take back the power and pride of my role as the bitch in bed!!!
Michelle –
I signed up for this course having previously tried to embrace this type of play but due to past poor experiences almost convinced myself it wasn’t for me, how wrong I was.
The course is well structured and helps ease you in to establishing a habit you can stick with and progress while taking it deeper, becoming very comfortable with anal play and having fun practicing new skills.
I can highly recommend this course as it took me from a place of discomfort to
enthusiastic participation.
Erika –
I have loved this course. It really helps to build a habit that sticks with you. And of course learning to slowly stretch my boipussy safely has been super fun! I am so exited to take what I’ve learned in this class and continue to expand on it. I definitely recommend this class to anyone who is new to or looking to try anal.
Jennifer –
Bought this course along with beginners chastity. It’s a lot of fun and really easy you into things if you’re a complete beginner. A lot of low budget options are given as well so if you can’t afford toys then don’t stress!
Lily –
If you have no anal experience this class is for you. if so, choose the expert class. you will be happy.
Sissy_Rachel –
This course has helped me become more comfortable with anal penetration. I would recommend this course to all beginner sissies.
Evangelyn –
Have experience with solo anal play, but wanted to give this a try to better build on the foundations I’ve learned. While focused at beginners, it was definitely still fun and worthwhile, allowing me to pick up some new tips and keep me hungry for more 😉
Alisha –
Befor this Class I tryed Anal now and again. The fealings I got were somethimes realy bad, so I understand I did something wrong.
As of now After the Anal Intro Class, I can say that I am in love with the fealing Anal gives.
danigurl –
This was a very good experience. I learned a lot about my journey into anal and I can honestly say that I crave it now. I had fun, and I did grasp the basic skills needed. One of the side benefits is that I have a clean and exercised pussy now. It feels healthier. I recommend this course for those who like myself wanted to “try” this as something new. I wanted to learn to want anal sex rather than clitty sex, and I believe I can see a path to that objective here. The documents were easy to read and use. The things that I did not like were, the assumption that I could do these exercises with my morning shower. In my personal circumstance I can only do my sissy “stuff” late at night, so I had to adapt there. Also I am a bit leery of putting things inside me that I might not be able to get out like grapes and vegetable items. So I bought a proper butt plug and small dildo for the insertion exercises. I would recommend others to do the same. I would also like to see more instructional emails like on a daily or every other day basis with some hypnosis recommendations. I went out on my own to find some. Going two or three days between instruction at least for me makes me loose my way. I need constant reaffirmations. It was exciting going out and getting the toys and then using them. I am also doing more bulb enemas too. I also finger myself when I do my morning showers, its just I cant do the extended vibrator at that time because of the time available with two people needing to use the bath room, and my sissy adventures have to be on the stealth… If you know what I mean. All in all it was a good course. I’d recommend it and would do it again.
Susan –
Nice instructions to begin with. Encourage you all to practice.
Emma –
It was a super helpful and enjoyable experience. It was definitely worth signing up for. It made me feel like I was finally being myself. I would100 percent recommend this course to others.
Clea –
It feels great to have my sissy pussy well trained. I’m ready for bigger dildo right now
Bambi –
Perfect for sissies who want to learn how to properly train their pussies. The slow progression ensures you’ll learn to love the feeling of your pussy being full and used. The reading material and assignments were easy to understand and follow. Highly recommend
Patricia –
Wannabe the best sissy for my future BBC lover, he doesn’t know it yet !!
The class learning material was easy-to-use. Highly recommend it to other sissies. I learned with the training daily = fun !!
Thank you
Danielle –
I whole heartedly recommend this class! I was struggling with anal sex being uncomfortable and this class gave me the structure to train my pussy! Now not only can I use my sissy pussy, but it feels good! Thank you Sissy Academy!
Princess Lucy Kiss –
Conditioning yourself to feel ultimate pleasure through anal rather than clitty masturbation is a major step towards Sissyhood. Therefore having the right training in Anal, including safety and hygiene, is vitally important. This course is just what you need as you continue your Sissy and Anal exploration. It guides you in the right direction as you get into the right anal habits. Highly recommended.
Lucy –
A great introduction to anal. it goes a bit slow, but thats how it should be, i ended up really enjoying anal because of this course. I looked forward to each letter