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.
Bently –
I went into this class not knowing anything about anal pleasure. This class helped me grow and develop a lot, and now I can fut my 8 in dildo. I enjoy anal now so much and cant wait to take real cock.
Tiffany –
The class was very informative and fun. It provided many good ways to ease yourself into anal play.
Samantha –
I highly recommend that any sissy looking to get into anal take this course. I had experimented with anal in the past but always stopped because it was just too uncomfortable. This class guided me through slowly building up and allowed me to (finally!) find my prostate. That discovery helped me to see anal in a whole new way.
My only complaint about this class is that at times it seemed that the next letter came to quickly, not giving me enough time to master the pervious one. However, its easy enough to just not open the next letter until you are ready and to go at your own pace.
Emily –
This and all the classes are incredible, I discover myself as much as I am and as I want to be, after taking this course I feel more myself and I am a new me
Jovan –
It was really fun! I didn’t achieved my sissygasm yet but I hope I would. I would reccommend. Anal Intro inspired me to more explore my butt and I’m glad I did. I would like a better explanation of how to achieve sissygasm.
Éva –
OMG, my pussyboy is Amazing
Catilyn Smith –
Very helpful. Fast paced but I was always excited to see the next email. Would recommend to any new comer.
Jules –
I had a ton of fun with the intro course! It made me want to dive right into the next chapter of training.
Sammy –
It was good. Learned a lot.
Alise –
The course was quite funny and very hot. I used to have some problems with anal (mainly with insertion), but after the course it became somewhat easier. It is even possible that I will continue my studies in the following courses. Nevertheless, this course is great for those who are just at the beginning of the “anal path”.)
anna –
Ok not a beginner here .x.x.
It was a nice 🎁 gift for my pussy .
For sure I recommending this one . It’s a good start for every sissy how like to explore her pussy
Slutty –
Really a nice training, just like all i tried. Had fun and really helped me to enjoy the first penetrations being relaxed.
LEA –
I had acquired two anal dildos that I had not used before,
These courses taught me how to use them.
Your letters were very clear and explicit.
I had to imagine a scenario to accompany the courses: a meeting with a pimp To whom I have endeared myself. I had to work for him to pay off my debts.
Classes were the stages of my training.
Anal dildos have been widely used
With the help of my script, I was really excited about classes.
Thank you very much for that.
I’m thinking of buying the Expert Court.
Negative point : I would have liked =more videos or images.
Lauren –
This course focused and refined my long interest and sporadic activity in anal sex, filling in the blanks that had slowed me or even stopped me sometimes. I have been able to achieve progress/advancement I never thought I’d achieve. I’ve had more fun and enjoyment in the past month using this course than I have had in all the prior years. In fact, I was so sure of it based on the quality of the academy overall, I simultaneously bought the advanced course and it has taken me deeper than I imagined possible, literally and figuratively! And importantly I feel more like a girl than I ever have, and that’s no small achievement because I’ve secretly felt that way since my youth. Thanks!
Ayoon Kang –
The best thing about this class is that developing and arousing my sissy pussy has become part of my routine. I used to prepare my mind and deal with my pussy on special days, but now, thanks to the daily task, I am naturally training my pussy as a part of my daily life, making it a more lewd hole.
Slutforbigcock88 –
It was great overall but I expected more video or audio instructions that would push me to do this sissy anal stuff. Me personally, I would love to see a sissy or beautiful lady doing the buff play because I wanna be just like them. So any sexy video of a girl doing butt play would be good to inspire me to be like her.
Dagarr –
This was incredibly unformational!
It really helped spice up my sex life!
Cindy –
Definitely a beginner course, so if you have any experience skip this one and go straight to the Anal Expert course. I took this one because it was included in the ABC course. The good thing about this course is that it encourages us to make anal a mandatory part of showering not only during the course, but for all future showers going forward. I wish I had skipped this one and gone straight to the expert course as I did not really learn any new information or skills from this course.
This course, like the Free Course, contains multiple dead links which shows that the Academy does not review and update its courses, which is a big disappointment. The links, intended to illustrate salient points, really need to be updates or else completely excluded from the course and replaced with fixed images showing shape and dimensions of plugs, dildos, etc. Apparently the links were placed there as advertisements as the working links show products for sale at sissylover.
Heather –
I had a wonderful time with the course and absolutely plan on moving on to the Anal Expert one! It was a bit of a struggle to find privacy as frequently as needed, but very, very worth it. The best part for me was that in the final exam I finally managed an orgasm from anal alone! Can’t wait to keep practicing!
Tanisha –
I enjoyed the training a lot it was very helpful. After the training I have learned basics and it also helped me with anxiety that comes with anal. I’m a lot more confident to use toys slowly going from small sizes first but I recommend this to anyone who doesn’t know where to start and are riddled with anxiety that comes with anal
Sky –
Great class, was a lot of fun to follow. Helped me get back into anal and really enjoy it this time.
Mia –
It was a very delightful experience and I can wait to explore further. The course helped me develop more confidence in my anal capabilities.
Amber –
This course was amazing! 😍 it inspired me to increase my anal toy collection and taught me some new skills
Aliyah –
I highly recommend this course.
Before I joined the sissy academy I liked anal, but it was always more hassle than it was worth.
I decided to join the beginners course because it offered the opportunity of learning love anal, and it did not disappoint.
I no longer go for the biggest thing I can put in there to stretch, with little to no warm up, I go for things that can fit easily and I concentrate on all the sensations and it has never felt better.
Thank you Sissy Academy for teaching me to LOVE anal!!!
I started the expert course immediately, I can’t wait to begin.
Tiffany –
This course was so much fun. It really awakened my desire for anal. I’d experimented quite a bit with my pussy before but the slow build up has me craving more than ever. I couldn’t help but jump into the expert course right away <3
Ivy –
Solid course. Pacing was great. End result was much more than expected. Wasn’t difficult. Taught more than just insert remove repeat
April –
A fun course that encourages a beginner to progress their capabilities. I appreciated the strong push for safety.
Mia –
Anal is my preferred method of masturbation now! The only part I didn’t like was the suggestion about using soap as lube as this can be painful.
Sybille –
Overall, I was already very satisfied. I take the liberty of making a few small comments.
I build these great sissy challenges into my life and that’s where continuity helps. That is, there is a regularity and a fixed structure.
The extra class anal overlaps again and again with ongoing tasks and demands, keeping track of that is not so easy. Then not all tasks were comprehensible for me, but that could also be due to the fact that I am not a native English speaker.
But that’s a high level of complaining. I had fun, am deflowered and continue with the Anal Expert course.
Nikki Reeves –
This is a very thorough class that really takes you from step one. The instructions are super easy to follow and there is a natural progression to the class. My only complaint would be that the class seems oddly centered around food items.
Jennifer –
I liked taking this class. It gave me an opportunity to bring out my inner sissy and want to pleasure as many as I can with my boy pussy. Thank you for the class and I look forward to taking the next class and become better.
Polly –
I joined this class to try to expand my horizon 😉. The class material was easy to follow and I would recommend it to others hoping to give it a go. I did learn some good techniques and will continue to use the lessons. I think it would have been good to know that there were purchased to be made for the course. Why did you join the class?
Olive –
Joined to train my ass to take my 1.5 in dia 8ins long imitation cock dildo. Due to my family situation it will take me longer to achieve my goal but the course details have given me guide to follow to achieve my goal. Well worth the money thank you xx
Cassie –
The lesson was great, really helpful for easing yourself into anal!
Stephanie Sugar –
This was a very fun and informative class that really helped me. I would recommend anyone who is interested to try it as it really does ease you into anal.
Nadia –
Easy and thoughtful pace. As with all the courses, you really feel the caring and positivity without sacrificing the eroticism.
Tonia –
Good course, fortunately my pussy is healthy and open, especially thanks to the various tips for the care of my pussy. I look forward to taking the anal expert course and hope it helps me reach sissygasm.
Rhiannon –
Until I did this course I was stumbling in the dark when it came to anal play. There were a lot of helpful tips and tricks to get warmed up and spread open enough to enjoy my toys. Some visual aid attached to the assignment would be helpful too, something to put sissies into the mood for their assignments.
Sonia –
An eye opening , and pussy opening intro to anal servitude and pleasure.
It was fun, practical and inspired me to purchase the expert course as well.
Definitely worthwhile investment in my sissyhood.
Rikku –
Good course if a little basic for me at this point I’ve thankfully gone much further and had my pussy used by real men quite a lot. But the caring tips for keeping a healthy boipussy were very good and very informative. I’m looking forward to the anal expert course and hopefully it’ll help me to reach sissygasm.