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.
j.v. –
Hello all,
i just finished with “Heiny 101”, and wanted to offer some personal feedback on the overall course.
Why did you join the class?
i wanted to learn more about learning to enjoy my body more.
Was it easy to read the class documents?
Yes, it was quite easy to read and follow along with the lectures.
Would you recommend the class to other sissies?
Yes, i would really recommend this course to others, it starts you off at a comfortable pace and eventually builds to a strong finish.
Did you learned something?
Yes, i learned to relax more, and how to focus and prepare myself to really focus on how you can find pleasure when playing with your hiney.
Was the class fun?
The class was fun and the progression of the exercise helped me to comfortably progress to bigger and better things.
Take care,
j.v.
Sasha –
Had to put some of the classes off But I found it really easy to follow. Having a set schedule also made it easier to commit.
Mia –
I liked the course and I think I am ready to use my anus and I know more about my body and how to take care of my pussy
Anira –
It was so good I feel like a proper sissy now able to give it all!
Layla22 –
It turned me into the best Anal slut I can be
Melissa Flirty –
A great course for anal beginners. It introduces newbies it the fun of penetration and coaches them through the skills and techniques needed for safe fun penetration. Gets us sissys in the right mindset to receive lots of lovely cock in the future. ❤️
Alice –
loved this class, documents were easy to read, and the class itself has great build up.
Jessy –
I tried this class because I was interested in Anal but didn’t really know where to start or what to look out for.
I was possitively surprised by how the class starts slowly but then picks up the pace – all in a very managable manner.
It is realy great how you build up to being able to take more through your routine while getting enticing and motivating letters.
If you are interessted in the toppic but never really could get into it this is a good idea.
Julia –
was good for beginners but i would have liked something more!
Daisy Doll –
Very, very good course. Before that, I could hold the plug in myself for no more than 10 minutes. I did it very, very rarely. And now, after completing the course, my hole desires daily filling for many hours 😉
Becky –
As a newer Sissy, I wanted some additional instruction on how to make my transformation, especially in the area of anal. This course provided me just the right amount of push to take me from a complete rookie to a more prepared sissy. Thank you to the Academy for such a great course..
couxl –
A great course for any sissy that wants to learn how to receive anal the right way. this course will get you to the point where you enjoy every minute of it. which if you’re like me and in chastity, learning to enjoy anal is something you’re going to want to do.
Grace –
Great for beginners. Was already experienced, so I didn’t learn much. Wish I had known about this earlier.
Jizele Swallows –
The course fulfilled its promised, now I can have anal pleasure! thanks academy!
Rai97 –
I had been doing some anal previous to this class, but wow. I’m surprised how much more one could enjoy it if done correctly <3
MissMay –
I’ve always wanted to try out playing with my ass pussy but all the material on the web was inconclusive and didn’t really “teach” you how to have fun so I wanted to try out this class. The class itself is easy to understand and guides you through the necessary steps without trouble. I would recommend it to everyone who’s like me and wants to try out something new, so just enjoy it and have fun 🙂
VickyVenus –
The perfect intro for any sissy looking to explore with and within their ass pussy. With the added on butt plug set, I worked my way through the sizes and I am now ready for the real thing. Such a thrilling class! Xx
CamilleSexo –
A wonderful class for sissies interested in training their pussy. Do take note that this is an intro though. You will learn the basis of safe anal pratice and slowly build endurance and desire. At the end of it you will be ready for the real thing 😉
Rachel Starr –
I joined the class to get more comfortable with anal play, I’d been experimenting for a couple years now but always seemed to be uncomfortable when trying full penetration but the class gave loads of helpful tips to get me used to and enjoying the pleasures it can provide, the only thing is I wish the course was a tiny bit longer but then again it is only an intro!
Jenny Griffin –
I loved this class! I was so nervous about bottoming, but now I crave it…I LOVE the pay of the training, and I love being a bottom.
Josie Pink –
Like all the classes here this one is worth every penny. I have always wanted to enjoy anal play but just couldn’t get comfortable with it. That has all changed since this class. My boy pussy now craves it!!! Built to taking a 7 inch thick cock for 30 minutes. Now have mind blowing sissygasms! This was the perfect class for me.
Sissy –
I really enjoyed this class. It’s great as a baseline for exploring anal play. I really enjoyed how it ease you into it. It has helped me enjoy anal play alot more.
Kavontae Foster –
Great course really got me to push my limits ☺️ And pushed me to be more comfortable with my toys
Candy –
I really Enjoyed getting these instructions and my pussy really loved it and wants more.
Violet Riku –
Truly a fantastic course to learn the sensual pleasures of anal plays with many imaginative information that will form a good basis for starters.
Sissy Britney Jane –
I totally loved this course!!!!! The perfect way to pop my anal cherry! I went from an anal virgin to an anal queen and now vigorously enjoy all the delights that my sissy pussy has to offer. Totally recommend this course! ❤️
Jennifer –
An amazing course. It is well thought out and builds you up at a careful pace.
sissycindyrose –
Helped me get over the stigma off anal penetration. Now I practice next to every day!
Sissy Paige –
Really enjoyed the class. I feel like I can take most sizes now without to much trouble and I feel so much more satisfaction from an anal orgasm than one from my clitty
Paulie –
I really enjoyed it but I couldn’t sissygasm from it looking forward to part 2
Brandi Loves –
I really loved the course it was perfect. I got the course I wasn’t able to last long with s toy but afterwards I feel like I can take on the world. Highly recommend it
Brenda O’Lassey –
Amazing amazing course really “opened” me up in the biblical sense 😉
Silvi –
I want to tell that i enjoyed the classes very much.
I felt pleasure from my pussy but didn’t experienced a anal orgasm, but i felt as if it could have append.
I think i need a little more Guidence and information about the right way to do it.
Nevertheless it was a very good class and i will keep trying until i reach my sissygasm
sissyJess –
Slow and steady start that works you up well. My only complaint is that I want to take bad dragons and I don’t have a guide to work my way up to those .
Jamie –
I very much enjoyed the classes. They really helped me get to enjoy anal training.
Naughty Liz –
I recommend this class for everyone, that always wanted to try anal, but couldnt enjoy it or chickened out. The pace and the Tasks are very good.
jennijenzz –
If you don’t know the pleasure you can get from fucking your sissy pussy with a nice realistic dildo I feel sorry for you. I really do. You won’t be a true sissy until you cum from anal. Take this class. You can thank me later. jennijenzz
Erik Proffer –
I really enjoyed the class I learned alot about anal and how much fun it can be
Sissyshanny –
Amazing course with plenty of great engaging content.
manblgxx –
Really enjoyed the class! As a total newbie this helped me on my journey to being an anal slut. Would love a more advanced class!