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Home / Training
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Anal Expert

Anal Expert

Rated 4.79 out of 5 based on 1003 customer ratings
(1004 customer reviews)

$25.00

  • Two whole months of anal training!
  • Relocate your pleasure into your sissy pussy!
  • Learn how to achieve a sissygasm!

Not ready for expert level yet? Click here to join our anal for beginners class

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Deeper Longer Faster Harder Bigger
Get ready for the most in-depth* anal training course on the internet.

Do you like anal but want to love it? Are you comfortable with the basics and want to go deeper? Do you want to finally cum like a real girl?

We can’t promise you’ll be able to walk straight for a while after you’ve finished this course but we don’t think you’ll mind that too much!

Learn from a true expert

Join Sissy Ellie, the Academy’s Number 1 Buttslut, for a course that will push your limits and leave you capable of handling almost anything. Ellie has personally tested every tip and technique she’s teaching you, and she’ll make sure that you’re keeping yourself safe every step of the way.

Hard work, big reward.

You’re going to take bigger, thicker toys, deeper than you ever have before. You’re going to learn to ride them harder and faster, for longer and longer. You’re going to completely ignore your clit, sissy. It’s going to be a workout  – and you’re going to take it seriously. But your efforts will be well rewarded!

Cum like a girl

You’ll end this course knowing how to make yourself sissygasm… how to squirt out an orgasm from anal stimulation alone. You’ll find your sissy g-spot and learn what works for you, all while feeling pleasure ripple through your body.

Note: The sissygasm section of the course is easier to work through if you have a variety of toys in different shapes and sizes.

Goodbye to “manhood”

Until finally, at the mercy of your favorite dildo, you’ll push yourself over the edge and wave goodbye to your “manhood” as your knees give way and you squirt like a slut with no self control.

Join Anal expert class

See you on the other side, sissy 💋

Head Mistress Alyssa

1004 reviews for Anal Expert

  1. Rated 5 out of 5

    Bambi – January 28, 2022

    Yes, I acheived sissygasm, thank you!

  2. Rated 5 out of 5

    Filippa – January 28, 2022

    I loved the course and it helped me on my journey to become even more of a sissy slut. I did not achieve a sissygasm but i’m sure i will with my newfound skills and enthusiasm. I now dream of letting an alpha male have his way with this little slut.

  3. Rated 5 out of 5

    Jane – January 27, 2022

    Had a great time with the course to really boost my endurance while fucking myself. It was a bit slow at first but really sped up after during the middle section. I think it should be a bit more clear when to start abstaining at the start but loved doing it the sets. Managed to sissygasm early on with a plug and later with my slepnir when we moved to dildos. Would highly recommend!

  4. Rated 5 out of 5

    Melody – January 27, 2022

    Great, it was easy to flow. Wish there were more assignments with pictures or videos explaining the lesson.

  5. Rated 5 out of 5

    Honey – January 27, 2022

    I like this class because it helped me to push my limits. Also having somebody explain this to me helped me out alot!

  6. Rated 5 out of 5

    Jenna – January 27, 2022

    I’ve always loved anal even before becoming a sissy, i saw this course and thought this is perfect for me because I’ve always wanted to improve. Definitely worth

  7. Rated 5 out of 5

    Amelia – January 27, 2022

    Fantastic! Would recommend it for anyone advancing their studies. Learnt a lot about my body and ended up in multiple hot sweaty messes. 10/10!

  8. Rated 5 out of 5

    vanessa – January 27, 2022

    I totally loved it. I learned so much information that I cannot get anywhere and it’s done in a gentle step by step manner that I was able to achieve my full potential.

  9. Rated 5 out of 5

    Kylie – January 27, 2022

    It has helped me so much on taking on larger cocks. And a sissygasm has been much enjoyable.

  10. Rated 5 out of 5

    Natalie – January 27, 2022

    Just the thought of getting the next lecture was really helpful to get into the right head space to pound my ass and love it. It really helped me connect with my body and figure out what I like and what makes me feel good, really good. Now I have a strapon on the way so my girlfriend and join in on the fun x

  11. Rated 5 out of 5

    Petra – January 27, 2022

    Great step up from the first course. If you love anal you’ll love this.

  12. Rated 4 out of 5

    Ellie – January 27, 2022

    a slow start but iv learned a lot from this course and it has been very fun so far

  13. Rated 5 out of 5

    Bella – January 27, 2022

    This class was very fun and intense. I would definitely recommend this course.

  14. Rated 4 out of 5

    Krissy – January 27, 2022

    Great course, I could learn some new things. Could be shorter at the start, b/c I guess most ppl interested in this course know their butt from the start on.

  15. Rated 5 out of 5

    Jennifer – January 26, 2022

    I loved this course. I am able to take a 10 inch dildo deep in my ass and it feels amazing. Haven’t achieved a sissygasm yet but it has been awesome taking it in my ass. it was difficult at first but once i got more and more practice in it was easy to get the dildo to slide in and out. 100% recommend to other sissies to try this course!!

  16. Rated 5 out of 5

    Sissy Sarah – January 26, 2022

    Very interesting training that will make me become a real anal slut. It’s amazing the new abilities acquired. I recommend this training.

  17. Rated 5 out of 5

    Trisha – January 26, 2022

    Let me start by saying Oh. My. Goodness.! I’m not a beginner by no means and this class knew exactly how to go about the training. I wasn’t able to have a sissygasm until the second to last day and OMG was I in lust. It had my legs shaking and I couldn’t even walk to the shower. Chastity really helps those urges when you’re in the heat of the moment and helped me to focus on my true purpose. It became a nuisance seeing it flop around and half the time I wish it wasn’t even there. Highly reccomend this class to all sissies who want a mind blowing experience. It will leave you a hot mess never wanting it to end!!!

  18. Rated 5 out of 5

    Jade Gemini – January 26, 2022

    I’ve had such a good time during this course, Ellie has been great with interesting tasks and insightful advice. Thank you so much I hope to see an extended anal course someday ♥️

  19. Rated 5 out of 5

    Krissy – January 26, 2022

    The course was a lot of fun. One thing that had me hooked (for some reason) was the long reads during the assignment letters. Along with that, the constant anal play, sissygasms, and feeling girly, it was a great time.

  20. Rated 5 out of 5

    Tian – January 26, 2022

    I have fun and improve your anal skills.I recommend the course to other sissies.

  21. Rated 5 out of 5

    zoe – January 26, 2022

    This course was great, it really improved my anal skills. After this course now I look forward to when I get home so I can play with my toys again

  22. Rated 4 out of 5

    Dawn – January 26, 2022

    I enjoyed the experience overall, it was slow at times & i felt more content was definitely needed, but im still happy to have taken the class

  23. Rated 4 out of 5

    Ashley – January 26, 2022

    It was a very fun course. Unfortunately fell behind but had the best time catching up!

  24. Rated 5 out of 5

    Theresa – January 26, 2022

    Thanks to you I took a real pleasure by the ass, I even had my first sissygasm, without the hands, thanks to you I become more and more a slut, a huge thank you

  25. Rated 5 out of 5

    [email protected] – January 6, 2021

    Could someone get me what’s in my wishlist I would suck the biggest cock for it if someone did

  26. Rated 5 out of 5

    Amanda Stone – October 14, 2020

    This class might be the thing that pushes me to go anal only. I have started linking anal to pleasure and want to fully commit to 24/7 chastity and anal.
    You might not be able to turn back after this my sissy sisters, but it is 100% worth it!

  27. Rated 4 out of 5

    Aurore – October 1, 2020

    Class was fun to learn, and improve my anal skills. I really learn to enjoy my own pleasure "clitless". If you want to improve your anal dexterity and pleasure, do not hesitate 😉
    (excuse my English)

  28. Rated 5 out of 5

    Kendall – October 1, 2020

    Truly fantastic… I never thought I would achieve a sissygasm this quickly given my lackluster progress before this class, but I did! There is definitely no going back now!

  29. Rated 4 out of 5

    Mia – October 1, 2020

    Fun to follow along the instructions.

    Documents are easy to read.

    I would recommend, especially when still learning about anal.

    The male voice in the hypnos wasn't really for me.

  30. Rated 5 out of 5

    Christine – October 1, 2020

    This was such a great experience. I think every sissy should take this course.

  31. Rated 5 out of 5

    Summer – October 1, 2020

    Such a great course walked me step by step in how to use my hole properly and finally achieve that true sissygasm
    Opened my mind and my hole to new adventures

  32. Rated 4 out of 5

    Paulie – October 1, 2020

    Would recommend this for learning to sissygasom. Really good documents my only disappointment is there no fucking machine part

  33. Rated 4 out of 5

    Mary – October 1, 2020

    First at all I really like all special class. I didn't expect much because I try reach syssygasm many times and have not success. This time was no exception, but still I got a lot of fun and good time. Looking for information I find that many gurls 😉 like me cannot reach sissygasm too, but have dry orgasms (it's cool too! and can be reach multiple times!). I don't remember if there was any information about it in the class, if not I think it's a good idea to add it.(If there was, I am sorry and I should definitely be punished).
    Of couse I recommend this class to all sissies, who think they are prepere for this 🙂
    As a wish – in one of the exams of the main course was a story with a trip to the club and some blowjobs. It would be great to see some think like this at the end of that class (and may be in a future classes).
    p.s. Sorry for bad english.

  34. Rated 5 out of 5

    Elizabeth – October 1, 2020

    It was very helpful. I Learned a lot about anal and cleaning. I would recommend it for the cleaning part alone.

  35. Rated 5 out of 5

    Roxie – October 1, 2020

    I loved it. Very engaging and informational.

  36. Rated 5 out of 5

    Kayla – October 1, 2020

    I was honestly not sure what to expect going into this class as it was the first one I have taken. With that being said the lesson plan was very easy and fun to follow. It definitely helped me push my limits and recommend it for those wanting to take the next step but maybe not sure how.

  37. Rated 5 out of 5

    Ashley – October 1, 2020

    This course was excellent for teaching the proper ways to go about inserting things anally. I really enjoyed the tasks and I learned a lot!

  38. Rated 5 out of 5

    Claire – October 1, 2020

    This class continues where the basic part left off. The assignments were well thought out and had a good structure, so I would recommend this to any sissy that wants to explore their sissy bum.

  39. Rated 5 out of 5

    Cassidy – October 1, 2020

    The assignments were all super fun! 100% would recommend to others!

  40. Rated 4 out of 5

    Haydi – October 1, 2020

    Very complete, I liked it a lot. Because of my daily life I couldn't follow it very accurately so I can't give the best feedback but I felt it very complete. It helped me, even if I couldn't do the task I've read the lectures and could learn and do it afterward. I am not at the end of it yet because I am doing it at my own speed but I can tell that I am more of a slut now than before…
    I'm doing the locktober (basic level) and I will try to not unlock myself until the end, and when I think of the pleasure I will have with my pussy I am not that scared. So thank you very much

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Audios, sissy school items (careers, extra classes, sissy training book) are all digital items and will not be sent physically. Audios and training books are downloadable digital items. Careers & Extra classes are study materials sent on your email
If you have any other questions, please contact us and we will do our best to help you out.

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