Skip to content
SissyloverSissylover
  • Menu
  • Cart

    No products in the cart.

  • Academy
    • Free Program
    • Premium Courses
  • Shop
    • Clothing
      • Dresses & Costumes
        • Sexy Dresses
        • Silk & Satin
        • Latex
        • Bodysuits
        • School Girl
        • Sissy Maid
      • Tops & Bottoms
        • Skirts
        • Leggings
        • Pants & Shorts
        • Shirts
        • Matching Tops & Bottoms
      • Hourglass Figure
        • Corsets & Bustiers
        • Butt lifters
        • Waist Trainers
    • Lingerie
      • Babydoll
      • Nighties
      • Bras
      • Panties
      • Matching Bra & Panties
      • Stockings & Garters
    • Sissy Shoes
      • High Heels
      • Low Heels
    • Sissy Beauty
      • Make Up
        • Skin Care
        • Eyes
        • Face
        • Lips
        • Nails
        • Tools
      • Sissy Decorations
        • Chokers & Collars
        • Clip Earrings
        • Gloves
        • Mask
        • Hairbands
    • Sissy Toys
      • Sissy clit
        • Chastity
        • Vibrators
        • Cock Rings
        • Catheter
      • Sissy Anal
        • Butt Plugs & Dildos
        • Enema
        • Sex dolls
        • Fuck Machines
    • One stop
      • Butt Plugs & Dildos
      • Chastity
      • Lingerie
      • Wigs
      • Fake Boobs
      • Sissy Slave
      • Sissy Sets
  • Blog
    • No products in the cart.

Home / Training
Add to Wishlist
Anal Intro

Anal Intro

Rated 4.78 out of 5 based on 553 customer ratings
(553 customer reviews)

$25.00

  • Learn to actually enjoy anal within 30 days!
  • Learn how to do anal the SISSY way!
  • Cum harder than EVER before!

Already know the basics and want to learn how to take it deeper, faster and bigger?
Click here to join our anal expert class

Add to Wishlist
Browse
  • Clothing
    • Dresses & Costumes
      • Bodysuits
      • Latex
      • School Girl
      • Sexy Dresses
      • Silk & Satin
      • Sissy Maid
    • Hourglass Figure
      • Butt lifters
      • Corsets & Bustiers
      • Waist Trainers
    • Tops & Bottoms
      • Leggings
      • Matching Tops & Bottoms
      • Pants & Shorts
      • Shirts
      • Skirts
      • Tops
  • Fake Boobs
  • Lingerie
    • Babydoll
    • Bras
    • Dresses
    • Matching Bra & Panties
    • Nighties
    • Panties
    • Stockings & Garters
  • Sissy Beauty
    • Make Up
      • Eyes
      • Face
      • Lips
      • Nails
      • Skin Care
      • Tools
    • Sissy Decorations
      • Chokers & Collars
      • Clip Earrings
      • Gloves
      • Hairbands
      • Mask
  • Sissy Sets
  • Sissy Shoes
    • High Heels
    • Low Heels
  • Sissy Toys
    • Sissy Anal
      • Butt Plugs & Dildos
      • Enema
      • Fuck Machines
      • Sex dolls
    • Sissy clit
      • Catheter
      • Chastity
      • Cock Rings
      • Vibrators
    • Sissy Slave
  • Training
    • Assignments
    • Tasks
  • Wigs
  • Description
  • Reviews (553)

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 😋

Do you fantasize about LOVING the feeling of something in your ass?
  • 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.
Did you know? Unlike touching your clit, anal doesn’t necessarily stop feeling good after you cum. If that’s not enough to tempt you to take this class, I don’t know what is…
Join anal intro class

See you on the other side, sissy 💋

Head Mistress Alyssa

553 reviews for Anal Intro

  1. Rated 5 out of 5

    Anonymous – June 5, 2025

    The class was fun and I learned alot from it. It helped me get a grasp in my training. I can’t recommend it enough too beginners.

  2. Rated 5 out of 5

    Anonymous – April 30, 2025

    I love this course. I have had already a sissygasm and I’m already used to plug myself and ride toys, but with these lessons I improved my skills

  3. Rated 5 out of 5

    Noyi – April 29, 2025

    This course really helped me understand what it means to be a manly person. I am really grateful to you for this course. It is really accurate and really helps to understand what a manly person is and how to be one. Thank you very much. I really liked this course and I am looking forward to you preparing more similar courses. ❤️❤️

  4. Rated 4 out of 5

    Moha – April 24, 2025

    It’s really good, I enjoyed it

  5. Rated 3 out of 5

    Matia – March 31, 2025

    Hi,

    The content itself is good. However the course itself is too drawn out while being too slow on rolling out individual lectures.

    For me, I had a phase when I was really excited to get into to, however the structure of the course meant that I had to wait 6-7 days for the first lesson! Then multiple days for following ones. This has more or less killed my anticipation and I went to other sources to satisfy my needs.

    Course could benefit from rolling out instantly and delivering lectures at fast intervals. Due to prolonged time periods I lost interest after a few lectures and did not engage. I anticipate you may find more feedback like this.

    If the course was more compact and delivered more quickly, definitely a 5 star rating. Many thanks!

    Matia

  6. Rated 5 out of 5

    Pinkovasissy – March 31, 2025

    Super

  7. Rated 5 out of 5

    Clarissa – March 9, 2025

    fantastic, i struggled to feel pleasure from other anal before. turns out i was just moving to quickly, this has you slow down and build up and it feels way better.

  8. Rated 5 out of 5

    Julie – March 1, 2025

    This class was great. I would definitely recommend for anyone interested in anal pleasure. Im off to start the next class

  9. Rated 5 out of 5

    Jamie – January 24, 2025

    The course is a lot of fun.The most important thing I learned is to take your time when exploring your pussy,gradual steps are important to unlock greater pleasures.

  10. Rated 5 out of 5

    Kristian – January 18, 2025

    All in all good class but I need to review the course I learn best through repetition. I found it best to watch some sissy porn while playing with myself, made insertion more pleasurable.

  11. Rated 5 out of 5

    latanya – January 11, 2025

    I really enjoyed the exercises and I have become much more anal centric due to this class.Now feel much more comfortable with anal, and the desire to be able to please someone and now I can plugged for hours with no discomfort at all. Looking forward to join the anal expert course.

  12. Rated 3 out of 5

    Scarlett – January 10, 2025

    Nice class would of liked more engaging content but nice!

  13. Rated 5 out of 5

    Aysa – January 2, 2025

    I’m now gonna take the next course cause I had so much more pleasure can’t wait to start the anal expert course

  14. Rated 5 out of 5

    Alexa – December 15, 2024

    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.

  15. Rated 3 out of 5

    Linda – December 9, 2024

    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.

  16. Rated 5 out of 5

    Natalie – December 8, 2024

    Super fun course, as they all are on this site, but great intro. Now I can’t wait to start the advanced course

  17. Rated 5 out of 5

    Josie – December 6, 2024

    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!

  18. Rated 5 out of 5

    Vianna – November 30, 2024

    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

  19. Rated 5 out of 5

    Silver – November 19, 2024

    I thank you all for teaching me and making me the sissy I am ment to be thank you all

  20. Rated 4 out of 5

    Shellybabe – October 20, 2024

    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.

  21. Rated 5 out of 5

    Octavia Fae – October 18, 2024

    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.

  22. Rated 4 out of 5

    Honey – September 3, 2024

    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!

  23. Rated 5 out of 5

    Johanna – September 1, 2024

    I loved the course and how it got me to love anal. It had the right speed introducing all the new stuff.

  24. Rated 5 out of 5

    Elise – August 25, 2024

    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

  25. Rated 4 out of 5

    Malvina – August 23, 2024

    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.

  26. Rated 5 out of 5

    SissyNinja – August 23, 2024

    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.

  27. Rated 5 out of 5

    Rancy – July 27, 2024

    It was okay overall, but it felt a bit weak. It seems better to increase the intensity by tuning together with advanced.

  28. Rated 5 out of 5

    Patricia – June 12, 2024

    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

  29. Rated 5 out of 5

    Emily – May 15, 2024

    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

  30. Rated 5 out of 5

    Jordan – April 28, 2024

    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. 🙂

  31. Rated 5 out of 5

    Evelyn – April 23, 2024

    An excellent course that allowed me to discover more about myself in depth.

  32. Rated 5 out of 5

    Lexi – April 18, 2024

    This is perfect for beginners. It teaches how to play with my anus step by step without additional purchase. I really enjoyed the course.

  33. Rated 5 out of 5

    Madison – March 28, 2024

    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.

  34. Rated 5 out of 5

    Liz – March 24, 2024

    It makes fun and you become good skills for anal pleasure

  35. Rated 4 out of 5

    Jenna – March 10, 2024

    I wish he would talk more about stretching and talk more about big dildos.
    But i likes the training

  36. Rated 4 out of 5

    Nikki – March 6, 2024

    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.

  37. Rated 4 out of 5

    Nikki – February 28, 2024

    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!!!

  38. Rated 5 out of 5

    Michelle – February 20, 2024

    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.

  39. Rated 5 out of 5

    Erika – February 16, 2024

    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.

  40. Rated 5 out of 5

    Jennifer – February 16, 2024

    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!

  • 1
  • 2
  • 3
  • …
  • 14
  • →

Add a review Cancel reply

Related products

Add to Wishlist

Sissy Training Book

Rated 5.00 out of 5
$49.99
Add to cart
Add to Wishlist

Enema + Lube Insertor

Rated 4.67 out of 5
$9.99
Add to cart
Add to Wishlist

Sissy G-Spot Massage

Rated 4.67 out of 5
$14.99
Add to cart
-25%
Stretch sissy asshole before anal sex with a man
Add to Wishlist

Anal Chastity lock

Rated 4.29 out of 5
$79.99 Original price was: $79.99.$59.99Current price is: $59.99.
Add to cart
Add to Wishlist

Sexy Waist Slimming Body Shaper

Rated 4.80 out of 5
$19.99
Select options
This product has multiple variants. The options may be chosen on the product page
392-50694f.jpeg
Add to Wishlist

Transparent Corset

Rated 5.00 out of 5
$29.99
Read more
-22%
Add to Wishlist

Double Ponytail Sexy Blonde

Rated 4.00 out of 5
$43.99 Original price was: $43.99.$34.49Current price is: $34.49.
Add to cart
4598-3e4812.jpg
Add to Wishlist

Simple Metal Shower Head

Rated 5.00 out of 5
$24.99
Add to cart
PLATFORMS
  • Reddit
STUDENT SERVICE
  • About Us
  • Blog
  • Sissy Queries (in maintenance)
  • Maintaining & Wearing Wig
  • Measurement Guides
PURCHASE INFO
  • Track Your Order
  • Shipping & Delivery
  • Refunds & Returns
  • Payment Methods
  • FAQ
  • Contact us
  • Privacy policy
  • Cookie Policy
  • Terms and conditions
© Sissylover 2025
  • ACADEMY
  • SHOP
  • sissylover-wigs.pngOne stop
    • Butt Plugs & Dildos
    • Chastity
    • Lingerie
    • Wigs
    • Fake Boobs
    • Sissy Slave
    • Sissy Sets
  • Sissy Toys
    • Sissy clit
      • Chastity
      • Vibrators
      • Cock Rings
      • Catheter
    • Sissy Anal
      • Butt Plugs & Dildos
      • Enema
      • Fuck Machines
      • Sex dolls
  • lingerie-sissylover.pngLingerie
    • Babydoll
    • Matching Bra & Panties
    • Nighties
    • Bras
    • Panties
    • Stockings & Garters
  • Clothing
    • Dresses & Costumes
      • Sexy Dresses
      • Silk & Satin
      • Latex
      • Bodysuits
      • School Girl
      • Sissy Maid
    • Tops & Bottoms
      • Skirts
      • Leggings
      • Pants & Shorts
      • Shirts
      • Matching Tops & Bottoms
    • Hourglass Figure
      • Butt lifters
      • Waist Trainers
      • Corsets & Bustiers
  • Sissy Beauty
    • Sissy Decorations
      • Chokers & Collars
      • Clip Earrings
      • Mask
      • Gloves
      • Hairbands
    • Make Up
      • Skin Care
      • Eyes
      • Face
      • Lips
      • Nails
      • Tools
  • sissylover-shoes-1.pngSissy Shoes
    • High Heels
    • Low Heels
  • Home
  • Free Program
  • Premium Courses
  • Blog

Login

Lost your password?

Register

As with any site, we use cookies to make the website function properly. By clicking "Accept" you consent to the use of all cookies
Cookie settingsACCEPT
Privacy & Cookies Policy

Privacy Overview

This website uses cookies to improve your experience while you navigate through the website. Out of these cookies, the cookies that are categorized as necessary are stored on your browser as they are essential for the working of basic functionalities of the website. We also use third-party cookies that help us analyze and understand how you use this website. These cookies will be stored in your browser only with your consent. You also have the option to opt-out of these cookies. But opting out of some of these cookies may have an effect on your browsing experience.
Necessary
Always Enabled
Necessary cookies are absolutely essential for the website to function properly. This category only includes cookies that ensures basic functionalities and security features of the website. These cookies do not store any personal information.
CookieDescription
cookielawinfo-checkbox-necessaryThis cookie is set by GDPR Cookie Consent plugin. The cookies is used to store the user consent for the cookies in the category "Necessary".
cookielawinfo-checkbox-non-necessaryThis cookie is set by GDPR Cookie Consent plugin. The cookies is used to store the user consent for the cookies in the category "Non Necessary".
JSESSIONIDUsed by sites written in JSP. General purpose platform session cookies that are used to maintain users' state across page requests.
laravel_sessionlaravel uses laravel_session to identify a session instance for a user, this can be changed
PHPSESSIDThis cookie is native to PHP applications. The cookie is used to store and identify a users' unique session ID for the purpose of managing user session on the website. The cookie is a session cookies and is deleted when all the browser windows are closed.
viewed_cookie_policyThe cookie is set by the GDPR Cookie Consent plugin and is used to store whether or not user has consented to the use of cookies. It does not store any personal data.
XSRF-TOKENThe cookie is set by Wix website building platform on Wix website. The cookie is used for security purposes.
Non Necessary
Disabling these cookies will affect your shopping experience. For example, the wishlist will not function as it should. These cookies also help us track orders and provide better/faster support. These cookies are also used to see what products are most popular and what products we should add for sale or remove.
CookieDescription
_gaThis cookie is installed by Google Analytics. The cookie is used to calculate visitor, session, campaign data and keep track of site usage for the site's analytics report. The cookies store information anonymously and assign a randomly generated number to identify unique visitors.
_gatThis cookies is installed by Google Universal Analytics to throttle the request rate to limit the colllection of data on high traffic sites.
_gidThis cookie is installed by Google Analytics. The cookie is used to store information on how visitors use a website and helps in creating an analytics report of how the website is doing. The data collected including the number visitors, the source where they have come from, and the pages visited in an anonymous form.
_omappvpThe cookie is set to identify new vs returning users. The cookie is used in conjunction with _omappvs cookie to determine whether a user is new or returning.
_omappvsThe cookie is used to in conjunction with the _omappvp cookies. If the cookies are set, the user is a returning user. If neither of the cookies are set, the user is a new user.
prism_251956309The cookie is to link sissylover active student visits with their student profile. Necessary to make recommendations, provide support and send appropriate emails
sbjs_currentTracks the URL where you came from and UTM tags. UTM tags are added to the end of regular URL’s and are designed to tell Google Analytics (and other analytics tools) a little bit more information about each link and which marketing campaign it relates to.
sbjs_current_addAdditional info about a visit such as timezone and where you have been referred from.
sbjs_firstThese hold the same information as sbjs_current & sbjs_current_add but hold the data of the first visit only it is never overwritten.
sbjs_first_addThese hold the same information as sbjs_current & sbjs_current_add but hold the data of the first visit only it is never overwritten.
sbjs_sessionHolds data about the current page URL and how many pages have been seen in the current session.
sbjs_udataFurther User information such as number of visits, the i.p address and browser name.
woocommerce_recently_viewedIt is used to show you a list of items you recently viewed on sissylover. It is shown on the website.
yith_wcwl_session_96b6c2e14a298a8aacd485caf4831926This cookie remembers your wishlist. Without it, the wishlist cannot function properly
Save & Accept