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Ruined Sissygirl Masturbation (task)

(128 customer reviews)

19.99$

Required items

  • Inflatable anal plug
  • butt lifting underwear
  • Magic wand

If you don’t have the items click here and get this task for free!

Ruined Sissygirl Masturbation (task)

19.99$

Add to Wishlist

3 day assignment

  • Use 3 items to make you cum like a girl
  • Must follow Mistress instructions
  • Feel like a bimbo
  • Videos to watch
  • Edging
  • Cum eating
  • Affirmation
  • & more

You need to have all 3 items. Once you have the items we will email you instructions.
You can buy all 3 items by clicking here and then you get this task for free.

128 reviews for Ruined Sissygirl Masturbation (task)

  1. Brii –

    The only thing I enjoy more with this set is a chastity, it keeps me soft and limp so I can cum without getting hard, I came like a slutty girl though. It feels so nice to pull my butt lifters on knowing I'm going to be licking cum out of them. Thank you for making me more femme. 🙂

  2. Nadia G –

    This assignment was a whole lot of fun, and worth it for the vibrating wand. All the different settings make me cum like a slutty little sissy.

  3. Stephanie –

    Great assignment. Would highly recommend. Had me leaking like crazy.

  4. Nicole –

    I absolutely loved it ~ the presentation is wonderful and the decor is a real pleasure to create I highly recommend these

  5. Alice –

    Instructions easy to follow and definitely fun

  6. Michelle –

    I decided to take this assignment because I needed a push to explore more of my sissy side. The assignment was clear and easy to follow. I would recommend this to other sissies looking to try something different.

  7. Jessica –

    Great assignment, will have you so horny and wanting more juicy cock. It's so fun cumming like a girl and being shown how intimately through the instructions xoxo.

  8. Cassidy –

    I love this task, I've been doing my best, I love the wand and feel much like a good sissy girl. I took this assignment so I can do something between classes and I'm happy I did 🙂

  9. Sindy –

    That was a fun time I really like the inflatable butt plug I finally learned how to control my edging now that I know what it's called I would just jack off and cum now it's crazy the more you edge the more powerful your orgasm is…… Love cuming hard

  10. Keren –

    I took this assignment to make me feel more feminine
    The assistant was clear and easy to understand
    It was really amazing, at the end I really cum moaning like a horny slut
    I recommend this to all sissies out there, I found a new way to play with my clit

  11. Chrissie –

    I loved it, it was so fun to feel like a sexy girl and cum like one. I'd definitely recommend this is you want to feel girly and if you want someone to tell you how to cum.

  12. Aisa –

    I had never used the wand hand and very little the inflatable plug.
    The combination of the two toys has been a real delight
    I would not only recommend him to other sisters but also to those who think they are very 'men'

  13. Chantal –

    Great treat by Mistress, was shaking my whole body over and over again.

  14. Bethany –

    The Assignment was amazing it felt even better in chastity I loved every moment of it. I recommend this to anyone who wants to experience a more feminine orgasm. It was very nice and easy to follow.

  15. Nimúe –

    the assignment was easy to follow
    and it came with some decent instructions and materials

  16. Caitlyn –

    I took the assignment because it intrigued me. It made me curious about how the three items would work together. I got the buttplug and vibe wand but wondered why the butt-lifting panties. The assignments were easy to read and quite well explained. I would recommend this to other sissies because I had a lot of fun.

  17. Katie –

    Easy to follow and is so much fun how it edges you over and over again

  18. Chrissy –

    It was quite fun. Had a wonderful cummie, and licked it all up, as a sissy should. Can't wait for more assignments.
    I took this assignments to learn how to cum like a girl.

  19. Alexis –

    The assignment was great, well thought out and also gave me some more toys to play with. I was probably supposed to do the assignment on a computer but my phone worked just fine.

  20. Jasmine –

    It was amazing! I absolutely loved the assignment. I would definitely recommend this to other sissies, and it was alot of fun.

  21. Sissy Laura –

    Because of these tasks, I felt like such a slutty sissy girl. I don't think I'll ever be able to go back to masturbating like a man. Pleasuring my clitty like the woman I am is such a good feeling. I was a bit scared about submitting myself to Head Mistress Alyssa, but she made me feel like such a girl that it was worth it. I would definitely recommend it to other aspiring sissy girls.

  22. Alyssa –

    This assignment was great! I have never used a vibrator before and it introduced me to a new world of possibilities. I love this course

  23. Kandy –

    I took this assignment to learn new things about my self and to find other ways to enjoy myself You should take the course if you want to get away for the norm and learn about you

  24. Paula –

    I had never used a vibrator before. It was wonderful! I have been leaking precum all day thinking about the first 2 exercises!

  25. cristalsissygrl –

    Dearest Mistress, this sissy slut is enjoying the sessions very much . Greatly appreciate the time you dedicating to train and teach slutty sissies like me and it is extremely great assignment. Definitely would recommend to other sissies, if my humble opinion means anything.

  26. Danii –

    It was simple to follow the assignment documents and steps. It was a fun assignment and had me wet the whole time. Would recommend to other sissies.

  27. Sissy davina –

    I took this assignment to make me a perfect sissy slut. Documents are easy to read and follow and would recommend this to any other sissy. the assignment was fun and there was nothing i did not like. x

  28. Nina –

    I took this assignment because i saw good reviews on it. And for now its been very fun and exiting assignment.

  29. Kate –

    I really appreciate the huge amount of work your team are performing to make my wishes come true and turn me from a boy to a girl. I only think of cock now and pleasing men. That is what I’ve been put on this earth todo.

  30. Keri –

    This assignment brings together everything a sissy seeks! Vibrators, shaped clothing, and a plug that can grow with your ambitions -all under the care of our Head Mistress.
    I looked forward to each task and instruction.

  31. Lauren –

    I loved the assignment and had a lot of fun with it. I wish it was a tad bit longer but a sissy knows her place. The documents were easy and creatively made.

  32. SissyslutSarah –

    I really enjoyed cumming with my wand. I’m very excited for all of my new experiences. I would definitely recommend these assignments to my fellow sissy friends.

  33. Saydy –

    The assignment was a wonderful experience. Which will keep you feeling horny and girly ^^ The assignment is easy to read and follow, and the instructions are clear. I'd happily recommend it to anyone ^^

  34. Melissa –

    Had a great time. Loved the ruined orgasm and cleanup 🙂

  35. Riley –

    A fun task to enjoy even, the orgasms were delicious and mind-numbing
    The instructions were easy to follow, I recommended it to every naughty sissy out there!

  36. Olivia –

    I learned to love my little Sissy pussy Even more. Its great, that you can fill youre pussy like never before.

    I think, every Sissy should try this to get her intimate Parts better. The writing and the Assignment Parts (Videos Text and Pics) work really well together.

    Im sorry if my english isnt the best.
    Olivia <3

  37. Marissa –

    A fun thing to do this assignment, that's for sure and being told what to do was really good. Where would we sissies be without our Mistresses? If you are any sissy at all or feel slutty this is the place to go to.

  38. Julie Kiss –

    I love how that well designed set of sissy items assorted with instructions is fun and totally thought to make us really horny…
    It mades me cum, like a girl 😉 , so hard ♥
    I absolutely recommand it to other sissies 😉

  39. Alexandra –

    I really enjoyed the task. I would very much like to recommend it to others if you want to have a fantastic orgasm.

  40. Colleen Shea –

    The porn was fantastic! I have never been so turned on by porn before! I also absolutely adore the wand. You've made me a sissy slut forever!

    Thank you!
    Xoxoxo
    Sissy Colleen

  41. Brianna –

    This was a fun assignment, I had alot of fun strenching my sissy pussy out and coming in a new way. This is definitely a fun way to learn.

  42. Isla –

    This corse was pretty intense but was really fun. Would recommend to others

  43. Jenna Jade –

    Why did you take the assignment?

    I took the assignment as the toys looked perfect for training and stretching my sissy hole which I need as it is tight.

    Was it easy to read the assignment documents?

    I found the assignment documents easy to read.

    Would you recommend the assignment to other sissies?

    Yes I would recommend the Sissy Academy, this course as well as other courses provided to help us sissies embrace ourselves and to transition.

    Was the assignment fun?

    Indeed.

    What did you not like?

    There have not been any instructions yet for the inflatable dildo though I am sure that will occur within the next while.

  44. Sissy Sophie –

    I fancied trying it as a bit of an experiment. I had also been looking at bottom lifting undies so that was a bonus.
    The documents were easy to understand but the mistake I made on the first one was that should have opened it in my browser. Because of this I didn't get to report my task to mistress in the proper manner.
    I would recommend especially if you have interest in any of all of the items. The tasks are free with purchase.
    It was fun and I did find it quite challenging to edge with the wand. I didn't do so well with the first task cumming to soon. ☹️ Sorry mistress.

  45. Jayme –

    I am very thoroughly enjoying being teased and edged until I can't take it anymore. Cumming like a girl felt so good along with my verbal mantra. Would very highly recommend to anyone else interested, please give me more!

  46. Sasha Slut –

    What a wonderful assignment ❤️❤️❤️ I felt like such a good girl when I ruined my orgasms and leaked from my SOFT sissy clitty. I did have difficulty getting the inflatable dildo inside me. Some perseverance was needed – but as with everything sissy the effort is worth it. Future anal assignments hopefully will make inflatable insertions easier and easier. Thank you

  47. Myann –

    Fun combinason of tasks and gear/toy. The task also gave more ideas on how I could use them for my benefit 🙂

  48. Raven –

    When loved how much focus there was on using the vibrator in the assignment. It made me feel so girly having an orgasm and now I only want to use my vibrator. There were honestly no bad parts to this assignment, and I would definitely recommend this to other sissies

  49. Kendall –

    Really great! I had my doubts that it would actually work, I have never really leaked before without stroking but man did I leak with this assignment. I was really surprised how much the panties helped with feeling girly!

  50. Maddy –

    I thought the task was amazing and elegantly designed, there was equal parts of encouragement and a little bit of toying with words. I loved every time the task pulled into my email. <3

  51. Sophia Slut –

    I took on this assignment to learn how to use a new toy in a feminine way. The assignment is perfectly put together and easy to follow. I recommend this assignment to anyone that is pursuing improvements on their sissy lifestyle. The assignment was wonderful!! I have very little privacy, but I was still able to complete the assignment. ❤️

  52. Samantha –

    I loved being forced to watch different kinds of porn. And j also loved the whole ruining in my panties

  53. Hailey –

    This was a lot of fun to complete. The tasks were clear and easy to understand, the submission page worked well, and everything was set up to be very accessible.
    This is recommended for any sissy who needs the extra push to go for sissification of a higher level.
    It took a while for me to get into it fully, but when I did it felt so good. Very happy this task made me stick with it until I managed to do what was required

  54. Nicky –

    I wanted to learn how to cum like a sissy, the assignment was clear and offered a lot of various scenarios based on my preferences. Will definitely recommend to others!

  55. Joanna –

    I came SO hard while staying limp, it was an amazing experience! Highly recommended, it was great!

  56. Daisy Fairlady –

    Fun and love the inflatable plug. A little short.

  57. Chrissy –

    I took this assignment because I enjoy the idea of being controlled. Assignments were easy to read and follow. I would recommend to others it was a lot of fun and enjoyable.

  58. Anna –

    A gorgeous task, I really liked it, the orgasms were enchanting, it covered my head. I recommend to all girls for the perception of new sensations and your acceptance of your feminine essence!

  59. Haydi –

    Hmmm, I liked it a lot, i had chills in my head when I was using the vibrator on my clitty and thinking myself has the girl, it was making me crazy.
    So I really enjoyed it, maybe a bit longer would not be bad.

    Thank you Mistress 🙂

  60. Rachel –

    It was so much fun preparing myself and getting release like a real sissyslut, the combination of the toys and task were amazing!
    More tasks like this and I'd buy them all!

  61. Nadia –

    I recommend this to any aspiring sissies who want to take the first step, This really helped me come to grips with the slut I am.

  62. Chloe –

    Absolutely loved it, it was great having material supplied to me and the instructions were simple. Also fit into my busy schedule which was nice. Also looked forward to them every day.

  63. Juli –

    I want to be a good sissy slut.
    I had no difficulty follow the instruction.
    I would love to recommended to one i know
    It is fun
    It is hard to not cum

  64. Summer –

    i really enjoyed the assignment i really enjoyed having a girly orgasm it felt so good would love to the course again or even an extended one

  65. Lana –

    The lesson was good and made me leak I would recommend it to people who are wanting to find something new

  66. Chrissy –

    The items for this assignment intrigued me so I wanted to give it a try. It does not disappoint! It felt so good to cum using the wand and it will be how I play with my self going forward. It was a lot of fun to explore a few different ways of using it. I would highly recommend this to anyone who wants to experience being a ruined sissyslut!

  67. Amanda Stone –

    I loved the task and want more content using toys and maybe even makeup in the future. Part of me want each task to last a little longer, but I think a 3 day task is perfect for a kinky weekend and I hope to see many more tasks like it.
    Love Amanda Stone 💋

  68. Sasha –

    I was aroused all the time whit this task. The toys make me leek a lot but is short. But totally worth it.

  69. Sissy Erica –

    Yes Misstres I had some girly fun cummed in my sissy panties for the first time yesterday thank you for that I felt like a girl

  70. Brandibj –

    Thank you Mistress. I loved the assignment. I would tell other sissies about the assignment. Thank you so much Mistress.

  71. Cassie –

    I took this assignment because it sounded exciting, and i wasn't wrong. Although it was short, it was simple and memorable enough to repeat myself again and again. If your looking for ruin and be a better sissy slut I would recommend.

  72. Sissy_Deanna –

    I so loved the ruined sissyslut assignment. It was a lot of fun and had my clit leaking all the time. Very erotic and made me stay horny everyday. I just love how well it was put together.

  73. Sophia Stump –

    I had a lot of fun with this assignment! The instructions and videos really helped me to get into the right mindset. I highly recommend this assignment if you are looking for a short assignment to do in between classes.

  74. Lexi –

    The toys were so much fun! It felt so good to be told what to do by Mistress.

  75. Nozomi –

    I like the website design for the assignments 😀 For me the assignments fulfilled what I wanted out of the products.

  76. Angie –

    I would highly recommend this assignment to other sissies. it is so much fun to stretch your comfort zones (pun fully intended) and Mistress dose a great job with this. the only thing stooping me fum a full 5 hearts is i feel the panties are a little underutilized the bigger but lead me to be leave that it would be relovent beyond “feeling girlish” not that that is bad just not what i was hoping for. still it is well worth it for the stretching alone

  77. Arielle –

    Loved it so much, I've never felt more excited for the assignment than I did with this one. Highly recommend it to any aspiring sissies out there.

  78. Arielle –

    It was a great feeling to rein the sissys orgasm like a real sissy should. Im in love with my butt-lifting underwear now <3

  79. Kitteh –

    Was a lovely experience through and through. I would recommend this to other girls whole heartily

  80. Ellie –

    I took the assignment because I wanted to cum like a girl. It was very easy to follow. I would definitely recommend to other sissies!

  81. Julia –

    I felt like such a good little girl!

  82. Nikky –

    I took the assignment to help break in my brand new toys. What great fun, i love being controlled and this assignment helped me to try to get 100% out of the new toys and myself.

  83. Bambi –

    Its a good concept, and I liked the tasks, but I found the assignment to be pretty short overall. I really enjoy the tasks you give alongside item packages and feel they could be really fleshed out into full fledged assignments based around the bundle.

  84. Erika –

    I took the assignment because i am always looking for new ideas and new ways to to train. I liked it allot and would definatly recommend it.

  85. Cassie –

    The assignment was great, it was incredibly fun to be told how to use my new toys and cum. I was shivering in anticipation for recieveing each days instructions. Documents were easy to read and instructions easy to follow. I do think there should have been another day of buildup/anticipation before using the butt plug.

  86. Stacy –

    It was a very fun experience. For some reason I was extremely turn on the entire time…

  87. Alice –

    I found the assignment documents very easy to access especially the forms really easy to use. The assignments were fun and made me cum like the little gurl I am <3.

  88. Lucia –

    I found the tasks very interesting.
    The instructions were understandable, but I would add an explanation of the ruined orgasm at the beginning. Furthermore I found the video for day 1 very short.

  89. Elina –

    This was fun little assignment. If you have any interested in anal and vibrator play, try this.

  90. Myriam –

    This assignment was totally awesome. I highly recommend it to others. it was both fun and a bit frustrating too.

    Love Myriam

  91. Lily –

    Loved the assignment made me feel amazing and just absolutely loved it but wished it was slightly longer.

  92. Jessy –

    The assignment was very enjoyable. The material used as well as the interactive way that leads you step by step through the tasks is very exciting. If you want a short assignment with rather direct instructions then this one is definitely worth considering.

  93. 247ines.cis –

    would not mind if it was longer, the experience is very helpful in changing your mindset into the direction to go

  94. Juliet –

    I took the assignment to help me get that girly orgasm and it REALLY helped.
    Anybody else who has this issue should try this.

  95. Chloe Mahon –

    Absolutely love this assignment,every sissy should completer or atleast try it xx

  96. claire –

    This assignment was a lot of fun. It was easy to follow and had hot instructions. I only wish there was more of it.

  97. Joanna –

    The Ruined Sissyslut challenge was an innovative and fun way to test your sissy limits by using all three items in different ways. Combined with viewing the recommended clips, the challenge will leave you wanting more…

  98. Katie –

    I loved the miniature class and I’m glad to learn how to sissygasm. My only possible issue would be wishing the class was longer, but this is by no means a negative review

  99. Sarah –

    The assignment given was interactive and fun. Given instructions to play with oneself like a girl and ultimately finish gave great waves of pleasure to me. Overall a great assignment even if it was short.

  100. Reggi –

    Fun little assignment. Really shows how best to use these tools.

  101. chrissiechrissie –

    I love being told what to do. Headmistress had very clear instructions.
    I loved coming like a girl! Although real girls don't make as much of a mess as a sissy does.
    Only bad thing is inflatable butt plug broke and doesn't work, but I have a dildo and plug that I can use.

  102. Arella –

    Degradation as a cock hungry sissy is my kink, so this was perfect for me. Unfortunately there are only 3 task that are relatively small. The content is good but there should be more of it.

  103. Tris –

    I'm enjoying this assignment I look forward to the next email. I would definitely recommend this to other sissies it's easy to follow and easy to complete.

  104. Jenny –

    I took on this assignment because, of course, I wanted to cum like a girl. Also, I never had an inflatable plug before and I was always curious about trying one.

    The documents were very easy to read and understand. The bonus of filling out additional forms gave an extra sense of “sissy affirmation” along the way which I found very exciting.

    Financial requirements aside, I would definitely recommend this assignment to other sissies.

    My only issue with this task is that it doesn't last forever!

  105. Karina –

    very easy to read and understand
    fun assignments really showed you how much fun you can have with your new toys and I would really recommend it to others

  106. May Love –

    Had fun with it.
    Could longer.
    Want to be more humilated.

  107. Lilith –

    This is by far one of my top favorite assignments I've done for the academy I just wish my hole was better suited to such a large plug also it's made the wand my new favorite toy to use on my clit

  108. Misty~ –

    This assignment has been amazing!
    It was easy to read and follow and so much fun!
    I would reccomend it for sure >w<

  109. Claire Tiffany –

    I’ve always wanted to play with the Magic Wand so I did not hesitate when offered the assignment. I’ve had many ruined orgasms so that never worried me.
    I loved the Ruined Sissyslut assignment. For the first part I was so horny playing with the wand and having the dildo pump in my pussy…it was tough at first but licking up my cum in the end was a wonderful reward.
    I was already horny for the second part, so playing with the wand on my little clitty in my panties…it was very easy to edge and then filled my panties with my cum…they were dripping with my cum….mmmmm
    I would most definitely recommend this assignment to every sissy…I plan to do it again and again
    To make this assignment even better would be to do it with another sissy…

  110. Alexandra –

    I really liked it, I recommend it, it was really fun

  111. Kaley –

    I have enjoyed the assignment, the documents were all easy to read and understand. I will admit that the first days lesson was better than the second, at least in my humble opinion.

    I'm torn about recommending this assignment. On the one hand I have enjoyed it, as I said, but on the other it does require a financial investment for the items necessary to perform. Not a negative per say, but I tend not to assume the financial flexibility of others.

  112. Bambi –

    Well I maybe biased but I absolutely loved the assignment! The look of the task website to the fun ways you have to type and interact with it. The submission form you have to sign was a really nice touch to make it feel more real. Would love more like these I think they are the very best in this community. <3

  113. clara –

    I think the assignment were easy to read and really fun . The only downside is that the assignment isn't long enough. Two more days would have been great :).

  114. Holly –

    This was a great assignment I was looking for a way to focus my orgasms to more feminine asspects.

  115. Sandra –

    I really enjoyed it. I like to play with my ass, but I didn't know how to play with a wand. I was very curious about having a combined experience wand plus butt plug (and, of course, with panties). Instructions were very easy to follow. The assignment was definitely fun. I recommend it to other sissies.

  116. Kate –

    It is a really interesting assignment and I am enjoying it.

  117. christine –

    Great class! Lots of fun but over too quickly. However, I still have the equipment and will follow Her instructions many more times.

  118. April –

    Absolutely loved this assignment, it made me feel like such a slut and so horney for more. Would recommend it to everyone. Instructions are easy to follow and so much fun.

  119. Charlotte –

    The equipment worked perfectly and arrived promptly. When I was give instructions I felt so accomplished knowing I was making Mistress proud. After the assignment was finished I made sure to await further instructions for Mistress like a good girl. I would definitely recommend to any sissy, as it's great fun and super easy.

  120. Marcie –

    The assignment has been excellent – it's used a variety of media and stimuli, and the instructions have been very clear and easy to follow.

    I've had a lot of fun following the instructions, and this is definitely something I would recommend to other sissies

  121. Conny –

    I had already seen this wand and wanted to try it and this is best done with instructions. It gives me great pleasure to spoil myself with the magic wand. It makes me feel very intense being a girl and the female orgasms are much more intense and longer. I love it. Thank you so much for it.

  122. Courtney –

    A truly excellent assignment I was proud to be able to be a happy ruined little sissy slut. I am looking forward to further training!

  123. Alex –

    I liked it
    It was very fun
    Would definitely recommend
    Easy to read and understand

  124. Salena –

    The assignment was a lot of fun! Super easy to read and the directions were simple yet seductive.

  125. Crystal Cooper –

    Super easy to understand. I would 100% recommend. The wand was amazing. Was my first one and I loved it.

  126. Alice –

    I took the assignment out of curiousty and wanted to know exactly how you would accomplish making me cum and wow I didnt expect that it. It was wonderful and i cant wait for the rest of the assignment

  127. Baliey morgan –

    Loved ever second of it. Made me feel like a real girl

  128. Sarah slut fox –

    What an amazing assignment making me cum like a real girl. Cum on girls give it a go you dont know what your missing x

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