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Sissy Advent Calendar 2019

(78 customer reviews)

44.99$

We stop selling this product from 23rd December

  • This is 2019 years edition
  • You can choose when you want to start calendar
  • 1 assignment per day
  • 25 assignments in total

Out of stock

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Advent calendar with a twist. Every day you get to open a calendar window and see what’s inside. Hint: you will not find chocolate!

What is the Sissy Advent Calendar?
Digital advent calendar
1 task every morning for 25 days

What assignments are included?
There are a variety of tasks. From simply wearing panties to swallowing your own cum

What do you need to fulfill assignments?
Most of all you just need an obedient mind.

Recommended items (not necessary):
Panties
Dildo
Butt plug

NOTE! This is a digital product, all the assignments are sent on your email.

78 reviews for Sissy Advent Calendar 2019

  1. Michelle –

    it was fun little tasks that help get over some fear you might have

  2. Dixie –

    I liked this calendar so much cus it was loaded with tasks that i enjoyed and learned some things i have too work on to be a better obedient person so thank you for doing the calendar

  3. katorio –

    I enjoyed this calender, so I should do sissy tasks every day. I’m very proud of my feminine side, I feel so happy thinking of me sissified….

  4. Barbie –

    It was fun. I think it should be a little more daring though. Push the Sissy limit a little further

  5. Erin –

    If was fun. I just bought it too late. Maybe next year I’ll remember to start earlier. I loved it. It made everyday just a little more exciting.

  6. Summer –

    i loved the calender mist becuase of the amount of cum i got to eat

  7. Vicky –

    I liked the calendar for the stuff it had you do, but some are for sissies that like to flirt with guys and i am not really comfortable with that.

  8. Callie –

    I would have liked this years much more I think. I missed the deadline to purchase this years calendar.

  9. ginger –

    It was really fun would’ve liked more anal takes though 😉

  10. Sissy Jill –

    Was fun 🙂 some i didnt do due to being to busy at the time, but i enjoyed most of it 🙂 thankyou headmistress alyssa

  11. Cecilia –

    I consider this calendar is fun though I missed some of the tasks. I feel uncomfortable when I was asked to submit my picture, but other tasks are useful and let me become a better sissy.

  12. Penny –

    I liked this calendar quite a bit and the 2020 is even better. I looked forward to my ‘task’ each day. Often, I was up before I got the e-mail & felt like a kid on Xmas morning.

  13. Kayla –

    A great 25 days of tasks. All of the tasks are creative and push yourself to do them. While not easy, it was the most feminine I’ve ever felt during these last days.

  14. Kitteh –

    It was quite enjoyable and never would of expected the tasks to be given 🙂

  15. Anonymous –

    Loved the “private” tasks. My social awkwardness/anxiety got in the way of the other ones but that just means it's something I need to work on. Would have liked some more punishments for not completing tasks such as chastity until the next task is completed or no cumming until the next task etc.

    Overall though it was a very well put together advent callendar and didnt have any repeating tasks lile some of the others I've seen. I'll be buying next year's for sure and may get the 2018 one if it's still available to do a month in the middle.

    Much love,

    Sissy Bailey Cummings xoxox

  16. Ashley –

    I liked the calendar because it was s fun way to count down the days to the holiday. Some tasks were more challenging than others and others were a lot of fun. There was a good balance. It was very exciting not knowing what the task was going to be each day and then seeing that unread email with instructions.

  17. Anonymous –

    I did enjoy the 25 days of daily tasks alot and it gave me a alot to think about my self and my femininity. I actually couldn't wait for the next task to arrive every morning. There were some tasks that I wasn't able to complete like taking a picture of myself and posting it, but most of the tasks were easy enough and pushed me to think differently. There could be more video suggestions though. Overall it was fun and exciting experience and would do that all over again.

  18. Alice –

    Idid enjoy ot, it was fun and enjoyable but I didnt have the courage to do many things.

  19. Anonymous –

    really like the morning surprise

  20. Milly –

    I did every task except for uploading pictures.

  21. Danielle –

    I enjoyed this advent calendar. I was hoping for a few more ideas that would have pushed my comfort level. I am a little further along in the course though so I understand that this was created for all sissies, not just me 🙂 The concept is wonderful and fun and I recommend it🥰🥰

  22. Joanna –

    Overall I liked it but unfortunately I got ill (lung infection I believe) for a couple of weeks before christmas and therefore more or less was out of it… 🙁 Most was/seemed fun but those requiring interaction with others were/seemed a bit difficult for me…

  23. Ericka –

    I tried to apply each task, but not always easy. I liked having a task to perform every day, it makes you feel good in your sissy skin. I was not ashamed of what I could do. It is a beautiful and encouraging experience to want to be even more female

  24. Kai –

    I liked it very much because i got an mostly easy to Do task.
    There have been a few Translation Problems to german, because of my Not so good english.
    And i couldnt finde long limb dick hypno Videos. A link would have been very nice.

    Thank you for the funny time and have a happy new year.

  25. Linda –

    It reinforces and strengthens feminine traits. Keeps female thoughts multiplying in my brain waves. helps separate the woman from the man. Love Linda, I need a cock

  26. Jade –

    It was ok. I think the program is much more engaging. To be honest I found some of the objectives kind of stupid like day 11, 16, and 24. I think I would have preferred if it built on itself within a theme. It was a little too random. I get that the randomness is part of what am advent calendar is but maybe it doesnt work as well for sissy stuff idk.

  27. Kimberly –

    I liked it overall there where some task a bit out of my comfort zone, and some where I was in doubt if face would be seen so I avoided those, but fun little thing to wake up to each day.

  28. Bambi –

    I liked this calendar a lot even though I couldn't complete every task, I tried my best to be the most obedient sissy i could.

  29. Angela –

    I found myself look forward to opening my Inbox everyday. The anticipation of bring able to read the days task and whether I would be able to satisfy the request. Though I wasn't able to complete each task, I enjoyed the calender immensely.

  30. Kimby –

    I loves the sissy Carlander it made me want to be a sissy so much more then before and I felt so good wen I did the task it made me happy and relaxed.

    The tasks was so perfekt i loves most I had to were lip blam and kiss my mirror and watch Abery Kate porn she is my favorite TS porn star, And wen I was forced to eat my one cum.

    This made me to embrace my feminine side like nerver before and I cant weait to see how next year Will be.

    Big thanks to the head Mistress Alyssa and miss Frida and the academy for this wonderful christmas gift And for my new happy sissy life

    sissy Kimby wish you all a wonerful new year off 2020

    Kissies

  31. Sarah –

    Liked the calendar quite a bit, some of the tasks pushed my limits nicely

  32. Veronica –

    I enjoyed the calendar and looked forward to what the task would be every day. The tasks pushed me a little further than I was willing to go before, which felt very exciting.

  33. Astrid –

    It was fun doing the tasks and it put me more in a sissy mindset.
    I know have found a mistress for 2020 that will help me get even more sissyfied 😀

  34. Tammy –

    I loved this calendar. I am really happy I took it. Every day in the morning I woke up with a big smile like a little child, excited to see the task.
    Some of the tasks pushed me to my limits and I had to spend some time encouraging myself (it made success so much more satisfying).
    Needless to say, completing these tasks made me more confident about my feminine side of being. Thank you for making December special to me.

    Tammy

  35. Latyana –

    These calendar task were quite interesting to do. Howewer i can t do it all because i live with my girlfriend and i follow her desire about sissification so i am clearly not interested in gay porn and i am not a english native so happy sissmas is quite difficult to wish to someone.

    To sum up it was a very good calendar, i hope next year, there will be an other one ^^.

  36. SissyBambi –

    I loved the Callander, not all the tasks were sexual and they really pushed me as a sissy to do things out of the normal routine.

  37. Prisvielle –

    I liked the diverse set of tasks the calender offered. It was a good mix of easy tasks and tasks that pushed me further along. The only thing I disliked was, that my regular training was paused during it.

  38. Aster –

    I liked the idea of having daily assignents and often couldn't wait for the next day to get the next one, but i disliked some tasks, for example the gay tasks where i need to chat in a sexual way with a guy or writing that i like to please men, … are a no for me since I'm straight and don't want to change my sexuality just because i like to look and act feminine, when I look how I'm a sissy, then it's in a way that I act and look like a girl, but a lesbian one, I still like the dildo and cum eating tasks though since that's something a mistress could ask too. Except for the gay tasks I liked it, I was just sometimes sadly not in the mood to do a task or I had no opportunity.

  39. Cori Annder –

    Hello!! Thank you very much for the fun calendar.
    I enjoyed myself very much, wish I could have something like this every day!
    It really helps
    Thank you again for everything!
    You girls are amazing!
    May you be showered by many many well endowed men and complemented by every sissy and girl for your beauty

    Hearts always
    Cori Ander

  40. Sadie –

    I enjoyed thoroughly enjoyed the calendar! There were some task i could not complete due to schedule and living arrangements. But overall I got to do wonderful things that made me happy as a Sissy. Thank you so much!!

  41. Mandi –

    I really enjoyed the calendar but found it difficult some days to find the time to complete the task. I am however looking to complete the tasks again as of Jan 1st and seeing if I can be a more obedient sissy slut.

  42. Nikki –

    I loved it but was scared to do some of the ones that were required to do in public since everyone is out of town for holiday. Would buy again though next year when I&#039

  43. Kristen –

    I enjoyed it. Some days I couldnt do because of family visits

    I would like a version next year that is even naughtier

  44. Courtney –

    I loved the calendar very much it made me so happy to have a sissy task w wry day and reaffirm my sissy commitment each and every day!

    I loved all the tasks and look forward to 2020!

  45. Sluttydoggo –

    It was a great calender some challenges were a bit hard but some were funny to do. I like to express my feminity as much as I can to myself to be a good and obedient sissy. I hope I did good 🙂

  46. Daisy –

    I really liked the calendar. All tasks were very interesting, and every morning I was waiting for a new task. I tried to complete each task, but some were too complicated for me. Yes, on the net I can be very sociable, but in real life I am still very shy sometimes. But the calendar helped me overcome some of my internal barriers, thanks 🙂

  47. Bambi Zilla –

    It was fun. I&#039

  48. Jessi –

    I loved this. It really pushed me to do things out of my comfort zone. It felt like every day waking up was Christmas because I had a little present waiting for me in my inbox. Thank you for creating such a lovely task list.

    -Jessi

  49. Natalie –

    I really enjoyed the calendar! I got daily tasks, some of which were more challenging than others. I only wish I could have completed them all. Thank you for putting together such an amazing assignment! Merry Sissmas!

  50. michele –

    I loved this sissy advent calendar for soooo many reasons.
    I loved the suspense of waiting for each task to arrive. some of the task were simple and some were an emotional challenge and definitely pushed my sissy limits. However, that's a good thing. It was helpful with my sissy school training by helping keep me in the correct mindset. Now I am definitely going to take some advanced training courses to further my sissy education.

  51. Hadley –

    Getting these daily tasks made me hungry for more. It finally made me realize how much of a sissy i am and how much i still have to improve to be the best sissy i can be.
    Some tasks were difficult to do but thats the fun of it. It made me do tasks with a big smile, tasks i would never have done before. Would love some more at home tasks (fucking or sucking orders). Thanks for the amazing program!
    Love, Hadley

  52. Lexy –

    I really enjoyed the calendar it was really fun to do and I was always so excited to check my email first thing in the morning. I especially liked it when my name was in the email. I completed some of the tasks a few days late and I still plan on completing the rest of the tasks although I had a really hard time with the tasks that involved other people. I don't think I'll be able to complete task 23 though that one seems especially difficult. Thanks so much for doing this.

    P.S. My favorite task was day 21 sending you a sexy picture of myself was so hot and I would love to do something like that again.

  53. Clara –

    i liked this calendar even if i didn’t do all tasks

  54. Lilly –

    I really liked this calendar because it made me feel cute and feminine all the time

  55. Brandi –

    i really enjoy this calendar. i completed most task (i had a really tough time not thinking about cocks for a day) i will do it again next year to complete the set

  56. Suiren –

    i loved this calendar! Although, i wasn't able to get Day 12's shaving task done since i did that the day before so there just wasn't anything left to shave. However, the calendar really affirmed my feminine side and it was fun; it's like a fun adventure for sissies like me. my favorite tasks were Day 18 and Day 23 because those gave me an excuse to call in sick and just go out all dressed up; people gave me looks, but i didn't care. i even got to have some lewd fun with men because of these tasks 😉 this has boosted my confidence overall.

  57. Jessy –

    Apart from the fact that I received day 1 on time but day 2 (and all following days too) two days late it was enjoyable but not necessarily great.

  58. Molly –

    I liked the calendar, it's a fun way to give a variety of tasks and help get in touch with femininity. The tasks being daily was very encouraging.

  59. Josie –

    I enjoyed the daily emails and task. The interaction tasks went over really well. The last week was challenging with a full house of family staying with me but I did my best. Possibly the last week is good for incognito task such as a but plug or interaction task. Look forward to next years.

  60. Brenda –

    I loved it it really made me push myself into a feminine mindset

  61. Amanda –

    I likes it very much. It was exiting to open a new one every day.

  62. Davina –

    I enjoy the tasks set on each day sometimes I found it hard to over come my fears but encouraged myself to go through with the, it was an enjoyable experience and 1 I'm sure I will repeat many times

  63. Jessica –

    The calendar was amazing again, was kept on my toes waiting for the next day. I unfortunately wasn't able to complete everything due to circumstances with family.

  64. Evandra –

    It was fun to get an assignment everyday before work. Some of them also made my day way more interesting. Some tasks were super easy and others more challenging. I like that it was scattered difficulties instead of just getting harder and harder. Over all I&#039

  65. Sara –

    I liked this calendar, but in my opinion was better the last year. there were some dificult challenges and since the locktober I'm not in the mood anymore as it splitted my sluttification module. I'm trying with my cell mate chastity, but I'm not aroused as I used to be… maybe is the stressful life I'm having lately… hopefuly i will be better in 2020.
    the overall is good. Funny the thing of going into a shop to buy lingerie. Nobody ask for who are them!

  66. Missylimpa –

    Loved the calendar, it was a lot of fun!! A couple of the tasks I couldn’t complete due to my situation but every morning I would be so eager to receive the new task. Top job and would definitely do it again. You just reminded me I still have a piece of paper in my pocket saying “My name is Missy Limpa and I LOVE to please men”

  67. alisa –

    hi i liked these kind of tasks it was so arousing and it pushed my sissy self forward
    thank you very much for making this

  68. Stephanie –

    I really enjoyed getting a new task each day, made it feel like a special festive season.

  69. Alexa –

    I Really like receiving tasks, so i thought this would be a fun things to try.
    i Really liked the fact that i would get a tasks each morning, so i either have something fun to do throughout the day, or i can think about the tasks I have to do when i get back home.
    the tasks where fun, only a few sexual tasks, but that didnt make the rest less fun.

    I would definitely recommend this if you like getting tasks. It may not be something for those looking for something very sexual, but more for those looking for sissy tasks in general

  70. Zoey –

    I really enjoyed the Advent sissy calender it excited me to wake up every morning.

  71. Danielle –

    I liked this calendar a lot the task were fun to to do and I can&#039

  72. Clara –

    The anticipation to see the task made performing it way better than it normally would be.

  73. Candi –

    I really enjoyed the advent calendar challenges as they were either very fun or pushed my boundaries. Taking the imitation pose was especially erotic to me as I am very shy and uploading the picture was like taking a burden off my shoulders! The only challenge I failed was the 23rd due to not having any time in the day to do it. I feel far less shame about being the sissy I am after the advent calendar challenges.

  74. Sophie –

    I really loved the idea of having a little challenge every day. Some task where a little harder to complete, but I tried my best to get out of my comfort zone. I even complete some of the tasks days later and hope I can complete those I couldn't. Overall, really good mix of tasks to help you explore and achieve you sissy goals 😘

  75. Amber –

    It was pretty fun. I was able to do all of them but the pose photo, ran out of time before finding a way to take the picture alone. I was hoping for some tasks to be dealing with anal.

  76. Laura –

    I had a lot of fun with it. I wish you had more tasks that were picture related, but that's because I like to try to show my sissy self off

  77. Samantha –

    I loved this calendar! I participated in last years as well and this was a big step up! The tasks were varied and a bit more challenging which was great. They all came in around the same time each day which was my big gripe with last years. I love waking up to tasks even if I couldnt do them all this year due to holiday stuff coming up. I hope you do it again next year I love them!

  78. CUNTy –

    Absolutely & Deliciously Naughty! 🥰💋♨️

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How do you ship packages?

Packages from our warehouse in China will be shipped by ePacket or EMS depending on the weight and size of the product. Packages shipped from our US warehouse are shipped through USPS.

Do you ship worldwide?

Yes. We provide shipping to 185 countries around the world. However, there are some location we are unable to ship to. If you happen to be located in one of those countries we will contact you.

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We are not responsible for any custom fees once the items have shipped. By purchasing our products, you consent that one or more packages may be shipped to you and may get custom fees when they arrive to your country.

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Shipping time varies by location. These are our estimates:
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Yes, you will receive an email once your order ships that contains your tracking information. If you haven’t received tracking info within 5 days, please contact us.

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For some shipping companies, it takes 5 business days for the tracking information to update on the system. If your order was placed more than 5 business days ago and there is still no information on your tracking number, please contact us.

Will my items be sent in one package?

For logistical reasons, items in the same purchase will sometimes be sent in separate packages, even if you've specified combined shipping.

Do you send digital items?

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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