A few years ago I made a post detailing some speculative sissy holidays. After seeing a suggestion that Father’s Day be celebrated by sissies as “Daddy’s Day”, I got inspired to make a new calendar with more holidays.
However, this quickly got out of hand as I threw in every vaguely sissy-related event I could think of. Hopefully you gurls will get something out of the time I spent on this!
Also, please leave suggestions below for any events I’ve left out, your original ideas for events, or pre-existing events from around the world!
#JANUARY
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January 1: New Year’s Day - sissies make resolutions for their training which they intend to keep for the year
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Third Friday of January: International Fetish Day
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Broadcast Event: AVN Awards Transgender Performer of the Year
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Broadcast Event: Miss Gay America drag pageant
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Local Event in Las Vegas: AVN Adult Entertainment Expo
#FEBRUARY
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Second Sunday in February: Super Bowl Sunday - sissies please their Daddies while they watch the big game, or dress up as cheerleaders to show team spirit
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February 14: Valentine’s Day - sissies give gifts to their beloved Master or Mistress, go on dates if they don’t have one, or just spend quality time with other sissies
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Carnival and Mardi Gras - public crossdressing and debauchery are often celebrated at these events
#MARCH
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Beginning of Spring - sissies start dressing more skimpily, admire the pretty flowers of spring, and often head south to party for Spring Break
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March 17: St. Patrick’s Day - sissies wear green and try to get lucky
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March 31: Trans Day of Visibility
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Broadcast Event: Transgender Erotica Awards
#APRIL
- Easter - sissies dress up like bunnies, hide eggs up their butt, and go looking for a nice big carrot
#MAY
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May 5: Cinco de Mayo
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May 9: National Masturbation Day - sissies celebrate by trying dildos
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Second Sunday in May: Mistress’s Day - alternative to Mother’s Day, in which sissies with Mistresses are extra obedient to them
#JUNE
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Beginning of Summer - sissies perfect their beach bods so they can show off their bikinis to all the guys
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All Month: Pride Month - this is a great opportunity to go to a pride event in drag or crossdressed and reveal your sissy self; you might even meet other sissies or dominants!
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Third Sunday of June: Daddy’s Day - sissies try extra hard to please their Daddies
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Broadcast Event: Miss International Queen transgender beauty pageant
#JULY
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July 14: Non-Binary People’s Day, at the end of Non-Binary Awareness Week
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July 16: International Drag Day
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Local Event in San Francisco: Up Your Alley Fair
#AUGUST
- Local Event in New Orleans: Southern Decadence
#SEPTEMBER
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Beginning of Fall - sissies switch to warmer clothes like leggings and begin drinking Pumpkin Spice Lattes
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September 16-23: Bisexual Awareness Week, culminating in Celebrate Bisexuality Day
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Oktoberfest - sissies wear cute dirndls
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Local Event in San Francisco: Folsom Street Fair, the last Sunday in September after Leather Pride Week
#OCTOBER
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All Month: Locktober - sissies attempt to lock themselves in chastity for the entire month
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October 11: National Coming Out Day - sissies might consider revealing their sissy nature to people they know on this day; this would be a favorite day for sissies who love exposure
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October 31: Halloween - crossdressing is often accepted at Halloween, including at events like the Rocky Horror Picture Show
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Local Event in Provincetown, MA: Fantasia Fair/Trans Week
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Local Event in Key West, FL: Fantasy Fest
#NOVEMBER
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All Month: No Nut November - sissies who succeeded in the Locktober challenge might take this as a release day for a reward. Other sissies who succeeded might challenge themselves to go another month locked. Sissies who failed Locktober or who don’t have a cage can use NNN as a challenge as well.
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Fourth Thursday of November: Thanksgiving - sissies give thanks to their dominants and in return, they get stuffed
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Black Friday & Cyber Monday - great opportunities for sissy shopping trips!
#DECEMBER
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Beginning of Winter: sissies stay inside and have Daddy help keep them warm
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All Month: Don’t Unlock December - sissies who stayed locked in October and November can continue through December. If they succeed yet again, they often commit to remain locked through the entire next year.
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All Month: Sissy Holiday Season - sissies exchange gifts in holidays like Sissymas, Sissy Hannukah, and Sissy Kwanzaa
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December 31: New Year’s Eve - sissies party, set girly and slutty resolutions for the next year, and wait for balls to drop in their mouths at midnight
#Other Local Events of Interest
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Exxxotica Expo - happening this year in Miami, Chicago, New Jersey, and Washington DC
#Other Suggested Days
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Sissification ceremony: this is a one-time occasion marking an individual’s transition to sissyhood. Although it is called a “ceremony”, it might be something as simple as taking a cock up the ass, or as complicated as a debutante ball or induction ritual where a sissy gets her new name.
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Sissyday: equivalent to a birthday, this is the yearly anniversary of the sissification ceremony. It marks when a sissy truly became a sissy.
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Anniversary: if a sissy has a master or mistress, she may celebrate the yearly anniversary of their bond.
Love this! 💕💕💞
I should add 4th Sunday of Lent is an alternative Mother’s Day (Mothering Sunday). Having 2 Mistress days in a year would be lovely. Also Mardi Gras is “Fat Tuesday” in French (and Shrove Tuesday/Pancake Tuesday in the UK). Fat Tuesday could also be a day for letting fat alpha cocks into your holes.
Those are great ideas! Thank you so much for the suggestions!! <3