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

#FEBRUARY

  • 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

  • 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

  • Carnival and Mardi Gras - public crossdressing and debauchery are often celebrated at these events

#MARCH

  • Beginning of Spring - sissies start dressing more skimpily, admire the pretty flowers of spring, and often head south to party for Spring Break

  • March 17: St. Patrick’s Day - sissies wear green and try to get lucky

  • March 31: Trans Day of Visibility

  • 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

  • May 5: Cinco de Mayo

  • May 9: National Masturbation Day - sissies celebrate by trying dildos

  • Second Sunday in May: Mistress’s Day - alternative to Mother’s Day, in which sissies with Mistresses are extra obedient to them

#JUNE

  • Beginning of Summer - sissies perfect their beach bods so they can show off their bikinis to all the guys

  • 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!

  • Third Sunday of June: Daddy’s Day - sissies try extra hard to please their Daddies

  • Broadcast Event: Miss International Queen transgender beauty pageant

#JULY

#AUGUST

#SEPTEMBER

  • Beginning of Fall - sissies switch to warmer clothes like leggings and begin drinking Pumpkin Spice Lattes

  • September 16-23: Bisexual Awareness Week, culminating in Celebrate Bisexuality Day

  • Oktoberfest - sissies wear cute dirndls

  • Local Event in San Francisco: Folsom Street Fair, the last Sunday in September after Leather Pride Week

#OCTOBER

  • All Month: Locktober - sissies attempt to lock themselves in chastity for the entire month

  • 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

  • October 31: Halloween - crossdressing is often accepted at Halloween, including at events like the Rocky Horror Picture Show

  • Local Event in Provincetown, MA: Fantasia Fair/Trans Week

  • Local Event in Key West, FL: Fantasy Fest

#NOVEMBER

  • 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.

  • Fourth Thursday of November: Thanksgiving - sissies give thanks to their dominants and in return, they get stuffed

  • Black Friday & Cyber Monday - great opportunities for sissy shopping trips!

#DECEMBER

  • Beginning of Winter: sissies stay inside and have Daddy help keep them warm

  • 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.

  • All Month: Sissy Holiday Season - sissies exchange gifts in holidays like Sissymas, Sissy Hannukah, and Sissy Kwanzaa

  • 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

#Other Suggested Days

  • 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.

  • Sissyday: equivalent to a birthday, this is the yearly anniversary of the sissification ceremony. It marks when a sissy truly became a sissy.

  • Anniversary: if a sissy has a master or mistress, she may celebrate the yearly anniversary of their bond.