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!

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#JANUARY

• January 1: New Year’s Day - sissies make resolutions for their training which they intend to keep for the year

• Third Friday of January: International Fetish Day

• Broadcast Event: AVN Awards Transgender Performer of the Year

• Broadcast Event: Miss Gay America drag pageant

• Local Event in Las Vegas: AVN Adult Entertainment Expo

#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

• July 14: Non-Binary People’s Day, at the end of Non-Binary Awareness Week

• July 16: International Drag Day

• Local Event in San Francisco: Up Your Alley Fair

#AUGUST

• Local Event in New Orleans: Southern Decadence

#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

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#Other Local Events of Interest

• RuPaul’s Drag Con

• Exxxotica Expo - happening this year in Miami, Chicago, New Jersey, and Washington DC

#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.