Sissy

Stories about the liberating journey of embracing femininity and submission through sissy transformation! Sissy play involves men exploring their feminine side through cross-dressing, behavior modification, and often submission to dominant partners. The appeal comes from the complete transformation, the exploration of gender roles, and the freedom to embrace a different side of sexuality. From makeup and lingerie to complete lifestyle changes, sissy stories celebrate the journey of becoming more feminine, submissive, and sexually available. It's about transformation, submission, and the joy of embracing a new identity!

Sissy Community Stories

Explore stories created by our community. Read, remix, or get inspired to create your own.

A Sissy Star is born

Nick and his girlfriend Amy are having financial problems. They try making porn to try and make money, but the straight porn market is oversaturated. Amy discovers something called 'sissy porn' that could be much more lucrative and persuades Nick to try it, turning him into Nikki, the sissy housemaid and they start making videos.

sissy
humiliation turned acceptance
S

sissy_jazmin

250

The Blacked World VR Experience

@Dirty Sex @Anal Detail @Stomach Bulge @Interracial @Humiliation @BBC Addiction @Make it Nasty @Size Matters @Anal prolapse @Spanking @Chastity Cage @Learning to Cum Anally @Interracial Body Writing @Qos Tattoo @VR Technology @Toby Toby recently got an advanced VR headset for his birthday, he's been playing with it every day, trying new games and experiences but as he begins to grow board he starts browsing more dubious sites to find new games and experiences. As he explores these new experiences he finds the quality inconsistent and lacking, pushing him to check an advertisement on one of the dubious sites for a game called The Blacked World, the ad is completely misleading and doesn't suggest what the real game is at all. It promises a great and new experience that makes Toby excited to play it but unbeknownst to him, the advertisement is false and misleading, something he doesn't realize until its too late. The game is actually a secret brainwashing and hypnosis program for hypnotizing boys into becoming addicted to interracial porn, black men and being dominated. At first the game is slow and subtle, Toby continues to return for more but doesn't know why or what the game is about. But as Toby begins to figure it out, he finds himself embarrassed and ashamed about what he's gotten himself into and the strong fetish he's developing. This story covers the slow conversion of Toby and how his new obsession with this game slowly changes his daily life. Toby begins as thinking himself as straight without any concern for sex as well as being super unknowledgeable about sex. This story should have a slow progression. IMPORTANT: There is no sex in the first chapter, only subtle suggestion and hypnosis.@#sexual hypnosis @#dirty talk @#interracial Note: Everything in this story is consensual even if it may imply otherwise. this is fantasy.

dom/sub
Interracial
Q

qosis

162

Trails of Loyalty

C and N once again strengthening their relationship with the most perveted and sexy intimate methods they can think of giving their bodies to eachother with no reservations It is their 2 year anniversary together as lovers and N had some deliciously sexy plans She had setup a little gauntlet of tasks for C to perfom these tasks will test C's devotion to her and it all entails sexual challenges She made sure to stress that failure would come with a huge punishment and of course a success would be rewarded very generously They would be 3 challenges in total The first challenge was C was to cum 10 times to a pic of N within 2 hours C found this task quite difficult as had nothing but a picture of N in a dress to jerk off too and left in a quite room He had a small cup that had marks on it and he had to fill it up to a certain level to pass N watched him closely from across the room, humiliating him and teasing him with her body and words like "If you don't love me I could just go fuck someone else" "I will walk on the streets naked" etc etc C tugged and jerked for 2 hours and almost burned the skin off his dick but he passed this round @#dark romance @#power play @#dominatrix @#dominant girlfriend @#submission @#BDSM @#dirty talk @#sissy training @#gentle femdom @#strong woman @#rough love

femdom
sissy
G

godivalocks

147

The Wife's Black Harem

Sissy Husband serves and fucked by wife and her multiple black lovers

Fetishes and kinks
sissy
E

exoticfun

75

Theatrical Submission

A story about a crossdresser who agrees to meet a couple at a sex theater called Swing Shift. He arrives in plain clothes and the wife takes him to the bathroom to feminize him (he brings everything including a breast plate, wigs, lingerie, stocking and heels). She helps him get dressed, locks him in a flat chastity cage, and does his makeup to look slutty. He's wearing a pink and white French maid outfit. She then takes him to the theater and forces him to get her husband ready by sucking his cock and a crowd forms around him. His wife gets eaten out by another sissy. When she's ready, he guides his cock into her and watches while he fucks her hard, cumming inside of her. He then has to lick both of them clean. While the couple relaxs, the wife makes him suck off other guys who come in and he ends up sucking 3 cocks. While sucking the 3rd one, the husband is ready to go again and bends the sissy over, fucking him up the ass while he sucks another cock. He cums inside of the sissy and is quickly replaced by a bbc who fucks him hard. He has his first sissygasm just before the bbc cums inside.

Fetishes and kinks
sissy
W

wilddaisy85

41

The Adventures of SuperSissy

Note: recount all these events IN THE ORDER LISTED. Write SuperSissy's first person perspective. Don't over-complicate things, structurally. During the sex scene, focus a lot on the physical sensations of Doctor Darkness's cock. SuperSissy real enjoys cock, so the sex is fun. EVERYTHING IS CONSENSUAL I am SuperSissy, the femboy defender of Rainbow City. I use my powers of flight, SuperSpeed and SuperStrength to protect truth, justice, and sexual freedom! When the wicked Doctor Darkness threatens the city with an eldritch ritual, however, I find my physical prowess worthless against his Shadow Demons. They are intangible to my blows. Overwhelmed by the demons, I am captured and brought before Doctor Darkness. There, I use my most potent, secret power - my SuperSensuality! - to lure him into ravishing me. Doctor Darkness fucks my mouth and my ass, cackling with glee when I cum from his cock in my butt. But it is I who have the last laugh. Doctor Darkness is so obsessed with defiling my nubile femboy body that he entirely misses the solar eclipse that was the keystone of his malevolent plan. The city is saved once again, thanks to SuperSissy!

Fetishes and kinks
sissy
A

annasubcd

30
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