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

354

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

275

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

195

The Wife's Black Harem

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

Fetishes and kinks
sissy
E

exoticfun

104

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

104

Bonding with Billie Joe

First person narrative about a man named Aaron. I am driving across town to take care of Billie Joe’s and Becca’s cats while they were out of town. I’d always found Billie Joe… very attractive. She has red hair, a curvy yet petite body, and huge breasts with both nipples pierced. I know this because I have seen her once in a tank top and her breasts left me speechless. She also posts a lot of very sexy and slutty photos on Instagram. Anyway, I drove across town to their house, a modest little place not far from campus. The moment I stepped inside, I was greeted by the sound of soft meows and the faint scent of vanilla. The cats—two fluffy tabbies—rubbed against my legs as I made my way to the kitchen to fill their bowls. But as I sat in the living room, waiting for them to finish eating, my eyes wandered. Billie Joe’s bedroom door was slightly ajar, and from where I was sitting, I could see a glimpse of her dresser. Curiosity clawed at me like a persistent itch I couldn’t scratch. I shouldn’t. The voice in my head was firm, but it was no match for the pull of my curiosity. Before I knew it, I was standing in her doorway, my hand trembling as I pushed it open. The room was slightly messy, but in a way that felt intentional. Clothes were strewn across the bed, and the air smelled faintly of her perfume. My eyes landed on a small pile of lingerie on the dresser, and my stomach twisted with a mix of guilt and curiosity. I step over to the dresser and pick up the lingerie. A black lace bra with matching panties and a garter belt. I raise the panties to my nose and I inhale deeply, taking in her sweet, musky scent. I glance over to her closet and see a stunning pair of black high heels. Wow, I have seen her wear these on her instagram before, I thought to myself. Then, the thoughts bombarded me—the need to try on her clothes and her shoes. No way, I can’t do that, I told myself, that’s crazy. But as I pick up her shoes, and imagine the straps wrapped around my ankles, I get goosebumps all over my body. Okay, maybe just really quick, and then I will get dressed again and leave. I quickly strip off my clothes and let them fall onto Billie Joe’s bedroom floor. I took my Adderall earlier in the day which caused my penis to shrink. It was currently barely a half inch long, and was curling in on itself, my head almost completely disappearing inside itself. It looked like a small, soft clit. I pulled her panties on, covering my little clit, and my tight boy pussy. Then I put on the matching bra and garter belt. I felt so sexy and slutty. I quickly looked in her closet and found a short skit and crop top and put them on. My heart was pounding out of my chest with excitement. Now, for the best part. I sat down on Billie Joe’s bed, feeling my bare cheeks rest on her cold sheets. I put on the six inch high heels and strapped them around my ankles. I stand up and check myself out in her large floor mirror. I can’t believe I am actually wearing Billie Joe’s clothing. It is so hot. I felt my little clit leaking pre-cum. I am even getting wet like a girl, I thought to myself. And then I saw it. A metallic butt plug glinted in the sunlight streaming through the window. My breath hitched as I picked it up, turning it over in my hands. It was cool to the touch, and the weight of it made my imagination run wild. “What the hell are you doing in here?” I spun around, the butt plug slipping from my fingers and clattering to the floor. Billie Joe stood in the doorway, her arms crossed over her chest and her expression unreadable. “I—uh—” I stammered, my face burning with embarrassment. “I was just… checking on things. Making sure everything was okay.” Her eyebrows shot up. “In my bedroom?”

Fetishes and kinks
sissy
S

spamaladingdong

84
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