Sissy Cumslut Stories

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Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Tara's Training Ch. 02

by cumlover10 on Nov 18, 2019
Fetish

"Don't you dare wipe that cum off your face, but I want you to clean up your asshole and make your slutty panties look good again." Tara started to walk out of the room before she turned back and paused before asking one question, "are you sure you want to be my little cumslut tonight?" My heart was pounding, fresh cum still overwhelming my nostrils and tast...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

My Sweet Sissy

by J3sus on May 13, 2020
Letters & Transcripts

All characters are above 18 Vocabulary: Cock= Clit Asshole= Pussy * Dear Sissy, How have you been? Do you miss mommy? I bet your tiny clit is itching inside those sweet panties, the same panties I bought for you at that lingerie store. Those lacy pink ones I love so much. I can already imagine your hard on in those panties. I can imagine your small clit...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

The Emergence of Jocelyn

by JocelynF99 on Sep 17, 2017
Loving Wives

"Oh daddy. Oh daddy, you make me feel so good." "Oh daddy, you make me so hot for your body." "I love it when you touch me. You make me feel so good." "Please daddy, please daddy, make love to me." "I need you so badly." "I need you inside me." "Ohhh, OOhhh..." "Please daddy, make me your woman." "Please daddy, please daddy, please fuck me." "Oh God...

Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...