Sissy Cum Stories

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Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

My Mistress is My Wife Ch. 02

by slavetohiswife on Sep 14, 2017
Fetish

I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...

Sissy Driving

by MattieG on Sep 17, 2017
Loving Wives

Lindsay had been texting me for days after we met at the restaurant. I'd turned her into a little slut begging for my cock. She wasn't about to give up my dick for her husband's little sissy dick. We had been sexting nonstop since the other night so I knew she was pretty horny by now. I had been very busy with work and our schedules hadn't synced where we co...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...