Sissy Cocksucker Stories

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Orientation
Length
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Infinite Scroll

The Chief Pt. 02

by Aunt_Joanne on Sep 16, 2017
Transsexuals & Crossdressers

I awoke the next morning to the aroma of bacon frying. I was alone in a strange bed, and for a moment, I couldn't remember where I was. Then it all came back to me. It hadn't been some vivid erotic dream. I was lying in another man's bed, naked except for a pair of pink nylon panties. My stockings and garter belt were discarded on the floor, and my male clot...

The Settlement

by cathynylons on Sep 12, 2017
Transsexuals & Crossdressers

While my wife was away visiting her mother for a week I had a wild fling with Kate, the sexy new secretary at my office. A young tart about 22 yrs. old in tight skirts and spike heels. She drove me crazy and before I knew it we were doing it on my desk with our clothes mostly on. Then, at her place near the beach and then, on the beach at night. Wild times....

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

The Sissy and The Gardener

by snorn on Sep 16, 2017
Transsexuals & Crossdressers

As I sit in my office, I am wearing my pink sissy uniform, watching the hired gardener dig up the weeds out front. I'm not supposed to expose myself to others, but my sissy rules state that I must be in uniform when nobody else is inside the house. I'm doing work, but all I can really concentrate on is the idea that I should be on my knees sucking cock, or b...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

My First Time as a Sissy

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

I had moved away from home to go to college at 18. I had been cross dressing secretly for a few years. I would sneak into my mom's closet and "borrow," her clothes. I had my own apartment my parents were helping to pay for. I also had a part time job and was able to buy a few feminine clothes for me to wear. I loved the feeling of wearing women's clothes but...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Fine Tuning Ch. 02

by cathynylons on Sep 5, 2018
Transsexuals & Crossdressers

The next morning, after putting on my bra, pantyhose, and pumps I went to the kitchen and found a note from Dominique. In the note she apologized for calling me names and for being harsh with me, explaining that she was simply jealous that Tommy considered me a better cocksucker than she was. Dominique said in the note that she would make it up to me that ev...

The Awakening of a Sissy Pt. 04

by sissyjolie4u on Jan 27, 2020
Transgender & Crossdressers

After a long evening of studying, practicing, and of course grooming myself, I woke to a message from Mistress. The message read; Sissy Jolie, douche your pussy, bath yourself, and be ready to meet. Make sure you douche and your trainer is inserted. I'll be over around 11 and I expect you to be in matching bra, panties and your heels. Also, ensure your cocks...

The Ex's New Toy

by Urtoy2be on Sep 15, 2017
Fetish

A special thanks to Camilla for helping me realize my hidden desires and giving me the courage to put them into words. This is a story about fantasy but based on actual people. Some events are real some are wishful thinking. I hope you enjoy. As always comments are welcome and appreciated. ***** I am a divorced man of sixteen years. I still see my ex-wife...