Sissy Shy First Blowjob Story Stories

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A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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Center of Attention Ch. 02

by Seethru57 on Sep 16, 2017
Group Sex

Disclaimer: All characters in this fictional story are 18 years or older, and all names are ficticious. This is a continuation series. Debbie Ross was sitting on her bed, writing in her diary about the events of the previous night. She wanted to keep those memories, and hoped to add new ones to the lusty events at Mr. Collin's home. Her thoughts were interr...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Harem Master

by Callum95 on Aug 11, 2020
BDSM

You are the leader of the harem in which you can order your harem to ride that big fat cock of yours or do something else like recruit another member or get a job so you can have more money. To your harem, you are god. You can do anything. Now i am going to try and be consistent with adding chapters as im going to focus on 4 characters. 3 of them will be har...

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My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

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...

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...

Starlit Petal Ch. 01

by Certeis on Mar 21, 2018
Transsexuals & Crossdressers

NOTE: this story is an original setting, but anything you need to know is discussed in the story text. *** 'Swshh' 'swshh' 'swshh' Petal's legs moved back and forth rhythmically, the nylon stockings rubbing against each other at every pass. They were dangling in the air above him as he laid on the padded bench and read a book. Well, pretended to read it, a...