Sissy Scool Porn Caption Story Imagefap Stories

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Infinite Scroll

Crossing the divide

by reaper13 on Dec 3, 2016
Interracial

It’s all messed up. During the run for the white house tensions between races in the US have been escalating. Arabs are being profiled, Asians got accused of faking climate change, unarmed black men got shot by police, Mexicans have been called rapists and native Americans protesting in the freezing cold had water cannons used against them. What is this coun...

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The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

A New Life Ch. 03

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

"Click on this link, sissy. I want to show you something," Mistress Sally said. And I happily followed instructions believing it to be some aspect of sissy porn like a caption, or little GIF video. I couldn't have been more right...or more wrong. My newly painted red lips parted in shock as my computer opened a new browser that showed what seemed to be an a...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

My Friday Night: Disconnected

by honey28 on Sep 16, 2017
Transsexuals & Crossdressers

Although it has been two years since I posted a short story, I never stopped writing. In 2012, our relationship was at its start, and I began feeling things that I was not ready to share with him yet. Those feelings were coming through in my writing, so I kept my stories to myself for a long time. I actually wrote a book, and was also busy with editing Nicho...

Wife's Exploration

by cpandy on Jul 5, 2009
Cheating Spouses

John sat in front of his PC trawling through Imagefap, his latest search for cuckold captions had uncovered a goldmine of unseen pics and his cock was stiff in his pants as he immersed himself in their delicious humiliation. He clicked quickly to those of a well built blond that paid a passing resemblance to his wife Doe. Stroking his cock through his pants...

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Teach Me Professor Ch. 02

by janey16 on Sep 14, 2017
Fetish

This is the continuation of my higher education! Please read part 1 to see how I realized that you're never too old to learn! This chapter continues to explore various themes of kink, younger-older sex, group sex, a little bit of guy-guy stuff with women watching and , of course, some pussy to pussy fun! I was finally feeling better from my hangover o...