Gay Sissy Femboy Stories

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Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

Deal with a Demon

by wolf_hunt on Jan 7, 2019
Gay Male

Author's note: Story contains Male on Femboy, a femboy getting his butt fucked and of course a femboy sucking some male's cock. All characters are 18 or older. Also this story takes place in Phoenix Cinder's universe and I do have permission from the original author! Check out her profile on here. ***** Music blaring. Windows down. Wind through my hai...

The School Ch. 02

by NeighbourhoodSuccubus on Oct 15, 2017
Gay Male

Zamuel couldn't wash away the bitter taste of Tulis' sperm no matter how much he washed his mouth with water and was set up to endure it for the ceremony when he went up a set of marble stairs as loud clacks of someone running in heels came from behind. "Hey, wait!" He stopped and turned to see a curvaceous femboy in stockings, red high heels, a loose rose...

Alix the Unexpected Guest

by BiGringo on Apr 15, 2020
Gay Male

First, I'll introduce of myself; mid 40s married bisexual, I am able to work remotely so I stay in Mexico during the winters while renting an apartment on a small island and travel back to the USA for meetings every 4-6 weeks. What I am sharing with you is a true encounter. This is the follow up from being seduced by the young Mexican elementary teacher....

A Femboy in the Wall

by Eastwood on Dec 15, 2019
Gay

DISCLAIMER: I am rewriting this story because I have now learned to use "link chapters". The other story was a mess, and now I'll be able to organize everything and keep writing. UPDATE: now we will have arts to represent certain scenes! Like this: (To clarify, I'm just taking art already made and drawing our protagonist over it and making some ch...

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Incubus

by kalanac on Jul 14, 2017
Gay

You stand in the formless void of hell, having been summoned by your master. You recently got promoted above the rank and file demons that **** the unlucky denizens of this infernal realm. "Are you ready to go into the mortal world?" a voice booms from the darkness around you. "I am, my Lord" you say. You've worked hard for this promotion...

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Damaged Goods

by NRMathis on Dec 10, 2018
Gay Male

For about the twentieth time, I seriously considered getting up and running away while I still had the chance. The only thing that stopped me from escaping the restaurant was the fact that if I did, I would be blowing this Scott guy off. I didn't even want to be on this blind date, but everything happened so fast. Kaleb, one of the men working with me at C...

A Birthday Femboy's Night Out (Now Public)

by meris on Nov 4, 2016
Gay

My name is Samantha. I wake up in the morning feeling very excited, today is my Birthday and I have very special plans for celebration. I step out of bed and take a look in the mirror, my dark brown hair gone frizzy from yesterday’s antics. I can still feel that guy’s hand gripping a big handful of my hair as he railed me. I giggle musically to myself at the...

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Fuck You Dad Ch. 02

by Nasties on Sep 28, 2020
Gay Male

***This story continues where 'Fuck You Dad Ch. 01 left off*** ***All characters are 18 years or older*** The next morning I woke up, feeling satisfied and happy whilst trying to remember the feeling of having a cock up my ass. I got out of bed to go for breakfast and I put on the same cum stained pants from the day before. As soon as I dad sees me, he tel...