Helping Roommate First Time Gay Sex Story Stories

355,212 results
Orientation
Length
Source
Infinite Scroll

UpSkirt, Sitting Uppie, Downblouse

by BOSTONFICTIONWRITER on Sep 12, 2017
Exhibitionist & Voyeur

UpSkirt, Sitting Uppie, and Downblouse Paradise Heterosexual man pretends to be gay for voyeuristic pleasure in seeing an endless parade of panties, bras, tits, and pussies. It took me a while but I found a loophole in the sexual nonsense that exists between men and women. Here I was all these years unsuccessfully trying to pickup women in bars to have sex...

Almost Pt. 01

by danoctober on Sep 18, 2017
Romance

There are times I wish I were a child again. That place where blind innocence and unconditional trust of family and friends was the norm. No troubling thoughts or confusion of the mind. A beautiful state of ignorant bliss. But with that great desire to be a grown up and do all the things adults do, we run in haste to discard our childhood tranquility. And wi...

The Bar

by Seurat on Sep 1, 2017
Humor & Satire

Just another in the long list of diversions which keep me from finishing things I have promised. This time around, my sarcastic nature got the best of me, and I decided to take a look into the world of the characters in the stories some of us like to read and write. What do they do when stories aren't being written? No sex, not really erotic, and meant to b...

Cross-Dressing, Gay & Lesbian Sex 01

by SusanJillParker on Sep 13, 2017
Transsexuals & Crossdressers

There are no underage characters in this story. All characters are over the age of 18-years-old. Cross-Dressing, Gay & Lesbian Sex 1 Sometimes wishing he was born a woman, Daniel struggled with his need to cross dress. With his hands resting on her dressing table and his body leaning in for a closer and more critical look at himself in his wife's lighted,...

Fashion Show Backstage

by Hornyman69WithU on Sep 1, 2017
Group Sex

I dated this knockout gal for about 6 months when I was in college. She lived with her parents in my hometown, and I lived in the other end of the state where I went to college. I've written several stories about her already here—"Feeling Kind Of Lucky," about meeting her at an outdoor jazz concert, she having her first group sex with me and my roommate on H...

You Have to Pay the Piper

by donaldelliott11 on Jun 1, 2020
Fetish

Until about three months ago, everything in my life seemed close to perfect. Julie and I were approaching our third anniversary and had started to talk about "the last big step". That's what she called parenthood. So many steps to becoming a "grownup": college, shacking up, getting married. But you're not all the way adulting until you have a child. Adults h...

Gay for Candy

by BuckyDuckman on Jun 19, 2018
Novels and Novellas

It was the darkest secret Ashton had ever kept and knew he had to tell his girlfriend. Candice deserved to know he was a poser and a liar. The couples only camping trip felt like a good time to him. They would be away from the regular world, lost in the woods and surrounded by their best friends. Ashton and Candice followed behind Jared and his girlfriend....

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

Couples Only: Glory Hole Night Ch. 04

by married40scouple on Jun 16, 2020
Transgender & Crossdressers

Hi All, You don't need to read the previous chapters to understand what is happening, though it would be nice. Really, though, this chapter is about how two male roommates were invited to a party and how their lives changed after that very special party. I hope you enjoy. Feedback is always exciting and I greatly appreciate all your comments. Please enjoy, v...

Saving Savannah

by MTL17 on Sep 19, 2017
Celebrities & Fan Fiction

Author's note: This is a story based on Hellcats. Both the actresses and characters are over 18. * "Get that girl a hurricane and keep them coming." Marti Perkins grumbled as she heard Lewis's voice in her head yet again. Why couldn't he just have said 'get that girl a hurricane' or just 'get that girl a beer'. That would have loosened the brunette up....