Mature Teaches Twink Gay Sex Stories Stories

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Infinite Scroll

Art's House

by Collegekid69 on Jul 10, 2018
Mature

I lied in my bed, flipping through one of those gay "dating" apps on my phone while feeling my morning wood under the covers. It was 10 in the AM on a bright summer day and my mind was relaxed knowing that I didn't have to worry about any more school stress. On top of that, this was my first summer with my own car, so while I wasn't on a campus full of horny...

Silver Fox & Barely Legal Twink

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

Jim O'Connor was straight as a board. The 60 year-old with the crew cut white hair and stubbly face voted Republican, owned several guns, drove a Dodge Ram pickup, and was a retired high school teacher & baseball coach. In fact, the married father of two adult daughters with four grandkids had amassed 19 consecutive winning seasons as head coach. His record...

Treality Stories Vol. 02 Pt. 01

by RocketmaninOz on Apr 22, 2020
Mature

Treality Stories Volume II - our adventures in love continue: an introduction All characters are well over 18 years old and include 'Rocket Man' and 'Sparkling Red' who first met online a few years ago as their alter egos 'Jardine Man' and 'Mimbabe'. Goddess Rule 2 .I want Genie wrapped around your pulsating penis Mojo right now coming with him on That Sp...

Epiphany At An Epiphany Party

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

Author's note: This is an note to self I am sharing. There is no sex but lots on my own sexuality. I love adventure, but my wife only needs the traditional needs. She knows nothing about any of my sexuality adventures and would divorce me if she did find out about one of the hundreds. ** Dancing with Ladies ** I swing dance socially. I am used to going up...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Total Drama Femboys

by nddd on Apr 29, 2025

In our current reality, the Total Drama ladies are... what they are. Hot and sexy babes that participated in a reality show that got them fame and sex as well. But what if, there's a reality where they are... femboys. A male possesses the body and curve of a female along with their feminine charm that they can be mistaken for female. And these femboys retain...

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Birds & Bees

by Svenskaflicka on Sep 16, 2017
Reviews & Essays

Literotica has members and readers from all over the world. Thousands and thousands of people, from different countries, with different laws and different cultures when it comes to sex. Some members live in places where a woman must remain a virgin until she gets married, others in places where you may have sex as early as at the age of 15. To avoid any prob...

Randy for Submission, Pursuing the One

by BrokenBoundariesGayErotica on Jun 10, 2025

Chapter 1: The Hunter © Broken Boundaries Gay Erotica In the dim, battered apartment on Sherbourne Street, the walls pulsing with the muffled heartbeat of the city beyond, Randy’s body moved like a machine — relentless, efficient, unfeeling. He drove his hips forward again, burying his thick cock deep inside the slender twink sprawled beneath him. The boy so...

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Postscript: The End to PIG

by fexhominum on Jul 27, 2020
Fetish

Goddess Ashley met me outside of a Panera Bread for the ostensible reason of returning my credit cards to me. She was sitting alone at a small table, drinking a mango smoothie. She wore a white halter top, black shorts, and white high-heeled sandals. Sunglasses stylishly perched atop that luxurious blonde hair. As I approached, I could see her ruminating on...

Cocksucker: Cum Bucket

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Shemale and others gangbang straight crossdressing anal virgin. You do not need to read the first parts to enjoy this story of a straight man's hotel orgy of gay submission. In case you are curious how this straight married man got into this predicament, here is a brief summary of the first three chapters of "Cocksucker": Chris, a married straig...