Mature Teaches Twink Gay Sex Stories Stories

248,269 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

Cuckold & Netorare Shorts

by grimbous on May 17, 2019
Cheating Spouses

Hello Readers, What follows will be random Cuckold related short stories, set ups, or scenes. I get a lot of cuck related story ideas that I need an outlet for. This is simply a place for me to collect some of the ideas I get from time to time to see how they go over and gauge what is popular and what isn't. Don't expect lengthy or overly involved tales. Do...

Open in Reader

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

Open in Reader

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...

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...

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...