Ssbbw And Sissy Stories

33 results
Orientation
Length
Category
Source
Infinite Scroll

My High School SSBBW Stoners Ch. 02

by completeexperience on Sep 16, 2017
Romance

Debbie seemed to be in a very deep sleep, and having just smoked the equivalent of about two blunts in less than an hour, after smoking no weed for two months, I concluded that she probably wouldn't wake up for several hours. So I decided to explore my humongous new girlfriend, who I first saw just three hours earlier. First I lay her on her back, then roll...

My High School SSBBW Stoners Ch. 01

by completeexperience on Sep 14, 2017
Romance

After finally getting her newborn daughter to sleep, Debbie sat nude on a couch in the living room and lit a blunt, her humongous ass sinking several inches into the cushion while her 50DDD knockers hung down and rested on her belly. Seven days earlier, she gave birth to her first child, just two months after she graduated from high school. Having not yet f...

Black Journal Ch. 15

by Dhc000333 on Sep 14, 2017
Erotic Couplings

Duncan Cyrus, age 23, Back Home So, I moved back home to my parents' house. That was short lived because I needed my own place. I had saved up for such an occasion. Within a month I was in a new apartment and my pops had set up a job interview for me with an associate at a fauna and flora laboratory just outside the city limits. Basically what I do there i...

SSBBW - Natalie G

by mondotoken on Oct 22, 2019
Erotic Couplings

I knew I's been going through a rut since breaking up with a cheating girlfriend two months earlier but didn't see anything wrong with a spartan lifestyle until Walter, a good friend at work took it upon himself to conduct a one man intervention. He approached me in the cafeteria during my last break. "Hey man; can I ask a probing question?" "No." "You ge...

My High School SSBBW Stoners Ch. 04

by completeexperience on Jun 15, 2020
Romance

As I hung up Debbie's phone, I set it on the nightstand, lay on my side on her left, and gazed at my extraordinary new girlfriend. Having lost both her cunt and ass virginity on the same day, while smoking weed heavily after having none for two months, she was exhausted and looked like she would be asleep for several hours. It was now 11:30 PM and she had sc...

BBW Shows Off for Captive Admirer

by TXssbbwGODDESS on Sep 14, 2017
BDSM

A story about a SSBBW, or very large woman, who takes control of a pesky internet chat-room player and taunts him with what he wants but cannot have. The story is told in her perspective. It contains mild bondage, exhibitionism, voyeurism, denial teasing, and fat admiration or "FA" themes. When things get slow at work, and I'm the only person in the office...

My High School SSBBW Stoners Ch. 03

by completeexperience on Nov 19, 2018
Romance

Then Debbie's phone rang, waking her up. "Do you need to get that, Honey?" I asked. "Yeah, I probably should! It's probably my mom wondering what the fuck happened to me!" Debbie responded. As I stood up, she rushed over to her shorts, grabbed her phone, and enthusiastically exclaimed "Hi Mom!" "Hi Debbie!" I heard a fairly gravelly but feminine voice res...

Actions and Consequences Pt. 06

by Shadowforce1 on Jan 6, 2020
Mature

"Next pose," the photographer said. I laid down on the lounge chair by the pool with my legs folded over each other and leaning forward, dropping my heavy hangers down for him to take a few pictures of me. Then I switched again following the routine of the three other women that had come before me. Eventually, I got into the pool and came out slowly. Eac...

Tootie

by mrpeachesva on Dec 17, 2017
Fetish

It was a cold Thursday night in January and the three friends were watching a NBA game. They were all in James' apartment but they all lived in the same apartment complex, the Northhampton in Largo Maryland. The Knicks were playing Chicago and they were getting blown out so far. It was only the middle of the second quarter and the score was 46-26. "Your boy...

The Bet on the Biggest

by dirtyjoe69 on Sep 12, 2017
Toys & Masturbation

I am a big woman; some would call me a SSBBW (super sized big beautiful woman). I weigh, well I am not going to tell you what I weigh but let's just say it is more than the average Joe can lift. I have a massive chest; each boob would cover most people's heads. And I have been cursed with two gaping holes. Both my wide asshole and my gapping cunt can easily...