Draining "bosses" Site:literotica.com Stories

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Interracial Cuckold With A Twist

by Samuelx on Sep 16, 2017
Interracial Love

Hamilton O'Keefe smiled to himself as he thrust his cock deep inside Michael Voltaire's asshole. The big and tall Black man squealed as the young Australian slammed his twelve-inch White dick deep inside of him. Nothing a bisexual stud like Hamilton loved more than fucking Black male ass, except maybe fucking Black female ass. Holding firmly onto Michael's h...

A Gilf's Cum Slave Ch. 02

by milfleglover on Sep 19, 2017
Mature

Annabelle Shaw eyed the gawky, skinny nervous boy bagging her groceries and smiled. The Fortune 500 CEO had just gotten out of work and had stopped at the store for a few things -- and a fresh load of boy cum if possible. And with Annabelle's 62-year-old libido firing like a woman's half her age, it was definitely possible. "Be a dear and carry these out to...

Head Fantasies Ch. 03

by boogieman10469 on Oct 15, 2017
Interracial Love

For as long as I can remember, I've fantasized about the women I've found attractive. The following is a series of some of those fantasies (at least the ones that I can remember) about teachers, co-workers, classmates, women and girls from my neighborhood, etc. Although I'll accurately describe people, places, situations, and circumstances, I will (of course...

For The Love of the Mob Ch. 05

by pyramids_96 on Dec 16, 2019
Interracial Love

It was 5 A.M when the loud vibration of Nia's phone flooded her apartment. She jumped up to turn it off and rubbed her sore eyes as Lorenzo laid silently beside her. She sat there for a moment, taking in his thick eyebrows, deep olive skin and toned body as he slept, unaware of the chaos that took place last night. For a moment, she wanted to kiss him but sh...

Corrie The Next Generation Ch. 05

by RedSox04 on Feb 12, 2019
Celebrities & Fan Fiction

Sarah Platt lay on her back, her boyfriend Gary Windass was on top of her, sliding his cock into her, she just wanted it to end, which she knew these days, wouldn't be long. It was fine at first, the sex was good without being amazing, but she was happy with that. But recently it had become very routine. Gary would slide his hand into her pyjamas and finger...

Bitch Owned

by teacherpetslut on Apr 22, 2025

Marcella Alice Polk. Almost nobody knows her full name. Her bosses call her Polk. Her small office has a nameplate on the door "M.A.Polk". Polk is a brilliant corporate lawyer. A genius loner. Loved by her firm because she has, for over twenty years, done the backroom grind with near perfect results. She is quite happy in that solitary work. Most l...

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Big Brother Boss Ch. 01

by m8cct on Nov 16, 2020
Loving Wives

"Mmm, FUCK baby, give me that perfect cock!" Riley Williams rode her husband in a cowgirl position on their marital bed, breathing heavily with her head hung back in ecstasy and a smile on her face. After waking him up with a blowjob, she decided she wanted to try to get a fuck in before they both had to leave for work. Riley was a 26 year old natural blond...

It's A Long Story

by afanofyou on Sep 16, 2017
Fetish

It's a long story as to how it came to be that I, a straight male, willingly took a fat cock in my mouth and sucked the head while rolling my tongue on the tip moments before it shot load after load of cum down my throat. I just finished sucking all the cum out and was savoring its flavor when another cock slapped my face and shot a spurt of hot, hot cum on...

Riding the Boss

by Brian70 on Nov 1, 2017
Transsexuals & Crossdressers

Tonight wasn't a spontaneous, spur of the moment act. Tracey, a close 'girlfriend' had really wanted to go out dressed. The more she talked about it the more I was in. We often dress together but it has always been at her place or mine. We have never gone out dressed. Our neighbors haven't seen us either as far as we know. We decided to go to the C & C ABS....

Intern Affair

by Decayed Angel on Sep 15, 2017
First Time

Feeling the last of the pulsations flow through his cock, the last bit of cum draining deep into Tonnie and the inevitable shrinking of his manhood he couldn't help but think, "I've failed her again." As he caught his breath, his cock slipped out of her wet, unsatisfied cunt and he groans, "I'm sorry Tonnie." Sliding off him, she quickly straddles his thigh...