Mature Boss Stories

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Mature Touch

by sexystacy on Sep 12, 2017
First Time

Joe was in the storeroom at work, cock in hand. He had just had a date with his girlfriend Maria. She had played little Miss Cockteaser again. She invited him to her room, but would only let him watch as she fucked herself with a big pink dildo. Now, the 18 year old was jacking his cock so hard, imagining the tightness of Maria's pussy. If he didn't shoot hi...

Off Broadway Public Theater Pt. 02

by TonyMA70 on Mar 25, 2019
Mature

Stacy drove home from the second rehearsal presented to the backers who decided to bankroll the production, after some debate. She contemplated how she will approach the subject when her husband asks her about the nude scene. The mature woman parked her car in the garage and went into the house. Her husband was waiting for her. "How was the rehearsal tonig...

Sexploits Ch. 06: Rene

by dpingjessie on Sep 18, 2017
Mature

Five years ago, I received a phone call from a woman, whom I will call Rene, to set up a job interview with me for a position she had open in her department. I met Rene a few days later in her office, and if you had told me then what this woman would be to me just four years later, I would have never believed you. At the time, I was just looking to land a jo...

Reconnecting with Rene Pt. 02

by dpingjessie on Sep 25, 2017
Group Sex

About three months after I fulfilled one of my wildest fantasies by fucking Rene, the older woman who had been my boss for almost three years, I had the courage to share with her an even wilder fantasy of mine, albeit indirectly. I had posted a story that depicted my dream of having sex with my older supervisor in her office more than a year before we actual...

Short Order Troll

by MarshAlien on Sep 17, 2017
Non-Erotic

This story was inspired by, and is dedicated to, the luscious SweetWitch. The part of the troll was played by actual anonymous public comments. I took a quick glance at the clock. Eleven-thirty. Half an hour 'til closing. God, it had been a long day. Normally, I would be pretty much done at the grill by now, and I'd be helping Cherry wipe down the counters....

Mature Woman Has Her Way Ch. 04

by Panty_Licker on Sep 19, 2017
Mature

"Go home. I will contact you later." I read it again and again but the short note didn't change. I was confused when I woke up and found that I was alone. The indentation on the pillow beside me proved that I hadn't slept alone. Maybe I had upset her, but the faint tingling in my asshole coupled with the memories of the previous night made me think otherwis...

Guardian Angel

by HarryOrwell on Sep 13, 2017
Mature

She was outside the bar, fumbling with her carkeys. She kept dropping them, clearly too drunk to drive. She was 50ish, 5'4, stocky, with blonde hair, disheveled, make-up run-down, wearing a tight skirt/suit. The light rain had soaked her through, and she was shivering. 0bviously, a business woman who had a few too many after work. I had downed a few myself...

Vice The Trickster

by Samuelx on Sep 21, 2020
Interracial Love

Gutierrez Janitorial Services, whose office lies in a seedy neighborhood not far from the Saint Laurent Mall, is one of the largest cleaning companies in the City of Ottawa, Ontario. They compete with Aramark and GDI and the other big shots for access to schools, labs, shopping centers and Canadian government buildings. The owner, Marisol Gutierrez has a com...

Rustic Pleasures

by cafealamabel on Sep 12, 2017
Interracial Love

Last quarter audits at the various banks and credit unions in the area had Joyce Froehty fit to be tied. This was nothing unusual for this veteran Compliance Auditor of twenty-five years, but since she was approaching 50 years old on her next birthday, she realized her dwindling endurance for long-term audit marathons deserved a well-earned break. The Steph...

My MILF Boss

by xratedstoriesx on Sep 13, 2017
Mature

I couldn't help notice when my boss walked past. My eyes were instantly drawn to her long smooth legs under her slim-fitted pencil skirt, then up to her round, juicy ass, then further up to her large, perky breasts concealed behind her tight, low-cut blouse and finally to her gorgeous face. Ms Jessica Reyland was older than me; she was in her late thirties w...