Stories published by Boss01

7

Boss01

The Wages of Sin-Part 4

The trouble two young ladies will get into left to their own devices...

This is Part 4 of a continuing story. One should really read Parts 1 thru 3 to get the full grasp of this one. I had just spanked 18-year old Erica and then taken her virginity while 19-year old Meredith, her fellow Acolyte who I had spanked and fucked the week before, watched. Erica had actually complained that I had given more sexual attention to Meredith than her, and I had promised to...Read On

13

vote

Boss01

The Wages of Sin-Part Three

Erica wants the full experience...

This is part three of a series. I suggest reading “The Wages of Sin Parts 1 and 2” first. It was the following Sunday. I was standing outside the Acolyte Room waiting for Erica and Meredith to get done changing. Meredith and I had some “disciplinary matters” to “discuss”. I could hear them talking, and was about to knock to see when they would be out when I overheard… “So what happened?”...Read On

11

vote

Boss01

Cuffed and Stuffed, Again

mf, handcuffs, tied up, police, younger woman, older man, hand job, cowboy, oral sex

For this story to make sense, I urge you to read my story “Cuffed and Stuffed” first. Thanks! “What is it with men?” she lamented, as the bartender set our drinks down; she being Sandy, a former trainee at the police academy where I am an instructor. “Why do they think that they always have to make the first move?” Sandy and I had become friends when I was her instructor at the academy,...Read On

19

vote

Boss01

Cuffed and Stuffed

Sandy takes control

At fifty, I decided that it was time to retire from my part-time law enforcement career. My biggest concern was keeping my certification from going to inactive status. Fortunately I had made friends with the director of the local police academy, who clued me in to the fact that instructors at the academy were granted active status on their certification from the state. While I wasn’t able...Read On

10

vote

Boss01

The Wages of Sin-Part 2

Meredith's turn...

I recommend reading my story titled “The Wages of Sin-Part 1” first… I had just delivered thirty with the belt across 18-year old Erica’s clothed buttocks for stealing wine from the church, and had experienced an erotic reaction the likes of which I had never had before. Now, I had turned to 19-year old Meredith, the instigator of today’s theft and previous others. I was still aroused from...Read On

11

vote

Boss01

The Wages of Sin - Part 1

Erica goes first...

“Gotcha!” I said to myself in satisfaction as I reviewed the video feed from the security camera. “Gotcha, indeed!” As the lead Verger at an Anglican-rite church, one of my duties was being the de facto head of the Worship Committee. A few years ago, towards the end of the summer, one of the Altar Guild ladies had informed me that they were experiencing “inventory shrinkage” in bottles...Read On

11

vote

Boss01

A Christmas Story

They came upon a midnight clear...

About twenty years ago, when I was in my thirties and had moved to Florida, I started attending a very traditional Anglican-style church. I became actively involved, to the point where about ten years ago I became the head Verger. A major part of that job is coordinating and choreographing the various aspects of the Mass, particularly the Masses celebrating the major holidays. The...Read On

19

vote

Boss01

The Throw-Away Line

Sometimes age doesn't really matter...

I met Amanda when I went back home to settle my father’s estate; “home” being a small city on the Intracoastal Waterway north of Vero Beach. Since the last time I had been back, a new pizza place had opened in a town that had more pizza places than it really needed. Their hook was “Authentic New York Style” pies, and my sister swore that they were. So after spending the better part of the...Read On

11

vote

Boss01

The Joys of Penetration Part 2

The lesson continues...

I recommend reading “The Joys of Penetration Part 1” before reading Part 2. Marty, my childhood friend, had just been the recipient of the first blow-job I had ever given. As I was reveling in the euphoria of the feeling of control the act had given me, Marty made it clear that my initiation into the joys of penetration was only half over. But first he wanted to return the pleasure I had...Read On

16

vote

Boss01

The Joys of Penetration - Part 1

You're never too old to learn

The last year that I was living in Florida, I was dating a woman named Phyllis who had an interesting perspective on oral sex. While she had no problem providing it, she wasn’t real keen on having it performed on her. As she told me on numerous occasions, her sexual preference was penetration. Vaginal, oral or anal; it didn’t matter as long as she was being penetrated. Preferably culminating...Read On

17

vote

Boss01

Beach Patrol

Strict enforcement has its rewards

I first met Nancy when I was working the overnight shift as a part-time police officer for a small ocean-side town on the Atlantic. She was sixteen, and her parents had just bought a small complex of duplexes in town. She was working at the only fast-food joint in town, and the only place in town open to get something to eat or drink after 10PM on a Saturday night, my usual shift. However,...Read On

30

vote

Boss01

The Family Rules

It's always a good idea to follow the rules...

The family of my first girlfriend in college had "rules" for everything. But, from my perspective, there were three that had the most impact on our relationship. The first rule was that the two daughters, Theresa (my girlfriend) and Valerie (her younger sister by a year) were not allowed to date until they were 18, coming from a very small conservative town as well as two very protective...Read On

26

vote

Boss01

It's Her Birthday

Disobeying the law sometimes has its own rewards

Several years back, when I was in my late thirties, I was working part-time as a police officer for a small Town on the ocean, just north of a very popular summer tourist city. Because of limited access to the ocean side of the Intra-Coastal, our town had a lot of pass thru traffic as we were at the foot of one of the major bridges that lead to the beach. The residents, mostly...Read On

23

vote

Boss01

Punishing Her Ass

A Surprising Tale of Employee Discipline

What a major screw-up. I had just learned that my young and very attractive PA, Therese, had been leaving data off the monthly report spreadsheets for the last six months. The damage wasn’t severe: but it made the office look like it was under-performing when it wasn’t. Still, my boss’ bonus was going to be affected if the reports weren’t re-submitted correctly by Monday morning, as I had...Read On

Stories by boss01