100 Years in Purgatory

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O.G. enjoys his time in purgatory.
1.7k words
4.2
40.2k
31

Part 1 of the 9 part series

Updated 06/08/2023
Created 02/21/2017
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Greetings one and all, I am JT, short for Jon Thomas. I'm over 150 years old. As a mortal I worked for enterprising ladies who sought to sell their most personal and private possession. I would coordinate, facilitate and if necessary intimidate on these ladies behalf. I worked the streets in London England, in Brothels of the old American west, and finally in a 20th Century Cathouse in a southern state in America, where my life ended abruptly due to three gunshot wounds to my upper torso.

I thought of myself as a personal assistant. Unfortunately, when I arrived at the pearly gates Saint Peter called me a pimp and sent me to purgatory. I've been stuck in Purgatory for the last ten decades. In order to redeem myself for having taken advantage of these poor delicate flowers and earn my way into heaven I have served as a protector for sexually adventurous women, ensuring that they are kept safe while they seek to satisfy their carnal cravings.

~~~

Let me tell you, I have seen some freaky stuff. Lately I have been watching over Sharon. She had been a loyal and faithful wife, dedicated to her husband during her marriage. Less than a year ago she and her then husband won a modest sized jackpot from their state's lottery. A week after they received the payout from their lottery company, her hubby Ken, announced that he was leaving. Once she got past the sting of being summarily dismissed by her loving husband, Sharon admitted to herself that marrying Ken while they were still in college was a mistake. After ten years of unfulfilling sex during her marriage she was ready to make up for lost time. She packed up and moved to the big city, where a few people she knew from her college days now resided. She found a flat in a trendy area populated mostly by professionals.

~~~

To my surprise the sweet and faithful Sharon jumped right into the deep end of the pool. For the first time in her life she could indulge in her favorite guilty pleasure in all its many dimensions. She had loved them since she was first introduced to them in her freshman year of University. Sharon had been a 19 year old virgin at the time, and it was love at first sight.

As a result of marrying so young, she did not get to truly explore the wonderful world of cocks.

~~~

My assignment is to protect her through the period of her sexual awakening, once she has completed her season of whoring and transitions to or more traditional sexual behavior I will move on to a new assignment. Sharon has a goal of having the sexual experiences she would have had if she had remained single in college and throughout her twenties.

Shortly after she started her new job, I found myself perched on the wall of a car park on guard duty while Sharon was in the front seat of her car blowing the guy who made deliveries to the doctor's office that she worked in.

Less than two weeks later I worked the front counter answering questions from a couple of prospective customers, while Sharon was on her knees in the small space that served as the umbrella shop owner's office giving him head. She is still considering getting a tattoo on the side of her neck that reads, 'I give head'.

During the month after that incident she had several fuck sessions with a guy that she knew from college. Honesty compels me to report that he had a big cock, not that I was interested in that but for the sake of the story I have to report the facts. She had a sore pussy for a few days after each time she was pounded by the guy.

Sharon thinks about sex, desires sex, pursues sex and is generally interested in sex as much as any man I've ever known. She even surprised me with that bondage thing I saw her get into the other night. I mean nipple clamps, clothes pins on her pussy lips, hot wax dripped on her, being blindfolded and tied to the bed spread eagle while being double penetrated by a cock and a toy. I couldn't bear to watch. I just hoped her screams were of pleasure and not of pain and that she doesn't have any permanent scars.

~~~

I'm not allowed to have sexual contact with any of the women that I protect. But I am permitted to shift into the human form of my choosing and interact with anyone around them at the time. Many of the ladies that Sharon knows and socializes with are equally as sexual as she is. As you might expect I've found myself in some pretty interesting situations and yes I will admit it I've fallen into a lot of pussy by hanging out in her general vicinity.

~~~

At a recent party it was a fun time for all involved, I had assumed human form and kind or sort of got distracted by a petite blonde, but there's no need to get into all of that, the point is, someone turned on a cell phone camera while Sharon had a guy's cock in her mouth and and that put me in deep trouble with my purgatory parole officer for allowing this to happen.

It took me a few days of shape shifting to find the guy who was trying to shake her down for money in exchange for not posting the video clip on the internet. The gentleman was friends with one of Sharon's best girlfriends which was disappointing and so I had to teach him a lesson on loyalty. I shifted in to my six foot four inch self and stepped to the guy as he walked along a dark and empty street. I was dressed all in black; I wore a 2 carat diamond pinky ring and I carried a cane that had a brass lion's head on top of it. I looked like a bad-ass if I do say so myself.

The guy was startled to say the least, as I towered over him I bared my teeth and exposed my two inch long k9 teeth and asked him nicely to dispose of the video, and I informed him that I would cut his nuts off and drink his blood if I were to find pictures of Sharon sucking cock posted on the internet.

Sorry for going off on a tangent. The petite blonde I chatted-up was named Ashley. She's five foot two inches tall, with perky tits, a round ass and she's very physically fit. She has a bubbly personality and in bed she's as nasty as it gets, period.

The first time I talked with her, I noticed that she was as confident as any woman I've ever been around. I later found out that her confidence was born from the fact that Ashley had the deepest pussy I've ever experienced. I don't mean to brag but I'm sporting nine inches of steel between my legs, and this five foot two inch Minx was able to take me balls deep while smiling broadly and asking me if that's all you got.

~~~

Anyways, I will get back on the subject of Sharon. Recently she picked up a new beau, and this particular guy should give all of you smaller guys hope, he is at best packing a 5 inch sausage and less than 5 inches of girth, yet he has been able to have Sharon climbing the walls. I've never heard her moan and groan and scream and holler as loud with anyone as she has with 5 inch guy. He seems to have unlimited stamina, he's gets her in every position and his expertise with his cock is only surpassed by his expertise with his tongue. And he's adventurous, as they have fucked in the back seat of his car outside of a nightclub, just for the fun of it, they even went to the only drive-in theater in town to fuck. She enjoyed him so much until I actually had to remind Sharon on a couple of occasions that she should not get hooked on any one guy.

~~~

Her latest guy is into The Swinging scene. I expected this was going to be a challenge for myself since I would be thrown into the mix with a bunch of horny swingers and I knew that my big cock will be in demand.

I knew it would happen and it did, at a party Sharon and I attended I was approached by an older couple, the older gentleman a man in his late fifties asked me if I would spend time with his wife while he watched, and being the generous guy that I am I said yes. This led to one of the more interesting experiences that I've had. Throughout my encounter with his wife the gentleman was sitting in a chair with his glass of cognac in his hand and an unlit cigar in his mouth. He was talking with his wife, giving her instructions and asking her how she felt as I kissed her, caressed her, sucked her tits nibbled on her neck and fingered her pussy. He seemed as excited as she was with the prospect of me putting my cock into her. When the moment of truth arrived I move between her legs, she moaned and squirmed and he spoke excitedly, asking her how it felt, how good was it, was it big enough and encouraging her to take it all.

Meanwhile Sharon experienced Her first threesome at this same party, or as it's commonly called she was spit roasted. Sharon has proven to be one of the most sexual women have ever been around and I've been around a lot of them during my tenure as a protector.

~~~

Lately Sharon's interest have turned from cock to pussy, she's decided that she wants to get laid by a woman, but she's not comfortable approaching women and so it looks like I'm going to have to coach her through this one.

Of course she doesn't know that I have the ability to read people's thoughts, and I already know that many of the women within her circle of friends are totally down for girl on girl action, but the code of conduct doesn't allow me to mess with the natural order of things.

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3 Comments
skippersdadskippersdadabout 2 years ago

nice start, keep it going.

AnonymousAnonymousabout 7 years ago

This story has lots of potential, continue it.

JadestoyJadestoyabout 7 years ago
Interesting

Made me laugh

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