100 Years in Purgatory Ch. 02

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Tem 23, 2022 // By:analsex // No Comment

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Since I’m sharing the story of one of Michael Jones, who likes to watch other people have sex, I thought I might allow the readers to watch and listen along with he and I as the narrator tells the story of his widowed wife having her first sexual encounter after her husband’s demise.


Jon Thomas speaking; I was recently called in to see the old man; he had a special assignment for me. Seems this fellow, Michael Jones had just arrived in purgatory and I was to show him the ropes.

Old Mike had gotten his nuts in a vice for being a voyeur, and St Peter’s twisted sense of justice thought it might be a proper penance, to have Michael watch his widowed wife’s sexual encounters.


Michael my man, it’s a pleasure to make your acquaintance I’m sure, I said reaching out to shake his hand. Hi, said a very uncomfortable looking Michael. Oh, I get it; you can’t believe you got busted spying on people can you? Trust me St Peter sees everything, everything.

Don’t worry about it, we’re gonna have fun. You won’t feel any pain or jealousy, but you might be a little surprised. These women can be nasty in the bedroom, but you’ve seen that already haven’t you I snicker.

Let’s go, I said.


Jon Thomas speaking; Michael, let’s see what she’s up to, I say. Oh, and not only do you get to watch what she does, you will know what she’s thinking.


We’re at Michael’s wife’s new home, as we begin.


Katrina Zara Jones looked around her new living room and exhaled, her new furniture was delivered earlier today. The delivery men put the furniture into the assigned rooms, but her beds, dining room table and chairs, and executive desk, needed to be assembled. The television needed to be mounted on a wall in the great room. She could have paid the delivery men to do those jobs but, her daughter and son-in-law really wanted to pitch in to help her get settled. They would be arriving tomorrow and stay with her until the weekend


Jon Thomas speaking; Michael, before your twisted mind can even go there, you are only allowed to observe your wife’s intimate moments, no one else’s I chastise. Even I have my limits.


She walked out onto her deck to take in her new surroundings, her yard was huge, there were trees and grass and nature all around her, she had moved into a more rural setting than her previous neighborhood. There was more privacy, especially at this time of year. The leaves on the trees formed a natural barrier to the houses on the street behind her home.

Night fell and Katrina spent her first evening in her new home, and for the first time in a year she didn’t feel the pain of her loss as intently. Now she was in a new house, outside of the city, she was starting over at the age of 63. She had spent the last five years caring for her ailing husband, when he realized that his body would not be able to survive the effects of diabetes he made her promise to not waste her life grieving.

He granted her one year for grieving, and made her promise to find a new lover as soon as their agreed time-period ended. Yesterday was the one year anniversary of her husband’s death.


Jon Thomas speaking; my condolences for her loss that was a nice gesture buy you Mike and I patted him on the back.


Sunday afternoon, her daughter and son-in-law were gone. She was all alone now, no concerned neighbors who would drop by to check on her, no members of her church to call on her. In fact she didn’t really know a soul here. There was only one person who’d had a conversation with her, everyone else had said hello and kept it moving. She wondered if she had made a mistake, thinking she could start over at her age, perhaps she should have stayed in her and Michael’s home, and continued the life she had.

What man would want her now, her hair has really started to grey, and she then runs her fingers through her hair, not to mention what has happened to her body the last few years. Even if someone were interested, would he be an older man? Would an older man have the hard cock and stamina that she needs? She couldn’t imagine being with a man who couldn’t satisfy her. The one thing that hadn’t suffered was her appetite for sex. Cat truly loved cock and all the wonderful things they can do.

It had been two years since she and Michael made love for the last time. But it had been much longer than that since they’d had a good long session of lovemaking, where she was able to do what she loved most of all, play with his manhood, and watch the creamy white goodness that carried his seed flow out of his penis. To her that was the ultimate proof that she had pleased him, and pleasing her man was what pleased her.


Jon Thomas speaking; Michael said can I take my fingers out of my ears yet, I didn’t want to hear that?

You ain’t heard nothing yet Michael, trust me on that one I said.


Her ringtone broke her train of thought. It was Marva, her roommate from college, calling with a pep talk. Reminding Katrina the good lord helps those who bonus veren siteler help themselves, if you want something you have to go for it. Katrina reminded Marva that she always knew what she needed to hear and when she needed to hear it.


After the phone call from Marva ended, Kat replayed in her mind the conversation she’d had with Roscoe. Roscoe had introduced himself last week when he was taking his daily Bike ride, Kat had been in her yard looking at her dreadfully neglected flower gardens when Roscoe stopped and said hello, and introduced himself. He welcomed her to the neighborhood. They made polite conversation about the pitiful effort that the lawn service hired by the property lean holder had done while the property sat unoccupied.

Before he peddled away he’d said; it’s a pleasure meeting you Kat, I live in the neighborhood, if there’s ever anything I can help you with, feel free to flag me down when I ride by.

She had watched him from a window riding by her house a few times since then.

And each time he had seen her in her yard or in her driveway, he had been keen to speak to her.

She had guessed Roscoe P Coltrain to be in his mid 40’s, attractive and fit looking. He was able to carry on a coherent conversation, albeit a brief one. He owned his own home and he was available. And most importantly, she sensed his self-confidence. But surely he wouldn’t be interested in a woman at least 20 years older than he was.

The good lord helps those who help themselves, she repeated to herself.


Jon Thomas speaking; Aw Souki, Souki now, momma likes them younger, did you know about that Michael, I asked.

Michael shook his head no.

Oh and Michael, just an FYI, St Pete knows about you watching Marva and Jack get it on when they would stay at your and Katrina’s home. That’s part of what got you into this mess I said.

Michael just made a stink face type expression.


That Sunday night Kat took her first bath in her new bathtub; she placed lighted candles on each corner of the tub, poured a glass of wine, and found a jazz channel on her satellite radio. Thank you granddaughter; for teaching me all about satellite radio thought Kat as she smiled.

After her long relaxing bath, she stood naked in front of the full length mirror in her bedroom and applied skin cream all over her body before she put on her nightgown, her hourglass figure was still there but, it was covered by an extra 10, okay 15 pounds, thank you for your honesty, mirror. Kat, said the mirror, before we present ourselves to a man we’ve got to tone up our thighs. Thank you again mirror.


Monday morning Kat was up bright and early searching for her workout gear, as she laid out her collection of sports bras, tops, and bottoms she suddenly remembered that it was all outdated and a size too small since she hadn’t worked out in over two years. She would have to squeeze into something for now, and go shopping for new outfits later today. She pulled on leggings instead of her other bottoms that were made of compression materials that would not stretch. She quickly found out that her 36-d breasts were spilling out of every 36-c sports bra she had. She would have to wear a regular bra this one time. She found and oversize t-shirt to cover herself.

She finished two trips around her sub division; power walking while carrying five pound weights in each hand. She’s committed to walking two miles, at least one time per day until her mirror stops body shaming her.


After a trip to a local department store to purchase some new workout clothes, Kat hurried back home to put phase two of her self-help plan into action.


Jon Thomas speaking; Women are so critical of their bodies, I think she looks fine, don’t you I asked Michael?

Oh yeah, she’s beautiful said Michael.

Then why did you spend so much time checking out the hot piece of ass that lived across the street from you.

Because she’s a hot piece of ass, replied Michael, totally missing my point.


Later in the afternoon Kat went outside to remove weeds from her flower garden, she purposely time it so she had been hard at work for about fifteen minutes when Roscoe rode by on his way home after his bike ride.

As she waited for him, she wondered why all of a sudden she was feeling so alive. Perhaps she felt free because of the pact she made with Michael. Suddenly a warm sensation started in her pussy and spread over her entire body. That feeling had been missing for a long time.


Her brand new gardening tools were laid out on the ground, as Kat struggled to up-root some of the weeds that had grown into stalks when Roscoe pulled up on his bike. Hi Kat he said. Hello sir she said. Kat I’ve got some good news and I’ve got some bad news, which do you want first. Kat shielded her eyes against the late afternoon sun, and then asked what the good news was. I have a new bike said Roscoe proudly. Congratulations said Kat with sincerity. Now for the bad news said Roscoe, bedava bahis you’re trying to uproot a tree. Kat blushed with mild embarrassment, and then burst out laughing.

Roscoe climbed off of his bike and laid it on the ground. Didn’t I ask you to let me know when I could help you he said sternly. Yes sir replied Kat, but I didn’t want to take you away from your riding. I have plenty of time to ride said Roscoe.

This is an oak tree; the root will be pretty deep on a tree this size, let’s dig down a foot or so and chop it off, that way it won’t continue to grow. Thank you said Kat. Let’s look around and get rid of any others we see, and if you insist on cleaning all the flowerbeds yourself you will only have weeds to deal with said Roscoe. OK said Kat.

For the next hour they removed weeds from the flowerbeds and among the shrubbery, but mostly they talked and got to know each other. they mostly talked about their current situations, and more than a few times Kat noticed that Roscoe had looked down the over-sized shirt she was wearing over her Capri pants. She had worn one of her 36-c sports bras underneath her shirt with the intention of giving him a good view of her best assets whenever she bent over.


They were both widowed, him to a car wreck, and Kat to complications from diabetes.


When the weeds were all gone Kat, apologized for taking Roscoe away from his hobby, and then offered Roscoe a firm handshake and said thank you for rescuing an old lady who couldn’t tell the difference between a weed and a tree, then she smiled sheepishly. Roscoe replied; I enjoy working in my yard, so that was OK, and I enjoyed the company of a beautiful, and he stressed the word beautiful woman. She looked into his eyes and then asked if there was any way she could repay him for his hard work. Roscoe hoped she was flirting, but he responded with an offer to cook dinner for Kat. Just give me a day’s notice he said. Kat accepted his invitation, saying I will let you know once I check my calendar. See you tomorrow she said with her voice trailing away. I think so he said as he stepped over the crossbar of his bicycle.


That night Kat called Marva to tell her that she had a date. Marva was genuinely happy for Kat, and she wanted to hear every detail of their conversation this afternoon while they cleared weeds from the flowerbeds.

When Kat told Marva that she intentionally allowed Roscoe to see her breast, Marva congratulated Kat, and told her that she was proud of her, and that she knew that Kat still had some whore in her. Both women laughed themselves to tears.

When they regained their composure, Kat asked; we really were whores back in college weren’t we? Speak for yourself laughed Marva. You loved cum as much as I did Kat said. I’m not sure if it’s possible for me too love cum as much as you do said Marva with a laugh.

Michael is the only man who’s ever known that I loved it and even he wasn’t aware just how much I loved it. Now I’m unsure how to initiate that conversation with a new man at this stage in my life. I’m not even sure if I can still pull a man for that matter. I practically threw myself at Roscoe, showing him my breasts with that tiny bra I was wearing.

You will have to figure that one out said Marva.


Jon Thomas speaking; Michael the expression on your face is priceless, you had no idea did you, you thought you were the freaky one didn’t you? You know she’s going to give that hunky bike rider some pussy, don’t you I tease him.

Michael had this wry smile on his face. You dirty dog, you want to watch her fuck.

I’m beginning to like you I say.


After taking a bath for the second night in a row Kat is back in front of her mirror to put creams on her skin, but before she does she looks very closely at herself. She wonders if she should try a new hairstyle, she’s had the same one for years. She studies her face, her skin still looks youthful, but to be honest her laugh-lines are prominent and her jaw line isn’t as firm as it once was. She looks like a mature woman but not an old one.

As she studies her body she is pleased with her breasts, what man wouldn’t like to play with these beauties she thought. Her thighs and ass are carrying most of her extra weight and she has vowed to do something about that. She rubbed her hand over the thinning patch of curly hair covering her sex. I should trim these so it looks cuter she says to herself.

When she slid a finger along the crease between her folds, she imagined Roscoe’s fingers touching her there. She watched herself in the mirror as she started to rub her clit in a circular motion, and she cupped her breasts with her other hand. She rubbed the length of her slit and used four fingers to manipulate her entire pussy, before sliding two fingers into her already wet hole.

She fingered herself, played with her clit, and massaged her g-spot. Her head was thrown back and her eyes rolled up as her pleasure increased. As she got closer she started fucking her pussy with three fingers, her knees deneme bonus bent as she got closer, she finally lay down on the floor and brought herself to an orgasm.


Jon Thomas speaking; Damn, she needed to use three fingers to replace you Mike, color me impressed.

Why didn’t she do that for me when I was alive, asked Michael?

Did you ask her to do that for you I asked?


Kat didn’t miss a morning workout all week; she now had the extra incentive of making her body as desirable as possible.

Roscoe stopped and chatted with Kat every time he saw her outside when he rode past her house. He wanted to see her more, but he didn’t want to come on too strong.

The more Kat saw him the more difficult it was to suppress her desire to please him.


By the end of the week Kat was feeling so good emotionally that she decided to sleepover at a girlfriend’s house on Saturday night and attend church in her old neighborhood on Sunday. She knew it was time to have a talk with Roscoe.

She had not committed to a date to have Roscoe make dinner for her; she didn’t want him to pamper her until she had explained her predilection to him. She could handle that conversation better emotionally if it happened at her place.

She was outside in her yard on Thursday waiting for him to ride past; she busied herself by inspecting the job that the lawn service had done when they put decorative wood shavings in the flowerbeds. She was wearing a dress, and when she saw him approaching she lifted the hem of her dress slightly, pretending to be a lady of pleasure.

Roscoe turned onto her driveway and stopped as Kat walked toward him. Whatever you’re selling, I want all you’ve got said Roscoe laughing loudly. Kat was proud of herself for her clever insinuation; I don’t have anything worth selling said Kat, with a pretend sad face.

And they both laughed again

After a moment Roscoe said; OK, now that you have my attention what’s going on and how are you?

I’m good said Kat, and it’s good to know I’ve still got it, if you meant what you said. Do you really want whatever I’m selling? It’s not all shiny and new, you know.

Roscoe didn’t respond right away, so Kat spoke again. I know you offered to cook for me and I still plan to accept, but for now I would rather have you as my guest first, is tomorrow OK?

Roscoe looked into her eyes, and said of course, it’s OK. What time should I be here?

You can finish your ride and then come by after you’ve washed your sweaty behind, she said with a warm smile.


That night Kat tossed and turned and had a devil of a time falling asleep. Seeing that it was useless, she reached for her cell phone and called Marva.

Marva answered the phone on the third ring. Before she could say anything Kat, said I’m sorry, I’m sorry, I’m sorry.

Marva said; it’s o k Hun, what’s the matter.

I can’t figure out what to do. I haven’t had to think about this for 35 years.

Think about what asked Marva, now sounding more awake.

How do I tell a man that I can see has respect for me, what I’m into that I just want to suck his cock, and watch his milk squirt out of the tip. Marva you’re the only one who has ever known the truth about me.

Remember what I said; the good lord helps those who help themselves. You’re not 20 something anymore, you’re 60 something, tell him what you want. That works for me said Marva. Let me know how it turns out. Goodnight.


Kat completed three revolutions around the subdivision Friday morning, when she stepped onto her scale after her shower; she discovered that she had lost six pounds since Monday. She was pleased, but she knew those were the easy pounds to lose, the remaining nine pounds would be much tougher to shed.


Jon Thomas speaking; Look at her Michael, she looks like Rocky Balboa running up those steps, she’s getting ready to rumble I yell in my announcer’s voice.

I can’t wait to see this said Michael.

You’re a sick puppy. You want to watch her get fucked don’t you?

I say while shaking my head at Michael.


Later in the morning she went out for an iced coffee, and ended up also having a salad for lunch. After lunch she was drawn like a moth is drawn to a flame; to a store she could see from the window of the coffee shop.

The panty boutique smelled heavenly, and the lingerie was lovely and tasteful, but also sexy. Kat bought one bra and panty set. She visualizes how the navy blue bra with lace cutouts would look covered with Roscoe’s creamy white cum.


Jon Thomas speaking; Am I the only one who loves to watch women shop for panties I ask?

Now I’m starting to like you, said Michael.


Kat wore her hair pinned up, she had on comfortable shoes, grey slacks and a button up, loose fitting white shirt when she open her front door for Roscoe. Come in, and welcome to my home said Kat as she opened her arms to give Roscoe a welcoming hug.

Dinner is simmering, it will be ready in a little while, but I hoped you would have a drink with me, even though I know we’re both health nuts, she said while smiling. She motioned for Roscoe to have a seat on the couch while she went to make the drinks, what would you like asked Kat, as she walked toward the kitchen?

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