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Introduction:

Part one of this story was based on true events. A little embellihment here and there made it a little more interesting reading. All the characters were actual and Joy’s 77 year old mother, who will be introduced in this segment, is a real person, too. Della may have a lot of years on her, but the old broad can still appreciate good sex. That’s true, too.
The Boss’ Trophy Wife part 2

This writer’s imagination has been working overtime, so now I’ll bring you a mixture of true events and fantasy.
************
About eight months after I began working for Joy, I began seeing a few signs of worry in her face. I didn’t worry too much about it when I was slamming her pussy or asshole, or getting my nuts off into her mouth. One day, after a session of hot sex in one of the motel rooms, Joy asked me if I’d just lay beside her and hold her a while.
I had no problem with curling my arms around Joy and pulling her naked body to mine. I’d done exactly the same thing so many times. I couldn’t help but think of how much she reminded me of the TV personality, Kelly Ripa. Even as old as Joy was, her legs were nicer than Kelly’s, and her tits… as small as they were, you could definitely tell she had some nice ones (except when she was lying on her back, when you could only see the fine nipples). Sometimes, Kelly’s tits appear to be completely non-existent. Joy’s hair is shorter, but about the same color… her stylist takes care of the grey.

As she slowly stroked my limp cock, I asked, “Something bothering you today, Puss?” I had tagged the nickname on her several months ago and she didn’t seem to mind it at all.

“I’ve been thinking about mother a lot, the last couple of days. She enjoyed your cock as much as I do. I wish she was still here with us, just one more time.”

***** Della, Joy’s mom, had died at the age of 78, just two weeks before. She had been a fixture at the truck plaza’s casino, and loved to flirt.

My mind drifted back to the first time she had joined one of our ‘sessions’. It was a hot summer day and Joy had already filled me in on Della’s needs. She had undergone a series of surgeries on her female organs during her forties. As a result, she had no sexual feelings inside her pussy cavity. By chance, she discovered that she could still orgasm with her asshole stuffed full of cock or a dildo.

We all met at Della’s condo, on the bank of the Mississippi, in St. Louis’s French Quarter. Mid-day found all her younger neighbors at work or running errands. Della would never even answer the front door without her make-up on. When I knocked, she opened the door wide. Her make-up made her look years younger, but it was her birthday suit that caught my eye. She was small, like Joy. Her tits hung flat against her rib cage. In fact, loose skin hung everywhere, except her ample ass.

“Come on in, Don. I know you’re probably wondering why you got involved with a crazy old woman who likes getting ass fucked.”

“Now, now… let’s don’t talk about Joy when she’s not around to defend herself.” I bent down, tweaked an old nipple, and whispered, “Even though she’s crazy, she gives the best blow job within a hundred miles in any direction. Besides, I guess she gets her love of anal from her lovely mom.” I kissed the old lady on the forehead and winked at Joy, who was standing five feet behind her with a smile on her pretty face.

“Pffft, I’m not talking about Joy and you know it. My poor old body didn’t look like this forty years ago, you should have known me then.”

“I damn sure wish I had known both of you forty years ago. So what’s on tap for today, ladies? I took a Cialis about two hours ago and I brought along my cock pump, too, just in case ol’ Fat Boy doesn’t want to cooperate.”

Joy led the way to Della’s bedroom. The custom made bed was bigger than a king-size, and had the full compliment of four poster and canopy. The handmade sheets were pink silk… yes, silk. I had never even seen a set of silk sheets, now I was going to fuck two rich women on them. I began to undress when Della took over, “I’ll do this, young man. And it’s alright for me to call you young. I was thirteen when you were born. Ohhhh, nice! I can’t wait to see what this looks like when it gets completely hard. My husband, Chuck, was a little man with a little dick,” her eyes diverted for a few seconds and she stared away, as if lost in thought. “But he could dance, Lord how he could dance. We used to ballroom dance. Bet you never thought a skinny old broad like me could dance, huh?”

“Joy told me that you used to love to dance… before you found out that your husband didn’t have the only dick in the world.”

Joy snickered. She was enjoying the exchange between her mother and I. She had caught her parents fucking another couple at a swap party when she was a teenager. From that day on, she and Della had an understanding and shared many men and boys. One night, Della encouraged Joy to straddle her own father while he was passed out, drunk.

Chuck was naked in his bed, his dick was soft when Della took it into her talented mouth. As it began to firm up, Joy took over and sucked her dad into a full blown hard-on. Della watched as Joy climbed aboard and helped her line up Chucks cock. The girl sank onto it, worked her cunt muscles for a few seconds, then started sliding up and down.

Her movements became more of a rocking motion as excitement built. With her hands on her father’s shoulders, she talked to the unconscious man as if he were listening, “Oh, yeah, daddy. Mmmm yeah, right there. God, that feels so good. Oh, yeah. If you can hear me, daddy, you can have this.. mmmm … you can have some of this… uh, uh… my pussy anytime you want. Oh shit! Whether… you want your… mmmm… little girl’s pussy or not... fuck, yeah… I’ll fuck you every time I find you’re passed out. Ohh, ohhhh, ohhhhhhhh… Goddddddd, Mama, here I cummmm, daddy! Ghnnnn, Unnnnnggh, OHHHHHHHHH!!!!!!!! SHIIIIIIITTTT!!”

Joy had told me that she didn’t know if it was because, it was her father, or she was just extra horny that night, but she nearly passed out, herself, Due to the strength of her orgasm. They were never able to coerce Sherri, her sister to participate in her family’s incest, though. Sherri was six years younger than Joy and just as hot.

When I felt my cock inside a warm, soothing, experienced mouth, I looked down at the top of Della’s head. There! In her left hand… I could barely see her dentures. However, as many times as I had sex with that old woman, I never saw her face without them in place..

The dildo Joy produced was something I’d never seen. It was a strap-on, with an extra appendage curling down and back up. Once the Velcro held it in place, the ‘curl’ was inserted inside her own ass. The seven inch fake cock was getting a coat of KY jelly when she smiled and said, “This little old lady is going to fuck your old perverted ass, Don. This thing is new and all three of us will be trying it out.”

I started to protest. Although Joy, and others, had run fingers up my ass before, nothing larger had penetrated past my sphincter. I was a pushover for her, though, and I knew protesting would be a futile effort.

Della crawled to middle of the huge bed and smiled as she said, “Put that cock in here, big boy. I need to feel it inside me.”

She relaxed her anus and accepted my entire shaft, easily. Being bent over her small body exposed my own asshole to the probing dildo. After a half dozen thrusts, it was lodged inside my bowels… there was pain, but not as much as I had expected. The contraption was built in a manner that, when Joy pulled back, the ‘curl’ sank deeper into her own guts. Each time she shoved forward into my anus, her clit was massaged by the front. The first round of orgasms came in reverse order than what I was expecting.

Joy began bucking hard, in and out of my ass… and in and out of hers. She yelled, “OH GODDAMN! THIS IS FUCKING.. OHH, OHH MY GODDDDDD, I’M GONNA…. AHHHHHHHHHHHHHH!!!!”
Just as she finished, my balls tightened and blew my load into Della, the heat of which made her have a tremendous orgasm, too. She wasn’t nearly as vocal as her daughter, but then her voice was softer, anyway.

Needless to say, there was a total collapse onto those silk sheets, with poor old Della on the bottom. All our assholes were still full, but my dick was shriveling inside of her. The dildo in Joy was still stimulating her, making her wiggle as she lay on my back.

We all had a giggle when the 77 year-old managed to breathe out a few words, “If you two horny kids will get the fuck off me, I just may live to do this again. *****

“She may have been old, skinny, and had a painted face, but I have to admit, I miss her, too.” I pulled Joy a little tighter and kissed her cheek, “She loved you more than anything, you know.”

Her hand left my dick and traveled up my chest to my chin, “There’s just so much other shit going on, Don. You know Jake’s heart is acting up again, his daughter told me the other day that she wished he’d just go ahead and die; she could use the money. Is that a sick, fucking, mind?

“Junior wants him to turn all his finance company cash over to him, and let him have complete control of six million dollars. Can you believe that idiot being in control of that much money?

“I’m trying to get him to update his will. Those two have never forgiven him for divorcing their crazy mother, but… he thinks they’ll change if he keeps dumping money on them. He knows I cheat on him, but I’ll always be there to fuck him or whatever else he wants, and he knows that. Do you think my mind is just as fucked up as his two kids’?”

“You know… I’m laying in bed with Jake’s wife. She just got through strapping some fantastic pussy on this old man. By the way, that was the only birthday present I got this year and I thank you for it.

“As far as what I think… if you gave ol’ Jake a fucking like the one I just got, he’d sign anything you hand him. I think his dumbass kids deserve to inherit something, Puss, but you need to do whatever it takes to be able to take care of yourself. I have an attorney friend who we can talk to. Just one condition, though… he’s got a dick like a donkey and if he gets it hung in you, you’ll kick my sagging ass to the curb. So please don’t give him any pussy.”

She started ‘singing’, “Oh my goodness… Don-nie’s jeal-ous, Don-nie’s jeal-ous” I pinched her nipple and she jumped out of bed, still teasing me, “I’m going to get a shower before I get back to work. Wanna wash my back… or whatever?”

Five minutes later, as I was washing her tits (giving the nipples most of the attention) Joy stopped my hands and stared at my face. I could feel her eyes examine mine, then my nose, cheeks, ears, mouth… eyes and mouth… eyes and mouth. It was the ages old signal for ‘kiss me’. My lips touched hers while she continued to stare into my eyes. My hand raised her chin and I saw a tear in her eye. Her arms went around my neck and her hand pulled the back of my head, forcing my lips back to hers.

We kissed. We had kissed many, many times but this was a toe-curling, ass-clenching, mind-boggling kiss. One like I had never experienced in my 63 years. Involuntarily, my cock rose to attention. Feeling it against her naked legs, Joy pressed her little body into mine harder. Our hands explored each other, but for some reason, it was a different feeling than before.

When our faces finally broke free, Joy spoke first, “I’ve never felt like this before. I feel so safe and so loved when I’m in your arms. I’ve told myself for ten years that I’d never fall in love with any man, again… well, that didn’t work. I love you Don, my fucking God, how I love you. I don’t have any idea what has happened to me, but I want your arms around me until the day I die.”

Her right leg lifted to my waist and curled around my back. I pressed her sweet ass against the wall of the shower and entered her love tunnel. As the spray ran down our sides, we made love. Yes, it was love, not just awesome, kinky, or dirty sex. My cock slid in and out slowly, hesitating slightly each time I bottomed out. Our lips, tongues and hands explored each others’ neck, ears, foreheads, shoulders.

Joy’s first orgasm hit her hard. She grasped my arms and hummed quietly. Then, gasping, her eyes rolled back and she moaned, “Ohhh, God, I love you, I love you, I love you.”

I kept expecting her to get louder, maybe even scream, but it never came. Our kisses resumed. My dick felt like it was the largest it had ever been. As my own body started to send signals to my testicles, Joy came again. This time she was a little more vocal and dropped her hands to my waist, tugging me in as deep as my cock could reach. “Ahhhhh… yesssss, right there darling… that’s right, right there. Oh, oh, oh, oh.. mmmm, GOD, YES, FUUUUCK MEEEEEEEEE, BABYYYYY!!

My balls were actually in pain as they sent blast after blast of steaming cum into my lover. Even after they were empty, the spasms continued, aching to fill her more.

We slid to the floor and sat under that shower until it began running out of hot water. I increased the flow, long enough for us to get our cum, and pussy juice cleaned up, then we dried and went back to the bed. Two hours later, we awoke in each others’ arms.

We had some serious decisions to make………..

Please bear with me, I'll be very busy for the next few weeks but Part 3 is in the works...
Thanks,
Don'sdick
5 comments

Anonymous readerReport

2014-04-01 14:07:55
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2014-03-22 17:32:02
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2014-01-17 05:16:09
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2013-10-26 11:29:34
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anonymous readerReport

2013-05-08 01:17:57
Ooh! Almost. So close. One or two paragraphs more and I'd have made a mess all over myself. Next one maybe?

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