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I would recommend reading part one of Tony’s World before starting this. While it’s not essential, it will give you the backstory of our hero Tony and his newfound love life.
Enjoy
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It’s funny how life can throw something at you when you least expect it. Look at me for example. Getting shitfaced as often as possible was a genuine life goal. Worming my way into some college girls panties the odd time being the icing on the cake. Fitting those two tasks in around a pretty sweet summer job in an up market golf resort had been my biggest challenge.
Well that certainly changed three weeks ago when I somehow managed to get involved with my childhood crush, Cindy Smith, who happens to be my Mom’s friend. And just to make matters even worse, she’s also my best friend Brian’s Mom. Yeah I know, I’m probably playing with fire. But so would you if you saw her. She’s sex on fucking legs.
I never really had a thing for milfs before, but at 51, Cindy is by far the oldest woman I’ve ever been with. I had no idea what to expect when we first hooked up, but I can say with all honestly, she’s out of this world in the sack. I’m only 21, so it’s a bit crazy that she’s 30 years older than me! She doesn’t look it, not even close. But if I’m honest, her age is a big part of the attraction. That, and the fact I used to jerk off looking at her on TV when I got home from school, back when she worked as a news anchor on the local TV channel. Don’t get me wrong, she’s not a big celebrity or anything, but she definitely has the looks for TV.
My three week affair with a married woman isn’t the full story here. What started off as a bored housewife looking for a good seeing to, her first in years probably, quickly turned into something very different.
You see, it turns out Cindy and her husband Paul are into some kinky shit. A new revelation apparently. He’s been screwing around with some younger woman he works with, and Cindy knew about it. So their marriage was on the ropes long before I entered the equation. Anyway, long story short, he gets off on looking at his wife get fucked by yours truly. So basically our deal is I call round to hers, do whatever nasty things I want with her, all the while he’s lurking in the shadows doing who the fuck knows what.
I generally don’t hang around for long after I dump my load in or on Cindy, leaving them to get on with whatever floats their boat. I’m not going to lie, it’s a nice little arrangement. I mean, what 21 year old wouldn’t jump at the chance to nail the town’s super milf, even if her baldy fuck husband is lingering around like a bad smell. He keeps his distance, mostly, while I ram his wife, but I’ve seen him on her in a flash before I even leave the room, head buried in between her legs. Sucking my freshly deposited load straight out of her battered snatch being his latest preference last night.
I have just two rules that Cindy agreed to early on in this thing. She has to be fresh for me, if you know what I mean, and he has to keep out of my way. I stay the night with Cindy sometimes. Paul gets the hint and fucks off to the spare room those nights, the loser. I never liked him, ever since we were kids, he has always been a prize winning prick. He definitely doesn’t like me either, which means less than nothing to me. I imagine it kills him having an obsession like this, which makes it even sweeter having his wife’s pussy on tap knowing he can do zilch about it.
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You’re looking delicious today, texts Cindy.
I’m at work in the golf club restaurant by the way, I spotted Cindy come in a few minutes ago, with three friends. Her sister Molly, who is also a hot, slightly younger piece of ass. Another friend Pippa, a 40 year old who makes me hard every time I see her, she’s the picture of perfection. And also my Mom. Which makes this a little awkward. She hasn’t a clue about what Cindy and I get up to. Nobody does.
I don’t think you should be texting me while you’re sitting beside my Mom. What if she sees, I reply, when I go into the kitchen so none of our guests or club members see me texting.
Oh, don’t be so uptight. I’m allowed text my stud if I want to, especially after what I let you do to me last night. I can barely walk straight today after that fat cock of yours, she writes back.
I think it’s for the best if I just ignore her.
My phone vibrates again a few minutes later. I’m just after taking an order from a table of old guys, but I risk checking my phone as I walk back to the kitchen.
You’re ears must be burning, she says, rather cryptically.
Why? I ask, glancing over to her table. She’s looking sexy as hell by the way, and I can’t help but gawk at her perfect tits spilling out of her low cut top. Bayan Escort How that woman is 51 is hard to believe. Her skin is flawless. OK, pull yourself together Tony.
You’re the hot topic of conversation with the ladies today, is all.
What do you mean? I type back quickly. I’m back in the safety of the kitchen now by the way. What the fuck is going on at that table.
Well, we can’t help but admire what a handsome young man you are, to put it mildly, she says.
Yeah right. Hardly, I write. I know those mature ladies can get pretty raunchy, especially after a few glasses of wine. But I seriously doubt they would talk about me like that in front of Mom.
Oh dear, you have a lot of learn about us ladies, very little is off limits when we get together……and when wine is involved! Cindy texts.
I stick my phone back in my pocket and try to forget about what she just said. I’m definitely going to avoid their table, it’s too mortifying. Cindy must decide to give me a break and she lays off the texts while they’re eating their meal.
Then almost an hour later, my phone vibrates again.
I want you tonight. Paul is away until Saturday so it will be just the two of us. Would you like that? she texts. I look over at their table and I see they’re getting ready to leave.
I catch Pippa’s eye, and I immediately feel myself harden. What I wouldn’t do to get her on her back. I’m a little surprised. She rarely even looks in my direction. I give her a little smile.
She doesn’t smile back. She just stares through me for a few seconds, then turns away with a look of disgust on her face. I feel stupid for trying to flirt with her. She’s hot, but she definitely knows it. Whatever, she might be fucking full of herself, but she still has to go home to her limp dick pensioner husband, the gold digger. She’s probably miserable.
I’ll be there. You won’t be able to walk at all tomorrow when I’m finished with you, for real, I text back, letting my frustration and embarrassment at what just happened with Pippa color my response. Childish, I know.
Cindy laps this up of course, the slut.
I hope you’re not all talk. You better back that up, she replies.
You’ll see, I text, and immediately put my phone away.
I look over at the group as they stand up, and I see Mom walking towards me.
“You’re very unfriendly, you didn’t even come over to say hello,” she says as she approaches, but she leans in for a hug anyway despite her admonishment.
I look over Mom’s shoulder as we hug and I see Cindy stand up. She’s wearing a blue sleeveless top with a plunging neckline, and a pair of really short denim cut-offs that are literally painted on. I have an overwhelming urge to slap her sexy ass hard. She catches my eye and gives me a smile and a little wink. Looking at her immediately causes my cock to stir, as I know I will be taking that walking fantasy to bed in a matter of hours.
Pretty much every man in the room turns to look at Cindy. Some of them who are with their wives manage to do it discreetly, but the groups of men don’t need to worry about shit like that so they openly crane their necks to stare. She is probably used to it as she doesn’t even seem to notice, well she pretends not to anyway.
Mom releases me from her hug, and I realize I have a semi in my pants. Shit, I hope she didn’t feel it and get the wrong idea. I have a pretty big cock, so even a semi can be quite obvious. Mom is a very good looking woman but I try not to let my hormones get the better of me where’s she’s concerned, so I force myself to never look at her in that way. I’ll leave that to my friends. They’ve all been obsessed with her since we were kids. Brian in particular.
“Will you be home for dinner tonight?” she asks. She doesn’t seem to have noticed my situation.
“No Mom, I’ve plans after work,” I say, my mind flashing forward to my evening ahead.
“You have a lot of “plans after work” recently I notice,” she says, and does the air quotes thing with her fingers. “Have you a secret girlfriend you’re not telling me about?”
“No Mom, it’s nothing like that,” I say. “Did you have a nice lunch?” I ask then, trying to change the subject.
“Hmmm,” says Mom, and she give me a suspicious look. But she drops it. “Lunch was lovely, as usual. Those ladies are such good fun. They talked a lot about what a fine young man you’ve grown into,” she says. Maybe Cindy exaggerated in her texts.
“Sure, whatever Mom,” I say dismissively.
“No it’s true dear. You need to learn to take a compliment. I won’t embarrass you with the more colorful language the others used, but they’re intentions are good,” Mom says.
“Even Pippa,” I say, immediately regretting not stopping myself.
“Oh, do you have a little crush on Pip? She is a beautiful young woman I suppose,” Mom says, a little smile showing on her face. “She didn’t say much, just agreed with Cindy and Molly. She’s Escort quiet, but she’s such a nice person. Those other two don’t hold back though, they’re two wild women especially when they get their hands on wine.”
“She’s 40 Mom, hardly a young woman,” I say, unintentionally sounding a little bitter. I just get the impression Pippa looks down her nose at me.
“When you’re pushing 50 like me, you would give anything to be 40 again. In Pippa’s case, she doesn’t even look 30. I don’t know how she does it,” she says.
“That’s the benefits of never doing a days work Mom,” I say.
“Now now Tony, we don’t judge. Pippa seems very happy with Leonard. Love knows no age,” Mom says.
“Sure, she married him for love. He just happens to be a multi-millionaire. How old is he anyway? He has be in his eighties?” I say.
“He’s 82, but he’s a lovely man,” says Mom.
“Whatever,” I say, and smile at Mom. “I better get back to work.”
“OK dear, don’t stay out too late tonight,” she says as she walks away towards the other three who are waiting for her by the door.
Cindy gives me a little smile and a wave, while her sister Molly stares at my crotch, and I notice she subtly licks her lips. Pippa is staring at her phone looking bored.
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Cindy opens the front door before I even press the bell. She’s beaming, her smile at seeing me showing off her perfectly white teeth. I notice she’s wearing the same clothes as when she was in the restaurant earlier today.
I step into her home and she kisses me as she reaches for the door to close it behind me. Kissing Cindy never gets old. It’s a such a surreal experience kissing the woman who was my go to jerk off material since I first began to notice women.
“I’ve been looking forward to that all day,” she says, when she removes her tongue from my mouth.
She turns and starts walking towards her sitting room, and that’s when I give her perfect round denim covered ass a really hard slap. The sound is louder than I expected as it echos in her huge entrance hallway. Cindy yelps loudly and bounces on her feet as she comes to a standstill.
“That’s what I’ve been looking forward to all day,” I say, then I give her another spank, this one even harder. She grunts this time. “This fucking ass is just begging to be spanked,” I say as I slap it again, more softly this time and I hold on to a cheek to give it a good grope. “You know you had every man in the restaurant staring at it? You must have caused twenty-five or thirty erections there today wearing something like this.”
She doesn’t say anything, but I know she loves hearing shit like this. She wouldn’t wear these shorts unless she wanted to tent some pants.
I’m fully hard at this stage, so I move in close behind her and reach around to open her shorts, first the top button and then I pull down the zipper. I yank the short shorts and panties down to just above her knees, then I fish my cock out of my pants and enter her in one deep shove. I give it to her hard as we stand in her hallway, then I unload deep in her cunt less than two minutes later. A nice quick welcome fuck.
“I’m obsessed with that cock of yours Tony,” Cindy says as I slowly withdraw it from her pussy. I do have a nice big cock, I must admit. It’s maybe a little over 7 inches, but it’s a thick fucker. A real pussy stretcher.
I’ve learned a lot about Cindy over the past three weeks. She likes when I take control, like just now. She gets off when I take what I want. And she loves a good spanking, it definitely gets her pussy juices flowing.
We both pull up our pants, but Cindy’s is in a considerably damper state than mine as she leaks my big load into them. When we eventually make our way into her sitting room. I flick on the TV and make myself at home.
“Would you like something to eat honey?” she asks. “I made dinner for both of us when I knew you would be coming over.”
“Sounds good,” I say. I’m starving, I haven’t eaten in hours.
“Wonderful, I’ll just go and check on it.”
Cindy likes looking after me like this I’ve noticed. Maybe it’s her motherly instincts. I’m getting as much incredible sex as I want, and fed delicious food, so what more could I ask for. I kick off my shoes and lay down on the sofa as I channel surf. I always loved hanging around Cindy’s house when I was a kid, even before I started having the hots for her. I would call over to play video games with Brian for hours.
“Dinner is ready baby,” Cindy says when she sticks her head into the room a few minutes later. “I’m just going upstairs to get changed. You made a bit of a mess in my shorts. Go ahead and start without me.”
I just chuckle to myself when she says that, happy with my work, and I make my way down to the dining room.
Cindy comes down a few minutes later wearing a short black Ankara Eskort silk robe that just covers her ass.
“How am I supposed to concentrate on my food with you wearing that?” I say. “You’re so fucking hot Cindy, it’s not even funny.”
“Well I’m glad you think so. Now eat, we have lots of time for all that when you’re full. You need to eat to keep your strength up,” she says with a cheeky smile, then she grabs a plate of food for herself.
After dinner we move into the sitting room and just sit and chat for the next hour or more. It’s nice getting to know each other properly, without her husband around.
“I think we should do this more often. Just the two of us,” I say.
“Me too Tony, I really like spending time with you. I shouldn’t say this, but I’m starting to feel really close to you,” she says honestly.
“I don’t think your husband would be very happy about that,” I say then, looking for a reaction.
“That’s an added bonus. Fuck him, he’s lucky I haven’t kicked his ass out of the house. But knowing him, this would probably only make him even hornier for me. He gets off on being totally humiliated. So that’s why I’m not going to tell him about seeing you tonight. I want to keep it behind his back. Give him some of his own medicine,” she says with a bitter smile.
“Oh you’re a bad girl,” I say. “But I like it. Sneaking around behind your husband’s back, even though he wants you to cheat on him, I don’t think there is even a word for that,” I say, and we both laugh.
“Yeah, it’s kinda stupid, but a girl’s gotta have her secrets. Tony, you should stay over tonight?” Cindy blurts out then, sounding a little fragile.
“I was planning to,” I say, and I place my hand on her bare knee as she sits beside me on the sofa, with one foot tucked under her ass.
We spend the next few minutes kissing softly, and then progressing to a passionate make out session on her sofa, and that of course leads to the inevitable boner, which is predictably followed by a toe curling blowjob.
Her robe doesn’t fully cover her ass as she lays down flat on her belly on the sofa with her head in my lap. Cindy gives great head, and the view I have of her blonde hair held back with a hairband, down to her half exposed panty covered ass and perfect legs is a truly amazing sight.
I slip my hand down into her see-through black panties and grope her ass, sliding my finger across her little tight puckered hole on my way in between her legs to her dripping slit. She keeps her pussy hairless, which really suits her. I push as much of my middle finger into her as I can, and then I just lean my head back on the plush cushions, basking in the heavenly position I find myself in.
“Tell me before you come,” she says quickly when she lifts her mouth off my pole for a second, before engulfing my entire length down her throat again. She seems to have zero gag reflex.
I notice she quickens her pace a little, her head now bobbing up and down more frequently. It does the trick, and I give her head a little tap so she knows what’s about to happen.
Quick as a flash, she jumps up, pulls her panties to the side as she climbs up on top of me. She reaches down between us and positions my iron hard cock between her pussy folds. Then when she’s happy everything is lined up, she wraps her arms around my neck and pulls me in for a deep sloppy kiss. Just as her tongue finds mine, she drops her pussy down hard, and grinds herself on my pubic bone.
I barely managed to hold off long enough, and as soon as she bottoms out I unload into her for the second time today. But this ejaculation is much larger than the previous one. Probably due to how long she had been edging me with her slow sucking.
“That’s it baby, come inside Mommy,” Cindy whispers when she breaks our kiss as she feels my third or fourth rope of cum hit her cervix.
What the hell! She’s never said anything like that before.
“Hmmm, give Mommy all your messy sperm, that’s a good boy,” she continues on whispering, and then she licks my ear, which feels very nice.
When she says this, I harden even more and an extra squirt or two of cum shoots out, completely emptying my balls.
“I see someone knows how to please his Mommy,” she says smiling, clearly delighted with herself after getting a reaction from me.
We stay in this position for another few minutes, my cock still buried inside her, as we kiss each other tenderly. Finally, she lifts herself off and a huge load of my cum falls out of her onto the wooden floor. She doesn’t bother cleaning it up, but just curls up beside me on the sofa instead.
“You liked it when I said Mommy, didn’t you?” she says after a while. Her head now is resting on my chest and she’s idly fondling my soft, fully spent cock.
“I don’t know what you’re talking about,” I say, but my cock lets me down as it begins to stiffen in her hand.
“Yeah right. It’s OK Tony, a little role play is fun,” says Cindy. “Remember, nothing is off limits between you and me. Even stuff like that.”
I’m not sure how to respond.
“Maybe,” I say eventually.
“Come on mister, we’re going to bed,” and with that she stands up and leads me by the hand up the stairs.
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