Double Booked & Double Parked Ch. 02: Double Stuffed

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Two men give a lonely MILF an amazing threesome.
7.6k words
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Part 2 of the 2 part series

Updated 01/02/2024
Created 11/28/2023
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DOUBLE BOOKED Ch 02: DOUBLE STUFFED

Summary: Two men give a lonely MILF an amazing threesome.

Note 1: Thanks to Breezy for this twisted idea.

Note 2: Thanks to Sams Island for editing.

DOUBLE BOOKED Ch 02: DOUBLE STUFFED

After taking Alex's anal cherry, Carl stayed with his man-of-the-house role and went off to take a nap. Joy, meanwhile, had a lot to do to pull off the Thanksgiving dinner she'd promised her surprise housemates, and was happy when Alex volunteered to help.

About an hour later, Joy was in the middle of making the dressing, fantasizing about ways to incorporate Alex's delicious semen, which she could still taste on her tongue, when her phone rang. "It's my daughter," she said.

"Tell her I say hi," Alex smiled.

When Joy's eyes went wide, Alex chuckled and added, "Just kidding. I won't say anything."

"Thank you," she said, glad it wasn't a video call since she was still only in her garter and stockings, although she had put an apron on top. She pressed Answer. "Hi, honey, how's London?"

"Raining," Lori answered, looking out of her hotel window as it poured.

"That's London for you," Joy said.

"Yeah, it hasn't really stopped since we got here," Lori groused.

"Well, don't let that stop you from exploring the city," Joy said, as Carl walked into the kitchen.

Alex went over to him and whispered, "It's her daughter, so please keep it quiet."

"All right," Carl nodded. Then he pointed to his dick.

Alex dropped to his knees and stuffed his friend's flaccid cock in his mouth. This time the load would be his.

Distracted by seeing Alex again take the big cock in his mouth, Joy almost missed her daughter's next words, but they seemed to be just more bitching about the weather. She responded with, "I'm just saying, accept that you're in England and don't let the rain ruin your holiday."

Carl waved Joy over.

Joy shook her head no.

Carl mouthed, "Now."

Joy, led by her submissive side as well as her burning pussy, walked over to the sex act as she listened to her daughter still complaining. As she reached Carl, she said, "Well, what are your plans for Thanksgiving?"

Carl moved his hand to her pussy and began rubbing it slowly.

Joy bit her lip as she tried to listen to Lori. When her daughter asked what she was doing, she replied, "Oh, just prepping the meal." She bit her lip even harder when she realized what she'd just said. How was she going to explain why she was prepping a Thanksgiving meal when she was all on her own as far as Lori knew. Fortunately, her daughter didn't ask.

Joy watched Alex suck cock; she felt Carl's hand teasing her pussy; God, she was on fire. "Just put your rain jacket on and explore the city," Joy said to her harping daughter, trying hard not to moan. These were the first male fingers to touch her in years.

Alex was really getting into sucking Carl, but still noticed Joy's shift in tone and became curious about what was happening between his business partner and the lonely MILF they'd stumbled across in this double-booked Airbnb.

"Anyway, I got to go," Joy said. "Thanks for calling and I will make you and Barry a Thanksgiving meal when you get back."

Carl pinched her clit ever so slightly between his fingers, making Joy's voice breathy as she quickly said, "Okay, bye, love you too." Once she hung up, she said, "You asshole."

"What?" protested Carl. "You've been prepping everything for our Thanksgiving meal, I'm just prepping you for your Thanksgiving fuck."

"Oooooh," she moaned, as he rubbed her clit. "I know what I'll be giving thanks for."

"But our meal comes first, so I'll let the kitchen staff get back to it." Carl gave her clit a slap, pulled his dick out of Alex's mouth, and moved away.

"You bastard," Joy said.

"He does love to tease," Alex said, his face now just inches away from Joy's wet pussy.

"Jesus," said Joy, almost prayerfully... as if that would stop the burning going through her body.

Alex resisted the temptation to dive in and lick her inviting pussy, and instead stood up, his rock-hard dick jutting out. "What can I help you with?" he asked.

"Oh, I think you know exactly what you can help me with," she smiled, squeezing his cock before sauntering away... she too could tease.

Now it was Alex's turn to mutter, "Jesus." But even as he shook his head in frustration, he was happy to know that despite having given his ass to a man, a woman could still turn his cock to iron.

"Stop checking out my ass," Joy playfully teased, looking back with a smile.

"Oh, we'll be doing more than checking it out later," Carl chipped in like he always did.

"Don't make promises you don't intend to keep," Joy said, going to peel potatoes.

"Oh, I don't," Carl said, definitely looking forward to tag-teaming this spirited MILF. While he and Alex had done threesomes with other women, and even men, they had yet to double penetrate someone, since he didn't count spit-roasts as DP... and Joy's body was just made for simultaneous front- and back-end pounding.

"I'll be holding you to that," Joy said, as Carl came up behind her and slid his dick between her parted legs, as he cupped her big tits.

"Do you want to get fucked tonight?" Carl asked, his cock nestled lengthwise between her wet pussy lips.

"Yes," she moaned, as she felt his dick twitch between her swelling labia.

"I mean seriously fucked," he whispered, pinching her nipples.

"Oh fuck," Joy moaned, thinking he was going to slide his dick into her right now... while she was holding a knife in one hand.

"Is that a yes?" Carl said, twitching his cock on purpose.

"Yes, I want you to fuck my pussy hard." Then Joy turned her gaze onto Alex. "And my asshole too, like you did to your butt boy."

Alex could feel his cheeks going red at the reference to him even though he should be used to it now.

"Well, while you both have tempting bottom ends," Carl said, as he slowly dry humped the older woman... although dry had nothing to do with what he was feeling up against his throbbing cock... "he is not also blessed with the hot swamp I feel between your legs." It was a swamp he wanted to plunge into right now, but somehow, he managed to hold back.

"Well, fancy that," Joy moaned as she rocked her pelvis to rub her puss on his cock. "I have two holes and you both have a dick."

"We are going to fuck you so good," Carl said, slapping her ass and moving away yet again.

"Jesus," she whined, "you can't do that to a woman my age."

Carl didn't respond, but Alex said, "You do look incredibly sexy when you're kept on the edge."

"You too with the teasing?" she said, feeling flustered and hot... menopause mixed with horniness made the room feel like a sauna. Then she remembered that her being there with the boys was only an accident of double booking. "Hey, you know, I really appreciate all the attention and I sure as fuck won't say no, but are you sure I'm not intruding on your man's weekend?"

Alex laughed, "Well, I may have thought that before you watched and encouraged me as I gave up my anal cherry, but I'm more than willing to give as much as I receive."

"I did get a little nasty," Joy said. "Sorry, it was just such a turn on."

"Really?" Alex asked.

"Yeah, I can't explain it," she said. "I never would have thought that would turn me on at all, but it sure did."

"Tell me about it," Alex chuckled awkwardly. "Six months ago, I hadn't even once considered sucking a dick, never mind taking it in the ass."

"And now?" Joy asked, noticing Carl was no longer in the kitchen.

"Now I can't get enough of his cock in my mouth, and I fear the same feelings will be true about getting fucked," Alex admitted, already looking forward to Carl's dick back in his ass. "By the way, your nasty words of encouragement actually made it better."

"It did?" she asked, as she peeled the potatoes, old school with a knife and not some peeler.

"Yeah, I know, weird," Alex said, trying to process it all.

"It's not weird," she said, thinking about her own sexuality. "For example, I'm a serious businesswoman and a fighter for female equality, in fact I have a fundraiser for Governor Daphne Greene in December. But when I'm in the bedroom I want to be fucked, dominated, called names... just used and pounded."

"Shit, me too," he said. "Although not only in the bedroom, LOL."

Trying to balance this incredible conversation with their meal plan, Joy asked, "Can you cut the potatoes into cubes for me?" She then went to the fridge to grab carrots. Thankfully, even though she was originally planning to cook for two, she'd brought enough supplies for four.

"Sure," he said, walking around the counter and grabbing the knife. "And you know," he said, wanting to make it crystal clear, "We are not gay. Bi, sure, but not gay."

With his ever-impeccable timing, Carl walked in just then, grabbed one of the fresh potato cubes, and said, "He may be a cock sucking bottom bitch, but he can still fuck a sexy babe."

"You have such a way with words," Joy smirked, as she went to work on the carrots with another knife.

"Don't I?" Carl said, catching the sarcasm, but choosing to ignore it, as he reached for the carrot she'd just peeled.

"Yeah, Carl, really knows how to sweet talk the ladies," Alex joked.

"And the cock suckers," Carl said, as he moved the carrot to Joy's pussy.

Damn, thought Alex, Carl always managed to get in the last word.

"Oooooh," Joy moaned, as the carrot slid inside her pussy.

Carl pumped the natural orange dildo in and out of Joy's pussy for a few strokes before he pulled it out and laid it on the cutting board. "Next," he said.

"W-what?" Joy stammered, as she tried to process having just been fucked by a long thin carrot.

"Give me the next carrot," he said, "let's marinate each of them."

"I have to peel it first," she said, having stopped while suddenly being fucked by one.

"Okay," Carl said. "I'll wait."

Joy quickly got to peeling the last five carrots with the surreal certainty that she was doing it to have them shoved in her soaking wet pussy. She took extra care to round off the ends.

"Carl, seriously?" Alex asked.

"What?" Carl asked. "You don't want me to marinate them in your ass, do you?"

"Jesus," Alex shook his head. "Sometimes you say some stupid shit."

"Here," Joy said meekly, handing him all five peeled carrots.

"You okay with my marination technique, Joy?" Carl asked, not waiting for an answer as he slid the second carrot in her pussy.

"It's certainly an unorthodox method," Joy moaned, although right now she was willing to do anything this man said that would get her pussy fucked.

Alex just watched, the perverse act kind of turning him on... although he sure as fuck didn't want a carrot up his ass.

Carl pulled the second carrot out and handed it to Alex, "Taste it."

Seeing the shine on the orange carrot, Alex didn't hesitate. He sucked the pussy juice off the vegetable that would soon be part of a very non-traditional Thanksgiving feast... a unique taste, but the flavors worked together.

Now, Carl took two carrots and slid them together in Joy's pussy. She moaned, "Yes, fuck me with our food."

"You like that, eh? God, I can only imagine what goes on in the kitchen of your restaurant," Carl laughed as he pumped the two carrots in her vag.

"You should see me when we have kielbasa on the menu," Joy moaned, as the makeshift dicks began to actually stimulate her.

"Well, if you do a good job with your vegetables today, young lady, we'll let you stuff yourself with organic sausage." After giving them a final twist, Carl pulled the two carrots out of the marinade and placed them with the first. Joy immediately handed him the last two roots.

"Alex," the alpha-male said to his best friend and cock sleeve, "give me the one you sucked off. It needs to be marinated again."

Alex handed him the carrot and watched in awe as Carl bundled it with the remaining two and slid all three of them together inside the wet pussy.

"Oh fuck," Joy moaned, the three carrots now thick enough to feel like a real-sized cock.

"Shit," Alex breathed.

"Yeah, you're going to be a real good slut for us today, aren't you?" Carl purred like a tomcat.

"Yes," Joy moaned.

"Yes, what?" Carl demanded.

"Yes, I'll be a real good three-hole slut for your two big sausagaes," Joy moaned, as he fucked her fast and her orgasm rose.

"Oh yeah, take your veggies," Carl growled.

"Yes, take it," Alex added, watching both the cunt-fucking carrots and Joy's sexy, vulnerable, facial expressions. Women never looked sexier in his mind than when they were getting fucked and were beyond caring about their appearances.

"Oh fuck, don't stop," Joy moaned.

Carl, being the cruel deviant he was, pumped for just a few more seconds before he pulled them out and tossed them on the cutting board.

"Bastard," Joy whimpered, her orgasm so close.

"All good comes for those who wait," Carl said, popping another potato cube into his mouth and walking away.

"Sweet baby Jesus," Joy breathed out, bent over and trembling.

"That was just mean," said Alex as he stepped closer to offer comfort.

"Yes, it was," Joy said.

"Don't worry," Carl said, still in ear shot, "we are going to fuck your brains out later."

"You fucking better," Joy said, more than a little annoyed and completely flustered.

"You sure about this?" Alex asked.

Joy sighed, then nodded her head and said, "Yeah, there's no point denying it, I like being treated like a slut. Just like you."

Alex found it odd to be called a slut. "I've never thought of myself that way before," he said.

Joy straightened up and smiled at him. "Is fuck toy or cum bucket better?" she asked. Then she reached for his cock, which was still mostly hard from watching Carl abuse her.

"No, I don't suppose so," he said.

"Well, I am all three of those things today," the naked MILF said. Then she gave his cock a firm squeeze before releasing it so she could cut up the carrots with their special Joy Juice marinade. "Slut, fuck toy and cum bucket."

Over the next hour, Carl walked in a few times to tease his two fuck holes while they continued working on dinner and encouraging each other's sluttiness. Once, the alpha moved in behind the head chef as she was making a green bean casserole and whispered, "I'm going to fuck every one of your holes with this," before finally slipping his massive dick into her at long last. But the teasing bastard did it just once before pulling back out.

"Oh, fuck!" she gasped when he walked away, leaving her so terribly empty. When he stopped at the fridge to get a beer, she nearly begged, "Can't you come back and do it some more?"

Carl just smirked as he twisted the cap off the bottle, then took a long swig as he headed back to the living room. As she stared longingly at his broad, naked back, Joy heard a football game on the TV. She mentally sighed. Even when they sucked dick and fucked men as well as women, guys were still guys.

Then Joy was gasping again as her lonely pussy was suddenly filled. Alex had glided quietly up behind her and thrust two fingers into her wet gash. "We are going to tag team the fuck out of you," he growled into her ear, while he massaged the insides of her vagina.

Joy felt his hard rod poking against her ass cheek. "I can't wait to feel that fat cock in my asshole stretching me wide," she said.

Alex pulled his fingers out of her front box and used her cunt juice as lubricant as he massaged her sphincter. "But you will wait," he said, picking up his role in Carl's teasing game. Without another word, he pulled fingers and cock away from the horny widow and moved around the kitchen island so she couldn't get to him.

At first her eyes were wide with desperation, then she burst out laughing. "You mother fucker! Both of you."

"Mother fuckers? Well, not yet, but we will be before the night is over," he grinned back at her.

Later as she was putting the turkey breast in the oven, Carl returned, and once she closed the door, he slid back inside her and declared, "You are going to be our free-use fuck slut all weekend."

Joy hadn't heard the term free-use before, but it sure sounded promising. She started to purr as it seemed Carl would be fucking her longer this time. Unfortunately, longer only meant fifteen seconds and he still didn't put in more than the first few inches.

"We are going to fuck you all day and night all over the house," he promised, before he pulled out, walked over to Alex and pointed to the floor.

Alex didn't hesitate as he dropped to his knees and sucked Joy's pussy juice off his friend's dick.

After about thirty seconds, Carl pulled out of Alex's mouth, leaving the new cock lover feeling as empty as Joy. Their tormentor turned his well-muscled frame to the woman and asked, "How long does it need to cook?"

"Um, about an hour and three-quarters," she replied, thrown by such a routine question.

"Okay, I'm going to take a nap."

"Another one?" 'Hell, if they had almost two hours to kill, why not do it fucking rather than sleeping?' she thought.

"I didn't actually get much sleep the first time," he shrugged, before walking out of the kitchen.

Joy turned her pleasingly plump body to Alex. "Why does he keep teasing us like this?"

"Don't forget," the newly branded bottom said as he got up off his knees, "he's teasing himself as well. Didn't you see his cock quivering like a divining rod?"

She stepped up to him and put a palm on his strong, young chest. "I only saw you quivering when he shoved that hog down your throat with my pussy slime all over it."

He moved his hand to her crotch and slid a finger through her slippery folds. "By the way, you taste delicious."

"Wait until you get it directly from the source," she smiled. When the smile suddenly turned into a yawn, she said, "You know, I think I'll take a nap too." She kissed Alex on the cheek, set the oven timer for an hour and a half, and walked off.

Alex, suddenly alone, shrugged, and went to the couch and took a nap too.

...

When the chiming of the countdown timer roused the ex-anal virgin, Alex sat up on the couch, half-surprised he'd actually fallen asleep. But it had turned out to be a surprisingly comfortable sofa. He went into the kitchen, only to find Joy already there.

"Didn't you nap?" he asked.

She kissed him on the cheek and said, "Yes. I've only been out here five minutes or so."

He noticed that she had her apron on again but had shed the garter and black nylons she'd been wearing earlier. Carl walked in just then, and Alex saw he was also naked, but that his hair was damp; he'd obviously just showered. The curly nest around his magnificent prick was also damp, and Alex felt an even stronger urge than usual to drop to his knees and worship his phallic deity.

Carl immediately noticed his friend's rapt attention on his heavy, dangling sausage and gave his hips a little thrust to make it bounce. "While I would love to put this in your mouth again right away," he smirked, "I found myself smelling a little ripe when I woke up. You should probably go hit the shower too before we sit down for Mistress Joy's feast. It is Thanksgiving after all, and manners count."

As Alex made his way to the bathroom, he wondered about the manners of a man who made his supposed best friend suck him dry in front of a complete stranger, a lonely widow at that, and then turned around and shot a load down the widow's throat. But then again, he realized, those were things he and Joy would both likely list among the blessings they were thankful for this year.

"It all smells delicious," Carl said when he and Joy were alone. Then he stepped up to the middle-aged beauty and grabbed her big tits just shy of painfully. "We are absolutely going to fuck you like a cheap whore," he growled. "But we do appreciate the hell out of all the effort you're putting in to take care of us." He bent and kissed her long and lovingly.