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Hey! It's been a while! I took a break for a week to deal with some art block issues. I'm still recovering for now, but I'm able to come back to y'all with some more content.

Before the art starts rolling out, we've got a group of stories for you today, starting with the second winners of the MILF May poll - Charity & Sue!

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Charity lived comfortably in the upper parts of Queen’s Beach. Her family came from old money, so with some responsible investments she was able to live off of that and leave plenty of free time to herself. That allowed the wealthy socialite to mingle with friends and entertain guests as a favorite pastime of hers. While she was known to hold some of the most enjoyed parties in the uptown area, today she was playing hostess to one old friend.

Charity and Sue were in the wealthy woman’s house, sitting together at a small and comfy table in similarly luxurious chairs. Wine, tea and snacks were set between them as Charity took a drink of her cup.

“So are the kids still on leave from their pizza place?” Charity asked. 

She was a slender woman on the taller side of things, but she was always dressed to impress in her fine white dress. As rebellious and lazy as Cash was, it was clearly some part of a backlash against her classy mother. Her blonde hair was brushed to one side while the other half was tied back behind her head in a bun stylized to resemble a flower. She had some light lipstick as well as earrings, two bracelets, a belt around her white dress, and a necklace, all of which sported some amount of gold. Broad, orange-tinted glasses added one final touch to emphasize her style and wealth. At this point she wasn’t even consciously trying to impress anyone. She did it as a reflex, since she knew that Sue was a close friend from back in her school days.

Sue just nodded tamely.

“Yes. They’re supposedly finishing up construction near the end of the month. I’m starting to wonder if my boy would go stir-crazy if his girlfriend wasn’t around for him to cook for.”

Sue was a small Asian woman, much more simply dressed than Charity. She had long, dark hair that framed her small and mousey face with a few worry lines around her eyes and nose. She always had a controlled politeness about her, something that Charity had simplified as her being shy.  She dressed far more modestly in a blouse under a long sleeve pullover and long skirt, leaving her with little actual skin exposed.

“Speaking of!” Charity asked, snatching up the topic like a hawk. “One single mom to another: how’s the dating game been treating you?”

Sue raised her eyebrows as she took another drink of her wine.

“Well I’ve been busy lately. There’s work, of course, and I’ve been looking at a new place to move into, so… it hasn’t been treating me. At all. I just don’t have the time.”

Charity pursed her lips, immediately suspicious of how much of that was true. She’d always had to twist the quieter woman’s arm to get her to go to parties or talk to people, even when Sue genuinely wanted to.

“So what do you do when those urges come along?”

“Urges?” 

“You know what I mean, Susie. With no man around, how do you take care of yourself when you get those raunchy thoughts?”

Sue blushed and cleared her throat, taking another stalling sip.

“Well, simply put... I don’t.”

“Susan!” Charity gasped accusingly. The other mom shrank meekly. “You know that’s not good for you. You deserve to feel good as much as anyone else!”

“I know. Really,” Susan assured her. “But the toys all seem silly to me and I was never one for… er, ‘doing it’ on my own...”

“Then find someone!” Charity urged sternly. “This is Queen’s Beach! You don’t have to marry them. Anyone off the street would love to be with you for a night. Hell, do you think I hired Leopold as my gardener because he’s good with a mower?”

Susan frowned thoughtfully as she remembered the buff and evenly tanned gardener that Charity had on call.

“It’s really not a big deal,” Sue muttered, even as she squirmed and fiddled with her fingers. “I just wouldn’t know how to start up a conversation like that…”

Charity clicked her tongue and grabbed her phone from the table.

“This won’t do. I’m not leaving my friend Sue unsatisfied just because you feel too guilty to say anything about it.”

“You really don’t have to,” Sue said quietly. She also distinctly wasn’t saying no.

“It’s nothing at all,” Charity dismissed as she finished dialing and raised the phone to her ear. “Hello, Leo? I’m going to need you a little ahead of schedule again. I need some help with the bushes again.”

---

Leo followed his employer through her lovely home. It was always impressive no matter how many times she’d led him down the same hall. She was always alternating with her decorating and arrangements. 

Leo was a tall, buff and tanned young man with short but full hair. Charity had hand-picked him from her applicants when it came to hiring a gardener. It was a rigorous recruiting session but she was incredibly satisfied with the results. His application even mentioned that he used to work as a stripper.

“Now you’ll be helping out a good friend of mine, so I expect your best behavior,” she explained. As she walked ahead of him, her dress shifted with her swaying hips and brisk stride.

“She’s a bit nervous about the whole thing and she’s been out of practice, so a perfect gentleman and a gentle lover is in order. If I hear so much as an unhappy moan out of her, I’ll see to it you’ll be back to doing squealing bachelorette parties.”

“You got it, ma’am,” the hunky gardener assured her. “I’ll show her a good time. Best behavior and everythin’.”

With a final nod, Charity opened up the doors to her bedroom. It was spacious with an equally roomy bed. Sue was sitting on the foot of the bed in just her black bra and panties. Seeing the new face got her to blush and clam up instinctively.

“Sue, this is Leo,” Charity laid out for her as she took her usual charge of the situation.

The mousey woman nodded, knowing about Charity’s arrangement for some time now. Charity came over and rested a hand on her bare shoulder.

“He’s at your disposal. I’ll be right here to give you some pointers and make sure things are running smoothly. Which reminds me…”

Charity pointed at Leo.

“I moved the lube to the second drawer. I didn’t want to mix it up with my skin cream.”

---

Sue was awkward at the start. She had muttered out several “Hi”s and “Thank you”s by the time Leo had stripped out of his shirt and sat behind her. His strong hands started to rub her shoulders until even the tense mother shuddered and sighed. She loosened up as he seemed to hit all the right spots, massaging her back and shoulders while he undid her bra. 

Leo had to sort of figure out his way around a weed-whacker, but he knew how to please lonely ex-wives. He brushed aside Sue’s long hair and kissed at her neck as his hands slid under her loosened bra. His big hands cupped her breasts, squeezing them lightly until her body tensed and pressed back against him. Sue let out a short gasp as she squared her shoulders.

“No need to keep it quiet, Susan,” Charity pointed out from her spot lounging on a comfy loveseat.

“It’s just us in the house, so there’s nobody to hide it from. And it’s quite appreciated when your partner lets you know you’re doing something right.”

“Sorry,” Sue muttered, a lusty breathiness to her words.

“And don’t apologize. It’s sex, not an exam. You’re both here to enjoy yourselves. You ARE enjoying it, aren’t you?”

“Yes,” Sue replied curtly with the same quiver to her voice. Leo ran his fingers past her nipples, giving them a light pinch between them. Sue gave a sharper gasp and arched her back, pushing her small, pale chest into his hands like they were begging for more.

“You certainly are,” Leo mused against her ear. Sue started to relax and shake off some of her rust as she tilted her head back, staring dreamily at her loaned lover until he kissed her. She moaned noisily as she wriggled in his groping grasp.

“Don’t forget to breathe, Sue,” Charity reminded her. Sue audibly sucked in a deep breath.  “And open up a little. Give the man some room to work.”

Sue wearily parted her pursed lips, allowing Leo to slip his tongue into her mouth. Her submissive nature went on as she let his tongue wrap around hers, manipulating it as he pleased. One of his hands slid down from her chest, brushing over her slim stomach before vanishing under her panties. 

Sue swallowed hard as Leo’s fingers massaged around her slit before pressing inside her. Having barely even gotten off over the last few years, her hips bucked against his probing hand. A husky “Mmmf!” came from deep in her chest as her thighs hugged around his hand.

“Much better,” Charity mused as she watched her lover for hire fingering her friend. Sue was starting to really get into it, warmed up just like Leo’s expertise had boasted. The brunette milf shut her eyes as she started to roll her hips slowly in response to the buff man’s strong and capable fingers. Charity couldn’t help but lick her lips a little at the sight. She was glad to see her friend happy, but it was reminding her of a few of her own steamy nights.

Leo slid out from behind Sue, easing her onto the bed as he held her steady in his arms. He maintained their embrace while peeling down her panties amidst his encouraging fingers. Charity was surprised to see that she had kept her bush well-maintained, carefully shaved down to next to nothing. Sue had loosened up enough to lift her leg and help his slide her panties off as she laid back expectantly.

Leo kept up his momentum as he shed his shorts. His impressive endowment made Sue swallow nervously but she spread her legs invitingly in front of him as she laid back on the pillow.

“There’s a good girl,” Charity encouraged quietly as she found herself rubbing a hand over her own thigh.

Leo carefully mounted and entered Susan as she tossed her head back and gasped. She bit her lip as Leo waited halfway inside her. She shut her eyes but nodded.

“Yes, please…” she mused, remaining polite even in her obvious arousal. 

Leo took her assurance and thrust the rest of the way inside her. Sue’s body bucked as she threw her hands around his torso, clutching with her fingers into his back. Her breathing grew high and heavy as he kept up his steady thrusting, rocking the Asian milf’s body subtly beneath him.

“Ohhh yes,” Sue panted as her modest features lit up. Her sexual fires were clearly being rekindled as she grew louder and more vocal. Her skinny hips started to bump up and down, adding to their combined arousal as her mouth was kept hanging open in awe of the moment. Leo took his time easing into her but as she clearly grew more into it he added more power to his muscular thighs until he was railing her hard enough to make the bed creak.

With her dry spell clearing up as her pussy grew wetter, Sue didn’t last long after Leo put his all into pleasing her. His careful but passionate fucking fulled her up and then some as the brunette bit her knuckle to relieve some of the building pressure of her pleasure.

“Oh fuck! Oh fuck!” the mousey milf squeaked a few times over before she shuddered bodily, clinging to the buff gardener tightly. Her pussy clenched and gushed around his cock.

“Ohhh my fucking god.” 

Sue empied her lungs with her long moan until she finally released her grip on Leo’s brawny body. Her head was spinning with pleasure as her fair skin went bright red.

“Glad to help, ma’am,” Leo said with a broad grin on his face. “You were real good yourself.”

“Well don’t overload the poor girl,” Charity cut in as she stood up from her loveseat. She undid the clasp to her belt and stripped out of her dress and glasses. Her slim but curvy body was lightly, evenly tanned all over with no signs of tan lines.

“Now if you’re through with her, I still have a bit of work for you to do.”

---

The blonde mom had been turned on from watching her favor to a friend turning into her own personal show. In fact, she’d gotten a little jealous about seeing her favorite boytoy in action with someone else, so she was quick to climb into bed and take Leo’s dick into her mouth. She sucked him off hungrily, tasting his precum leaking out as it mixed with Susan’s lingering cum.

The Asian milf was left in a daze from her first orgasm in a long time, but she crawled back over to rejoin the fun. Charity was surprised to find her thirsty for more, but she happily let her friend slide in as well.  

“It’s not often I get someone who can join in like this,” the wealthy blonde mused as she pressed a hand to Leo’s chest. She pushed him onto his back, even if it involved a lot of the chunky hunk moving himself how she wished.

“Here. Turn around. I never did get to try this one, but I saw it in a video. Now hook your arms… there we are!”

Charity and Sue each sat on one of Leo’s muscular thighs facing away from each other. They looped their arms around each other and clasped fingers to keep them steady. That left Leo’s warmed up cock nestled between their tight asses as Charity led Sue through bobbing up and down in their double hotdogging. The various juices lubed it up nicely so that the women slid easily along his cock, trapping or squishing it between their meeting buns.

“It’s really more about fluidity before power,” Charity offered as she smiled over her shoulder at Susan.

Having been fired up by giving Susan her due satisfaction, Leo couldn’t last in the face of such a sexy sight. The two milfs happily grinding their booties together and shuffling his dick around their cheeks got him to gush a warm, wet load up between them. Susan had been smiling meekly through the whole process, but she gasped and arched her back as the cum splattered back down on her and Charity’s outthrust asses. A second spurt followed it and left a warm streak of white across her back.

“Oh I should have warned you,” Charity chimed as she wiggled her ass from side to side. “Leopold can make quite the mess. I’d normally ask the cleaning lady to take care of it, but she’s only available for threesomes in the middle of the week.”

Sue gave a quiet laugh as she clearly loosened up, genuinely smiling back at the blonde. Charity snatched up some tissues and helped clean the brunette’s back off before Sue turned back to Leo.

“Thank you again,” she repeated her earlier sentiment. “But it wouldn’t be fair to leave our gracious host so unsatisfied.”

Susan crawled over to Leo’s dick, still wet, stiff and veiny from his orgasm. After a moment’s hesitation, she started to wrap her lips around its swollen head and gently sucked on it. Her eyebrows raised as she clearly tasted a man’s cum for the first time in ages. She took a little while to get used to the taste before she started to suck with more vigor, noisily slurping over his cock. She drooled heavily down his shaft as she rubbed her hands over Leo’s thighs.

“You don’t need to overboard, dear,” Charity offered as she turned to watch the show. 

“Keep it wet and all, but you don’t want that going back down the wrong pipe.”

Sue mumbled something as she nodded, tugging Leo’s dick along for the ride. Leo moaned and rested a hand on the back of her head to keep her against his shaft.

“And as much as we say ‘don’t talk with your mouthful,’ I find it helps work the tongue and get a little vibration in there.”

Susan lifted her head with a deep breath of fresh air, wiping some overflowing spittle from her lips. 

“Sorry. I just wanted him good and ready for you,” Sue explained. Charity raised a carefully groomed eyebrow before breaking into a smile.

“Well if he’s as ready as he looks… then I may as well go for something a little deeper than usual.”

Charity turned and moved to all fours, spreading her legs to brace herself on the bed. She patted her ass invitingly, her taut cheeks jiggling tamely after all those step-aerobics classes with her personal trainer. Leo’s cum still marked her cheeks, trickling down them as Leo caught her meaning.

The hung hunk took her hips and rubbed his cockhead along her asshole, rubbing the mix of cum and spit over Charity’s tight recum. She gave a low moan as she clenched her fists around the bedsheets, quickly loosening up until Leo’s dick slipped inside her asshole. The blonde took a few labored breaths as her stud made slowly deeper thrusts, wetting her hole as he made his way inside.

“Now the trick here is mostly to just relax,” Charity pointed out as she spared a glance towards Susan. The mousey Asian watched her with a small but satisfied smile.

“And lots of lube, but enough spit will do in a pinch. Or if you’re just feeling naughty… but it’s all unclenching and not fighting it.”

“Right. Relaxing,” Susan confirmed with a nod. “So like this?”

She leaned in front of Charity and took her by the chin, tilting her head up a bit so she could kiss her quietly but deeply. Charity broke the silence with her own lusty moan, stuck in place with Leo’s buttfucking as her breasts swayed between her arms. She parted her lips to let her friend make out with her as her hired lover plowed her from behind. Her anus clenched around him in fleeting peaks of arousal, but she certainly took her own advice in kissing her friend and loosening up in her building lust. Sue’s hands went beneath Charity’s chest and started to massage her breasts, groping the plump orbs before teasingly pinching her nipples to keep her moaning appreciatively. Unlike Susan at the start of things, Charity certainly had no trouble vocalizing her pleasure.

Charity could feel Leo’s cockhead bumping against the back of her clit when he shot his next load. Her jaw dropped into a loud gasp as his thick batch of cum accumulated in her bowels, adding more heat and pressure to her clit. She bit her lip and took a few more husky breaths as her ass clenched around Leo’s dick, hoarding seed away inside her until she finally relaxed again. His cum-caked cock pulled out of her, letting his orgasm leak out of her ass and down her thighs as she leaned back on her knees.

“It’s not always perfect,” Charity admitted. ”But it’s just the thing if you’re feeling dirty and aren’t prepared for something more intense.”

Susan nodded rapidly. “I understand. And about that move we were doing together a bit ago…”

“Oh, the double buttjob? I’ve actually heard it called a ‘Queen’s Beach Roller Coaster’ in certain circles.”

“Right. But is that doable the other way around? Like reversing how we sit on his… um, him.”

Charity put a hand to her chin while tapping a finger on her cheek.

“I don’t see why not. And I always respected your inquiring mind and creativity, Susie. Willing to give it a try?”

Sue nodded enthusiastically.

---

The milfs straddled Leo’s cock from either side, neither quite mounted on top of it. Instead, their labias pressed into either side of him, barely rubbing and practically kissing against his meaty erection. Their legs were tangled together, helping support each other’s efforts as their thrusts pulled the other in closer with them. The ladies leaned back, balancing and pushing on their palms as their parting pussy lips let their clits thrust out and grind against his cock. The stiff tower of flesh made it easy for them to rub up against while the thick veins provided a notable ribbed for her pleasure sensation. 

Charity gasped and shouted passionately as she arched her back. Her clit peeked out from between her lips, rubbing directly over the edge of Leo’s cockhead. 

Susan was still quiet about her lovemaking, but that just made her outbursts of gasps and moans come out louder still. Her heavy breathing quivered all the while as she rapidly pumped her hips against the upright hardon, leaving Leo with little to do beyond the occasional thrusts of his hips to keep things interesting for them. 

The girls ultimately hooked their legs together and pulled themselves in tightly, pressing themselves body to body with each other. Their orgasmic cries came with their breasts squishing together, squirting over Leo’s dick in unison. Their trembling and sweating bodies clung to each other tightly to ride out their min-dblowing orgasms. It drained the last of the women’s energy, finally letting go and collapsing onto their backs. They panted for air as their writhing, untangling legs rubbed one last load out of Leo, spurting it up across their legs. Susan gave a witless giggle as she cracked another small, dazed smile.

“So how’s that? Feeling a little more confident?” Charity pried knowingly.

Sue nodded from her splayed out position on the bed.

“Yes. Thank you,” she insisted.

“So you’re ready to hit the dating scene again? I might know a few well-to-do bachelors that are on the market…”

“Oh, not just yet,” Sue retreated. “I’ve still got a lot of things on my plate right now and I’d rather wait until things are settled. Buuuut…”

She cracked a smile as she snuck a glance at Charity and Leo.

“I’d be happy to get in some more practice until I’m ready. Is next weekend good for you?”

Charity tossed her head back with a proudly haughty laugh. “Perfect,” Charity chuckled. 

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