Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars

by TheWingman

MILFlove's 2 Weeks off - Part 3: Mother May I (Stellar Flare)

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The lights go out and so does your AC. Going around your house, checking the appliances and circuit breakers, you confirmed the power went out. Just fucking great, just as ou were about to waste some hellspawn, lady luck rained on your parade. Checking outside, the same could be said for the neighborhood. Using the almighty power of cellular data, you found online that a substation catching fire was the cause.

“Fuck,” you whispered. “Hope I can spring for that generator.”

Just as you were about to grab your car keys, you heard a knock on your door. Opening it revealed a familiar face: Sunburst, an old college buddy of yours. After college, you thought it was the last you would hear of him but no. He moved into town a year back and since then, you’ve been having monthly gaming tournaments with Button Mash with some DnD thrown into the mix.

“Hey Calc,” he greeted. “You’ve heard about what happened?”

“Yeah,” You shot back. “And it looks like it’ll be a day or two until they can fix things. I was about to make a run up to the hardware store for a generator.”

“Sorry to burst your bubble, but that store is on the same grid as your place.”

“Really? Goddammit. I was just about to play Hellhunter Forever.”

“Well, my place has power. You can bunk there for the night if you want.”

You never entertained the thought of spending the night at a friend’s house. You always found it an awkward situation if it came down to it. But, desperate times call for desperate measures. Knowing that he too pre-ordered the game, your choice was clear as rain. Nodding your head, you agreed and left in his car to his house on the other side of town.

Sunburst’s place, from the outside, looked rather plain like the rest of the residences on his block with the exception of a couple Batman lawn ornaments and a Captain America shield on his door. Still, it looked like he kept his lawn nice and tidy.

“Calc,” He sighed. “I must warn you… I have a relative visiting me for the weekend.”

“Really? Why the long face? Is it your twin sister Sunset Shimm-”

“Errr… no.” Sunburst turned the doorknob. “It’s a little complicated.” The second the door opened, your ears were greeted by a sing-songy voice.

“Welcome back, my wittle Sunburst!” There, in his living room, sat a woman, more than twice the age of Sunburst. Her getup and hairdo gave off the look of one of those pin-up models from the 60s and 70s. It didn’t take putting two and two together to identify her as Stellar Flare, his mother.

“Hi… Mom.” Sunburst groaned in embarrassment.

“Aww, you shouldn’t have to be embarrassed about your dear mother.” Stellar Flare pinched his cheeks, much to his displeasure. Soon, her gaze turned towards you. “Oh, and I see you’ve brought a friend over to play. Who might you be, Mister?”

“Calculus, ma’am.” You cleared your throat. “I’m an old college friend of his.”

“Oh yeah, I remember him talking highly of you back then. Although, I half anticipated him bringing Starlight Glimmer over to announce they’re expecting.”

“MOOOOM!!!” Sunburst yelled in annoyed embarrassment. “Please, don’t talk about stuff like that when he’s here!”

“Oh come now, is it that much of a crime to voice my desire for grandchildren?”

“No, just not in the company of my friend!”

“Oh please, would you mind if I count the times that you brought Starlight-”

“Mom.”

“And heard the creaking of your bed from the hall-”

“Mom!

“You have to admit that the walls aren’t that soundproof as they should’ve been.”

“MOM!!!”

“It’s alright, broski,” you said, patting him on the back. “I’m no stranger to the intricacies of the ol’ horizontal hokey-pokey.”

Sunburst was left flabbergasted at the situation before him. Over the course of your friendship in college, he did mention some bits of him having some intimacy with Starlight Glimmer. Over time, you trusted him enough to talk about some of your ‘conquests’. With the first mention, he was left dumbfounded at first. But, he eventually changed as you explained how they all happened. Still, he was left somewhat puzzled.

“See, no need to be embarrassed. We’re all adults here.” As you sat down, You found Stellar Flare sitting next to you on the couch. She sat so close to you that she was a hair length away from having both your legs touch. The distance made you slightly uncomfortable but not to where it was visible. If there was one thing you’ve adapted your body to, it’s being able to hide your lust. “So, what brings you over to my son’s place?”

“The power went out in my area and I neglected to buy a generator,” you explained.

“Awww. no need to fret. We’ll both have some fun together tonight.”

“Well, I wasn’t about to change my definition of fun to slowly cooking like a roast in my house.”

“Good thing I had the sense to install centralized air.” Sunburst said as he reached for his phone. “I'm going to order some chinese. What do you want, Calc?”

“General Tso’s chicken and chow mein sounds good.”

“Alrighty then.”

After phoning in dinner, you, Sunburst, and Stellar Flare spent the better part of the next twenty minutes chatting and making the air alive with conversation. As ever, Stellar Flare was intent on telling some rather crazy stories of her son during his youth. You found those stories funny, much to his chagrin, especially the one where he got hyperactive after eating some particularly sugary candy at a mall one time and the commotion he started.

Eventually, dinner had arrived and it was still piping hot as if it came straight from the pan. Hunger took over as the three of you dug into your meals with little abandon. It was rather weird that you felt hungrier than usual as of late. After dinner was finished, you and Sunburst began playing his copy of Hellhunter Forever and it was ever so glorious. Slaying all manner of hellspawn was like a symphony apart from the fact that Ms. Flare occasionally dropped in to chat.

Stellar Flare, apart from a different getup, looked to be a typical run-of-the-mill cougar that you were used to, but there was something different about her like a different vibe she gives off. It was motherly, more so than the last ones but with a hint of playfulness. Yet, it all masked a woman with plenty of experience under her belt and the guile to match.

Soon enough, night had arrived. Though it was 9PM, you preferred getting to bed early. Your day took a bit of a nose dive but it was all inconsequential in hindsight. Taking one of the guestrooms, you found that the mattress was firm yet cozy. Lord, did it feel so good for your back. It was like sleeping on a cloud. No sooner than when a good half of an hour passed that the comfy mattress dragged you by your toes to slumberland. You slept like your soul went to the great beyond.


You had no clue to the amount of time that passed as your eyes slowly opened to the room shrouded in darkness. The bright light of the moon nearly blinded you as you adjusted your sight. Rubbing your eyes, you noticed a moving mass between your blankets, right between your legs. Your spine began to shiver as you ponder what it could be. Slowly, you lifted the blankets to behold…

… nothing, except Stellar… Flare… fondling… your package. Dafuq?

There she was, the mother of one of your college buds was copping a feel of your unit. You were frozen in place as only one question plagued you.

“How the fuck did she not wake me?!”

Just as you were about to open your mouth to say something, one of Ms. Flare’s hands reaches out and holds your lips shut, unable to make a sound.

“Hush now, my guest.” She cooed. “Just sit back and let mama take care of things. There’s no reason to be upset.” The way she handled your cock and balls felt like the silkiest of velvet stimulating every length of nerves in your crotch. Clearly, she was no slouch and she demonstrated her expertise by removing your boxers without waking you up. Fuck, she is good.

“Well Ms. Flare, I ain’t complaining.” You moaned with ecstacy. “Whatever you do, don’t stop.” With a chuckle and smirk, Stellar Flare stopped her ministrations and crossed her arms, much to your dismay.

“Well, I’ll keep going if you do one thing for me.” Is she really doing that, teasing you? You were used to women being up front and wanting to hump you without any delay. But never, ever, were you teased. Then again, it felt fresh to go at it with some cougar that was playing hard to get. It should be fun and challenging and a break from the norm.

“Alright, what are your demands?” you asked.

“I… would like you to call me… Mommy.” That last word rang in your ears. Is she seriously asking you to do some roleplay, incest roleplay no less?! “Well, Mommy’s waiting.”

And it looks like she wasn’t going to easily back down either. Though you’ve engaged in many sexual taboos, pretend incest was one thing you’ve never considered, even though you’ve gotten your jollies off to two sets of sisters doing it before. Still, like always, the more you thought about such an obscene and morally questionable act, the more it made your pecker tingle with excitement. The thought sounded wrong but erotic at the same time.

“Okay, M-M-Mommy.” You mumbled.

“Louder so I can hear it clearly.” She commanded.

“Okay, Mommy.”

“Better.” She resumes her ministrations on your package, now more sensitive and eager for pleasure. From just a slight touch of a fingertip, your balls quivered, causing you to grunt in erotic pain. “Awww, does it hurt when I touch you like that? Would you like mommy to kiss that boo-boo for you?”

Holy fuck is she charismatic. Her unique quality was starting to shine through. She has the body, nice for an average MILF. But, where she lacked in any specialization of any particular part of her anatomy, she makes up for it with heaping helping of charm. She must’ve driven her husband, where he was, crazy during their nights of passion.

With a “Yes, mommy” from you, her lips made contact with your nutsack, pelting it gingerly with the softest kisses imaginable. She eventually started including her tongue which led to her licking up and down your shaft. Soon, the blowjob began in full, smooth and sensual and leaving you nothing short of speechless. You wanted to grunt loudly but the risk of repeating what happened last week was enough to shut you up. You could only grunt in your mind as Stellar Flare helped you see heaven.

The feeling of her velvety tongue slithering around your knob was more than you could as your balls blasted the inside of her mouth with hot, life giving seed. Gasping and gyrating your hips, the wild ride of your orgasm reached its peak before it steadily landed for a soft touchdown. As you felt a sucking motion on your cock, you knew then and there that she swallowed your entire load. Impressive.

“There we go, the boo-boo is all better,” Stellar cooed as she took off her shirt to reveal her supple and firm chest balloons, leaking with milk. “Since mama made you feel better, how about you help me with something?”

“Like what?”

With a smirk most mischievous that was masked by a motherly aura, Stellar Flare sat on her knees as a musky scent pummeled your nose. Her wet and puffy snatch was dripping with arousal and waiting to be pleased. You were compelled ny instinct to sit up and prepare to dive into her honeypot…

...only for her to send you back onto the bed with a flick of a finger.

“Now now, it’s best to enjoy your dessert, young man.” Before you knew it, her winking vulva hovered above your face, slightly hairy and winking with excitement. There, she lowered herself on your face with her wet sex landing on your mouth. Facesitting, strange, new, but exciting to try. “Go ahead, dig in.”

Upon her command, you began lapping up her juices, on and around her flower. The occasional brushing of her clitoral nub produced some sharp loud gasps. You could tell that the poor MILF hadn’t seen any sort of pleasure in quite some time. As you pressed on your tongue assault with plenty of nibbles on her clit, Stellar Flare petted you gingerly on the head, howling into the night.

“Oh yes, OH FUCK! GIVE MOMMY WHAT SHE NEEDS! OH YEAH! FUCK! MMMMHHHNNNN!!!”

The moment you pushed your tongue in her vagina, time seemed to have froze for the motherly cougar. Then, her moans became gradually coarse and longer in duration. You thought that some MILFs were sex hungry women but Stellar Flare… she was starved of it like she was trapped on an island. Of course, from how quickly her pussy dripped, It didn’t take to long for her climax to speed across the finish line, soaking your face with her juices. You endeavored to lap up as much of it as you could but weren’t able to get it all. After her mind became lucid once more, she got off your face and laid beside you, panting and fanning her face.

“Oh yes, good boy. You did well.” She turned her back to you, giving her firm ass a jiggle. “Good boys like you should be rewarded. You must feel a little cold being in the nude. Come and I’ll give you… and that thing some warmth.”

Needing no introduction and with an excited erection, you scooched up behind her and slid your spear inside her cunt. Goddamn mother of mercy did her pussy feel so good. Holding her tight like a tree, you began thrusting in and out of her honeypot. Spooning a seasoned woman certainly brings back memories of the last time you did it, even acting out that fantasy with Cadence years ago. The feeling of such intimate skin to skin contact surely brings a warm and fuzzy feeling to your nads. The constant jabbing of her cervical entrance only made her vaginal walls tighten further around your cock. You know she was ready to burst and so were you.

With a few more mighty thrusts, your pole convulsed as hot milk spewed forth from your balls. The feeling was incredible, holding the most motherly MILF you knew in the spoons while ramming at her cunt. In the wild throes of yours and her passion, You surprised her with a deep kiss and quickly invading her mouth with your tongue. As the last of your seed trickled out of you knob, you slid on top of her and rested your head on her breasts.

“I have to say…” Stellar Flare said as she petted your head once more. “You did a good job, Calculus.”
“You’re welcome. But, didn’t he hear us?” A slight chuckle was heard upon utterance of your question.

“Oh, you don’t need to worry about that.”

“Why?”

“Funny story. While I was visiting him last year, he caught me pleasuring myself with a dildo. I guess the reason why he didn't complain was he didn't like the thought of me naked. Though, I bet even his headphones can only do so much against my moans. Oh god, I'm so loud.”

“Nah, it's alright. The sex was well worth it.” Your mind began to feel heavy as your eyelids began to shut. You were about to fall asleep when a thought occurred to you. “I hope I don't end up getting you pregnant.”

“I'm already on birth control. No need to worry.”

“Good to know.” With a yawn, you completely went back to sleep, satisfied and exhausted. Contrary to what she said, the “birth control” Stellar Flare said she was taking was the exact opposite.

“Sometimes, if your dear son is slow to give you grandchildren, time to take matters into your own hands. But I will admit, his friend was amazing. I’m certainly glad Elaina told me about him.”


Author's Note

Here's the chapter dedicated to MLP's newest an motherly MILF to date. I honestly had a lot of fun characterizing Stellar's personality and writing it in a way where it also encompasses lust. To be honest, I've been rather fond of Stellar Flare as of late. Anyways, I hope y'all enjoy this. There's more to come and more MILFs to be pleased.

Preview Time:

"Alright, Mrs. Velvet," You said. "I propose a challenge."

"What kind of challenge, young man?" Velvet asked back.

"A game of Rock Paper Scissors. Best two out of three. If you win, you can have the book and I won't complain. If I win, I get the book... and that sweet perky ass of yours."

Twilight Velvet pondered your words for a bit. She really wanted to read that book you were about to rent. But, the lack of satisfaction from her husband has been driving her crazy. With her pussy quivering in excitement going toe to toe with her desire for the book, She agreed to your challenge, knowing that it's a win-win situation for her.

"Alright, you have a deal."

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