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

by TheWingman

Heart to Heart (Rouge Melody (OC))

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*Beeeeeeeep*

“Hey Calc, This is Julia. I want to give you my condolences for your loss. I know what it is like to lose a father, so I can understand your pain. Take as much time as you need from work. Don’t worry about a thing. Just… give yourself some time to grieve. Hope you’ll feel better.”

*Beeeeeeeep*

“Calc, It’s Ignacio. I’m sorry that your father had passed. He was a cool hombre. I remembered him making all sorts of jokes whenever I came over. Anyways, I have some good news. Me and Sunny Flare are expecting. If it’s a boy, we’ll name him in honor of your father. See you at the funeral. Take care, amigo.”

*Beeeeeeeep*

If there were any day where you felt like lying in bed for the entire day, today was one of them. Ever since two weeks ago when you lost your father, you, your mother, and many other family members had been making preparations for his funeral. It was one thing to hear someone close to you died, but it was another seeing them buried. As much as it broke your heart, it was something that had to be done. It made you feel like utter crap.

Checking your suit, you let out a big sigh before you drove off to the funeral home. Though the sky was a clear blue, the atmosphere wasn’t pleasant. Out of all the times you’ve had disagreements, in your mind or vocally, you never held any long-lasting grudge against him. In fact, you thanked him for putting you on the path to success, making you the man you are with the exception of a few other things.

Walking inside, various family members, friends, and others were all conversing with the air carrying the somber tone. With the exception of a few aunts and uncles shaking your hand among other things, you kept to yourself for the most part. All you wanted to do is find the funeral room and pay your last respects. As you did, you were greeted by a familiar figure, lavender hair and all. There stood Cocoa Lavender along with an older woman that looks almost like her, possibly her mother. Immediately, she noticed you approach and rushed to hug you.

“Calc!” she said as you returned the hug. “It’s been a while. I’m so sorry about your dad. I’m sure he was a good man.”

“Nice to see you too, I guess,” you deadpanned, breaking from the hug. “Thank you for your kind words, Cocoa.” Then, the woman noticed the two of you talking and wandered over. She looked like a spitting image of Cocoa, almost as if she was a clone in some way.

“You must be Calculus. Hi, I’m Lavender Blossom,” she introduced herself. “I know you’re already familiar with my daughter.” You didn’t respond, still feeling down. Blossom took a good look before wrapping you in a hug, nearly burying your face in her ample chest. “I know you’re upset. We did everything we could for your father. I’m truly sorry.”

“It wasn’t your fault,” you muttered. “I know you tried and that’s all that matters. Thank you.” Breaking away, you walked into the room where many people, including your mother, Ignacio, and Sunny Flare were conversing. But most notably, in a casket, laid your late father, cold and lifeless. Walking next to your mother, you put a hand on the casket, sharing a silent moment of reflection with her. There were a lot of things you regret having left unsaid to him and now you’ll never get the chance again. That was the heartbreaker for you and it made you choke on your emotions. Turning around, you gave your mother a big hug before taking a seat near Ignacio.

“How are you holding up, amigo?” he asked with a somber tone.

“Trying to, at any rate” you sighed. “It just seems… unthinkable that a day like this would pass. With that heart condition that ran in his family, it was bound to happen.”

“Well, the thing about life is that people come and go. The same goes for loved ones. Eventually, we all must make that trip.”

“Yeah, I guess.” Sunny Flare approaches you with her hair in a bun. You rose up an gave her a hug which she returns. “I got your message this morning. I’m honored by your decisions. Thank you.”

“We felt that it would mean a lot to you.” Sunny Flare said. “I’m sorry for your loss.”

“Don’t be. It wasn’t your fault.”

Soon, the funeral director came in and everyone took their seats with your next to you. The ceremony was an emotional roller coaster for the lot of you, especially your mother. When she came to the podium to say her piece, it was impossible for her to hold back tears that you had to escort her back to her seat. When it came time for your turn, you had your own degree of struggling with breaking down, but you managed to hold yourself together and deliver your heartfelt spiel about your father before giving a final goodbye. When all was said and done, the hardest part began.

You walked beside your mother and many others as you carried the casket to its final destination: a dug out plot near a small hill. Once there, you and the congregation shared your final moment of silence as it was lowered into the ditch. The lower it got, the more you felt your heart sinking to your feet. So this was it, the final goodbye. You’ll never see your father again and he’ll now be buried six feet in the ground. The only thing you looked forward to was the after party where you could drink your pain away.


You sat there at the counter, senses dulled from sadness and alcohol. The world around you seemed like a bit of a haze as the effects of your drinks got to your body and mind. Your pain from earlier seemed dulled, but your reasoning had taken a hit. Never eating, you just sat there, not wanting talk or do anything with anyone. Numbing the pain was all that mattered and nothing else. Looking at the glass, you grew angry and didn’t want to deal with your emotions.

“Another,” you muttered as the bartender walked by with a worried expression.

“Sir, I think you’ve had enough,” he replied. You however, didn’t take too kindly to his advice. With the alcohol calling the shots, your mind swayed to irrationality. You dearly didn’t want to dwell on having to bury family and the thought of doing so filled you with rage. Grabbing the man by the collar of his shirt, you got in his face and snarled.

“Make me… another Manhattan… or I’ll knock your fucking teeth in.” Panicking, the bartender relented and nodded as you let go.

“Fine, one more!” he said as started making your drink. “After this, you’re cut off.”

“Whatever,” you muttered as he handed your drink and walked off. “douchebag.” As you slammed your fourth and final drink, you watched on as the congregation socialized with your mom as she tried to keep her composure. As much as you wanted to comfort her, you were a drunken mess and you had your own mental health do deal with. How you were going to cope with seeing your dad off to the halls of valhalla was your guess and you hadn’t the slightest clue.

“A man drink like that and he don’t eat, he is going to die.” Hearing the voice, you turned around until you saw the source. Tall, rugged, orange hair, and a scar across his lip, it was hard not to forget him as Leo Starblaze, a friend of your father’s that served with him in the gulf war. “I hate to say this to you when you’re like this, but you look like hammered shit.”

“No offence taken,” you scoffed. “I take i-*hiccup* it you're not doing too well either, right?”

“Nah,” he said, taking a seat next to you. “Though it wasn't literal, me and your old man were like brothers. After we both got back from Iraq, I was his best man at his wedding. It always sucks to say goodbye.”

“No shit. So, what do you want?”

“Well,” Leo said as he cleared his throat. “I’m looking at you and I see an all too familiar sight. This isn’t how one should cope with grief. My aunt was an alcoholic and that quickly ruined her life. I’m concerned about this slippery slope you’re about to go down.”
“Heh. I find *hiccup* it funny that you show more compassion and emotion than that old bastard of a father of mine. He always kept me on a leash and rarely allowed me to go my own way. To think I wanted to be a cartoonist, that fucking asshole pushed me to economics and mathematics and shit. To hell with him!”

Though the alcohol dulled your senses, you could tell that Leo wasn’t pleased with your choice of words. He just lost a friend and to hear his son spitting on his name filled him with concerned anger. With much regret, he gave you a backhand across your face and grabbed you by the shoulders.

“Alright, I’ve heard enough!” he growled. “You just had to bury your dad and now you spit on his grave?! Shameful! Let me let you in on something. When your old man told me that your mom was pregnant with you, he made me your godfather, looking out for you when he’s not around! If your dad hadn’t been tough with you and pushed you to succeed, he wouldn’t be doing his job right! You have much to thank him for and the way you're going about this, you’re setting yourself on the path to losing it all! Are you hellbent on throwing your dad’s efforts down the drain?! If no, then get your fucking act together or you’ll be on the streets in short order!”

As much as you hate to admit it, Leo had a valid point. Much of your success was due to your father influencing your decisions. Though you wanted to pursue your aspirations, practicality had to take precedence. Realizing the weight of what you said, you hung your head in defeat, ashamed of what you said.

“Fuck,” you groaned. “I just... don’t know how to deal with this.”

“It’s okay, I’m not mad or anything.” Leo said, putting a hand on your shoulder. “I’m just concerned about you. If you need someone to talk to, I know of someone that would be more than willing to listen.”

“Who?”

“Rouge Melody. She was my son’s therapist when he went through the emotional hurdle of my divorce. Though she’s a family therapist, I’m sure she’ll have no problems with seeing you.”

“What good will seeing a shrink do?”

“You’ll never know, but she is great at what she does. If you’re afraid of her judging you on your thoughts, she won’t. Trust me.”

Pondering the advice for a moment, you had your doubts at first. Rarely do you express your emotions, even to a stranger. But now, you were in the position of not caring anymore. Maybe talking to this Rouge Melode lady would help. At this point, you were willing to do anything to find some semblance of solace.

“Alright, fine,” You groaned, feeling tired. “I’ll do it. What time?”

“She usually likes to do appointments at around noonish because her husband and daughter would be out and about.” Leo said. “Before I make the call, let’s get you home before you pass out. I’ll drive.”

“Fair enough.” Using his shoulders as support, the two of you got in your car and he drove you home. When you got there, you walked in, slammed a big jug of water and passed out on your bed. Though you were going to have a splitting headache in the morning, you hoped that the heart to heart with the therapist would help you find some closure.


You woke up, head throbbing with pain and eyes blinded by the solar light. Even with the immense amount of water you drank last night, you still felt hungover. As you struggled to get up, you picked up your phone and saw a text from Leo.

“Appointment is at 11AM. Hope you feel better soon.”

….and the clock read 10:15 AM. Upon realizing that, your brain did its best to kick into high gear, compelling you to do your daily morning readiness ritual. You put together your best day clothes, complete with a hoodie you got from a concert last year. Hopping into your Jag, you drove to the address he specified in another message, parking in its driveway. The house was made of bricks on the outside with a few small patches of flowers at the fore.

Walking to the front door, you gave a sigh, followed by a few short raps on the door. After a bit, the door was opened by a woman that was younger than you anticipated, definitely in her late 20’s. Her ruby-colored hair was styled nicely and hanged long towards the back. She had an incredibly welcoming smile and a pair of beautiful green eyes, very cute and beautiful. Though you would normally be flabbergasted at such a sight, your mind was still awash with gloom.

“Oh hey,” she said while shaking your hand. “You must be the one Leo spoke about over the phone. I’m Rogue Melody and it’s nice to meet you, Calculus.”

“Thanks,” you deadpanned, following her inside. The atmosphere of the living room was cozy and decorated with several plants, no doubt ones that calm the nerves. Taking your hoodie off, you sat on the couch, looking at your feet as you contemplate your emotions. “Sorry if I come off as short with you, ma’am.”

“Don’t you worry about it. As a psychologist, I have an understanding of emotions and I understand that you’re grieving. So please, lay down on the couch. Make yourself comfortable.”

Following her instructions, you took off your shoes and laid upon the sofa. To your surprise, it was cozy and felt good on your back. Your nerves began to relax as Rogue crossed her legs in her chair, letting you see a bit of her teal colored panties. As arousing of a sight it was, your mind was still in flux. You were unsure what or how to get it all out.

“Now Calculus,” she said as she grabbed her clipboard and pen. “Your godfather Leo said that you were having some issues with coming to terms with your father’s death. I just want to give you my utmost condolences for your loss.”

“I… do appreciate that, Rogue.”

“Okay. During his call, Leo mentioned that you, while under the influence of heavy amounts of alcohol, had some certain choice of words to describe him which included calling him a, pardon me: ‘fucking asshole’. Now, it’s natural to feel anger towards a family member over a perceived slight. I’m no stranger to it as my father-in-law Blaze Burn caused a rift with my brother-in-law Eternal Flames over getting married. So, I know what it feels like.”

“You don’t know half of it,” you said with a degree of venom. But to your surprise, she didn’t flinch, not even a word. “Though he made me who I am today, part of me hates him.”

“Well, what is the reason for your hatred?”

“It’s… hard to say.”

“Is it hard to say or do you not feel comfortable talking about it? I’m a family therapist and I know much about familial discord. You don’t need to wall yourself off in my presence. Now, what are the causes of your animosity?”

“I honestly don’t know.” Sensing your emotional barriers were showing some cracks, Rogue gingerly held your hands in hers. The warmth… your breath took pause over the feeling as your barriers weakened further. Even with your reluctance, she still was patient with you.

“Calculus, I know that losing a loved one is tragic, but, you don't need to keep your emotions pent up. It's okay to let them all out. I won't judge you in the slightest." She then reached to her side and handed you a small square pillow. “Let’s do this simple exercise. Pretend this pillow is your father.”

“What good will this do for me?” you asked.

“It’ll allow you a chance to vent your emotions, to let out what you left unsaid. Think of this as your chance for catharsis.”

Looking down the pillow in your grasp, you began to hear a familiar voice echoing through your head. Remembering its gruff tone, it was most certainly your father’s. Wondering if it was his spirit stalking you, the words he spoke were familiar to you nonetheless.

“Son, I know art was your passion, but you have to think about reality.”

“Goddamnit, you have to do better! Good grades are what’ll get you far in the world!

“Sorry, but the answer is still no!”

“Do better!”

“Son, words cannot express how proud I am of you.”

Snapping back to reality, you still held the pillow firmly in your grip. Your arms trembled the words echoed out. As your tears began to well up, you mind made up its mind and so did your heart. You felt no animosity towards him despite any and all contention. Upon that realization, your heart became wracked with guilt over all the things you said about him yesterday.

“Dad,” you squeaked out. “Th-There were times that I c-called you a hardass, asshole, and even worse. B-But, YOUWEREFUCKINGRIGHT! Thank you, I’m sorry!” Rogue, seeing you on the verge of tears, sat next to you and pulled you into a hug. Finally, your emotional barriers burst forth like a dam and you sobbed in her shoulder for a good while. She said nothing, apart from a shushing noise. As you did, your mind gave way to a feeling you needed since two weeks ago: relief.

“I know that leaving things unsaid tears one up inside,” she said. “As I said, you don’t need to emotionally hold yourself back here.” As your tear reserves dried, your mind became clear as the clouds faded away. Your breathing calmed as you broke from the hug. Rogue was right as you experienced catharsis, peace.

“Thanks, Ms. Melody.” You croaked. “Only later did I realize there was a reason for him being as such.”

“Well, your father wanted you to have a good life. Sometimes, your folks have to be tough to steer you in the right direction.”

“And he succeeded.” Taking a big gulp of some much-needed air, it felt like your troubles had left you. Freedom, freedom from your despair had come. Even as you looked upon her face, your heart still beat like a racehorse. Only now that your heart and mind was cleared did you acknowledge it.

“Is there something else on your mind?” Rogue asked. You looked down at your feet once more, still nervous to look at her. “Does it have something to do with me?”

“Well, actually, it does.” You admit, still flustered. “You look rather nice.” Rogue was at first, taken aback by your compliment but regained her composure with the blink of an eye.

“Why thank you, Calculus,” she replied.

“But, uhhhh, If you don’t mind, may I… give you a kiss?”

“A… kiss?” She ponders as her legs shift about. “Well, intimate contact is known to be a great stress reliever. I don’t see why not.” Slowly, Rogue cups your face with her hands as your hands latch onto her waist. For a moment, it seemed as if time held no meaning as your lips made contact in a display of affection. Steadily, your woes melted into nothingness as you broke away for some air. That was short-lived when she pulled you back for another with you hovering over her. She was an excellent kisser and a beautiful woman. To whoever has her for a wife is a lucky bastard for sure.

“Calculus,” Rogue breathly moaned. “I want you to take me!”

“Why?” You asked back. “Aren’t you married?”

“Yes.”

“Then why? Don’t you love your husband?”

“I do love him dearly. It’s just that we’ve been trying hard to give my darling Blitzwing a sibling, but we don’t know why it’s not working. You’re quite a virile looking man and I still can sense a bit of stress about you. How about this: I’ll relieve you of your stress if you give me a baby.”

Sometimes, you have to appreciate how forward some women can be. You remembered the time you got something in exchange for knocking your boss. Being down that road many times, you’ve begun to lose count of how many illegitimate children you’ve potentially sired. With this, you had a feeling that Rogue would have a cover story if anyone asks questions. Plus, she had a nice MILFy body for a woman in her late 20’s, the envy of many. Most of all, your mind needed release and Rogue would be the ticket.

“Okay, done deal,” you replied as you dove in for another kiss but grinding against her crotch as you did. Before your hand even reached her panties, it was stopped by the firm grip from her hand.

“How about we take this to the floor, Calculus.” She stated. “It would be easier to clean the carpet than a couch.”

“Fair enough.” Holding her tightly, you rolled down onto the floor, sheltering Rogue from the impact with your hand before resuming the kiss. Being above her netted you a nice view of her beauty. Slowly, her hands drifted to your crotch and cupped your throbbing erection delicately. Good lord almighty, she’s making you crave her caress that badly. Pulling away for some fresh air, she gently pushed you onto your back as she got on her knees and eying your clothed junk. Here comes the inevitable blowjob.

“I think I know where this is going,” you snarked as you unbuckled your jeans. “Been through the same old song and dance.”

“So, you have experience?” Rogue asked.

“Plenty, but it’s a long story.”

“I’ll bet.” Pulling down your jeans and undergarments displayed plenty of that experience before her eyes. The sight of your cock made her break a few droplets of sweat. Flexing it a bit was the last straw for her as lust blocked out her reason. She pulled off her sweater to reveal her nicely shaped tits, jiggling about like balloons. “So, like what you see?”

“Very much so.”

“Well, let me put them to good use.” Goodness gracious almighty, Rogue has some soft tits. Your eyes rolled to the back of your head as you struggled to contain yourself. They felt so soft and warm like bags of pudding. Feeling those chest pillows mash around your erection was priceless, felt so incredibly right. As much as you try, there was nothing within your reach to grab on to. For now, you were being taken for a ride and you have to endure it all.

“Good fucking god, Rogue!” you gasped as you felt your orgasm starting to build up about half-way. “You must really drive your husband crazy with this! OHGODYES!”

“That is sorely an understatement, sir.” She shot back as bits of precum start leaking out. “I can tell that your getting close, bit by bit. Feel free to hold back for as long as you would like, but I want your seed to cover my mounds.”

“Heh, I’ll be happy to oblige.” Biting your lip, you braced yourself as breasts went faster and faster. So much pleasure, pulsing through your nerves and back, it was almost unreal how good therapeutic sex would feel. You struggled to contain yourself as your cock grew ever more sensitive by the minute but it was inevitable. All you had to do was let go and let it flow. It quivered and pulsed as it sprayed Rogue’s ample chest with your thick white seed. You laid back, gasping and breathing as you rode out your orgasm, feeling as more of your stress left your being. You were in bliss if only for a moment.

“Holy shit!” You breathed as you sat up, taking off your shirt. “For solely a titjob, that was something.”

“It’s as if I have the magic touch,” she said wiggling her fingers. “But as much as you loved it…” She lifted her legs up and removed her skirt and soon her panties down to her ankles, revealing her salivating flower, hungry for attention and cock With a flick of her foot, it flew onto your face and filled your nose with the musky scent of her sex. Sweet, caring, yet kinky, Rogue was truly one in a million. “My pussy needs some love.”

Mouthwatering, heart-pounding, and cock quivering, the sight and scent of her moist folds was overwhelming to you. You wasted no time in diving towards her crotch and lapping away at her labia with your tongue. Occasionally, you teased her clit with a few passes while never licking it for long. For how good that titjob felt, you wanted her to beg for your meat. There, your brain hatched an idea, one that was based on familiar territory to you.

You stuck your tongue inside her, but only the tip. The way she writhed about and moaned told you it was working to great effect. Occasionally, your breathing on her clitoral nub sent pulses of ecstasy throughout her being. Just eating her out like this was enough to reinvigorate your spear back to fully erect. But you pulled away, much to her dismay. She gave you this puppy dog look that spelled ‘why’. Little does she know, you had her in the right spot for a proper fucking.

“Calc, I was so close,” she breathed. “Why did you stop?” Rogue’s mood changed from dissatisfaction to speechless as the tip of your shaft prodded her entrance. From your earlier display, she was sufficiently lubed up. Even as it felt slick to slide your shaft into her cave, It felt snug inside her. The look on her face as she felt the pulsating warmth of your cock deep inside her was amusing.

Giving her a quick peck on her lips, you began to thrust in and out of her slick hole. Her breasts bounced up and down in rhythm with your movements, hypnotic and erotic to see. For a MILF in her late 20’s, she sure looked and felt good. Skin to skin, lips to lips, your sweaty bodies bumped and ground against one another in a display of lust and carnal release. You’ve been miserable for the past several weeks since that fateful day and to say your spirits are no lifted would be putting it a bit lightly.

“NNNNGHHHHH! OH FUCK!” Rogue moaned loudly as her inner walls started to clamp around you. “ARE YOU CLOSE YET?!”

“Not quite!” you groaned back.

“GOD FUCKING L-OOOHHHHHHHH!” With her scream, her inner walls clenched around your scepter and a gush of her lust fluids erupted from her folds. Even as the pungent scent of sex and sweat hit your nose, you were not done just yet and you still had a bit more to give. You kept pumping and pumping in and out of her as she rode the remainder of her orgasm. Each and every time it made your nads sensitive and uncomfortable, but you wanted to hold out as long as you could for her. Sensing your fatigue, Rogue placed a hand on your cheek with a reassuring smile on her face.

“It’s okay.” She cooed. “You don’t have to hold on for so long for me. Go ahead, give me your cum. Give me a baby.” That was it, the straw that broke the camel’s back for you. Hilting yourself, your cock quivered and pumped loads of your life-giving seed into her fertile womb. The sheer volume of your load was enough to give her belly a slight yet noticeable pudge and leaving you winded, collapsing next to her. As you breathed, you’ve felt your aggravation leave you, but you still felt a bit wound up; nothing that you couldn’t manage.

“So, how did it feel pumping that load of yours inside me?’ Rogue purred as she gave your cheek a kiss.

“Liberating,” you quipped, sitting up. “It felt good but I still feel a bit uneasy. All in all, that felt great.”

“Well, since you still feel a bit under the weather, why don’t you take this day and have it be yours.”

“Well, I usually have a pretty open schedule. What would you suggest?”

“If it’s your thing, perhaps a day at the spa will put you in the right spot. I know of this great place in the downtown area called Canterlot Heavenly Spa. Though pricey, it’s worth the price.”

You recognized the name as soon as it left her lips. You’ve been there once before with Ms. Harshwhinny the day you knocked her up. Though you weren’t usually weren’t the one for a spa, your trip there certainly warmed you up to it. Plus, your night with the twins who ran that place certainly topped off the whole experience. It would be certainly nice to have fun with them again.

“Fair enough,” you said as you stood up. “But I can say that we can’t have these sorts of appointments due to… ethical reasons.”

“Good call.” Said Rogue. “Well, if you still need a therapist, I’ll give you a business card for my friend Dr. Cerebellum. She has an office uptown. Go on and get in the shower first. I’ll run a steam cleaner over the area a bit.”

Nodding, you grabbed your clothes and jumped into the shower, giving yourself a good scrub down. Another day, another MILF to add to your score. With your mind at ease for the time being, your mind felt much clearer than usual and at terms with your thoughts of your father. All in all, your were sound of mind and eager to meet up with the spa twins again. It seemed like a long time since you’ve shagged with them. You wondered how they were doing.


Author's Note

Well, with tragedy comes a need to cope with it, whether it be talking with someone... or other means. Sorry I was a bit late to get this chapter out and I hope you'll enjoy it. The OC in question is owned by my friend Israel Yabuki.

Also, I'm going to take a month long hiatus from this story to devote efforts to some of my other stories that I've not updated in a good while. But don't fret, I'm not abandoning this story in the slightest. Enjoy reading.

EDIT: Removed and changed the names of characters at the OCs owner's request.

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