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

by TheWingman

A Boss's Adoration (Ms. Harshwhinny Revisited)

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You wake up, looking out the window of your room. Clean and serene, it was a beautiful complement to the rising sun. The many get well cards from your family and various loved ones still stood atop the drawer on your left. As you sat up, The phone next to you began to ring. Answering it, you were greeted by a familiar voice.

“I take it that you’re awake by now,” Ms. Harshwhinny said.

“That I am, Julia,” you replied. It was always a pleasure for Ms. Harshwhinny to look out for you, being her assistant and all that. Still, it was an unusual departure from her strict and stern demeanor. All in all, you take it as you see it. But today, you were in a good mood that you’re being released from the hospital. “So, the docs are cutting me loose. Though I still have this damn cast.”

“No need to be so upset about it. Within a few weeks, you’ll be back to your old self. I’m just letting you know that I’ll be picking you up within a few hours.”

“Ah, wonderful,” you breathed with jubilation. “So, I can expect to see you her at around noonish?”

“Correct,” replied Harshwhinny. “No need to rush things. Just take it easy and you’ll be fine. As I’ve said before, you’re in good hands. I’ll see you soon. Take care!” With that last part, her voice carried a sing-songy tune to it. Part of you wonders about her change in attitude, whether it be her pregnancy throwing her hormones out of whack or genuine gratitude for helping her have a child. Still, you consider her a pleasure to work with, thankful for giving you a position worthy of your skills.

The door then opened and through it stepped Redheart. She looks upon you with lidded eyes, the same eyes you’re familiar with. Ever since last week that you’ve started sharing lustful nights during your sponge baths, she gives you that look every single time. But that look soon gave way to that of professionalism as Dr. Horace entered the room.

“Good morning, Mr. Crunch. How are you feeling today?” Horace asked, breaking the silence.

“Damned happy that I’m going home,” you shot back.

“Heh, I can certainly tell,” he said as he flipped through his clipboard “Well, all you really need to do is to get ready for the day, sign some discharge papers, and you’ll be good to go.”

“Done deal,” you muttered.

“Okay. Well, get ready for the day. Redheart will wheel you out to the front desk when you’re ready.”

“Alright. Thanks, doc.”

Once Dr. Horace left, Redheart helped you out of the bed and into the bathroom. As before, she washed every inch of your body, including your junk. Even though the moment gave you a raging stiffy, you both thought it best to not to start screwing then and there, as much as you both want it. Like always, she did a good job and helped you into your casual wear. It felt good to be in nice and comfy clothes after weeks of being in a patient’s gown.

Before you knew it, another nurse arrived with a wheelchair and a pair of crutches. With assistance from both her and Redheart, you were seated on the wheelchair, relieved at your change in mobility. But still, you had to stay put until your boss arrived.


As you were busy watching TV, staving off the long crawl of boredom, you heard a familiar click-clack of steps from down the hall. Turning around and facing the door, your sight was soon greeted by a familiar blonde-haired sight. Right away, she rushed over to give you a hug, pressing her rotund belly against you.

“Good to see you, Julia,” you whispered as she broke the hug.

“Likewise,” she replied, dusting herself off. “Now, let’s get you out of here.”

With the aid of some nurses, you were pushed to the front desk in the lobby. Once there, you’ve signed the papers, setting you free after weeks of confinement. From there, you were helped into Harshwhinny’s SUV along with all of your stuff and you were soon off and away.

“So, how does it feel to finally be out and about?” Harshwhinny asked.

“Good,” you replied. “But damn, I absolutely hate hospital food.”

“Well, you be pleased to know that we’re stopping at my place for lunch. We’re having butternut squash ravioli with a creamy garlic sauce. It was a recipe from my mother.”

“Please, you’re making me hungry, Julia.” You laughed, as does she. For the rest of the trip, the two of you made pleasant conversation with the occasional talk about work. From what she told you, you were granted the go-ahead to work out of your house until your leg was fully healed. All it will amount to is answering calls and e-mails from the financial department with the occasional meeting. Thank goodness for video conference technology.

Soon enough, she pulled up to a modest looking place with an orderly looking garden at the front. Being helped inside through your crutches, the interior shared the same aesthetics as the exterior. You’d figure for a woman as rich as Ms. Harshwhinny would live in a lavish place. But hey, to each their own.

“Come, sit down on the couch” said Ms. Harshwhinny. “I’ll be right back with lunch.”

Nodding, you carefully seated yourself on the couch with your crutches as support. It felt good to sit upright on something that wasn’t a hospital bed. You leaned back, closing your eyes as you took in the atmosphere. It felt tranquil, peaceful, and cozy enough that you could just fall asleep with not a care in the world. However, the scent of butternut squash and garlic kept your senses alert and your hunger growing.

“Lunch is up,” Harshwhinny sang, walking in with two plates of creamy pasta goodness. You both chowed down on the plate of pure comfort. Sweet and savory, it was amazing, reminding you of Sunny Flare’s stir fry. Every bite and morsel brought warmth to your soul. The best part of it was the creamy garlic sauce that had notes of parmesan. It certainly was better than the stuff that you had for weeks.

“Gotta say, never thought I’d like butternut squash,” you said, wiping bits of sauce from your lips. “I’m honestly very surprised.”

“Well, my mother knew cookery like it was at the top of her head.” Mused Harshwhinny. She then scooched closer to you. Your face grew a little red but it wasn’t anything out of the ordinary between you two. Carefully, she placed your hand on her belly, running it across its surface. Soft and smooth, it felt warm to the touch. As you ran your hand across her tummy, you felt a slight bit of force pushing against it. It was clear the life growing inside was getting antsy.

“Heh, I think it knows who you are,” she chuckled.

“You’re going to be a great mother, Julia,” you replied with a tender voice. Still, some thought kept eating at you. After your vacation months ago, she treated you as if you were a business colleague. Now, it’s as if she views you as something beyond all that. It only really happened after your accident when she would visit you every other day. For you, it could be anything. “But, why are you acting so friendly towards me?”

“Well,” she started, clearing her throat “I suppose I’ll be honest with you. I would’ve attributed my behavior to my fluctuating hormones but that would be an excuse. Ever since you impregnated me months ago, I’ve felt this sense of gratitude towards you. As for our arrangement, I was right to pick you. Your skills have proved most useful. When that accident happened…”

There was a hitch in her voice as she took a small pause. At a glance, she appeared to be calm and collected like she always was. Tilting your head, you noticed something small traveling down her cheek, a tear. Why was she crying? Was it for you? If her earlier statement was an indication, you knew right away what she meant.

Resting your arm on her shoulders, you gently pulled her into a hug, taking care to not hurt her baby. Rubbing her back, you gently rocked her as she cried a bit in your shoulder. Shushing her, you reassured her that everything was alright. Still, she was uneasy.

“I just… I didn’t want to lose you! I’m carrying your child and you’ve been the best assistant I've had! I’ve grown fond of you and I wasn’t about to let you go!” If there were anything you’ve learned since you started working for Harshwhinny is that she always meant what she says. Here, she’s spilling her guts to you, her assistant that makes sure nothing is wrong in the workplace. Still, it was a terrible sight to see her upset, knowing the effects it had on her baby.

When all seemed calm and peaceful, a hand gently reached for your cheek and you were pulled into a kiss with a blink of an eye. This one felt different than the last time you both did it months ago. It lacked purpose, fueled purely by emotion. It was also easy enough to lose yourself in the moment. Though you couldn’t move, Harshwhinny was kind enough to climb onto your lap. For the next few moments, you shared a silent yet powerful moment of intimacy. It felt so sudden yet it felt so right.

“Do you feel better, Julia?” you whispered.

“Much better,” she replied, “Don’t ever scare me like that again.”

“Well, I know better to not piss my boss off.”

“Good. But as much as I like our little moment, I would like to go somewhere more comfortable for both of us, like my room.”

“Good idea.” With her assistance, you got on your crutches and followed Harshwhinny to her room down a short hall. Her bed was a large one, no doubt could fit two or more people. At its head was a mountain of pillows of varying shapes and sizes. It looked like a big fluffy cloud to you. You carefully lowered yourself on it, slow and steady. Just when you thought that she would join you, she does the opposite and retreats to her bathroom. For moments, you wondered what she was up to before your answer walked back out.

Ms. Harshwhinny stood there, completely naked and holding a bottle of oil. Putting two together, your dick tingled at the thought. She wanted a massage, to have your hands spread a relaxing oil all over her pregnant body.

“Heh, I know you’re excited but I would much rather you be nude for this.” Following her orders, you removed your shirt while she took care of your undergarments. Once those were off, your cock sprang tall and proud. Harshwhinny smiled at the sight of it, recognizing it. “It’s been a while since I’ve had that cock of yours. I hope you won’t disappoint.”

“You know me, I never do.”

Handing you the bottle of oil, Harshwhinny laid back on you and spread her legs. Pouring a small amount of the liquid on her rotund belly, you worked your magic as you gently massaged the oil into her skin. Without much friction, it felt like a nice slide. Judging by her resting her head on your shoulders and a relaxed sigh, she dearly wanted this, especially from you.

“Ooooohhh yeeeesssssss,” Harshwhinny moaned, “that’s the ticket. As much as you like my belly, my breasts would like some love.”

Shifting your hands upwards, you gently caressed her milk engorged mounds. With the oil, it was like they melted to your touch. Every squeeze and rub earned you a breathy moan and a trickle of her milk. As kinky as you were, consideration for your boss stopped you from playing with her puffy nipples. You wanted to be sensual but not rough. Your efforts were rewarded with a slow kiss to your lips, making your dick tingle with excitement. As you stared down her belly, your mind hatched a devious plan and her being lost in pleasure offered you a window.

Gliding a hand downwards, you began rubbing her puffy vulva with the palm of your hands in a slow and fluid motion. Her breaths soon evolved into a cacophony of yelps, moans, screams, and utterances of your name. For too long, her condition and work schedule filled her with too much tension, begging to be released. A long loud scream echoed in the air as you inserted three fingers inside her moist sex. Using your thumb to give attention to her clit, it wasn’t long before your hand became drenched with an explosion of her essence. Harshwhinny bucked her hips as she rode out the entirety of her orgasm.

“Oh my, you still have your magic.” Harshwhinny moaned as she sat up. “This is bringing back… memories.”

“Memories?” you purred. “That was one hell of an experience and I never thought I’d be one for going to a massage parlor.”

“Well, I had to think of a way of making you mandated vacation start wonderfully.”

“Eh, it wasn’t too bad. A bit boring for sure but not terribly bad.”

“Honestly, I can’t tell if you’re an optimist. But I digress. There’s still the matter of your ‘reward’ for making me feel so good.”

“What reward?”

“Close your eyes, Calculus.”

Doing just that, you expected a nice blowjob from her. But oh no, you were given something far better. The moment you felt slick cold skin touch your shaft, you opened your eyes to see her belly firmly pressed against it. Up and down, it rubbed against your cock. Lord can only describe what you’re feeling in that moment. It was incredible, better than a blowjob. The way her body pressed against you nearly drove you to madness. Yet something other than lust drove her bellyjob. It was pure unchained intimacy.

“You like it, don’t you?” she purred “You like the thought of coating my belly with your big load? Go ahead, cum all over my belly when you want to.”

You desperately endured her motions, enjoying the rapturous feeling of the bellyjob. Bit by bit, you began to feel lightheaded, the signal of your impending orgasm. Once your grunts became more pronounced, Harshwhinny disengaged and started jerking you off. Just before you busted a nut, she aimed it towards her belly, coating it with your hot sticky jizz. Just the thought of cumming all over her figure turned you on immensely, making you shoot more of your load.

“My goodness. I thought you’d be spent after Redheart’s company. Then again, I know you’re not a one-pump chump.” She then crawled to your left and laid on her side, presenting herself to you. Then, she gave her ass a playful slap and a finger gesture that spelled come hither. “Now, you know what to do.”

Nodding, you scooched a bit forward and pulled her the rest of the way. Positioning your dick at her slit, you thrust your hips forward, penetrating her honeypot. You held her tightly as you began thrusting, all while giving her belly the occasional rub. Spooning had always been a favorite of yours ever since you banged Dean Cadence in high school. You always enjoyed the thought of holding a woman in your arms while you railed her from behind. It was the most comforting experience and it held a deeper meaning for you considering she carries your child. She wanted love and you were going to give it to her.

Turning her head around, Harshwhinny latched onto your lips once more in a battle of lips and tongues. She even placed her hands on top of yours as you rubbed away at her swollen abdomen. To think you’d be banging your boss a second time, luck has a way of sticking with you.

“Oh yes!” she moaned loudly. “Oh, I needed this so bad. Fuck me until I can’t feel anything! Fill my pussy with your cum!”

You didn’t need any permission to do so. You doubled your efforts and thrust like a mad man. Evey gyration tightened your balls further and further. Within the span of a few minutes, you shaft quivered and you blew your load in her snatch while still pumping in and out of her. Seconds later, Harshwhinny followed suit, drenching your crotch and the sheets below in ladycum. In the afterglow, a moment of silence was held between the two of you as your eyes made contact. By the time the ecstasy died down, the moon had started to rise and you were both tired.

“Calculus,” she yawned. “I don’t know about you, but I can just sleep in your arms right now.”

“If you want, I’ll be happy to accommodate that.” Reaching over, you pulled the blankets over your bodies, laying snuggly as you both started to feel heavy-eyed. As your senses started to relax and your eyes shut, Ms. Harshwhinny said something that made your heart stand still for a few seconds.

“I love you, Calculus.”

“I… I love you too, Julia.”


Author's Note

Well, the strict but closeted softie Ms. Harshwhinny makes her return. This time, she spills her heart out to her assistant. As always, I hope you all enjoy reading this.

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