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

by TheWingman

Candlelit Romance(Chrysalis)

Previous ChapterNext Chapter

“Fuck a duck!” You groaned. “Don't have the stuff for my cheat day meal!”

It was late October, well into your first semester of your second year in college. Despite being busy with your studies, you kept time aside to keep your body as fit as a fiddle. There are even days where you just want to let loose from your fitness crusade and indulge in the very things that aren't conducive to your regimen. One of these is enjoying the foods that you swore off for your diet.

One such food that you enjoyed was this asian noodle dish that Ignacio's girlfriend made for you two while hanging out last month. It had chow mein noodles with chicken, shrimp, peppers and onion with the whole thing flavored in savory teriyaki with hints of garlic. The first time tasting it felt like heaven made real. Being really polite about it, you asked her for the recipe for the dish which she gladly shared with you. Since today was the day you can try it for yourself, you were especially pissed that you forgot to get what you needed to make it happen. Fortunately for you, you had enough money to go get what you needed.

Taking about ten minutes by car to get to the store, the first thing you recognized was the produce aisle, rife with the fresh vegetables you needed. Grabbing some bags of peppers, onions, garlic and some chillies for an extra kick, you turned your attention to the exotic aisle where the last of the stuff you needed was there, the chow mein noodles and teriyaki. At that point, you could practically smell the dish cooking as if you were making it in that moment. Quickly grabbing the remaining items on your list, you turned back to your cart before you saw a familiar figure, one that you haven’t seen since high school.

“Chrysalis?”

How could you forget the name of Chrysalis? Back in your junior year of CPA, you took her sex-ed class. You recall the first day you took the class that you thought that the teacher would be old person. But to your surprise, Chrysalis stepped in and you almost felt your eyes jump out of your sockets at such a beautiful sight. Wearing a skirt with jeans, her hair long and flowing with the look silk and a nice keyhole sweater, it took all your strength to hide your boner during those classes. It was especially hard to do so when she was giving lessons on reproduction. You were always too nervous to ask a question in that class, let alone ask for help with the homework, she was just too damn sexy. Now, even as you caught a good glimpse of her, she still looked as sexy as she was back then that your ‘past experiences’ hadn’t prepared you for running into her for the first time since Crystal Prep.

“Holy hell, she still is smoking sexy like last time.” You thought to yourself as you pushed your cart to the checkout area. To your annoyance, the lines were rather long. You gotta blame the monthly sales for such an inconvenience. After a brief seven minutes, you got to check out and bag your groceries and leave. “Thank fuck that’s over.” You thought as you felt your stomach rumble with hunger. “Damn, gotta get home quick and cook this thing.”

Driving home, you decided to cut through the residential area where you encountered the least amount of traffic. It certainly felt relaxing to see the summer sun shine brightly through the trees as you move on through. As you approached an intersection, your eyes came across a familiar sight. It was Chrysalis and it looked like she was struggling to unload her van full of groceries. Wanting to use the situation to reconnect with an old teacher you secretly had the hots for, you parked on the boulevard near her house and climbed out, building up your courage.

“Ummm, Chrysalis, do you need some help?” She turns around with a confused look on her face, like she vaguely knows you but not all that well. As she completely turned around, you discovered to your shock that she appeared to be seven months pregnant. It paralyzed your legs in place to see that one of your crushes from high school was bearing a child.

“Yes I do, actually.” She said as she gripped more bags in hand. “But, how do you know my name though?” Taking a gulp of air, you prepared to bring an old memory to light.

“I’m Calculus, I was in your sex-ed class in Crystal Prep.” She crooked an eyebrow, still confused as to who you were. However, you stood out in that class as the nervous one that sat in the back, partially because of how beautiful she was. “I-I-I… *whew* was that nervous kid that sat in the back of class.” From that last statement, her eyes shot open as she remembered who you were.

“Oh yeah, I think I do remember you.” She said as she moved closer to you, putting the bags back in her van. Her bulbous belly was just short of touching yours. But then, she quickly pulled you into a hug, making your bellies touch each other. It felt awkward for sure, being hugged by a pregnant woman in broad daylight but the belly felt warm and oddly relaxing to the touch. “It’s really nice to see you after so long. How have you been?”

“Been doing good.” You replied, breaking from the hug. “Just making my way through the world.” You looked at the van’s trunk. It was full of bags of various stuff from the store, mainly food. You figured she had been there to take advantage of the deals after having been paid. “I actually saw you at the store earlier.”

“Did you now?” She replied “What were you doing there?”

“Just getting some ingredients for a cheat day meal. Been quite a fitness nut.”

“Oh yeah, I can certainly tell.” Chrysalis’s gaze turned back to her groceries with a look of worry and fatigue. “Hey, can you give me a hand with my stuff here?” Your heart beat at the speed of a rabbit. She was inviting you into her home. But then again, your intention was to help her out and allow her body some rest in her current condition. Without a second thought, you grabbed a load of bags and hauled them into her house. It looked cozy and nicely decorated with a fireplace as its centerpiece. She had some really good taste in decor. It took around twenty minutes to get everything put away, even your own stuff which she graciously allowed you to store for the time being. After everything was put away, you joined her on the couch where she was rubbing her belly.

“I was glad you helped me out back there.” Chrysalis said, rubbing her belly. “It wasn’t necessary but I appreciate the offer.”

“Well, I couldn’t have you overworking yourself when you’re this pregnant, Chrysalis.” You said as you found your gaze slowly drifting towards her protruding midsection. “I actually intended on stopping by and saying hello when I saw you at the store.” You grew more nervous as you continued to look on at her belly. The very sight of was oddly hypnotic to you and strangely enough, sexy. You’d never thought that after spending your time having sex with so many mature women that the thought of one being pregnant would make your dick tingle with excitement. However, you failed to notice Chrysalis staring at you with curiosity.

“Ummm, is there something the matter, Calculus?” Her question made you panic as you quickly looked away. You were embarrassed but you were also shocked as the fabled Dr. MILFlove has been left speechless by a pregnant woman. Unexpectedly, she put a hand on your shoulder and you jumped and shivered. “Calculus, are you okay?”

“S-Sorry, Chrysalis.” You stammered. “It was rude of me to stare.”

“You don’t have to be sorry.” She said. “I know my belly can draw a few glances here and there. I don’t mind if you do.”

“Ar-Are you sure?”

“Yeah, I can’t help it if the one growing inside me is making my belly big.”

“True. True.”

You were snapped from your conversation by a rumbling in your stomach followed by the most primal instinct known to man: hunger. Chrysalis was quick to take notice.

“Are you hungry there?” She asked

“Yeah, I was gonna make a noodle dish at my place.” You replied

“I’m going to make dinner here in a little bit. Care to join?”

“What are you making?”

“Hamburgers. Some delicious hamburgers.” You thought hard about what to do. On one hand, you wanted to have that noodle stir fry, on the other hand, you were just hungry and wanted something right away. Your primal desire for sustenance overruled your plans and made you impulsively accept.

“You know what, a hamburger does sound great. I haven’t had one in quite a while.” Your acceptance made Chrysalis smile with joy.

“Excellent. Why don’t you just kick back on the couch while I go make our dinner. Sound good?”

“Okay. Can’t wait to eat something, anything!”

“Oh, I think you’ll enjoy these hamburgers.” Chrysalis said as she retreated into her kitchen. Just as you heard what could be the pan sizzling, you began resting your head against the couch armrest.

As you drifted off to a short nap, you began having a dream of her… Chrysalis. The dream was about you and her, naked, on her bed, embracing each other while passionately making out. After breaking the kiss, you got behind her and locked her in a spoons position. You then began sliding your rock hard cock into her slit and began pumping and pumping into her moist wet sex as you caress her soft belly. Just as you were about to bust a nut in her, you were suddenly jolted awake by the soft slapping of your forehead. When you awoke, you were greeted by a protruding belly and a soft smile.

“Hey Calculus,” Chrysalis sang. “Dinner is ready!” Still choked up from the sight of her tummy inches from your face, you got up and nervously followed her to the dining room. What you saw plated on the table is what would make your mouth water like a waterfall. Two nicely grilled burgers, all topped with some sort of ketchup, some fried shellfish, a few slices of pickle and what looked to be hard boiled eggs on brioche buns, was staring you in the face. On her burger, the shellfish is notably absent, presumably because her condition forbade the consumption of such things, understandable. Part of you wanted to sit down and indulge right away. Being the gentleman you are with the pregnancy being hard on her body, you helped Chrysalis sit down before taking your seat. Both of your meals were served with some juice that smelled like apple and ginger, an amazing combo of flavors.

“So Ms. Chrysalis?” You broke the silence.

“Yes Calculus?” She replied as she took a bite out of her sandwich.

“I know it sounds awkward of me to ask but… who’s the father?” When you saw her cheerful face turn into a frustrated frown, it gave you a sense of guilt for bringing that subject up. It told you that how she got pregnant was something she wasn’t proud of. But, she did explain how it happened.

“I went to a party, made the mistake of getting drunk, one night stand and I later found myself growing a future child in me.” She growled. “Since that asshole doesn’t want to care for it, even though I considered the ‘other option’, I decided in the end to keep the child. I’ve always wanted kids anyway.”

“Yeouch.” You replied, feeling bad for her. “Are you fine rearing a child by yourself?”

“I’ll be alright in the financial side of things. My sister up north told me she’ll lend a hand.” You were amazed at how strong Chrysalis was in a situation like this, raising a child alone. From the time you first met her in school, she always postured herself as strong woman to match her beauty. Though you felt bad she’ll be single mother, her reassurances alleviated your worries. You always admired her for those properties, making her a tie between her and Cadence in terms of your crushes. “Go on, eat your dinner. You don’t want it getting cold now, don’t you?”

Taking the sandwich in your hands, you bit into it, making sure to get at least a bit of everything to get the full flavor. It tasted good, really good, like the most savory meal that’s odd looking but appetizing. Becoming enamored with the flavor, you took another big bite before taking a sip of the juice. It did taste like what it smelled like: apples and ginger.

“How’s the meal?” Chrysalis asked.

“I love it.” You said as you took another bite. “Where did you find out about it?”

“Found it from a video online, oddly enough. It just looked so appetizing.”

“That it is.” As you moved to take another bite, you felt your body getting hotter. At first you thought it was the AC but it felt cool when you walked in and it certainly felt like that outside. Then, your suspicions turned to the meal, wondering if there was something wrong with it. Seeing your slight discomfort, Chrysalis let out a chuckle.

“About the burger,” She started which alarmed you.

“What did you put in them?!” You blurted out in annoyance as the heat began to build up.

“All of the toppings on the burger are natural aphrodisiacs.” It shocked you for a moment but not for long. She was your sex-ed teacher after all and she knew all about how to sexually arouse people. “Oh and the drinks also has a bit of aphrodisiac as well.”

“So, you drugged me?”

“No, at least not with the burger.”

“Then why?”

“I’ve heard about your little sexcapades with some of the women around these parts. Cheerilee was all too happy to tell me.”

“Can’t say I’m surprised that word spreads around.”

“Well, since you’ve done a good job pleasuring a few of my friends, I wanted to treat you to something more… romantic.”

You saw her struggling to get up from her seat. With your gentlemanly instincts kicking in, you rushed to help her up. However, you accidentally found yourself holding her in a loving hug. You were both blushing with a shade of red so deep that it made it look like the color of Pinkie Pie’s hair. You found yourselves slowly leaning into each other as you puckered up for a kiss, only to be denied that pleasure by Chrysalis, holding a finger to your lips with a teasing smile.

“Not just yet.” She said as she left the hug. “I want to set up the scenery a bit.”

“What did you have in mind?” You asked.

“It’s a secret, Calculus. Why don’t you go into the guest room down the hall behind you and wait there. I’ll call you when I’m ready.”

Your excitement was an an all time high as you plopped down on the bed in the guest room. Imagination ran wild as you pondered what Chrysalis would do. The big thing on your mind was finally hooking up with the second of your two crushes from CPA. Desire went to new heights as you imagine groping her nice milk filled titties while passionately making sweet sweet love to her, much more different and much more passionate than the last six times you had sex. Just the thought alone was enough to make your dick erect.

“God damnit.” You mumbled to yourself as you began rubbing your bulge to satisfy that itch for the time being. You for sure knew how this was going to end but in what way was a mystery to you. Since she was your sex-ed teacher, Chrysalis possibly knew every trick in the book when it came to seduction and sex. Hell, you wouldn’t even be surprised if she had a copy of the Kama Sutra. You spent about twenty minutes rubbing your clothed member before a voice called out to you, a voice as smooth as silk.

“Calculus, I’m ready!”

There it was, Chrysalis’s call of seduction. Like you were rehearsing for a play, You walked out of the room to a sight that nearly stopped your already racing heart. There was no light in the living room, save for the lit up fireplace and a few scented candles on various perches. There were rose petals scattered around the floor, all, leading to a figure that was the subject of your earlier fantasy. There was Chrysalis, dressed in a green ball gown that had only a single strap on the back of her neck that kept the top in place. The dress had hugged offered enough support to her belly and breasts. In fact, It made them stand out and the breasts seem bigger than normal. You were left speechless at such a romantic setup.

“Hello there, Calculus.” Chrysalis said as you slowly entered the living room. She had her hair in a bun with enough length to dangle down her back. She then walks seductively towards you, making your spine tingle in anticipation. “I hope you like what I did here.”

“I-I-It looks… nice.” You stuttered to her amusement.

“Your tone gives me enough hint.” She pulls out a remote and presses a button. A few seconds later, some music plays through her room wide speaker system.

The music sounded like jazz, like the slow kind of jazz that romantic couples dance to. As the music entered your ears, her intentions became clear to you. Chrysalis, your old sex-ed teacher wanted to dance with you.

“Come on…” She said with an arm out, gesturing you to come forward. “I know you want to.”

Finally giving into your desires, you walk up to her and wrap one hand around her waist while taking the other one and holding one of hers up. She then rests her free hand on your shoulder as you pull her into you, beginning the dance in earnest. It felt good to finally be that close and that intimate with one of your crushes, despite her being pregnant. In fact, her belly touching yours felt nice, warm, exciting and soft to the touch. You two swayed from side to side as you and Chrysalis danced to the tune of the song. Slow yet sensual, the romance was certainly in the air.

As the song was nearly over, Chrysalis wore the fabled bedroom eyes and leaned in slowly towards your face. Knowing her intent and with your blood still boiling from the aphrodisiacs, you closed the gap between you two and locked your lips with hers, sharing the most intimate kiss you’ve ever had and pulling your bodies close. But, the kiss felt different than last several times you did with any women. It had a feeling that wasn’t of just pure lust; It was of love, pure love, the kind of love one would feel for their significant other. For the first time as Dr. MILFlove, you had found a MILF you can call your ‘favorite’. The kiss lasted until the song ended to which Chrysalis broke it and switched off the music player.

“Wow,” You gasped, still reeling from the romantic experience. “I’ve never felt my heart beat like that apart from working out.”

“That’s called love, Calculus.” She said as she placed a hand over your heart. You blushed harder than before as your heart rate grew faster. “I can tell by your heart that you want me… and you like this.” Taking your hand, she walked you to the couch, directly in front of the fireplace. As you sat down, the both of you looked on at the dancing flames, going in all sorts of weird directions in a mesmerizing dance. Chrysalis then leaned into you as she wrapped her arms around you and rested her head on your shoulders.

“You’ve really went the distance for this, Chrysalis.” You said as you rested an arm on her left shoulder. “I’ve never experienced romance like this before.”

“Well, you’re in for a treat *chuckles*, Dr. MILFlove.”

“I like it when you call me by my nickname, Chrysi.”

“Chrysi, that sounded cute.”

“It’s meant to be.” Upon hearing that, Chrysalis unhooked one of her arms from around you and grabbed your free hand, placing it upon her large belly. It felt strange at first but you warmed up to it, feeling the warmth and life that she grows within her. It was pure intimacy as you sighed and hummed while brushing your hand across the surface of her tummy. However, you wanted to change things up as you knelt down and placed your lips on the belly, giving it a long and loving kiss. Chrysalis seemed to enjoy it, even laughing a few times as you gave it a few light pecks which tickled her. But then, you craved more. You wanted to go all the way with her.

Slowly climbing back on the couch, you hovered over her as you held her in an embrace like the one from the dance and slowly touched her lips with yours. You moved your hands around her body and began to dry hump her as she moaned in your kiss. She enjoyed it, you enjoyed the she fact she does as you began to ramp up the passion. However, you surprised as she pushed you to your back as she climbed over you with a look of hunger in her eyes.

“You know, Dr. MILFlove…” She purred. “With my pregnancy, my hormones are on the fritz and that makes me exceptionally…” She then nibbles your ear for a bit but enough to make you shiver exponentially shiver. “Horny.”

“What do you have in mind then?” You asked to her delight as she climbed off the couch and turned her back toward you. She then fiddled with the dress strap on her back until you heard an audible click. Letting go of it, she lets the fabric fall to the ground which presented you with a sight that made your dick become rock hard with excitement. She was wearing nothing at all, no bra, no panties, not a damn thing. There she was, your old sex-ed teacher, naked and pregnant in front of you. You knew you were going to be in for a good night.

“Your shirt, get rid of it.” Doing as she ordered, you removed your shirt, exposing your toned chest for her to see. She was giving you that hungered look as she started to lick the surface of your chest until she reached the hem of your jeans. She proceeded to unbuckle your belt and unbutton your pants, dragging it and your underwear down, exposing your already hard member for her to see. Judging by the way she looked at it, Chrysalis hungered for your cock and she was going to get it.

She sandwiched your shaft between her milk-swelling breasts and began rocking them up and down your length. Compared to the other titjobs you’ve had before, this was the best you’ve had so far. The feeling of your cock being massaged by her warm milk filled breasts felt like… well, you couldn’t really describe it at all. It felt that good. What she did next is what would be a test of your endurance. She gave a light peck on the tip of your spear, giving it a good few licks before taking it into her mouth. Your stamina was being tested as the combined warmth of her wet mouth and the softness of her mounds began to eat away at your endurance, your willpower not to cum. You badly wanted to explode your load into her mouth but you wanted to enjoy it for as long as you can last and to make her happy. Eventually, your willpower ran out as you couldn’t hold it in any longer but you were able to pull out in time and aimed your cock at her belly. With one good stroke, you shot your semen onto her belly, decorating her rotund tummy with your sticky seed.

After your orgasm subsided, Chrysalis left your side as she began lining up various pillows in front of the chair near the fireplace. Your heart raced in anticipation of being able to mount Chrysalis and fucking her. Chrysalis however, had other plans in store for you.

“Come,” Chrysalis said, patting a hand on the pile of pillows. “Lay back on this.”

“Wouldn’t this be the part where I take the lead?” You sarcastically quip.

“Calculus, You’ve spent so long taking the lead that I think you deserve a rest. Now, come here and lay down. I’ll take the lead.” Heeding her words, you walk over and laid upon the bedding of pillows. Not long after, Chrysalis mounted you, rubbing her dripping wet slit against the tip of your spear, sending shivers throughout all your nerves. She then took your cock and lined it up with her vulva, spearing herself on your length. It felt incredible, a whole new feeling, being inside your crush while she’s pregnant, exotic and erotic.

She then takes your hands in hers as she begins riding your cock. Gradually increasing her pace as she rode your length, Chrysalis leaned closer to you, allowing her belly to rub against yours as she pressed her lips against yours. Abandoning the hand holding, you wrapped your arms around her back as she began riding you harder.

“OH YEEEEESSSSS, DR. MILFLOVE!” Chrysalis loudly moaned as her hips continued to pounce on your dick. “YOU CAN’T IMAGINE HOW LONG I’VE WANTED TO BE FUCKED SINCE THAT DAY!”

“I can certainly tell!” You grunted as you kissed her back. You groaned and moaned as she began going faster than ever, pushing you and her to the edge. Her inner walls began to tighten around your pole as they eagerly desired to milk you for every drop of your cum. Soon, you were at your peak and couldn’t take it anymore.

“Chrysalis, I’m… gonna cum!” You groaned as you held her tight, feeling your orgasm draw closer.

“Go ahead!” Chrysalis breathed. “Fill me up to the brim!” After that, you couldn’t hold it in any longer and busted your life giving seed into her warm vagina. Every pump of your cum sent you and Chrysalis deeper into orgasmic bliss. You held each other tight as you kissed in front of the fireplace. As your orgasm drew to a close, you expected to be tired out of your wits. But oh no, you still had the energy to go a couple another round, same for her.

“Goodness!” Chrysalis sighed in slight exhaustion. “You’re still hard! Care to go for one last round?”

“Yeah,” You panted. “I’m not tapped out yet!”

You sat up as Chrysalis speared herself on your still erect shaft with her back facing you. It was perfect; She sat against you in a position that allows for easy access to fondle her belly and succulent boobs. You groped and grabbed at her breasts and midsection as she rode on you, reverse-cowgirl style. Without any thinking, you kissed up her neck before your lips made contact with hers once more. Both of you were lost in passionate love as you saw an opportunity to take control. You held her tight and laid down on the pillows, going from reverse cowgirl to spoons.

“Spoons?” Chrysalis asked with amusement. “You want to do spoons?”

“Yeah, I thought it would be romantic that way.” You replied.

“Well, don’t stop thrusting, Dr. MILFlove.” With the utterance of your pseudonym, your lust went into overdrive as you lifted one of her legs up and resumed your thrusting. Still buzzed from the aphrodisiacs from your dinner, you still had some energy to spend and spend it on one last fuck you will. Thrusting and pumping your cock in and out of her wet and hungry sex, you grunted with passion and lust as you enjoyed another round of humping another long time crush. You enjoyed every second of being in that position with Chrysalis, a romantic way to top off an evening like this.

Eventually, like the sweetest of candies, all good things must come to an end as your energy burned out, causing you to shoot the last of your load into her hungry pussy. You growled in sheer orgasmic pleasure as you busted your nuts in Chrysalis for the third and final time tonight. You felt like you were in heaven. With your orgasm dying down, you cuddled behind Chrysalis, hugging her from behind as you felt her heartbeat with your hand.

“I hope you liked our little… dance, Calculus.” Chrysalis moaned as she placed her hands on yours. “I know you like to feel my heartbeat. It beats for you.”

“So does mine,” You say as you peck her on the lips. “For you that is.” It’s true, you feel feelings for Chrysalis. However, your identity as Dr. MILFlove would seem to put your heart’s desires into uncertain waters. But then again, you do enjoy the idea of a ‘personal favorite’, a notion you have to keep secret.

“You’d better watch out for my friends, stud.” Chrysalis whispered. “They can be quite the opportunists.”

With her words, you could tell she gave you her blessing to continue with your ‘line of work’. Every MILF in town still wanted a piece of you and you can’t fathom how they’ll react when you chose to settle down with one lucky woman. But then again, you found yourself better at keeping secrets as nervous at times as you can be. Taking a moment to give some thought, you noticed the candles have burned out, saving you the trouble of having to put them out. The fireplace was starting to get that way as well. Leaving Chrysalis’s side for a moment, you fetched a blanket from the nearby couch and draped it over your bodies, rejoining Chrysalis in post coital cuddling.

“Chrysalis,” You started. “Though Dr. MILFlove doesn’t limit him to just one lady,” You gently placed your hand on her belly and held her close once more. “He does have room for a ‘preferred client’.”

“You cheeky stud.” She moaned as she began to fall asleep in your arms. “I might have to take up on that offer in the future.” With her finally asleep, you feel the pull of slumber bearing down on your mind. As your eyes begin to shut close, you rubbed your cheek against hers as you let out one last yawn before you go down for the night, content and satisfied.

“Well, there’s a first. Dr. MILFlove found himself a ‘special ladyfriend’. She’s something special alright. Gotta play this cool though.”


Author's Note

Sorry this took a while to write. I wanted to make this chapter a little longer because I felt that it would be better that way. Also, sorry if the whole pregnancy fetish of this chapter possibly might not be your cup of tea. I came up with it to try something new as per the story description of including some kinks that aren't too gross. Truth be told, I originally planned on releasing this for valentine's day instead of Windy Whistle's chapter. Anyways, I hope you continue to enjoy this story so far. Your feedback is what matters the most.

Next Chapter