Well, you’ve done it. You’ve conquered your first year of your two-year business and accounting program in college. With summer break having arrived at long last, you had more time for recreational activities that you so enjoy. One such passtime you like is running and jogging. Though it annoyed you that your parents forced you to be on the swim team, it did instill an obsession for physical fitness for you. In your line of work or the one you’ll be going into, it pays to have a healthy body for a fully functional mind. Even though you were no longer on the swim team, you replaced it with running. One of your favorite places to run at was the track at Canterlot High, which was closed for the summer.

“Come on, where are they?” you muttered to yourself as you looked down at your phone’s clock. “Rainbow dash said they’d be here by now.”

Rainbow Dash, oh how could you forget that name. Despite being from opposing schools, that didn’t stop you from hanging out outside of the education system. You first met her while she and her boyfriend Soarin were working out at Planet Fitness. While they were at the bench press station with Soarin spotting her reps, you walked over to them and stuck up a friendly conversation. Eventually, the conversation sparked a friendship between the three of you as Rainbow got done with her exercise. As you began your turn on the station, they were still there and wanted to what you were made of. You managed to bench 40 reps at 200lbs which made your arms feel like jello. From there on, You, Rainbow and Soarin became workout buddies. Though she and Soarin were dating, it didn’t make the friendship between you and Rainbow awkward, considering that you banged Principal Cinch a couple days before meeting her. Then again, you didn’t care about their romance from the get go.

Despite being done with high school, the three of you have this monthly tradition where you all would spend an afternoon running a track, depending on the weather. It was a nice way to stay connected, to do the things you all enjoy. As you were reminiscing on your earlier years, your phone received a text message from Rainbow Dash:

“Soarin won’t be with us today. He has an out-of-state family emergency. Will be there in two minutes.”

Well, the monthly workout will still go on but without the other member of your workout. Normally, the workout would’ve been rescheduled if such a situation came up but for Rainbow Dash to do it anyway sounded odd for sure. You wondered if she was bringing her equally athletic friend Applejack to stand in for Soarin. However, your thoughts were brought to an end when you saw Rainbow’s blue camaro pull up in the parking lot. You then decided to do some last minute leg stretches to stave off any leg cramps before the group workout.

“Heya Calc, sorry we’re late!” Hearing RD’s signature energetically impulsive voice, you turned around to see Rainbow Dash along with an older woman with her. She looked a lot like Rainbow Dash but just slightly taller, older looking and with a different hair color and style than her. At first your instinct thought her to be a sister she didn’t tell you about but you knew she was an only child. The woman runs up to you with the intent of giving a handshake.

“Oh hiiiiiii, you must be Calculus!” She says as she shook your hand. “I’m Windy Whistles, Rainbow Dash’s mom. It’s a pleasure to meet you!”

How you would describe Windy Whistles is this: Rainbow Dash might as well have been a near-perfect clone of her. They both look nearly alike with the spunky can-do attitude to match. However, for a woman her age, she looks relatively young to the effect of looking just slightly older than her daughter. From what you can tell from her breast size, she was a C-Cup, not too big but not too small, decent. She had a nice slender body from working out to the same degree as her daughter and her shorts made her nicely firm and muscular ass stand out, a nice size that would make you happily hotdog those nice buttcheeks.

“Nice to meet you too!” You replied. “What made you wanna workout with us?”

“My little Dash was somewhat annoyed that her boyfriend had to go out of state for an emergency. Being athletic as her in my haydays, I offered to tag along with her. Though she was reluctant at first, she eventually warmed up to the idea.”

“Yeah,” Rainbow Dash scoffed. “I know it feels weird working out with my mother here but I really didn’t want to miss leg day with Soarin MIA.”

“Well, a mother and daughter workout day it is then...” You scoffed as you joined them on the track between them, getting into a starting position. “Plus a friend. Though I’m not on CPA’s swim team, I still treat my fitness like a hobby.”

“Heh, for an egghead like yourself, you sure do work on a body to match.” Rainbow Dash chuckled at your statement.

“Yes,” Windy Whistles agreed “such a combination would make ladies everywhere swarm all over you, Calculus.” Her statement made Rainbow groan in embarrassment.

“MOM!” She shouted. “He’s right next to you!”

“Eh, I really don’t care, Dash.” You shot back with a laugh. “I know I’m somewhat attractive. I can’t help it.”

“Don’t let that get to your head, amigo.”

“I try not to.”

“Well kiddos, are you ready?” Windy Whistles chimed in. You and Dash both look at her and shook your heads in agreement.

With a count of three, the three of you began the sprint, working your legs as fast as they and your respective staminas can take. You were a little faster than Rainbow as you were able to keep a noticeable distance ahead of her with her mother taking the lead but out of your sight. As you were keeping your sprint in perfect tempo, you felt a something smack onto your right buttcheek.

“You gotta keep up, young man!” Windy Whistles sang as she ran ahead of you. It felt weird, not just that she did it, but because she had the audacity to do so in broad daylight in full view of her daughter. You anticipated it was gonna feel awkward when the workout was finished but you didn’t know for sure. All in all, you just wanted to focus on your workout and not skip a beat. For the next three hours, You, Rainbow Dash, and her mother continued the footrace before the setting sun told you that it’s time to stop.

“Holy shit!” You panted as you leaned down, palming your knees. “I’ll hardly get used to the feeling of my lungs burning.”

“Ah, tough it up, big boy.” Windy Whistles wheezed as she patted you on the back. “You’ll get used to it in no time.”

“Yeah,” You shot back “not when I keep upping the intensity. You gave me a run for my money, Ms. Whistles.”

“Heh, It’s funny when you got outclassed by my mother.” Rainbow Dash snarked to your annoyance.

“Yeah Dash, pull the other one.”

After the both of you caught your respective breaths, you all felt relaxed enough to move again with sweat drenching your clothes and bodies.

“Hey Calculus,” Windy Whistles called to you. “How did you get here?”

“I walked here actually.” You replied.

“You must be tired after all the jogging. How about you shower at my house and I’ll take you back to your place afterwards.” You were slightly stunned at Windy Whistles offer, more so in front of her own daughter. Even then, you were much too weak to walk back to your place to really care about that fact. Being grateful towards her offer, you accept it.

“Yeah, that sounds good.” You agreed to her delight.
“Excellent, come, let’s get outta here.” She replied as you and Dash walked with her to her car. As she climbed in, Rainbow Dash pulled you aside.

“Hey Calc, you might wanna be careful around my mom.”

“Why’s that?”

“For starters, I saw how she was checking you out before we got started. Plus, I did see her slap you on the ass.”

“Uhhh, why should this worry me?”

“Because Calc, she’s, how should I put this… frisky. She’s very horny and frequency that she and my father have sex is one of the reasons I moved out. Ugh, the moaning and squeaking of the bed drove me nuts.” You feigned concern at her cautioning but you were no stranger to what she warned about. After all, you’re making yourself known amongst the town’s local MILFs and have no aversion to some ‘fun time’ with them.

“Don’t worry, I’ll be cautious around her.” You assured Dash to her slight relief.

“Okay then.” She said as she walked over to her car with you following her.

For the ten minutes on the road, the car pulled up to Windy’s house. It looked somewhat big but not as you imagined. Climbing out of the car with your duffel bags in hand, You and Windy Whistles walked into her house, still exhausted from the workout. Her living room was decorated with pictures of her daughter, some of them with herself and what looked to be her husband. You couldn’t help but let an amused huff that Rainbow Dash has such supportive parents that hold her in such high regard.

“Calculus, the bathroom is upstairs.” Windy Whistles said as she walked over to said stairs. “Here, I’ll show you where it is.” Following her up the stairs, you arrived at the bathroom at the end of the hall. It had all the usual stuff such a room would always have with the shower and the bath being an all-in-one deal. You walked in, expecting to have the first shot at cleaning up. To your surprise, you heard the door lock latch in place with Windy Whistles standing behind you with an all too familiar look. You were prepared for such an occasion but your stamina was starting to tell you otherwise.

“Mrs. Whistles,” You gasped. “I thought you let me go first.” Windy, however, walked in front of you and began taking off her shirt, revealing… absolutely nothing. There was nothing hiding her bare breasts from your sight, those soft and perky mounds that you like to squish in your hands. You blushed as she took off her shorts along with her panties, revealing a hairless flower that’s either dripping with sweat or from arousal, you couldn’t tell. She then climbed into the shower and turned on the hot water, hosing her entire body.

“What are you still doing standing there?” She asked as you looked her in the eye. “Come on, strip and join me.” Being the horndog you are, you oblige her and stripped off all your clothes and climbed in. Upon entry, you were hit by streams of soothing hot water, relaxing your aching leg muscles. As you stared at the naked form of Rainbow Dash’s mom, she turned around with a confused look on her face. “What’s the matter, Calc?”

“Uhhh, nothing.” You replied, gathering your thoughts. “It just… feels kinda weird being in a shower with my workout friend.” You could tell by the change in her facial expression that she didn’t buy what you said.

“Is that all?” Windy said as she walks over to you with water flowing down her slender figure. “Well, Mrs Cake told me about how you pleasured her like a beast. I know my body is awesome, judging by how you’ve been looking at it.”

“Heh, I guess word did spread more quickly than I realized.”

“Indeed.” She replied, snaking a finger seductively down your chest. “I used this as an opportunity to try you out for myself. However, since you did a good job during your workout, I’ll let you wash me first, front and back.” You were left slightly speechless at her offer. Windy Whistles, Rainbow Dash’s smoking hot mom, wants you to wash her first. You knew from the first time you saw her that you wanted to caress every inch of her hot body. Giving into your carnal desires, you take some body wash and globbed it in your hands and began lathering her arms with the soap.

“Mmmmmm,” She moaned as you went from her shoulders to her arms. “You have quite an amazing touch.” With every massage of her arms, Windy backed further into you until your now rock hard member made contact with her firm ass. It felt good to feel such a thing from an older yet athletic and youthful woman grind against your cock. “Please Dr. MILFlove, feel free to feel the rest of my body.”

With the mentioning of your alter ego, you needed no further persuasion as you moved your soapy hands from her arms to her tits, washing them with the palms of your hands. With every lathering, you felt the bump of her erect nipples against your hands. For some reason, you subconsciously began bumping your crotch against her firm rear end. Your member wanted it and it wanted it badly. However, you wanted her to invite you in for it, considering she brought you here to wash up instead of having to walk home for that.

With the moaning from her tit massage beginning to die down, you had to think of something more erotic and sensual. Keeping your left hand on her right tit, you slowly moved your right hand down her chest and stomach, sensually feeling the subtle hints of her pores on her silky smooth skin. Her breathing and moaning intensified as she felt the soapy and warm wetness of your palm glide across her flat toned tummy. Finally, your hand reached the beginning of her crotch. You balled up your hand with the exception of your index and middle fingers and massaged her crotch with them. Form the increased tempo of her breathing, you could tell she was enjoying this alot.

“D-D-Dr. MILFlove,” Windy Whistles panted in pleasure. “Go ahead, stick that cock between my asscheeks and hotdog me!”

There it happened, the invitation you’ve been longing for ever since you laid eyes on her. Your inner beast compelled you to stick your throbbing erection between her ass and grind like a madman. Briefly adjusting yourself but not taking your hands off of her, you nestled your rod between her firm yet cushiony buns, pulling her closer to as you grind against her ass. She knew that her ass would please you this way and you were doing good pleasing her as well. To you, this type of skin to skin contact was so good and intimate that it felt better than a blowjob. You loved every second of it as you and her moaned into the night without any care in the world. Moving your hand over her vulva, you took it in your hand, palming and massaging it as her screams heightened in volume.

Because you were palming her, you frequently brushed against her sensitive clit as you squeezed and kneaded her wet pussy walls. Soon, you felt the familiar pressure in your balls build up to its peak. You want to cum at the same time as she does to add to the collective pleasure between the two of you. Stopping your palming for a short moment, you took three of your fingers and slid them into her hungry wet sex. She was both surprised and enraptured at your change of tactics that you could’ve swore you saw her eyes roll to the back of her head in pure bliss. Eventually, neither of you could take it anymore as she squirts her juices all over your hand with you emptying your balls all over her back. Ropes upon ropes of your cum splattered onto her back as you held her tighter against you, wanting to hug her tight as you became entranced in orgasmic bliss. As your orgasms subsided, Windy Whistles collapsed onto the bathtub floor wit you following shortly after.

“Wow,” Windy Whistles wheezed, still reeling from her orgasm and wrapping her arms around your neck. “I’m impressed that you have such amazing stamina. You even make me break a sweat.

“The pleasure is all mine.” You said as you prodded her vagina with your still rock hard cock.

“My goodness!” She gasped in amazement. “You’re still hard?!” Looking her square in the eyes, you brought your face closer to her.

“Because… we’ve yet to do the main event.” You said as you touched your her lips with hers, partaking in a passionate kiss. As your tongues wrestled for dominance, Windy’s tongue fought with incredible ferocity. You eventually broke the kiss to breathe some air, knowing that it was time to do.

“Do it,” Windy Whistles begged. “Shove that big cock of yours into my pussy and ravage me like all the others!” The begging sounded hot and sexy. She really wanted to feel your cock inside her. You rolled your hips forward and slowly slid your member into her love tunnel until you were hilted. It felt incredible to be so deep inside Rainbow Dash’s mom that you couldn’t describe what it felt like. Exchanging smiles, the both of you resumed your passionate kissing as you thrust your hips forward, sliding in and out of her vagina. You kissed and fucked Windy Whistles with all your might as the still running shower continued to spray soothing hot water upon your bodies which made rubbing your bodies together all the more easier and pleasurable. In the spur of the moment, you sat yourself and her up and placed your hands on her ass and upper back, pulling the two of you closer as you continued to pump her pussy like you were starved of sex.

You began to feel the impulse of your orgasm on the horizon and you could tell she was there too, judging by how tightly her inner walls gripped around your shaft. You began to pull out, not wanting to risk getting her pregnant. To your shock, she wrapped her legs around your waist. Though she didn’t say anything else, you knew what she meant, what she wanted. As you picked up the tempo of your thrusts, a thought began to course through your mind.

“Holy hell, I can’t believe I’m about to cum inside Rainbow Dash’s mom! I can’t believe it’s happening. Though part of me wants to bail, I’m assuming she’s on birth control. You know what, fuck it. I WANT TO CUM INSIDE RAINBOW DASH’S MOM!!!”

And cum you did. You practically felt the contents of your balls explode inside her womb. The feeling of your hot seed exploding in her insides was enough to push her over the edge and make her orgasm all over your crotch. You held her in a deep hug for a few good minutes before you both collapsed back onto the floor. Breathing and panting and still reeling from your orgasms, you and Windy Whistles engaged in some post coital snuggling with some kissing to top it.

“Wow,” You said, looking at a tired Windy Whistles. “You felt extremely good.”

“I… know!” Windy Whistles breathed. “I’m just one awesome woman! How did you have that much energy after the workout?”

“Just had some leftover drive I guess.”

“Hmmm, It’s amazing that you have so much endurance. It reminds me of how me and my husband do it, but compared to how we just did it, you were slow yet passionate. I love it.”

“I’m glad you do. Speaking of which, where’s your husband?”

“Oh, he’s out with his brother, throwing a wild bachelor party before he gets married. He won’t be home until tomorrow night.”

“Well now, congratulations to his brother.” As you looked around the bathroom, you noticed the clock read 10:07 PM. You were amazed that you and Windy Whistles have been fucking for a little more than three hours. You wanted to pack up, get dressed, and go home but spending all of your energy made that impossible to do so. You let out a yawn as you snuggled back into her arms.

“Hey Calculus, do you want to sleep with me for the night?”

“Well... sure, why not? You agreed without an extra thought. After the both of you climbed out of the shower and dried off, You and Windy Whistles, still completely naked, walked into her bedroom. She climbs onto the bed with you climbing on top of her, looking at her with your own brand of bedroom eyes. You wrapped each other in warming embrace as you pulled the covers over your bodies. Giving her one last kiss, you rested your head on her chest and began to fall asleep. The last thing you remember hearing before you drifted to sleep was:

“I love you… Dr. MILFlove.”

“Heh. Dr. MILFlove, even to this day, you still got game.

Author's Note

Whew, managed to get this one written just in time for Valentines Day(took me 2 days to write it). Well, since one person in the comments wanted to see Windy Whistles as a subject of a chapter, I couldn't help but want to do it. Truth be told, this chapter in particular was inspired by Hit The Showers by Harm's Way, one of my favorite clopfics. So, this is the surprise chapter I was working on in parallel to Chrysalis's Chapter.

Anyways, I hope you enjoy this chapter and the story so far. Happy Late Valentines Day.

P.S.: When I had the O.C. say

"I WANT TO CUM INSIDE RAINBOW DASH'S MOM!!!"

, I actually had planned on that reference to that phrase pertaining to her daughter, seeing as how Windy Whistles is involved.