To Cheer A Teacher

by StuffMyCrust

Rating: mature
Tags: Cheerilee, Slice of Life, My Little Pony: Friendship is Magic, Human, Romance, Anon, Sex
Length: 5801

Anon wants to surprise Cheerilee with a few gifts after a long work day for her. As the day goes on, interesting events happen that not even Anon was expecting.

Being a teacher can sometimes just suck. Anon is totally aware of this and being friends with Cheerilee, it only proves his hypothesis. One day he decides to surprise her with some cupcakes and flowers to show that there are people/ponies that appreciate what she does. He hopes it will make her rough day better. After he meets with Cheerilee, a lot of interesting things happen that not even Anon was expecting.

This is rated Mature for sex and use of language during the sex acts.

Contains: Human X Pony towards the end of the story.

Published 2019-05-01 23:30:01 UTC
Last updated 2019-07-11 07:24:08 UTC

Ch 1: Errands

It’s a beautiful Monday. Everyone is out and about for their typical day. The kids are in school for another long five days. Life is great, especially for those that are teachers.

A positive-minded pony named Cheerilee is a well-known figure within the small town of Ponyville. She’s a teacher at the local school where she teaches young ponies a variety of subjects. Everyone loves her and her optimistic personality. She’s touched the lives of many ponies alike, but never had she thought of impacting the life of a lone human in Equestria.

Cheerilee had one day encountered this human at the food market. She had heard of him before, but had never actually seen him in person. His name was Anon, he was the only human residing in Equestria. As the two were looking at fruit, they both bumped into each other sparking up a conversation which eventually grew into a good friendship.

It’s been about a year since that day and now both Cheerilee and Anon are great friends. Some ponies even started to picture them being a couple. Much to Anon’s dismay however, Cheerilee would quickly brush off those rumors if brought up. Overtime Anon had started developing feelings for her. What Cheerilee had that other ponies didn’t was the fact that she happily accepted Anon as a friend for who he is. Many other ponies were intimidated by the bipedal figure and were typically hesitant to interact with him.

Cheerilee was obviously unaware of Anon’s feelings, but he didn’t mind for now. He was planning on waiting until Hearts & Hooves Day to give it a shot, but that was another two months away, he had plenty of time.

With it being a Monday, Anon knew Cheerilee would be busy educating the young ponies. He didn’t even realize she was a teacher until about 2 months after he met her. He respected her for being able to put up with children. Even though Cheerilee always claims she loves teaching, Anon knew her well enough to see that some days she doesn’t even want to bother with teaching.

Typically once Cheerilee would finish up for the day, her and Anon would get together and do a variety of activities. However today Anon was gonna surprise her by showing up to the school itself.

It was only 1:00pm according to the position of the sun, Anon decided it would be nice to gift her something. He thought flowers would suffice and maybe a few cupcakes. She could have a rough day for all he knew, so an act of kindness would hopefully turn it around just in case.

Anon made his first stop at Sugarcube Corner to grab some cupcakes. Typically a frantic pink pony would be there ready to tackle him down and start rambling nonsense at the speed of those narrators at the end of commercials, but this time was not the case. Instead he came across one of the actual owners of the joint, Mrs. Cake. In his view, she was a smoking hot MILF. Since she was married however, he accepted he wouldn’t get a shot with her.

“Oh uhhh hello Mr. Anonymous! How may I help you today”?

“Please, just call me Anon. I’m here for a few treats...it's for a friend of mine. I’ll take two chocolate cupcakes if that’s alright” Anon said shuffling his hand through his pocket.

“Two chocolate cupcakes you say? Alrighty dear, coming right up”.

As she went into the back to gather the materials, Anon sat himself down at a table nearby and waited patiently. Within a minute or two, Mrs. Cake had presented herself once more with the treats Anon had requested.

“Okay, that will be 4 bits Anon”.

“Only 4 bits?” the human asked raising his eyebrows.

“I’m giving you a discount for being a regular customer and always trusting us for your bakery needs. Think of it as a gift,” Mrs. Cake said giggling.

“Oh uhh, thank you Mrs. Cake, that means a lot”.

“It’s my pleasure, dear. Now you go have fun with your friend,” she said with a smirk on her face.

“Will do”.

With that, Anon departed Sugarcube Corner. He can finally say that he managed to visit Sugarcube Corner without being pounced by Pinkie Pie. He honestly wondered where she was at that point but quickly brushed the thought off. His next stop was to visit Roseluck and buy some flowers.

As Anon made his way to the marketplace in town, he saw out of the corner of his eye a familiar pink figure. He immediately knew exactly what it was, and it was coming straight for him.

“No..NO...NONO..NOOOOO PLEASE NOO!” he screamed internally as the pink pony sprinted towards him. He braced for impact.

“NONNYYYYYYYYY!!!!!” was all Anon heard before he was practically body slammed by Pinkie. As much as he loved the pink pony, he never really enjoyed how hyperactive she was to him for the most part. Nonetheless they were still friends.

“Nonny hey! Whatchu doing with those very scrumptious looking cupcakes” she said clearly hoping she can snag a piece.

“Okay first, can you get off me? I can hardly breathe”!

“Whoops, sorry!” she said giggling.

“First off, these cupcakes are a gift for a friend. An act of kindness. To answer the other question you probably have in your head, no these cakes aren’t for you unfortunately, sorry”.

“Awwwww okie dokie lokie. Who’s it for then”?

“If you happen to know who Cheerilee is, it’s for her. I figured she might be having a rough day with all the kids so I thought ‘why not?’”.

“Ooooooooooo okay! Well….I’ll let you get to that because I just remembered I gotta hurry up to Twilight’s castle for a little meeting. Talk to ya later Nonny!” she said as she suddenly dashed off like a bullet.

“Well that went better than expected,” Anon said to himself.

Continuing through the marketplace, he set his eyes on his target. He spotted the flower shop where Roseluck works. Roseluck to Anon was a very sweet pony. He always came to her for all the flowers he needed. Roseluck never disappointed him with the stuff she had.

Upon entering the shop, he looked around for Roseluck and noticed she was busy watering some plants. He decided to ring the little bell near the door to get her attention.

“Oh? A customer? Just a second I’ll be right there!” she said as she stopped watering and went to put the watering pot in her tool room. Once she finished, she made her way to her guest.

“Oh hi Anon! What brings you here”?

“I’m here to grab a flower bouquet. What do you have in stock today”?

“Oh I got a variety of things. I got a few roses, some bluebonnets, daisies, lavenders and plenty more. See anything you like”?

“Hmmmm, I’m interested in these lavenders right here. How much are you wanting?” Anon asked as he smelled the flowers.

“I’ll offer 8 bits for this pair right here. Sound good for you”?

“Yeah, that works just fine. Here you go,” Anon said dropping the 8 bits on the counter.

“Alright thanks Anon. Might I ask what you’re using them for”?

“Hmmmmm? Oh they’re a gift for my friend. You know who Cheerilee is right? It’s gonna be for her”.

“Awww that’s sweet of you. I think she’ll love those flowers, she always loves the flowers I have in stock. Hey be sure to tell her I said hi okay”?

“Haha, alright I’ll be sure to do that,” Anon said looking outside and studying the position of the sun to get the time. He noted it was 2:00pm at least, so he had to get going. Class would wrap up at 2:30pm.

“Anyways, I gotta get going. Thanks a lot Roseluck, I’ll see you later”!

“No problem, you take care”!

With the presents acquired for the receiver, Anon started making his way to the local school Cheerilee worked at. He would probably get there in about 15 or 20 minutes depending on his walking pace. Knowing class wouldn’t be over by the time he got there, he wondered how he was gonna surprise Cheerilee without one of the little ponies possibly giving him away. He then decided hiding in a bush would suffice.

“Oh Cheerilee won’t be expecting this!” Anon said with a chuckle.

Author's Note

I've scrapped probably almost 15 ideas for this story and finally settled on something like this. I will gladly accept any criticism for this story.

Anyways, next chapter is when Cheerilee officially comes into play.

Ch 2: One Thing Leads to Another

As if it were on cue, Anon heard the school bell start ringing signifying the end of classes. Not even a few seconds later, the little fillies and colts started bolting out of the building. Anon decided to wait a few minutes in case one pony or two stayed behind to ask Cheerilee a few questions.

Analyzing the many small ponies as they trotted further away from the school, they seemed to be a little hyperactive this time around. He hoped they didn’t cause Cheerilee too much trouble. Once he pretty much concluded all the ponies had left, he decided to start sneaking his way to the building.

“Hmmmm, alright no one seems to be noticing me,” he said to himself.

Once Anon made it to the school, he quickly peeked through one of the windows just to make sure Cheerilee didn’t sneak out without him noticing. He was able to spot her at her desk arranging some paperwork. He slowly then made his way to the door and could hardly contain himself. Anon then casually pushed open the door and walked into the classroom.

“Excuse me, I have packages for Miss Cheerilee?” the human said with a smile, catching the mare’s attention. She looked up at you and was caught off guard by your unexpected presence.

“Oh Anon?! W-what are you doing here”?

“I thought I'd drop by for a visit and see how my favorite teacher is doing”. This comment caused the pony teacher to blush.

“Aww how thoughtful of you…..um are those for me”?

“Yes ma’am. I thought it would’ve been nice to give you something, especially if you might’ve had a long day. No need to thank me,” Anon said with a wink. Cheerilee’s blush was almost becoming visibly noticeable.

“Oh my these flowers smell amazing! You sure know how to make a mare feel like she’s special….well how was your day?” she asked while putting her gifts on her desk.

“Quite the adventurous one, especially exploring all over town getting your stuff. Also I got trampled by Pinkie but that’s just normal at this point. How about your day, the kids behaving”?

“For the most part, yes. One young filly was being a little disruptive and was causing some drama with other students. Other than dealing with those young ponies, I’m just ready to go home for the day”.

“Quite the rough day, huh? Well it seems like I did the right thing bringing you some gifts,” Anon said chuckling.

“Really though, I can’t thank you enough for this. You’re an amazing friend, Anon,” Cheerilee said walking over to Anon and giving him a hug.

The two exchanged more words, laughs and hugs. They shared the cupcakes Anon had picked up from Sugarcube Corner. About an hour passes as the sun continues to make its way towards the horizon. Anon takes note of this and informs Cheerilee.

“Sun is starting to lower down, wanna go grab a drink or two?” Anon asked.

“I think I’ll pass tonight, I just want to be in the comfort of my home. But if you want to hang out, you can come with me to my place”?

“Fine by me, do you need help getting your stuff”?

“Yes, if you could be so kind to do so”.

Once the two made their way out of the school, they both made their way to Cheerilee’s place. Anon had been there a few times before, mostly for poker and movies. It was halfway across town, hopefully no ponies would call them out and start making assumptions about them being together. That would be the last thing Cheerilee would want. Fortunately for the two, no one seemed to bother them.

The two finally arrived at Cheerilee’s house, it was a relatively average sized house. It can easily fit more than one, but Cheerilee seemed to enjoy having all the space to herself. As the mare searched her satchel for her house keys, Anon was eyeing her body. To Anon, Cheerilee had quite the body for a pony. Smooth curves, a well-defined posterior and child bearing hips. She was basically that one hot high school teacher that every male student crushed for. But Anon wondered if Cheerilee ever took notice of her own shape. Did she take pride in it? Does she exercise her body to make it more unique? All these questions flowing through Anon’s head as he continued to gaze over the mare next to him. He was too busy observing to even notice that Cheerilee had found her keys and is looking at him with a confused look.

“Ummm Anon? Are you alright? You’re looking at me like there’s something wrong”. This question caught Anon off guard and he almost panicked. He wondered if she caught him staring at her ass. He had to think of a response quick.

“Uhh, oh I’m sorry. I was watching this mosquito that landed near your cutie mark. I was about to smack it off but then that would’ve probably been rude of me not letting you know. I also debated myself since it would’ve looked as if I was smacking your ass. I didn’t want to give off the wrong idea. I was actually about to point it out to you before you caught my attention,” Anon said practically starting to sweat. Even though Anon’s claim was mostly a lie, there actually was a mosquito about to suck blood from Cheerilee.

“Oh wow! That’s a big one! Don’t worry dear, I got it,” the mare said as she suddenly smacked her flank with her hoof. The impact caused her butt to shake. Anon witnessed this and he almost felt his crotch start to tighten. “Well with that little insect out of the way, shall we go inside”?

“After you, miss,” Anon said holding the door for Cheerilee.

“Why thank you sir”.

Once the two entered the house, Cheerilee threw her stuff on the counter in her kitchen and she made her way to her couch. Anon followed and sat down next to her. A few moments of silence, Anon was looking around the room and his eyes spot a frame that shows a picture of what looks like Cheerilee.

“Hey is that you in that picture over there”?

“Hmm? Oh yeah that’s me alright heh...I had crazy hair back in the day”.

“It totally looks like you were rocking an 80s hairstyle,” Anon said as he got up to get a closer look at the picture. “Oh yeah this is totally you if you were around during the 1980s. Seems like you were jamming to some tunes in this picture”.

“The 1980s? I assume that’s a time period that humans recall”? Equestria’s calendar never really tracked the years as it’s just the seasons that’s widely used. It never made sense to Anon whatsoever.

“Oh right, you ponies don’t track years. Well to give you a perspective, the current year for humans is 2019. The 1980s was basically 30+ years ago. It was a time period that was very interesting. The music was very poppy, the Soviet Union was starting to fall, climate change was starting to become well known, AIDS was spreading like crazy. It was a very weird decade. I just mentioned your hairstyle having an 80s look because that’s how pretty much almost every female musician in the 80s kinda looked”.

“Well that picture of me was taken many seasons ago. I guess that means ponies are kinda behind in terms of hairstyles,” she said with a giggle. “But did almost every female musician share the similar style like me in that picture”?

“For the most part, yes. Not all however, but there was a wide variety. It wasn’t just women, men had a similar look also. Just don’t even get me started on the catchy tunes they would produce”.

“I’m actually intrigued by the idea. Do you happen to have some of the songs on you”?

“I mean, I can play some off my device. But don’t blame me though if one of these songs gets stuck in your head”. The device in question was a phone Anon managed to still have on him. Since Equestria has no service, all Anon can really do is play songs or games he’s already have downloaded. Equestria does have electrical sockets however, so Anon has been able to charge his phone when needed.

Cheerilee just laughed at Anon’s comment “Haha, they can’t be that catchy”!

“Ohohoho you’d be surprised. Trust me on this”.

The two exchanged laughter for a few seconds as Anon started to scroll through his device looking for his 80s playlist. One thing was certain that this night would most definitely turn out to be a blast from the past. Anon found the playlist and hit shuffle play. The first song that comes on was Depeche Mode's Just Can't Get Enough.

"Ohhh god damn it...," was all Anon thought to himself as the signature synthesizer starts playing.

Author's Note

I promise next chapter won't be just constant 80s references. I have ideas for skipping that filler content anyways. Next chapter will start to get pretty naughty.

I'm sorry for the delays on these chapters, been busy as of late but I'm still working on this when I have the time, don't worry.

Also for any Depeche Mode fans who finished this chapter, just know that I have nothing against the group.

Ch 3: Appreciation

An entire playlist goes by and Cheerilee will not stop quoting lyrics from Billy Idol. At least Anon could tolerate Billy, he was just thankful Cheerilee wasn’t repetitively singing along to any one hit wonder song. Both Cheerilee and Anon also managed to slam down a few drinks while enduring the music from the past. Anon didn’t know how much alcohol consumption was needed for a pony to be considered intoxicated, but Cheerilee was clearly wasted. She only had three rounds to begin with, or so Anon thought.

“I gotta say Anon….that music of yours is pretty radical. By Celestia is it just, yeah”.

“I mean I guess. It was good for its time”. The two creatures laid there on the couch. The room was so quiet, Anon could almost hear Cheerilee’s heart beating rapidly. Little did Anon know, his presence was making Cheerilee excited. Her estrus started to kick in and it’s really starting to torture her. “Well, I don’t know about you Cheerilee but...I think I’m gonna head home here in a minute before it gets too late. You may want to get some rest too”.

“N-no! Don’t go yet! The night is still young and we still have so much to do. Don’t leave me...please stay”. Tears started to form up in Cheerilee’s eyes. Anon knew alcohol can have an effect on one’s emotions, but this sudden change seemed a little unusual to him. It’s as if Cheerilee suddenly became bipolar. The big question was why she was even crying in the first place.

“Well now, don’t get too excited. You act like I’m gonna abandon you forever and never want to see you again. I just want some sleep, that is all”.

“You can sleep here at my place! We can have a sleepover together and….oh wow I haven’t done a slumber party in so long! But it’ll be fun, please”?

“Look Cheerilee, as much as I’d love to have a slumber party at your place, I know for a fact that you’ll keep me up all night in the current state you’re in. Plus you have to return to school tomorrow and continue doing what you do best, tea-”.

“NO, FUCK THAT SCHOOL!!”. This sudden outburst startled Anon. Never would he have thought to hear those words come out of Cheerilee’s mouth. But then again, she’s intoxicated, she obviously didn’t mean it.

“Whoa now, you shouldn’t go around saying stuff like that. I know you’re drunk and you’re just saying things, but come on. You love teaching, it’s your specialty”.

“Well not anymore! I’ve just about had it with those ungrateful, disrespectful heathens! I’ve tried so hard guiding them but they’ve just gotten more stubborn and disruptive, I can’t take it!”.

“Okay let me stop you there. Something obviously happened today, something you didn’t tell me. Care to explain?”. Suddenly Cheerilee just explodes emotionally. She’s crying and is very angry. Anon sat beside her and held his arm around her as the mare dug her face in his shirt. “Let it all out Cheerilee, it’s always a good thing to let loose some steam. Now...just what happened earlier today?”.

Cheerilee sniffed and wiped her face as she looked up at Anon. “Look, I don’t want to talk about it. It’s my personal business and I just want to know that I’m appreciated for what I do by someone”.

“If it makes you feel any better, I appreciate you for all that you do and ESPECIALLY how you’ve been there for me since day one. There are creatures out there that are grateful for how you impact them, I am one of them. Without you, I probably would’ve found a way to leave Equestria and move elsewhere where I felt more welcome. Once you came along, that idea disappeared from my head”.

“I..I never knew how important I was to you. Do you really mean all that you say?”.

“Yes, I do. The kids you teach are only too stubborn to understand gratitude, but they’ll catch on eventually. I wouldn’t take it too personally, instead just continue being you and know that there are creatures that support and appreciate all that you do”. Cheerilee’s tears seemed to stop forming in her eyes, which was a good sign to Anon. The mare shuffled on the couch for a few seconds before letting out a small sigh and then coming in for a big hug.

“Thank you, Anon. Thank you very much for supporting me....even if I'm gonna forget all this by morning”.

“Hehe..anytime”.

The two sat there for a brief moment, embracing one another. Once the hug ended, Cheerilee laid herself back on the couch and stared up at the ceiling. Many thoughts flowing through the mare’s mind. Her heart beating continuously and her marehood growing even more moist by the second. She needed someone to claim her, she had never experienced the touch of a man before. She wanted Anon more than ever now.

Initially Cheerilee never had any thoughts of wanting to be Anon’s mate. Hell, when her and Anon were starting to become best friends, she never viewed him more than just a close friend. However, overtime she started to develop feelings for the human as each time they saw one another, it sparked a new feeling in her chest. Now the feeling was undeniable and estrus wasn’t helping either. Cheerilee was determined to claim her prize before dawn.

“So may I ask what you guys discussed in class today at least?”.

“Huh? Oh! Ummm….we were discussing social behaviors and how bonds grow. We discussed the concept of having a special somepony which disgusted some of the students”. Cheerilee giggled at the end of her sentence. It was never a surprise when a child would be disgusted by the thought of romantic relationships.

“Have you ever had a special somepony, as you guys call it?”.

“I did once, but that was short-lived,” Cheerilee said with embarrassment.

“Been there, done that”.

Back in Anon’s world, short-lived relationships were extremely common. Most people were typically in a relationship just for sex, not for the long run. Commitment issues was a huge key factor to short-lived relationships. Many people now lack that type of character and this resulted in high divorce rates worldwide. It was just a game of how many people can one add to their body count. A moment of awkward silence ensures until Cheerilee hesitantly started to speak.

“H-hey Anon?”.

“Yeah?”.

“W-what’s it like to be truly in love?”.

This question caused Anon to stop for a moment and think. Had Anon ever felt true love for someone? Could he even explain the feeling? A few seconds pass by as Anon starts to respond.

“If you ever heard the saying of butterflies in your stomach. It’s basically that. You feel a weird sensation within yourself. It’s like something is radiating inside you, it makes your heart rate go up. I don’t really know much else since I’ve never really felt TRUE love for someone, but perhaps I just haven’t found the right one”. Anon looked down at the ground for a moment to gather more thoughts to possibly add to his explanation. He figured though he gave a fair description. He then turned his head up.

“Why do you ask Cheeril-MMF!?”.

Anon was cut short from his question by the sudden realization of his lips being pressed against by Cheerilee’s own lips. She lunged forward at Anon and implanted the kiss for a few seconds before she let go and scooted away from the human.

“W-what was that??”.

Author's Note

The lewds are coming soon. The lewds will also be the last chapter. So only one more chapter that I'll probably have to rewrite a few times!

I should get someone to proofread my work honestly, but likewise, feel free to offer feedback.

Ch 4: Caressing The Teacher

Author's Note

Finally decided to throw the conclusion to this delayed story. It's also pretty much my first attempt at trying to write decent clop, so much feedback would be appreciated.

I do apologize for the near 2 month wait for the final chapter, there was a setback for multiple things within my life and such.

But anyways, THANKS FOR STICKING AROUND AND ENJOY THE FINAL CHAPTER!!

Ch 4: Caressing The Teacher

“Seriously Cheerilee, what was that?” Anon asked with a puzzled look on his face.

“Well, a kiss obviously”?

“I got that part but….why”? Anon had many thoughts flowing through his head at once. The most important one however was the fact his best friend just suddenly kissed him on the lips. All this time he’d been trying to win her over and suddenly here she was practically finishing the job for him.

“Because unlike other po-I mean creatures, you’ve showed me what it feels like to be loved. Not loving me because I’m a teacher, but as if I was regular pony…..treated like she’s special”.

“So in simple terms, you have a hot spot for me because I’ve been treating you like a special pony for the past year?” Anon said with a big shit-eating grin. Cheerilee just looked away from Anon and tried hiding her obvious blush.

“N-no that’s not what I meant I-I mean…yes and no”?

“Okay look Cheerilee, clearly there’s something you’re trying to tell me and something is holding you back. Just be honest with me. Besides, you’re dripping a little from behind”. Cheerilee’s blush grew even more apparent. Anon was right, Cheerilee wanted to tell him something. She wanted him more than anything right now and with her estrus season kicking in, it’s really helping her out. Cheerilee then presses her hoof on Anon’s chest.

“Screw it…..Anon I want you to be my special somepony, I want to be your cutie patootie, I just…..Anon please. I know you’ve felt the same way for me for awhile now. Now I’m ready, I need you Anon”. Cheerilee was practically pouring a waterfall from her behind. Her pussy was on fire and demanding for a good pounding. The message was clear to Anon and his dick started to harden. Cheerilee then placed her hoof on his growing member and started rubbing softly. This caught Anon by surprise.

“Ohhh...sh-shit Cheerilee, that feels so good”.

“Please Anon, I need you now”.

“Hehe...can’t say no to a lady now can I?” Anon said as he started to unzip his pants. Once his pants came off, he then pulled down his underwear and thus revealed his excited member waiting for some good horse pussy. “Hope you’re proud of me father, I’m actually gonna fuck a horse,” he thought to himself as Cheerilee stared at his erect penis. A few seconds pass until Cheerilee starts to motion her muzzle over to Anon’s tip, embracing the scent it gave out.

“Mmmmm…..you smell nice,” Cheerilee said as she started to lick Anon’s shaft.

It had been far too long since Anon last felt someone else touch his junk. He was gonna enjoy every second of this. After a year or so of trying to win Cheerilee over and now he’s finally gonna fuck her. Cheerilee’s licking, especially on the tip, was really driving Anon close. Anon had always been sensitive in the lower tip area, he would cum in less than a minute if someone continuously hit the right spot.

“O-oh...fuck!,” Anon moaned.

“Getting close? I’m surprised you managed to hold on for more than 10 seconds”.

“Y-yeah well humans have a lot more stamina than horses do, you’re in for a surprise”.

“I’m looking forward to it, dear”. Cheerilee then moved her mouth over the tip and started to suck further and further downwards. Anon was really trying his best to hold on. This was the best blowjob he’s received yet. Perhaps it had something to do with the mouth of a pony compared to a human, but either way human blowjobs were nothing to Anon now.

A minute or two passses by and Cheerilee has been deep throating Anon’s cock for most of that period. Each suction that came from Cheerilee’s mouth brought Anon closer and closer to cumming. He couldn’t even imagine what horse pussy would do compared to human pussy. Anon felt himself approaching climax.

“Cheerilee…I’m about to..”. As those four words came from Anon’s mouth, Cheerilee then starting sucking his tip like a vacuum as if she knew that’s where his sensitive spot was. Anon couldn’t hold it anymore and after one more suck from the mare, Anon came. His semen filled Cheerilee’s mouth as she starts to swallow it all. This surprised Anon considering he didn’t think Cheerilee was one to swallow.

Once Cheerilee finished swallowing, she let out a long exhale and kissed Anon on the lips. The two kissed for about thirty seconds before Cheerilee quickly let go and turned herself around, presenting herself.

“I-I can’t take it anymore, I need you now! Rut me like there’s no tomorrow!” Cheerilee said as her marehood was dripping puddles. Setting himself into position, Anon then slowly approached the mare and starts to align his junk with Cheerilee’s pussy. Anon could feel the heat emanating from her marehood. She really needed this and Anon was gonna give it all to her.

“You ready, Cheerilee”?

“Yes, just stick it in me already”.

On cue, Anon slowly brings his dick further towards the mare’s vagina until contact is made. Anon then begins to thrust inwards which brings a yelp from Cheerilee.

“You alright? If something hurts, let me know,” Anon said with concern.

“I’m fine, I just haven’t felt this in awhile, I’m just getting used to it”.

With that reassured, Anon furthermore thrusts his dick deeper into Cheerilee’s pussy. If Anon had to compare the feeling of horse pussy and human pussy, horse pussy ranks superior. He felt Cheerilee’s vaginal muscles start rubbing against his cock, he couldn’t be anymore harder than he was now.

“Ahhhh fuck!” was all Anon could say in response to the wonders of horse pussy.

Anon started to pick up the pace thrusting in and out causing cute little moans from the dark pink pony. He wondered how long mares last before they cum. A few more thrusts answered his questions once he felt his crotch moisten up from the mare’s vaginal fluids. It was just a matter of time before Anon would cum as well.

“A-Anon are you close? I want you to fill me up now,” Cheerilee said with a whine.

“I’m getting there, just a little more thrusts”. Cheerilee then started to assist Anon’s thrusts by moving her body in opposite directions against his thrusts, burying his dick a little deeper inside her pussy. Anon started to feel himself getting close.

“Ch-Cheerilee...I’m getting close, just a little m-more”!

One thrust, two thrusts, and three thrusts later, Anon’s balls started to tense up as he felt the flow of semen rush through his junk ready to explode in an instant.

“I’m cumming, FUCK!” Anon said as he gave one more thrust inwards as deep as he possibly could. His cock exploded as his sperm spewed inside Cheerilee’s inner vagina and womb. Human pussy is forever off the list for Anon.

“Oh honey...your cum feels amazing”.

The two sat there for a few seconds as Anon finished unleashing his load. Anon then turned Cheerilee around to face him and gave her a kiss. At first Cheerilee was startled by the sudden kiss, but quickly returned the favor. The human and mare embraced each other’s presence as their relationship had just achieved new levels that will only continue to grow.

“Thank you Anon, I love you so much…,” Cheerilee said as she wrapped up the kiss.

“Thank you for letting me help you, I love you Cheerilee”.

Both Cheerilee and Anon sat there on her messy, cum-stained couch for a few minutes in a tight hug and exchanging a few more kisses.

“So….are you ready to deal with your students tomorrow morning?” Anon said petting Cheerilee’s mane.

“Yeah, I feel much better now about it, thank you”.

“Well, I shouldn’t keep you distracted, I’ll probably be heading out for the night, but I’ll see you tomorrow”.

“N-no wait! Can you please spend the night with me? Please?” Cheerilee begged with adorable puppy eyes. Anon couldn’t resist such an offer anyways.

“Haha, of course I will ‘cutie patootie’,” Anon replied with a wink.

The two then made their way over to Cheerilee’s bedroom where they would wound up fucking each other even more as the night goes on. Everybody is gonna have fun tonight.

THE END