Chapters Anon has sex with the mane 5
Bet you’ve never heard of this scenario before. A man named Anon was randomly transported to the world of Equestria, and he’s going to have sex with somepony.
When I landed in Equestria, I appeared in the center of maretime bay with a big flash of light. It even shattered a ton of windows. Many of the ponies in this land ran and screamed thinking I was some kind of monster, and many ponies still believe that I am that monster, just waiting to attack at any moment. But thankfully five ponies didn’t think that way, they welcomed me into their homes, made me feel comfortable and secure, and continue to show me that kindness to this day. Their names were Sunny Starscout, Hitch Trailblazer, Pipp Petals, Zipp Storm, and Izzy Moonbow. They were the nicest group of friends I could ask for, and I wouldn’t trade them for anything in the world. But now I’m caught in a bit of a dilemma, because I’m pretty sure they ALL want to fuck me. I mean, I do to, I just don’t want to make it seem like I’m picking favorites if I do fuck one of them.
I’m also not sure if all of them are actually into me. With some of them though, it’s pretty easy to tell. Like Zipp and Sunny, they SO want inside my pants. Sunny got drunk one night at a party and practically outright said she wanted to fuck me and was insisting I do it with her right in that moment. But she was so goddamn drunk i wouldn’t have felt good about myself if i had sex with her. When she got sober she didn’t even remember anything from that night so I didn’t want to push the topic. With Zipp, she has always been very flirty with everypony, but when it came to flirting with me it seems less playful and more genuine. Another reason to suggest she might be into me is the fact that I’ve “accidentally” seen her lower lips on numerous of occasions. I swear she’s doing it on purpose, she’s was always swaying her hips and tail more exaggeratedly when it happens, and every time I caught a glance of it, she would give me a cheeky smile. She definitely knew what she was doing.
The other three I have very little evidence to support the idea they want to bone me, but it’s still worth a mention at the very least, cause they’re very hard to ignore.
Hitch is the only other male of the group, and he’s actually the local sheriff. Although I’m fairly certain he’s straight as an arrow I can’t ignore the time he’s come off as gay around me a few times. There was this one time I gave him a side hug and he seemed to enjoy it way too much for a straight stallion. I would also catch him looking at me when I’m doing manual labor around town with my shirt off, and when I were to look back at him, he would always look away with the faintest hint of a blush on his muzzle. The next pony is Izzy, who is very sweet and I’d consider her to be my closest friend out of the whole group. She also likes to ignore my personal space a lot, especially around my groan and face. She also has a tendency to have her hugs last a little too long, it’s also just the general vibe she has when me and her are alone. It seems very flirtatious and every time we’re together it could easily turn into a sexual encounter if one of us had the gall to take that next step. Last, but certainly not least is Princess Pipp. She’s a social media royal popstar, so first of all, out of my league. But she seems to really enjoy my company at least, so that nice. She always made it a habit of taking a photo with me any chance she could and is very adamant that we hang out more often. She also asked me a while back if I have a “marefriend,” which I of course respond with no, which caused her to respond with a very sudden sexually comment about how big I must be considering how tall I am and that anypony would be luck to be rutted by me. That’s about the extent of it with Pipp, but you don’t really say something that sexual explicit to someone if you don’t think about them in a sexually manner as well. Why else would she bring up my dick size if she didn’t want to fuck me then?
There is more evidence to suggest they may be lusting over me, but those are just the big ones that pop into my head first. I try not to think about having sex with them all the time though, they are my friends first, eye candy later. Speaking of candy, I’m now in the mood for having something sweet to eat. Might as well drop by and visit sunny while she’s running the smoothie cart she works at.
I rounded the corner and as luck would have it the smoothie stand didn’t have a line, and Sunny had her back turned to the counter while she organized the small work area behind her. I walked up and knocked on the counter gently to get Sunny’s attention.
“I’ll be with you in a second.” Sunny said without looking back.
“Why, you aren’t busy?” I said jokingly.
Sunny began to turn around with a scowl on her face, thinking I were a rude stranger. Her expression quickly lightened up when she realized it was me though.
“Oh it’s you!” Sunny said with a laugh. “I thought you were just some asshole.”
“You’re not completely wrong, I am an asshole.” I joked.
“Stop it, you’re so the opposite of an asshole.” Sunny complimented.
“That’s cause I like you. If I didn’t like you, asshole Anon would come out and greet you.” I said, as began to lean on the counter.
“well thanks.” Sunny said with a smile. “I like you too… uhh, hehe, umm. Why did you come over here again? Just visiting?” She said quickly with a blush forming on her face.
“I was in the mood for one of your smoothies.” I said, smiling at her earlier stammering.
“Oh okay. Well, what flavor would you like?” She said with a smile.
God, she was adorable. Her radiant smile was incredibly infectious, and her eyes sparkled with such a beautiful aura that I could stare at them all day. Her mane was so neatly tended to, and that little rainbow streak in her hair was just the cherry on top of her already adorable features. God, what I wouldn’t give to make out with that beautiful face of hers. Her soft natural lips would feel heavenly pressed against my own. I could only imagine how they would feel wrapped around my- Dammit Anon, I just said I didn’t want to think of my friends in a sexual manner all the time, and here I am. Thinking about fucking her. Just ignore it Anon. You want a smoothie, not sex.
“Grape please.” I answered, as I internally wrestled with my sexual urges.
“Coming right up!” She said enthusiastically. She turned around to pour my chosen smoothie flavor into a cup for me.
I don’t think she meant to, but she flashed me her loins as she did this. Usually when Zipp does this I pretend like I didn’t see it, but the sexual urges I was having at this particular moment in time prevented me from tearing my eyes away from her lower lips. I bet it would taste better than her smoothie… her flank is pretty nice too. It’s thick and plump makes me wanna take a bite out of it.
Goddammit, knock it off Anon.
Sunny turned around with my grape smoothie balanced on her hoof. “Your smoothie sir.” She said with another smile.
“Thank you.” I said as I dug into my pockets for some bits, while also multi tasked and rearranged my trousers snake to be less noticeable as well.
“Oh, wait. Do you want any toppings?” Sunny said with an eyebrow raised.
My perverted mind began to race as I jumped from sexual topic to sexual topic, all because she said toppings . I imagined getting behind of her and rutting her silly until her brain would short circuit. It would be so hot to fuck her right where she stood, right behind that counter. I could easily do it too, nopony was around and she did drunkenly admit to me her sexual desires. But did I really want to risk it?... Fuck it.
“Tsk. you?” I said.
“W-w-what?” Sunny said with a blush starting to form on her muzzle. She was probably in genuine disbelief at what I just said, so I clarified.
“I said,” I began as I slowly bent down closer to her. “I want you. On top of me.” I ended with a boop on her noise.
Her blush began to glow brighter. “Are you coming on to me right now?” She said with a smirk.
“Depends. Do you want me to be coming on to you?” I say with a smirk, fairly confident in what her answer is gonna be.
“Yeah…” Sunny said sheepishly.
I smiled, then checked over both my shoulders to make sure nopony was anywhere near us.
She gulped before nodding her head rapidly with a huge grin on her face. I let out a small chuckle at how cute that response was. Then I leaned in real close and whispered into her ear.
“Then close up shop, cause I’m fucking you right where you stand.” I said as I lightly grabbed her chin.
Sunny squealed in excitement, she could barely contain her enthusiasm as she lowered the shutters to her smoothie stand, nearly catching my fingers in the shutters. She then leaned out the side of the stand and gestured for me to come inside. Once I entered she pretty much slammed the door shut behind me and tackling me to the ground, causing the whole stand to sway from my impact. I hit the ground pretty hard, mostly cause I wasn’t expecting her to be so… hungry for me.
“Oh my gosh, I am so sorry.” Sunny said with a blush. “I guess I got a little carried away.”
“Hey, you’re fine.” I said as began to sit up. “But let’s take this one step at a time. Okay?”
She nodded as she backed up off my lap. “Right. So, you want me to s-suck you off first?” She said nervously.
“Of course I do. But do you?” I ask. I’m teasing her, but I’m also making sure I get verbal consent before we continue.
“Yeah. I really want to.” Sunny said, biting her lip in anticipation.
I obliged and while I still sat on the floor, I unbuckled my pants and slid them down to my ankles. Sunny began to paw at my bulge through my underwear, letting out a shaky breath as she anticipated my members inevitably release. She didn’t strike me as somepony who has sex often, so she was bound to be a little nervous as well. I gotta make sure I take it slow with her.
Shortly after I had that thought though, she lunged forward and pulled down my underwear with her teeth, and then gripped the base of my cock with her hoofs and slammed her head down, taking a decent amount of my cock in her mouth in one go. The shock of having nearly half my cock enveloped in her warm maw nearly made me finish right then and there. So ‘taking it slow’ went out the window pretty much immediately, this horny horse wanted me now. She eagerly sucked me off while her hoofs, well, she didn’t really know what to do with her hoofs. She just rubbed my pelvic area and a bit up my chest with her soft hoofs while she focused on swallowing more of my member each time she bobbed her head.
Sunny then closed her eyes and moaned, sending a delightful vibration through my member, which made me moan as well. She giggled at my moan and she then raised her tail into the air as she shook her rump. I reached down and scratched her ear as she continued bobbing her head up and down my shaft. The saliva that coated my cock began to drip down my balls, and I felt a pressure begin to build up in my loins already. Sunny then stuck her tongue out to lick the underside of my cock as she eagerly devoured all she could fit in her maw, licking my balls slightly every time she reached the base of my member, or at least as close to the base as she could fit.
“Sunny, ahh holy shit , wait a second.” I said gently pulling her mane back.
She finally released my cock and wiped some of her saliva away from her lips.
“No you’re fine, trust me.” I said as I pet her mane. “I just want to actually fuck you before you make me cum.”
“Yeah, I did too.” She said with a blush “sorry, I’m just, really excited that we’re actually doing this.”
“And I’m flattered by the eagerness, but you gotta slow down a bit.” I said as I cupped her cheek.
“Right. Got it. Slow. ” she began to climb up my chest and slowly leaned in for a kiss.
They wasn’t any tongues involved, they were just soft, simple, and intimate smooches. She then hooked her hoofs around my neck as she positioned her loans over mine. We separated from the kiss after thoroughly enjoying the sensation. Then Sunny proceeded to push on my chest until I was lying completely flat on the floor. She now stood on my chest, looking down at my member and trying to position herself correctly on it. Her limbs shook in nervous excitement, and she bit her lip in anticipation.
“You ready?” I asked as I tilted her head upwards with a finger to look at me.
“I’m been ready, Anon.” She said with a blush forming on her face.
Without another word spoken between us, I lined up my prick and Sunny lowered her hips onto it. We both shuddered as I entered her and she continued to lower herself down until she reached the base, letting out a heavy groan as she bottomed out. I grabbed her hips as we began to get into a rhythm, starting off slow but we gradually went faster the more we fucked. She closed her eye and tilted her head back, allowing herself to be lost in a sea of pleasure. I grabbed her waist more firmly as she bounced on my cock, making her smirk and she opened her eyes slightly to peer down at me.
“You better start fucking me harder than that.” Sunny demanded.
I rammed my pelvis into her in response to that statement, causing her to shriek in pleasure. She rolled her head back as she continued to grunt and moan into the sky. She then leaned forward and placed her hoofs on my chest, getting ready to go faster. But before she could, we both had to stop when we heard a voice from outside call out.
“Uhh, Sunny? You okay in there?” Said a pony that sounded a lot like one of Sunny’s friends, Posey Bloom.
She scared the shit out of us and made our hearts skip a beat. She also sounds like she was right next to the goddamn shutter that blocked her visibility from what’s going on inside. Unfortunately it didn’t block sound, which would’ve been nice to know before we started.
“uh… yeah, I’m fine.” Sunny said trying to come up with an excuse. “I was just, uh, ya’know… umm.”
“spilt something.” I whispered.
“I just spilt something!” She yelled back to Posey. “It got all over me, and It’s all in my fur now! And it surprised me, so that why I screamed!” She cringed, hoping Posey bought that terrible lie.
“Oh okay. That sounds awful, hopefully you get all that stickiness out of your fur.” Posey said, causing Sunny to smirk and gyrate her hips on my cock, while she stared down at me with hunger in her eyes.
“Yeah, I’m making sure I get all the stickiness out.” She then slammed her hips down to emphasize her double entendre. Causing me to let out a stifled grunt as I tried desperately to stay quiet.
“Alright, see you later Sunny!” Posey announced as she began to walk away.
“See ya, Posey.” Sunny said as she began to bounce on my cock again, this time with more quiet moaning.
“That was close.” I said as I rubbed her hips.
“Too close.” Sunny said as she rubbed her clit with her hoof. “Nice excuse by the way.”
“No problem. Ugh , coming up with good lies, is one of the perks of being an asshole.” I said with smug grin through my moans.
“Shut up,” she said with an eye roll before leaning close to my face.is a mess I need to clean up.”
Wow. I have to give it to her, she’s good at dirty talk.
I obliged her command and jammed my cock deep inside of her, causing her to grit her teeth and moan, trying to stop herself from screaming out load again. We slammed our hips together again and again, beginning to get back into the rhythm we were in earlier. She covered her mouth to stifle her moans, as her eyes rolled back into her head. I continued to slam my prick into her sopping wet pussy, making it harder for her to stay silent. Suddenly her demeanor changed and she took the lead, slamming her self down onto me hard. I actually had to bit my knuckle to not make any load noise because of that action.
“Come on Anon. Fuck me.” She said with hunger in her voice.
I was doing that earlier, but Sunny has now taken the reins and is now the one doing the fucking. I repositioned my legs to better thrust into her, but once I did that she repositioned as well to still be the dominant one.
“Come on motherfucker. Harder.” She muttered.
She’s got a lot of energy, almost too much energy. I almost can’t keep up with her, especially when she demands me to go harder and every time I do she fucks me harder in response, then demands me to fuck her harder again. I stopped thrusting for a moment, because I had to rest before I thrusted into her again. But she continued slamming herself down onto me, making the pressure in my loins build up as her tight pussy stroked the length of my cock.
“Don’t stop now.” She said, while refusing to relent, and continued to slam herself down onto me, causing the smoothie stand to sway slightly.
At this point I kinda got a little annoyed with her, I couldn’t keep up with her like this. So I had to change the playing field a bit. I grabbed her and pulled her into my chest, which caused her to yelp in shock at the suddenness of my actions. I bear hugged her and secured her to my chest as I rammed my dick into her faster than before. She squealed as I fucked deep into her cunt as fast as I possibly could, making her moan loudly, completely forgetting to be quiet.
“F-fu-u-uck.” she stuttered. “oh my gosh, you’re so fucking good! Fuck me just like that, holy shit!” She screamed out.
I laughed at her cute little moans, and i started scratching behind her ear, making her hum in delight. I then tugged on her tail which made her gasp, and then she giggled in pleasure as she bit her lip. As I continued to slam myself into her I felt the pressure in my loins building up fast, but I did not want to finish yet. I had to push Sunny over the edge. I tugged her tail a little harder, causing her to squeak in pleasure. I then leaned down and slightly nibbled the tip of her ear. She liked it, her moans changing in pitch at the sensation, but I wanted her to cum before I did. After a quick thought on how I was going to accomplish that, i decided to slip a finger into her asshole. Now that did it for her, she gasped from the sudden intrusion and her entire body clenched from sensation of my fingers wiggling inside her. Her vaginal walls contracting and squeezed around my cock, and her anus did quit the same around my finger as she finally reached her climax. Her orgasmic fluids sprayed all over my groin as she screamed in pleasure into her hoof. I wasn’t far behind now, so I leaned into her ear, and with a heavy sigh I asked-
“where do you want it?”
“Inside,” she said almost immediately. “I want it inside me, I'm not in heat, just cum inside me, PLEASE!”
That last part made me jump from how load it was and I slapped my hand over her mouth instinctively. She didn’t protest to that action, she actually used it as an excuse to moan as load as possible as I finally released my load into her. I shoved my dick deep inside of her as my spunk began to paint her inner walls white, I lost track of how many times my seed was pumped inside of her. The muscles in my legs began to get tired from being propped up in an elevated position for so long, so I let them collapse to the ground, and when my pelvis hit the ground it caused my dick and finger to pop out of her soaking wet pussy, and tight anus respectively.
“Holy shit…” Sunny sighed. “That was fucking incredible.”
“Was it? I couldn’t tell.” I said jokingly.
Sunny laughed, while still trying to catch her breath. “Hey, I gotta ask you something. Don’t get me wrong, I’m happy we did this. But why did you decide to do this with me all of a sudden?”
“I just decided to bit the bullet, cause I kinda knew you wanted to do this with me, and-“
“Wait what?” Sunny said as she raised her head to look at me. “How did you know I wanted to have sex with you?”
“Remember when you got really drunk during Hitch’s birthday party?” I questioned.
“Kinda.” Sunny said with an eyebrow raised.
“Well, you didn’t just get really drunk, you got… blackout drunk.” I asserted.
“Well that would explain why I can’t remember half that night.” Sunny laughed.
“Yeah, well. You basically outright admitted you wanted to fuck me where I stood in a drunken haze.” I said bluntly. “I didn’t do anything with you cause I would’ve felt gross taking advantage of you with how unbelievably drunk you were.”
“Aww,” she cooed as she planted a small kiss on my lips. “That’s sweet.”
“Stop, it was nothing.” I scoffed.
“Whatever you say,” Sunny said as she hugged my neck lightly. “Any reason you picked today to do it with me?”
“Well, I didn’t come down to your smoothie stand with the intention of rutting of you, if that’s what you thinking.” I clarified. “I just got horny, and like I said, I decided to bit the bullet.”
“Well, I’m kinda glad you did,” Sunny said snuggling into my neck. “this was fun.”
Suddenly a knock was then heard from outside, breaking both of us out of our moments of bliss. A different voice was then heard calling out for Sunny. “Sunny? Are you in there?”
Sunny paused to see if this pony would walk away, but she kept calling out for her. She sighed in disappointment before answering the pony. “Yeah, I’ll be with you in just a second.” She then shot me a grimaced expression. “wish we could’ve snuggled some more. ” she whispered to me, disappointment lingering in her voice.
“we could snuggle later tonight if you want. Back at your place. ” I whispering back.
“okay, that sounds good. ” she then activated her alicorn power, and enveloped my body and clothing in her magic. “See you then. ” she said before quickly pecking me on the lips.
And just like that, I was popped out of her smoothie stand and dropped onto a distant alleyway. I quickly got up from the floor, and looked down, thank god she put my pants back on. She didn’t zip them up though. I quickly zipped them up myself and looked around to make sure nopony was around. No Pegasus was flying above. Nopony was to the left. Nopony to the right. Left again, still nopony. Right agai-
“AGH! Jesus Zipp, you scared the shit out of me.” It’s like she appeared out of thin air, inches from my face.
“Sorry, didn’t think I would startle you that bad.” Zipp said with a smirk. “Especially considering how Ballsy you are.” She said with a sultry tone.
I didn’t really know what she meant by that last part, so I just played it off like she didn’t even say anything. “Uh huh, anyways I gotta get going.” I said as began to walk past her and tried to exit the alleyway.
“Go where?” Zipp said as she flew in front of my face again, stopping me in tracks. “Sunny’s place?” That same sultry tone enveloping her voice again.
Oh shit. She heard us.
“No, I don’t have any plans with Sunny today.” I said, lying through my teeth.
“Oh sure, alright.” Zipp then leaned into my shoulder. “So you making Sunny scream and moan was, what exactly? Cleaning up a mess? ”
The fuck? How long was this pervert listening to us?
“Dude, what are you talking about?” I said as I pushed her off my body.
“Stop playing dumb. I know what you did.” Zipp smirked.
“Okay, you got me. What do you want from me, a confession? We were just having a little fun.” I said, a bit more defensively than I wanted it to sound.
“Anon, we’re not in high school. We’re all adult here. You two can do whatever you want.” Zipp said. “I’m just shocked you chose to do it with Sunny, instead of me.”
What.
“I mean, I’m always flashing you, and I know you see it too.”
Oh my god.
“I’m not jealous or anything. Sunny’s a nice mare and all. I would’ve rut Sunny too if I was in your hoofs.”
Holy shit. This is the hardest she ever come on to me. That look on her face is a new look too. Her eyes had a hungry gaze to them, and she bit her lip as she swayed her curvy body in midair in a was that reignited my hard-on. Is she… is she about to bite the bullet like I just did and ask me to fuck her?
“But right inside the smoothie stand? That’s so risky, but so hot .”
She’s been slowly floating closer to me as she spoke, but now she’s inches from my face.
“How bout we do it right here in this alleyway, big boy.”
“I don’t know Zipp.” I say scratching my neck. “It’s way too open out here.”
“Am I coming on too strong?” Zipp asked as she back away from me a bit.
“I mean a little bit, but-“
“Dammit! I’m sorry.” Zipp blushed a little as she hung her head low.
“Hey, it’s okay.” I said lifting her head up to look at me.
“Really?” She asked.
“Yeah, I don’t mind you coming on to me. Honestly, I’m extremely flattered you think of me that way. I wouldn’t be opposed to doing something with you. I just wasn’t expecting you to be so forward so suddenly.” I then cupped her chin in my hand and gazed into her eyes.
Zipp had a bit of a scowl on her face, and she grunted in protest.
“What is it?” I asked.
“I kinda get off to doing it outside. ” Zipp grumbled under her breath as she blushed.
“Really? What are you, an exhibitionist or something?” I said with a smug smile.
“N-no, nothing like that.” She said while she waved her hoofs in opposition. “I don’t want ponies to watch us, I just like doing it outside… and I also like the risk.”
“How often have you done it outside.” I said, kinda enjoying the irony of Zipp starting this conversation trying to get me embarrassed, but now it’s her stammering like a fool.
“Uhh, haha… a lot .” She said with her blush brightening.
“Anything else you want me to do? Other than fuck you where you stand.” I noticed she got a little flustered from the way I said that.
“Umm. I… want you to be rough.” she said with an awkward smile.
“What do you mean by, rough ?” I said.
“I want you to… you know, throw me around… use me.” Her blush brightened and she then began to laugh nervously as she covered her face with her hoofs.
“So what?” I said as I grabbed her hoof out the way of her face.
“Yeah,” She smiled. “a-and when I said toss me around , I-i meant I want you to hurt me. Slap me, leave bruises on me I don’t care. just make it hurt.”
“Well, in that case,” I said as I grabbed both her hoofs, and placed my other hand on her chest. “I’m gonna leave you quivering and begging for mercy after I’m done with you.”
I then plucked her out of the air, and slammed her into the nearby wall, forcing the air out of her lungs from the sudden force. Her hoofs were now pinned above her head, and her wings were outstretched in arousal. Her eyes were wide in shock at being suddenly shoved against the wall, but a small smile creeping onto her face. She was going to love this. I leaned in and locked lips with her, meeting in an aggressive and sexual kiss. Our tongues interlocked in a wet and sloppy make out sessions, spit and saliva dripping down both our chins as we quickly lost ourselves in the moment. I also stopped pinning down her hoofs so I could firmly grab her face as I continued to aggressively kiss her. I pressed my body against her and allowed the hand that was pressed against her chest to drift downwards to her wanting pussy. I teased her opening, rubbing my palm over her vulva causing her hind legs to kick involuntarily, and she squeeze my hand between her thighs.
She pushed me away from kiss, heavily panting and a goofy smile now plastered on her face, with an intense blush covering her muzzle now as well. She darted her eyes from side to side, making sure nopony was around watching us. I looked around as well, and when we noticed nopony for miles, she grabbed my face and shoved her tongue back down my throat which I meet with the same level of enthusiasm. I then slipped two of my fingers inside of her all the way to the knuckles, forcefully. She gasped while our lips were still connected, which allowed me to fully seize control of the kiss. She quickly melted into my touch with a hungry growl as I continued to jam my fingers forcefully into her needy pussy, making her thrash and squirm as she silently begged for more. She had now completely given up on fighting my tongue and just allowed me to work my magic. I started doing a ‘come hither’ motion inside of her, which made her moan like a whore.
“Ahh, fucking hell dude,” Zipp groaned as she forced me away from the kiss. “you’re driving me crazy with those fingers.”
She then hugs my neck and groaned into my ear. “I need you inside me.”
“Not yet.” I replied.
I then pushed her down to the ground so her face was level with my crotch. I then pulled out my cock, which was still a bit damp from my little romp with Sunny. She looked at it while biting her lip, and leaned in closer to get a taste. But I grabbed a clump of her hair in my fist and pushed her back against the wall.
“I said, not yet.” I growled, enjoying this a lot more than I thought I was going to.
I then grabbed my cock and slapped it against her face. I could tell it excited her, her eyes narrowed in on my dick as It was wapped against her face. Every time she tried to lick or suck my cock, I would push her face back or slap her hoof away.
“I need it, Anon. Please.” Zipp begged.
“Need what?” I asked rhetorically.
“C-come on dude, I already-.” Zipp was cut short by me slapping her across the face. I hit her a bit harder than I wanted, but she didn’t seem to mind. She shuttered and moaned, and judging from her reaction, i think the little whore even had a mini orgasm from being slapped.
“Beg.” I demanded.
“Come on dude, give it to me.” Zipp wined.
“That was lousy. I want you. To beg .” I demanded.
“Ughh, I need your fucking dick, dude! I want you to gag me with that thick cock of yours. I want you to make me never want to go back to stallions. Use me, fuck my face like a tool for your pleasure. Treat me like shit, and fuck my throat until tears are streaming down my face!”
I smirked at her lustful confession, and then grabbed her cheeks and forced her mouth open.
“Good girl.” I said before forcing my member into her open maw.
She gagged on my prick and she instinctively pushed back against my hips as my cock was pushed into the back of her throat. Eventually she switched up her attitude and closed her eyes and began to focus on taming her gag reflex to better choke down my cock. But she said she wanted me to use her , and I intended on doing just that. I forcibly repositioned her head to fuck her throat more efficiently, making her eyes shoot open in shock as my cock was rammed down her esophagus. Her hind hoofs kicked as I hit the back of her throat, and she gagged loudly as her air flow was restricted. I then pulled out of her mouth completely and allowed her to breathe for a second, because I didn’t intend on having her come back up for air for a while. She panted as saliva still connected my prick to her lips, I then put both my thumbs into her mouth and stretched her cheeks open as her tongue lolled out of her mouth before shoving my entire length back down her throat. A slight look of fear was visible in her eyes as she gagged and coughed and choked, and one of her hoofs pushed against my leg as tears began to roll down her face. Her face began to go red from having her oxygen supply withheld from her, and I held it in there for just a little bit longer, enjoying the tightness of her throat. The more she coughed and struggled for air it flexed her throat muscles, which made me want to keep it there forever. I kept my dick firmly burred in her throat until her eyes started to cross, and her face was almost purple from her lack of oxygen. I then pulled out suddenly, allowing her to cough as thick strands of saliva snapped from my member and dripped down Zipp’s chin.
“Oh… My… oh my gosh.” She said through gasps. “That was fucking awesome.”
“We’re not done yet.” I said.
I then bent down and picked her up, and pinned her chest against the wall. She looked back at me and bit her lip, and was giving me bedroom eyes. We both worked together to align or hips up with one another’s. I grabbed her hips and held them up while she placed both hoofs on the wall and looked back at me lustfully. Her wing fluttered to keep her body steady for me, but with how excited she was it was difficult for her to stay still. Her pussy winked in anticipation, she wanted me to plunge my length deep inside her, as fast and hard as I could. It glistened with arousal and every time it winked, more of her juices would pour out. A small part of me wanted to make her beg for it again, but I didn’t want to do that. I wanted this about as much as Zipp did at this point. I lined the tip of my prick up to the needy folds of her cunt, and without warning her I hammered my entire cock inside of her. She screamed in shock and delight, as I let her writhe on my cock as I kept it buried inside her.
“Ahh, holy. F-f-fuuu- “ she whimpered. “By the gods above, your cock feels amazing… how did Sunny keep it down with you slamming this, giant, throbbing cock inside of her.”
“She could take a dick, that’s for sure” I then leaned into her ear. “Now let’s see if a slut like you can handle it too.”
The hand I have placed on her chest felt her heart rate quicken at what I said. She bit her lip and was about to say something back to me, but I grabbed her head and push it into the wall before she could. She flinched when I did this but considered the twitching her inner walls made in response to that push told me she loved it. I then took my other hand and grabbed her back left hoof and raised it up above her head. I then began to pull out, and her body protested as my member began to exit her love tunnel, but when I got to the tip I slammed back inside her, making her yelp. I definitely hurt her with that thrust, but she did say she wanted me to hurt her, so it was a good thing. I also planned on ramming into her a lot harder than that, so she better get used to it. I began to slam into her, harder and harder which elicited a series of grunts and whimpers that were both a mixture of pleasure and pain from her.
“You like that don’t you, you fucking whore.” I growled as a slammed into her more.
“Agh, y-yess! Fuck me, holy s-s-shit! I love it! F-Fuck me up, please!” Her voice shaking with adrenaline. “Please! Hurt me more!”
I smirked at her and then rammed into her like a bull. She winced as her stiff, outstretched wings began to quiver. Her moans ranged from ones of pleasure, to ones of pain. But a majority of her moans were a mixture of those two feelings. I grunted as I continued to pound into her with all my strength, and I was hitting her so hard that I was sure I was gonna break something.
“AHH ! FUCK ! RUIN ME !”
Doesn’t seem like she’d mind something breaking to be honest.
I felt her walls beginning to convulse, I knew she was close now and I was not far behind. I gripped her head tighter and slammed into her so hard it scrunched her body up like an accordion. Her tongue lolled out of her mouth once again and her eyes drifted to the back of her skull as a gave her a few final thrusts inside her.
Each time I slammed into her both our climax’s inched closer to a release, until finally she let out a shrill shriek while her body shuttered in delight. Her hind legs kicked and bucked as she rode the high of her climax, and I continue to hold on tightly to her leg as it thrashed in my grip. When I felt my own climax begin to inch closer to its release, I released my grip on her hind leg. I then forcefully grabbed her shoulders as I smushed her body against the wall, pressing into her with the entire weight of my body. She yelped for a moment as I slammed into her, she let an out a few more shrieking moans before I eventually exploded inside of her. I held myself deep inside of her as I pumped my seed in her abused cunt. I then got a bit lost in the heat of the moment and bit her ear and pulled on one of her wings, both actions being harder than I meant them to be. She loved it however, as she cooed and melted against my chest as a let out the last of my load into her womb.
Once I had finished pumping every last drop into her, I pulled out of her and pushed her to the ground like a discarded piece of trash. She collapsed to the ground like a dead body. Her breathing was labored, and her eyes were crossed, and her hind legs were trembling uncontrollably. It looked like I literally fucked her brains out. I leaned against the opposite wall to catch my breath, eventually sliding down it and sitting on the ground while Zipp lay on the other side of the alleyway, my seed barley dripping out of her because of how deep I finished inside of her. I reached down to my ankles and began getting dressed, sliding my pants up my legs and zipping myself up as Zipp attempted to recover. As I was tightening my belt, I looked over at Zipp who was still in the same position, barely moving. I was about to get worried for her wellbeing when she finally spoke.
“Holy f-fuck.” She stuttered. “That was- the BEST sex- I’ve ever had.” Zipp said through heavy panting.
“Same here.” I said. “Probably the best pussy I’ve had in a while.” I complemented.
“Better than Sunny?” She said as she rotated her head to look at me.
“Let’s not make it a competition, alright.” I said.
“I-I wasn’t, I was just asking.” Zipp said defensively.
“I know.” I said. “But listen, you and me. Nothing changes between us, okay? Same with Sunny. We are still friends and only friends, I don’t want anything to change between us.”
“Alright, I’m cool with that.” Zipp said.
“Although,” I said with a finger raised. “If you wanted to fuck like that again. I wouldn’t be opposed.”
Once I said that, a sly smile creeped across her face.
“Alright so,” I said as I clapped my hands together.
“Yep.” She said, her hoofs shaking and trembling from the beating she took. “I’ll uhh, I'll see you later.”
She said with a wave, but she quickly lost her balance without all four hoofs placed on the ground. She attempted to place her hoof out to catch herself before she fell, but wasn’t successful. She collapsed to the ground with a thud, making me laugh at her expense. She blushed and laughed in embarrassment as she shakily rose to her hoofs again.
“That was your fault, ya’know.” She said with small giggle.
“Something tells me you like that fact.” I said, remembering all the things she said in the heat of the moment earlier.
“Hehe, yeah.” She said with another blush. “Thanks, by the way. That was really fun.”
“You're welcome. Slut .” I teased.
She laughed as she attempted to walk out of the ally, wobbling from side to side as she did. So she stuck close to the wall to make sure she didn’t fall to the ground again. I stared at her rump as it walked away and noticed it was turning pink from all the slapping and abuse it endured. With her white coat, this discoloration of her flank was easily noticeable. Hopefully nopony stares for too long, if somepony saw Princess Zephyrina Storm in that state it could lead to some kind of royal scandal. I scoffed thinking of the headlines now.Princess Zipp’s slutty secret revealed! ’ Ponies could be so nosy sometimes.
I waited for Zipp to be out of sight before I got up and left in the opposite direction. I headed for the main street of maretime bay and headed towards… uhh… I have no clue. I completely forgot what I was doing today. I guess fucking two of your best friends back-to-back will do that to you. Well, I figured walking in a random direction will jog my memory on what I was doing today.
Anon has sex with the mane 5
As I walked around town trying to jog my memory on what I was doing, I coincidentally passed by Sunny’s smoothie stand again, it was busier now than when I was there earlier. I watched her give somepony a smoothie and wave goodbye to them, she then spotted me out of the corner of her eye and waved to me as well. I winked back at her which caused her to smile and blush a bit in response. In that moment I felt like I was forgetting something, but I didn’t know what it could be.
“Hi-a Anon!” Izzy said as she appeared by my side. She startled me, but not as much as Zipp did earlier.
“Hey Izzy. What’s up?” I said.
“Ohhh nothing.” She said with an infectious smile. “I was just going to hang out at this super secret spot on the beach. Wanna come?”
Hehe. Come . If only she knew how funny that was. But I thought about her offer, I didn’t have anything else to do today, so why the hell not. I could use this break in the action from fucking our friends anyway. Plus, I enjoyed Izzy’s company so why not.
“Sure, besides I forgot what I was doing today anyways.” I shrugged.
“Good! That means your schedule is wiiiiide open!” Izzy said while using her magic to grab my arm and drag me with her to the beach.
She began skipping to her destination so I had to keep up a light jog to keep up with her. I took the opportunity to be a little bit of a pervert and took a peek at her plump flank as it gave a slight jiggle with every stride she made. I couldn’t help it really, I’m fresh off the heels of fucking two of our friends, I’m still a bit horny. Doesn’t help that it’s a nice view too. It’s the biggest ass out of our friends that’s for sure, and I guarantee it’s the softest out of them too. She then broke my perverted train of thought by taking a sharp turn and leading me down the stairs to the beach and then taking a sharp U-turn at the base of the stairs as she led me down an unpopulated path down the back of the beach.
“Come on, it’s this way!” Izzy beamed.
“Alright, alright.” I laughed. “It’s not like I can go anywhere with your magic on my hand.”
“Oh yeah.” She said with a giggle and a snort.
“What even is this secret spot anyways?” I asked.
“Oh it’s this spot I like to go to get some alone time. ” she said.
“You enjoy alone time?” I said teasingly.
“I know, I know.” She said with a wave of her hoof. “It’s must be a bit ironic coming from the pony that’s always up in other ponies businesses and talking their ears off, but I do value some time to myself every now and again.”
“Then why drag me along to your ‘alone time’ spot?” I asked.
“Cause I like ya.” Izzy said matter-of-factly.
“Is that it? Cause that’s not new information.”
“Does it have to be new information to be true?” She said rhetorically.
“Guess you got a point.”
“Yes I do. Also we’re here!” Izzy exclaimed with a singsong voice.
The spot wasn’t much to right home about, it was just a small area of the beach tucked away in a concrete arch that was part of the design of the wall. But she definitely marked her spot with all the paint, glitter, and various other decorations strewn about. The walls arch pattern creates a large enough divot in the wall that it could easily fit at least four ponies in it comfortably. There was also lots of shrubbery surrounding it on both ends, and even though the wall was at the edge of Maretime bay’s Main Street, there wasn’t a pony in sight. I could definitely see how this would be a place to get away from everypony for a few hours.
“Nice spot. How’d you come across it?” I asked.
“I was trotting along this side of the beach one day and stumbled on it. So I decided to claim it as my own since nopony else had.” She explained as she walked into the little alcove.
I shrugged and walked into the pony-made cave with her. I sat next to her and we just kinda, sat there for a while. Just enjoying the silence between us, and the crashing of the nearby waves. A cool peaceful breeze blew by and Izzy sighed as she closed her eyes, as if she was releasing a ton of stress all at once. I followed her lead and sighed as well, and leaned back until I was lying on my back and closed my eyes, enjoying this moment of peace.
“After the day I’ve had today Izzy, this is just what I needed.” I said as I crossed my legs over one another.
“Stressful?” She asked.
“Na, it was just kinda crazy, and tiring.” I said.
“Were you exercising?”
“…What?”
“Were you exercising?” She repeated, with almost the exact same cadence to her voice.
“…no… why would you think that?” I asked.
“Cause you were all sweaty when I saw ya.”
“Oh. Yeah, that’s… That’s not why I was sweaty.” I said awkwardly.
“Then what was the reason?” She said as she turned to face me.
“You sure you wanna know?” I said, opening my eyes to look at her.
“It’s not bad is it?” Izzy said a little worried. “Like the time you accidentally offended Sugar Moonlight while attempting to flirt with her?”
“No, no. Nothing like that.” I assured.
To give a little context here, I tried flirting with Sugar Moonlight by calling her a “cute horse,” and she took it as an insult and got really offended by that. Because apparently not every word from earth means the same thing here in Equestria. Izzy stepped in and apologized for me, I would’ve apologized myself but Izzy insisted she could word it better than I could. She was right, and thanks to her me and Sugar are still good friends to this day.
“Good,” she replied. “Was Not looking forward to having to patch up another friendship.”
“You didn’t have to do that by the way,” I said. “I was the asshole that screwed that up. I should’ve been the one to fix it.”
“Yeah. But, I thought my approach would’ve been better, and it wasss .” She said with another singsong voice.
“I guess so, yeah.” I smirked. “Thanks for that again by the way, times like those is what makes me appreciate having you in my life.”
“Aww, now you’re just being sappy.” Izzy said, waving her hoof.
“I mean it, you’re my closest friend here in Equestria.” I said, rolling over to my side so I wasn’t craning my neck to look at Izzy. “Out of all our friends, I spend the most time with you. I wouldn’t trade those moments for the world.”
“Aww, thank you.” Izzy said with a hoof over her heart. “Anyway, back on track. What happened to you today.”
“Oh yeah, well.” I paused trying to formulate my sentence correctly. “I went to Sunny’s smoothie stand earlier today and while we were talking and I, uhh… Well you remember what I said about how human have sex. Right?”
“Yeah, you guys don’t have heat cycles. So you can get down and dirty whenever you want.” Izzy said. “Sounds like a real inconvenience to me.” She loudly whispered, obviously not trying to hide what she said from me.
“Oh really?” I said; feigned offensive. “And heat cycles don’t sound inconvenient? Being horny so much it hurts, and it goes on for a week straight!? Hell no, I’ll take random boners over a perpetual hard on any day.”
Izzy giggled at my statement. “But, what does being horny have to do with- OHHHH.” She said in realization.
“Yeah… I didn’t go to her stand with the intention of having sex with her mind you, but one thing led to another and well, I think you know what happened after that.“
“How did you do it?” Izzy said, curious to know what happened next.
“Sunny closed up shop for a moment, and we did it inside her cart.” I said with a little smile.
“oooh, risky. did you get caught?”
“Posey almost did, and when we were done I found out somepony actually did end up catching us. Or caught me to be more specific.”
“Who!?” She said, wanting to know all the juicy details now.
“It was Zipp, she knew we were fuckin in there.” I said with a shrug.
“Was she jealous? Because I’m pretty sure she’s wanted to rut you for a while now.” Izzy said.
“I know.” I said letting that sit for a moment to let Izzy figure it out herself.
She looked at me inquisitively for a moment, then her eyes widened and gasped as put the pieces together. “Oh my gosh! Did You had sex with Zipp too!”
“Yep. THAT took a lot out of me. She wanted me to be rough, and boy was I. So if you see her walking funny today, I’m the reason why.” I said with a smile.
“So I guess, little Anon needed this relaxation time as well, huh?” She said pointing to my junk. A little too closely may I add.
“Oh yeah, he sure does.” I said as I shifted my weight to get comfortable again.
There was a period of silence before Izzy broke it with another question. “Did… did you, eat out any of them?”
“Na, there was no time to do something like that with Sunny, and you can’t really lick pussy aggressively without looking stupid.”
Another period of silence… Was she about to-?
“W-… would you… Like to?” Izzy said nervously.
No fucking way, what is happening today? Three of my friends in a row? This is getting kinda ridiculous now, I actually can’t believe this is happening. Is this all one big coincidence, or did they plan this? No no no, they couldn’t have. It’s gotta be a coincidence, and a pretty big one at that. But why was Izzy being so bold all of a sudden? Zipp I can understand, but her?
“Izzy. Are you sure you want to do this?” I asked. “I don’t want to make you feel like you’re being pressured to do anything with me.”
“No-no-no, I-I mean yes. I want to do it.” Izzy frantically reassured. “Besides i- Well… I have thought about doing it with you a few times. Especially when I’m in heat… you are the first person that pops into my head.” She blushed.
That was a very flattering thing for her to say. This is also kinda the most vulnerable Izzy has ever been with me. There has been other times she’s been serious with me, but this feels a bit different. Honestly I couldn’t turn her down even if I wanted to. She was my best friend after all, the nicest, cutest, funniest, and most caring pony I’ve ever met. She has helped me through a lot since a got here, whether that be patching up friendships for me, or just simply being there to talk to. I honestly couldn’t ask for a better friend.
Plus I would be lying to myself if I said she didn’t also pop into my head while I’ve been painting the flag pole.
“Okay, let’s do this.” I said. “I think I got one more round in me.”
“Really!” Izzy beamed.
“Yes, but let’s take it one step at a time.” I said pointing at my crotch. “He still needs a bit of a breather.”
“Yeah, got it.” Izzy said, a blush began to form. “Uhh, j-just stay right there.”
“Alright.” I laughed; curious about what she was planning to do.
She then walked over to me and crawled on top of me. Her face was now directly above mine, her breathing was shaky, and she bit her lip in anticipation. I swiped her long curly hair out of the way and looked at her cute, nervous face. I gently placed both my hands on her sides, and slowly slid my nails up and down her body from her waist to her shoulder. The sensation sent light shivers through her body, and she began to calm down a little, her nervous shaking becoming less intense. She continued to stare down at me, looking like she wanted to do something but was still too nervous to initiate it.
“Do you want to kiss me?” I asked.
She nodded in response.
“Come here then.”
I then passed a hand through her long, curly mane until my hand came to the back of her head and pulled her closer to me. Our lips collided and initially she was not a very good kisser, but she was a quick learner and followed my lead. There wasn’t any tongue, it wasn’t even that lustful for that matter. We were just tenderly kissing each other and after the kind of sex I had earlier, this kind of kiss was a welcomed change of pace. Izzy lowered herself and began to lay down on my chest, her hoofs resting around my neck and shoulders as she let out a blissful sigh while making out with me. I scratched her scalp lightly as we made out which made her moan a little bit more, and whenever I scratched the nape of her neck she would melt a little bit more into my touch. But what made her completely melt into my touch was when I began to scratch both her ears, which also made her let out a long, deep sigh. Izzy then separated from the kiss and looked down at me with a smile.
“You’re a great kisser.” Izzy said gleefully.
“So are you, don’t sell yourself short.” I complimented.
“Oh stop, I was just following your lead.” She said with a blush.
“My point still stands,” I said booping her nose. “You’re a great kisser, just like me.” I said that last part jokingly.
Izzy rolled her eyes with a smile and then dove back in for another kiss. I think she meant for it to be a short kiss, but I guess she just couldn’t help herself. As we kissed again I started to slide one of my hands down to her plump posterior, and gave it a light squeeze. She giggled in response, and her tail began wagging a little bit. I then grabbed a big chunk of her flank and spread her cheeks apart which made her giggle and arch her back to give me more access to her plump booty. I then slapped her cutie mark, not hard but just hard enough to shock her. She yelped and separated from the kiss as a result, and then giggled at her own reaction. I then began to kiss her neck while I gripped the base of her tail, lightly pulling on it. She hugged my head as I kissed her neck, and she let out the cutest little moans as I peppered her neck in smooches.
“Do you want to move on?” Izzy said with a hip wiggle.
“I’m cool with whatever. It’s your call.” I said.
She thought for a moment, then answered. “Just one more kiss.” She blushed.
“Alrigh-mmh.” I said, but she dove into yet another kiss before I could finish my thought.
I laughed at her eagerness, and wrapped my arms around her back. At this point, I had melted into her as much as she had melted into me, it was that good of a kiss. Her lips tasted like berries, and her soft, angelic lips were sending me into a sort of trance. Like I said, there wasn’t that much lustful feeling in this kiss, it felt more… romantic. It felt better than the kisses I shared with Sunny and Zipp. I couldn’t really pinpoint why it felt better, it just did. Maybe it was the fact the kiss was more tender than the others, or maybe it was because I liked being wanted in this more intimate way. Hell, maybe she’s just that good of a kisser.
We continue smooching until we both needed to separate for air. Both of us were lightly panted and gazed into each other eyes, and I couldn’t help but smile at the cute little blush on her face. I moved both my hands up from her back and began scratching the area right behind her jawbone. She smiled and her eyes fluttered shut as she leaned into my touch. She then let out a large sigh that seemed to release all her stress and anxiety all at once. She then stretched out her neck like a dog would when you scratch there favorite spot. I decided add to the sensation and began kissing her neck and chin, which she giggled in response to and hugged my head as I continued scratching and kissing her head and neck, her tail swishing from side to side as I continued to show her my affection.
“Did you do this to the others?” Izzy cooed.
“The scratching? I asked.
“Yeah .” She said with a sigh.
“No, you’re the lucky one.” I said.
“The others are missing out.” Izzy smiled.
I chuckled and kissed her collarbone, causing her to snuggle into me even more then she was before. She was adorable, and her mane and fur were so heavenly soft I almost forgot we were gearing up to have sex and not just kissing and snuggling. But she quickly reminded me of this fact with the next thing she said.
“I wanna move to the next level now.” Izzy said with a moan into my ear.
She then pushed away from the snuggling and looked down at me biting her lip, and then rotated herself around and presented her glistening pussy to me. Strands of hair from her tail clung to her already sopping wet cunt. My mouth began to water when her pink pony pussy winked at back at me, and I couldn’t wait to dig in. I grabbed her cheeks and spread her open with my thumbs, and gazed at her pink folds. Her velvety inner folds were so tantalizing and delicious looking, especially when she kept winking at me. She then began to rapidly lower her hips down to my face, and I eagerly anticipated the inevitable collision. When her lower lips finally connected to my mouth, I plunged my tongue inside her causing her to wiggle and moan at the sudden intrusion. She tasted incredibly sweet with a hint of tartness to her, but the delicious sweetness over powered the sharp aftertaste. It was most similarly tasting to a plum, and I was enjoying every last drop of her flavor.
I squeezed and spread her cheeks as I continued to plunge my tongue into her pink folds, causing her to moan loudly. She then began to rotate and swivel her hips on my face, causing herself to whimper as a result. As I lightly licked and kissed her pussy it eliciting the cutest little moans from her that encouraged me to continue. I was also making sure that when I pulled back for air that I let out hot and heavy breaths close to her clit, and judging from her moans she really enjoyed that. I then dove back in and gave a little suck to her clit, which caused her to involuntarily kick her hind leg. She let out a short moan as she began grinding on my face more vigorously and I felt her shifting her weight multiple time as she moaned. Her juices dripped down my face as I dug my tongue deeper into her snatch, and I began to dig my fingers into her inner thighs. She giggled and her hoofs instinctively slapped over my hands as my fingers tickled her. When I heard her giggles it made me want to tickle her more, so I continued to dig my fingers into her thighs while also pushing my tongue further inside her, making her give me the cutest mix of giggles and moans.
“Come on, make me cum! I’m so close already anon!” She moaned as she continued to grind on my face.
I then snaked my fingers further down her thighs, and began rubbing her clit just a little bit, making the muscles in her leg tense up and she began letting out a series of screams. She continued to squirm on top of me, her screams rising in intensity as she did. She then bent down and pushed my pants down my waist which caused my fully erect dick to spring out. I felt it boop Izzy on the nose, which made her giggle before she licked my cock from base to tip. Her soft and wet tongue sliding up my cock send a wave of pleasure up my spine. She then kissed the tip of my cock and licked my cock back down to the base. She never took my cock into her mouth for a full on blowjob, she just continued to lick and kiss my cock all over. She then sucked at the base of my cock which caused my dick twitched at the sensation and i moaned into her pussy, which caused Izzy to moan as well. Her hoof came around and began to stroke my shaft as she continue to lick my dick, which made me loose my focus on eating her out for a brief moment. Izzy then rocked her hips back into my face with an impatient groan, urging me to continue my tongue’s assault on her loins.
I scoffed at her reaction and resumed my action, while also giving her clit a slight pinch, causing her to scream in surprise but then growling in pleasure. She rocked her hips back harder and began grinding on my face more intensely, and tightening her thighs grip around my head. She had stopped licking my cock at this point, she was too busy focusing on the waves of pleasure I was sending through her body. Her legs began shaking and her inner walls began to tighten, letting me know she was close. She then let out a long shrill shriek, as a torrential downpour of her fluid blasted out of her cunt, and I eagerly drank up every drop I could, but a lot of it spilled down my chin and over my cheeks.
When her orgasm finally subsided, she let out a small whimper before she collapsed onto my chest. Her hot and heavy breath washing over my shaft, which made it throb a bit more. I lifted her hips off my face and plopped them down next to my head, the delicious aroma of her loins still lingering in my nostrils. She let out a long and heavy sigh as she slowly stroked my cock between her hoof and her face, her half lidded eyes staring back up at me.
“That was awesome.” She giggled.
“Glad you liked it.” I said in a sultry tone, while squeezing her rump which made her let out a small giggle.
“Thank you for doing that.” She said before planting a kiss at the base of my cock. “So… do you feel comfortable moving on ?” She said while she stroked my member.
“I think I do.” I said with a heavy exhale.
“You sure?” Izzy said. “I don’t want to make you feel pressured to do anything with me. Especially since you’ve already spent a lot of energy rutting two of our friends.”
“Izzy, you’re fine.” I said as I sat up and began scratching behind her ear reassuringly. “You aren’t pressuring me. Hell, I got your consent at the beginning of this because I thought I didn’t want you to feel pressured. So yeah, I wanna do this. You just might need to take the lead, that’s all.”
“Okay.” She said with a smile.
“And take it slow too.”
“Of course.” She said before climbing on top of me again.
She wiggled her butt on my cock until it slid in between her voluptuous cheeks. She then used her magic to clump up a bunch of sand behind me, which allowed me to sit up comfortably instead of laying down. She then placed both her hoofs on my shoulders and I placed my hands on her hips.
“Comfy?” She asked with an infectious smile.
“Yes, thank you.” I said.
She then leaned in and planted a small kiss on my lips, making an exaggerated “Mwah .” Sound.
She began to back her hips up and grinded her still sopping pussy on my cock. Her moist loins slid across my member, eliciting a moan from my throat. She smiled proudly after hearing me moan, and I could tell she wanted to make me moan again, so she raised her hip up and allowed my prick to poke at her entrance. She shuttered at the sensation and she lowered herself onto me, making me let out a deep sigh as I was slipped deeper inside of her. She let out a series of moans until she let out a euphoric sigh when she eventually bottomed out. She was tighter than the other girls, and her inner walls quivered intensely from being penetrated by my stiff prick. it almost felt like she was about to cum already, purely from having herself stuffed by my cock. Her hind legs shook, likely from a mix of adrenaline, lust, and from her previous intense orgasm not too long ago. She hooked her hoof around my neck and lifted her hips up slowly, before bringing them back down faster than before but still rather slowly. I slid my hands away from her rump and dug my fingers into her thighs, which caused them to instinctively flinch and made Izzy giggle in response.
“Hehehe, stop it Anon, that tickles!” Izzy said with a giggle and a snort.
“Didn’t seem to bother you before.” I said smugly, as I dug my thumbs into the crevice of her inner thighs.
“Yeah, b-b-but I… I… EEAHHH!”
Holy shit. I just triggered another orgasm. Was it really that easy to make you cum? Or was she just that into me?
Her fluids soaking my pelvis, as her horn also sputtered and shot out a few small harmless flares of magic. She attempted to keep her head up, but it eventually came crashing down into my shoulder as her second orgasm subsided.
“Wow. Already?” I said as I scratched her back while I hugged her.
“Y-yeah.” She said with small laugh.fucking good.” She said in a breathy tone.
I smiled at that compliment, and planted a kiss near the base of her horn.
“Can you continue?” I asked.
“N-no. Sorry, my legs are so weak I-“
“Don’t apologize to me.” I said while rubbing her back. “I’m not mad, not even a little bit.” I then began to slowly fuck her, eliciting small sultry moans from her.
“I wanted to give you a rest Anon.” Izzy said. “Ahh , I wanted you to lay back and relax while I fucked you .” She said, a tinge of sadness lingering in her voice.
“Izzy, it’s okay.” I said as I gently pet her mane. “I appreciate your efforts. But please, let me make you feel special.”
“Okay.” She said with a smile as she snuggled into my neck.
I grabbed her cutiemarks to stabilize her flank as I began to pump my member into her, slowly and methodically. Her velvety inner walls gripped my cock and forced more moans from my lips. Izzy’s tail flicked from side to side as I pumped into her, getting faster ever so slightly with every other thrust. She let out a blissful sigh and planted a series of kisses on my jaw as I continued to fuck her. I hugged her close and took a deep breath in, sniffing her mane. It smelled pleasantly sour almost like fermented berries, only it was a little sweeter then that. I couldn’t get enough of it, so I pulled her in closer and continued to sniff her soft, fuzzy mane. One of my hands drifted up from her flank and I ran my fingers through her mane, causing her to moan slightly as my fingernails scratched her scalp.
“ohhh yeah.” she cooed under her breath.
I hooked my arms around her in a tight hug, and she did the same with her hoofs around my neck. With her chest pressed firmly against my own, I could feel her heart beating pretty fast.
“You okay over there.” I asked.
She responded with a quiet “mm hmm. ”
I could tell from that nearly non-verbal response she was focusing on working towards her third climax. I decided to speed my pace up just a little bit, and judging by the small moans that squeaked out of Izzy’s mouth, she definitely approved of it. Her hind legs began slowly kicking, and her moans began getting louder and louder as she inched closer to her release. My own orgasm wasn’t nearly ready to go just yet, so Izzy was definitely going to cum way before me.
“Can you go faster, please?” She whimpered.
She’s lucky I still had enough energy to do just that. I was now going at a moderate pace which caused her breathing to become hot and heavy, and her grip around my neck tightened. I planted a kiss at the base of her horn again, and I saw a small smile creep across her face when I did that. I then took my fingers nail and quickly trailed it up her horn, creating distinct clicking noises as my nail raced over the grooves of her horn, this sensation made her let out a short whimper, and I just know it send a shiver down her spine. She bit her lip and peered up at me, so I scraped my nail up her horn again and pinched the tip of horn this time. This small action caused her to let out another whimper and all four of her legs to tensed up in response. It seems like she’s enjoying this hornplay, so I decided to tease and play with this new toy by planting a series of licks and kisses on it. The more I did this the more she moaned, and when I kissed her horn my teeth accidentally scraped her horn a bit. But I liked the reaction she gave me. I held her head still while I came in from the side and kissed it, then clenching my teeth down on it as I bit it. That sent her over the edge and I felt her cum once more and I kept my teeth clenched on her horn as she rode out her third orgasm, which was the most intense one by far.
Once she was done, she fell completely slack, her breathing was still fast and heavy though. I then flipped her over so that I was now on top staring down at her, and she looked up at me with a shocked expression. Her hind legs were in a spread eagle position twitching intently from her past orgasms, and her front hoofs were curled up cutely against her chest. I then resumed the rhythmic pumping of my cock into her quivering pussy, causing Izzy to moan weakly as she lost herself in an overwhelming sea of pleasure. I bent down and planted a kiss on the end of her snout, causing her to giggle. She then hooked her hoofs around my neck and stared up at me with those cute, magenta orbs, and pulled me into yet another embrace. I then pumped into her a bit harder then before, causing her to break the kiss as she moaned.
I felt the pressure in my loins growing, and as I continued to stare into Izzy’s eyes and admire her adorable features the closer my climax reached its precipice. I stopped for a brief moment to reposition my legs before I continued, faster this time. Every time my hips collided with hers it pushed another moan out of her throat, creating a start-stop kind of moaning pattern. I brushed both my hands through her hair and began to scratch her scalp, which caused her eyes to drift back into her skull.
“Ohhhh yeahhhh .” She blissfully moaned. “B-bit my horn again.” She said with a hushed tone, almost embarrassed to admit her desires.
I smirked and then obliged her request, but I just had to tease her a bit before I did it. I kissed the base of her horn, then dragging my tongue up the length of it. I then nibbled the tip of her horn and caused to let out a small squeal and a light spurt of sparks to spit from her horn.
“Oh my g-gosh,” Izzy stuttered. “Keep going… I’m, I’m gonna… horn- spark- cum.”
She barely made any sense at this point, but I could use common sense to figure out what she’s trying to say. I’ve heard of a ‘horn-gasm ’ before, but I thought that was just a myth. Hell, even most ponies believe it’s a myth. But considering she's becoming incoherent from my assault on her horn, a horn-gasm is the only logical conclusion for why this is happening to her. Speaking of orgasms, my own climax was starting to become impossible to ignore. I continued the dual assault on her horn and pussy, but I teased her by withholding her from full on biting down on her horn. I only scraped my teeth across the groove of her horn, which she liked but I could tell she was getting a bit annoyed with the teasing at this point. So with one last lick up her horn, I then got a horizontal angle on her horn again and bit her horn once again, which caused more cute squeaks and squeals to emerge from her and her back legs to kick involuntarily. I then began to grind my teeth against her horn, which sent her over the edge pretty much instantaneously. The ensuing horn-gasm even caught Izzy off guard. She spewed harmless magical sparks out of her horn like a broken fire hydrant, her entire body clenched up as her horn-gasm surged pleasure through her entire body. Her pussy clench around my cock because of this and it sent me over the edge as well. With a groan, I slammed balls deep into her and released my hot fluids into her love tunnel, painting her inner walls in hot white seed. I honestly surprised myself because I didn’t think I had enough stamina to cum as much as I did.
Eventually both our orgasms subsided, and when I let go of Izzy’s horn she just sat there. Motionless. Her eyes were unfocused, and her body was rigid and stiff. If it wasn’t for the fact she was still breathing, I would’ve thought I killed her…
I didn’t, right? I didn’t fuck her to death did I?
In a slight panic a began slapping her face, each slap getting harder and harder. Thankfully one of the slaps made her soul return to her body with a gasp, as if she had been holding her breath in. Her eyes blinked rapidly before finally focusing on me again and pulled me into a hug, nuzzling into my neck and making a little exaggerated moan as she did.
“Sorry,” she said. “Didn’t mean to scare you.”
“What even happened?” I asked.
“I kinda blacked out there for a moment.” She chuckled.
“Is that something I should be worried about?” I asked.
“No, not at all. In fact, you should be proud of what you did.” She reassured.
“That’s… that’s crazy.” I said in disbelief.
“Crazy good.” Izzy said.
“Well, I’m glad you had fun.” I said, still in slight disbelief.
“Sure did. Thank you, Anon.” She said before planting a small kiss on my lips.
“With all the sweating we’re doing, it’s ironic to think we came here to relax together.” I said gesturing to the spot Izzy brought us to.
“We can still do that.” Izzy said.Anon junior would probably appreciate an actual rest for once today.”
“Yeah, he probably would.” I said with a chuckle.
I then separated from Izzy and then pulled my pants back up. Izzy then used her magic, shaky and weak as it was, and managed to pull my shirt off my body. Izzy clearly wanted to be as close to me as possible, and a shirt would have gotten in the way.
I laughed at her and then laid back down next to her and pulled her into my chest which she eagerly excepted and nuzzled under my chin. I hooked my arms around her back and let one of my hands drift up and scratch her scalp through her thick mane. She wrapped her own hoofs around my shoulders and let out a satisfied sigh as she melted into my body. I then rested my cheek against her mane as I hugged her a bit tighter, her mane was so soft and silky it began to infect me with an urge to close my eyes and drift off to sleep. Judging by the change in Izzy’s breathing, I think she had already fallen asleep. She was adorable because I swear, she had the faintest snore going on as she slept against my chest. I snuggled into her a bit more, and eventually the sandman would ferry me to realm of sleep as well.
Anon has sex with the mane 5
A beam of the afternoon sun’s light unfortunately woke me up from my nap. I yawned and then lightly scratched the back of Izzy’s neck, which made Izzy begin to stir awake as well. While she started to wake up, I looked out to the sun’s placement in the sky, and noticed it was a couple hours away from setting completely.
“Hmm, what time is it? ” Izzy said groggily as her eyes opened slightly.
“Around six, I think.” I guesstimated.
“dammit, I gotta go.” She said disappointed.
“Really? That sucks, I kinda wanted to snuggle a bit more” I said.
“Yeah, me too.” Izzy said as she nuzzled into me, not wanting to leave me.
“I guess we can snuggle later if you want.” I offered.
“Like, later tonight?” She asked.
“Umm, I already promised sunny I’d snuggle with her later.” I said. “You could ask Sunny if she wouldn’t mind you joining us.” I joked.
“Oh well that’s a coincidence, I’m heading over to Sunny’s now.” Izzy said.
“Really,” I said. “What you got planned with her?”
“We were just going to swap stories and study unicorn and earth pony cultural differences.” Izzy explained. “It’s something we’ve had planned for a while. I’m probably gonna ask if I can snuggle with you guys later tonight while I’m there.”
“Good luck with that.” I said giving her tight and brief hug. “I guess I’ll find out the outcome to that question in a few hours.”
“Hopefully she’s cool with it.” She said with a smile.
She then made her way out of her secret beach spot, flicking her tail and giving me a clear view of her loins before looking back at me with a seductive grin. I smirked and rolled my eyes sarcastically at her, making her giggle before she stepped out of view. I then got up and stretched my own body, letting out a loud groan as my back cracked. I then grabbed my shirt off the floor and shook the sand off of it, then used it to slap the sand off my back before putting it back on. I then wondered what I was going to do in the meantime before meeting up with Sunny later tonight. As I thought about how to fill this gap in my schedule I ran my hands through my hair, and I noticed it was greasy and felt a bit matted.
Who would’ve guessed fucking three ponies would work up such a sweat.
I could go home and wash my hair real quick, but that was bit of a walk, besides I knew a few ponies that were closer that could clean my hair better than I ever could.
The employees at Mane Melody, a salon combined with the karaoke stage. It was an interesting combination and was possible for it to get quite populated some days. There was only three employees, Rocky riff, Jazz hoofs, and the founder Pipp petals. Pipp tried to get a cutie mark in mane care before she found her true passion for singing, but she still found enjoyment in mane care. So when she wanted to open up a small scale business it was a no brainer to combine her two passions into one unique experience. The two additional employees were both uniquely talented for the duel nature of the job as well. Hopefully it’s not too late and I can drop by for a moment.
*~~*
I walk through the doors to Mane melody and notice it was completely dead, except for the three employees. Two of them were kinda scared of me, the only one to greet me with a smile was Pipp. The reaction of the other two ponies was actually one of the better reactions I got from a pony I’m not well acquainted with, usually they change the direction they’re walking or scream. But these two were just a little frightened.
“Uhh, s-sorry, we’re about to close sir.” Rocky said with a shaky voice.
“Oh no, it’s fine I got him.” Pipp said with a dismissive hoof.
“You sure?” Rocky asked.
“Yes rocky I’m sure.” Pipp said placing a reassuring hoof on his shoulder. “That’s Anon. You know, the ‘nice human I’m friends with .’”
Rocky’s eyes darted between me and Pipp before sighing. “I’m sorry, A-Anon .”
“Don’t apologize, I’ve gotten worse reactions before.” I said with a smile. I couldn’t be mad at him, he’s trying.
“Alright you two, get going. I’ll close up shop behind you.” Pipp said as she quite literally began to push them out.
“Okay, see ya.” Jazz hoofs said.
“See you tomorrow!” Rocky said, almost in unison with Jazz hoofs.
“See ya!” Pipp said with a hoof wave, before closing and locking the door.
“Was it busy?” I asked.
“Yeah, a lot of my newer maretime bay Pipp-squeaks decided to visit.” She said as she closed the curtains of the windows.
“Exiting, you could say.” I said slyly.
“Busy schedule?” Pipp inquired.
“Definitely.” I answered.
“Is it still busy?” Pipp asked.
“Not right now, but I got a thing planned with sunny later,” I said. “but I’m free for the moment so I wanted to get pampered before I have to be there.”
“Aww, so you’re not here to just talk and hang out with me.” Pipp said.
“Im sorry, I-“
“I’m just messing with you.” Pipp interrupted. “Don’t be so serious.” She teased.
“I know, but we don’t get a lot of time to just hang out together, one-on-one.” I said.
“Yeah you’re right, but I can always multitask.” Pipp said with a smile. “Now, what do you want done?”
“Just a quick wash.” I said.
“That’s it?” She asked.
That’s it.” I confirmed.
“Sounds great!” Pipp beamed and then lifting herself into the air with her wings and flew over to a chair with a shampoo bowl attached to it.
I walked over and sat down in the chair, but because of my tall stature my knees nearly bumped into the small shelf that was placed across from the chair. Pipp then turned on the sink and began to soak my air and rubbing her hoofs on my scalp, making sure she got every inch of my hair properly soaked.
“So, what did you get up to today?” Pipp asked.
“Well I just got done hanging out with Izzy down by the beach. So if you see sand in my hair, that’s why.” I said.
Pipp let out a little giggle before asking a follow up question. “What were you doing? Just relaxing?”
“Not at first, by I did end up taking a nap on the beach with Izzy. So that was pretty relaxing.” I said.
“Is that all you did today? Sleep on the beach?” Pipp said in a joking tone.
“Well I did hang out with your sister a bit before that.” I said. “We had a nice time. But enough about me, how’s your day been?”
“Ehh, nothing too crazy. Just kinda, mildly irritating.” Pipp said as she dropped down and tried to squeeze in between my legs and the shelf to retrieve some shampoo from it.
She then grabbed a bottle of shampoo and the began to wiggle her way back out from my legs and the shelf. In her effort she unintentionally had her head pass over my groin, her head lingering over my crotch for the briefest of moments. Odd.
“I couldn’t wait around forever, I had to open the store, so Zipp stayed behind to see if the stand would open up. But considering I haven’t seen her since, I’d assume it never opened back up.” Pipp continued as she began to rub the shampoo into my head.
“Sounds annoying.” I said bluntly.
“A bit.” Pipp said. “I love my fans, but they can be a bit… Much.” She then began to squeeze some of the shampoo onto my hair as she continued to talk.hang out at the beach with you.” She said with a giggle.
“Yeah, you would’ve liked it.” I said with a smirk.
“I bet.” She said seductively before giggling again.
…There’s no way she knows, right?
“You said you hung out with Zipp today right?” Pipp said.
“Yeah, it was a nice.” I said.
“Did she have a good time with you?” She said slyly.
“…what do you mean by that?” I asked.
“Oh nothing, stud.” She complimented as she continued to lather my hair in shampoo.
“What are thinking?” I asked incredulously.
“I’m thinking you did more than just hang out with our friends.” Pipp said.
“What makes you think that?” I asked genuinely curious as to how she found out.
She then leaned in close to my ear and whispered, “I can smell our friends all over you .”
“Oh…” I responded awkwardly.
“Especially Izzy. She’s a squirter, isn’t she!?” She teased as she flicked water on my face.
“hey, knock it off.” I said smiling at her light teasing.
“Okay okay, I will, but you gotta tell me how this happened. You banged half our friends, that’s gossip I wanna hear about.” Pipp said gleefully as she began to rinse the shampoo out of my hair.
“Well, it started with sunny. Long story short, one thing led to another and we ended up doing it right there in her stand.” I stated.
“No way, is that why her stand was closed!” Pipp said in disbelief.
“Yep. She was also real hard to keep up with.” I continued. “Like, I was expecting her to be awkward and not be that experienced in sex. But I was so wrong, I almost wasn’t able keep up with her at all.”
“Did you get caught?” Pipp asked.
“Almost got caught by Posey Bloom. But your slut of a sister was apparently eavesdropping like, the entire time.” I said.
“Oh was she?” Pipp said as she began to dry my hair out with a towel.
“Yeah, sunny teleported me into a nearby alley after we were done. Then Zipp showed up, and she came on to me, and we ended up fucking right there in the alley.”
“Oh my gosh,” she said in an exasperated tone. “You know ponies call ME the slut of the royal family, right?” Pipp said slightly annoyed.
“She also wanted it rough, and we ended up getting pretty loud.” I added.
“I’m surprised she hasn’t got caught doing that shit.” Pipp said.
“It's definitely not a well hidden secret by any stretch of the imagination, I bet if you see her later today she’s probably still walking funny.” I said with a laugh which she joined in on.
“That’s crazy though, you back to back fucked Sunny and Zipp and somehow didn’t get caught.” She said in astonishment as she began to style my damp hair how I like it.
“She had a spot that’s tucked away from the public.” I said. “Good thing too because there was no way we would’ve been able to hide three orgasms, and one horn-gasm.” I said with a bit of cocky tone.
“That’s so hot.” She said under her breath. “That’s must’ve taken a lot out of you.”
“You could say that again.” I said. “But I did take a nap with Izzy after, so it refueled a bit of energy.”
“Did you make the other girls feel good?” Pipp said as she gave my shoulders a slight squeeze.
“Sure did.” I said.
“That’s good… real good .” Pipp mumbled. “And… TA DA!” She exclaimed as she showed me my reflection in a small handheld mirror so I could see my freshly cleaned hair.
“Alright nice, thank you.” I said before reaching into my pocket. “How much to I owe you?”
“Put that away, it’s on the house.” Pipp said with a dismissive hoof.
“Oh come on, let me pay.” I insisted.
“No, after the day you’ve had you deserve a little reward.” Pipp said.
“Well… thanks. I appreciate that.” I said.
“A free hair washing wasn’t the reward, hot stuff.” She said with a husky voice into my ear. She then flew around to land on my lap gently, placing her hoofs around my neck.
“What are you doing?” I said, more in disbelief than actually confusion.
“Don’t act coy now.” Pipp said.
“Pipp, I-I don’t know if I can last another round.” I admitted.
“Then you don’t have to. Let me do something for you, okay.” She said planting a small kiss on my lips. “I don’t want you to exert any energy. Dont buck your hips, don’t move a muscle. Just sit back, relax, and let me do all the work.” She then reached down between us and pushed her hoof against my growing bulge.
My dick pushed against the fabric of my pant from that statement. She smirked as she felt my member push against her soft hoof. She then leaned forward and planted a kiss on my lips, it was a gentle kiss- oh, nevermind. She let out a quiet moan as she forced her tongue into my mouth, instantly deepening the kiss. She scraped her tongue over the surface of my teeth and gums, while also wrestling with my own tongue. I placed my hand on her shoulder as we kissed, and I felt her wings extend from arousal. We inevitably separated for air, but Pipp dove back in right away with even more tongue wrestling while she began to grind herself against me. Her already slick pussy rubbing my bulge made me groan in pleasure. She then licked the inside of my cheek and dragged her tongue from the inside of my mouth to the outside. She continued to lick all the way up my face before she planted a kiss on my eye, followed by more kisses on my eyebrow, forehead, bridge of my nose, cheekbone and pretty much everywhere else her lips could reach on my face.
“Nghh, you’re so fucking hot .” She muttered.
She continued to pepper my face with licks and kisses until her kisses ended up looping back around to my mouth, where we then proceeded to swirl our tongues around each others before she invaded my mouth with her tongue once again. She moaned into my mouth as we continued the wrestling match between our tongues, breathing through her nose so we didn’t have to separate from the embrace. The kiss got sloppier as it went on, a mixture of both our saliva dribbled down both our chins, and she even bit my lip a couple times. She eventually separated slowly, a strand of saliva still connecting us as we panted heavily.
“S-sorry…” Pipp said, breaking the saliva strand. “Go a bit carried away there.”
It was just then that I noticed her lipstick was a bit smudged.
“Did you just leave a bunch of lipstick marks all over me?” I laughed.
“Yeah.” She said as she began to laugh from embarrassment.
She then grabbed the small mirror from before and showed me my new make over. I couldn’t contain my laughter seeing what she had done to me, which caused Pipp to began laughing as well at utter state she left me in. Her glittery pink lipstick stained my face so much it made me look like a member of a glamrock version of the band Kiss, especially with the lipstick mark on my eye. Even though I found it funny, it was also kinda hot seeing all those smooch marks covering my face.
When the humor of the situation died down and our laughter subsided, my throbbing cock made itself known once again. The tent I pitched pushed against Pipps vulva, causing her breath to hitch in her throat slightly. She then bit her lip and swiveled her hips on my groin, forcing a heavy breath from my lungs. She then leaned in and planted a small kiss on my lips once again before moving downwards, kissing my chin and giving my neck a lick along side another kiss.
“You like the lipstick marks don’t you?” She said seductively.
“A little.” I said.
Pipp giggled at my response and then began to slide down my body until her face was level with the cloth prison that housed my cock. She pushed her face against my bulge, her snout scrunching up against my pelvis as she took in a big whiff of, not only my scent, but the rest of our friends scents as well. She let out a load sigh of ecstasy from the aroma of sex that radiated from my cock. She seemed to get off more to smell of our friends more then my own scent. When my cock throbbed underneath her snout she got really excited, and pushed her muzzle into my groin forcefully. The sensation of her muzzle being smushed into my groin caused my body to lurch forward and I grabbed the back of her head and pushed her into my bulge more. She let out a growl of pleasure and her wings suddenly extended from her back involuntarily, clearly from arousal. She then frantically grabbed the waist band of my pants and pulled them down to my ankles, peering up at my cock as it twitches in anticipation.
Pipp restrained herself from sucking my cock as soon as she saw it for the moment, cause she had to prepare a few things. She reached under her wing and pulled out lipstick and lipgloss while shooting me a seductive look as she popped off the cap to her pink lipstick and began to reapply it. She continued to glare up at me with half lidded eyes, smacking her lips together, making an audible popping noises as she did. She then pulled out the lipgloss and slowly applied it as she continued to sustain eye contact with me.
My cock twitched in anticipation, and Pipp broke the eye contact with me to peer down at my cock as it throbbed. She smirked at me, finding enjoyment in the fact that I wanted her to satisfy me. Because of this fact, she teased me by making the lipstick process as slow as possible.
Once she was finally done reapplying parts of her beauty she leaned in close to my cock, booping her nose against the tip of my cock. My cock twitch at the sensation which caused her to smirk once again before she licked the tip of my cock. She then swirled her tongue around my tip before she planted a small kiss on it. The kiss left a pink lipstick mark on my tip, and as she trailed down my shaft she planted more kisses down my member, leaving more pink marks along my length. When she reached my balls she popped them into her mouth and began sucking them with an insatiable vigor. Her soft hoof came around to stroke my shaft as she continued to suck my balls, creating an incredibly blissful feeling to strike through my body.
“Ahh , fuck.” I groaned through gritted teeth.
Pipp giggled when she heard me groan, and then began to suck around the base of my cock. She then dragged her tongue up the back of my cock, and licking the pre-cum off my tip and planting another kiss on it as well. She continued to tease me by licking up my cock from base to tip, planting a decent amount of kisses along my length as she did. She then dragged her tongue from my balls all the way up and over the tip, and licked down the front side of my member down to pubic area in one long, unbroken motion. The more she teased me by licking and kissing my member, the more it made me want to shove my cock down her throat already. I guess she could sense my rising impatience because she finally took my tip into her mouth, still teased me a bit by swirling her tongue around my tip before doing so. She then proceeded with the blowjob she had been teasing me with for what felt like hours, and it was well worth the wait. She bobbed her head up and down, taking in a bit more of my length with every downward motion she made. Her lipstick would leave behind pink rings that marked her progress as she inched her way down my shaft.
“Fuck , you’re good at this.” I groaned.
She smirked and then slipped my cock out of her maw with a slurp.
“Oh, Just wait.” She said seductively before wrapping her hoofs around the base of my cock to stabilize it before she slammed her face back down, nearly swallowing my cock whole.
I gritted my teeth and my toes curled up and I groaned as I felt my cock nearly slide down the back of her soft throat. This was by far the best blowjob I’ve ever received, no doubt about it. The way she gripped my cock with her hoofs, and the warm wet feeling of her mouth as it bobbed up and down my cock exited me to no end. This blowjob was pornstar level, it was incredible. Her speed began to pick up and my dick hit the back of her throat a bit harder than she could handle, so she gagged lightly before pulling back from my cock to catch her breath.
“Goddamn, you’re really good at this.” I said with a heavy sigh.
“I think I can do better.” She said as she moved her hoofs off the base of my cock.
She then guided my cock into her maw once again, and she slid her tongue across the underside of my member as it inched closer to the back of her throat. She relaxed the muscles in her throat and slid my cock down her throat until her nose scrunched up against my pubic area. I groaned and cursed in pleasure as she stayed motionless with my entire length twitching inside her throat. She swiveled her head from side to side, causing my cock to rotate around her tight throat. She gagged as my cock twitched inside her throat, and her face began to turn red as her breathing was restricted. I couldn’t get enough of the tightness around my cock, and I grabbed the back of her head and kept her face smooshed against my pelvis, causing her to gag at the unexpected action. She coughed and gagged on my prick that was stuck down her throat and tears weld up in her eyes, making her mascara stream down her cheeks. She rapidly tapped my inner thighs with her hoof, and in response I released my grip on her head to allow her to pull back from my cock. Her head flew back as she took a deep breath in, followed by a series of coughing as strands of spit dribbled down her chin.
“Holy s-shit.” Pipp gasped. She then wiped at her cheeks and saw how I ruined her mascara. “Look what you did to me.” She said with a giggle.
“You should’ve seen your sister,” I said smugly. “She took my dick like a champ.”
“Fuck. i bet that slut loved being throat fucked by you.” She said as she began to rub her clit with a hoof.
“Clearly you did too.” I said as I pointed at the numerous lipstick marks on my cock.
“Yeah I did.” She said biting her lip as she continued to pleasure herself.
She then cupped my balls in her free hoof and then resumed sucking my cock. I let out a heavy sigh and then reached down a took off her tiara and placed it on the shelf behind her. I then ran my fingers through her hair and scratched her scalp as she sucked me off. She moaned on my cock, both from me scratching her, and from her own masterbation. I was already close to my fourth climax of the day by now, and the massage that Pipp was giving my ball was making that climax arrive even faster. She must've sensed the ride was coming to an end, so she tried to make it last just a little bit longer. She separated from my member and began licking the underside of my cock, over and over as her hot breath washed over my sopping wet prick.
She began to vigorously rub her lower lips, which caused her breathing to become more rapid and heavy. She pushed her nose into my balls and took in a big whiff while rubbing the length of cock against her face with her hoof. I saw her eyes flutter to the back of her skull as she took in my scent. She then stuck her tongue out and guided one of my balls into her mouth and began sucking on it as she began to stroke my cock a little faster.
“I want you to keep your dick stuck down my throat until I cum.” She muttered before popping my cock back into her maw.
She quickly worked her way back down to the base of my cock in just a few bobs of her head, gagging as my dick hit the back of her throat. My cock slide in and out of her esophagus and her expert gag reflex stopped her from choking on me. She continued to deepthroat my cock as she reached out her hoof to grab my hand and guided it to the back of her head again. I ran my fingers through her mane and scratching her scalp which caused her to groan in pleasure, sending vibrations through my cock. She then took my entire length into her throat, and I pushed her head down which, despite her gag reflex, caused her to choke and gag on my prick. She vigorously rubbed her clit while she gagged on the cock stuck in her throat, the pitch of her moans began to rise higher and higher as her climax reached a fever pitch; tears streaming down her face. Her wings suddenly shot out, stiff as concrete as her juices squirted out all over her hoof. Her throat squeezed my member as she coughed and gagged, forcing my own climax to reach a fever pitch.
“C-cumming.” I muttered.
Pipp batted my hand off her head in response and separated from my cock, which has now been completely covered in pink lipstick smudges. She coughed and sputtered as she gasped for air, she then opened up her mouth and her tongue flopping out lazily, dripping in saliva as she panted heavily while she jerked me off with both her hoofs. I moaned out loud as my cum shot out onto her face, three large initial spurts of my seed splattered on her face as I groaned loudly. As I continued to empty my load onto her face, one spurt of my seed nearly arched over her face but ultimately collided with her mane and one spurt overlapped her eye, forcing that eyes to shut. My spunk continued to erupt out of my cock, shooting across her tongue and all around her face, but would decrease in power with every spurt. Once she realizes my climax was finished, her stroking slowed down as well. She then closed her mouth and swallowed the hot sticky spunk that she was able to captured in her maw. She then opened up her mouth again to prove to me that she swallowed it all.
“Heh. And you called your sister a slut.” I joked.
“Well, I never denied I was one.” She chuckled. “I just try to keep my sluttiness behind close doors.” She then reached under her wing and pulled out her phone.
I laughed at the ridiculous ponyfication of the website Onlyfans before answering.
“Sure, I don’t care.” I with scoff.
She smiled and then began posing for the photos. Smiling wide and showing off her pearly white teeth, while also sticking her tongue out slightly through her teeth. She took a few photos like that before she switched angles, letting her tongue flop out of her mouth and made sure the camera could see to the back of her throat. Once she took a few more photos like that, she leaned over to me and handed me her phone.
“What do you think? Do They look good?” Pipp asked me with an optimistic smile.
She took about six photos of herself and I had to give it to her, she was a pretty good model. Even though I was already spent, the pictures of her with my seed painting her face and her mascara running down her cheeks, and the sight of the throat my cock was just shoved down moments ago made my cock tingle.
“I guess you like them, huh?” She giggled as she stared at my cock with a wiggle of her hips.
“Yeah, definitely.” I said. “Wanna go for round two?”
“Ohh, I would love to. But you gotta get going before you’re late, and I gotta redo all my make up.” Pipp said, waving her hoof to further emphasize her second statement.
“Well, hopefully we can do this again some other day.” I said.
“Of course.” Pipp said with a smile. “Sooo are you going to be gentlecolt and clean me off or what?”
I chuckled to myself before answering.
“Only if you clean me up as well.” I said as I gestured to all the lipstick marks that peppered my face.
“Deal.” Pipp said with smile.
She then flew over and grabbing the damp towel from earlier for herself, and then grabbed a makeup remover wipe from under her wing for me. She tossed the towel to me and then flew over and gently landed on my lap. We then began to clean each others faces up, and I made sure to get my seed out her hair first, I then cleaned off her eye so she could open both her eyes again. She ended up going through a few makeup wipes with me in order to get all her lipstick off me, mostly because the wipes were rather small.
We eventually finished cleaning each other up, but Pipp left my lips till last so she could plant one last kiss upon them. This time it was actually a gentle kiss, and once she separated she wiped my lips off and with that, we had finally finished cleaning each others faces.
“Catch you later, stud.” Pipp said while booping my nose with her own.
“See ya.” I said. “Hopefully we can go for round two next time we have some alone time.”
“Hopefully that day comes sooner rather than later.” Pipp said in a sultry tone.
“Well, I got an hour and forty five minutes till I have to be there. I’ll probably hang out with Hitch for a bit, I haven't seen him today.”
“Oh really now.” Pipp said seductively as she hopped off of me.
“Stop it,” I said, rolling my eyes and zipping myself up. “He’ll probably be the only pony I interact with today I don’t end up fucking.”
“Well now you’ve jinxed it.” Pipp giggled.
“You know what, I hope I did. Dont want to leave Hitch out of the fun.” I half joked.
“Well, you two have fun then.” Pipp said with a wave.
I smiled and rolled my eyes at Pipps comment, and then exited the building. Next stop, the sheriff’s office for a little guy time.
Anon has sex with the mane 5
“Hey Hitch.” I announced as I burst through the front door of the sheriff's office.
“Wha- oh hey Anon. What brings you here?” Hitch said.
“I just wanted to hang out for a bit before I have meet up with Sunny later.” I said as a pulled over a nearby chair and sat in it backwards.
“Well, I’m actually glad you decided to drop by. Today has been very, very boring.” Hitch said.
“No littering?” I said sarcastically.
“Yeah, no littering.” Hitch scoffed.
“So what have you been stuck doing all day? Paperwork?” I said, as I pointed at the stacks of paper on his desk.
“Yeah…” Hitch said with an eye roll. “Boring as shit.” He sighed.
“Damn… heh, I know I said it jokingly before, but with a boring day like this you almost wish for someone to litter just to break up the monotony.” I said.
“No kidding.” He said. “I did get one call earlier today though, but that didn’t lead to anything exciting.”
“What was it?”
“Some mare came in and told me she heard another mare screaming in an alleyway. By the time I got there, the screaming had already stopped and I couldn’t find the culprit. So it was back to paperwork for me. Yippee… ” Hitch said in sarcastic manner.
I couldn’t hold my smirk back because I’m pretty sure I was the reason some mare was screaming in that alleyway.
“None of the other girls came to visit you today?” I asked.
“Well, I saw Zipp while I was out searching for the screamer. But she seemed, I-i don’t know, drunk? So we didn’t talk for long.” Hitch said.
“Zipp was daytime drinking?” I said with smug ass smile on my face.
“I don’t think so, she didn’t talk or smell drunk. But she definitely walked like she was inebriated.” He said while he continued to scribble away at the papers in front of him.
“Well, I had a rather exciting day today.” I said.
“Exiting, huh?” Hitch said.
“Yeah, I had a domino effect of things happen to me today, it got kinda crazy.” I said.
“Please, tell me about it.” Hitch said, almost desperate to hear anything than the ambience of the sheriff’s office.
“You sure? It gets sexual pretty fast.” I warned.
“Sexual? Well now you’ve peaked my curiosity, Anon. You’ve got to tell me now.” Hitch said.
I then proceeded to inform Hitch about my erotic adventures throughout town. He was incredibly shocked to hear all of it, but he was also quite impressed. I even saw him blush a few times when discussing some of the spicier details. Once I was done, he even joined in and told me some of his own sex stories. Most of them were mares that just wanted to be worked over by the sexy sheriff of maretime bay though. The one sex story he shared that actually surprised me though was the fact that he dated Sunny for a bit, so he actually knew about the wild side Sunny has when sleeping with somepony.
So, way before I ever arrived in Equestria, and even before the three pony races reunited, those two earth ponies dated for about four years. Hitch then went on to say how when they had sex, she took control immediately, which threw him off his game since he was always used to being the dominant one, but he kinda liked it. We both laughed as we discussed our shared experience with Sunny, because both of us could barely keep up with her enthusiasm. Both of us weren’t expecting her to go from a cute little mare to suddenly become a sex freak with the flick of a switch.
As the conversation continued, I eluted to the fact that me and Zipp were the perpetrators of the screaming he tried to check out earlier today. Hitch laughed and cursed me out in response, and after I divulged what I was doing to her that made her scream, there was a massive blush on his face as well. He then expressed disbelief at how he didn’t catch us, and also laughed when he put the pieces together and realizing Zipp was walking funny because of me. When talking about my experience with Pipp he said I was lucky because of how pretty she was, which I jokingly responded by saying I actually wasn’t lucky because I didn’t actually fuck her like I did the other girls. Hitch’s response to that remark was to say my experience with Izzy should’ve made up for the lack of pussy from Pipp, mostly because I made her cum multiple times. He then lamented about never being able to make a mare to cum as often as Izzy did with me, the disappointed tone of his voice kinda made me feel bad for even bringing it up.
“Hey, you know I didn’t bring all this up to brag and make you feel bad right?.” I said.
“Yeah I know, it’s not that big a deal anyway.” Hitch said.
“Why’s that? You swing for the other team all of a sudden?” I joked.
“No, it’s nothing like that.” Hitch said with a light blush appearing in his muzzle.
“Right. Because you drooling over my abs when I’m working around town is you totally being straight, right?” I teased.
Hitch’s blush deepened as he stammered, frantically trying to come up with a believable excuse, but to no avail.
“Dude I’m fucking with you,” I said, laughing at his expense. “But even if you were gay, you should know by now that I wouldn’t judge you. You’re my friend Hitch, I would never end our bromance over something as petty as that.”
“Oh stop with that mushy shit.” Hitch said with an embarrassed smile.
“Don’t act like you didn’t appreciate it.” I said smugly.
Hitch rolled his eye.
“No problem, bro.” I said before getting up from my seat.
I then walked closer to Hitch and placed the chair down in front of him and sat in it backwards again as I looked my stallion friend in the eyes.
“Now, is there something you want to get off your chest about your sexuality, or was it actually nothing?”
He paused for a moment. “You promise me you won’t judge.” He said nervously.
“What did I just tell you earlier?” I asked rhetorically.
“Right, okay.”
“Oh god, I’m guessing that spiraled out of control quickly.” I said sarcastically.
“It actually didn’t end up leading to much, we were too drunk to do anything other then kiss each other.” Hitch said.
“That’s actually kinda surprising, considering how bold Sunny gets when she’s drunk.” I joked.
“Yeah,” Hitch laughed. “But anyways, we played spin the bottle and… every once in a while I would land on sprout, or sprout would land on me. The first time we kissed it was awkward, and weird. But the more we landed on each other, the more I ended up liking it. Hell, we both did, to the point that me and sprout were practically making out with each other by the end of the night.”
Hitch shifted in his seat awkwardly before he continued.
Hitch ended his story looking anywhere else but at my face. He was likely too embarrassed to look at me after basically admitting he had a little man crush on me. Even though I pretty much knew he was into me in some way before hand, it was incredibly flattering to actually hear it from the horse’s mouth. But I could tell he was feeling incredibly uncomfortable right now, likely worried with how I’m going to respond.
“That’s incredibly sweet of you to think of me that way Hitch, and really brave to admit it too. As I’m sure you know by now, I’m on a roll when it comes to rutting our friends today. So do you wanna be the fifth and final pony?” I said as I leaned in closer to him.
His blush grew immensely after I said that.
“Wha- haha, I uhh, well- I’m uhh,” he stammered awkwardly as he struggled to find the word to properly respond with.
“Hitch, we don’t have to do it. I’ve had enough sex today, trust me. But even if I'm tired, achy, and even a bit sore, I’m willing to dive back into the hay one more time. Just for you.” I then gently grabbed his chin and looked him in the eyes.
Hitch smiled and laughed as he pushed my hand away, but that goofy smile stayed plastered on his face. He then tapped the tips of his hoofs together awkwardly.
“You sure?” He asked.
“I’m positive Hitch.” I assured.
He thought for a moment, continuing to awkwardly tap his hoofs together. He looked down and away as he built up the courage to tell me what I already knew he wanted.
“Sure… let’s do it.” Hitch said timidly. “But, I-I’m new to this, obviously. So… please, take it easy.”
“Of course.” I responded.
I then got up and walked back to the door and locked it behind my back while staring back at Hitch. Hitch’s demeanor grew more nervous, likely because when he heard the click of that lock it dawned on him that this was really happening. When I walked back over to him, I got behind his desk I turned his swivel chair around so that he was facing me. He looked up at me nervously, but when I gently smiled down at him he smiled back, knowing he could trust me. I then leaned down close to his face, our noses practically touching. I could feel his hot, nervous breath wash over my lips in anticipation, and I could practically hear his heart beating out of his chest with how anxious he was.
“You ready?” I whispered just load enough for him to hear.
He simply nodded in response.
I closed in the gap slowly and gave him a few gentle pecks on the lips. I allowed Hitch to take the lead, and when he realized it was up to him to move the kiss along, he pressed his lips into mine and deepened the kiss. As we continued to make out he grabbed my shirt collar and pulled down on it, bringing me to my knees. When I knelt down to his eye level he threw himself onto me, making the kiss that much more passionate. His hoofs hooked under my arms and caressed my shoulders. I then wrapped one of my arms around his neck and resting my palm on his shoulder, my other arm wrapped around his back and scratched it gently. Hitch let out a long sigh as I scratched his back. He then squeezed his hoofs tighter around my body which pulled our bodies closer together into a tight hug. We then separated from the kiss and stared into each others eyes as we caught our breath.
“You good?” I asked, still noticing a tinge of nervousness in him.
“Y-yeah. I’m good.” Hitch said.
“You wanna move on, or you do want to keep kissing?”
“Uhh… l-let’s kiss again, please.” Hitch said nervously.
Without another word between us, our lips crashed into each others again in another long embrace, but as we continued making out I felt something fleshy begin to poke my chest. I separated from the kiss way too soon for Hitch’s liking, and when I looked at what poked me I was rather shocked with what I saw. I knew I was going to see Hitch’s dick poking me, but the length and thickness of it was quite impressive. He was much longer than me, but he didn’t dwarf my length by any means. It was maybe three and half inches longer than mine, but there was no debate that it was certainly way thicker than me.
“Nice cock.” I said in a blunt manner to try and illicit a laugh from Hitch.
Hitch let out a small chuckle and blushed in response.
“Oh stop with the apologies.” I blurted out. “We’re gonna fuck in a moment, don’t apologize for little trailblazer coming out to play a bit early.”
Hitch blushed and evaded eye contact.
I smirked and then began to drag my finger down his chest, slowly and methodically. When my finger passed by his heart, I felt it anxiously beating out of his chest. I stopped and peered up at him for a moment with concern in my expression, in response Hitch took a deep breath to quell his anxiety. He then nodded at me to continue my journey down to his nether region. I then began to trail my whole hand down his stomach, and halted my journey as I rested my hand right above his cock. I then moved behind him, placing a hand on his chest and resting my head next to his. I then resumed my hands journey, slowly wrapping my fingers around the base of his cock. I firmly grasped the base of his cock, causing it to pulse in excitement. I began to slowly stroke his shaft, making him let out a heavy moan as my hand glided up and down his shaft. His cock twitched in my palm and his breathing got heavier, he then closed his eyes and let his head come back to rest on my shoulder.
“Fuuuck dude. that feels so much better then hoofs.” He muttered.
I couldn’t help but smirk at that statement as I began stroking him a bit faster. He bit his lip and let out a small moan as my pace quickened, his hips rocking as the pressure built up within him. He squirmed in my grip and his moans got louder and more frequent as pre cum began to drip from the tip of his member. I began to caress his upper chest and his hoof grabbed my hand and his other hoof reached around to hook around my face as his breathing began to stutter. As i stroked him faster and faster, his eyes began to roll into the back of his head and he let out a short cry of pleasure.
“F-fuck ahh. A-anon, holy shit. I, I-I’m gonna cum.” Hitch grunted through hot and heavy breaths.
I repositioning my grip on his member slightly and began jerking him off even faster, faster than I have been before. Before I hade been stroking him at a semi-moderate pace, but now I was stroking him so fast it looked like I was desperate to see him cum. After a few homoerotic moans, his seed exploded from his cock. He grunted and gridded his teeth as rope after rope of his hot spunk splattered onto the floor. He even went crosseyed as his orgasm continued creating a puddle on the floor, and once his orgasm finally subsided he rested the back of his head against my shoulder.
“That was… wow. That was great.” Hitch said, obviously still riding the high of his orgasm.
“So… bottom or top?” I asked.
“Huh?”
“Did you want to be the bottom. Or the top?” I clarified.
“Uhh… well… hehe.” Hitch stammered.
I cupped his jaw and twisted his head around to look at me.
“B-… bottom.” he muttered quietly.
I smiled at him and rustled my hand through his hair and gave him another reassuring kiss, this time on the lips. I felt the tension in his body melt away as we kissed.
“You ready?” I asked, separating from the kiss.
“Yeah, I… just take it slow please.”
“Don’t worry, I’ll take it nice and slow. ”
“And you’ll be gentle?”
“I will, don’t worry.” I planted one last reassuring kiss on his lips then leaned over and whispered in his ear. “Now go bend over your desk for me.”
I ended that statement by giving a slight nibble to his ear, causing him to flinch and giggle from the sensation. His prick also began to stand at attention once again from that action. He then began to walk over to his desk, placing his front hoofs on the surface and looking back at himself with a look that conveyed he didn’t know what to do next.
“Am I doing this right?” He asked nervously.
“You’re doing fine,” I said as I grabbed his hips, causing him to gasp. “Let me just adjust a few things here.”
“Okay…” Hitch said sheepishly.
I then lifted up on his hips and pulled back on them until they came into contact with my bulge, which forced a small moan from his mouth. I then gently kicked both his hind hoofs apart so that they stood at a wide stance, his tail instinctively tucking in to cover his ponut. I then gently pushed on his lower back to force it into an arched position, feeling the perfect balance of a tight and muscular frame with a plump and soft posterior. His fur was also more coarse than the other mares as well but it wasn’t unpleasant, and as I continued to glide my hands over his fur I felt Him shift his weight anxiously.
“You alright?” I asked.
“Uh huh.” Hitch croaked.
I wasn’t really convinced by that answer, he was still pretty tense despite all the reassurance I’ve been giving him. I bent down and hugged him around the chest as I whispered in his ear.
He looked back at me and gave me a worried look. “No! I-I’m good, I want to do this!”
“Okay, that good, but we need to do A LOT of prep work before we go for it… okay?”
“Why?” He asked.
“You’re still Super tensed up. If we do this now with how tense you are, it’s going to hurt a lot.” I said while rubbing his flank.
“Alright.” He said with a large exhale to calm his nerves.
“I also need to be lubed up a bit, so…” I then leaned down to whisper into his ear again. “How does cleaning the lipstick of my cock sound?”
I could practically feel his heart jump into his throat, and I even felt the vibration through his skin from his dick twitching and slapping against his stomach. He then let out a nervous laugh before snuggling into my neck. He then rocked his hips back into my crotch, which I took as a positive affirmation to my previous question. I smiled and then gave him another kiss an his lips, and once we separated I pulled him off the desk and made him sit on the floor.
I began undoing my pants for the fifth time today, as hitch stared down my bulge in anticipation, waiting for my member to spring out. Once my cock was freed, Hitch’s eyes narrowed in on my cock and his own cock throbbing in excitement. He couldn’t help but crack a small, dorky smile as he inched closer to my cock and slipped the tip of my shaft into his mouth. He continued to slide my cock down his maw, which was when I quickly realized that he was very amateur. But it’s not like he was terrible, he had somewhat of an idea of what he was supposed to be doing, especially for a straight stallions first blowjob. But coming off the heels of the amazing, pornstar level blowjob Pipp gave me, this was very amateur.
He peered up at me as he bobbed his head on my member, I smiled down at him to make it known to him that he’s doing a good job. He then closed his eyes and began to stroke his own cock as he sucked me off. Finally he was beginning to loosen up, he even let out a moan which made me smile and run my fingers through his mane. He was making sure that his saliva coated my cock as much as possible as he continued to swallow as much of my cock as he could, which wasn’t much but at least he was making an effort.
He then separated from my cock and dove into my balls, licking and sucking them and making me moan out from the sensation. He then dragged his tongue back up my shaft before taking me back into his maw once again. I ran my fingers through his mane as he bobbed his head a few more times before he separated once again and stood back up. He then walked back over to the desk and got back into the arched position I had him in earlier. Spread legs, arched back, but now with a raised tail that exposes his goods to me, he even shook his hips a bit. He wasn’t feeling nervous anymore that’s for sure. The sight of his hindquarters being presented to me was incredibly alluring, the sight of his winking anus and his back sack made my mouth water. Not to mention that little smirk he was giving me made my heart pound in my chest. I don’t know what came over me, it was almost like I had a bit of a gay panic of some kind. Now that I think about it, a gay panic would explain why Hitch was stammering like a fool earlier.
“Didn’t you say you had somewhere to be later?” Hitch asked rhetorically while shaking his rump a bit. “Hurry up and stick it in.”
I chuckled at his forwardness, he had clearly gotten over his ‘gay panic’ that’s for sure. I also wasn’t about to make him wait any longer for what he craved for. I grabbed both his cheeks and spread them and I then poked and prodded at the entrance to his anus with the tip my member.
“This is gonna hurt a bit,” I warned. “But if you relax, it’ll hurt a lot less.” I said as prodded at his entrance.
“Okay,” Hitch said while looking back at me. “I trust you.” He said with a smile.
I smiled back at him and the grabbed my stiff prick and began to push my tip into his entrance. When the tip teased his entrance it instinctively tightened, but quickly relaxed as I continued to push into him. Hitch hissed as my tip finally entered him and he shifted the weight in his hind legs a bunch of times as I continued pushing deeper and deeper into him. When I made it half way in, most of the resistance his anus provided had dissipated, and once I had bottomed out he let out a satisfied moan. I kept myself hilted deep inside of him so hitch could get used to the feeling of me inside of him, and also because I fucking loved the feeling of his tight, warm, virgin anus hugging my cock. After a few moments, he let out a long sigh and rested his chin on his desk with a blissful look plastered on his face.
“Doing alright?” I asked.
“Hell yeah.” He said.
“How does it feel?” I said as I softly rubbed his abdomen.
“Weird.” He chuckled. “But, it’s a good weird.”
“Did it hurt?” I asked.
“It did at first.” He said.
“Does it still hurt?” I asked.
“Just a bit, but nothing unbearable.” He assured.
“Good.” I said as I patted his lower back. “Just tell me if you want me to go faster or slower. Okay?”
“Alright.” Hitch said with a smile.
I then began to pull out of him and when I slowly pushed back into him, it forced a moan that was a mix of pain and pleasure from the stallion. His moans were shallow and restrained, almost like he was trying to suppress it.
“You feeling okay?” I asked.
“Yep.” Hitch mumbled.
“Then prove it, and moan for me.” I said as I thrusted into him a little harder than he was expecting.
A short moan escaped his lips once i thrusted into him, a small blush forming from his own reaction. He took the hint and stopped trying to hide his enjoyment as he began to moan out load as the pain began to dissipate, and pleasure quickly replacing it.
“F-faster please.” He said timidly.
I gradually kicked up speed and began to move faster inside of him, his warm asshole hugging my cock as it glided through his ponut felt so good. Sure, a wet pussy felt heavenly, but a stallions asshole was something uniquely pleasant. His moans grew in volume at the same rate my cock increased in speed, my own moans spilling forth from my lips as out flesh slapped together. Hitch then began to push his hips back into my own, letting out a guttural moan as my cock hit deep inside of him.
“F-fuck, ahh.” He cursed under his breath. “Harder please.”
He’s really enjoying this now, considering he’s now moaning like a mare and was actually starting to drool from the pleasure. As I began to pick up the pace, he raised his chin up from his desk and looked back at me and smiled as he moaned. I then bent down until I was next to his ear, and hooked my arm around his neck and I don’t know what possessed me to say this, but I whispered-
“Who’s a good boy?”
“I am!” He answered with zero hesitation.
“You’re so fucking cute.” I said with a chuckle.
I then began to trail my hands downwards towards his nether region and gripped the base of his cock and began to stoke it in rhythm with my thrusts. His head reeled back in delight from the reach around I was giving him, and he nuzzled into my neck as he let out a series of moaned into my ear. I reached up with my free hand and began scratching his neck while planting a few kisses on his cheekbone and jawline. He smiled at the titillating sensations being sent throughout his body. As I continued this onslaught I felt Hitch’s back legs begin to tremble.
“F-fuck! Ah, holy shit! Harder! Deeper please! I’m so close!” He pleaded.
Good thing he’s close, because I’m not far behind now. I began to ram my cock harder into him as he requested, making sure I hit his prostate every time a jammed my prick into his tight anus. I also began stroking him faster as well, making him cry out in pleasure. He squirmed under my grip and rocked his hips back into my own, lowering his head and gritted his teeth as he braced for his release. Him rocking his hips back into mine was the straw that broke the camels back for me. Before I knew it, I was emptying my load into him, letting out a load grunt as i continued to slam into him as I unloaded my spunk deep inside of him. I also began jerking him off as fast as I possibly could, until he finally exploded as well. He let out a load, almost girlish moan as he reached a powerful orgasm, rope after rope of his seed painting the underside of his desk. I then hilted myself into his anus, striking his G-spot with all my might, this thrust had seemingly fucked even more cum from him. as we both let out spurt after spurt of our spunk for what felt like hours until we were both completely drained. We then both slowly collapsed to the floor in exhaustion, panting and sweating as we held each other and gazed into each other’s eyes.
“Holy s-shit.” Hitch said between pants.
“I’m assuming you enjoyed it?” I asked rhetorically, likely knowing the answer was going to be-
“Fuck yeah I did.”
“Good. I’m glad you liked your first time.”
“Are you kidding me? That was the best orgasm I’ve ever had! Of course I would’ve liked it.” Hitch said matter-of-factly.
“Again, I’m glad you had fun.” I said with a smile.
“I’m just glad I made the right call in trusting you to take care of me tonight.” Hitch said with a blush.
I rolled my eyes at his sappy comment before leaning in to plant another kiss on his lips. I then looked up at the clock and noticed the time.
“Sorry to cum and go but I do gotta go now. I still got those plans with sunny.” I said, really wishing I could spent a bit more time with the stallion I just rutted.
“Let me walk you there.” Hitch insisted.
“You don’t have to do that.” I said.
“Nope. I’ve walked home every mare I’ve ever rutted. Just because the rolls were reversed tonight doesn’t change that standard I’ve placed for myself. I’m walking you to Sunny’s place.” Hitch said as he rose to his hoofs.
“If you insist.” I said with a smile has I got dressed for the fifth and final time today.
At least I hope it’s the last time, I don’t know if I could go another round to be honest. It feels like if I do it with one more mare or stallion, they might just fuck the cock off my hips.
I Rose to my feet and Hitch followed suit, his hind legs still shaking a bit but was still able to walk straight, unlike Zipp who could barely walk, let alone stand after I was done with her. But anyways, back on track.firsts for Hitch, the answer was most likely the ladder.
“thanks for walking me all the way out here Hitch.” I said as we finally arrived at Sunny’s lighthouse.
“No problem bro.” Hitch said. “I’ll catch you later.”
“Don’t you wanna drop in real quick and say ‘hi’ to Sunny before you go?” I asked.
“Uhh, sure. Why not.” Hitch said with a shrug.
I knocked on the door, and it was answered very quickly. The pony that answered the door was not Sunny, instead it was Izzy.
“She said yes!” Izzy exclaimed excitedly.
“Wha?” I grunted.
“Sunny’s okay with me joining the snuggling!” Izzy elaborated; so ecstatic that she began prancing in place.
“Oh! That’s awesome!” I exclaimed. “Where is Sunny anyway?”
“Waiting for us on her bed! Come on!” Izzy said before grabbing my hand with her magic and pulling me into the house.
“Am I allowed to drop in real quick, or are you three going to be busy soon?” Hitch said, capturing Izzy’s attention.
“Oh. Hi Hitch! I didn’t see you there.” Izzy said before waving at Hitch. “Come in, come in!” She said before grabbing his hoof with her magic as well and dragging him into the house along with me.
Before we knew it we were dragged into Sunny’s room, where she was sitting in the bed watching a video on her phone. She looked in our direction when she caught the three of us out of the corner of her eye, to which she smiled at the three of us as she gave us a small wave.
“Hey Anon, busy day huh?” She asked.
At this point, I knew what she meant by ‘busy’.
“Sure has been.” I said.
“Oh, and hello Hitch. What brings you here?” Sunny asked.
“I got wrapped up in this guys busy day. ” Hitch said as he leaned into my leg.
Sunny didn’t get what he meant by that statement at first. The gears slowly turned In her head and I practically saw the lightbulb in her head light up when she realized what Hitch meant.
“No way.” Sunny said in disbelief. “When did you start swinging for the other team?” she said.
“Well, I’ve been thinking about it for a while. Just tried it out today.” Hitch said with a blush.
“Did you enjoy it?” Izzy asked with a beaming smile.
His blush grew and he simply nodded in response.
“Well good for you, Hitch. Proud of you for being so brave.” Sunny said.
“Oh stop it,” Hitch said with an eye roll. “I just was lucky I put my trust in the right guy.”
Both Sunny and Izzy aww’d at that last statement Hitch made, which made both of us blush and roll our eyes.
“Well anyways,” Sunny stated. “You still have a promise to fulfill, Anon.” She said while pointing her hoof directly at me.
I walked over to her and hooked my arms around her and collapsed into the bed together. I then pressed my lips against hers and we began to make out. Sunny let out a load sigh as she melted into my touch, and I felt a second pony come up from behind me and plant a few kisses on my neck. When I turned to see who it was, it was the cute little purple unicorn I expected to see. I ran my fingers through Izzy’s mane as I separated from the kiss with Sunny and planted a kiss onto Izzy’s lips as well, making out with her for same amount of time I did with Sunny.
“I guess I’ll see you three later.” Hitch said sarcastically as he began to walk away.
Without even skipping a beat, Sunny yelled out to Hitch.
“You sure?” He asked.
“Yeah, come on.” Sunny said with a hoof wave.
Hitch wore a skeptical look on his face, but soon he relented and walked over to the bed and jumped onto it. He crawled across my chest until he booped his nose to mine, we then hooked our arms around each others necks as we locked our lips. The two mare next to us reacted like school fillies at our homoerotic embrace, letting out high pitched squeals as we kissed. My response to there reaction was to flip them both the bird, making them laugh at my light hearted jab.
“Oh wow.” A new voice said which caused me and Hitch to separate.
The four of us looked over to where the voice came from and saw the royal sisters, Pipp and Zipp standing in the door way. I think both me and Sunny forgot that those two live here when they visit maretime bay.
“So me sucking you off wasn’t enough for you, was it? Just had to bang one more of your friends, huh?” She teased.
“What? Are you jealous?” I said jokingly.
“I little bit, I mean I’m kinda disappointed I wasn’t invited.” Pipp said.
“Yeah,” Zipp said. “We’re sleeping under the same roof tonight and you’re all gonna snuggle in here together without us? Doesn’t seem fair to me.” She said matter-of-factly.
“You can join us if you want.” Izzy said.
“Yeah, come on!” Sunny said waving a hoof to urge them to come over.
The two sisters looked at each other with smirks in there face before making their way to the bed. Pipp flew over to us on the bed, but Zipp had to walk because she was still walking weird from our roll in the hay. Pipp crashed her lips into mine as we began to make out, likely leaving yet another lipstick mark on my face. I then rubbed the base of her wings, forcing them to shoot out and causing her to let out an adorable little squeak.
“Wish I had wings,” Izzy said. “That looks like it feels great.”
“It feels amazing.” Pipp said when she separated from the kiss.
“Move over, it’s my turn.” Zipp said as she bumped her sister off of me with her rump and taking her place on my chest.
Pipp pouted as her sister proceeded to kiss me a lot more intimately than the other ponies did. shoving her tongue down my throat and immediately establishing dominance over the kiss.
“Hey, save some for the rest of us.” Sunny said jokingly.
“I'm here too, you know.” Hitch said.
“Ohhh, then come here handsome.” Sunny said with a giggle.
I looked over at those two and saw Sunny and Hitch beginning to make with each other like they had never stopped dating. Pipp then came up from behind hitch and wrapped her hoofs around his chest and kissed his neck. Izzy then snaked up my side and planted a few kisses on my neck and jawline as well. I hooked one of my arms around Izzy and pulled her closer to my side, my other hand traveled up the back of Zipp’s neck until I reached the top of her head. I combed my fingers through her hair before I grabbed a fistful of her hair and pulling on it hard, making her gasp at the sudden action. This moment of shock from her gave me an open window to become the dominant one in the kiss. I forced my tongue down her throat as I continued to wrestle with her tongue. But eventually we needed to separate from the deep and intimate kiss for some fresh air. I looked over at Hitch and saw the lucky stallion now locking lips with Pipp. I smirked at that display of affection before Izzy’s hoof pulled my face to the side and made me lock eyes with her.
“My turn.” Izzy said seductively.
Me and Izzy’s lips crashed together once again, and Izzy actually tried to deepen the kiss by slipping her tongue into my mouth. I allowed this and her tongue sheepishly entered my mouth, I playfully wrestled with her tongue, and she followed my lead and quickly became a natural. I then saw Zipp out of the corner of my eye lean over and grab Hitch’s face as he was separating from the kiss he was sharing with her sister. She then did the same thing she did to me and forcefully invaded his mouth with her tongue, and I saw Hitch’s eyebrows raise in shock. This shocked expression and small grunt he made, made me chuckle as I was locking lips with Izzy.
The six of us would continue to make out with each other until me and Hitch had kissed every mare in that room at least once. Of course, me and Hitch swapped spit as well, but we were mostly kissing our mare friends. Maybe if we had any more energy today, this would have turned sexual, but like I said earlier if I got into another sexual encounter today, they’d probably fuck my cock off.
But anyway, we continue kissing and hugging one another for so long Pipp had enough time to cover me and Hitch in lipstick marks. Pink marks being smudged on our lips, necks, and jawlines.
“Anon, you got lipstick all over you.” Hitch said after separating from the kiss he was sharing with Izzy.
“So do you buddy.” I said after I separated from my own kiss with Sunny.
“What really?” He said as he rubbed the area around his neck to verify my claim.
“Yeaaah, sorry about that Hitchy.” Pipp said with an awkward smile.
“No worries, I’ll just clean it off when I wake up in the morning.” Hitch said.
“Speaking of which, I’m tired of kissing and fucking you ponies. I’m ready for bed.” I said as rustled Pipp’s mane.
“Same here.” Sunny said with a yawn.
“Me too.” Izzy said before glomping into my chest. “I call dibs on this position!”
I laughed at her eagerness and rubbed her back and planted a small kiss on her head near the base of her horn. When I leaned back onto the bed Sunny curled up into my side and nuzzled into my neck. Zipp then crawled up behind Sunny and snuggled into her by wrapping her wings around her and then resting her head on her shoulder. On the other side of my body Pipp snuggled into me the same way Sunny was, and Hitch came up behind her and hooked his hoofs around her waist as he began to spoon her. I then wrapped my arms around the four ponies at my sides and pulled them in closer, and Izzy dug her snout deeper into my neck.
I looked around at all the ponies snuggling me in bed, all of them wearing blissful smiles on their faces. Knowing those smiles had formed because of me made me smile as well, and I don’t mean to stroke my own ego, but how lucky am I? Crazy how all of this started because I wanted a smoothie…
Ah shit, that’s what I was doing today! Can’t believe I forgot about my damn smoothie! Ehh, whatever, can’t complain too much about that. Besides, a smoothie couldn’t compare to the day I ended up having anyway.
