"Come on, my pretty little mare. It's time to go," Test said as he tugged gently on the leash attached to the leather collar around my neck. My face and ears were practically glowing red as I looked myself over. I was in my pink and black stockings, my collar, and a chastity cage around my sheath to keep me from touching myself. There was also the binding around the base of my tail which kept my tail up, exposing my balls as well as my tail-hole, which also happened to have a butt plug in it. On my face was makeup that Test had bought for me to wear to look even more like a mare. From eye shadow and lipstick all the way down to fake eyelashes, I looked like a mare. Test smiled as he opened the front door and led me outside. I was beyond glad that it was one in the morning as nopony was in sight but at the same time my adrenaline was pumping at the thought that, at any second, somepony could look at their window and see me as I was then. After he'd shut and locked the door, Test began to lead me down several roads in Canterlot. As we turned onto one road I saw a couple drunk stallions stumbling down the street, clearly blitzed beyond belief. They were coming in our direction and my heart began thundering in my chest as I saw them take notice of us.

"That's a pretty mare you've got, man. Mind if we have a go with her?" one of them asked as they got closer, my face blushing from him saying that and genuinely believing I was a mare.

"Sorry boys but she's all mine," Test replied with a wry smile as we passed them. I glanced back to see them checking out my ass and their eyes widening as they saw the balls between my legs. We kept walking though and continued to make our way through Canterlot to a destination unknown to me.

"Where are we going?" I finally asked as we turned another corner where Test had slowed down.

"I know a stallion from work who happens to own a gym that he runs as a hobby. I might've pulled a few strings and got him to let us use it for a few hours as long as we clean up afterwards," Test said as he continued to walk me down the sidewalk. "I hope you're ready for a fun night because I've got quite the lineup for you." He told me so with a devilish smirk as he stopped in front of a building. I turned my head to see the front of the building, which was covered in large windows that let you see all the exercise equipment inside. A gentle tug on my leash told me to start walking again and I followed Test as he pushed open the front door. The inside of the gym smelled like a combination of sweat and cleaning products. "They should be in the locker room waiting on us." We trotted back towards a doorway with a sign that said ‘stallions’ above it. When we stepped into the doorway, I could hear voices coming from around the corner of the small hallway. "Alright fellas, we're here!" Test announced as he rounded the corner into the locker room. The voices inside went silent and I trotted around the corner a few seconds after Test did. My eyes widened when I saw who all was there.

First there was a pale blue unicorn stallion with a two-tone blue mane. He pushed up his glasses with a hoof and he looked slightly nervous about being there. "First off is Final Cut," Test told me as he pointed to the blue stallion. Final looked up at me and gave a small wave before my attention was directed to the next stallion in the small group. He was a blondish-grey color with a dirty blond mane and tail. At his side were wings neatly folded back, and he smiled to me, his green eyes reminding me of emeralds. He looked familiar but I couldn't quite place where I'd seen him before. "This is Summer Winds. You might recognize him from his metal working shop in Ponyville." That's where I'd seen him. He'd been a few years ahead of me in school if I remembered right. The next one in the group was a brown unicorn stallion with a blond mane. His violet eyes were some of the most beautiful I'd ever seen. "Next up is Coffee Crash. He's a student in one of the science classes I help with." My attention then turned to the two at the end of the small group. There, at the end, sat a zebra stallion who looked both excited and nervous at the same time. He was a dark grey with black stripes rather than the usual white and black ones, while black and white dreadlocks hung down over his forehead. His green eyes were even more beautiful than those of the other stallions before him. But it was who or rather what that sat next to him that had truly grabbed my attention. There sat a brown and black gryphon. He smiled to me and seemed to have the air about him of someone that would be good to hang out and drink with. "And these two are Jali and William. William is visiting from the Gryphon Kingdom and Jali is here to take over if you need a break or just as another hole for us to fill." Jali blushed a bit at that as Test looked at all of the stallions before us. "Now, who wants first go with my mare?"

"I'll give it to him!" Summer Winds said as he stood up, a small smile on his face. Test led me over to a bench in the middle of the locker room where my front end was then laid down on it. I felt the plug in my ass begin sliding out in Test's magic, eliciting a small whimper from me as it popped out. Summer's forelegs quickly came down on either side of me and I felt the head of his cock already rubbing against my tail-hole. "You ready?" I nodded my head and in one quick thrust, he sunk himself all the way into me. His cock, while it didn't have as much girth as Test's, it made up for it in length. If I had to guess I’d say he was about thirteen inches long and he felt amazing inside me.

Summer suddenly pulled out and thrust back in, his balls slapping against mine and getting a high pitched moan from me as his cockhead hit my prostate. Another moan escaped me when I felt him begin biting on my ear as he truly began to thrust into me. I looked over at the others that were waiting their turn with me and grinned when I saw them all stroking their now rock hard shafts. Coffee Crash looked to be about twelve inches long and pretty close to the same girth as Test, maybe even a little bigger. Final Cut was about eleven inches and the same girth as Coffee Crash. Jali was the biggest length-wise of them being an impressive fourteen inches and slightly girthier than Coffee Crash and Final Cut. And then there was William. His talons were stroking a cock at least thirteen inches long with a knot slowly growing bigger at the base. I'd really need to get loose for that thing to fit in when his knot was at its biggest. Just the idea of taking that made me moan as my attention was brought back to the stallion rutting my ass. I could feel his hot breath on the back of my neck and the glorious feeling of him biting down on the scruff of my neck.

"Don't forget, he's got a mouth too," Test said. I then heard hoofsteps and soon saw the wonderful site of Jali straddling the bench in front of me, his dick was only a centimeter away from my muzzle and I quickly leaned my head in to begin sucking on it. A beautiful sounding moan filled the air as I took more of Jali's cock into my muzzle. "Final Cut, don't be afraid to jump in there," Test told the blue unicorn, who I then heard get up and trot over to the bench. Jali let out another moan as Final began to rim him, getting his hole nice and wet for what was to come.

"Oh Celestia, that feels amazing!" Jali cried out as Final's tongue slipped inside his tail-hole, his voice having a beautiful sounding accent. While I couldn't place it, it was certainly tropical sounding. Maybe some island country. He began panting at the assault he was receiving from both ends as more and more of his cock pushed into my muzzle. I opened my throat up as the head of his shaft passed the back of my mouth. The sound of Final sloppily rimming Jali stopped and I was beginning to get curious about it until the rest of Jali's cock was shoved into my throat as he was pushed forwards. In one thrust, just like Summer had done to me, Final hilted himself in Jali. A grunting above me got my attention and I felt Summer's thrusts getting more and more erratic. Just as the cock in my mouth was pulled back, I felt Summer shove himself in me as far as he could. He let out a moan and I felt his seed shoot out to paint my insides white. After several bursts that left me feeling full, Summer pulled his softening member out of me. My tail hole desperately clinched down on him in an attempt to pull him back in but to no avail. He popped out with a loud squelch and I immediately felt his cum running out of my hole and down my balls. I didn't have to wait long for the next cock though, as Coffee Crash stepped up and pressed his cock against my opening. He pushed in, using Summer's cum as lube, and immediately began thrusting as hard as he could. The feeling of his balls slapping against mine felt amazing and got a pleased moan out of me which in turn got a moan out of Jali. Just when I thought Jali was about to thrust his cock back into my throat too, he pulled out and scooted forward until his balls were pressed against my lips. Compared to Test's, Jali's were huge. I'd heard that zebras made almost twice as much cum as ponies and I didn't believe it until that moment. I carefully took one into my mouth and began sucking on it and rolling it around on my tongue, getting a satisfied groan from the zebra above me. I could taste the saltiness of his sweat and the smell was heavenly.

"I made sure to get these for ya since I know how much you love it." Test dropped five jockstraps onto my muzzle, the stench of stallion and gryphon musk filling my nostrils. I breathed in deeply and let out a pleased sigh at the glorious smell of ball musk as I continued to roll Jali's ball around with my tongue, which kept getting him to let out moans of pleasure. Between the musk of the jockstraps, the taste of Jali's ball in my mouth, and the feeling of Coffee Crash rutting me; I was starting to feel the familiar sensation of my balls pulling up towards me. With a moan of pure pleasure, I painted my belly and the bench white with my cum.

Finally coming down from my orgasm, I heard Test trot up by the bench. "Alright, everypony stop." I glanced over at him as Coffee Crash stopped thrusting but remained inside me. Suddenly, I felt Test's warm breath against my right cheek as he leaned in by my face. "You've made quite the mess. I want you to clean it up with your tongue, got it?" I nodded that I did and attempted to back up but realized that Coffee Crash was still inside my tail hole. "And you're going to do it while Coffee Crash fucks you. Understood?" I released Jali's ball from my mouth with a wet pop and he let out a quiet whimper in response.

"Yes, sir," I answered and Coffee Crash began backing up so that I could as well. We backed up until I was standing on all four legs again and my face was down by the bench. Sticking my tongue out, I began to lick my cum up off of the bench. I savored the salty taste as I began lapping up the white liquid, Coffee Crash now thrusting again with full force. Between licks, I would let out a feminine moan as Coffee Crash continued to rut me like a mare in heat.

As I licked up the last of the cum on the bench, I could hear steps on the floor of the locker room and they were coming closer to me. A shadow washed over me and I looked up from the bench to see William, the brown and black gryphon standing over me, his cock standing at attention between his back legs. Without a single word, he reached a talon up and squeezed my cheeks, forcing my mouth open for his waiting shaft. He shoved his length into my mouth all the way to the knot, not giving me any time at all to get myself prepared for it. I choked a bit at the sudden intrusion but moaned in euphoria as I felt the tip of his cock deep in my throat. I felt Coffee Crash’s thrusts begin growing more erratic though they certainly couldn’t get any harder. I felt somepony, who I realized was Coffee Crash, bite my ear. Moaning around the cock now thrusting into my mouth, I felt the stallion behind me hilt himself as the second load of that night painted my insides. Coffee Crash held himself there for a moment as his member softened before backing up, his dick popping out and my gaping hole leaking even more cum. As Coffee Crash headed for the showers, William pulled himself from my mouth and I looked up at him with pleading eyes.

“Patience, cutie. I’ve got something for you like you’ve never had before.” I watched him as he walked around behind me and grabbed my ass cheeks, getting a surprised squeak out of me. “I hope your coltfriend doesn’t mind me completely destroying your ass.” William said with a wicked grin that made me swallow hard in worry but at the same time made my cock twitch in its cage with anticipation. He looked down at the collar around my neck and I saw him look over at Test with surprise. “I’m amazed you haven’t got an Adamantite collar on if you’ve got a relationship like this.” He mumbled under his breath to himself as he looked down at me while lining his cock up with my hole. With a single thrust, he shoved his dick into me up to the knot. A high pitched moan escaped my throat and William looked over at Test with a smile. “He makes the cutest noises, doesn’t he?” Test nodded as he looked over to Jali and Final Cut, the latter having his tongue hanging out of his mouth in bliss as he continued to rut the zebra. Damn, he had some stamina, didn’t he? Although as I watched, Final Cut’s thrusts became more erratic and his breath was coming out in quick pants. Finally, he slammed his hips against the zebra’s rump and let out a loud moan as he emptied his balls into Jali. After a few moments of holding himself there, he backed up and his softening cock slipped from Jali’s abused hole. “Once you’re up for it, Jali; I want you to get over here.” William said as he pulled back and slammed his hips forward again, his knot stretching, but not totally entering, my used and sloppy tail-hole.

Jali was quick to hop off the bench and come over to us. I heard a click and looked back to see Test removing my chastity cage. “You’ve been pretty good, my handsome pet. As such, you’re getting a reward. You and Jali are going to frot each other which William switches between your holes. If you touch yourself with your hooves however—” He looked at me as he lifted the riding crop and a ball gag with his magic—“you’ll be in a world of pain you’ve never been before.” While the thought thrilled me and made my stallionhood quickly drop from its sheath and harden, I nodded as Jali slipped under me, his smiling face a welcomed change from the face fucking I’d gotten earlier. While I’d never been one to go for anyone other than ponies, I had to admit that being sandwiched between a gryphon and a zebra was the hottest thing that’d ever happened to me. With another thrust, I felt William’s knot grind against my hole, desperately trying to stretch it out so it could enter. Jali began to grind his hips upwards, rubbing his cock against mine. I moaned as I bit my lip, the sensations almost too much to bear. I felt my mouth open and my tongue roll out as I let myself get lost in the amazing sensation of being sandwiched between the two. A small laugh broke the trance though and I looked down to see Jali smiling up at me.

“Having fun?” He asked me to which I could only nod my head. With the smile still in place, he leaned up and pressed his lips against mine, his hips continuing to grind our cocks together. I felt his tongue snake its way into my mouth and begin to wrestle with mine, with me giving in and letting him have control after a half-hearted fight. William’s thrusts continued to get harder and with each one I could feel my hole stretching just a bit more as his knot pressed harder against it. I let myself relax as much as I could without falling down in an attempt to help him get the knot in. With one more quick thrust, I felt a searing pain in my backside, the likes of which I hadn’t felt since the night Test and I lost our virginities. William leaned down and nuzzled against my neck as my eyes watered in pain.

“It’s alright. Just give it a little bit of time to adjust. I won’t move until you say you’re ready,” William whispered as he continued to nuzzle me. Jali broke the kiss and looked up at me with a sympathetic smile.

“Don’t worry, I know how bad it hurts taking a knot for the first time. After awhile, you learn to enjoy it,” the handsome zebra said as he continued to lightly grind himself against me, earning small pleasured whimpers to leave my lips. “Now, just focus on me and let me show you a good time. Might help take your mind off the pain.” I flinched a bit as I suddenly felt the dreadlocks of his tail drag gently across my balls, the sudden stimulation making me bite my lip again to stifle a moan. Jali continued to tease me in this way until finally, I looked back at William. With a nod, I signaled that I was ready for him to move. He pulled back and his knot popped out, covered in the remnants of the cum inside me from the first two rounds. With a swift thrust forward again, he shoved his knot back in. The pain returned but with a slight hint of pleasure mixed in under it.

With William now fucking me with his knot, spreading my tail hole more than it had ever before, Jali began to resume his fun. With renewed gusto, Jali ground his hips up against mine, our cocks drooling precum and making it easier for him to slide our cocks against each other. “See, told you that taking a knot isn’t bad.” The pain from taking William’s knot disappeared entirely, leaving only the pleasure from each time he would thrust in and out.

“So does my little pet like my gift for her tonight?” Test asked as he leaned down to be face to face with me.

“Yes,” I replied to which Test grabbed the riding crop and brought it quickly down against my flank. I yelped in a mix of surprise and pain.

“Yes what?” he growled as he lifted the crop again, poised to bring it back down.

“Yes, Master. Your pet loves the gift you’ve given me tonight.” I moaned out loudly as William continued to fuck me harder than anyone had before.

“I’m glad to hear that. And I’ll make you a deal. If you make it through getting fucked right now without cumming, then I’ve got another surprise for you.” He smiled as he pulled my chin up with his hoof. “And trust me my darling, you’ll love it.” With a small kiss on my snout, Test stepped back and watched me, his horn lighting up. “Now do me a favor cutie. Smile.” I looked up to see a camera held in his magic. The camera flashed and Test lowered it with a smile. “I think that one should be our Hearth’s Warming card. What do you think, sweetcheeks?”

I was about to respond but only a whimper came out as William pulled out of me completely, leaving my hole gaping and desperately trying to grab onto something. I looked down at Jali just in time to see his face twist into one of pleasure as William shoved his cock, knot and all, into his tail-hole. He moaned and I smiled at the beautiful sound that came from him. William thrust hard into Jali, getting more pleased moans from him. After a couple minutes of fucking, the gryphon pulled out, only to shove himself into my hole again. A surprised gasp escaped me and I looked back at William who was looking at me with a goofy smile.

“You both have such amazing holes; I just can’t decide which one is more fuckable.” I blushed madly at his comment and moaned as he began thrusting with full force. I let my head drop and my tongue roll back out as he continued to switch between Jali’s hole and mine for about twenty minutes. Cripes almighty did that gryphon have some stamina. Finally, as he was rutting Jali, I heard his breath becoming ragged. “I’m gonna cum!”

“Me too,” Jali panted out at he was getting ravaged by William. I quickly turned around so that Jali’s cock was in front of my face. Without a moment’s hesitation, I opened my maw and engulfed the flared head of the cock in front of me. Jali let out a loud moan as I lowered my head and I could feel the head hit the back of my throat. I began bobbing my head and getting pleased mewls from the zebra under me. With my face that close to his tail hole, I could really smell the scent of sweat and cum as William continued to pound away at his ass.

With a grunt, William hilted himself and I could see his balls pull up towards his body. Jali moaned and I felt his cock throb in my mouth. Realizing what was about to happen, I quickly shoved myself as far down on his length as I could and braced for what was to come. Not more than a second later, I felt a torrent of cum being shot down my throat. After several bursts, I felt extremely full but Jali continued to cum, his orgasm easily twice the size of any regular stallion. When he finally finished, I pulled off with a small cough from the amount of time since I’d taken a breath. I looked over at Test who was staring at me with wide eyes and a raging erection. I followed his eyes to my stomach which was now slightly distended from the amount of cum I’d swallowed.

“Sweet mother of Luna. I didn’t even know that was something that could happen.” He muttered as he slowly trotted up to me. I smiled as I carefully stepped over to the side as William pulled out of Jali, a stream of cum pouring from his gaping tail-hole.

“What? You just thought that was something from those smutty romance books in your nightstand?” I questioned as Test put a hoof to my stomach. He looked up at me in surprise and I was quick to smirk at him. “Honey, you may be book smart but you certainly lack common sense sometimes. You left one of them on top of the nightstand and when I went to put it away, I found your little collection.” It was now Test’s turn to blush. I giggled as I turned and kissed him on the cheek. “Now, you said you had another surprise for me? I was a good little colt, and didn’t cum just like you asked.”

“Oh, yeah. Go on ahead and bend over.” I did as he instructed and I felt somewhat awkward with my rump in the air. Why, I did, I have no clue. Especially after the night I’d had. Test walked over behind me and I saw a bowl float over in Test’s magic. The bowl landed softly under me as Test began to run a hoof around my gaping tail hole. “You’ve got a damn fine gape going on back here. Big enough to fit a hoof actually.” His comment made my eyes widen and I started to stand but his magic immediately pinned me to the floor. “Now, now; did I say you could get up?” I recognized that tone in his voice. That was the tone of my Master and it meant that no matter what, I was getting a hoof up my ass. I swallowed hard as I felt him begin rubbing lube on my hole and gently pushing the tip of his hoof inside, only to withdraw it. “Now, consider this an order. You will not cum as a stallion. No. Instead, you’ll be cumming just as a pretty mare like you should. You ready for your milking my pet?” I simply nodded as I accepted my fate. His hoof gently pushed into my hole and I bit my lip to keep myself from moaning. “Now, now; don’t be biting your lip. Let’s hear those adorable little moans from you.” I did as I was told and let out a feminine moan as his hoof sank in deeper. I gasped as his hoof hit my prostate and he immediately stopped. Glancing back, I saw him smiling as he began to tease my prostate with his hoof. His other forehoof reached up and began to massage it from the outside. The feeling was overwhelming and I came close to cumming several times but somehow managed to hold myself back. Master had ordered me not to and I planned full well on following that order.

After about five minutes of the constant assault on my prostate, Test leaned down so that he was eye level with my cock. “Go ahead my pet, let your Master see your milk.” I felt a barrier collapse as I moaned out, my thick cum flowing in one go, not the usual bursts. It began to fill up the bowl and I bit my lip as I saw Summer Winds trot out of the showers, one of his forehooves drying off his mane with a towel. He sat down on one of the benches and smiled as he began enjoying the show before him. After a few minutes, the stream finally stopped and Test lifted the bowl up with his magic. “Now drink it.” I sat up as he put the rim of the bowl to my lips and opened my mouth. He tipped the bowl up and began to feed me my own cum, the taste of it making me moan again. “That’s a good girl.” I continued to gulp down the contents of the bowl until finally; I felt the last drop hit my tongue. Now that the last of it was gone, Test set the bowl aside as he leaned in and planted a soft kiss on my lips. “So, how’d you like tonight?”

“I loved it. Thank you so much, honey,” I replied as I nuzzled his cheek. “You know, if things go well, we could do this again sometime. If you want to, that is.”

“What? The gangbang or the milking?” He chuckled a little as he wrapped a foreleg around me.

“Both...” I said with a blush. The sound of talons on the floor made me turn around to see William walking out of the showers.

“You know, there’s a society I think you two would really enjoy being a part of. It’s for ponies and others who enjoy this kind of stuff,” He said as he tossed his towel into a nearby hamper.

“What’s it called?” Test asked as we glanced at each other from the corners of our eyes, clearly thinking about how nice it’d be to be surrounded by other ponies like us.

“They call it Clocktower.”

Author's Note

Thank you to all who volunteered their OCs for this chapter and a very special thanks to Glacier Wind who proof read and edited my small fuck ups. Go give him a watch and read his stories. He's got good stuff.