Having found a way to punish Scootaloo properly, the young pegasus mare gave a small whimper as I lightly tapped the crop on her hooves. She continued to do so as I let her up and she walked back over to the other couch, rubbing her hooves as soon as she sat down. I just sat smirking at the young mares with my hands behind my head, to which Luna and AJ took the opportunity to press against my sides, followed by Rarity sitting in my lap. “So the last one of the group was the weekend after the Running Of The Leaves. Although I had briefly met her, it was time for a proper introduction, so I joined the five at the town bar…”

I winked to Berry Punch as she slid a mug of cider over to me, and I took an appreciative sip. I turned around on the barstool when someone tapped me on the shoulder, and a mare instantly jumped onto my lap, her legs either side of me and her arms wrapped around my neck. “Hey.”

“Good evening, Skittles.” She giggled at that and lightly slapped my cheek, then started to roll her hips over my crotch.

“The name’s Rainbow Dash, but you can keep calling me Skittles if you want to.” I just threw her a wink and then introduced myself, tapping the stool next to me. The mare moved over and started looking over the drinks menu, but kept glancing over at me. “Hey...here’s an idea… know any good drinks from your world?”

I just rubbed my chin in thought before I spotted a few bottles from Earth, then winked at the mare again, turning to the bar owner. I was glad they didn’t have every type of alcohol here, allowing me to bring something useful to this world. “Hey Berry, mind if I mix a drink?” She gave me a nod, so I hopped over the bar, grabbing some alcohol, a mixer and a cocktail shaker. First came the gin, vodka and triple Sec, followed by Blue Curacao. I glanced up at Dash and decided to be nice, giving it a 1:2 ratio of alcohol to Nos fruit punch, then roughly shook the metal tube.

I got a glass, dumped a few ice cubes in it and poured the drink on top, then slid it halfway to the mare. “There you go, one ‘Speed Demon’ for the Wonderbolt. Don’t try to drink it in one go.”

“Oh yeah? Bet I can!”

“What’s the prize?” The mare just cocked her head and raised an eyebrow at me, whilst I smirked at her. “You want to bet, and I take that wager. I bet you can’t down it in one go.”

“Er… loser… loser is the winner’s pet or slave for the rest of the weekend!” I jumped back over the bar and offered my hand to the mare, still smirking away, and she grinned as she shook it. It was then I noticed the other five in a semicircle around us, and I heard Dash take a deep breath. “Okay… here we go!”

She picked the glass up and brought it to her lips, her eyes closing as she tilted it back. I got slightly nervous as she got a third of the way, then half, and my eyes went wide as the last of the liquid disappeared. It wasn’t until I felt a collar buckled, tighter than it needed to be, around my neck that my mouth finally closed and I noticed the smirk on the mare’s muzzle. She moved away and had a whispered conversation with Rarity, and the unicorn mare teleported away with a rather unladylike bout of laughter. “Skittles, what was that about?”

“Ah, you now call me ‘mistress’, is that understood?” I gave her a curt nod, and she slipped a finger through the d-ring, dragging me towards the exit. I didn’t even have time to finish my cider. We stopped at the town square, where Dash looked around confused. “Uh… which way to your house?”

“Mine? I thought we’d go back to yours.” She turned and glared at me, placing her free hand on her hip. “Sorry, mistress. It’s that way.” We walked off again, eventually reaching my average for the town sized house. I unlocked the door and allowed her to enter first, then made sure no-one was watching before I shut it back up. There was a flash of light and a box appeared in Dash’s arms.

“Well, looks like Rarity was already expecting this to happen. Show me somewhere I can get changed.”

“Yes, mistress.” I led her up to the spare bedroom, where she placed me in the corner and ordered me not to look. It took all my willpower not to when I heard a strange squeaking, but then I let out a surprised gasp as something hit my ass. Even through my jeans, it stung. I turned around, preparing to have a go at her, but stopped when I saw her attire.

She was wearing a blue latex teddy, with a corset over the top, suspenders reaching down to her bottomless latex stockings, completing the look with matching latex opera gloves, and in her hands… Where the hell did she get the whip from? At least I knew what had hit me now. “So then my pet, you need an outfit, correct?”

“Yes, mistress.” I walked over to one of the closets and opened it out, revealing a whole plethora of clothing. The majority of it was for mares, but I had a few outfits in there. Dash walked over and pushed me out of the way, humming as she searched through the items. She gave a small giggle as she pulled one out and held it up against me. “Hell no!”

“I’m sorry, what was that? It sounded like you were refusing your mistress. Bend over the bed please.” I did as instructed, knowing full well what was coming, but it didn’t stop the stinging sensation from my ass being hit again. Dash cracked the whip across me a few more times, then pulled me back to my feet by the collar. “Now you know what happens when you refuse me. Now, strip.”

Again I did what I was told, nearly ripping my clothes off, Dash then passing me the outfit. I shook my head as I took it from her, undoing the zip on the back. There was a strange squeaking sound as I slipped my legs in, pulling it up them, and then I removed the collar before putting my head in. Lastly came my arms, and I felt Dash do the zip up and secure the collar once more.

I then felt it pulled and she led me over to the other side of my room, standing me in front of my mirror. I couldn’t help but chuckle at what she had chosen for me, which was essentially a latex gimp suit without a crotch section, leaving my manhood exposed and semi erect. “Right then, where is your play room?”

I turned to the mare and gave her a muffled reply, making her frown at me. I then pointed to the zip covering my mouth, and she quickly opened it. “Down in the basement, mistress.” Her hands came up and closed the cover again, followed by the ones over my eyes. Her finger slipped into the d-ring once more as she led me through the house, her hooves echoing loudly on the wooden floors.

I heard her groan a couple of times as she chose the wrong door, but soon I was pulled along once more, carefully making my way down the stairs. Dash gave a gasp, muffled to me, as she clicked the light on, the mare having seen a certain corner. She led me over to the table there and made me get on it. I waited patiently as I felt cuffs buckled around my wrists and ankles, then spread out in an ‘X’ shape.

I was left alone for a few moments, but when she returned I was allowed to see how she was now dressed, having removed the teddy, but kept the corset and stockings, her marehood and breast on full display. Her wings gave a small flap and she ended up standing above me, then knelt down so that her crotch was over my neck. I could smell her scent even through the latex.

The zip over my mouth was undone once more as she shifted forward, the whip being placed behind my neck, pulling me deeper in. “Time to show your mistress what you can do.” I kept my gaze locked with hers as I flicked my tongue over her lips, teasing her ever so slightly. She gave a small moan and her thighs squeezed my head a little, Dash then growling lowly at me. “Well, I haven’t got all day.”

Giving a small shrug, I slipped my wriggly muscle past her folds, swirling it around inside. Dash’s hips bucked a little, but I just kept the stimulation up. She had to drop the whip and grip the edge of the table to steady herself as she bit her lip to keep quiet, but she soon let out a small shriek. It might have had something to do with the fact I had begun to nibble on her clit.

I could feel her hips rocking around over my chin; looking up to see her face, I noticed her eyes scrunched shut, and her mouth open with her tongue hanging out. Her moans were getting louder, her thighs squeezing tighter, and then she let out a loud scream. Her juices released over me, the majority going straight into my mouth as the mare shuddered from her orgasm, before she climbed off me, doing the three zips back up again. “Good colt. Now you can have a reward.”

Even though I couldn’t see her, I still lifted my head in an attempt to watch her shift down my body. It then fell back to the table with a thud as I felt her tongue flick across my cock, followed by her lips forming a seal around me. My arms and legs strained against their restraints, but there was nothing I could do.

I groaned as her teeth firmly, but gently dug into my skin, my entire shaft taken in her mouth. Having most of my senses removed or restricted heightened my others, most notably my sense of touch. As such, the oral pleasure she was given me was more intense than usual, and I soon felt my cock begin to twitch.

Dash stopped in surprise for a moment, but then began sucking harder as I released my seed into her mouth, my body tensing up from my orgasm. Dash moved away from my body and I heard her head back upstairs. There was thudding around for a few minutes before everything went quiet. I pulled at the restraints, trying to break free, but all I got was the sound of chains rattling.

I groaned as something cracked across my cock, then felt the tip of a crop dragged along it, followed by a hand stroking my thigh. “And where do you think you are going, huh? I’m not finished with you yet.” Her hand moved to my shaft, gently stroking it and coaxing it back to life. Her grip got tighter the bigger it got, until I was fully erect once more. “There, that’s better.”

Something cold was placed on my tip, confusing me at first, but then it was rolled down and I knew it was a condom. Dash then climbed onto the table so that she was over my crotch, and I could feel the heat from her nethers on my skin. She gave a small whimper as she lowered herself down over me, my dick slipping into her slick folds.

Her hips began to roll slowly around, her hands pressing down on my shoulders. I started to rock my own as well, shifting in and out of the mare, causing her to moan softly. I felt her body move so that she was laying along mine, her breast pressing against my chest. We both started to move faster, her moans now louder as her walls clamped down tightly. “Don’t you cum before me!”

I strained at my restraints desperately wanting to hold her close, but I also had to stave of my release. Thankfully, she threw her head back with a loud scream, and I could feel her fluids flowing to my crotch. I took that as the signal and my body tensed up again, my cock throbbing violently as I reached orgasm once more.

After our bodies calmed down, I felt the cuffs around my wrists unbuckled and I was pulled up into a sitting position, followed by the zip on my back being undone. I reached up and took the collar off, then slipped my head out, taking a deep breath. I opened my eyes and chuckled at the state of the mare, her mane clumped together and her fur matted with sweat. She climbed from my lap and I reached forward to release my ankles, then followed her from the table.

I slipped from my outfit then and helped Dash from hers, offering her a towel that I kept near the door for this very reason. My skin was wet from my own sweat, and I quickly had most of it wiped off. I just smirked at her as the collar was once more placed around my neck. “All weekend, remember?”

“Of course, mistress.” I offered her my hand and guided her upstairs to the bathroom, where I set the shower going for her. It was then that I realised the condom was still hanging from my dick, so i slipped it off and threw it in the bin. After a good twenty minutes Dash stepped out, taking the fresh towel from the side and wrapping it around her body.

She brushed past me and I entered the steaming downpour, increasing the water flow, the jets massaging my muscles. I didn’t stay in as long as her, but enough so that all of my sweat and our combined mess was gone, grabbing my own towel.

I entered my room to find Dash roughly drying her mane, wearing her normal panties and one of my t-shirts. I shook my head as I walked past her towards my chest of drawers and grabbing a clean pair of boxers. I chuckled as the mare’s arms wrapped around me from behind, her head resting between my shoulder blades with an airy sigh.

I turned around and kissed her forehead, making her giggle. I waved towards my bed and she moved towards it, wrapping her tail around my waist and pulling me along with her. I lay down on my back, Dash snuggling against my side. She darted her head up and softly kissed my cheek, then lay down on my shoulder with another giggle.

I started to run a hand through her mane, soft dainty snores filling my room a moment later. I reached up to the wall above the bed and flicked the light over, laying my head softly on Dash’s.

Dash sat up with a low moan, the scent from the fruits rousing her from her slumber. Her eyes fluttered open halfway and she stared at the orange segment in my hands, which she gently too with her teeth. I then passed her the bowl I had prepared for her and a spoon, the mare digging in enthusiastically. I had already eaten, not sure if she could take me eating bacon in front of her, even if I still had the smell on me.

I had slipped into jeans and a t-shirt, but the collar was still visible around my neck. I took the bowl from the mare and motioned to the glass of juice on the bedside table. I made my way down to the kitchen and added the bowl to the pile in the sink. Disgusting, I know, but I don’t like wasting water for one dish.

I chuckled as Dash appeared, pressing herself against my back. I was quite happy to let her stay like that, but we both groaned at the same time as there was a knock on my front door. I just sighed and made my way over, cracking it open to reveal a golden furred pegasus mare in a blue military style outfit, her two tone orange mane slicked back over her head. “Well, you’re not a pony, so this is the right place. Not too sure about your fashion sense though… Anyway, the name’s Spitfire, and I’m here to book you.” I glanced over the mare and took in her features, then noticed her shaking her head, raising an eyebrow at me. “I didn’t mean for me, for somepony else.”

“Let’s talk inside.” To my surprise, when she walked in, she grabbed the d-ring and dragged me into the lounge, where Dash was waiting. She had her legs crossed and was tapping the arm of the couch. “Our guest, mistress.”

“Mistress? So this is what you get up to on your weekends, huh Dash? Can’t say I don’t approve.”

“Well, make a seat for her, pet.” I just raised an eyebrow at Dash, and she took the collar from Spitfire, pulling me to my hands and knees. “Please, sit.” I then had the other mare put her weight on my back, happy that pegasi were light in general. “So, what can we do for you?”

“Well, I’m actually here to discuss prices with him,” I gave a small groan as the mare’s hand slapped against my ass, hard, “but not for me. For another pony.”

“I see. Well, why don’t you test him out a little?” Spitfire stood from me and Dash grabbed my collar, rolling me over and pushing me to the floor. I watched as Dash came over and slid the other mare’s skirt up, teasing the hem of her panties. To my surprise, Spitfire locked her lips with Dash, whilst my ‘mistress’ slid her panties down.

The pair gasped when they broke apart, and Dash knelt down, pulling Spitfire into position on my chest. She started shifting up my body, until her marehood was in my vision, her scent filling my nostrils. I put my hands on her thighs and lifted my neck up, flicking my tongue over her lower lips. She gave a light moan as I did so, Dash sitting back to back with her, and hand slowly stroking my semi-erect cock. “So then,” I looked up at Spitfire, who had her eyes scrunched shut as I continued. “How much for a stallion?”

I started coughing in shock, shaking my head as I lay it back to the floor. “I’m afraid I can’t help you, Miss Spitfire. You see, I don’t go with stallions. I’ll admit to being… curious though.” I gave a groan as something cracked across my now hard shaft, and I craned my head up, seeing Dash glaring round at me.

“Why not? You sucked Big Mac off.”

“Not by choice, Dash.” I groaned again as whatever it was slammed on my balls that time, Dash putting a crop into my view. “Sorry, mistress.”

“So… you’re open to negotiations. How much do you charge for mares?” Spitfire shifted forward so that her nethers were over my mouth, muffling my replies, so I stuck my tongue back in, making her moan once more. Her thighs started to close around me, then she pulled away, breathless and letting me respond. I did so after taking a deep breath myself.

“So… you want me to have sex with a stallion? I don’t know, it’ll be pricey. I mean, my rates for mares are fifty bits booked, seventy five impromptu sessions. I’ve never even considered stallions, even whilst being curious.” Dash whispered something into Spitfire’s ear, both mares giggling as they moved from me.

I noticed the gold pegasus mare leave the room, whilst Dash stood, looming above me, pulling me up into a sitting position by the collar. “Time for some more fun.” I swallowed nervously as a blindfold was slipped over my eyes, and then I was pulled to my feet. Dash started to hum as she walked behind me and pulled my hands behind my back.

I heard Spitfire return to the room, and then my wrists were pulled together, rope being wrapped tightly around them. It was then tied off, and I tried to free my hands, but one of those mares knew her knotts. My boxers were slid down my legs, and I felt one of the mares lift up a foot at a time, leaving me naked.

I was pulled forward by the collar and turned around, feeling a hand gripping my cock, knowing it was Dash just by touch. I heard Spitfire sat on my couch, and then I was pushed back. I felt her legs behind me and was pushed down, gasping as I felt something cold slipping between my ass cheeks. I immediately stood back up. “No! Hell no!”

“Oh, come on! You did that with Pinkie!”

“We didn’t use a strap on, Dash!”

“Then why do you even have one?”

“Because I… shit, haven’t got an arguement here.”

“No, I didn’t think so. We lubed it as well, so… down you go.” I felt her lips press against mine, Dash pushing me back down as we kissed. I groaned into her mouth as the tip of the fake dick slipped into my cheeks and pressed against my hole, Spitfire’s hand wrapping around my waist.

I grunted loudly as she pulled me down, the slicked shaft slipping in. I let out a small gasp as I felt myself hit Spitfire’s crotch, surprised to find that she had selected the smaller of the two. Hopefully it was her choice instead of just overlooking the bigger one. Aloe and Lotus certainly knew where it was. I then felt Dash grab my cock firmly, placing something cool on the tip. I smirked a little as what I realised was a condom rolled down my shaft, my mistress humming happily. She then put her legs around my waist and slid her warm marehood over my shaft, lower to my crotch. “So how about a hundred for a stallion?”

I just grunted once more as Spitfire rocked her hips, causing the strap on to slide from me, and push me deeper into Dash when she thrust back up. She did this a few more times, then stopped, letting me answer whilst Dash continued to bounce on my shaft. “I’m not… convinced. I mean… yeah, I had a… dick in my mouth, but… only once. To actually have sex with one…”

“Two, more than likely. Three hundred bits.” She started to move again, this time adding strength to her thrusts, making me groan in undesired pleasure. Coupled with Dash’s marehood clamping down around my cock, and the fact I couldn’t see, I felt myself starting to twitch.

“The answer… is still no.” One of the mares, and I’m not sure which one, rolled us over on the couch, so that Dash was on her back with me inside her, Spitfire in a position to assault my ass even more. She did so of course, pushing me deeper into Dash and pulling me out when she drew back. Then I heard her voice right next to my ear.

“Tell you what, two hundred per stallion… and a hundred for me afterwards!” I just grunted at a particularly strong thrust, my cock beginning to throb violently. “You can think about it, his birthday isn’t for two months.”

“I shall... consider it.” I focused on where I though Dash was, pushing my face close. “Please mistress… I can’t hold it any longer.” I felt her lips press firmly against mine, her tongue forcing entry. We moaned into each other’s mouths, then she pulled away and blew warm breaths over my ear, following with a whisper.

“Ready?” I gave her an eager nod, and I felt her hands placed on my cheeks, holding my head steady. “You can cum now.” That was it, my cock pulsed hard as my seed released, a long drawn out groan coming from my throat. My body slumped against Dash’s, breathing heavily. I whimpered slightly as Spitfire pulled away from me.

“Well, you drive a hard bargain, but so do I. But I don’t think we’re finished here.” I was pulled away from Dash and made to kneel on the floor, then bent over at the hips. Dash’s scent immediately hit my nose, so I moved my head closer and flicked my tongue over her marehood, making her moan slightly.

I grunted as Spitfire reentered, and Dash pulled my head back up. “Open up.” I did as instructed, feeling something round slip in. There was a leather panel over my lips, and I gave a muffled chuckle as I realised what she had found, waiting patiently as she buckled the gag tight. I knew what was on the other side, doing my best to put it in. Dash had to guide me as I couldn’t see, but soon the attached dildo was entering her folds. I gave another chuckle as I heard buzzing behind me, Spitfire having worked out that the dildo on the inside of the strap vibrated.

She started thrusting again, dictating how I moved in and out of Dash, the two mares moaning as I groaned and grunted, Dash holding a hand behind my head and preventing me from pulling away. I felt myself growing once more, the fake dick in my ass not feeling too bad now.

Both mares then let out loud screams of pleasure, and I could feel their bodies shuddering hard as they rode through their orgasms. They both pulled away from me and I blinked as the blindfold was removed, the light hurting my eyes at first. I looked at the didlo coming from my face and chuckled at the juices that coated it. My head was then turned to face Spitfire, who took the entire shaft in her mouth, keeping her eyes locked with mine as she slid down it. “Loopphh, I’mpphh a unicorpphh!”

She then let it go, swirling her tongue around it as she backed over. “Well, this was fun. So… we’ll discuss more at a later date?”

“Surpphh. Comphh bacphh inpphh aroundpph a monpphh.” She nodded at me and kissed my forehead, then stood up. I didn’t expect Dash to see my guest out, so stood as well, waiting patiently as my mistress removed the didlo from the gag. I then walked into my lobby with Spitfire, turning so that I could open the door.

The mare gave a gasp and I heard a surprised squeak as a pony fell in. We both looked down to see Fluttershy staring back up at us, her wings spread wide with a bright blush on her face. “Oh... um, excuse me, I didn’t want to interrupt. You sounded… um, like you were having fun.”

“Well, well, looks like you have two mistresses now. Have fun. Spitfire gave me a grin and helped Fluttershy to her feet, then stepped out and shut the door. I took the new visitor’s hand, and walked back to the lounge, Dash giving a gasp of surprise. She jumped up from the couch and walked towards her friend, slowly stroking her cheek.

“Hey, Flutters. What are you doing here?”

“Um… well, I wanted to… um, see if he was busy.”

“Not right now, but he will be in a moment.” I just raised an eyebrow as she pressed into a passionate kiss, gently moving Fluttershy’s hands behind her back. I then saw the handcuffs that Dash held, and they were quickly around the smaller pegasus’ wrists. Pretty soon she was stood next to me, stripped to her stockings and suspenders, the cuffs replaced by rope and her own ballgag in her mouth. “Right then, Shy, come here.”

I glanced over my shoulder to see Dash had gotten the other strap on, and was standing at the base of the stairs. The bound mare did as instructed, and Dash waved me over. We both had collars on now, and she attached leads to them, pulling us up to my room. She let me go, but took Fluttershy over to the bed, where she had her lay down.

Dash then turned to me and reached for my crotch, removing the used condom that I had forgotten was there, putting a new one on. She moved back to the bed and shifted Fluttershy around so that Dash was on the bottom, the shy mare giving a whimper as the the toy slipped between her thighs.

Dash’s hand came down and pulled Fluttershy’s tail out of the way, and her other one waved me over. I grinned around my gag as I did as instructed, gentling probing my cock against Fluttershy. She gave another muffled whimper as she pressed back, telling me to enter, which I did all too eagerly.

“Wait, what happened with Fluttershy and Dash?”

“Well, right now, Dash is probably at Fluttershy’s cottage, playing with her pet.” I nodded in agreement to Rarity’s statement, looking over to the stunned faces of the younger mares. “They have been meeting each other once a week since then. But what about your mistress?” I just winked at Rarity when she turned to look at me, giving her my reply.

“I’ll tell you when we get back to Ponyville.”

“Wait… you still do that for Dash?” I smirked over to Scootaloo, who was now sat at the edge of the seat, paying the utmost attention to me. “You still take the role of her pet?”

“You’ll have to ask her if ‘pet’ is the right word these days. Either way, I think we’ve come to the part you three are going to enjoy the most. My lovely mares, could you give us some privacy?” One by one, Luna, Applejack, and Rarity gave me a soft kiss, then stood and left the room. I stood too, but made my way over to my drinks cabinet, selecting a weak wine.

After filling four glasses, I put the rest of the bottle in a bucket of ice and took it over to the coffee table. I noticed the light levels had gotten pretty low, so went over to my fireplace and got a nice one going, returning to my couch to see the three young mares staring intently at me. “What?”

“Well? Aren’t ya gonna tell us somethin’ excitin’?”

“Oh yes, but you may want to relieve your parched throats first.” The trio snatched up a glass each and took a few sips, before settling back against the couch. “Well, I guess you’re going to want to know how I got my cutie mark, right?” Their eyes went wide, making me smirk at them. “First… let me see yours.”

Author's Note

All I can say is; Yes, mistress.