My head was being squashed between orange furred thighs, loud moans coming from the young pegasus mare’s mouth. She seemed to be having a competition with her friends, both of whom were moaning just as loudly. Considering that they each had three of my fingers twirling around and moving in and out of them and my thumbs pressing down on their clits, it wasn’t that surprising.

It didn’t take long for Scootaloo to arch her back with a loud scream of passion, her fluids flowing freely down my chin, then she fell back to the mattress with a heavy sigh. I stood up, keeping my hands moving with the other two at first, but then stepped back and caused them to groan.

I moved over to the couch at the side of the room and beckoned them over. They immediately jumped up and fought over who would sit in my lap, so I just spun them around, spread my legs, and sat them on a thigh each. I reached my hands around their sides and between their thighs once more, the two mares pressing back against my chest. Their moans started once more, as my fingers were now in a much better position to pleasure them.

My gaze was drawn by movement from the bed, where Scootaloo was slowly standing. She shakily walked towards us, and then dropped to her hands and knees, crawling the last few feet. She ran her hands over her friends’ thighs and then mine, our eyes locked as she rubbed the outside of my pants, giving a small gasp as she felt my rock-hard cock and I could see the pleading in her eyes. “Can… can I return the favour?”

I gave a small and still slightly hesitant nod, and her hands worked on undoing my pants. She couldn’t pull them down that far because of the other two mares, but it was enough. My view was blocked as Applebloom and Sweetie Belle leaned towards each other, bringing their muzzles together. I felt a hand slowly grip me, stroking my shaft, followed by warm breaths blowing across my tip. “Um… what do I do?”

“Just think of it… like an ice pop, but without the coldness.” A tongue flicked briefly across my tip a couple of times, followed by lips closing down around it. I closed my eyes as she slid her mouth further down, her tongue swirling around my organ. I opened my eyes when I felt a hand on my cheek, my head being towards Sweetie Belle.

She pressed forward into a passionate kiss, panting for breath once she pulled away. My head was then turned the other way, and my mouth was assailed by the taste of apples as Applebloom decided it was her turn. My hands were suddenly removed from their tasks, and I pulled away from the earth pony, glancing down.

Scootaloo had decided to take over, and I raised my hands up to the other two. They took a quick glance and then opened their mouths, beginning to suck their own juices from my fingers. I waited until they started moaning again and wrapped my arms around their chests, pinning their arms to their sides.

I could feel their hips bucking on my thighs, their bodies tensing as Scootaloo’s fingers worked at them. I could feel their arms trying to break free, but I held firm, and their heads rolled back to rest on my shoulders. I took another glance down to see the pegasus grinning around my cock, her eyes sparkling with delight as they locked with mine, and then she closed them again as she began to suck me off once more.

A few minutes later I took control back from Scootaloo’s hands, slipping my fingers back into the other two. I then felt moaning around my shaft and looked down to see the pegasus had slipped her hand between her thighs and was now fingering herself. I had to shake my head at what was happening then.

I mean, one attractive mare is pretty damn good, but three cute teenage ones, who were just barely legal? Come on, guys, we’ve all had this fantasy, right? Anyway, Sweetie Belle’s head rolled back with a loud scream as her walls clamped down on my fingers, her body shuddering from the orgasm.

Applebloom soon followed, much more loudly and violently, then joined her friend slumped against my chest, both of them panting for breath. I heard a groan of annoyance from between my legs, Scootaloo pulling away with a frown. “What the hay? Stallions don’t last this long!”

“You really want me to cum, huh?”

“Yes!”

“Okay then.” She gave a happy hum as she started to shift down again, and I closed my eyes, my cock twitching a moment later.. She then gasped as her muzzle and face was covered by my warm spunk, and she moved back a little whilst holding onto the base with one hand, the next few spurts hitting her breasts and clothes.

She tried to push my cock away, and succeeded in covering her friend’s legs with my seed, the pair moaning and whimpering slightly as I rubbed gently over their nethers. Once I had finished, I placed the pair down on the couch and stood, walking over to one of the closets. I took out four towels and threw three on the bed, the last one over my shoulder. “Showers are next door, and I’m pretty sure there’ll be something that fits you in here.”

“But.. ya got a shower in here!”

“Yes, Applebloom, but that one is mine. Yours is next door.” The trio gave a groan, but I shook my head and walked to the bathroom, locking the door behind me just in case. After a good twenty minute shower and drying off, I stepped back into the main room, where my mouth dropped open slightly in shock. “Well, what do we have here?”

Two of them gave muffled shrieks of surprise, whilst Sweetie Belle just smiled sheepishly at me. “Sorry, we just wanted to try them out. I can’t get mine in, though.” I walked over to the unicorn mare and stood behind her, taking one of my more private objects from her magical field. Neither she nor her friends could use their hands, as they had found my equipment drawer, and were now sporting a cuff around each wrist. They were locked by padlocks, and each pair was snapped together behind their backs with a third one. They had also placed cuffs around their ankles and locked them in place.

The stuff I said would fit them? Well, when you have mares over often enough, they start leaving stuff behind. Applebloom looked really good in the tight red corset and stockings combo, Scootaloo had light purple bra and panties on with a matching collar and leash, whilst Sweetie Belle just went naked.

I placed the rubber ball into her mouth and pulled the strap tight, buckling it in place. She gave a muffled hum as she tried to spit it back out, but had no luck. I started smirking at them as I brushed past to another drawer, taking out three new object for them. I quickly had one strapped to each of their crotches, and flipped the switches at the bottom. After quickly slipping into a thick robe, I took out the separate remotes from the drawer and walked towards the door. “Are you three coming back down then?”

They shook their heads at me, trying to pull their wrists apart, but their eyes widened as I flicked the remotes to on, the vibrators buzzing against their clits. Scootaloo was moaning the loudest due to the fact her gag was simply a bit, so wouldn’t really muffle much. Applebloom was the next one, the ring allowing sound out, but not letting her choose it by not allowing her lips to move. Sweetie Belle… the noises she made were muffled by the large red ball between her teeth. They all gave a small whimper as I flicked the toys off, raising an eyebrow at them. “Again… are you coming back down?”

They all nodded and brushed past me, and I heard their hooves thudding on the stairs as they rushed down them. I closed my door with a chuckle and followed, hearing muffled moans of protest from the private bar. I stopped outside the doorway as one of the mares began to speak. “Oh my, what did you do to get him to do this, Sweetie Belle?” That was Rarity, and her sister just gave a stream of mumbles in response, so I slipped into the room and walked over to the bar, getting myself another cider.

“They were already like that when I left my shower. Except for the vibrators, I did that.” I placed the remotes down on the bar and winked to the seven unbound mares, who grinned at each other. Seven sets of hands dove towards the bar, but only three of them managed to get a remote. I looked up when I heard some quiet giggling, to see a very tipsy Fluttershy.

“Oh… I wonder who I’ve got!” She dialled the wheel to full power and switched it on, all of us turning to the almost screaming unicorn mare. Sweetie Belle’s eyes were snapped shut as her hips bucked, and her lower lips seemed to try and suck the vibrator in. The buzzing stopped and her moans ended with a groan, drool dripping from her muzzle as she opened her eyes, pleading with the pegasus mare. “I’ve got Sweetie Belle! Oh this is going to be fun, I get to make her sing!”

I just winked at the others holding the remotes, and they walked back to the poker table. I grabbed hold of the leash around Scootaloo’s neck and pulled her over to the bar stool, sitting her down on it. Two more padlocks and her ankles were fixed to it, not allowing her to stand from the already moistened seat. A quick glance at them and the other two joined her, letting me lock their ankles as well. I heard a faint buzzing coming from between Applebloom’s legs, glancing over my shoulder to see who was in control of her.

The only one looking at me was Applejack, and she had left her hat on the table, her hand hidden underneath it. The other remote was in the hands of Pinkie Pie, which meant that Scootaloo was in for a rough night. I swivelled their stools around so that they were facing the bar, and made my way behind it, pulling out the stool that was still just a stall. Their eyes widened as I flicked the switch underneath again, the chairs buzzing hard against them.

After thirty seconds I switched them off, waiting for them to get their breaths back. “So, who was next again? Ah yes, of course! By this point, I had been with both Rarity, Twilight, and some of the castle staff a few times. It became apparent what my talent was after some rigorous testing, and still not having a job, I decided to take Rarity up on her suggestion. The next pony of the group I went with was also my first client…”

I knocked on the door of the cottage, just on the outskirts of Ponyville. I was almost sweating from the nervousness, even if I was ready for it. I mean, what if this mare wasn’t… well, not to say they’re all not pretty, but… anyway, I digress. I gave myself a glance over, smoothing out the suit that Rarity had made for me. The door cracked open a little, and I turned to see two luminous cyan pools looking at me. “Um… hello?”

I almost had a heart attack right there, the mare’s voice not belonging to someone who would call out an escort. I looked at the items I had brought with me, another suggestion of the fashionista’s, and picked them up, passing them to the mare. “Good evening, Miss…. Shy, is it?” She gave me a meek nod and I introduced myself to her. “I am here for our… appointment.”

Her eyes went wider than they already were as I said that, and she gave another nod, opening the door all the way. I walked into the cottage and looked around, smiling at the quaint feel. The mare, who I could now see was a pegasus, brushed past me and sat on one of the couches, so I followed and sat opposite her. “Um… can I get you some tea? No, wait, tea is not for this! Some cider, then? No, you’ll drink too much and won’t get it up! Um… oh dear, um… can I…”

I stood up and walked towards her, staying her squirming hands with my own. She looked up at me with a small amount of fear in her eyes, but that changed to relief as I spoke. “Tell you what, why don’t you wait here and I’ll get the drinks?” She gave a small nod and I went to stand, then looked down at her with a raised eyebrow. “Right… uh, kitchen?” She started to giggle, then pulled a hand away and pointed to a door to the side. Her cheeks lit up with a heavy blush as I kissed the hand I still held, and then I stood and made my way into the other room.

There was a medium size rack on one wall, and I started pulling the bottles from it. There were red, white, and rose wines, but I stopped and smirked when I noticed quite a few bottles of a cabernet sauvignon that I occasionally brought from Earth. There were a few of the same empty on the side, showing that she liked it. I managed to come across an almost empty bottle and grabbed two glasses, filling them up.

Once I returned to the lounge I found the entire room had changed. The thick curtains hid the slowly setting sun, and the light was provided by three candles around one of the couches. The mare had also gotten changed, her mane brushed out straight, and she was now wearing a very tight black dress, a stark contrast to the jeans and t-shirt from moments ago. I walked over to her and passed her a glass, which she downed half of in one go.

I chuckled as I sipped my own and then sat on the opposite end of the couch, turning to face her. I could see her eyes glancing in my direction as she sipped her wine, then set it on the table. “I’m sorry… um, I don’t know what to do in these… um, situations.”

“Not a problem. This… you’re actually my first client, so I can understand your nervousness. I’m worried as hell right now.”

“R-r-really?”

“Yep. Good at hiding it right?” We both nodded and then looked awkwardly at the table. I tried to think of good conversation starters, but found my mind empty. I mean, I knew the reason as to why I was there, but I didn’t want to just screw her and leave. Doing that to this mare just seemed… wrong. “So… how do want tonight to go?”

“Well, I think that’s... um, obvious, but I’d like… uh, to treat it like a date. If that’s okay with you…” I gave the mare a nod, picking my glass back up and taking a sip as she did the same. “Would you like some more wine?” I gave her a nod, and she started to smile, standing and making her way to the kitchen. I finished the last of the wine in my glass, slipped my jacket off and folded it over the back of the couch. I picked up the glasses and walked to the kitchen hearing small squeals of displeasure. “No, come on Fluttershy, you can do this! It’s just a bucking date!”

I peeked around the corner, seeing the mare at one of the counters, a bottle and corkscrew in hand. She seemed to be having trouble opening it, so I put the glasses down and walked up behind her. She gave a gasp of surprise as my arms came around her side, my palms resting on the back of her hands. Her head turned to look at me and I smiled back at her, nodding to the utensil. “Are you ready?”

“Um… yes, I think.” I gently moved her hands, twisting the corkscrew in. As we went deeper, I could feel the mare become more comfortable with the task, and slowly eased off. I left her after a moment and all was going well, until… “Buck, the cork broke.” I moved over and grabbed a knife from the side and the bottle from the mare. I got the cork free, but also managed to cut my finger in the process. “Oh dear, we need to clean that up!” I was forcibly dragged from the kitchen and sat on the couch, the mare pulling out a first aid kit from… somewhere. “Now, this may sting a bit…”

I didn’t think the cut was that deep, but she still poured some antiseptic liquid on my finger, causing me to let out a hiss of air. It was soon cleaned and wrapped in a plaster, the mare not realising she was straddling my thighs. Until I shifted them with a smirk, and she glanced down, then locked her eyes with mine. The blush I had seen upon Twilight’s and Rarity’s cheeks had nothing on this mare, and I couldn’t stop myself from wrapping my arms around her back and pulling her close.

Her arms came around my neck, and the blush only grew as she closed her eyes, her muzzle drifting closer until our lips met in a soft kiss. She pulled away with a soft sigh, her eyes fluttering open slowly. “Um… I’m sorry, I just um…” I silenced her by pressing forward, slightly more passionately, and felt her arms started to grip more firmly. I could tell what she wanted from me as she slid back and forth on my legs.

She gasped for breath when our lips broke, and a hand came around to stroke my cheek, whilst one of my started to run through her mane. At the rate this evening was going, I’d be back at my new house in Ponyville soon. She stood from my lap and walked back towards the kitchen, her hips swaying from side to side. I had seen plenty of mares doing that, normally followed by a stallion, and knew what it was a sign of.

I went to follow when I heard glasses clinking together, looking around to see the mare had gotten changed. Instead of her black dress, she was now wearing just black stockings and suspenders, giving me a full frontal view. I respectfully forced my gaze to her face as she walked over, bent down in front of me and filled the glasses. Instead of sitting on the couch, she once more took to my lap, handing one of the drinks to me.

We kept our eyes locked as we downed the glasses, which she then put on the table and turned back to me. She seemed to be deep in thought and then gave a nod,wrapping her arms around my neck. “Give me five minutes, and then come downstairs. okay?” I nodded my agreement and she pressed forward into a passionate kiss, pulling away with a slight moan as she grinded my crotch, then stood and walked over to another doorway.

I waited until I thought the required time had passed, standing and walking to the gap, where I then made my way down the stairs. It was a pretty empty basement, lit by a few candles, and I looked for the mare. There were a few crates blocking one corner, and I walked over, mouth dropping open in shock at what I found. “Um… oh dear, I didn’t do this right. Could you… um, put it in?”

I gave her a nod and lifted the ring to her mouth, slotting it behind her teeth and strapping it tight. Seeing as the rope around her chest kept her tied to the pole, and the one around her wrists kept them out of the way, there was no way for her to remove the gag. She glanced down to reveal a piece of fabric on the floor, which I discovered was a blindfold, and I quickly slipped it over her eyes.

I started to run my hands over her body, the mare giving slight whimpers as I got lower, eventually making it between her thighs. My fingers rubbed the outside of her folds, making her moan loudly. I noticed a few toys on top of the crate, and strapped one to her crotch. She almost screamed as I clicked it on, making it buzz against her clit. I then stood and unzipped my pants, pulling them and my boxers down, letting my hard cock free.

I placed the tip on the ring and felt her tongue flick over it a few times, before she started to bob her head back and forth. I placed one hand on the pole and the other on top of her head, closing my eyes as the sound of her muffled moans reached my ears, and I felt them around my shaft. Her tongue was swirling around, and she was trying desperately to close her lips around me, but the gag prevented her from doing so.

It was a few minutes later and I slipped from her mouth, the mare throwing her head back with a loud scream as her hips bucked at the vibrator. I waited until her moans finished and turned the device off, removing it from her. I then untied her from the pole and stood her up. She remained still as I bound her wrists behind her back and put another rope around her ankles. There was a hole through the pole at about chest height, so I slipped the slack from the rope around her wrists through it, then began pulling.

That forced her to bend at the hips with a small whimper, her arms being pulled above her. I tied the rope off and knelt down in front of her, lifting her face, even though she couldn’t see me. There was drool dripping from the gag and down her muzzle. “Are you ready?”

“Yespphh.” I walked behind her and reached into my back pocket, pulling out a condom. Thirty seconds later it was around my cock and I was pressing the tip of it against her glistening lips. She moved back, trying to get me inside her, but I just kept teasing and pulling away. “Pleasspphh…” I allowed her request, easily slipping in, and then placed my hands on her hips.

“Well, you want it, you use it.” She gave a small groan, then started to slide back and forth along my shaft, her walls massaging my length. She couldn’t really move much in that position, so I started to move myself, sliding in and out of the mare. I increased the speed and strength of my thrusts, watching as the mare’s hands clenched and unclenched around the rope, pleasured moans coming from her mouth.

I had no idea how long I was pounding away at her, her walls getting tighter and tighter, her moans now constant screams. With the speed they were coming I knew she was close, and traded speed for power, moving in and out slowly, but much more forcefully. It didn’t take long for her walls to clamp down on me as she let out a shriek of pleasure, her body shuddering as she reached orgasm once more.

I untied her ankles and the rope from the pole, but kept her wrists bound, removing the blindfold and gag. She blinked a few times whilst panting and then looked down. She spun around and slipped the condom off me, then dropped to her knees, facing me once more. She placed her lips around my shaft and began to suck me off again.

She added a bit of force to it, pushing me against the crates, which I gripped the edge of. Fluttershy’s tongue was everywhere, bringing pleasure to every nerve it could find, her soft lips feeling great as they were sliding along me. Now, I wasn’t in full control at this point, and felt my cock twitch a few times. She stopped for a moment as the first of my spunk hit her tongue, and then she began to suck in earnest, gulping down every last drop.

She stood up and began to giggle as I untied her, then took my hand and tugged me back up tp the lounge, where she reached for her purse. “Thank you for tonight. Now, I guess you would like to settle the bill and go, correct?”

“Well… depends.” She glanced over her shoulder at me, and I walked over, wrapping her in my arms and kissing the back of her neck, making her sigh softly. “Depends on whether or not you want me to stay. I’m free all evening.”

“You’d stay.. all night?”

“Yep. The after-sex cuddle is just as, if not more than, important as the sex. I wouldn’t deny that to anyone if they asked.” She took my hand with a happy smile and dragged me upstairs to her room, where I was stripped to my boxers and shoved onto the bed. I wriggled my way under the covers as Fluttershy traded her lingerie for panties, and slipped in next to me. I wrapped my arms around her as she found a comfortable position at my side, and then we both started to drift off.

When I awoke the next morning, I found I had the bed to myself. I slipped into my pants, and opened the door, a wondrous smell and beautiful singing coming up the stairs. I crept my way down and over to the kitchen door, finding Fluttershy busy at the stove. With a quick glance at the pan on top she moved to the side, where I could see her cutting some cheese.

I stealthily made my way over just as she set the knife down, and made her give a surprised squeak as I wrapped my arms around her and kissed the back of her neck. She then started to giggle as she pressed back against my chest. “Good morning. I thought I’d make you some breakfast.” I looked over her shoulder to see an omelette in progress, the cheese ready to be added.

“Thanks. What about you?”

“Oh, that’s big enough for two.” I gave her another quick kiss and pulled away, noticing the two glasses of orange juice on the table, and sat down to wait. It wasn’t long until the plate was set down in front of me, and we ate in silence. I shoo’d Fluttershy from the kitchen, telling her I’d wash the dishes, ignoring her protests. I even shut the door on her.

Once done I return to the vacant lounge and frowned, wondering where my host had disappeared to. I heard giggling from behind me and spun around in time for her to leap around my waist, pushing me back onto the couch, our chests squashed together. I brought my arms to steady her, and they ended up in her wings by accident.

At first I thought that was a bad thing, but Fluttershy let loud a loud moan as I ran my fingers through them, then pressed into a passionate kiss. At first I was surprised, but soon reciprocated, feeling myself growing once more. She noted too and pulled away, sitting in my lap and looking away with a sigh. “I can’t really afford another night…”

I placed my hand on her cheek and turned her to look at me, making sure she could see my smirk. “Office hours are eight am to ten pm.” Her eyes lit up then, and she began to grind her crotch over mine, her white fluffy robe opening partially to reveal she had nothing on underneath.

“Really? So what’s this then?” I made her giggle as I flipped us, kissing along her neck, her hands running through my slightly longer than usual hair.

“This? This is pleasure.” She bit her lip to quieten her moans as I slipped a hand between her thighs, her arms now tightly wrapped around my neck...

I smirked as the three bound and gagged mares opposite me whimpered slightly, having been forced by me and the three mares with the remotes to at least two orgasms each. I finished my cider and stood, walking over to the poker table. “Well then, ladies, seeing as we’re at the halfway point, shall we make a little bet?” They nodded at me, so I moved to the blank black board next to bar, and picked up some chalk. “Okay then, bets are ten bits each. You have two, which one will release first, and which one will release last.”

I grinned over my shoulder at the wide eyed trio, who watched nervously as six of the mares walked over and took the chalk, writing the names on the grid I had quickly drawn up. To keep thing fair, Luna and I would sit this out, as we always did. I spun the three bar stools around to face the room, and then slipped a blindfold over each of their occupants’ eyes. I took the remotes back and randomly placed them in their hands, dialed to full. “There, now you can try to beat each other, making this slightly fair. I don’t know who has got who, so it should be fun.”

They were all immediately clicked on, all three mares moaning as we heard the low buzzing. I moved behind the bar and turned the seats up to full power, then flicked them on, the trio giving surprised shrieks. After getting myself another cider, I walked to the table in the centre and sat down, Luna immediately hopping into my lap and pressing her back against my chest. I wrapped my arms around her stomach and blew warm breaths past her ears, leaning down and kissing her neck. “So… who’s your money on?”

“Truly? You.” Before I could ask, she slipped from my grip and to the floor, spinning around to face me. Her horn lit up and my robe came apart, revealing my semi erect cock. “Oh well, this will not do. ‘tis another problem that requires experienced royal attention.” She glanced at Twilight with a grin before bending forward, closing her lips around my stiffening shaft. I took a large sip of cider as she began, glancing around the six faces, all of whom looked like they wanted to change places with the alicorn of the night.

“Damn it, Squirt! You just lost me ten bits!” We all started to laugh whilst Scootaloo just whimpered as she came down from her orgasm. I just remained seated as her moans began once more. I’d have to go to the colleges tomorrow and explain why all three were sleeping in class...

Author's Note

Kinky Shy!!!