While Diamond Tiara and Silver Spoon met with his new playmate out in the hall, Button felt a once-over in the mirror was a must. His generous, albeit snobby friends deemed this pony worthy enough to either play with them, or at least one of their toys, so it wouldn’t hurt to make sure he was looking his best. First impressions and all that, he thought wryly.

Stepping up to the vanity table, a seeming neutral territory between the two sides of the dorm room, he dropped his purse down on the surface. Applying some lip gloss from his clutch, he couldn’t help but smile as something Silver Spoon had said came to mind. “She’s so eager to meet her new playmate.” She, as in a woman. Could it be that they were throwing him a bone before his was completely useless?

It really should bother me that this is happening to me, he thought as he adjusted the glasses Silver Spoon had provided for his outfit. At the same time, though, I can’t deny that this feels right. It might not have started out as my choice, but I chose to let it get this far. Sure, the sodomy felt a bit gay at first, and I never would have myself pegged for trans, but just look at me! Pirouetting, he smiled at his reflection. I’m much more confident, I’m hanging around with actual ponies, and besides; I’m fucking cute!

“Oh thank God,” said someone behind him, startling him free of his musing. “With the way they kept going on, I thought for sure they were going to set me up with some stallion.” Wait, why would you expect a stallion here?

Button whipped around in alarm, fearing what he might see. He’d certainly heard that voice enough over the PA over the last year and a half at Canterlot Higher Education Institute to recognize it. The dulcet tones that announced all student council related news reminded him every day of a missed opportunity. It could only belong to one pony he knew. Pink and lilac tresses—once curly and parted above her horn in childish mimicry of her sister’s signature look—greeted him, now pulled back in a no-nonsense bun. Those unmistakable green eyes, surrounded by an ocean of milky-white fur.

“S-sweetie Belle!?” Button squeaked, trying to wrap his head around the fact that his childhood friend was the one Diamond Tiara and Silver Spoon wanted him to have sex with.

The unicorn mare in the doorway blinked in surprise, and then furrowed her brow. “I feel like I should recognize you, but I can’t figure out where I would know you from,” she said, crossing her forearms. Beneath her casual blue sundress, her rather ample bosom bulged out over her arm, seemingly taunting him. Her horn glowed for a few seconds, as if to cast a spell, but he saw no indication of a spell being directed his way. Memory charm maybe? “Are you one of the freshman councilmen, by any chance? I wouldn’t usually forget a cutie like you, but with so many quitting and joining the council lately...”

“You, you don’t recognize me? Not even a little” he asked in a hurt voice. Why did I say that? Do I really want her to know I’m me? If Diamond Tiara and Silver Spoon were beautiful, Sweetie Belle was drop-dead sexy. Finding out that she had a similar relationship to the one he had with them was strangely exciting. At the same time though, she was a treasured childhood friend. Could he really have sex with her?

The pain in his voice drew her attention fully to him. Striding over, out of the doorway, Sweetie came to a stop just inches from Button, towering over him by a full head. She’d definitely grown since they were both kids. “You almost remind me of a boy I grew up with,” she said with a frown. “But you could barely get him away from his video games without him having a panic attack, never mind getting him into the women’s dorm. Besides, he’d never get involved with Diamond Tiara and Silver Spoon like I did.”

A grin settled across his face at her words. “You don’t think so?” he said, dropping his feminine tone and removing his glasses, discarding them onto the vanity. Hearing her imply that he couldn’t be like he was felt like a challenge. I did get involved with them, and I can make you feel good. “You’d be surprised how life throws you a curveball.”

She blinked, staring unbelieving at the pony before her. “Button? What... why are you dressed like that?”

A manicured finger came to rest on her lips as he reached up to silence her. “You and I probably do very similar things with them; does it really surprise you that they’d do something kinky like this?” he whispered. “Right now, though, I’m not Button, and you’re not Sweetie.” Removing his finger from her lips, he reached down and undid the top button, revealing a bra strap as he pulled one side of his blouse away. “I’m just a sissy toy being shared between friends right now.”

The backs of her legs bumped into the foot of Silver Spoon’s bed, impeding her disbelieving retreat. Catching sight of the camera aimed in that direction, Sweetie frowned. “What did they do to you, Button?” she whispered under her breath. “Doesn’t this feel wrong to you? We grew up together; you’re practically my brother!” Quieter, she added, “I don’t want you to see this side of me.”

He giggled girlishly as he slipped back into his newly-christened Dee role. “They taught me that just because something feels wrong, it doesn’t mean that it can’t feel good, too.” She hadn’t expected him to be so forward, so she had no manner of preparation when he suddenly pushed her back. Adorably, she clutched the front of her dress tightly against her rather than attempting to break her fall, protecting her modesty and depriving him of a panty-shot in the process. “Let me show you.”

Button joined her on the bed, slowly climbing up over her legs and planting his knees on either side of her hips. “Tell me you don’t want this,” he whispered as he traced circles on her belly with his fingertip. When she mewled pitifully at his teasing touch, a memory struck him. “They always say they don’t want it at first,” he said, repeating the words from one of his first training sessions with Silver. “You just have to show them how much they really want it.”

His palms came to rest on her waist, and he slowly, sensuously dragged them up her body, pulling the dress up as he went. With every upward inch, he dug his fingertips in just enough to provide some pressure, eliciting a moan from her as she arched her back in response to his teasing. He was met with no resistance when it came to removing the dress entirely; she blushed slightly as her breasts were bared, but obediently put out her arms out to allow it to slide freely over her head.

He stared down at her body, marveling at how different Sweetie was from Diamond or Silver. If his mistresses were petite and lithe like dancers, his new playmate was an Amazonian princess. Besides being tall for a mare, she had wide, child bearing hips. Despite being in the music program, she looked to be incredibly fit, and it felt like he was only in charge because she let him. Then there were her breasts. Silver and Diamond’s were only As and BBs respectively, while Sweetie’s were like two gigantic mounds of ice cream capped with nice rosy-pink cherries. Surely they were at least an E.

All of this was ripe for the picking—all his. As he felt his member harden within its silken sheath, his instincts told him to dive right in and take this mare right then and there. Fortunately, Silver Spoon’s training stayed his hands. Instead, he leaned forward, pressing his body into hers and easing his face into the curve of her neck.

Taking a deep breath, he let out a moan of his own. “Your scent is intoxicating,” he purred as he nuzzled her neck. He snaked his hands behind her, slowly running them up her back and neck. “What perfume are you using?”

“It’s, uh, it’s—ah!” she cried out as his fingertips found the edge of one of her ears. “I can show you if you just—” Pinching the apex between his index finger and his thumb, he rubbed her ear tenderly, just as Silver Spoon had shown him. “Oh whatever you’re doing, don’t stop!”

Button giggled into her neck. “But if I don’t stop teasing your ears, how will I show you how well my mistresses trained me?” he asked pleadingly as he traced a finger down the other side of her neck. “I am, after all, trained for your pleasure.”

Sweetie moaned as he gently nipped her shoulder. He felt her move one of her arms and imagined she was biting into a finger to keep herself from crying out. “What have they been doing with you?” she whined as he bit down gently once more, just above her collarbone this time. “They just make me have sex with them until they’re f—unh! Why are you so good at this?”

Pulling away from her shoulder, he looked up at her with a playful glint in his eyes. “Mistress Silver says if you want to be a girl, you must know how to please one,” he replied. He knew he was going to regret this next statement but it only felt right to give fair warning. “I apologize if this next part is unsatisfactory; Mistress Diamond is the largest I’ve been permitted to work with and breast play isn’t a big portion of our sessions.” He moved down her body and pressed his cheek against her bosom. “I hope mine might get to be this big one day, Sweetie; they’re so nice and soft.”

He popped her left nipple into her mouth and began to roll it tenderly between his tongue and teeth. With one breast occupied, it seemed unfair for the other to be left alone, so he brought up his right hand and started softly rolling and kneading it as though it were pastry dough. With each suckle and each squeeze, he felt himself growing fully erect and straining against his panties.

“I don’t get why you would want to be a girl,” she said between gasps. “Why would you want huge boobs like mine?”

Looking up at her with lustful candor, he said, “They’re sexy; you’re sexy. I want to feel sexy too.”

“Guys can be sexy too,” she moaned as he gently pinched her right nipple. To his ears, it sounded like she was trying to convince herself rather than him. “Nnnnh, stop for a minute. I’m trying to be serious.” Groaning, he allowed her to push him away. “Why do you have to be a girl to feel sexy?”

He looked at her pensively for a minute before frowning. “Like this, I feel confident. I’m not afraid to speak my mind,” he replied, rocking back to grind against his erection her knee. “It’s so exciting... being treated like a mare instead of a loser colt.”

“You weren’t like this when we were little,” she whispered sadly.

Placing his palm against her white cotton-clad pubic mound, he smiled. “And you weren’t like this when we were little,” he chided, rubbing his hand back and forth. Button grinned and brought up his hand to show her the strands of sticky arousal stretched between his fingers. “Someone’s enjoying this more than she lets on.”

He offered her his hand more in teasing jest than any expectation and was genuinely surprised to see her take his fingers into her mouth. The wet warmth of her oral cavity was second only to the exciting sensation of her tongue flicking across every inch of his fingers. When she pulled it away, all the marecum that had coated his fingers had been replaced by her saliva.

For a split second, Sweetie Belle’s eyes crossed as she swallowed, and then a lewd smile split her face. “You’re right,” she admitted, clasping her breasts in her hands and squeezing them gently together. “I’ve never really liked boys in that way, but looking at you dressed like this... It’s so... erotic.”

Releasing her chest, she reached down and—with a combination of magic and her superior strength—pulled him up until his face was right in front of hers. Button didn’t need an invitation; he leaned into her and pressed his lips against hers. She slid her tongue into his mouth, wrapping his in hers and sharing with him her tangy, sweet flavor, before pulling away. “I hope you’re ready for a big surprise, because I’m not stopping now.”

Button sat up in confusion and was just about to ask what she meant when something prodded his pantied bottom. Raising himself off of her entirely, he nearly squealed in equal parts alarm and delight as he looked at her groin. Her panties, once tight against her body, strained to contain a very large erection that simply couldn’t be there.

Yet there it was, a penis as long as his forearm, leaking precum through her panties, and it looked as though it was still growing. The scent in the air—one he’d smelled enough times at the end of his sessions with Diamond and Silver when his panties were absolutely filled with cum—was unmistakably male. How is this possible?

He opened his mouth to ask, only for his voice to die in his throat. “You’re wondering about my little friend here, aren’t you?” She caught the waistband of her underwear with her thumbs and freed the pink pillar of flesh. He watched as it slapped up against her belly, coming up just barely between her breasts. “I got this when I turned ten. Apple Bloom tried to make me taller with one of her potions. Not only did she turn me into a guy for a week; this little fellow decided to stick around.” She ran her hand down the slick length, smearing it with pre and moaned. “I don’t have my clit any more, but sometimes this is way better.”

Barely a word of it reached him. His eyes were fixed on Sweetie’s dick. It was like it was calling to him. Play with me, it begged, twitching with excitement. Not only that; compared to this gorgeous beast, his was absolutely miniscule. It was frankly intimidating in that respect. He reached out a trembling hand to give it a stroke, to confirm that it was real, but pulled it back when it twitched. “May I... touch it?”

“Of course you can touch it,” she said in a tone that reminded him far too much of her older sister. It was a tone that made what she said less a suggestion than it was something expected of him. Any power that he had was gone now; she was fully in control. “You did make it hard, after all, and it wouldn’t be nice to go back on your word after insisting you would make me feel good.”

She grabbed one of his hands and placed it on her shaft. “By the way you reacted, upon seeing this, you’re used to playing with those of others... or at least toys.” She gave his hand a reassuring squeeze. “Show me what you do for them.”

Button looked up from her penis, again caught off guard. Is it a trap? A test? He nodded and, removing his hand from her cock, climbed off the bed. Taking up a kneeling position, he watched quietly as she sat up and swung her legs over the edge. He leaned down to take a lick, but his vision was tinted green as he came to a sudden stop.

“The cute glasses you were wearing,” she said, levitating the glasses over. “I want you to wear them while you do it.”

“Not the strangest request,” he whispered, accepting the proffered article. Once the fake lenses were resting on his face and Sweetie nodded her approval, he leaned forward once more and kissed the tip of her cock as he wrapped a hand around the base. His mouth slowly opened, permitting his tongue to dance across the slick surface. If her marehood had a sweet taste, her cock was earthier, with a vinegary kick that reminded him of salad dressing. It was a tad bitter, but not unpleasant.

He moaned his approval into her flesh, eliciting a cry of her own. Taking that as his go signal, he led his tongue on an adventure down her shaft, occasionally stopping to trace out a random letter or shape upon her intimidating length. She was practically shivering by the time he reached her base, and when Button forced his tongue past the waistband of her panties to lap at the top of her slit, she squealed and grabbed his hair. Sweet moisture splashed against the tip of his tongue, and the gusset of her panties grew even damper as a micro-orgasm rocked her.

Like the dog he sometimes was, he ran his entire tongue sloppily up her entire length, savoring the taste of her precum. She rewarded him with a fresh spurt into his eager mouth when he reached the top. Looking up at her from between her legs, he grinned as he took her flare into his mouth.

His tongue flicked across her urethral opening as he readied his jaw. She was much longer and thicker than what he was used to, but unlike the toys he frequently prepared this way, Sweetie Belle’s penis was a lot softer. It would yield to the tight confines of his own throat far more than the rigid rubber strap-on that had broken him in ever had. It slid into his mouth easily enough; between the pre slathering her rod and the saliva he’d applied, it reached the entrance to his throat in one easy movement.

At the same time, Sweetie released her grasp on his mane as she redirected her focus to his ears. As he had done to her before, she began tracing her fingertips up the outside curves, causing them to flick and twitch from the electric tingle of her touch. “Oooh, looks like someone else has really sensitive ears too,” she teased, switching to a massaging touch as she prodded his tonsils. “Mmmh, you shouldn’t be as good at this as you are...”

She lost control of herself for only a moment, thrusting forward with a grunt, but it was more than enough to nearly choke him. He was unprepared for the sudden thrust, and the sensation of her flare popping past his tonsils tore a panicked groan from his chest, sending pleasurable vibrations back up her shaft. Remembering what he’d been taught, he calmed himself and adjusted his body posture, straightening his throat.

Placing his hands on her round, soft bottom, he leveraged himself further onto her cock. He hummed and moaned into her shaft as inch after glorious inch slid down his throat. The medial ring had barely cleared his lips when he felt an uncomfortable pressure at the opening to his stomach. Knowing his limits, he immediately began to withdraw the length from his throat—only for Sweetie Belle to grab the back of his head.

Once more asserting her control over the situation, she bucked her hips as she held his face, forcing her cock back down his throat. With her assuming direct control, there wasn’t much that he could really do with his mouth other than sit there and play the role of her fleshlight. For all the times he had practiced fellatio on Silver Spoon’s strap-on, he’d always been the active one; never having received any stimulation from it, Silver never saw a point in thrusting. Fellatio was just a precursor to getting pegged.

“Don’t just sit there groping my butt,” Sweetie moaned. “Use your hands!”

Oh yeah, he thought, condemning his own idle mind. Sweetie was definitely a unique case to work with. With just over half her cock pistoning into his throat, there was still a sufficient amount of flesh exposed that he could jerk while she fucked his face. Not only that, but her seemingly hermaphroditic nature made it possible to pleasure her twofold. Why didn’t I think of that sooner?

Button brought up his right hand, and wrapped it around the base of her cock. When he began to rhythmically pump his hand along the slick length, he heard Sweetie’s breathing intensify as she began to moan rather loudly. “I’m so close,” she said as her fingers dug into the back of his head. “More!”

If you like that, you’ll love this, he thought, smiling inwardly. With his free left hand, he pushed aside the damp crotch of her panties and eased a finger into her wetness. His finger danced and probed her moist crevice, searching the front wall of her birth canal eagerly for the G-spot he knew had to be there. Diamond Tiara had shown him it wasn’t the exact same for all women, but if he could find it, he’d have his reward. Oh, how I want this reward.

Eventually, his probing digit found something he hadn’t encountered with Silver or Diamond; where he suspected he would find Sweetie’s G-spot, he found instead a walnut-sized nodule close to her cervix. He hummed curiously, wondering if this was what he assumed it to be. Mares don’t usually have prostates, but then again, most mares don’t have monsters like this, either.

Her entire body shivered with pleasure above him as he grazed it, and he could feel her cock begin to flare, slowly ballooning and wedging in his throat. He tried not to panic as the pressure in his throat threatened to block off his airways and instead focused doubly on what he was doing. Peering up at her with mischief in his eyes, he inserted another finger into her vagina. Up it went to join its brother right next to her prostate. With a throaty moan and a wink, he jammed his fingers into the mass.

A loud squeak was the only indicator he had that he’d just opened the floodgates. The first wave immediately followed, surging down her length. Her cock swelled even more, and without any other warning, he felt something blindingly hot splash into his throat. It began to pool quite fast, and there was really only one place it could go; discarding the last pretense of being a ‘normal’ guy—for what at all was normal about any of what he’d done?—he began greedily swallowing.

Even had her cock not already wedged itself in his throat, ready to deposit its seed, he wouldn’t have been able to escape; her legs had clenched tight around his head, the moment his fingers pressed into her nodule, holding him tight. All he could do was patiently sit as wave after wave of hot semen flooded his throat. Trying his hardest not to let any go to waste, he pumped his hand along her length, milking her cock for all it was worth. Even when he felt his belly begin to grow uncomfortably tight, he kept on swallowing. When her flare finally deflated, Sweetie Belle released his head entirely and began to withdraw until just the head was in his mouth.

Eventually, when swallowing any more threatened to rupture his belly, he opened his mouth and allowed her to fire her last strands of cum onto his face. The hot seed splashed across his visage repeatedly, coating the faux lenses of his glasses and mixing with his hair. He even managed to catch some in his mouth, which he made sure he showed her pooled on his tongue before swallowing it.

He panted heavily as he stood, noting with great pleasure that she wasn’t going flaccid. “Did I do a good job?” he asked, rubbing his swollen stomach.

“That was... wow,” she purred, flopping back onto the bed. Though Button had begun to go soft from lack of attention and oxygen, seeing that pink penile pillar laying between her breasts, still fairly rigid, was more than enough to keep him excited. “I’ve never had anyone take it before.”

“There’s still more, too,” he said. Bending over slightly, he guided his hands beneath his skirt. Down came his panties, and he looked longingly at his prize. He’d been a good little toy; he made his partner feel good, so now he was going to be rewarded. That’s how the sessions worked. “Would you like to see?”

Sweetie watched uncomfortably as he climbed back over her, positioning himself above her waist. “Button, stop.” His back was to her, so it came as some surprise when she smacked his hand away as he reached down between his legs to grab her penis. “Button! No!”

He froze at the ice in her tone. “But... I made you feel good,” he whispered dejectedly. “Did I do something wrong?”

“It’s nothing personal.” She grabbed him with her magic and sat him beside her on the bed. Her horn lit up again, and he could feel the semen peel itself out of his fur and hair. A large glob of cum floated away from him in a cloud of shimmering green, only to deposit itself in an empty glass by Silver Spoon’s bedside. “You’re... I don’t usually swing that way, and I just can’t do anal, Button.” She shook her head, brushing a stray lock of his hair out of his face. “I’ve never been comfortable receiving it, and it’s honestly kinda gross.”

As if to punctuate her point, her member slowly shrank away, as if to hide from the idea. He watched in awe as it receded back into her vulva. It just pulled itself back in as though it were completely normal for something of that size to hide out where Sweetie’s clit should have been.

“Oh.” He looked away, his face beginning to redden beneath his chocolate fur. I’ve never been unable to complete a session before. Somehow, it was hard for him to accept. All of his sessions with Diamond Tiara and Silver Spoon had ended with his cheeks being spread; so long as he did what they asked, they always made sure he came too. But Sweetie couldn’t press past her own barriers, and he had nothing he could offer her otherwise. “I’m not sexy enough, then? I’ve... failed?” A sniffle escaped him. “If I was a real mare... Oh, they’re going to be so upset with me!” A shiver wracked his body.

“Button, it’s okay,” she whispered, pulling him into her bust. Her fingers snaked through his mane as she tried to soothe him. “I never should have agreed to this to begin with. As soon as I found out it was you, I should have walked right back out that door.” Something warm trickled down her chest fur, and she knew instantly that he was crying now. “Shh, it’s okay.” Unsure of the right thing to say, she quietly added, “You’re a good girl.”

It was some time before Button cried himself to sleep. She was there with him the entire time, just holding him and comforting him. The only time she left him alone was to put her dress back on and slide his panties back up his legs after he passed out. Even then, her eyes rarely left him.

There was just something entirely off about her childhood friend. When they were little, she couldn’t get him to talk about anything other than video games, even though at the time it was a shared interest. His fixation was so bad that it was like he never even noticed her at all during puberty. Now, not only was he an apparent sex addict, but his fixation was now entirely based on making his partners—or rather, Diamond Tiara and Silver Spoon—feel good. It was almost as if he had developed a psychological dependency on ‘feeling sexy’ and pleasing others—an addiction, even.

The implications of that alone were rather frightening, especially having seen him so distraught at having not having received anal—or ‘completing the scene’, as Silver Spoon often called it. And agreeing to go on camera for it? What was even going on inside his head? To say that his state of mind was worrisome would have been a colossal understatement.

For that matter, what was going through their heads when they came up with this whole scenario? They’d lied to her about her partner. She wasn’t at all attracted to stallions, and yet they did this—set her up with a sissy colt. Sure, it was sort of exciting having him go down on her, and it helped that it was somepony she at least knew, but still!

Worse, it was nearly impossible for them not to realize that he seemed to get off on anal, and she knew that they knew—because she’d told them many times—that anal was not in her comfort zone. It was downright cruel to do that to him. I thought they’d gotten over being evil little fillies, but I guess I was mistaken! Both issues left her blood seething to the point that she barely knew which she should be angrier over.

“I’m telling you, they’ve been pretty quiet for a while,” she heard Silver Spoon say as the door cracked open. “Besides, I guarantee that she didn’t—”

Sweetie clenched her fists as the two strode in the door. “What did you two do to him?” she snarled, praying desperately that she wouldn’t throw something across the room. “Are you both insane?”

Diamond Tiara, who had been moving to shut off the camera, paused mid-step at Sweetie Belle’s accusation. “What do you mean?” she asked in an almost mocking tone. “Didn’t you have fun with your new girlfriend?”

That snide BITCH! “What in the name of all that is good did you two do to his head?” she bellowed. A bright green flash filled the room and in the blink of an eye, everything in Diamond’s armoire came flying out onto the floor. “Can’t you see that there’s something seriously wrong with him? He’s practically conditioned to being your butt slut and being so eager to please that when I wouldn’t fuck him in the ass, he started to have a panic attack. His mind is all over the place!”

“Sweetie, he’s fine!” Silver Spoon interjected too quickly. “Sure, the first time was kinda-sorta blackmail, but everything after that was consensual. Just today he manipulated us for a cut from the videos. Ask him when he wakes up!”

Sweetie glared at Silver, but Diamond spoke before she could lash out verbally. “Aren’t you being a bit ungrateful?” She snorted, pressing a button on the camera. “After all we’ve done for you?”

That was it. “I thought that besides starting your own little porno empire here at the institute, you two had grown up since you were little fillies.” Her horn lit once more as she floated Button onto her back, securing his arms around her neck before grabbing his legs under her armpits. “When you both found out about my penis, you coerced me into starring in a video. In the bathroom where you caught me masturbating,” she snarled. “Whatever you did to him, it’s even worse than that.” She stomped toward the door.

“We are done with you both; you’re toxic,” she hissed. “Don’t even try to blackmail us or manipulate me into staying out of this, either. I’ve got enough dirt to get you both expelled, even if I end up going too.” Her horn lit up one last time as the door swung open. “He needs help, and it’s not something either of you seem willing to ensure he gets. Stay away from him.”

Author's Notes:

So it came to pass that we see how fucked up Button has become over his time with DT and SS. But what's this? Sweetie Belle to the rescue? Will she hurt him, or will she heal him? Only time [and/or loose-lipped authors] will tell.

Pre-read by Kaidan and BakmahGenesis.
Edit by ReFro to come.