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There was a certain level of cruelty to being under Theo's control. Just the very thought of the zebra had Oliver continually aroused. The spare dildo he'd been given had helped a little, more to scratch the itch than anything. The otter couldn't exactly toy with himself in his dorm, except maybe in the shower but his roommate would surely hear him.

Breathing techniques helped. The otter did a little research in his freetime, finding meditative methods to keep his arousal at bay. They worked between classes, and during swim practice with the rest of the lithe masculine bodies surrounding him. But in the presence of his master, Oliver's cage felt all the tighter. There he stood, waiting in the doorway of the pool and waving over to the otter as he got out from his lap. Just in time for practice to end. Feeling a tug on his heartstrings, Oliver made his way over to the zebra, leaving wet footprints across the floor.

"Morning...master," He whispered, struggling to suppress his smile at the title. Theo's small smile had him giddy, yet anxious. Why was he here this early? Probably for track, judging by the short running shorts and white jersey. Oliver wondered if those pants would tear at restraining Theo's erection.

"Morning, Olive. Have a good practice?" The otter felt butterflies in his stomach at the nickname. At first, he just found it rather odd, not really considering himself a girl even in play. But now, he loved the way he said his slave name. The name that branded him as the zebra's personal little sissy, fuckhole, or even urinal. He'd happily be the zebra's cute girl, and Theo preferred his girls having nice locked clits. With a nod, Theo smiled. "You must be thirsty."

"Well, I have a water bottle so-" Theo shoved a clear bottle of water into his hands before the otter could finish. Duct tape had been wrapped where the label was, with the name 'Olive' written in all caps by a marker. The bottle was cold, far colder than the room temperature bottle he'd left out. The zebra's lips reached Oliver's ears, and he whispered in a cool and confident voice, "It's a special drink I had prepped last night. I've been making sure to stay very hydrated for my personal urinal."

He blinked, letting the cogs in his head rotate as the bottle of 'water' rested in his hands. Oliver's maw felt dry all of a sudden, his heart beating in his ears. Peering over his shoulder, the otter saw his teammates still around the pool. Some were heading to the locker room, others were doing final laps or just joking with each other at the door. This wouldn't be his first time drinking the zebra's piss, but in front of everyone?

"Well, you're thirsty, aren't you?" Theo asked, gently tapping the bottle. "Bottoms up, Olive." Taking a deep breath, Oliver took one last look around the pool. The scent of chlorine was still strong as he twisted the cap off, ready to be replaced by the foul odor of his master's excess. Pressing it against his lips, he guzzled the salty but watered down taste of his master. His teammates from afar were watching, never thinking he was drinking anything more than just a regular water bottle.

The damn cage had his failed erection almost hurting at the humiliation. Taking breaths between each sip, the otter closed his eyes and finished the bottle. "Well, someone was very thirsty," Theo chuckled, taking the empty bottle back. "I would have figured you'd be hydrated from the pool."

"We can't...you know what chlorine is, right?" Oliver blinked.

Theo smiled, "Course I know. I was just a joke. Like that one meme of an olympic swimmer pouring water over his head when he's still in the pool."

"That's more to keep the suit or cap in place?" Oliver explained, earning a confused look from his master. "N-Nevermind...is that all you came here for, master?"

"Do I really need a reason to visit my precious Olive at practice?" He teased. Oliver's blush had the zebra smugly smiling. "But there is one this time. I'd like you to be at my apartment at three. We have a date tonight. If you are up for it anyway."

***

Three seemed rather early for a date night. More like a mid-afternoon date anyway. Still, a date was a date, and Oliver made an effort to look good for it. Brushing his hair, picking out a tight black shirt and short jeans to show off his legs. He was certain Theo would have something extra for him to wear, so the otter went freeballing on his way to the apartment. Well, as free as his balls could be with the ring around their base.

Lucy answered the door, wearing her classic skirt and midsection revealing outfit. "Well, don't you look fun," She said, eyeing down the otter's outfit.

"Well, I got to for my date tonight."

"Oh, Theo has told me all about tonight. He's very excited." Lucy turned her head back, "Isn't that right, master?!"

"You two can come on in ya know!" Theo shouted. Lucy let Oliver in, leading the otter down to the front room where Theo was waiting. He still dressed casually, sporting little more than his grey tee and jeans. The zebra could be dressed like a clown and Oliver would still feel submissive toward him, though he couldn't suppress his laughter if he did. "Well, don't you look nice," Theo said, standing up to inspect the otter from a distance. "Strip."

Blinking at the command, he didn't start until Lucy was halfway free of her clothes. Soon the two submissives were standing naked before the resting zebra, with their arms behind themselves, and their chests puffed out. Theo twirled his index finger, signaling his slaves to give him a little spin for his viewing pleasure. "Very nice. Lucy, give Olive here a shower. We need him nice and clean before the date tonight."

A shower? "Yes, Master." Lucy bowed, pushing the confused otter across the room to the nearest full bathroom. Turning the shower on, the two stood naked as steam filled out the room. Lucy winked to the blushing otter as she stepped into the stream. "Well? What are you waiting for, cutie?"

"I guess a little explanation?" Oliver said, still stepping into the shower and letting the water soak into his fur. He figured they were just going on a date, why the duo shower? Lucy smiled, already spurting fur shampoo into her hands and lathering up against Oliver's body.

"Theo is planning on a very special date, and good girls and bois need to be presentable for their master." Her hands drifted across his body, flat chest bracing against the otter's back as the sudsy fingers crawled across his cage and crotch. The cascade of water did little to hide Oliver's brief gasps and delightful whimpers to the lion's touch. Her long black headfur drooped down his chest as she whispered into his ears, "I'm a little jealous of your date tonight. You're such a lucky slave."

She toyed with him throughout the wash, massaging his chest and nipples while rubbing in the shampoo and conditioner. Lucy even thrusted her caged clitty against his ass, grinding into him with a subtle growl that shivered his core. A knock on the door interrupted them, "I know you're horny, Lucy, but I do need to get him dressed."

"You're free to come in, Master. We're almost done."

"And interrupt my lovelies in the shower? What sort of gentleman would I be?"

Turning the faucet off, Lucy pulled Oliver out and dried him off with a nearby towel. A pink one, which didn't surprise the otter given Lucy's tastes. She brushed down his fur carefully, avoiding causing any knots or bundles to mix in with his fur. With a snicker, she pushed him out of the bathroom and into the waiting arms of the toned zebra. "Well, don't you look lovely," Theo mused, earning timid blush. Next he knew, Theo pushed him back into the bathroom where a small dildo waited upon a stool before the mirror. Cold and slimy fingers pressed against his butt, "Now, I want you to relax for this next part. Can you do that for me?"

Taking a deep breath, Oliver nodded and eased himself against the standing dildo. The plastic nubs pressed against his insides, rubbing right up at his prostate as he sat down. Theo gently pulled the otter's arms back and cuffed him. Before Oliver could voice his concerns, the zebra braced a finger to his lips. "Shh. Just making this a little more fun for you, my little humiliation whore."

Next came a large fold out kit from underneath the sink. Inside were various brushes, tubes of lipstick, sponges, anything one would find in a makeup kit. "Wait...what's that for?" He asked, though Oliver had a sneaking suspicion that he already knew. Lucy giggled from behind, but said nothing as she stepped out to get dressed. Theo grabbed some purple lipstick and puckered the otter's lips.

"Why, it's to make you beautiful tonight, Olive." Theo worked with a perfect blend of care and speed, applying makeup without error across the otter's face. Oliver blinked twice at his reflection when finished, thirty seconds apart as he realized it was him staring back. Theo crossed his arms in confidence, with Lucy cuddling up next to him.

"I love watching you work," She whispered, pawing at his crotch, "One of these days you'll need to do me again."

"Then we'll need to do another date night," Theo said, casually pulling Oliver off the fake cock and unlocking his arms. No time to rest, the otter was pushed toward the bed. A red thong and bra waited for him, laying next to a black tight dress with sheer puff sleeves. "I was tempted to get you heels, but you need to practice in those," The zebra whispered, grabbing the thong and tapping Oliver's legs to step up. With a delighted shudder, he complied with Theo's command, trying carefully not to bite his lip as those strong hands pulled the clothes over him. Gone was the twink Oliver, left in place by the owned sissy Olive awaiting their master's command.

After the matching blocked heel sandals with little locks, Theo bent him over and firmly handled his ass. "I'm tempted to just skip our date tonight," He whispered in a low growl, "Just take you right here, right now."

'Then why don't you?" Olive asked, smirking as his master pulled down the panties. He moaned as a cool gel braced against his pucker, spreading out ready for anything.

"Reservations are expensive," Theo said with a smirk. With one hand tight on his ass, Theo slowly pushed a plug against the pert little hole. Wider than the dildo he'd been gifted, Olive's fingers dug into the bed as he braced for the toy that filled him up. "Good girl," Theo whispered, pulling the panties back over the inserted plug. "Lucy, help Olive into her wig. I need to get dressed."

Decked out in a raven colored bob cut wig, the otter waited diligently at the couch beside Lucy, who snickered in delight at her nervous sister. Theo carried an aura with him as he stepped out from his room in a full dark grey two piece suit, finishing his cufflinks as he carried his sports jacket over his shoulder and let a pink tie wafted freely. Like he was some kind of young fortune 500 CEO, and Olive was his personal date. "Never expected a pink tie, if I'm being honest, sir."

Theo smiled, "Well, pink used to be a masculine color. But beyond that, I don't care what onlookers think of my color choices. Not anymore." Pulling him up, Theo wrapped him close to his body and led the otter in drag toward the door. "We might be home late tonight, Lucy. Do try to keep the place clean."

"But of course, master." Lucy bowed obediently to the couple leaving, "Have a pleasant evening." Of that, Olive had very little doubt. Though fear crept in his mind at the thought of everyone seeing him in drag. Fear that was constant, but also continually batted away by the mere presence of the master holding him. If not for the cage, Olive's erection would surely give it all away.

***

Aside from the K-pop music that Theo blasted on the ride, there wasn't too much to talk about. Oliver could have brought up the choice of clothing, but the otter had too much fun in the anticipation of it all. And by the long drive and shrinking city lights, he assumed Theo had a plan to keep them safe from familiar eyes.

"So...why the K-pop?" He asked, eyes set on the confident zebra driving them.

He shrugged. "I think it's cute," He explained, "I mean, the culture behind it is pretty worrisome, but it doesn't stop me from having a bit of a dark fantasy of managing a few cute guys in drag singing k-pop songs."

Despite the zebra's shameful sigh, the otter laughed. "Oh really? I would have figured it'd be more of the powerful CEO type, with cute guys working as your personal staff." Oliver rested his hand across Theo's thigh, "I could see you having a lovely secretary between your legs during calls, working your shaft while you play with his key."

"That sounds like your fantasy...and a very enjoyable one at that," Theo said, cracking a smile as they turned into a parking garage. Stepping out of the car, they locked their elbows with each other and casually strode through the cement building where Theo's hooves echoed across the pavement, to the sidewalks outside. As soon as the city air hit his nose, Oliver clung tight to his date like a lost child. Even so far away from campus, in the age of the internet anyone could snap a picture and see through his disguise.

"Take it easy," Theo ordered, "Or you're gonna mess up the wig."

"I can't help it. I've never been in drag before."

Theo rolled his eyes, "Ugh, hate that word. Drag. Your dress isn't even long enough to fit the etymology."

"Well I'm sorry if I don't care about the origins of the term...master," Oliver said, ending his snippy rant with a bowed head and a whisper. His eyes darted back and forth, taking in every little glimpse at those watching them. From the wolf in a grey hoodie, to the gaggle of girls walking past and no doubt checking out his owner, Oliver could only steady his breath at the fear of discovery.

The plug didn't help, forcing him to walk slowly despite Theo claiming it wouldn't fall out. For once, Oliver was happy for his naturally thick otter tail. Onlookers would have to be actively looking to find the plug he was so bashful about. "We're here," his master whispered, stopping at the steps of a building lodged between two thick offices. In bright silver letters, the name 'The Silver Maple' etched over the doorway, with the eye taking the form of a maple tree.

Oliver blinked, "This looks fancy."

"It is."

"And expensive."

Theo nodded, "Those two are common. We did get dressed for something fancy."

"How...how can you afford this?" Oliver asked, "I mean, you're a college kid."

"How else can I afford having an apartment to myself with no job? I have a well off mother who will call me tomorrow in frustration over how much I spent."

"Oh..." His fingers dug into the suit as guilt drilled into him, "You didn't have to...especially if she's-"

Theo gently lifted the otter's chin, "Olive, I want to. My mother would understand completely."

Inside they were greeted by a sharp fox dressed in a sharper suit who guided them toward a table near the back. Looking through the menu, Oliver suddenly felt an extra wave of guilt for not bringing his wallet with him. It wasn't as though Theo gave him a purse to put his belongings in, nor did he ask. "There's no way I can pay you back for these," He muttered, eyeing the zebra currently casually looking through his.

"You don't have to. I'm paying entirely."

"But shouldn't I pay for-"

"Olive, as much as I admire your sense of fairness, you're already paying with your looks. Besides, in my experience with these kinds of relationships, the dominant pays for extravagance. It's not like I'm a temp you hired or anything. Pick what you want and I'll spot the price."

Even with the permission, his guilt lingered with every option. The cheapest dish being just around fifty, and only an appetizer. A ferret in a fitting black and white suit with a tie stepped over with a pen and handheld notebook. "Good evening, and welcome to the Silver Maple. My name is Frederick and I shall be your waiter this evening. May I start you off with something to drink?"

"We already know what we want, actually," Theo said, much to Oliver's surprise as he put down the menu. "Olive, why don't you go first?"

"I-" The plug inside him buzzed to life as he spoke, cutting him off in sudden shock. Face burning, he gripped the table as it stopped and slowed his breathing. "S-Sorry. I'm n-" It buzzed again, stronger against his prostate. Each attempt to speak was met with a new vibration. The otter eyed his date, taking note of the hands hidden from view and the nonchalant smile.

Poor Frederick just watched with his pen at the paper. After a minute, Theo stepped in as the buzz reached a low but continuous vibration. "I think Olive here will have the Liguine with clams, for the main course. I'll have the Ratatouille, and for drinks we'll take your choice of red wine. No appetizers, please."

Taking notes, the ferret bowed and took their menus, "But of course. I shall be back shortly with bread." Olive gave Theo a frustrated and more than a little aroused glare as the buzz stopped. The zebra responded with a small smile and a sip from the water he swirled in the glass chalice.

"You could have told me."

"Told you what?"

"The..." Oliver's eyes shifted. Seeing a nearby couple, the otter lowered his head and whispered, "The vibrations. A plug in public is hard enough..." Not that he wanted it removed. The thought of getting caught made his cage, and Theo's grip on his masculinity all the more sensually frustrating.

"Well, if it helps, the plug is set on a timer. Only I don't know when it's going to go off. Also I hope you don't mind clams, I figured you might like them but I don't want to sound speciest."

"Clams are fine. My mother preferred cooking them," He said, his eyes wary of Theo. Oliver carefully watched the zebra whenever his plug went off. He always had a hand underneath the table, save for when they ate. But even with both hands revealed, Oliver couldn't believe the buzzings were random. There came up whenever the waiter came by, or even when someone else passed them.

After dinner ended and Theo picked up the check, his locked arms with Oliver and they strolled down the streets. "So, what's next on our D-date?" He moaned, the vibrator buzzing deep again, teasing his poor prostate.

"Call me uncreative, but I got us movie tickets. Mainly for a boring old period piece."

"Why that kind of film?"

"Well, do you honestly expect to be watching it much?"

Poised and excited, Oliver clung close to his date as they turned their tickets in and moved inside the theater. His mind went wild with perverted ideas at the sight of each empty row, with small bits of fear clinging to him at the thought of people coming up. Theo directed them to a corner seat in the upper rows, one of the worst spots to enjoy a movie.

Thankfully, that wasn't their goal. Smiling softly as the lights dimmed, Oliver leaned into his date and brushed his hand against the burgeoning crotch of his master. "Someone's an excited little slut," Theo cooed, unzipping his pants to let his rod flop out. "Why don't you go and give this a little attention? On your knees."

The order filled him with excitement, happily bringing the otter down to the swept theater floors and kneeling before the sitting zebra. The fat and thick equine cock hung before him, its musk heavy and virile. Dragging his tongue across its pulsing flesh, Oliver could only imagine it inside him. The plug buzzed again, pre dripping from his cage as he took both hands and held the cock steady for worship.

"I guess clams weren't enough," giggled a familiar voice, "Though maybe she just wants sausage." Turning his head, Oliver's eyes grew wide at the sight of Lucy. The lion sissy dressed in a short and tight emerald green dress, with mascara over her eyes and raven black lipstick, complimenting her straight headfur. With a toothy grin, she fondled a remote in her hand, pressing a button and sending the plug inside the otter into a vibrating pulse.

"Can you blame her? She couldn't focus with you tormenting her from afar." Theo slipped a finger under her black choker, pulling the lion in for a heavy kiss. Their tongues danced between their maws, a dazzling display that made Theo all the harder and Oliver's cage all the more cruel. "I didn't say stop, slave," his master said in a hushed but determined tone, quickly grabbing Oliver by the back of his head and pushing his nose into the zebra's crotch. "Worship it."

With building pleasure, the otter took a heavy breath. Sucking in all of Theo's dominant scent before lathering his tongue against the virile meat. His master's teeth softly bit into Lucy's maw, hand slipping past her tight dress to fondle the dangling cage. Her moans were music, record scratches on the otter's own desire as he worked for Theo's attention. Humiliation crept down his spine the more they ignored him, yet his cage felt painfully tight at the display.

Wrapping his lips around the flat head, Oliver slipped what he could of his master's girth inside him. How Lucy could take such a beast he couldn't understand, struggling to even get a third of it down his throat. What he couldn't take, Oliver wrapped his hands around and pumped, edging his master to the brink and tasting his pre against his tongue. "That's it..." He moaned, "That's it...just a little..." With a grunt, he lurched forward. His seed spurted quickly, overwhelming Olive. Fearing to drown, the otter pulled off and winced as strands splattered across his face and wig.

"Well, don't you look fitting?" Lucy giggled, wrapping her arms around Theo's neck as she eyed the drenched otter, "Like the pretty little whore."

"Lucy, be nice to the slut," Theo said, wiping Olive's face with a napkin, "And put your back up against the railing, ass to the floor. Now." The lion followed without complaint, smiling sultry in her position. Pulling him up, Theo pushed Oliver against the railing. Without a command, Lucy lathered her tongue against his dangling cage as his master pulled the buttplug in and out, steadily fucking him throughout the process.

Leftover seed from his face dripped to the carpeted floor under the railing, forming a small stain that Oliver hoped the stuff would mistake for something else. Assailed from both sides, his moans and whimpers echoed across the theater walls without care. They could be caught at any moment, the fear kick-starting his heart. Gritting his teeth and tightening his fingers around the railing, a quick spurt escaped his cage and drenched the inside of the lion sissy's maw.

The sheer shock of it all would have sent him tumbling over if not for Theo's quick grip. "Woah there. Christ, that's a bit too close." The zebra pulled him back, landing safety in the seat behind as they cuddled up with each other. Deep breaths shaking his core, Oliver clutched Theo's suit jacket tight as he coiled up in his master's lap.

"Looks like someone had fun," Lucy said, licking off some stray seed from her lips. "Hmm...we'll need to add some pineapple to her diet if we can help it. If you're gonna have me do that again I mean."

"Since when do you give orders?" Theo jested, holding the otter tight. Pulling off the wig, the zebra gently tussled through Oliver's hair. "There, there, Olive. Did you like that?" What kind of question was that? Did he like being ignored? To be used as a personal plaything between the two lovers and then doubleteamed in a public place, potentially caught or discovered on camera? Of course he loved it!

He nodded, smiling weakly as he nuzzled up against the pectoral muscles underneath the collared shirt. Oliver hadn't been on many dates, but this one had been by far the best.