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Standing at the entrance to Tiffany's apartment building, Felix expected something more expensive. While the leopard had his fair share of 'fun' looking at living expenses in the city, his excuse was that he waited tables at a strip club while Ein worked as a phone tech. They didn't have much money lying around, hence the small two-person apartment.

But Tiffany was a rockstar. He'd listened to her band's music so it's not like she'd been lying to him. Sure, they only had one album out and were rising, but it was enough for the shark to try to hide her identity when they went on their date. The apartment complex he entered seemed too normal for a rockstar. Like something that belonged to middle-income workers.

Sending a text to notify her, Felix waited outside the building. Leaning against a nearby tree while pondering his choice of clothing. While keeping the baggy jeans, he changed out his overly large shirt for something more his size and carrying a peace logo. An old hand-me-down from his dad's hippie days, which, come to think of it, never really ended.

Either way, it wasn't baggy. Rather, it stuck closer to his fur than he liked, and had caused more than a few heads to turn when he got out of the rideshare. He'd been thankful the driver was a quiet one this time.

His tail flicked the air as the door opened. The most butch hyena Felix had ever seen walked out, with red-tipped dreadlocks and a leather vest over her grey shirt, and a studded belt holding up her shredded jeans. He gulped as she walked by, only to find his head sinking into his neck when she turned to him.

"You Felix?" she asked, her nose ring bouncing as she spoke. She smiled as he nodded and put out her hand, "Names Vicky, I'm Tiff's roommate,"

He blinked, recalling the names of the band members in his head. Vicky Jeager, the head singer of the band stood towering over him. Nowhere near as bulky as Tiffany, but still looking stronger than Felix. He shook her hand, "N-nice to meet you. Is she expecting me?"

"Yeah," Vicky pointed to the top floor, "Elevator's busted so you're gonna need to walk. She's not gonna come down."

"Why? She's not mad, is she?"

Vicky gave a deep gutted heckle that made the fur along his spine stand on end, "Nah, she's just practicing with that fancy electric drumset she bought. Tiff tries to distract herself when nervous."

Tiffany was nervous? Felix stared up to the top floor, trying to imagine the amazonian shark being nervous. Sure, she'd expressed fear about them being crowded when together, but the shark had been nothing but a beacon of confidence. "Do you guys have like, a show or something coming up?"

Vicky shook her head, "Oh Tiff, you sure know how to pick em," she sighed under her breath as she headed to the door. Holding it open, the hyena waved him on, "We're room 311. You're gonna need to knock hard to get her attention. Her headphones are good."

A few flights of stairs later, and Felix found himself at the right room. Taking a deep breath and mentally swatting the anxiety devil away, he knocked on the door.

Then again.

Then a third time, harder as he remembered Vicky's suggestion.

Tiffany ripped open the door, dressed in only blue striped boxers and a matching bra while a pair of headphones hung from her neck. Bearing her fangs, she lashed out, "Can't you see I'm-" only to stop midsentence at the sight of Felix and his tail between his legs. "F-Felix?" she looked to the right, probably at some clock, "Shit, it's that time..." taking a deep breath and blushing, she motioned him in, "Sorry, I was in the middle of practice and I lost track."

Swallowing his own fears, Felix stepped on in, "S-sorry, you weren't answering your texts and your roommate said I should just knock."

"You met Vicky?" she asked, her smiling dropping after asking, "Did she...um...she didn't tell you anything, did she?"

"Apart from the knocking, no," he said, shaking his head. The leopard took a moment to peek around the apartment. It was definitely bigger than his and Ein's, but that's a low bar to beat. Their living area had enough space that a big herm like Tiffany didn't need to squeeze through, though with the discarded clothes and pizza boxes she had to step carefully.

"Sorry for the mess," she said, scratching her head, "Vicky said she'd clean this morning and I guess I just got too lost in my machine to notice."

"I thought you had practice yesterday?" he asked.

"I did," she said, "But I got this electronic drum set with my first paycheck to practice more," the shark explained, pointing to the mock drum set with thin black panels where the actual drums should be, "Been using it a lot when I'm not working out. It helps when I'm stressed."

"What are you stressed about? Also, should I take off my shoes?"

"Yeah, just put them on the towel behind the door," she said, pointing towards said towel as the door closed behind them, "And well..." her eyes shifted, "I listened to some recordings for new songs and I felt my drumming got sloppy. We need these ready for showing by next month, and I'm just feeling behind."

Felix believed her but felt something else had Tiffany nervous. Vicky didn't seem anxious upon meeting him, and while it's entirely possible that the hyena dealt with things differently, it's all he had to go on before asking, "Is there anything else? I think you sound good."

The shark chuckled nervously, "Anything else? N-no, I don't...is that a new shirt? It looks nice on you." she said. Something was off. The normally confident shark was deflecting like him on a bad day.

Shaking his head, "No, it's my dad's. I don't wear it cause...well it clings too close. But yeah, I listened to some of your music, and I think you're good."

"Are you saying that to be nice, or saying that because you're a fan now?" she asked, the concern plastered on her face. He froze at the question, remembering how Tiffany felt about 'dating' fans. Felix didn't want to scare her off, becoming some crazed fanboy who got off sleeping with the band. He met Tiffany first after all, not RockJaws.

"Not as a fan, just someone who thought it sounded nice," he said, trying to put it carefully, "But it's not just the music that's stressing you out, is it, Tiff?"

"I didn't-" he placed a finger to her lips.

"Tiff, please, you listen to my struggles. Let me help."

Blushing, the shark nodded and, with a sigh, took a seat. Patting her lap to beckon him over. Smiling, the leopard took comfort resting against her strong legs and cradling himself to her bosom. With only the two of them there, he had less shame to feel about being in such a girly position with her. Knowing full well that she didn't think him a joke for doing it.

"So," she pushed a hand through his purple headfur, "I'm actually worried about...sex," Tiffany gulped, "Last night, after our little phone play, I made a stop to a particular store and got something because I couldn't stop listening to my dick. I 'really' want to see you in it, but I'm afraid you'll be mad and it'd kill the mood. I know I could ask later but..." sharp fangs bit into her bottom lip, years of control were all that stopped her from breaking her own skin, "Well...I can't help but think you'd be cute in it."

The anxiety devil wrapped a noose around his heart. Felix had an idea where this was going, it's something that happened too often in his life for him not to notice the signs. "It's...it's girly is it?" he asked, begging for it to be wrong despite the blush under his fur. Her nod sealed it, letting the devil on his shoulder laugh maniacally as it told him that even she saw him as a girl over a man.

And he didn't run. There was no depressing acceptance or cold anger building beneath his skin. Nestled in her arms, the leopard felt comfortable with the idea of being girly for her. But he couldn't admit it, hanging tight to her as the minutes passed by.

"You don't need to wear it," she said, "I was just, really horny and I make dumb decisions sometimes when I am. And-"

"Do you see me as a girl or a boy?" he asked.

She blinked but didn't ask for him to repeat. Taking a deep breath, she nuzzled him closer against her breasts within those strong arms and answered, "I see you are a cute boy, but I'm worried you're letting what your body isn't distract you from what your body is. So...I figured today I'd explore it with you."

"And the...things?"

"Well...I have a fondness for bois in lingerie," she said, "Though we really don't need to if you're not-"

"Show me," he asked, staring up into her shocked amber eyes with blush burgeoning across her grey cheeks, "Y-you bought it for me...so I might as well see it. It's been a while since anyone got me a gift," Felix said, blushing and avoiding eye contact. Without warning, Tiffany hurled the leopard over her shoulder and carried him across the apartment, deftly avoiding hitting the pink cat's head against any walls despite her hasty speed. Next, he felt the springs of her bed as she tossed him atop it, letting Felix see the rest of her room while she hurried to her closet.

Marginally bigger than his, Tiffany adorned hers with a wildly different setup. Rather than a desktop computer, the shark had a large laptop on a grey desk in one corner. In the other were a set of dumbbells and an exercise mat, lacking the cobwebs of disuse the leopard had imagined when it came to a home gym. It became clear why she didn't have her drum set in her room, being more preferable to listen to the shark hit a muted drum than work out in the open. A large mirror stood across from him, reflecting back a nervous leopard to Felix.

Tiffany came back with a pair of tights, a pair of black panties, and a matching bra, "S-strip," she ordered. Felix wasn't sure who was blushing harder as he removed his clothes, getting himself to stand naked before his girlfriend with nothing but the cage around his cock. He hadn't even noticed it today until now, where his cock strained against the walls and made his barbs go nuts. Breathing heavily, he averted his gaze from her. Tiffany didn't allow it, holding his chin and kissing him with a passion he thought was reserved for cheesy romance films.

"Good boi," she whispered, pushing him to the bed and lifting his legs. Grabbing the black tights, she lifted his legs and slowly pulled them up his legs. He didn't even try to fight back, not that the leopard could do anything against the musclebound shark herm if he wanted. She'd never been so forceful, and it made him quiver in her grip as she pulled the panties up his crotch and over his caged cock.

"Arms up," she demanded, swooping around behind him and pulling the bra over his chest. Grunting as the soft cotton pressed against his nipples, the leopard fell back into Tiffany's breasts. Showing her toothy grin, she looked down at him and said, "You look beautiful, cutie."

He wasn't sure what to feel. Aroused was a start, but shame for dressing up in these clothes also swelled under him. Pushing him to his feet, Tiffany stood tall behind him as she motioned him into the mirror, "Don't you think so?"

A girl stared back at him, frowning in pity he knew so well, "I...I look like a girl." Tears formed in his eyes, "People are right..."

"No, they're not," Tiffany cooed, "You look like a boy dressed in girl's lingerie. A sexy boy at that."

"But..." he muttered, unable to look away, "But I look to femme,"

"There's no such thing,"

"You don't-"

"Felix," she interrupted, wrapping her arms around him, "Do you think of yourself as a girl?"

"No. Of course not!" he cried out.

"Then you're not a girl," she whispered, lips crawling up his neck with kisses, "Don't let others dictate who you're supposed to be, only you can decide that. And, if it helps," she reached down, gently squeezing his cage through the panties, "I still see you as a boy. A sexy boy dressing up for his girlfriend because it makes her happy. I know a lot of so-called men who wouldn't do anything like that to make their lovers happy. To me, you're more manly than they could ever hope to be. Because you're willing to push through."

Moaning at her touch, cock straining, and barbs sending electricity throughout his body, Felix found himself melting to the shark. Her cock pressed against him. Blocked off by the clothing each wore. She wanted to fuck him, it didn't take a genius to notice it. The devil on his shoulders screamed at him, telling him he'd be losing everything he stood for if she let him while dressed like this.

But Tiffany wasn't some random jock with a cock at a party. She didn't humiliate him for his girly body. She teased him, sure. Groped and prodded him all over with those strong hands of hers, but never did the shark belittle him.

"So..." he smiled, "What's next? You gonna fuck me?"

"Like a prince," she giggled, "But only if you ask for it. Your butt is yours to give."

"Will you unlock me?"

She shook her head, "No. I don't want you thinking about your cock. There's more to pleasure than your cute rod and I want to show it all to you."

"Is that the only reason?"

Her trademark grin filled the reflection, "Maybe. Maybe it's punishment for stealing your roommate's toy without asking. Would you be ok with that?"

"If that leads to this kind of punishment...I might do it again."

Slapping his ass, the shark giggled and pushed him back to the bed, "Naughty boy." she said, pulling out a pair of cuffs and a blindfold from a nearby drawer, "Mistress is gonna make sure you feel extra sensitive for that."

"Mistress?" he returned her gaze with a cocky smile, "We're going with titles now?"

"Just in bed," she explained, leaning over him and locking those cuffs around his arms wrists behind him without losing eye contact, "I did tell you, I'm a kinky girl."

"No turning back, Mistress?" Felix asked, his vision shrouded in darkness as the blindfold came over him.

"Just say red if things get too scary. Otherwise, no, Felix," the bed shifted as she leaned over him, her sharp breath brushing against his nose, "You're mine."

Her tongue cut his answer off, pushing past the leopard's soft lips and exploring his mouth in conquest. One hand caressed the back of his head, and the other reached down to grope his sensitive balls and caged cock. Her breath, her warmth, pulsated through down his body while the arousal building from below shot up, missing in his chest in a vortex of butterflies.

He kept uttering her name softly as she broke away, next feeling her tongue brace against the cloth over his right nipple. "Focus on it," she whispered, stimulating his nipples with the saliva that moistened the bra, "Let it build. Let it burn inside you. Boys have more than just their precious cock," the shark cooed, letting go of his cage and tweaking his other nipple through the bra. Felix clamped down on his mouth to keep him from spouting that safeword. The sensation combined with her expertise scared him, shaking the leopard's body with new feelings. His mind screamed at him to stop her, arms struggling in their bindings on reflex. But he wanted her to keep going, to let her explore his helpless form and show him what she meant.

Pushing away the bra, Tiffany took his erect nipple into her mouth. Felix had seen her maw, the rows of sharp teeth that made even other predators cower. She could tear him apart easily, something the leopard lacked in basic strength alone. All that strength and she had the restraint to hold back as her hot breath bathed his nip.

"Sounds like someone who ran a mile already," she said, chuckling while he felt her hand softly brush his face, "You ready for the next step, love?"

Nodding, the cat scarcely noticed how heavy his breaths were, "Yes, Tiff."

Her bed frame creaked as she got off and back on again. His ears twitched at the sound of something spurting out of a bottle, and, quivering, his tail hid between his legs as she lifted them up and pulled his panties aside, "S-sorry, reflex." He said.

"It's ok, baby. I'll be gentle. Can you move it or do you want me to?"

"M-maybe we should flip me over. It might be easier."

"But I want to see your face," she cooed, "Can you move it for me? Please?"

Blush against his face, he did as she asked, whimpering as the cold lube braced against his anal ring, "Relax," she whispered gently, "Be a good boi and relax for me. You've already got two fingers in no problem."

Taking a deep breath, Felix focused on relaxing his ass while she toyed and prodded with it, lathering its outer ring and inner walls with lubricant. No insults or petty mockery bounced off his ears while she toyed with him. Just his mewling moans echoing through the room.

The bed shifted again as she pulled out. Her cockhead braced the entrance, all slimed up with lube, "I'm going in now. Tell me if I'm hurting you."

With a nod from him, she pushed. Felix's mouth lay agape but nothing slipped through as Tiffany plunged her large cock deeper into his ass. He wasn't a virgin down there, but his past experiences were always fast and heavy. More for the pleasure of the fucker than for him. But the shark pushed slow, letting each and every nerve in his ass respond in kind as she went deeper and deeper. His whimpers turned to whines as she passed the dildo from the night prior, and a few inches later she stopped. He could feel her breath over his face, the weight of her leaning above him.

"I'm all the way inside you," she said, sounding shocked and elated, "You didn't even try to mutter it. Such a good boy," Felix felt her lips against his yet again, her cock pulling out several inches before slowly thrusting back into him. She fucked him. Not the hard rampant pounding like in porn or past lovers, the kind he expected from bigger individuals. No, she gently fucked into his hole, letting his pleasure build while he was given the kiss of life.

Pleasure built up from across his body. His filled ass, her breasts against his chest, and the warmth of her breathing down his gullet. Everywhere except his cock burned with pleasure, whereas his caged rod scratched its barbs against its prison walls and begged for freedom. He felt so close to bursting, just with one wall in his way proving to be a final dam against the wave hitting him. It needed to break, it had to break. Why wouldn't it break? He was so close.

Tiffany grunted aloud and cradled his head, muffling as he felt her spurt deep inside his rectum. One spurt, then two, then he stopped counting with their rapid succession. Her sweat matted into his fur as she laid above him, squishing him without complaint from the leopard's part. Felix was more concerned with his pleasure dropping than any discomfort from her. So close, why did she give up so soon?

The bed creaked as she stood up, "Fuck...the sun's going down."

He blinked behind the blindfold. It was only a few hours past noon when he arrived. Had they been fucking for that long? He opened his mouth to speak, only to stop when her hands grabbed his cage. A click rattled through his ears, and like a thunderstorm, his cock bolted upright in her grip, "Got a little pre here, but doesn't look like I got you to cum, let alone milked you," she said, casually pumping his cock, "Guess that makes sense. It takes a while to cum through anal, but since you fucked yourself with a dildo last night I figured your body was accustomed to it."

"It's been a while," he said, "Never really fucked myself down there until you caged me. It's easier and less clean up to...to..." her mouth enveloped his cock. Fears of her sharp teeth combined with the warm and moist pleasure of her maw and tongue, making the leopard only harder as the shark blew him. Given his barbs, Felix wasn't used to someone's mouth pleasuring him down there. Combined with the days in chastity making him all the more sensitive in his tiny cock, and he screamed when the floodgates broke, hips thrusting into her mouth with each spurt.

Finally emptied, Felix let his head rest against the pillow. Tiffany crept up the bed, laying atop him and kissing him one final time. Too exhausted to stop her, the leopard first noted the last of his own cum on her tongue, before feeling the wad of it pushed down his throat and gullet. Maybe it was the lack of energy, or maybe Tiffany had him completely under her will, either way, he didn't fight back. Swallowing his own seed obediently for as long as Tiffany held him there.

"Good boi," she cooed, rolling over and pulling him in for spooning, "Did you like it?" the shark asked, pulling the blindfold off.

Felix nodded, staring at the sidewall as his back rested against her tits, "Yes, Mistress."

"You don't need to call me that right now, we're done."

"What if I like it?" he smirked.

Curling a finger through his hair, the shark returned his words with a soft laugh, "Well, then I'd just have to get used to it." She bumped her cock against his butt, "Say...I know this is a lot to ask, especially after fucking, but can we try having you in the cage longer?"

He thought about it, for a few seconds before asking, "This gonna turn into one of those relationships where at one point I never get the cage off?"

"Hmm...maybe. It doesn't have to be."

"It's just...I don't want to forget my cock. I have one, even if it's...small,"

She nuzzled against his hair, "I didn't forget today, cutie."

"If I came through my ass, would you have?"

"If you came through your ass, would you want a blowjob or would you be too tired?" she asked. Felix blinked, not sure of what to say.

"Look, just because you have a cute butt and look good in drag, doesn't mean you aren't a man to me. I just appreciate men who don't mind letting me play with their asses more.

"So if I said no to more chastity, we'd break this off?" he asked, concern filtering through his tone.

"Of course not. Just means we talk about other things to try. Relationships are two way after all."

Felix stared out into open space for a long time, silently thinking on the pros and cons of being in her cage. Though he didn't like admitting it to himself, he hadn't had an orgasm this strong in a long time, and was curious to have an analgasm provided by her.

"Sure," he whispered, "But I still get a spare key for emergencies."

"Of course, Felix," she whispered as her cock grew hard again, "I wouldn't have it any other way."