FSE

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Oliver bit his lip as he waited in the corner of the coffee shop. The chocolate hare had only arrived ten minutes ago, but with the combination of excitement and anxiety, it felt like he'd been there for hours. He checked his phone rapidly, trying to find an updated message from user LDaddy51. No matter how often he checked, the last message still showed.

Be there soon, cutie.

Oliver had first received a message from LDaddy three months ago after a usual dry spout through some of his fetish community sites. Given the bunny's pictures on his profile, it wasn't too uncommon for him to get messages, but they were usually either dick pics or demands. Being the attention whore he was, he sometimes found them entertaining but never pursued. That was until LDaddy messaged him. There was no dick pic, no demand to obey, just a simple comment on the cage he was wearing back then was too big.

Oliver remembered that cage well. It wasn't uncomfortable for the pictures he did, but he never felt like he could wear it in public under his clothes. He responded to LDaddy about it, and next he knew, they had been talking for a month and he bought a nice and pink cage online that better fit through LDaddy's measuring instructions. Wearing it now, he had no worries about it looking like a bulge to any onlookers.

They had kept messaging, with Oliver revealing that despite his pictures, he never really went far into crossdressing. It was more of a fantasy, but it grew stronger as time passed. Now a senior in college, he found himself more preoccupied with pictures than his studies. LDaddy had remarked, and to Oliver's arousal, shown, that he had experience in dealing with sissy's. Often remarking that some just need that special release. After a few video talk sessions, they agreed to meet up, with him booking a short flight down.

"Olive?"

The hare looked up to see a face he'd only seen through picture and the digital screen. An older raccoon man with a beer belly gut stood next to his table, dressed casually for the autumn weather in khakis and a collared button-up shirt. He wore a soothing smile across his face, one that put the hare's own anxiety at ease.

Until he spoke up, "Y-yes, that's me." he muttered, standing to give a handshake.

The raccoon responded with a hug, "It's great to finally meet you. I apologize for the delay, but they almost lost my luggage."

"Oh, it's no problem. I only just got here myself."

"Oh? Hoping to be fashionably late instead of actually late?"

Oliver shrugged, "Yeah, but it kinda backfired with you actually being late."

The raccoon laughed, "Well, I'm sure we can salvage that. You can call me Tom, by the way."

"Thanks. It's Oliver for me."

"Well then, Oliver, shall we get going?"

"Yes, let's."

***

The evening did not go as Oliver expected. It was mostly just talking, driving, and walking around. While Oliver tried to enjoy the conversation, it was just stuff he'd heard all before from people older than him. What do you plan on doing after college? What are you studying? Where do you want to live? Etc etc.

It's not as though Oliver expected to be taken to a hotel and fucked in the first thirty minutes of meeting Tom, but some teasing would be nice. He didn't even tease him during the movie they went to see, of which the theater was empty.

"Something wrong?" the old raccoon asked as they exited the theater.

"No, it's just. Well..."

Tom didn't let him finish, "It's not what you expected?"

Oliver nodded, "Don't take it the wrong way. I'm having fun, but it's just not what I was looking forward to, you know? Like, I didn't expect a regular date from a guy by the name LDaddy51."

The raccoon chuckled, "Well, it is that. Though do you want to know why I don't just take you to my hotel and fuck your faggot ass until your brain overloads?"

Stunned by the raccoon's phrasing, Oliver stared silently as Tom pulled out a small beaded necklace. It was almost like a dogtag necklace, except instead of tags, about five keys hung off it.

"Each key is to a cage I own. A cage that I have personally locked around each precious little sissy who submitted their freedom willingly to me. I have a harem, Olive. If I wanted to just stick my dick in a hole, then I could call one of them at any time and they'd come to me."

The hare gulped at the sight of the necklace, feeling his own cock strain in his cage, "T-then why come to see me?"

Tom came closer, his blue eyes staring down on the hare's brown, "Because, Olive, even though I'm always looking to add more, I'm not just going to put anyone's key on this chain. I need to like them first. That means knowing them outside of all the silk and chokers. Understand?"

The hare nodded, his heartbeat pounding heavily, "So...do you like me?"

Tom smiled, softly grabbing the hare's chin and opening his mouth. The old man's tongue and warm breath made Oliver's knees weak as he violated his mouth.

"Oh yes, Olive. And I have a gift for you back at my hotel. Would you like to see it, sissy?"

"Yes, Daddy."

***

Oliver couldn't see himself in the mirror. He knew the rabbit reflecting off of it was him, but he couldn't recognize her. From the dark eyeshadow and ruby red lips, the silky white bra and corset tied so tight that he felt it with every breath, to the garters tied to white leggings Tom had so delicately pulled up the rabbit's legs. The only hint of his masculinity came from the bulge of his cage, packed tight behind the white silk panties the raccoon had given him.

All of this, he'd given Oliver. The rabbit had some girly clothes, but never anything belonging to a complete set. He'd always been too afraid to order anything complete online, wary to check his measurements to make sure they'd fit him right. LDaddy...Tom had asked for them, and Oliver clearly needed to be more accurate in the future. If there was a future.

"Does Olive like her gift?" Tom asked, standing behind the hare in nothing but his leather hat, key necklace, and black thong. His heart skipped at the sound of his feminine name. Tom spoke it with such casual control that if it weren't for his cage, the panties would gain stretch marks. Oliver, no, Olive nodded, earning a laugh from the older coon as he curled a finger through his headfur, "You should grow this out," he said, "Then we can stylize it."

"It...it doesn't grow very long," Olive said, "It just sort of piles up. M-Maybe a wig?"

"Wigs are pretty, but no fun to grab," Tom said, pressing his wide gut against the rabbit's back, "I can work with short hair. Just let it grow out, you'll look lovely."

"T-thank you, sir." he said, blushing. His ears picked up something metallic behind him. Staring back at the reflection, Olive saw the older raccoon pull out a pink leather collar. His body shivered with warmth as Tom wrapped that collar around his neck, the final click feeling like he could finally breathe.

Tom brushed a finger down Olive's cheek, "Do you want me gentle," he asked, wrapping his hand tight around Olive's throat, "Or rough?" he growled, freehand groping the rabbit's backside.

"R-Rough, Daddy." he winced. Fear burned through his spine, but it only pushed his arousal further. The raccoon smiled, wrapping his arm around Olive's neck and asking, "I can do that, faggot. Now tell me, do you understand green, yellow, and red?"

With a nod, Tom chuckled, "Good." Grabbing the rabbit's headfur, Tom forced Olive to his knees and pulled him along the floor in a forced crawl to the bed. It creaked as the bigger raccoon sat against it, pulling Olive's face against his bulging thong and saying, "Get a nice good whiff of it, faggot. Beg me to use your mouth."

The coon's musk had Olive's cock twitching inside her little pink cage. The strong hearty aroma of a man more masculine than Oliver could ever hope to be, taking charge and holding him down like the pathetic sissy she'd been dressed as. Her face felt that throbbing meat behind the stretching thong, ready and waiting to claim ownership of the rabbit's holes. "P-Please sir," Olive whispered, "Fuck my mouth."

Tom answered by pulling his thong down, letting his erection finally pop out and giving the rabbit such a strong scent of his musk that Olive could taste it. "Get to work, bitch." He ordered. The chocolate hare was stunned at the size. The raccoon was clearly a grower, and bigger than Olive's personal dildo by at least two inches. While not exactly a virgin, when it came to men Olive had no real experience. Shaking with excitement and anxiety, her tongue dragged along the shaft, the taste of her manly master across her taste buds leaving her feeling empowered. The faint smell of urine still lingered from the tip, having been not long since the coon pissed, and the salty sweat of his balls had the rabbit shiver in delight.

Sir's hand never let go as Olive worked the shaft, guiding the bun along while giving Olive a healthy reminder of who exactly was in control. Not that Olive complained. No, she craved this. The control, the degradation and humiliation. Were it not for the cage, Olive's little sissyclit would be as erect as it had ever been, perhaps even more. She pawed at the cage, hopelessly feeling for any sort of stimulation across her cock. She still hadn't learn to cum from anal alone, having toyed with herself while taking in dildos.

With both hands, Tom grabbed her head and lined his cockhead against her lips, "Breathe through your nose, sissy." He ordered, slowly driving his thick rod past the rabbit's quivering mouth. The taste overwhelmed Olive, letting her moan in pleasure and humiliation at being this older raccoon's little fuckhole. It took a moment to keep a good pace with her nose, but once it was down she lathered her tongue across the cock inside. Sir bobbed her head up and down, never going too deep to test Olive's gag reflex, but never pulling out either. She was his toy, his personal sex doll to do with as he pleased. If Oliver could cum from arousal alone, his cage would be flooded with semen. Instead, it steadily dripped pre.

Tom pulled her off, tightly gripping her face as he smiled down on her, "That's a good little faggot," he jeered with every heavy breath for air the rabbit made, "If we keep doing this, then you'll need to deal with your gag reflex. I know a few helpful tips."

He tossed her to the ground before she could answer, letting the rabbit lay back against the carpeted floor. The taste of the coon's cock still fresh on her mouth, Olive only stared up into the ceiling while she heard the rustling of chains and the shifting of the bed. Soon enough, the raccoon pulled the hare up by her collar and kissed her, ruining what remained of her lipstick as he wrestled her tongue into submission. Olive melted in his grip, held steady by the strong hands of the older master.

Next she'd been pushed to the bed, creaking under her sudden fall. Taking her legs, the raccoon locked leather cuffs around Olive's ankles and hooked a spreader bar between them. Rolling her over, he forcefully pulled her hands behind and locked them in place with the same leather. Bound, the hare became helpless against his touch, biting her lips as he trailed a finger up her thigh to her ass, only to slowly pull down those panties.

"Such a cute ass," he said, massaging his thumb against Olive's back hole, "You ever been fucked for real back here, slut?"

Olive shook her head, "No, sir. J-Just toys."

"Just toys?" he asked, "Never even found a girl to peg you?"

"No. I've only used my cock on girls."

He swatted her ass, making the hare yelp into the mattress. "That's a shame. But I suppose that's better for me, it's been a while since I broke in a virgin hole." Tom teased. Her ears picked up the squirt of lube, followed by the sensual rubbing of it against her asshole before the raccoon slowly but firmly pushed his finger inside. "Relax, bitch," he ordered, "I know not having control is a new feeling, but I need you to relax for it to be enjoyable. I didn't have you clean out your ass for nothing."

Olive remembered that. The first thing Tom had her do the minute they walked into his hotel room. At the time, Oliver had thought it was the most humiliating thing in his life. Such a fool, it wasn't even close compared to what Tom made of him. Or her, now with these clothes. Relaxing her ass, the raccoon's fingers explored freely into her butt. Olive's ears focused on the squishy sounds of the lubed up fingers pushing deeper and deeper, keeping so much of her attention on relaxing for him. He'd already hit her pleasure wall, toying with her prostate to the point that she'd feel so close to cumming, yet couldn't despite the prodding.

Tom chuckled, shifting the bed as he kneeled up to and lubing up his own cock. Olive gasped as he pressed the tip against her slippery hole, fingers gripping the open air from behind her back. "Time to treat you like a proper woman," Tom said, pushing past that anal ring. Olive grit her teeth as the hot pulsing rod pushed into her backside. She'd had dildos before, using them often to masturbaite despite their prepwork. But having a living member inside her, all while caged, was a different feeling entirely. He hit deeper than her toys allowed, filling the chocolate bunny up to a perfect degree of pleasure and pain.

Then he pulled back. Not all the way out, but a noticeable difference had been made before thrusting back in. She squealed, her body shaking with the momentum of Sir's hips. Again and again he fucked her, gaining speed until the soft squishy sounds became slaps as he pounded into her. Grabbing her headfur, he pulled her off her bitten pillow so Olive couldn't hide her groans and gasps. She swore, each pistoning motion bringing her closer and closer to pushing past that edge, but not enough. Never enough. Olive stayed at that edge of pleasure far longer than she thought possible, denied not by Tom's desire, but her body's own inexperience from cumming this way.

The raccoon had no such problem. Even with more stamina than his physique suggested, Tom had to burst eventually. He pulled her in when it came, wrapping her strong arms around her waist as strand after strand of cum filled the rabbit's bowls. She mewled as they collapsed into the bed, her arousal dropping despite being so close.

Tom reached around to toy with her cage, "Did my sissy faggot not cum?" he teased.

She nodded, "My keys...they're in my pants pocket," Olive explained through pants. She needed release, even if that meant pawing herself off while he watched. Though the hare would prefer he did it, giving her a handjob or, heaven forbid, a blowjob from the older gent. Stepping off the bed, Tom didn't move toward the pile of Olive's boy clothes. Instead, the old raccoon reached into his bag and pulled out a wireless hitachi wand.

"Let's try something else first," he said, rolling Olive onto her back and pressing the head of the vibrator against her cage, "To be my sissy, there's a little criteria you have to meet. This little cock," he tapped the vibe against it, "loses its rights to cum like a man when in my presence unless I make another bitch suck it. This means you best learn how to cum through your ass, and fast. Or pray you're able to cum through this." He explained, turning the wand on before Olive could answer.

The vibrations rattled against her cage, pushing her sensitive cockhead to the edge from stimulation. She thrashed in her bondage, held down by the stronger coon as her arousal built up and up. Panting, it took maybe a half-hour before she finally came, her seed dripping slowly from the cage as her body shuddered in orgasm.

Unlocking her restraints, Tom crawled back into bed with her. Playing the little spoon, Olive rested against the bigger belly of the older coon, relaxing after his first caged orgasm. After an hour of rest and aftercare, Olive stood up and pilfered through Oliver's shorts until she found her chastity keys. Blushing, she handed them to Tom, taking a knee and saying, "For you, S-Sir. If you will have me as yours."

"Are you sure?" he asked, "I can't see you every day, or even every week. It is a little bit of a trip to see you, so we couldn't have more personal sessions often."

Olive nodded, "T-That's fine. I can train through email so I'll be better prepared for you."

"Really now?" he asked, taking the keys. Olive had done it, signed away the freedom of her cock to another man. Regret and fear filled her throat, but she was determined to see this through. Then Tom placed one key in her hand, and rolled her fingers around it.

"For emergencies," he said, smiling down before kissing her.