Tilly Tufty

Story by tygacat on SoFurry

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Matt has just turned eighteen. He is of the age to legally indulge in the variety of sexual entertainments the world has to offer. To celebrate he wishes to indulge in as many of those entertainments as he can at the city of Lyra; the wellspring of the modern sexual renaissance. But he does not want to go alone. He has his heart set on sharing all of this with Caroline. Caroline who is a family friend, his godmother, and a personal mentor through life. She has agreed to go with and be his guide through it all. So together they travel to the city to indulge in all it has to offer.

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Ten Nights in Lyra

Chapter 6

Tilly Tufty

That seafood dinner hit the spot. At mention of Bonnie's name the proprietor was quick to provide appetizers and drinks on the house. They felt guilty on the matter; feeling they'd stumbled into the middle of something. Still, it became clear early on they'd not be able to refuse the offers. They tried to not take too great an advantage of the situation. All that said, the food was really good.

They retired to the hotel room, a welcome sight after the busy day.

They settled onto the bed. Matt turned on the T.V. He flipped through channels before landing on a cooking show. Caroline picked up the room service tablet just out of curiosity for the options available. For certain there were a wide variety of

She flipped into the raunchy options available. Of course the hotel had a wide variety of sexy shows available on demand for order. More interestingly one could order various sexual paraphernalia if they desired. The icing on the cake, however, was the offer of various courtesan services. Sex work was legal practically everywhere on the world of Saffron, but this was the first place Caroline had been to on the planet that made it so readily available.

She flipped through the selection of available listings. Caroline wondered how this all worked. There was likely some agency that mediated between the workers and the hotel. Caroline let her interests guide her. Ladies. Felines. Mmm, caracals. She'd never fooled around with one before. She tapped through a couple of profiles before settling on one lovely lady. Tilly Tufty, as she advertised herself. Caroline doubted it was her real name.

Her specialties and interests list was mostly a lot of vanilla activities. That was fine with Caroline.. Also she claimed to like things 'low and slow,' which was also good. Caroline didn't need to bite off more than she could chew after the eventful day. The picture provided of the caracal was a sensuous one that left little to the imagination. Caroline didn't like having to imagine, though. She just needed to make sure this was okay with Matt. Though she doubted it would be a hard sell.

"Hey, Matt? Want to see me fool around with another woman?"

"Uh, I did that already today," he said.

"I mean again." She stuck her tongue out.

"I, uh, I'm kind of wore out,"

Harder sell than she'd expected. She supposed just because he was young didn't mean he was completely limitless in hornball energy. She tailored her pitch to the situation, "Yeah, this lady says she's good for low and slow. I don't want to go too hard either. I'm just curious about playing with this thing. Plus I've never been with a caracal, and this lady is looking intriguing."

"Oh, in that case go for it," he smiled and rubbed his crotch lightly. Didn't take too much convincing, she noted with a laugh to herself.

Caroline pushed buttons fast hoping no one else got to pounce on this lady before someone else did. Success! The back of her mind ached at how bad her credit card bill would be for this trip. She told that part to shut up, they'd cut down on the good coffee for a while.

Caroline looked up at Matt who looked like he was having exhaustion-induced reservations about this. "Don't worry, you don't have to get involved if you don't want to."

"I'll see. I'm sure I'll be fine once things get rolling. I'm just surprised you're the one being so energetic."

"Hey, I'm not that old. Besides, I'm kind of feeling like a youngun at the moment," she giggled.

"I'm glad you're enjoying the trip."

"So far it is exceeding expectations," she smirked. "Think I should order another bottle of bubbly?"

"If you want. I doubt I'd drink much."

"Well, I'll pass then." She settled back on the bed and watched the television with him for a while. Caroline almost forgot she'd ordered some entertainment for the evening until there was a knock on the door.

"Oh, yes," she leapt up. "Coming!" she yelled. She bristled with excitement and anxiety. She glanced back at Matt. His fur was perked up in excitement. Caroline headed to the door.

The caracal lady stood out there in a nice and skimpy little black dress. "Hello, I'm Caroline. You must be Tilly?"

"Yes," the caracal said.

"Come on in," Caroline invited.

Tilly nervously looked over Caroline's shoulder before following her into the hotel room. She relaxed once she saw Matt grinning a goofy hornball grin.

Sex work, as mentioned, was largely legal throughout the world. This was facilitated by numerous factors. Most relevant to this interaction was a general societal intolerance for sex abuse. Laws and punishments could get harsh quick. Even so, it still involved walking into an unfamiliar environment with unfamiliar people who were sexually and emotionally charged. Things could get difficult and uncomfortable quick even when not outright illegal.

A couple of goofy tourists who clearly barely knew what they were doing likely registered as being far from a threat.

"I'm, uh, going to see some I.D." she said, noting Matt's youthful appearance. "I mean, need to see some I.D."

"Oh, of course." Matt and Caroline fumbled through their things searching for where they'd left their cards. Caroline cursed herself not using the time while they waited to get prepared. At least the caracal didn't seem too upset by this; if anything she seemed a bit nervous about the delay. She must be new to the profession.

Matt was first with his card.

"Matt, huh? Eighteen, getting close to nineteen," she did the math in her head. "Looks good. You're from Triska?"

"Yeah, a short ways east of Xetu," Caroline remarked. She handed her own identification over. While she had no doubt that she appeared of age, there was other information to be gleaned from the card. It held the standard symbols for health information; pertinent to this the three marks indicating she'd had her shots.

"Excellent, excellent," Tilly said and handed back the card. "So, what are you interested in?" She shifted her weight to a more suggestive pose.

Now, that was always the question, wasn't it? Caroline had, in her day, solicited sexual experiences a handful of times in her life. On more than one occasion she'd gotten to the point of them asking for specifics of the interaction for the evening she'd freeze having not thought that far ahead. Sex as a general concept was all that was on her mind, rather than a specific course of action.

She looked to the audience. Matt was eager to see what was going to happen. She wanted to fool around with Tilly in front of him, but not in the same deliberate putting on a show as earlier. More she wanted Matt to see her fooling around the way she would without an audience.

"Well," Caroline sat back to the bed. "First I'd like to see you naked. And don't take your time about. I've never been one for overly drawn out strip shows."

"I can supply that."

"What should I do?" Matt inquired, grinning idiotically.

"You, can sit back and enjoy the show."

"Oh, okay," Matt said, settling back into the chair. Tilly glanced from him to Caroline.

Caroline realized he hadn't actually spectating had been all he'd gotten to do today. Also, she'd assumed he'd be tired and would just want to sit back and let her do the work. He seemed that way a few minutes ago, though having the sexy lady now in the room may have kick started his sex drive again. Still, Caroline felt she should have asked.

"I mean, you can certainly participate if you'd like. As long as it's okay with Tilly, of course. I'll pay extra, I'm not exactly sure how it works here."

"I charge by the hour, so whatever you want to do. I'm certainly cool with bisexual threesome stuff."

Matt perked up a lot. This was the right way to go. She'd have to change up her intentions for the night. She could use it as a bit of a teaching opportunity for him. Gears turned quick in her head. "In that case, Tilly, you sit with me. Matt, you get naked for us."

Tilly slipped in alongside Caroline. The tuxedo cat put her arm about the caracal. Matt gave a short look that seemed to question why he'd be getting naked when they were paying Tilly to do that sort of thing. Well, this would be his first lesson of the evening. Just because you're paying someone for their company, sensual or otherwise, does not give you license to treat them as objects. Besides, last time Caroline checked she was the one paying for Tilly's company. So if she wanted to use the caracal's time having her sit back and watch a sexy male strip show, that was going to be what happened.

Matt quickly lost the look though and decided to just go with it. He pulled his shirt over his head, baring his orange chest. "Mmm," Caroline murred.

"Nice," Tilly followed.

Matt blushed a bit. He tossed his shirt to Tilly. She caught it with a laugh. He was a quick study on this sort of thing.

Matt unbuttoned his jeans. Tilly straightened up, her ears perked. Caroline smirked. She'd picked a good one.

He got a bit flustered and embarrassed. "I'm not going to fast, am I?"

Caroline snarked, "I already said I'm not one for drawn out strip shows. Lose the britches."

He pulled his shorts down. His boxers weren't fully tented yet, but there was a noticeable bulge. Tilly licked her lips. The bulge grew larger. Matt hooked his thumbs in the elastic band, gave the ladies a smirk, and pulled them down. He kicked his pants to the side.

"Aow!" Tilly howled.

Matt stood in a mix of prideful and bashful nudity. He wrapped his hand about his now swollen length and gave himself a couple of slow pumps.

Caroline clapped. Tilly twirled her finger in the air.

Matt obliged and turned about; raising his tail and showing off his bare tangerine backside.

Caroline clapped again. "Okay, now you two switch places."

Tilly hopped to her feet, eager to get to work. Matt cuddled up alongside Caroline. Her eyes glanced to his hard pink cock. She looked forward to seeing where that ended up tonight. Now, though, she turned her attention back to the caracal.

Tilly had a fair bit more practice putting on a show than Matt, unsurprisingly. Still she kept the performance short as requested. She turned about and bent over; letting that short tail lift the short skirt up. Her thumbs hooked her panties and slowly shimmied them down to bare her ass and pussy for her onlookers.

Matt grabbed his cock and squeezed. Caroline bit her tongue lightly; blepping ever so slight.

Tilly righted herself. Her dress fell back down concealing her nethers. She wouldn't tease for long, though. She turned to face them and hoisted the garment over her head. All that remained was a small sports bra over her chest. She made short work of that to stand in glorious nudity.

Caroline nodded her approval. Matt squeezed his cock to show his.

Tilly crawled up on the bed toward them. Matt poked Caroline's shoulder, "Your turn."

She returned his gaze with a smarmy glare that said she was in charge, and she was only obliging because she intended to get naked anyway. She stood and walked to the foot of the bed. She'd be more deliberate in her disrobing. Her jeans went down first, then off came her top. Her bra undone, her panties pulled down. She flicked her tail over her bare ass, then turned sharp for the full frontal show.

Matt stared, flicking his eyes to her boobs, then pussy, then back. Tilly took her all in while rubbing at herself. She still had it, Caroline thought.

She widened her stance and placed her hands on her hips. "So, what's next?" she asked in a sultry tone.

"You're paying," Matt stuck his tongue out at her. Tilly laughed. He was too good at taking cues.

"You're right, I am." Again, she was back in the seat of having to actually choose something. "Well, if Tilly would be so kind as to get on all fours for us?"

"Can do," she assumed the position. She kept her short tail in the air exposing keeping that pretty rump on display.

Caroline had done quite a bit in this position earlier, but it was not one of which she ever grew tired. Caroline stroked the bare backside of the cat. Matt slowly slipped around to get a look for himself.

"So, just to verify," Caroline asked. "What is good and what's off limits?"

"Uh, I'm good with pretty much anything. Er, well, far from anything anything. But I mean most of the basic stuff. Pussy stuff, tit stuff, though I'm gathering you two are more interested in ass, hehe."

"Indeed. Especially this one," Caroline said. "So, butt stuff."

"Fingering, fucking," Tilly acknowledged.

"Rimming?" Matt said hopefully.

"Not that."

"Oh," Matt said.

"Sorry, not my thing."

Caroline bopped his shoulder. "You'll have to make do with other fun tonight."

Tilly chuckled, "If you want to kiss my ass you'll have to make do with the cheeks."

"Now, even I'm good with that one." Caroline said and smooched the rump. Tilly giggled. "Matt, I've got a bottle of lube in my bag."

While he was doing that she teased her fingers over Tilly's asshole. The red cat cooed. Caroline might have actually been tempted to put her reservations about the thing aside and kiss it had Tilly not just said she didn't like that sort of thing.

Matt returned with the lube. Caroline placed a small dollop on her fingertips to push them into Tilly's rear. Tilly cooed. Lubing up her other fingers, she pushed them into the pussy. Both holes filled, the caracal melted.

Matt jerked himself lightly watching Caroline play. "I'm going to play with her tits."

"Okay, make sure it's okay with her," Caroline said.

"Of course!" Tilly responded.

Caroline noted the irony of wanting to show Matt how not to treat a courtesan as an object while simultaneously talking about her as if she can't hear. "I'm sure, I just want him to get in the practice of always asking." There, that should save face.

"Ah, gotcha," Tilly replied.

"May I play with your breasts, Ms. Tufty?" Matt asked in a faux sophisticate tone.

"Yes, you may," she giggled.

Caroline and Matt played with their guest with little said between them. The only noise were the various squeaks and moans of pleasure, or her occasional instruction of 'harder' and 'not that hard!' to them.

Caroline wished she'd had brought some toys with her. She'd considered it, but ultimately opted to leave them at home. They had them for purchase via the room service thingie, but she was not about to gamble on that. She'd have options later in the week, possibly.

But for now, she'd have to make due with stuffing this ass just with her fingers. Well, there was another option about stuffing this hole. She'd have to sacrifice her chance at being Matt's first anal. Well, at least his first female anal fuck, as far as she knew. They'd have many opportunities for firsts together, though. This would likely be the only time she'd get to see him up Tilly Tufty's backside.

"So, Ms. Tufty, I presume you are good with regular anal sex?"

"I am!"

"Matt, want to fuck a hot caracal ass?"

"Yes!"

The ladies giggled at the eager young man.

Tilly shifted about in anticipation. Caroline dabbed a fresh bit of lube onto the dark tail hole. Matt assumed the position. Caroline helped guide him in. He didn't have much trouble between the lube and what work Caroline had done to loosen him up. Tilly gave a pleasant moan of satisfaction.

"That's good," the caracal moaned. Tilly reached under her body to rub herself. "Mmm, yeah."

"Oh," Matt moaned. Caroline cupped his balls beneath his cock as he slowly fucked Tilly's ass. "I don't know how long I'll last."

"Don't worry about it," Caroline said. "We've been pushing you pretty hard."

"Mmm," Tilly moaned her agreement.

It wasn't much longer after that that Matt gave way, filling Tilly's rump with his cream. "Damn," he said. "Fuck, that's good."

"Hee hee," Tilly was glad he enjoyed.

Matt staggered back off of her and collapsed in the chair. Tilly moaned at the loss of the dick up her ass. Caroline shoved her fingers in, hoping to be a decent substitute. Tilly played with her pussy, pushing herself to orgasm just minutes later. Caroline leaned back and took her pleasure; massaging her pussy and cumming across Tilly's back.

She collapsed back into the bed next to Tilly. "That was great fun, thank you."

"You are welcome. Thanks for hiring me."

"I assume payment is handled through the room charge somehow?"

"Indeed."

"Such convenience. Never been at a place where I get such things through room service."

"Well, that's our Lyrian efficiency," Tilly chuckled. "Your friend is pretty out of it."

Matt was zoned out on the chair.

"Yeah, I should help him into bed," Caroline stood to do just that. "I don't blame him. We've had a full day."

"Well, I'll let you get some rest. Mind if I use your shower to get cleaned up before I head out?"

Caroline helped Matt into the bed. The orange tabby was out as soon as he hit the bed.

"Of course," Caroline said.

"I'll be quick and quiet, if you want to get to sleep." Tilly said stepping toward the shower. "Of course, if you've got a little energy left you could join me. Half price." She swished her hips.

Caroline leapt to her feet.