Worth the 25 Year Wait

Story by Joshiah on SoFurry

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Losing one's virginity can become such a powerful weight on someone's mind that it dictates their entire thought process, and for his 25th birthday, Travis can't think of a better gift to give himself than the feeling of his first sexual experience. In this story for TCF, he finally crosses that line, but guaranteeing his success comes at a literal price.

Taking advantage of a known burlesque house down the street from his apartment, Travis bails early on the party his friends have thrown him, having paid for a date in advance with a slightly older woman. When he arrives, the facade of a sexually experienced man is quick to come unraveled, and Cassandra, the woman of his choosing, kindly gives him a chance to reconsider paying for his first time in literal coin, rather than time and connection.

He opts to stay, and by the end of the night, both of them are rather pleased with his decision to do so...

Commissions are open! https://docs.google.com/document/d/1M4k7uyTIRESrkmEhcuQPtznK7qDFrDH358Vk9-bYrGY/edit?usp=sharing Our first block of the year features 60,000 words, a few new commission types, and all kinds of fresh benefits from the Gold Club!

If you enjoyed this story and want to help me keep creating, check out my Patreon! https://www.patreon.com/Joshiah It's been updated for 2020 with exclusive content for as little as $1 a month!

As always, read, comment and enjoy! Be sure to check out our current YCH stories, as well! http://www.furaffinity.net/journal/9372987/https://www.sofurry.com/view/1531380


A night out on the town wasn't a bad way for Travis to spend his 25th birthday, but by that point in his life, he was already growing weary of spending copious amounts of money on alcohol, just to return to an empty apartment at the end of the night.

Naturally, he didn't end up paying for a single drink on his birthday, and the smile he wore around his best friends was genuine, but it was every bit as tired; there was no way for the ursine to hide his stress with an overbearing issue any longer.

Societal pressure could be a terrible thing.

"Yeah, I made it back to my place just fine," he said, talking to one of his friends over the phone. "No, I don't need you guys to come over and check on me...like I said, you wore me out! We'll pick up game night next weekend, okay?"

It was comforting to have friends that cared so deeply for his wellbeing; Travis hated lying to them for any reason, but he knew if they came over to his apartment that night, he wouldn't get to sleep until four or five in the morning, and he'd never get back out on the streets if he was busy entertaining his guests.

He had another present waiting for him, and it was one that he'd planned out for himself weeks in advance of the party his friends threw.

"I know, I know. Right to bed. Thanks, Mom," he joked, hanging up the phone immediately after. He wasn't going to let the big moment get delayed any longer; he was liable to lose his buzz if he did, and along with that, his liquid courage would be all gone.

He'd been told plenty of times that he shouldn't be drunk before such an important moment, but he couldn't help getting a little bit tipsy when he was out with his friends for what many considered to be a monumental birthday. Turning 25 didn't seem like that big of a deal to the bear, himself, but his friends were treating him like a king, buying him drinks from the top shelf and paying his way to and from the bar.

He took to the streets again on foot, as he walked through a neighborhood that should have been seedier, given the nature of his visit.

The storefront wasn't too far from his apartment, but two city blocks could feel like two miles, even when you weren't about to enter the door of a privately owned brothel.

"You're right on time, Mr. Jones. Did you ever come to a decision about who your lucky lady will be for the evening?"

For as long as the walk seemed to take, with the gravity of the situation looming over his head, it seemed like he'd only just stepped out of his apartment building a second earlier, when he was standing in front of the receptionist's desk.

He quietly wished that he'd walked a little slower, as if he needed more time to contemplate an already impossible decision.

"Not to be a bother, but...n-no," the bear nervously struggled through his reply. "To be honest, I'd be more than happy to lie with any of them, but I can't begin to fathom which one would be the perfect fit for me."

The receptionist had seen all manner of men and women alike come through the front doors, and though it was rare that they'd confess to such, she could spot a virgin from a mile away.

Travis' 25th birthday present to himself was the departure of his cursed virginity, but his pool of dating prospects was so dry that he could have rented it out to local skateboarders. Options were running thinner by the day, due mostly to his desperation...but there was an option left that he refused to confess to anyone; not even his closest friends knew where he was.

"I can wholly recommend any female that currently has availability for the evening," the receptionist offered. "Among them, there's a wide range of species and specialties...is there a specific personality or kink that you're looking to indulge?"

She wanted him to come out and admit that he was a clueless virgin, but it was never as easy as just asking a customer that question.

Instead, her question was met with eyes that darted from side to side, as if his big 'secret' had been given away.

"Just...someone sweet, I guess?" he tried to come up with an answer on the spot. "Someone who can make it feel like they authentically care about me?"

"We get that a lot," the receptionist replied with a quick giggle. "The women here are all more than capable of making you feel special and cared for, no matter what that means to you."

Travis didn't want to sound like a clichéd dork, but at the heart of it all, he really did just want his first time to be something special and spontaneous.

He'd given up on the latter, but still believed it could be the former, if it was with the right woman.

"Maybe someone with a little more experience?" he suggested, unsure of the right way to describe a girl that was slightly older than he was. "Someone who can...uhm...guide me through the whole process...make me feel like a virgin...a...again! Make me feel like a virgin again, y-yeah."

He was adorable enough that the receptionist was quietly hoping she'd be working one of the rooms the next time Travis came around, but as she looked down through the binders of each employee, she realized that his perfect match was already waiting for him in a room upstairs.

"I'd be willing to bet that I could do that," she claimed, "But I'm afraid that's not my job around here...it is Cassandra's job, however, and she's up in room 203. Take this key with you and head on in whenever you're ready; I'll notify her over the PA system that she's got a customer coming up."

Travis never saw what the receptionist properly looked like: tinted glass covered up the majority of her appearance, with only white fur on a small, dainty paw pushing the key through a slot in the front window.

Without seeing her eyes, he could imagine how kind they were, after such a warm welcome.

"Thank you," he did all that he could to keep from stammering or sounding nervous as he clutched the key in a paw and moved toward the lobby.

The building wasn't so opulent on the inside that it intimidated him, but Travis was definitely beside himself as he walked through a wide, open lobby that reminded him more of the gathering area in an old-fashioned train station than it did of a burlesque house. High ceilings and floors tiled with real, carved stone slabs made for such a fancy appearance that he felt underdressed, and even a quiet cough behind his paw left his self-conscious; the main area had quite the echo to it.

If he'd kept walking straight through, he would have come to another, smaller open area with directories to the different stages that were open: these were public stages were the general attendees could gather and watch a show together. Actresses and dancers graced those stages almost all hours of the day and late into the night, going about their act whether a single man was sitting and waiting for them, or if hundreds of guests were eagerly cheering them on.

Travis went right up the board, skipping over the smaller packages available for his entertainment. If turning 25 was going to be a special occasion, he wanted to do something more than have a stripper sit in his lap and lie to him about being special.

He didn't know if Cassandra was going to tell him that same lie, or if it would even be a lie from her...but he knew that he'd paid for the grand finale, and that was better than having to go home and rub one out after being worked up by a dancer.

"Is it wrong to just pay for something like this to happen?" he asked himself in a hurried whisper as he made his way up the stairs to the right. The lights above the stairs were dark enough that he had to literally watch his step as he ascended to the second floor of the building, his ears twitching at each and every creeeeak that came from beneath his nervous feet. "Should...I just...leave?"

A sweet scent immediately beckoned to him as he came up to the landing of the second floor. The stairs wrapped around to the right and continued up a few more floors, but he was already at his desired location, standing in an empty space with nothing more than his own insecurity, and a sign on the wall to distract him.

"203 is to the left," he read the sign needlessly before turning that way; he admired just how dedicated the building was to keeping a dark and mysterious profile, complete with dull, flickering lights from candelabras and a rich, mahogany choice of wood that turned his entire world into a cavern of cherry glows and enticing aromas.

Even through all of the beauty and mystery, his own self-conscious nature cut into the heart of his thoughts, reminding him of how close room 203 was to the stairs. He noticed that he couldn't hear any lewd sounds from the rooms that he'd passed, but he just assumed them to be empty.

He was wrong about that, and wrong to worry as much as he did. Quivering digits formed a nervous fist, and knuckles weakly rapped on the door, just to the right of the brass '203' that was emblazoned upon it.

Expecting to hear a quiet, sensual "Come in," Travis nearly jumped back when the doorknob began turning thanks to a delicate touch on the other side.

He smiled nervously, pretending that he was anything but nervous as a woman revealed herself from behind the door. She'd picked out a comfortable robe of silk for the evening that was just the right shade of red to avoid being sheer, but it pressed tightly enough to her bodice that Travis could see she'd only picked out a brassier and a pair of panties to go underneath.

Trying not to shamelessly ogle the outline of her lingerie as she stood in the door, Travis met with her eyes and the expectant stare in their depths as she returned his smile in a confident form. "This is usually the part where you would say something," she teased, cocking a brow at his obviously terrified smile. "You're not mute, are you?"

He shook his head.

"Well, you're not paying me enough to have sex with you out there in the hallway," she offered a quick joke and softened her smile, able to tell right away that this wasn't an easy decision for him to make. "If you step inside, though...maybe we can work something out."

With a more experienced customer, she would have accented her words with a quick, glancing stroke over the bulge in his pants, putting an exclamation point on an already powerful sentence.

With Travis, she merely stepped back from the door and crooked a pawtip at him, knowing that he'd follow her beckoning claw like a hungry fish chasing a hooked worm.

"That's the way, big fella. I'm not gonna bite unless you ask me to," she made sure to giggle at her own quip, unsure if the bear could take a joke at that point. "You just come take a seat wherever you like and make yourself comfortable. Would a drink help, perhaps?"

"I...uhm...y-yeah. Sure," he finally found his voice at that, stepping into the room and closing the door behind him. As it latched shut, he heard a locking mechanism from inside the wall that was operated by the front desk; the place wasn't entirely as old-fashioned as it seemed, but for the safety of the workers, it seemed like a logical addition.

Somehow, it even made Travis feel safer as he stepped into the middle of what appeared to be a fairly massive hotel room. In the middle was the bed that he expected, complete with pink sheets and decorative pillows of white, black and gray, but the sectional couch that wrapped along the wall, the entertainment center, and the cocktail bar were extra touches he wasn't expecting.

It felt like he'd wandered into the loft apartment of a wealthy businesswoman, and he just happened to be the lucky man she chose to bed that evening.

"What's your poison?" she asked. "And why aren't you sitting down yet?"

"Oh! I'm s-sorry," he stammered out an apology and plopped right down onto the sectional, keeping his paws firmly over his knees. "A glass of bourbon would be lovely, actually. Any old variety will do."

"Seems that you know a lot more about drinking than you do about talking to women, Travis."

"You're not wrong," he muttered, but then, his eyes widened. "Wait, h-how did you know my name?"

"Our receptionist makes sure that we're briefed on our clients before they arrive, and you took your sweet time getting up here...she wasn't able to tell what she was smelling on your breath before you walked away, though. I would have had a glass of your favorite waiting for you already, otherwise."

Travis blinked as snowy feline poured a generous serving of brown liquor into a glass of finely carved crystal. As if she was a wife tending to her husband after a long day, she popped her hips just a little bit with each step, bringing the drink to him without ever lifting the enchanting ice of her eyes from his own.

"What else did she tell you?" Travis asked, finally having a talking point that allowed him to avoid the elephant in the room.

"Just that you were looking for someone sweet," she explained, handing the glass over to him with a sly grin. "Someone to make you feel like a virgin..."

Travis gulped at the pause in her explanation, before she finally whispered, "Again...right?"

The poor ursine was worried that he'd been obvious about his secret, but he had no idea just how clear the truth was until he felt Cassandra gazing right past the inexperience in his eyes, to the heart and soul of the matter.

"Y...yeah...again," he gulped.

"I want you to know something, Travis..." she leaned over, resting a palm on the back of his knuckles. The touch was electrifying, but only stiffened his form up that much more as he tried to go flat against the couch. "You're not fooling anyone...if you just want to sit and have a drink with me for a few minutes and go on your way, I'll refund you everything but a tiny deposit for my time. It's a big decision to lose your virginity this way, and I don't want you to regret it later if you do."

To come as far as he had and make the decisions that he'd made, Travis couldn't fight the initial reaction of disgust and insult that came from the words of an experienced prostitute.

Being wise and sober enough to process the words first, however, he was able to swallow back that pain and acknowledge that Cassandra was actually doing the sweetest thing she could have: giving him an out before there was no way to escape from the throes of passion.

"Before I decide, can...can I ask you something?"

"You've already paid for my time," Cassandra reminded him. "It's up to you how we spend it."

That answer was a bit more of the cold, calculated tone that he was expecting from her, but Cassandra was already different than he anticipated. Travis was raised with a preconceived notion of how his first interactions with a prostitute would go, just based on what he'd seen in movies.

He didn't think they were capable of caring about their customers in the way that Cassandra already cared for him, but he also didn't know just how much of that care was genuine, and he hated that uncertainty.

"Well, f-first...how did you know for sure that I was a virgin? How could you tell that I wasn't acting?"

"All I do is put on an act, based on the fantasy of whatever man or woman comes through that door," she said, pointing right past Travis' expression. "Years of doing that have made it fairly obvious when someone comes through and doesn't have their act together."

"And when someone comes through acting as nervous as I did..."

"I'm pretty sure I'm the first woman you've seen this close to being naked, much less the first woman you've had touch your thigh this way," Cassandra pointed out. "It's a flattering thought for me, but you wouldn't be the first man who's offered me his virginity, and I'm sure you won't be the last."

"So...there's nothing I can do to make this moment special."

"Is your mind set on doing this?"

Travis blinked as her claws slipped back from the inside of his thigh. She stood up and gave him a smile that was more motherly than anything, but somehow, it gave him the greatest sense of comfort he'd felt since he walked in the front door.

"I guess I don't know," he admitted. "I was in such a rush to lose it that I didn't think much of the consequences, but I'm starting to get an idea of what people mean when they say the first time should be special...that it should just happen."

"They might be onto something," she half-agreed. "Or, you might just be sitting on a couch in the bedroom of the naughty girl next door, and she might just happen to grab your cock through your pants and see what you do about it."

A thick lump traveled _slowly_down his throat. "That's...n-not where I expected you to take that."

"And that's about how I expected you to react," she claimed, giggling. "I agree that sex isn't the kind of thing that you should force, but I've had plenty of men come into my room with a fistful of cash and a dream of getting laid, only to leave after a pep talk and a peck on the cheek. You, though...I don't think that would work on you."

"You d-don't?"

"Not at all, Travis. You're cute, sweet, and it's obvious that you've had your mind set on this for some time," she explained. "And you seem like the kind of guy who will get the bigger picture after you come a little closer to it."

Her paw slipped right up the front of his leg once more, moving with aggressive intent. Travis slumped back into the couch nervously, but even as Cassandra rested her other paw on his chest and came in closer, she could feel his heart racing beneath her palm.

"You're a shy guy with a few cracks in his shell," she described him to a 't' as her eyes narrowed on his own, capturing his gaze. "Fucking me won't change that, but you seem to think it will; I don't want you to waste your virginity to answer a pointless question when there's nothing missing in your life, cutie."

She'd talked through his every doubt and given him the option to leave, but when she expected him to pop up from the couch and agree with her sentiment, he remained frozen, both with the strength of his intent and the nerves that she continued to fray.

"Maybe there _isn't_anything missing in my life," he agreed, "But...no one knows that I'm here right now, Cassandra. No one after you needs to know that I ever was in the first place."

"Nope. You can make up whatever story you want," she echoed the idea. "But is that what you really want?"

She didn't expect to feel his palm around her wrist; she nearly dropped the drink as he trembled, holding her. "All I know is that I've wanted this for too long to go without it any longer," he confessed. "It's been dominating my every thought, making me self-conscious at every turn...virginity might be the kind of thing that some people want to lose in a special way, but to me, it's a burden, and...I just want someone sweet to alleviate me of it."

A startled expression calmed as Cassandra hinged on his every word. "But you're too nervous and unsure of yourself to go out there and find a girl who will accept that you're inexperienced...whereas I don't have a choice."

"Something like that."

"While I can promise you that most women aren't as judgmental towards an inexperienced lover as you think we are, you've already taken up this much of my time, you're still here...and you are kinda cute," she freed her wrist from his grasp as she placed the bourbon on an end table, figuring it a needless thing anymore. "You can be as nervous as you want around me, Travis. You can tremble the whole way through if your body tells you to..."

His lower lip dropped as Cassandra pulled the tie from her robe and allowed it fall from her body in a crimson waterfall. She stepped out of the puddle and stood between his legs, looking down upon him with a glare that made it clear who was in control of their interactions.

"You're unsure of yourself; I can still see that in your gaze, but your intentions to sleep with me have never been clearer than they are now...and if you can live with that decision, I can fuck your brains out without any guilt, big guy."

Travis didn't think his request for a sweet, kind prostitute would go beyond the surface of a woman who would butter him up and make him feel better about himself. To have a woman with such depth of character as Cassandra already enriched the experience, leaving him to feel as if he wasn't just her customer for the hour, but a sexual partner that she'd still think about long after he shuffled back through the lobby.

"I didn't think fucking my brains out was the kind of thing a sweet girl would do," Travis said, his voice closer to a whisper as he watched the slender feline hook her thumbs into the waistline of her panties.

His jaw dropped as she lowered them with a slow, alluring pull, letting him watch the crest of her womanhood appear. Her clit was proud to be revealed, standing at the top of a set of folds that left Travis dry in the mouth, even when he was sure he saw a faint shimmer upon them.

Black lace hit the floor as she stepped forward, straddling his thigh in a move that was so much quicker than all of the others; she wanted to keep him guessing.

"Sweet girls don't know how to fuck someone's brains out," Cassandra explained. "But the sweetest of girls can do that and so, so much more...or at least, we can when our lovers finally fish their cocks out and stop making us wait."

Truth be told, she just wanted to see if Travis would rise to the occasion, but as her juices began to puddle on his clean, smooth dress pants, she could already see the impressive outline of his bulge. The boy had nothing to be shy about, but he was still squirming as paws snuck under the chub of his belly and began tugging at a zipper.

Cassandra was used to seeing members erupt from their cloth confines, but she still giggled when his inexperienced flesh popped free, slapping up against her wrist and spilling precum onto her pristine, white fur.

"S-Sorry! I...I didn't think-

"You're here to fuck me, and you're sorry about touching me with your cock?" she teased, opening her palm to grasp the shaft. "You really don't have any idea how this works, do you?"

Travis wanted to ask if she meant sex, or sex with a prostitute in specific.

He was glad that he caught his own tongue on that matter, along with a quick assist from Cassandra, who began pumping up the length of his messy rod.

"Pretty s-sure that's working j-just fine," his voice immediately shuddered with delight, along with the rest of his nervous form. He was trembling just as she'd predicted, and while he felt silly to question her experience, he quietly wished that he could make his body hold still.

The vibrations only grew stronger as she rested a palm on his shoulder and began climbing properly into his lap.

"It's not a bad way to start," she agreed, "But it'll never get us where we need to go, Travis. Your little sweetheart is gonna take you to the promised land, complete with a creampie so thick, you'll have to go on a diet..."

She was still pulling from her experience in the field of adult work, but her words weren't overly laced with forced lust and arousal. She was starting to genuinely enjoy herself, as well, having put her guilt to the side in favor of something much more fulfilling.

Holding the entirely filling length of his member with her paw, she steadied it as she lifted her hips into his face, dragging her mound over the front of his muzzle and staining it with her scent before she pressed it back onto the drooling tip of his cock.

"Just a little something to remember me by," she told him, able to see the curiosity in his eyes. "That'll linger with you long after I'm gone, baby...trust me."

It was sweet, floral, tangy and intoxicating all in a single aroma, enough to make the ursine salivate and silently wish for more of it.

The feel of those juices on the tip of his cock immediately erased that desire, taking his focus back to the moment of truth; destiny and a lusty feline were sitting at the peak of his member, allowing it to spread her folds just slightly.

As if her petals were kissing his tip, she worked her hips from side to side for a brief moment, wanting him to remember well the little details of his first time just as much as the inevitable finish.

"Is...t-this it?" he had to say something, but in the heat of the moment, he could scarcely find the words to ask her a question, much less compliment how heavenly it was to be enveloped by her womanhood. Inch by inch, complete warmth and silky wetness surrounded him from the tip, further and further down his shaft until she was sitting fully in his lap, resting right up against the pudge of his tummy. "O-oh...oh my God...t-this..."

"It's pretty wonderful, isn't it?" she asked, not afraid to be arrogant about her body and skillset as she clenched him, her inner muscles giving him a treat that few women would be able to imitate. "And you feel pretty damn good too, big guy...you should come back again when you've got a little more experience. I'd love to see what you can do when you figure out how to move those hips..."

"Should I be?!" he started to panic, only to feel his further concerns silenced by her palms gliding over his cheeks. She leaned in close and pressed a brief kiss to his lips, just as her hips began to roll back and forth, keeping him buried within her passage for the wettest ride he'd ever known.

Another quick, teasing kiss was taken from his lips, drawing him closer to her but never giving him the full, deep exchange he expected. "You should do whatever you want, Travis...if that means trying to pump into me, go ahead and try it...learn everything you can," she offered. "Or...if you want to just sit back and enjoy the ride, well...I'm certainly not gonna blame you for that."

Being given a choice in the matter was a terrible thing for an indecisive virgin, but she'd taken care of half that problem for him, and just knowing it left him to gasp for a moment. He looked down the valley of her body, past the brassier of black that hugged her chest to the field of her slender tummy and the softer fur of white that rested atop her pubic mound.

He saw only the peak of her clitoral hood as their bodies met; everything else was locked in a blissful union as they exchanged pleasure with each pass of her hips.

She was his own personal slice of heaven, even if she came at a heavy price. The dollars that were spent were the last thing on Travis' mind as he nervously rested his palms on her lower back, keeping her in place and acting as if he'd seen a growing stain of liquid arousal on the front of his pants a dozen times before.

"If I can't s-stop it, should I-

"Just cum inside of me, love. I can't be the sweetest girl in the world without a bit of cream inside of me, right? Gonna n-need your help with that..."

Everything about the experience was so organic from there that Travis had trouble believing he'd paid a dime for the treatment. His mind was a haze, trying to keep up with the endless waves of pleasure that radiated from his body, the scent of their mingled juices as she continued to pump away on his lap, and the sound of her lithe form settling against his own with greater force as the minutes carried on.

He thought his orgasm might be overshadowed by the rest of the act, but he'd never climaxed with the help of another, before.

When he knew he couldn't stop it, his eyes sunk in and his pupils shrank. Panic washed over him again, but before he could protest or cry out, Cassandra stole his breath a final time with the kiss that he'd been expecting.

Paws locked in around her lower back, cupping her ass and forcing her body to thrust down faster as orgasmic thrills pushed Travis into a preview of what a lover he could be, with a little more experience. His hips bounced up rapidly with the thick, heavy pulses of his cock as a hail of seed spilled inside of Cassandra, soaking her passage all the way up to her womb and coating her petals as the excess began dripping back out, soaking right over the cushions of the couch.

"Mnnn! Ahh! Ah...C...Cass..." he tried to moan through her lips, but she refused to let him break the kiss, even when she was grinning against him.

She didn't mind hearing her name at the last moment, though...as much as her scent would linger with him, she'd hear his voice over and over again in her dreams that night, as if he was calling out to her for a second round; a second chance to prove himself.

Will you come back, Travis? Or did you get everything you needed from me...?