First Time

Connor heard a light knock on his bedroom door, the 15 year old opossum glancing up from his bed, his laptop laying on his belly. The voice of his mom came from beyond the door, 
"Honey, we're leaving, I left a little money for food and such on the kitchen table. Have fun, but please have the house still left standing by the time we get back! Bye!" 
"Alright, see you later mom!" 
The boy perked his ears up and listened closely as both his mother's and his dad's footsteps retreated down the stairs, growing more distant until finally the front door opened and closed, the family's car starting up and pulling out of the driveway soon afterwards. With the house left all to himself for the whole weekend, Connor pushed his laptop off and hopped up from his bed, sneaking out of his room. It wasn't very common for both of his parents to leave, especially not for multiple days in a row, and he wanted to take advantage of the rare situation. He wasn't entirely sure of what he should do however, a few rather radical ideas floating in his head, none of them being anything that he'd ever done before. The possum hadn't had too much luck with the ladies so far, his virginity still left intact no matter how hard he had tried in the past, but now he was outright desperate to finally get a home run and pop his cherry, the only obstacle being to somehow find a girl willing to do the deed with him. The teen wasn't too unpopular at his school, but he didn't exactly have many friends of the female variety that'd eagerly run over to his place and drop their panties for him with just a quick call. The dating scene around his city wasn't something he was familiar with either, and he probably wouldn't have been able to snatch a woman willing to sleep with an underage boy, at least not quickly enough to meet up before his parents had returned from their trip. That all left Connor with just one option that he could think of, an option that he had mulled over in his head over and over, dismissing it several times before always returning to it in the end, an option that he wasn't entirely comfortable or happy with, but one that he had to take in the end. 

The boy slipped back upstairs, picking up his laptop and clicking open an incognito page on his browser, typing in the name of a page that he'd managed to dig up a few months ago. The page loaded up with rows and rows of women, their names, quick descriptions, and a few lewd images of each spread out on the gaudy site, the prices of the women listed right underneath. Prostitution was a rather desperate branch to grasp for, and Connor certainly would have preferred something a bit more intimate for his first time with a lady, but the boy didn't feel like he had many other options after waiting around for so long. The page listed out all of the hookers working in his city, listing out their prices and what they were willing to do, each ad vying for his attention. He browsed the site for a few moments, trying to imagine himself with each of the women, looking for someone who would be just right for his tastes while still being available that night and in his price range. He eventually narrowed it down to just a few candidates, eventually picking a canine that caught his eye, the woman almost twenty years older than him. He sent the prostitute of his choice a message on the site, giving her a time and a place before setting his computer down on the bed, standing up and pacing around nervously. The boy was very close to grabbing the computer and deleting his message, doubts flooding his mind as he sighed, his t-shirt sticking to his back as sweat soaked into his fur. Just before he gave into his second thoughts, the laptop pinged with a notification of a reply, the opossum jumping down on his knees in front of the bed and pulling the computer in front of him, his heart beating as he opened the message, half of him hoping that the prostitute wouldn't be able to accept his proposition. He quickly scanned the reply, seeing that it was a confirmation, the opportunity to back out now officially behind him. Panicking even more than before, he stood up and breathed slowly, simultaneously excited and terrified. He didn't know what he should be doing to prepare, or if there even was anything he was supposed to be doing, the cub frozen still in the middle of his room. His anxieties quickly morphed as he thought to how well he might perform with it being his first time, not wanting to utterly embarrass himself in front of someone who had slept with a legion of other men before him. Deciding to make sure that his performance wouldn't be an issue once the time came, Connor quickly jogged into his parent's room, circling around to his dad's side of the bed and opening the nightstand drawers, remembering seeing something there that might help him keep his lower half active though the night. Pulling out a small pack of light blue pills, he popped one out of the blister pack and held it in the palm of his hand for a few seconds, finally shaking his head and shoving it into his maw, swallowing it down dry before sitting down on his parents' bed, trying to calm down while staring at the clock on the wall. 

Rebecca gave her hair a few final touches as she smiled at her reflection, puckering her lips and applying some deep crimson lipstick, the border collie making sure that she was up to snuff. She had dressed up rather casually for her newest appointment: a blue top and tight jeans showing off just a tiny bit of her white belly, a pair of black panties hidden underneath her pants, the faint outline of her nipples visible through her shirt, the canine having chosen to go without a bra. After being in the business of pleasing men for many years now, Rebecca had become rather talented at being able to sniff out what sort of an experience her client would like just from a short conversation, even a single message asking for an appointment giving her a treasure trove of hints as to how best to service her customer. Her current client seemed rather shy, probably his first time ordering a prostitute, maybe even his first time overall based on his young age, those sorts generally preferring a more relaxed experience, dressing up to the tens often making them more nervous. She checked her purse for everything, making sure she had a pack of condoms tucked along with a can of mace, knowing from experience that it was best to prepare for all sorts of situations. Still having plenty of time to make it to her appointment, the dog stepped outside and hopped into her car, heading towards the outskirts of the city, occasionally glancing at her phone to make sure she was still heading towards the correct destination. She didn't know anything about the man he was supposed to meet, only that he purported to be 18 years old and an opossum, the appointment being the first time that she'd hook up with his species. Stopping at red lights, the woman turned her rear view mirror to make sure her look was perfect, hoping to impress her new client and turn him into a regular, repeat customers making up a big part of her income. After making it through the evening traffic and turning into the much more quiet suburbs, Rebecca noticed the house listed in the information given to her, stopping her car a little bit down the road so as not to cause any awkward questions just in case someone spotted her vehicle in the driveway, getting out and walking the rest of the way. 

Connor had spent the last few hours of his evening pacing around, too nervous to stay still in one place for more than a few minutes at a time, his sweaty underwear clinging to his balls. He jolted gently as the doorbell rang, his eyes shooting to the clock, confirming that it was the exact time that he'd been told to expect his escort down to the minute. Psyching himself up, he shook his head and his arms, huffing and panting for a few seconds before taking a deep breath, trying to calm himself down. Hundreds of different scenarios ran in his head as he walked up to the door, dozens of scenes of him absolutely embarrassing himself in front of the woman, all the ways that his act might be discovered by someone, his mouth going dry and his head going blank as he grabbed the handle. Rebecca waited patiently at the door, eventually hearing some sounds coming from the other side, the door swinging open to reveal the opossum. He was a fair bit shorter than her, dressed in a hoodie and sweatpants, his hands immediately diving into his pockets and his face going white. She raised an eyebrow for a brief moment, suspicious as to if the boy actually was of age as he had claimed beforehand, definitely seeming a fair bit younger than 18 years old. On the other hand, Rebecca hadn't had much contact with opossums in the past, maybe she simply remembered their species being a bit bigger. She smiled warmly at the teen, knowing from his face that she would definitely have to be the one to make the first move unless she wanted to stand out in the cold for the whole evening, 
"Hey there cutie, I'm Rebecca, I think you were expecting me~?" 
"Uhh… yeah… yep. Come… come on inside."
Connor felt his words constantly slipping just as he was fumbling around for them, the canine even more stunning in real life than she had seemed on the site. He had always thought that he'd be more into girls his age, but the border collie definitely made him appreciate the more mature options as well, her chest staring him right in the face, her tail gently brushing up against his chin as she stepped inside. The blue pill he had taken earlier on the day was starting to really work, his nerves having blocked any activity down there until he finally laid eyes on the hooker, his sweatpants instantly tightening up. 

Stepping inside from the fresh air, Rebecca instantly caught a whiff of the cub's strong musk, only gently smirking to herself about it, having slept with many other men in similar states. Connor nervously rubbed his neck, unsure of how exactly he should proceed with the prostitute standing in the living room, 
"So… I'm Connor. Uhh… nice to meet you?" 
Smiling at his smooth talk, the canine quickly looked around the room, the opossum clearing his throat awkwardly, 
"This is the living room, and… yeah…" 
The subject of payment suddenly entered his mind, remembering that he was supposed to pay in advance, quickly pulling out a small wad of bills from his pocket. Most of it was the food money left for him by his mother, padded with some of his own savings, happy to live off of the ramen and cereal that was already stocked in the kitchen for a few days if it meant the chance to finally get laid. He handed the money to the border collie, Rebecca slipping the stack into her purse before smiling at the teen, gently stroking his chest as she leaned against the couch, 
"So, where did you wanna do it, big boy~?"
"Uhh.." 
Helping him along, she listed out a few options, 
"We can just do it here, or in your bedroom. The bathroom is also nice if you wanna make the cleanup easy."
"Sure, the… bedroom sounds good. That's… here." 
She followed the possum upstairs and into his bedroom, his musk pushing into her nostrils even stronger in there, the tiny room not having been aired out in quite some time, the still air reeking of the numerous jerk off sessions. The walls were plastered with different posters, half of them of obscure bands and the other half of scantily clad girls, the ones with the eye candy strategically pinned right next to the bed. She rolled her eyes, chuckling to herself at the state of the bedroom but staying professional nonetheless. Connor was far too anxious and horny to even notice his own musk, unsure of whether he should be trying to hide the growing erection in his pants, still feeling awkward about being so blatantly aroused even though she was there for that exact purpose. 

Rebecca sighed softly and set her purse down on a chair, smiling as she turned to the shy boy, 
"Now, what did you have in mind for me? I'm all yours for the night~" 
Stumbling over his words, the teen blushed and looked away, tongue tied and too afraid to say what he was after. She smirked, the cock visibly throbbing in his pants doing more than enough talking for him, gently pushing him to sit down on his bed as she took a step back, 
"Well, let's just start with this, shall we~" 
The canine grabbed her shirt with both hands, slowly pulling it over her head, revealing her lack of a bra. Connor's wide eyes were glued to the hefty set of tits, his gaze tracking her chest up and down as they bounced and jiggled around, his mouth hanging open in amazement. Rebecca giggled at the boy's ogling, very happy to receive the occasional confidence booster in her line of work, licking her lips and winking at him as she popped the button open on her jeans, shimmying the pair down to her thighs. She slipped both of her thumbs under the band of her black panties, biting her lip as she gingerly pulled the underwear up, bunching the silky fabric right between her pussy lips, a small bead of her juices glistening right at the bottom of her slit. Enamoured by the sight, Connor couldn't help but to moan and grab at his stiff cock through his sweatpants, the blue pill making his little friend work overtime, the outline of his cock visible from his crotch all the way down to his thighs. The border collie lowered both her panties and her jeans down, slipping them off and draping them on the back of a chair. Now completely in the nude, she smiled seductively, turning around to give the cub a good view of her entire body, bending over with her tail hanging high in the air as she reached back to pull her ass cheeks apart, showing off both her tailhole and her pussy to him while slowly wiggling her backside back and forth, 
"See anything that you like~?" 
Nearly forgetting to breathe as he enjoyed the show and with what felt like every last drop of blood draining to his lower half, the opossum could only nod and stare, drooling hungrily. 

Rebecca reached into her purse, pulling out a condom and holding it up between two fingers, grinning as she shook it around, 
"Why don't you get those clothes off and throw this on so that we can get into the fun~" 
Eager to obey, Connor quickly pulled off his hoodie and his t-shirt, throwing both aside before ripping his sweatpants down, revealing his bulging boxers. The dog couldn't help but to gasp quietly as he pulled his underwear down in a hurry, his full girth flopping out onto his lap, over ten inches of thick shaft pulsing and oozing precum, most of his pubic fur completely soaked in a mixture of pre and sweat. Rebecca was very impressed with the boy's size, never having guessed that such a small thing could be packing such a huge surprise, her eyes glimmering with newfound interest. Even after getting to handle the members of so many other men before the opossum, she couldn't think back to many others that would have beaten or even matched the teen in size, with the possible exception of a few of her equine clients. Connor tossed his pants and underwear to the floor, sitting on his bed with his cock pointing up towards his face, a slight blush on him as the older woman handed him the small wrapper, 
"Here you go, stud~" 
He gulped and tried to rip the wrapped open, struggling to get a good grip with his fingers stained with slippery precum, fumbling around for an agonising few seconds before finally managing to wrestle the condom free, pushing the small ring against his tip before starting to roll it down his shaft. The opossum hadn't had much experience with using condoms before, never having a good reason to wrap his member in the past, slightly unsure of if he was applying the rubber to his length entirely correctly. The issue was only compounded by the fact that the condom was a fair bit tighter than it should've been, Rebecca having only brought along a single size of protection, the boy's girth preferably taking a slightly larger condom than the average. Not wanting to seem like the virgin that he was in front of the incredibly hot canine, Connor did his best to covertly hide the issues he was having with fitting his slab into the rubber, hunching over and gently turning away from her. She wasn't too focused on making sure that the boy was properly applying the condom however, her chest puffing up as she moaned and rubbed a finger between her pussy lips, impatiently waiting for her opportunity to get her hands on her client's big package, completely losing herself to the moment and forgetting to stay as attentive as she usually was when it came to practicing safe sex. 

With the condom wrapped tightly around his throbbing member, the tip quickly filling up with precum, Connor turned back towards the woman, trying to keep his eyes at her face even as the rest of her naked body kept distracting him. Rebecca stepped forwards and got down on her knees, excited to finally play with the well-endowed boy, wrapping her hand around his base as she leaned her muzzle closer. The odour of sweat stung her nose as she got right between his thighs, forcing her to hold back from immediately swallowing the whole shaft, the strong scent requiring some time to get used to. She slowly stroked and squeezed his cock while carefully inhaling, snickering to herself about what a shame it was that she wouldn't be able to just breathe through her mouth for the duration of the blowjob. Getting acclimated to the salty stink of the teen's sweaty lower half, she finally slipped the tip of his cock into her maw, one hand holding his soaked balls as she ran her tongue up and down along the shaft, feeling the gentle ribs of the condom bumping up against her lips as she plunged more and more of the gigantic rod down her muzzle. Connor splayed his legs open, stretching and straining them as he arched his back, his mouth wide open in a silent scream before he finally moaned loudly. The feel of the border collie's mouth was absolutely divine, even with the condom in the middle, even his wildest dreams of what a blowjob might be like never reaching as high as he was feeling. Swept up in the moment, his erection reaching almost painful levels of hard and a rush of hormones pumping through his veins, the boy quickly lost almost all control of himself, planting both of his hands on the back of the canine's head and shoving her maw down against his cock, ramming it right down her throat. Not having expected the burst of enthusiasm from the shy teen, Rebecca's eyes popped open, the bulge in her throat moving about as she tried to pull back, groaning in slight annoyance about not being warned ahead of time.

Connor groaned and clenched his jaw, grinding his teeth together as he kept pushing the woman's face further into his sweaty crotch, his ballsack bumping up against her jaw as her red lips pressed around the base of his shaft, his eyes crossed and his heart beating faster than ever before in his life. Recognising that the boy was only a hair away from prematurely popping his top, Rebecca quickly yanked her head back and her maw off of his dick, wanting to make sure that her client would receive the entire range of services that he had paid for and that he'd have the best possible experience with them all, hoping to guarantee another appointment from him sometime in the future. The canine also didn't want to risk the opossum deciding not to let her have a proper test drive of his impressive girth after getting his fill on just the blowjob, though she certainly wouldn't admit her unprofessional greediness to anyone. Licking her lips and wiping off the excess saliva, she stood up and stumbled backwards, huffing with her cheeks glowing a gentle shade of pink,
"Let's not get ahead of ourselves here, no need to hurry anywhere. I'm all yours for the whole evening, after all~" 
Connor shivered all over, fighting the urge to just grab his cock and finish himself off with his own hands after being left hanging on the edge, only the promise of losing his virginity and the knowledge of how much money he had already spent on the prostitute keeping his hands planted firmly against the mattress, his tail coiled around one of his wrists. The dog spread her thighs and pulled her pussy lips open to entertain the boy while he cooled down for a few moments, cooing softly as she rubbed her clit, her hungry eyes fixated on his pulsing cock. She slowly pushed her ring- and middle fingers into her slit, puffing and leaning over the teen as she giggled, grabbing his arm and bringing one of his hands up to her chest, letting him cop a feel of her tits while she fingered herself. 

After letting the opossum cool down slightly for a few minutes, the pair both very anxious to get properly acquainted with each other's bodies, Rebecca moaned softly as she lowered herself onto the boy's lap, pushing her forehead against his and her chest right up to his muzzle as she smiled, the heat radiating off of her slit teasing his length as she whispered into his ear, 
"Let's get to what you've been so patiently waiting for~" 
Her words took the breath right out of Connor's lungs, his hands squeezing and bunching up the bedsheets while he just barely whimpered, watching the canine getting back off of his lap and crawling up onto his bed. Rebecca got down on her hands and knees, pointing her flank right at the boy before flipping her tail out of the way, perfectly presenting her succulent spade for him. She had chosen the position for him, thinking that doggy style should be a nice and easy option for his first time while also giving him some privacy to do his business behind her, the older woman's gaze having the risk of putting some pressure on the shy teen. Scrambling to roll onto the bed, Connor quickly got into position behind the border collie's backside, shuffling around on his knees with his cock in his hand to find the perfect position and angle to get his tip in line with her pussy, the hooker helping him slightly by pressing her ass down to get his crotch to the same level as her slit. Half-panicking and too high off of adrenaline to think about much of anything, Connor squeezed her hips with his free hand while poking his dick against her entrance, feeling the soft lips giving way as he slid inside, his entire length quickly swallowed up by her warm embrace. 

The opossum's whole body jolted from pure pleasure, his fur puffing up and his face glowing red as he thrust inside of the prostitute, officially loosing his virginity in one winded grunt. Hilted up to his balls inside of the dog's pussy, he wanted time to freeze and let him spend an eternity just enjoying the subtle squeezing and clenching on his cock, her walls kneading and pulling on his dick, inviting him further in as more and more precum poured into the taut condom. He knew that he couldn't stay lodged deep inside of her forever though, feeling his orgasm quickly creeping closer with every passing second. He pulled halfway back to slam his slab back into the waiting and begging cunt, not wanting the woman to think of him as nothing except a one pump chump based on his performance. Rebecca moaned and buried her face into the boy's pillow, the musky smell of the covering only stoking the raging fire in her belly as he rammed his huge cock into her pussy again, the girth and the length more than making up for the teen's lack of technique or confidence. She closed her eyes and drooled on his pillow, relaxing her body and letting the boy have his way with her. Connor kept up his hammering, steadily getting faster and more intense as he felt his finish getting near, his fervour making him completely ignore the slightly odd feeling of the condom wrapped around his dick, the tightness and the air trapped inside from his amateurish application causing much more strain on the ribbed rubber than intended. He grabbed her tail and rammed her harder, stars flashing in his eyes as he experienced the most intense orgasm he had ever felt, his lower half still thrusting on autopilot as a huge load of cum filled up the already stressed condom. The boy's eyes shot open with a nervous look as he suddenly felt something changing deep in the canine's pussy, the pressure from the condom around his rod disappearing with a snap. Too deep in his pleasure to stop and check everything out, he simply kept pumping his seed, worrying about where exactly it was ending up sometime later on. 

Immersed in the feel of the thick shaft splitting her open, Rebecca only noticed that something was wrong as she suddenly felt something drooling down her thighs, the quantity much more than the amount of her own juices she would usually leak. The canine peeked under her belly, her face immediately falling as she spotted a flash of white trailing down her leg, quickly pulling herself forwards with a moan as the cock was yanked from her cunt. She spun around onto her back, lifting her legs up to see a huge wad of cum oozing from her pussy, her eyes shooting up to the opossum's dick, the tattered remains of the ripped condom still clinging to his quivering shaft as he squirted the remainder of his load onto her belly. In a frantic panic, the dog jumped off of the bed and squatted down, desperately trying to get the cum out from her with little success, biting her lip as she tried scooping the sticky mess out of her with her fingers, 
"Oh, goddammit, fuck!" 
In the back of her mind, she was well aware that nothing she was doing would work, the cub's strong and virile seed already intermingling with her eggs. Connor hunched over, weak from his orgasm, too shocked to do more than huff as the woman pushed out his load onto his carpet, a shaky hand reaching down to slip off the remains of the broken and soaked condom from his shaft. She glanced at the young possum, glaring at him in annoyance, 
"Seriously!? You didn't feel or see that?" 
"I… I don't know… I guess I… I just…" 
She rolled her eyes and groaned, wiping her sticky fingers on her side, realising that she couldn't put at least all of the blame on the inexperienced boy. Taking a breath and calming down slightly, she rationalised that it was unlikely for a single accident to result in anything serious, grabbing a napkin from the box he had sitting on his nightstand to help in the cleanup effort,
"It's… it's fine, just… please be a bit more careful in the future, okay?" 
Rebecca grabbed her clothes, pulling on her shirt and pants, leaving her wet panties on the chair as Connor stumbled up to see her off. Still panting, he wasn't quite sure how he should be saying goodbye to her, his first instinct of a handshake seeming far too formal for someone who he had just cum inside of moments before. The border collie surprised him with a hug as he was still trying to decide, giving him a kiss on the cheek and leaving a faint print of her crimson lipstick as she smiled softly, 
"If you ever feel like burning off some stress again in the future, you know where to find me, day or night~" 
She winked and picked up her purse, slipping out of the boy's room as he flopped back onto his bed to take a breather. Rebecca felt more cum leaking from her spade, a slightly uncomfortable look on her face as she walked outside and into her car, unaware of what was going on deep inside of her womb, the opossum's seed hard at work.