Chapter 23: A Series Of Firsts

Room 21, Roadside Motel, Baltiney, New York...

 The moment the key fit into the lock Ken's busy hand quickly twisted it, opening the heavy dark green door with black metal numbers, that blocked them from the view of the outside world, Dean seemed to be a bit more nervous than he'd been used to being when he had elected to entertain a client as he walked into the motel room behind Ken holding his share of the bags from their trip to the diner to do something about his rumbling stomach. Ken had brought a few things inside and sat them on the small round table that had been on the far side of the room with square-built armchairs surrounding the round dark brown table. He turned his attention to loosening his tie and tossed his suit jacket into one of the empty chairs after sitting down the bag with the food in it onto the table.

He had seemed to have his mind on something else as he moved toward the television and turned it on flicking through the channels for a moment before turning down the sound and stopping on the news broadcast. He tossed the remote, which had been a long black rectangle with various buttons, onto the bed.

Dean had taken a moment to get a look at the place with the lights on, the carpet had been dark brown and the bedding a strange orange color, the sheets had been white and the drapes that lined the large rectangular windows had been orange as well. It had not been a very ideal choice for coloration but it was useful for what they were intending when they arrived the colors of the bedding and drapes would be little in the way of a distraction.

Ken seemed to pace a bit before turning his attention to Dean.

"You go ahead and eat, make yourself comfortable whatever you need to do to relax," he instructed him. "I gotta make a run real quick and I'll be back within half an hour, don't leave this room because I'm taking the keys with me and you'll be locked out otherwise."

Dean nodded in understanding as Ken took a few moments to look into his deep blue eyes before heading out of the front door. It closed tightly behind him, locking it in place watching him go, Dean followed toward the window where he took note of Ken climbing into his car and taking off rather quickly.

Once Ken's car had disappeared, Dean had been once more reminded that he'd been very hungry with the scent of the food mixing with the stale room air and his continuously growling stomach. Ken had said he'd be back in half an hour so Dean settled for eating and after he had finished he had elected to take full advantage of being in a motel room by taking a long hot shower.

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Room 21, Roadside Motel, Baltiney, New York...

Ken Ryker had pulled back up to the roadside motel after having swapped out his car and purchased a few items last-minute items from the store. He had been of the mind to have a few drinks in time to go with the festivities he had planned for himself and Dean of course. He made it back to the room in the allotted amount of time and put the bag he'd just gotten on the table. He'd taken note that Dean had finally eaten and turned his attention to the sound of rushing water from the shower. Ken locked the door to the room and took a few moments to pour himself a cup of the booze he brought with him and casually sipped on it while he made himself more comfortable, discarding his dress shoes first, then his suit slacks, and white button-down shirt as he sat clad in his solid dark blue boxershorts and a white t-shirt.

It had been quite some time before Dean had finally gotten out of the shower clad in only a white drying towel that had been wrapped around his lean pale waist, he found himself a bit caught off guard noticing Ken sitting in the dark with a cup of booze in his hand and his eyes a bit glossy from his drunken state.

Water had still been dripping from Dean's peroxide blond locks as he moved across the room once more recalling why he and Ken had come to the motel in the first place. Ken looked up at him holding his breath involuntarily as the half-naked lad slowly approached him. He could tell he'd been nervous as Dean's small hands trembled as he moved them along Ken's bare thighs. The older man's thick cock had tented his boxers quite easily nearly bursting free at the instant of Dean's soft fingers moving along Ken's knees.

Dean got down on his knees before Ken who remained sitting on the edge of the bed as he watched the younger lad with rapt fascination. The wet blond lad slowly fished Ken's thick cock from his boxers, his blue eyes widened a bit when he noted how long it had been when unrestrained causing Ken to smirk at the notion of surprise that filed across Dean's youthful face.

The older man let out a grunt when Dean's warm wet hands began to trail along his bare cock causing him to hiss when the lad gently ran his tongue over the tip making Ken all the more crazy for him. It had been Dean's turn to smile when he saw how eager Ken had become just as he began to fit the older man's massive cockhead into his warm waiting mouth.

Another grunt escaped Ken's lips as he reached down and ran his fingers through Dean's water-slick blond hair as the lad's lips closed around the thick shaft. Ken had normally not been a fan of having his cock sucked even by a woman but there was something about how Dean's warm wet mouth felt against his bare skin that Ken couldn't bring himself to be against.

It hadn't been nearly enough to quell the older man's lust but it had been a start in igniting it further if that had been the boy's plan. Dean had been stunned at how large and heavy Ken's cock had been when compared to the other men's cocks he'd been forced to suck during his captivity and beyond while working the street corner. He couldn't exactly wrap his mouth around it completely and his jaw had begun to get a bit tired as he sucked the older man who had begun bucking his hips into his mouth.

The sensation of Ken's rough hands moving through Dean's hair had been rather nice as he continued to indulge in the strange aspect of affection. Not many people had opted to treat the lad with affection, not even during sexual activity but Ken had been different at least in this instance, he had certainly been well above the bastards that pummeled Dean's pale ass when he'd been heavily drugged and left him to his fate with little to no regard for how it would affect him.

Dean's mouth being on his cock had only intensified Ken's resolve to be inside him and he ordered him to stop for both of their sakes. Dean obliged looking back up at Ken as he slowly let the older man's cockhead slip from his lips making Ken groan as he suddenly lifted Dean off the floor and slammed him back first onto the bed, moderately startling him as he demonstrated just how strong he'd truly been in the wake of their shift in dynamic.

Ken pulled Dean to the edge of the bed and gently removed the towel that had been around his slender waist revealing his naked pale body and the lad's smaller pink cock standing on end as much as Ken's had been when he took control.

Ken smirked as he elected to wrap his rough right hand around Dean's throbbing cock making the lad moan out loud and buck his hips upward in a bid to drive out more friction from the older man's grip. Ken had never actually known what it was like to have sex with someone like Dean, let alone another male but he had wagered Dean had been a slave to his cock just as much as anyone had when they came into the world.

The older man had not been in any way compelled to put the lad's cock in his mouth as that had been a step too far in his already depraved mind but he continued to jerk Dean's cock as the lad squirmed and moaned in the center of the bed beneath him.

Ken had been amused by how easily Dean had reacted to having his cock pumped and how easily he'd cum coating the older man's right hand as he gasped for breath whimpering with need as it pulsed in Ken's firm grip. He had watched Dean react with fascination until he noticed that Dean coated his hand and belly from the light spraying but there had been a different kind of wetness coming from between the whimpering lad's slender pasty thighs increasing as Ken held the lad's spent cock in his hand.

The older man held off remarking how the lad had a hair trigger when it came to his release as he further investigated the new source of the leaks. Some careful probing had led to Ken finding out that Dean had been quite different from many of the young teen boys his age given that he'd been born with a fully functioning vagina.

Ken looked up at the rather nervous and red-faced lad for a moment with an arched brow then smirked rather wickedly. He had not been all that different from the girls Ken had bedded and as a result, the older man had been more than confident as he leaned his head down and began lapping at the slickness that oozed from the lad's hidden sex.

Dean had nearly convulsed as he felt Ken's long wet tongue invade his hidden sex lapping at his slickness with ease as he moaned and squirmed in bed his cock still gripped by Ken's firm right hand as he arched his body to get away from the overwhelming sensation of Ken's licking.

Ken looked up at him, his handsome face glistening as he winked and went back to lapping at the lad's slickness a few more times before noticing how unhedged he'd become his cock spurting again and again as Ken continued to grip him.

"Wet pussy, my favorite," remarked Ken as he continued to lick Dean and make him moan and whimper as he gripped the bedding below him helpless against Ken's tongue and hand toying with his body through rapid release after rapid release.

Ken let up after the fourth round allowing Dean to catch his breath in the wake of the overstimulation as he watched him pant and squirm amid the bed sheets. Ken had been harder than he'd ever been as he pulled off his boxer shorts and discarded his t-shirt leaving him completely naked as he stood at the foot of the bed, his long thick cock jutting forward as it led the charge for the warmth it sought since their association began.

Dean had still been reeling from the sensation of his recent releases as he felt Ken slowly climb onto the bed splitting his thighs as he inched between them the slickness of the lad's hidden folds coming into contact with Ken's thick cockhead as he began to ease his way past them. Realizing what Ken had been after and that he'd been bare Dean attempted to rouse but had been held down by Ken's free hand being on his pale bare chest.

The booze and arousal had taken their toll and Ken had been one track as far as his mind had been concerned, he thrust forward just as Dean attempted to stop him his small hands pressing against the larger man's bare chest as the sharp pain of Ken's cock spearing Dean's hidden barrier and shattering his virtue had radiated through the lad's body causing him to cry out in pain and his eyes to water as Ken's thick length continued to invade him.

"WAIT....OW!" hissed Dean the tears coming more frequently as he bit his bottom lip in the wake of Ken thrusting in deeper. "I...I'm a virgin..."

Dean managed to get out as Ken stopped mid-pump as he looked down at the trembling naked pale lad whose body had tensed in the wake of the intrusion between his thighs.

Ken noted Dean's cascading tears and sighed as he attempted to steady himself dispute wanting so badly to thrust deeper as the tight clenching had felt good on his wayward cock.

"Fuck...now you tell me?" growled Ken as he leaned his head down against Dean's. "Baby I can't stop now I'm in tight hot pussy and pulling back out ain't an option."

"C-Can't you just stick it in my ass?" asked Dean still tense from the pressure between his legs. "That's the way I've fucked before."

"No can do...I'm not fond of ass so much as I am pussy, especially a pussy as tight and wet as this one," replied Ken honestly. "Besides I'm already in and the only way I'm coming out is if my dick's been drained balls deep."

Dean grunted.

"C-Can you at least go slow...you're not exactly small and it hurts my pussy when you drill in." whimpered Dean.

Ken groaned hearing those words only seemed to intensify his lust as he found himself once more inching forward making Dean scream out and more tears flow down his pale cheeks.

"Fuck you feel so good baby." groaned Ken struggling against his primal urge to pound Dean's tightness until his thick cock exploded inside him. "I tell you what, I'll try it out but you gotta let me fuck like I want, bite down on my shoulder if you can't take the pain, it's what the other girls did when I ended up fuckin' a virgin."

Dean had been even more nervous hearing this.

"I'm to any of those other girls," he said terrified of what had been in store for him due to how big Ken's cock had been.

" I know that but the best I can do is try not to hurt you, but believe me the sooner you let me fuck you the sooner you'll be begging me not to stop," replied Ken.

Dean sighed as he looked up at the ceiling of the motel. So this was what it felt like for him to lose his virginity to a man like Ken. He had been saving himself for something of note but Ken had other ideas that could have been worse, those that he'd him captive could have discovered his last aspect of virtue and stolen it, Ken had been a pretty decent man overall even when drunk and driven by lust, at the very least he attempted to be.

"You ready?" asked Ken meeting Dean's blue eyes amid the semi-darkness of the motel room.

Dean took a deep breath and nodded as the tears continued. Ken suddenly kissed him on the lips and leaned into his ear.

"Once this is over I promise you'll be begging for me to fuck you," he said softly in the lad's ear his deep baritone voice dripping with lust. "Right now, Daddy's gotta pop your cherry baby."

Upon hearing this Dean gasped when Ken thrust deeply into him bursting past his barrier as he began thrusting inside the lad jolting his smaller pale body along the bedding making him whimper and moan as the thick wooden brown-colored headboard beat against the motel wall.