#virgin!john

The only perk to working on his own being that when he was finished, the horses gave a convenient cover for him to find a quiet place to sit in the fresh grass and read.

This was where Dutch had cornered him. He had jumped when the older man bellowed his name. Sure he was in trouble for slacking off although he had finished all his usual chores. With Arthur absent he supposed he was expected to pick up his slack as well.

He was surprised to be invited on a trip in to town. It was uncharacteristic of Dutch to leave camp for petty business. The big dog usually only taking to the wagon for real jobs that had been meticulously planned.

This alone made John nervous. But coupled with the fact that Dutch insisted they go ‘just the two of them’ had him beside himself with worry.

“Where are we goin’ though?” He asked for the second time. Using the distraction of picking at the dirt under his nails as a cover in case the older man ignored him again. He tried to calm the anxious bouncing of his right knee, resting his forearm on it as he studied his hands. 

He hadn’t had a very good run of things lately. Lots of bad luck on his part culminating in several bad jobs, all his idea. He had cost the gang a fair amount of time and effort for very little gain. He eyed Dutch nervously as the older man hummed in response. He hadn’t been too worried after the first botched job, but after the third he had started to wonder exactly how expendable he was.

“You’ll see.” Dutch replied, an air of mirth in his tone. John frowned, sitting back in the chair and reluctantly deciding the less he knew the better.

They rode in silence, only breaking it to tip their hats and express social niceties to the other passing travellers.

John’s anxiety slowly dissipated as they entered a small town on the outskirts of Oakstead. 

Unless Dutch was planning on selling him at the general store for a few bags of horse feed, he was fairly sure this trip wasn’t about culling him from the gang.

“So what’s the job?” John asked quietly, trying for the third time to get some answers and ease his mind.

“No job son.” Dutch replied heartily, a grin tightening his rosy cheeks and accentuating the beginnings of crows feet on his otherwise youthful face.

“Oh?” John replied, surprised by the older man’s reaction. If he wasn’t confused before he surely was now.

“I have a gift for you.” Dutch stated proudly, voice low as he pulled on the reins and stopped the wagon beside a large building with a saloon like appearance.

“A gift?” John asked warily. “What for?”

“Oh don’t be daft son, it’s unbecoming.” Dutch chuckled, slapping John’s thigh in a paternal fashion as he stood and began to climb down off the wagon. John followed suit, walking around and meeting Dutch at the back where the older man placed a solid hand on his shoulder and gestured in front of him. “Your birthday.” Dutch finally answered when John continued to seem perplexed.

“Oh…” John said again, not really sure what else to say. His birthday had been a few days before. He had almost forgotten himself and didn’t really expect anyone else to remember either. No one had mentioned it at the time, so he had assumed that was that.

“You didn’t think I’d forgotten did you?” Dutch asked, amusement sprinkling his tone. John just shrugged in reply, studying his boots. The only person to ever really take notice of his birthday was Arthur and he had been away a lot lately, hanging out with that Mary woman. He hadn’t seen him in a few weeks, so there was no telling if he had remembered or not, wherever he was at the moment. 

“Well of course I didn’t.” Dutch whispered with a touch of condescension. “You’re eighteen now. Time to become a real man.” He said cryptically, the hand on his shoulder snaking around to grab his arm as Dutch turned them and walked them together towards the front of the building.

John took in the structure, a large double story building with a veranda wrapping all the way around on both levels. The first level was not far off the ground, only about 5 steps but it felt like 50 as Dutch led him up them and he realised exactly what this building was.

“A brothel?” He asked, raspy voice strained as he tried to hide his surprise. Why on early would Dutch bring him here?

“Absolutely.” Dutch answered simply. “Today you become a man.” He explained, giving the younger man’s arm a reassuring squeeze. John swallowed thickly as they pushed through the large double doors. Inside resembled a hotel lobby. A large, spacious room with a desk in the middle and comfortable looking cushioned chairs around the sides. Behind the desk there was a long hallway to the right. He supposed this lead to the rooms the whores took their clients to. On the left there was a staircase leading to the second level and what appeared to be more rooms above them.

He kept his eyes on the ground. Trying in vain to ignore the excited chatter of the women sprawled on the couches. Thrilled giggles assaulting his ears as Dutch bellowed to the woman behind the desk about why they had come. He was beyond embarrassed, shrugging himself out of Dutch’s grasp as the older man explained John’s situation.

“Dutch…” He said hoarsely, begging his Father figure to stop talking. This really wasn’t how he had imagined this day going. He tugged on his arm, pulling the man from his conversation and earning himself a confused look. “I don’t understand…” John said quietly, trying to avoid prying ears. “You’re buying me a whore?” He asked. “Why not just… Get one of the camp girls to…” He stopped, not knowing the polite word for what he wanted to say.

“Oh no.. no, no, no.” Dutch said quickly, shaking his head and pulling John in to a huddle of sorts as he enlightened him to his way of thinking. 

“The camp girls… they’re opportunistic.” He whispered, watching as the younger man raised a brow in question. “This is your first rodeo son. We don’t sleep with our own for our firsts unless we’re talkin’ two consenting adults in an honest pairing.” He explained. “Men can get funny about their first and those women... Well let’s just say I wouldn’t want to see you bein’ taken advantage of as much as I wouldn’t want you catchin’ feelins’ for one of our girls.” He chuckled, petting John’s arm softly.

John hummed in response. “Okay...” He said softly, after it became apparent Dutch was waiting for a verbal answer. The older man beamed, turning him around the face the women on the couches and instructing him to choose one. John shook his head, keeping his eyes averted and waiting for Dutch to take his pick. He was sure it would ultimately be the older man’s decision anyway.

Dutch beckoned a young woman that looked to be in her early twenties. Long blonde hair curled and tied up in fancy swirls. She had a slim face and wide hips. Small breasts that sat nicely inside her corset without bulging. John smiled at her uncomfortably, feeling his face flush as she flicked her skirt to the side and held it there with a hand on her hip. Her luscious thighs on display as her bloomers only spanned down just below her privates.

John cleared his throat as the woman held out her hand. Dutch gave him a nudge forwards and he moved, fumbling his step as he reached out and took it. He had never seen a woman in such a state of undress before. He was ashamed to admit how fast he had gone from reluctant patron to willing client.

He glanced back over his shoulder as the woman led him away. Feeling somewhat uneasy as Dutch gave him a wink before turning back to the Madam and striking up conversation anew.

As she pulled him up the stairs John wondered whether or not Dutch was going to indulge himself or if this was purely ‘business’ to him. It had only been a year or so since Annabelle had passed. But he suspected that honestly it would not have mattered if she were alive anyway. Dutch was very selfless in a lot of ways. But he was not a gracious partner, that much had been clear to the boys growing up. The way he cycled through women bordered on sociopathic. Annabelle was the first one he had kept around for more than a year and he suspected even she would have been cast aside eventually had she not been killed.

John was shaken from his thoughts as the soft hand he had been holding slipped from his grip. The lady stood in front of him, holding open the door to a bedroom with her back as she gestured for him to move inside. He did as he was instructed, entering the quaint little bedroom and looking around in surprise.

He had always imagined the rooms in a brothel to be fairly simple. Dark and dingy. One small bed with a dirty mattress and maybe a side table if the establishment would shell out for it. But this was beyond his expectations. There was a large plush looking bed pushed to one side. The covers looked to be expensive, a deep red colour laced with gold. There was a wooden vanity table with intricate carvings around the edges on the opposite wall and a coffee table with matching markings in the middle of the room surrounded by single cushioned chairs. The floor was wooden but most of it was covered by a large rug that looked soft to the touch.

He turned to the woman, making to speak as he suddenly felt out of place. He had never stepped foot in a room so fancy without the intention to rob it blind.

The woman shushed him before he could talk, closing the door behind herself and reaching out to place her hands on his waist. He exhaled sharply at her touch, hands subconsciously moving to cover hers as he found his eyes trained on her breasts.

One of her hands left his waist and came up to rest on his cheek. She made strong eye contact with him as she trailed a thumb over his lips, letting him know talking was not necessary. He nodded, eyes moving down to look her over once more. He swallowed, lust clouded eyes roaming as his cock strained painfully against his fly.

Silky palms slid in to his own as she took both of his hands, leading him across the room to the vanity. He questioned her with his gaze as she leered seductively. Her hands moved slowly, coming to rest on her own thighs before taking hold of the edges of her skirt and pulling the split at the front open wide so he had a good view of her bloomers.

Her thumbs hooked under the elastic and she wiggled her hips slowly from side to side as she pulled the fabric down to reveal soft curls the same shade as her hair.

John’s breath stuttered as he watched her remove her pants. His right hand sliding slowly down his front and coming to rest on his eager erection. He palmed it once through his jeans, a huff of breath leaving him as some of his frustration was momentarily relieved.

She ignored him, her hands coming to rest on her breasts before starting work on the fastenings of her corset. She untied it seductively slow, one ribbon at a time; letting the fabric start to sag to the sides to reveal her chest yet not quite enough for it to melt away from her body completely. 

John squeezed himself, baser urges taking over the rational portion of his brain as he let out a small moan. He never imagined he would lose his virginity in this manner but he was here now. He figured he may as well try and make the most of it.

The silky fabric fell away to expose two rosy buds and John’s breath hitched at the sight. He thought she was gorgeous but he felt it wasn’t right to tell her.

She stepped backwards, hands pressing on the edge of the vanity as she used it for leverage to jump up on to it. She shuffled backwards, letting her legs slip open and moving her skirt out of the way so John could see her centre.

She beckoned him forwards, smiling to herself as he unconsciously licked his lips. He stopped a foot away from her, making her giggle as she reached out to grab his arm and pull him in between her legs. He lurched forwards in surprise, nerves unsteadying his footing. 

“Um…” He whispered, not sure really what he was going to ask as she shushed him once more. He closed his mouth, letting her take the lead as her hands roamed over his firm chest and down lower to unlatch his gun belt. It fell to the floor with a clunk and he felt his vision darken momentarily as she made her hands busy unfastening his jeans.

“Huh…” He huffed excitedly as her fingers brushed against his cock through the fabric. She smiled to herself, making him gasp and moan as she freed his erection and began pumping it instantly.

“Fuck… fuck…” He whispered under his breath. Any other words a foreign concept to him as skin ran along skin, making him squirm. Expert hands teasing him in a way he had never experienced until his already slick member was visibly dripping on to the floor.

She stopped her ministrations, bringing a hand up to his face and taking a hold of his chin as she encouraged him to look at her. She leaned back against the mirror and swung her legs up to wrap around his waist. His hands instinctively move to the outside of her thighs and she encouraged him to manoeuvre her however he pleased.

He obliged, slipping his palms towards the underside of her legs and pressing forwards. She unwrapped her feet, letting her legs be pressed towards her chest, opening herself up to him.

He stared down at her, breath faltering at the sight of his dripping cock just inches from her centre. It twitched eagerly, making him bite his lip in anticipation.

He looked to the woman for guidance, not sure where he was meant to go from here. She took his queue and reached between them to guide him. He gasped as her hand grasped his shaft firmly and she pressed his tip against her entrance. His lip quivered involuntarily as he slowly pressed forwards, her wet heat engulfing him and sending sparks of pleasure coursing through him. He groaned aloud, all sense of shame leaving him as he used all of his self restraint to stop from thrusting forwards roughly.

He paused after sheathing himself fully. Closing his eyes and willing away the first stirs if orgasm by focusing on keeping his knees from buckling. It really was like nothing he had ever felt in his life. He had never been so close to coming undone with so little effort before.

He drew back slowly, a shaky breath leaving him as pleasure curled in his stomach.

“Fuck.” He muttered simply, ignoring the smirk the word elicited from his bedmate.

He stilled himself, body trembling with the effort of holding back. Already flushed cheeks reddening with embarrassment as he breathed open mouthed; eyes locked on her breasts. He clenched his teeth, jaw locking as he thrust in to her for the last time. Eyes screwed shut and hands tightening on her thighs as orgasm rocked through him. A strangled grunt the only sound he could managed as he spilled himself inside her.

He paused awkwardly, head hanging low as he struggled to control his trembling muscles and catch his breath. He had never experienced an orgasm quite so intense in his life. He understood now why men would kill for the chance to bed a woman. Why the older men in the camp talked about the urge to fuck and how sometimes it overcomes you so completely that it wasn’t to be ignored. Why he so frequently saw men taking their women randomly in open spaces or without even bothering to zip their tent.

He looked up slowly, grip loosening on the woman’s thighs as he stepped back. He fumbled with his fly, tucking his feigning arousal in to his pants and buttoning them up as the woman before him watched with amusement.

“Thank you.” John whispered, voice, hoarse and cheeks burning as he avoided eye contact. He felt a right fool for showing his inexperience. He supposed this was why Dutch had insisted he bed a whore for his first time instead of disappointing an honest woman.

“You’re welcome honey.” She purred, sitting forwards and raising her brows as she caught his eyes flash quickly towards her cunt and then back to the floor. She chuckled under her breath, spreading her knees apart wider, leaning back and raising her hips so he could see his seed dripping slowly from her body.

John’s held his breath. Cock twitching eagerly against his jeans as he stole another glance towards her pussy. He felt himself start to grow hard again, although if he was being honest his erection had never truly gone down. He groaned inwardly at the sensation. Moments earlier he felt as though he could never be more satiated. But now his body was betraying him, arousal coursing through him again. Within seconds his cock was throbbing painfully against its confines once more. This had never happened to him before. Normally it took quite a while for him to feel the urge again after touching himself.

Even if he did try to go again he always found himself too over-sensitised. He wondered now if that was more thanks to his own rough treatment of himself than the fact that he had already cum.

He smiled meekly, unsure what to do now and taking a step backwards towards the exit. He didn’t really want to leave. He wasn’t sure he could handle Dutch knowing exactly how quickly he had expended himself.

The woman’s eyes roamed over him slowly, stopping on his swollen crotch before making their way back up to lock with his. He silently pleaded with her to give him instruction.

“You know honey your friend paid for the hour.” She smiled, sensing his hesitation. John frowned, not catching her drift as she leered at him. The gang always joked he wasn’t the sharpest knife in the draw. He was starting to wonder if they were on to something.

“Your time’s not up.” She said slowly, enunciating every word through her southern drawl and making sure he understood. She pushed herself off the table and took a few steps towards him, her vigour taking him by surprise.

He gasped, embarrassed by the sound that left his mouth as she unexpectedly pressed a hand firmly against his erection once more.

“I...” He began. Trailing off as she squeezed him tightly.

“Shhh...” She cooed, her other hand coming up to rest softly on a hot cheek as he stared blankly back at her. He flinched slightly at the contact, having not registered her movement until soft fingers were caressing his clean shaven stubble. 

“How would you like it?” She asked, catching him of guard. “You can take me again if you like.” She offered, both hands moving slowly, eliciting different kinds of pleasure from both parts of his eager body. “Or I’ll have ya in my mouth if you’d prefer.” She stated casually, making John’s eyes widen.

She looked to him for an answer, waiting patiently as he moved his mouth without words, seemingly frozen by indecision.

He had never been taken in someone’s mouth before either. He wasn’t even really sure what the act involved. He had seen it before, from behind. When the older guys would drag him along to town and let the drink get the best of them. They would often end up being seduced by a lady of the night but with barley enough cash to pay their tab, they settled for back-ally blowjobs over renting a room for an hour of fun.

“I…” He stuttered again, hands shaking as he slowly moved them to her hips. “Um… Your mouth… I guess?” He said slowly, more of a question than a statement. He watched her lips quirk at his words. He wondered internally if she was happy about his decision or if she was just laughing at his inexperience.

His breath caught in his throat as she lunged forwards, her warmth pressed firmly against his front, making him shudder as her hands snaked down to roughly grab at his ass. His knees buckled momentarily as her nails dug in to his flesh through his jeans. He wasn’t sure he would be able to stay standing for whatever was coming next.

His companion sensed this, pulling away and suppressing a chuckle at the small whine that left him at the loss of contact. His ears burned white hot as she took his hand and led him towards the bed. Two hands firmly on his chest pushed him backwards, legs bending as his calves hit the mattress behind him. He sat, looking up at her, eyes burning with desire. She used her knee to nudge his legs open before dropping in to a squat in front of him.

She palmed his dick through his jeans, making his hips pitch forwards in to her touch. He stretched out his arms experimentally unsure where to put them, first moving them towards her but then pulling back and putting them on his thighs. He sat uncomfortably, feeling much too business-like for the situation. She looked up at him and smiled kindly. He was so unsure of himself, it was endearing. She didn’t often service men that had any kind of self-respect, let alone control.

She decided to help him out once more, taking his hands in hers and earning herself a puzzled look. She placed them both by his sides and pushed lightly on his chest so he understood to move them back and lean his weight on them. This tilted his hips upwards and gave him a nice view of her working without him having to sit straight upright.

John was grateful, embarrassment slowly ebbing away as he realised she did this all the time. It was her job and she was nothing if not professional. She was being paid to make him feel good. It wouldn’t do to have him be uncomfortable.

He inhaled sharply as she returned to her previous ministrations, one flat palm running firmly over his engorged length as the other slowly tickled along his thigh, encouraging him to relax.

She moved forwards, pressing her nose against him and feeling his muscles tremble as her hot breath seeped through the fabric. She kissed him softly, his erection twitching as she peppered it with affection. Small pecks from base to tip riling him more that he could have imagined. The heat in his stomach ignited and he tilted his hips towards her touch, losing any sense of himself he had previously owned. He moaned, thrusting towards her, begging her to release him from his confines. She smiled against his crotch, giving his thigh a squeeze before moving both of her hands to undo his pants. 

He panted, misty eyes screwing shut as the cool air of the room hit his heated member. The first touch of her hand pulled a mewling sound from his throat. He quickly slapped a hand to his mouth, looking down at her as he had a moment of self-awareness. She smiled reassuringly, taking her free hand and pulling his away from his lips, non-verbally assuring him he had nothing to be self-conscious of.

His eye contact with her lingered as he tried to make her understand him. He looked away from her face, eyes roaming down over her supple breasts and then further to land on her exposed pussy still slick with his seed.

He shuddered once more, turning his attention back to her hand on his dick before letting his head fall back and closing his eyes as he waited for what he understood to be coming next.

The woman gave him  one long pump, using his own cum mixed with her juices for lube. John shook, letting out a small moan that was more of a sigh. She moved forwards, letting her tongue tickle the base of his shaft and making him cry out before licking him firmly upwards. She stopped at the tip, licking her lips and parting them slightly as she guided him in to her mouth. She held her lips in that position, encouraging him to push forwards as he pleased.

John groaned aloud, heat coiling in his stomach. His erection pulsed wildly as he tried to exhibit some self-control and press slowly in to the wet heat. He felt light headed, breathing too fast as she moved her tongue along the underside of his cock. He cried out, hands shooting out to fist in her hair as he sheathed himself roughly to the hilt.

The woman breathed steadily through her nose, it was in her training not to gag when she felt his head hit the back of her throat. She sensed he had paused to enjoy the feeling as well as try and stave off his second orgasm.

She waited patiently, looking up at him in a way that she knew drove the men wild. Half lidded eyes shining, strong eye contact that had them believing she herself was receiving pleasure simply from servicing them.

John saw through his, knowing in his heart there was no way she was enjoying it. But he pushed that aside for the sake of his own enjoyment, reminding himself once more that this was her job.

With that thought he smiled weakly, he had managed to hold himself off cumming long enough to actually enjoy the journey to his next orgasm. He tightened his grip in her hair, holding her in place as he slowly pulled out of her until just his tip remained. He paused momentarily before pressing back in, steady. He groaned in small huffs, open mouth and shaky breath as he kept up that pace. Watching as his cock slipped between soft lips and moaning repeatedly as she moved her tongue in time with him.

He inhaled slowly in an effort to calm himself, heat was rising way too rapidly in his abdomen and he knew he wouldn’t last much longer. He felt her smile around him, looking down at her as she pressed her nose in to his dark curls and swallowed.

“Ah!” John cried, hips jerking forwards in surprise as she milked him with her throat. He trembled, lust clouded eyes meeting hers as he urged her to do it again. She obliged and he decided there was no point in trying to hold off any longer. Pleasure shot through him as he began thrusting in to her, literally fucking her face. Loud moans left him every time she swallowed or hummed, the pulsing vibration making him see stars. He groaned loudly through gritted teeth, eyes screwing shut as he toppled over the edge of bliss. His orgasm hitting him harder than the first, making him swear as he came down her throat. The motion of her swallowing his seed helping him down from his high as he kept thrusting shallowly long after the sensation was over.

He didn’t look down when she pulled away from him, not wanting to see the state she was in and having to take responsibility for potentially hurting her with his eagerness. He let himself fall, back hitting the mattress as he calmed his ragged breathing. He felt the tantalising call of sleep beckoning to him and he knew he had to open his eyes.

He blinked, his vision returning to him slower than he would have liked as he stared at the ceiling before forcing himself to sit up. He watched as his bedmate dressed herself, feeling a weird clawing loneliness start to seep in to his bones as she pulled her corset over her breasts. He frowned, not really sure what the feeling meant but somehow certain he wasn’t supposed to be feeling it.

He studied her silently, leaning back on his arms as she had instructed him to do earlier. She finished dressing, moving to the mirror in the room and fussing over her hair before opening one of the draws in the vanity and fixing her make up.

John sighed softly, the weird emptiness in his chest not planning on abandoning him any time soon. He tucked himself away, before standing and hovering uneasily as he waited to be instructed. The woman turned to him, giving his restless state a once over before furrowing her brows and placing a hand on her hip.

“Did you not like it?” She asked, worry creeping in to her tone as she wondered if he would complain to her Madam. John looked surprised, the question catching him off guard as he scrambled to answer.

“Wha.. No! No, I mean… yes.” He fumbled, shaking his head and moving his hands in time with his words as if it would help her understand. “Yes…” He said finally, feeling awkward. “Yes I liked it…”

She woman chuckled to herself, her smile turning in to a grin as he considered this gawky teen.

“Well good.” She said, laughing softly as he ran his hand through his hair and stared at his boots.

“Thank you.” He said simply, unsure where to go from there.

“You’re welcome darlin’.” She said kindly, crossing the room and reaching out to stroke a soft hand over his cheek before bidding him adieu. John watched her go, exhaling slowly as the door closed behind her. He would remember this day; her; fondly for the rest of his life. 

~

“My boy!” Dutch bellowed as John descended the front steps to the brothel, sweaty hands running awkwardly along his thighs as he tried to act nonchalant. He smiled weakly as the older man pushed off the post he had been leaning on and clapped a strong hand on his back as they began to walk together. “You’re a man now John!” Dutch exclaimed, making John’s face burn as people turned to look in their direction. He was grateful for the gift Dutch had given him but he didn’t feel the need to share it with the world.

He nodded meekly as they reached the cart. Dutch seeming satisfied with John’s demeanour, content that he had made the right decision for the boy as they climbed the wagon in silence.

The ride out of town was uneventful, both men content to sit within their own thoughts, not feeling the need to speak. John was grateful Dutch had the decency to not ask him about his experience. He wasn’t sure he really wanted to talk about it with anyone.

‘Maybe Hosea...’ He thought to himself as Dutch broke the silence seemingly reading his mind. John sighed inwardly. He wasn’t really in the mood for conversation.

“Now we won’t tell Hosea about this will we?” Dutch asked in a way that let John know it was an order disguised as a question. He rolled his eyes. Of course he was not to tell Hosea, for whatever reason or there would be consequences. From Dutch at least. He quietly suspected the reason he was not to tell Hosea was that Dutch would suffer his own set of consequences as a result.

“No sir.” He answered softly, letting his gaze roam out over scenery as a frown furrowed his brow.

He had been hoping to ask Hosea about the strange empty feeling he had experienced after his encounter. Knowing deep down it wasn’t the sort of thing most men felt, it wasn’t exactly something he could ask Dutch about.

“Good man.” Dutch replied casually, his voice a low growl. John side-eyed him at the use of the word ‘man’ as a replacement for his usual ‘boy’. He wasn’t really sure how much emphasis honest folk usually put on sexual experience in relation to becoming an adult. But he supposed it meant something to Dutch so he didn’t question it. After all Dutch and Hosea had taught him to read, write, ride and shoot all by the age of 14. So what exactly did they have left to teach him to signify his transition in to adulthood? Other than how to take to the drink which he had been doing behind their backs since his late teens anyway.

“Thank you.” John remarked after another long silence, making Dutch smile. He had said those words entirely too much for one day.

“You’re welcome son.” The older man said kindly, one hand leaving the reigns to pet John’s thigh lightly. He gave it a small squeeze just above the knee. A Fatherly gesture. “You’re welcome.” He repeated; the last words spoken between them until their return to camp.

End.

If you enjoyed this please let me know! Also check out the other works in the series!

Part 1 - Falling Part 2 - Leaving Part 3 - Pining Part 4 - Hurting Part 5 - Shattering