Running With An Outlaw

2

Samuel followed close behind, but kept a safe distance because Clinton seemed to be a little unstable with how he was handling his horse. Hell, Samuel was handling his horse a little different than he did when he was sober as well. Clint lead the way out of town at a canter, but once the roads had changed to a tree lined trail, he slowed to a trot.
Samuel was silent as they rode, but he could see the brunette glance over his shoulder on occasion. Almost as if he couldn't believe that the dark haired man had actually continued to follow. It had actually ran through Sam's mind several times to take off and leave, but instead he followed. He didn't know if it was his curiosity and attraction for the man, or if it was the alcohol making him want to just crawl into bed with the first man that came along.
Sam watched as they neared a cabin and the brunette just ride right up to a post. He dismounted the grey gelding and looked up as Sam rode up behind. He shook his head with a soft smirk before heading toward the house as Sam dismounted as well, tying his horse to the post.
"You coming?" The outlaw called from inside the house and Sam took a deep, nervous breath before following him into the house.
Clint had kicked off his boots near the door and taken his hat and jacket off, allowing for Sam to look him over with interest.
Clinton moved around the house to light some lanterns for light, which gave Sam the ability to look around from just inside the door.
"Well, come in and shut the door," Clint ordered with a soft laugh. "What? You nervous now?"
Samuel shook his head in response before stepping all the way in and shut the door. "Just don't do this sort of thing," he explained casually as he waited by the door for Clint to finish lighting the lanterns.
"Yeah, I can tell," the outlaw laughed as he moved closer to the sheriff's son, getting close enough that his lips almost touched Sam's. "Let me guess... your first time? I can tell because you're standing as stiff as a board and damn near shaking in yer boots," he added with a smirk and a soft chuckle before moving toward the couch and sitting down with a sigh.
Sam flushed a pale pink and his breathing picked up a bit. "Opportunity just never game around..."
Sam could see Clinton's face soften a bit at the information, and the outlaw simply patted the seat beside him slightly as a gesture to get Sam to come sit beside him.
"You know... I didn't think you'd take up that offer."
"Why's that?" Sam asked once he had managed to get a hold of himself and moved to sit beside him.
"Because a man like you shouldn't be messing around with a man like me.... Plus I didn't know you'd be the type to go chasing boys."
"Nobody else knows that I do, so I'd appreciate it if you didn't go sharing it with others," Sam stated firmly as the man placed a soft hand on his shoulder, it was so much different than the rough actions the man had been using beforehand.
"You really are a virgin to all of this? Don't worry.... I'll take it easy on you.... for a slight price... I want your name as well. Can't keep just calling you 'boy' now can I?" His tone was kinder; surprising but not at all unpleasant, just not something that he would have thought could come from the rough outlaw.
"Oh... its Samuel. But most people tend to call me Sam," the sheriff's son told him, glad that he still the liquid courage coursing through his veins.
"Samuel, huh? I like it... rolls off the tongue nicely," Clinton chuckled before running a hand through his lengthy, brown hair. "Go on and take off your jacket and boots. I don't bite... well, usually."
Sam laughed quietly at the comment about biting before standing up and pulling off his jacket. He hung it next to the outlaw's and pulled off his boots and left them by the door. It felt odd because he had never walked around without any shoes on in any other house but his own. "Thanks by the way, I like the name Clinton."
"Ya know... it's funny. I never knew that the sheriff even had a son until here recently." Clinton patted the seat beside him again which Sam took with less hesitation than before.
"My pa doesn't talk about me much, not happy with the way I turned out I guess..."
"What did he expect? Deputy of the yeae? Grow up just like him kinda deal?"
"I guess so.."
"So what're you doing messing around with a man like me?" Clinton's eyes had suddenly became untrusting once again as he looked over the sheriff's son.
"I don't know, maybe I just have a thing for men who are bad for me," Sam answered with a soft smirk.
"Baby, you don't even know a bad man yet," the outlaw leaned forward and purred the words into Samuel's ear. A deep, sexy noise that made Sam want him right then and there.
Clinton pulled away with a smirk on his face again and Sam looked at him for a moment. Before too long he found himself leaning forward slightly, not knowing what he was doing but really hoping that Clint would lean forward as well.
The man did so, their lips meeting together in the middle and the man's hand sliding up his leg to rest on Sam's hip. He moved so that he was leaning over Samuel slightly and deepened the kiss. Clinton had ditched the tobacco some time before, but Sam could still taste it on his lips; mixed with the flavor of whiskey and beer, he found it to be an odd flavor combination. But not one that he found at all off-putting.
The man's hand sliding up his leg sent a shiver down his spine but he tried to hide the fact. The brunette's started kissing on the dark haired man's neck paying close attention to the sensitive areas of Sam's neck. "Let me know if you want me to stop.." the outlaw requested as he ran his hand up under Sam's shirt slowly, and kissed over his neck again, running his tongue over a soft, sensitive area at the base of Samuel's neck. The action brought a almost silent moan from the younger man's mouth.
"You sure you're alright with this?" Clint asked as his hand came to a rest on Sam's abs.
"Y-yeah, I will tell you if I'm not," he brought his hands up to rest around the man's neck. The little things that the outlaw was doing to him was driving him crazy, and wanted the man to continue.
The brunette turned and kissed Sam's arm lightly with a soft smile, "There we go, we curing some of your boot shaking now....You wanna be on top or as is?"
"As is, if that's alright," the sheriff's son replied as he leaned back up and kissed Clinton quickly again.
"That's what I was looking for. Good man." The outlaw gave him a light bite on his bottom lip before moving to his neck and nipping his earlobe. Another soft moan escaped Sam at the actions and he found his hands falling from the outlaw's neck to rest on his side just below his ribs.
"Whenever you're ready you can start unbuttoning my shirt," Clint purred in Sam's ear which earned a soft nod from the younger man. The brunette went back to kissing with more passion which Sam tried to meet with just as much.
It didn't take long for Sam to work up the courage to start unbuttoning the outlaw's shirt, smiling when the last button came loose and his shirt opened to reveal a muscled chest. The dark haired man laid his hands on the man's bare sides, enjoying the feeling of his skin under his hands. He didn't move them because he wasn't sure if he was supposed to and the fact brought a smirk to the brunette's face.
"Don't be afraid to let your hands wander, Samuel.... I'd actual like it if you did," he chuckled as he started working to unbutton the younger man's shirt as well.
"O-okay," Sam nodded as he slowly moved his hands up the man's sides and across his chest earning an almost silent moan from him.
"Damn your hands are warm... warm hands have always been pleasurable for me," he mused as he got Sam's shirt unbuttoned and moved to kiss across his chest.
He pressed a soft kiss onto Sam's nipple causing Samuel to moan quietly once again, his sun tanned face flushing a pale pink as Clint turned his face to look up at him. God damn, that face could turn even the most faithful of angels to sin in a heartbeat and Samuel could feel himself growing hard at his touches. Clinton could obviously tell this as he slowly kissed back up to Sam's lips, whispering on them," If I get to going faster than you want, you have the right to knee me."
Every spot that the outlaw had left on his skin was tingling with want for more and as he moved to rest his his clothed crotch against Sam's own, Sam could tell that he was wanting Sam pretty bad too. Craving just a little friction between the two of them, Sam moved his hips upward against Clint, causing the man to moan slightly louder than he had before. Sam nodded to show that he understood and Clinton just chuckled lightly.
"Quiet, get down to business type, I think I can handle that," he purred as he moved to kiss Sam's neck and unbutton his pants, slowing grinding against Sam as he did so.
"I just don't want to ruin the moment with a wrong comment," Sam explained, his words suddenly snatched from him as louder moan escaped him as the outlaw started to move against him, breathing quickly picking up despite his want to keep it steady. He snaked a hand down between the two of them and quickly undid Clint's pants, but because of the position couldn't pull them off of him. Taking the hint Clinton stood up and pulled them off and worked on undoing Sam's jeans as well.
"I doubt you could turn me off at this point," Clinton laughed as he pulled off Sam's jeans and bent down suddenly to press a kiss onto Sam's crotch through his underwear, causing the sheriff's son to twitch slightly. "Every time you moan I just get even more turned on."
"A-alright," Samuel managed finally as he turned his head slightly down to look at him again.
"So... tell me.. what had you so afraid before Samuel?" Clint asked as he pressed a soft kiss onto the dark haired man's underwear line.
"I wasn't afraid... more nervous than anything," San explained as he ran his fingers through Clint's brown locks. This was like a dream, the simple fact that the outlaw he had been admiring at a distance had was into guys AND was kissing all over his body had him in a state of shock, and Sam was so certain that he was going to wake up at any moment.
"Well.. don't be," Clinton stated as he stood up suddenly, pulling Sam up off the couch as well, and pressed the younger man against the wall. He pinned Sam's arms above his head," leave them there or else."
Samuel, not wanting to find out what the 'or else's was, left them above his head as his arms were released. The outlaw started to kiss, nip, and suck on the skin of the younger man's chest and abs, sneaking down and pulling Sam's briefs down to around his ankles.
"Well... someone is happy to see me," the outlaw teased as he kissed the head of Sam's member with a soft chuckle.
"Got anything against me sucking you, Sam?" The brunette asked as he grabbed Sam's cock with his callused hand and began to milk his cock slowly, waiting for his answer. "How's that feel, huh?"
Sam's eyes turned up toward the ceiling and a louder moan escaped him at his touch, his face flushing and breathe hitching as well. "O-oh my g-god," he moaned out in reply as his eyes half closed.
Clint looked up at the sheriff's son with a smirk on his face and then he looked back to the man's cock and ran his tongue over it once more before removing his hand mostly and taking about half of it into his mouth and slowly beginning to suck on it, allowing him to get used to the feeling. And this outlaw would have to admit he was quickly getting turned on by the moans of the slightly younger man for certain. He pulled back, popping his mouth of the other man's cock and stood up, intertwining his fingers wit the mans and holding his hands firmly back against the wall. What the sheriff's son hadn't noticed is the outlaw had snuck his own undergarments down now and he pressed his bare cock to Samuel's and whispered on his lips. "Moan my name..."
The dark haired male let out a soft gasp followed by several moans when the brunette started to suck him and did everything in his power not to buck his hips against him. It was the best thing he had ever felt before and Sam was a shivering mess by the time Clint had stood back up and pressed his bare body against his own.
He found himself staring into the man's beautiful blue-grey eyes lustfully while trying to memorize the pattern the color took. "C-Clinton~" he moaned out as he he licked his lips, embarrassed by the slight stutter; he didn't need to be told twice.
"Mmm... that's right, Samuel. Feels good don't it?l he smirked as he moved to kiss the younger man again. Sam loved the feeling of the man's lips on his own; they were soft and warm, not something he would expect from a man like the outlaw. "You want everything of me? Or are you just into being sucked off by another man?" He added the question as he started to pump Samuel again pulling away from the kiss, bringing another string of quiet moans from the man's lips. Samuel nodded at the question and kissed him back, disappointed when he pulled slightly away again. "I want everything of you," he managed before another moan escaped him at his touch. His breathing had became ragged at that point and he could barely think straight as he felt a sudden want... No need... For this man. He leaned forward and pressed another hungry kiss on Clint's lips.
"What are your thoughts on having a couple of my fingers in you?" he asked as his hand slid down and rested on the man's ass and he then kissed him back with the same want, his other hand still busy keeping a steady pumping on the sheriff's son's member.
"P-please", the sheriff's son almost begged as he bucked slightly under the man's hands, unable to stop himself. He was going crazy, the want for him driving him to the edge. Sam felt a familiar warmth in the pit of his stomach and knew that if Clint kept pumping him much longer he wouldn't be able to hold himself back.
"Get on the bed and I'll give you some." he said, stopping everything completely. He knew the younger man was building up a release quickly and he knew it would only be bigger if he didn't allow him to release just yet. "Go ahead. Get comfortable on your back or your hands and knees."
Sam whimpered at the sudden loss of contact but moved to the bed, deciding quickly that he would rather be on his back rather than his hands and knees. He got comfortable and waited for Clint to come over as well, his hands playing subtly with the blanket that covered the man's bed.
"So, how do I know the moment you leave you won't go ratting off to that father of yours of my whereabouts and my name?" he asked as he got on the bed and sat on it, spreading Samuels legs some and also bending his knees so his legs were out of the way. He licked his finger and slowly brushed it over the man's anus, watching him. "Hmm? How do I know you won't rat me out, Samuel?" he asked, his deeper voice returning.
"I wouldn't do that; me and him don't exactly see eye to eye. Why would I help the old man out?" He said as he looked away for a moment, allowing his legs to be moved and positioned. He shuddered lightly at the touch to his entrance and looked at him again. "There would be no point anyway, if I told him he would want to know how I knew."
"Oh? And if you did tell him what would you make up as a story?" he asked and then slowly eased his finger into Samuels entrance, allowing him to get used to it and knowing that working on stretching him some with fingers first was a good idea. "When I start using more fingers in you, you warn me if it starts to hurt." he said and then kissed the mans member again. "Tell me... Do you like dominate or passionate love making, Sam...?"
"I wouldn't tell him," he reinforced as a soft moan escaped him when the finger was inserted. It was an odd feeling, but not at all unpleasant. Sam took a second to collect his thoughts before nodding. "I... I don't know," he admitted in response to the question, he didn't have a preference because he had never done this sort of thing before. "Passionate?"
"Good. Then we won't have any problems." he said and kept his finger completely in Samuel for now and then kissed his lips and whispered in them. "Passionate it is, then. You tell me when you're ready for more... " he said and then moved down and kissed and began to lick the man's nipple, driving Sam completely crazy and bringing another moan to his lips. He felt bad that he was the only one getting any pleasure at the moment, and he wanted to speak up and ask what he should do for the man. He was cut off however by another moan that escaped him as Clinton started to pull his finger out and push it back in slowly, kissing along his chest the whole while.
Clint's kisses caused him to shiver again and when he started licking and kissing his nipple his breathing hitched. He brought up his arms and tangled a hand in the outlaw's brown hair. He really liked that but he tried not to get too ahead of himself.
"I'm ready.." He managed finally.
The outlaw pulled away from the kissing and nodded swiftly before he slowly pulled out his finger and licked the second one. "I'll...." he trailed as he kissed the mans nipple again. "Go slow..." he said and then slowly eased both fingers in and continued to kiss and suck the man's nipple.
Samuel's breath caught slightly at the pressure that came with the second finger. It wasn't painful, but was slightly uncomfortable at first. He let out a soft moan as his thoughts were dragged back to the man again. He moved the hand that wasn't tangled in his hair across his upper back and shoulders, feeling the muscles that were there.
"Mmm, you're doing good Samuel." he praised and slowly moved the two fingers in and out in a slow thrusting motion once he had become more accepting if them. He brought his lips up to meet the mans once more, knowing soon enough he'd go back on giving attention to the man's member, but wanted to let him get used to the fingers first. 
Samuel smiled at the praise and kissed him back, enjoying what Clint was doing to him and every once in a while a soft moan would escape him to show it. "Clint~" he moaned under the kiss and found himself bucking gently against him once again.
"Mmm, you like that? How's this feel?" he asked and then picked up the speed on the thrusting of the two fingers in the man before he pulled both fingers out and licked a third, his pinky. "You want to try for a third?" he asked and worked on getting his fingers nice and wet, and after that he kissed Sam again. "You want to feel three, you handsome thing?"
Sam's moans had grown in strength as Clint picked up the speed of his fingering. "G-good," he sputtered out, feeling like a shaking mess at the mercy of the outlaw above him. He wanted to make him feel as good as he felt, but wasn't sure how. 
He watched as the outlaw licked the third finger and felt a little wave of nervousness run through him as he nodded. "Yes, I want to feel three", he replied in a seductive tone.
 "I'll go slow. And like I said, you can always knee me." he said and kissed the man once more before very carefully and slowly starting to ease three fingers into Samuel's entrance. "How's it feel? Need me to stop for a moment?" he asked, lightly biting the side of the younger mans neck and kissing it in a lusty manner.
Sam kissed him back but pulled away when he started to insert the three fingers into him. He gritted his teeth against the slight pain, but shook his head at the question," I'm okay." He focused instead on the light biting and kissing, soon growing used the presence of the fingers. He kissed the man's jawline as well, feeling the slight stubble from shaved facial hair.
"Sorry. It gets better. The first time is always the worst." he whispered and softly kissed down to Samuel's collarbone before kissing his lips to help him forget about the slight pain he was feeling. "Its just always better to get stretched put first slowly than just trying to shove a man's cock right into you..." he explained and finally got the three fingers completely in. "There." he smirked and bit the man's bottom lip playfully, whispering on his lips in a lustful tone. "I can't wait to be in you..."
Sam listened as he spoke and nodded before groaning lightly in pain and pleasure at the same time as his fingers finally went completely in. The dark haired male looked at him for a moment," Thank you for being gentle with me." 
He sucked in a soft breath and smiled at the bite on his lip. "I can't for you to be in me either", he replied in an equally lustful tone before leaning up and closing the gap between their lips.
"Mmm, don't mention it. I might be a heartless bastard but I wouldn't want any man to have his first time the way I did." he said and kissed him back before slowly beginning to spread his fingers inside Samuel, working on slowly stretching him just a bit. "Tell me to stop if it stings too much." he said and then leaned over Sam a bit more and deepened the kiss, fingers still slowing trying to stretch Samuels entrance out.
Sam found himself wondering about about the man over him. Clint was a puzzle and one that he would love to solve, but the thought was quickly banished when he started to spread his fingers inside him. His face was flushed again at this point, tanned skin turning slightly pinker. Even though there was some pain with what Clint was doing, it wasn't awful and he found himself growing used to the light stinging. When the kiss deepened, Sam parted his lips slightly to allow him entrance if he wanted it.
"I have to admit I really like that blush you get, Samuel. Its very much a turn on for me, I have to admit." he said in a soft tone upon the man's lips, soon spreading him enough and easing his fourth finger into Sam without much warning so he wouldn't tense up too much. "I'm sorry if it hurts... it'll stop soon. Just take a breath." he said in a whisper and kissed him more in an attempt to distract Sam.
The sheriff's son started to say something but instead groaned in light pain when if the fourth finger was inserted. He set his jaw at first against it but eventually took a breath and kissed him back to take his mind off the dull pain. The pain subsided in time like the rest but he began to worry if the brunette's fingers hurt him, what would it be like for the man's cock? He reluctantly pulled away from the kiss and looked at him again ,"I like the way you're looking at me."
The outlaw slowly pulled his fingers out and then kissed the sheriff's son once more and whispered on his lips. "Eventually some day I'd like to try some oral on that ass of yours." he said, not ashamed to speak dirty like that. He then whispered in the man's ear, "Kinda hard not to look at you with lust when you're squirming under me, Samuel, its just very hot to me." he said and then moved completely over top of Samuel and began to kiss him again.
Sam took a soft breath as he pulled out his fingers, and flushed at the simple dirty talk that both made him embarrassed and aroused at the same time. He listened to he speak again and decided even if he had made it seem impartial to him that Sam still liked the look. He kissed back with renewed enthusiasm and lifted himself up slightly to rub against Clint in an attempt to arouse the man further.
"Mmm, th-that feels good, Samuel." Clint moaned out and kissed the man again, pressing his body to the younger man. "What do you think of me having my tongue in you? Would that make you uncomfortable?" he asked and then rubbed a bit more against Samuel back, his cock almost fully erected now as well. "Don't stop... that feels go-good Sam."
Clint's moan made Sam smile as he pressed against him again glad that he was doing something right. "I don't know how I feel about it... it would be a different experience", he replied before moaned when Clint started rubbing against him as well.
He brought himself up again and rubbed against him with more enthusiasm than before now that he knew he was pleasuring the outlaw as well.
"I'll let your mind ponder on the thought for a while..." he said before he pulled back from him and moved down Samuels body and took his cock in his mouth again and started to take more of him than last time, bobbing his head some on the man's cock, pumping his lower base at the same time.  He popped off the man just for a moment to grin at him.
"You taste amazing, just can't help myself..." before he started sucking him off again faster.
Sam let out a loud moan/yelp hybrid sound and arched his back when Clint suddenly started to suck him again. He started bucking against his mouth without really meaning to and let out a string of lustful moans, warmth spreading over his lower body once again. He managed to catch his breath when the man stopped and started to say something but was cut off when he started to suck him off faster than before. "Cl-clint! You're going to make me c-um~" he moaned as he tried to fight the feeling as the outlaw bobbed his mouth onto his member.
The outlaw abruptly stopped and popped his mouth of the other man's member and tilted his head some, licking his lips a bit.
"I'm sorry? What'd you say?" he teased and kissed the head of Samuel's member again, his eyes watching the man. He didn't  anything else but kiss it for the moment, loving how the younger man just was so pleasured beneath him. "You say something about cumming, boy?"
The dark haired man gave a soft whimper when Clint stopped abruptly and looked back down at him. He was shivering again in slight frustration and anticipation; the kissing only making it that much worse. He was hard as a rock, every part of him wanted the man leaning over him.
"I said you were going to make me c-cum," he breathed out in lust.
"Oh yeah, that.... Just wanted to make sure that I heard correctly, thanks." he said with an amused grin before he pushed two fingers back into Sam's entrance and thrusted heavily in and out of him, but also adding on by sucking on his cock, bobbing his head quickly on it.
Sam arched his back again in pleasure when he started fingering and sucking him again. Try as he might, the motions were so great that he didn't feel like he could hold on for much longer. He tangled his fingers into the folds of the blanket as his moans grew stronger, before he finally moaned louder than the rest of them and climaxed, feeling horrible for doing so in Clint's mouth. He covered his red face with his hands in embarrassment," I'm so-sorry."
Clinton surprised Sam by swallowing as much of the cum as he could when Samuel released. He then pulled off him and pulled his fingers slowly out of Samuel and licked from the base of his cock, up, as there was still some cum leaking out of his cock. Clint had Sam's cum dripping off his chin and he grinned at the guy's apology. "Don't. You taste so good, Sam." he said and licked him again, his eyes watching Samuel, his own breathing heavy and his own cock aching now after seeing the handsome sheriff's son cum. "Tell me how it felt." he grinned devilishly as he licked the man's member once more.
Sam finally managed to uncover his face and and look at him. He smiled lightly and reached down, wiping the bit of his cum off Clint's chin with his thumb it was everything he had not to moan at the licking. The outlaw once again surprised Sam by grabbing Sam's finger in his mouth and sucked it softly in a similar manner to what he had done with his cock.
"That was amazing and now I want you more than anything", be replied honestly ad he looked down at him. God, that look was the best thing Sam had ever seen, enough to drive anyone crazy.
"You need a bit more stretching out or do you think on can take me, handsome thing?" he asked and leaned up over Samuel and smiled down at him. "Huh hotness?"
He looked up at him as he leaned up over him, the smile melting him. "I think I'm ready for you", he replied quietly even though he was quite unsure.
Clinton nodded at the man's words and knew by the way he was acting that he wasn't positive how he felt about taking his cock inside him yet.
"Why don't we take it really easy and if it hurts too much I'll stop?" he offered and kissed the man on the forehead and smiled at him. "Don't worry, I can be very kind... very gentle."
Sam nodded his head and couldn't help but smile at the kindness from the outlaw, he had to admit that he liked this side of him better than his other one.
"Alright, I'll appreciate that", he accepted as he ran his hands down Clint's muscled sides. The kindness seemed so odd coming from him, like a totally different person from the one in the barn a few hours ago. Perhaps it was a wall coming down....or too much to drink and way too horny to keep up the harsh tone.
"What I want you to do is to relax and take a nice breath in and out slowly. Got it?" he said as he positioned himself over the younger male and allowed his cock to rest against the other man's entrance that was quite wet from his saliva.
"And if it really hurts, you stop me." he said and waited for Sam to take the breath in and he pushed only the head of his cock into Sam, knowing that would be just only the first bit of pain.
"O-okay", Sam did as he was told and relaxed as much as he could before taking slow breaths in and out. He nodded and set his jaw against the pain from entrance of Clint's member, even if it was just the head, and took a sharp breath through his nose. He gave it a few moments before nodding slowly to show that the outlaw could continue.
"Good Job, Samuel. I know it hurts, but it'll soon feel so good, I promise you." he said in a soft tone and softly kissed the man's lips again and eased just a bit further in. "Just tell me if you need me to stop..." he reminded and kept easing in slowly. Samuel groaned quietly against the pain but looked back up at his face and knew that this was what Sam wanted more than anything.
"Keep going", he said with a weak smile as he reached up and pulled the male's head down so he could kiss him again, glad for the distraction.
Clinton kissed his lips back the same,knowing that was a good way to help him through the pain he was in.
"Shhh, its okay. I can stop..." he said and stopped himself about halfway inside Sam and kissed him again. "Take a couple breaths. I know it hurts, Samuel, I'm sorry..."
Samuel looked at him thankfully when he stopped and kissed him back. "Such a sweetheart", he managed to tease as the pain became more of a dull throb. He took deep breaths again and couldn't help but think that there was pleasure with the pain he was feeling. He leaned forward and kissed him again with slightly more passion. "I'm okay, now."
"Not in your wildest dreams..." he laughed, "I just know how bad the pain is and don't want it that horrible for you or you'll never want sex again, believe me..." he said and then slowly pushed the rest of the way in and kissed Sam back as he did, before whispering on his lips.
Sam looked up at him with a smile, enjoying that laugh. He began to think more on the outlaw which helped distract him as Clint slid the rest of the way in.
"I'm in. You did it," Clinton stated in a more cheerful tone.
Sam gasped quietly and a broad smile formed on his face again. "That wasn't so bad," he managed as he licked his lips quickly to wet them.
"You did good." he said in a praising type of voice and grinned at him before softly biting the man's bottom lip teasingly and then kissing him. "I'll give you a few minutes to get used to the feeling before moving." he said and then whispered on his lips. "Your first time is probably ten times better than mine was..."
Samuel felt good under the praise and kissed him back. He nodded when he said he'd give him a few minutes to get accustomed, but he also needed those few minutes to get his heart rate under control. "I'm sorry to hear yours wasn't that great..."
The outlaw laughed. "Yeah, well, I didn't expect it to happen the way it did either. Hopefully yours is better and you don't regret it later on." he said and began to kiss Samuel more, bringing his hand down between them and gently just stroking the shaft of Samuel's cock.
Sam kissed him back and felt himself grew even more erect again under the brunette's gentle stroking. So far he wasn't regretting following the outlaw out of the saloon, in fact this had been one of his better experiences so far. The sheriff's son was more than happy to be laying with the puzzle of a man; wanting nothing more that to solve the mysteries that surrounded him.
"I know every minute you're with me you're trying to figure out a piece of me, so why not just have the balls to ask the questions you so badly want answered?" The brunette abruptly asked and then kissed along the younger man's neck and began to slowly thrust in and out of him, just only moving about two inches or less in and out.
"There's so many I'm not even sure where I would want to start", he explained before started to thrust inside him slowly by the smallest amount. It didn't take long for him to grow accustomed to the movement and he let out a soft moan.
"Well, ask the first thing that comes to your mind." he said and then grunted a little ask he pushed back in and then eased somewhat out of Sam. "Damn, you're tight...."
"Ah~" he moaned quietly as he pushed back in. He wrapped his arms back around his neck loosely and kissed just under his jaw. He thought about it for a moment wondering if now was a good time for a game of questions and answers but he realized he might not ever get the opportunity again. 
"Why did you decide to do what you do?" He asked as he moved his hips a little to help stimulate the both of them.
"What? To become a wanted man? An outlaw? Outcast?" he asked and kissed along Samuel's neck and then began doing longer thrusts now, going a bit further in and out now than before, obviously liking the moans from the other man.
"Somewhere in your life you decided you didn't want to follow the...rules. I'm just curious as to what made you", he explained, having to pause to moan. There was still a little pain, but it was more of a discomfort and the pleasure made up for it.
"I stopped following the rules the day five men came in and held my father at gunpoint and raped my mother when I was only a boy and then killed them both in front of me. After that I became who I was to stop other men that thought they could just do whatever they wanted. I kill to save innocent lives."
Sam was silent and turned his eyes down to avoid his. "Oh... I'm sorry... Everyone makes you out to be this bad guy that I guess I just assumed with them..." He admitted still not willing to look him in the face.
"I am sometimes... I used to be worse than I am now... believe me, I was a bad guy and you still never want to cross me." he said and then grabbed the boy's chin and made him look at him. "Now, no more moping... be happy." Samuel gave a soft, forced smile and looked him in the face before leaning up and kissing him, wanting to distract Clint as well as himself. He figured he would just ask more questions later if he was still allowed.
"You know how long its been since I made love to a man and actually was able to watch his face?" he asked and then began to kiss Samuel again, getting a good rhythm of thrusting going now, slowly feeling his own climax beginning to build up.
"Too long?" He answered with a question. He was slowly getting the hang of it as he started moving to meet Clint's thrusts. Sam didn't break the kiss except for the occasional pause for them to breath, though his own breathing was growing to be ragged again.
"You want me to pull out before I cum?" he asked in advance and also chuckled at the question. "Yeah, way too long." he said and then began to slightly roll his hips against Samuel, causing a great deal more pleasure for the younger man.
"That's up to you, Clint. I don't care either way", he managed as he looked back up at him. Samuel groaned loudly in pleasure when Clint started doing something new and found his hands tangling in his brunette hair.
"Well, you will. Do you want your ass filled with my cum or no?" he asked again and then kept up the rolling of his hips as he suddenly took Samuel's lips hostage and kissed him passionately and deeply, tongue and all.
Sam thought on the question for a second before nodding. "Y-yes, you c-can"he answered quietly just before Clint took over kissing him. He sucked on the outlaw's tongue and occasionally attempted to tease him with his own.
"Alright th-then" he quivered out As he kept up the thrusting/humping, getting so close at a release of his own and it was making him ache so bad.
"Da-Damn I'm close, Sam.." he moaned out and then bit Sam's tongue back and sucked on it some, teasing around with him.
Sam loved the sound of the outlaw's moans so he continued moving so that he was meeting his thrusts as well. He was moaning as well at the teasing. He gently bit the man's lower lip like Clint had done so many times before to him before going back into the kiss.
"Mmm you're a good kisser, Samuel." he complimented and it didn't take long before Clint was right on the edge of releasing.
"So are you, Clinton."
The outlaw pulled back and groaned as he suddenly released, the groan turning into a pleasured moan as his face sunk into the younger man's shoulder, his body quivering over top of him as he released inside Sam. "S-Shit... o-oh yes..."
Sam found himself moaning as well at the feeling of being filled. He ended up shivering as well looking at the ceiling of the cabin as he took steady breaths to calm himself. "O-oh my g-god", he stuttered out in pleasure as he wrapped his arms around the male's back, fingers digging slightly into his skin.
"I think we might j-just have to stay like this for a while because I-I don't want to pull out." he said with a slight weakened quiver. He bit his lip some and breathed heavily out of his nose and then whispered in Sam's ear, "Y-You just feel so good..."
"I'm okay w-with that," Samuel smiled faintly as he turn his head slightly to kiss the side of the man's head. He could feel the soft quivering that came from Clint's body against his own, but found himself tired. He was well satisfied and hoped that Clint was too, because he wasn't sure if he'd be able to go through a second round.
Clint kissed him back and then chuckled a little. "Go-Good, 'cause you didn't really have a choice." he said in a joking manner and then after about ten minutes he started to very slowly pull out of Samuel.
He then kissed the man's chest before stealing another from his lips and then laying down beside him and running a hand through his own hair. "I th-think we're even now..."
"Good, b-because I don't like having debts." He smiled jokingly, turning his head to look at him. He had managed to control his ragged breathing, even though it was still heavy. He took a deep breath and turned so that he was facing him, before moving to lay his head on his chest without thought and not knowing how Clint would react.
"Well, c-consider it paid in full now..." he said, his breathing just slightly still off from their intimate session. He then looked at the man as he turned to face him and Clint smiled a bit, but then lost the smile as the younger man rested his head on his chest. Clint smiled again softly and his hand came up and ran his fingers slowly through the other man's hair. "How do you feel, Samuel? Good? Bad? Sore..?" he asked and kissed the top of the man's head.
Sam's eyes half closed when the outlaw ran his fingers through his hair, finding the movement comforting. A contented sigh escaped him before wrapping an arm around his bust. "Kind of sore, but in a good way", he said truthfully as he turned his head slightly so be could look him in the face.
"Mmm, you'll probably be real sore in the morning..." he said and then softly kissed the man's lips once he had looked at him. "But it'll get better, each time. Worst is over." he said and brushed his hand along the man's slightly scruffy cheek and then smiled a little.
"Mhm..." He hummed having figured as much about being sore. Riding home would be quite the experience. He kissed Clint back and returned the smile when he ran a hand over his cheek. 
"You know, you're the first man to stay after the sex..." he admitted and then closed his eyes and sighed. "You do realize your father can never know you were anywhere near here, right...?"
"I feel like it would be rude to just leave, especially after such a great time", he sighed watching the male's eyes close before turning his head back down to a comfortable position again. "He doesn't need to know. I'll make something up to explain why I was missing."
"You mind if I pass out on you?" he asked and looked at the younger man and gave him a half smile. "I'm exhausted... and achy." he said and then yawned some and his hand rested on the man's arm and he softly caressed it as he closed his eyes again and exhaled slowly in content. "You still going to be nervous the next time your with some other man? Hopefully I cured your boot shakin'..."
"Only if I can stay here with you", he replied with a soft yawn as well. Sam moved his head lowly to get comfortable on his chest. "And I don't know. Guess time will tell," he mused as he paid attention to the callused hand that caressed his arm. The movement was comforting and was lulling him into a sleep he was fighting.
"Mmm, sure, I don't mind..." he yawned and then kissed the man's head again before he finally drifted off into sleep, his hand simply rested on the other man's arm as he slept soundly, exhausted from their activities.
Sam yawned again before closing his own eyes and and slowly drifting to sleep on the outlaw's chest without another thought. 
What the two boys didn't know is someone had been listening in on their conversation when they were back at the tavern and that one person now knew the name of the man that was so badly wanted for several cold-blooded murders that he had committed.