Sailing His Ship Pt. 06

The first part of the week was a hustle and bustle of things: projects needing launched, meetings, emails, and paperwork. They were the types of days lacking enough hours in them, and the evenings were spent relaxing, building up to the next.

Wednesday had come, and Charley had decided to spend the night at home. She dropped him off at the end of their day, saying their pouty goodbyes for a night or two, and trying not to linger too long as to not change their minds.

At first the silence and solitude was causing Charley to second guess his decision, but plants, laundry, and cleaning helped pass some time. A little more time was spent reaching out to his friends. McKenzie and Will had hit it off, and had a second date planned. Sabine called that one. Sam was still doing the family man thing, and asked how the job and lovelife was treating him.

As 9pm rolled around, Charley decided he needed to get out of his apartment. Making his way out the door he sauntered down the sidewalk, the light of the sun dimly painting the sky and slowly fading.

"Benny's" was a quiet little pub about a 5 minute walk away. He stepped in and a few patrons littered the joint. Nothing exciting, no crazy parties for midweek, no crowds or college kids getting silly. Mainly a few midlifers lounging with their cheap watery beers.

Charley took a seat at the bar, "Give me a Daydream Ale," he said to the bartender as he approached and gestured at him.

"Good choice."

The tender poured the glass, a tiny bit of head on top, and set it on a coaster in front of him. A screen played the typical bar tv images: reels of fails, feats, and extreme sports. He slowly sipped his beer and pulled out his phone.

"Decided to grab a drink at the pub down the street. Miss you. Life is a lot more boring without you around." He texted Sabine.

He was startled away from his phone time, when a large hand landed upon his shoulder. He looked back.

"I didn't expect to run into you here...." Matthew's spoke.

Taken aback, Charley stuttered, "Uh, h-hey Matthew. No, I didn't expect it either."

"Are you a regular?"

"I use to be more so, but not so much lately. You?"

"Yeah, it's a convenient spot for me. I'm surprised we haven't run into each other here before."

"Yeah, it's actually pretty convenient for me as well. I just haven't been staying much at my apartment."

"I wouldn't be if I were in your shoes either," he chuckled.

The bartender approached.

"I'll have whatever he's having," Matthew said, and the man behind the bar poured another glass.

"So I guess I should ask why you're here now. No problems I hope."

"Oh no, not that. Just needed to catch up on some things. I've been so sparse at home, it needed tending to."

"Completely understand. With my schedule, sometimes it all gets away from me." Matthew plopped down on the stool as he spoke.

"So were you successful?"

"Successful?"

"At catching up on your things?"

"Oh, yeah, I was. It wasn't too much. Just needed a few hours, and the beginning of this week has been non-stop. Deadlines, meetings...ongoing things that demand focus at work. So not overly exciting. How has your week been?"

"Oh, aside from my whole brain exploding, ya know....pretty average. I had Sunday off after I left, which I definitely needed. I ended up taking a nice hike, and then it was back to work for me."

"Trust me, I understand the whole brain exploding thing....and all that. She's pulled a hell of a lot of doozies out on me."

"I'd believe that...given the whole..."

"Yeah.... So do you like waiting tables?" Charley felt uncomfortable discussing those things near the bartender.

"Oh, well, it's good money. I enjoy people, I don't think I'm bad at it, and we get a lot of good tippers. Especially Sabi...Ms Coultier."

"Almost lost it there..." Charley joked.

"I'll have to check myself. But no...it works for me right now. "

"That's cool."

"So what do you do, if you don't mind me asking."

"Well, I was a designer but now I apparently got promoted to design lead. So that's a new thing. Basically I create visuals for ideas passed down from marketing. Except, now...I oversee that whole team. It's an adjustment."

"Sounds intense."

"You have no idea, Sabine is...also my boss."

"Oh....Wow! Holy shit."

"Yeah. Don't get me wrong. I love it, and it's fun...but the actual position is a little more than I expected. I'm growing into it."

Matthew flagged the bartender down. "Get him a shot of his choice and a beer, and I'll have a tequila and another one of these "

The bartender then looked at Charley,

"Give me the same."

The shots arrived first.

"To your new position." Matthew raised his glass.

"To the new position." Their glasses clanked.

Their beers were set in front of them.

"And...to a new..friendship," Matthew raised his glass again.

Charley bumped the beer glass and they both took a swig.

Matthew leaned over and said, "You want to move to that table?" Pointing to the table off to the side.

"Sure."

They grabbed their glasses and walked to the table. As they were sitting down, Charley's phone buzzed. He reached for it.

"Hey lover, hope your night was good and you got everything done you'd hope to," the text read.

"I did. Walked down the street to the pub nearby a few minutes ago. Turns out I ran into Matthew"

"Oh, well, if you do anything fun, send me pictures. Don't do anything I wouldn't do."

"We really did surprise meet, and are just having a beer," Charley felt like he should be ashamed at the moment, like he screwed up...and yet why?

"Baby I'm just fucking with you. I'm fine with anything that happens between you two as long as you want to be with me. I know Matthew's not that daring."

"Apparently no one is as daring as you, Captain."

"That's right bitch, say it again. Lol."

Charley looked up from his phone, "Sorry, it was Sabine just checking in."

"Oh yeah. She say anything exciting?"

"Not really."

"Can I ask you a question? Seriously and honestly?" Matthew's face got serious.

Charley looked across his face and sympathizing with it's expression, "Yeah, sure."

"So the other night, I really got into that. Maybe it scared me how much I got into it...and then I was wondering whether I was gay, but I like women, but then..."

Charley interrupted him, "Hey man, it confuzzles me to, butI don't think it needs a label, " Charley could hear Sabine's voice in his head," ....it was fun. We all enjoyed it. No one needs to know anything other than us. I don't think that makes you gay... but if you are there's no problem with that either..." Charley now verbally tripping over himself.

Then Matthew's phone buzzed in his pocket. He drew it out and looked at it.

"It's ok if you want it, just make sure to tell me all about it." A text from Sabine read.

Matthew's dick was already slightly chubbing from his conversation, but now his dick was pressing against his shorts. Somehow having been given permission turned him on even more.

"Sorry. Yeah, I uh, I really enjoyed the other night. I can't quite stop myself from thinking about it..."

Charley wanted to play dumb, pretend nothing happened, pretend he didn't get off on it all, but he did, and Matthew was in a place he understood, to a degree.

"Honestly, I can't get it out of my mind either."

They both paused to take a big gulp of their beers.

"Hey, do you want to finish these, get out of here and smoke a little?" Matthew asked.

A little weed sounded good to Charley, "Yeah, that sounds good. I have a few beers at my place and we can do that on the way there, or once we get there."

"Awesome."

They both sucked down the rest of their beers and paid their tabs.

All the light had faded outside and street lamps dimly lit the area. No one was really out that night. As they got a minute down the sidewalk, Matthew pulled out a one hitter and took a puff, holding it in for a moment as they walked. Then he packed another hit and passed it to Charley, who did the same. After a few minutes and a few tokes, they both felt it start rolling slowly over them.

Shortly after they arrived at Charley's place.

"It's definitely nothing like Sabine's place, but at least I tidied it up a bit."

"You're fine man. You should see my place right now. It's a wreck." Matthew chuckled.

Charley reached in the fridge and grabbed two beers and handed one to Matthew.

"So you really have never done anything like that before?" Matthew inquired again. "You just seem so much more confident in your response to it."

Charley let out a guttural laugh. "No, I haven't. I mean, I have been subject to Sabine's desires, so that's 'stretched' my more mundane experiences," he chuckled,"and I suppose she had been desensitizing me to the idea some. But no, honestly, it was all new to me, and rattled me as well. And as far as my confident response, those were more her words than mine."

"That makes me feel better." Matthew said, his large hand then rested on top of Charley's, causing Charley to startle internally, and look up.

Matthew was a bit taller than him, around 6'1" and a broader more muscular frame. A curly blonde mop on top of his head and bluish gray eyes.

Now those blueish gray eyes were looking directly into Charley's. Despite the anxiety that Charley was now seemingly experiencing more than Mathew, his dick began to stir. A silence that seemed to linger, probably lasting much shorter than it felt like, was broken when Matthew said, "But you liked it, right?"

His eye contact never broke, his long fingers curling around Charley's smaller hand...a slight gasp of breath left Charley's lips, as he let out a mousey, "I did."

Again they both gulped their beers...a giant gulp...

Then Matthew grabbed Charley wrapping his arm around him and pulled him in to him and kissed him, his hand wandering down to Charley's ass, cupping a cheek entirely with his hand, and pulled him tighter into his body. Charley could feel the stiff bulge in Matthew's pants against his stomach.

A feeling of surrender came over Charley, as Matthew took over him and probed his mouth with his tongue while kneading his ass.

Their lips parted for a moment, Matthew looking down at Charley pressed into his chest, the smaller man looking so cute to him. A helplessness, a sense of abandon were visible in his eyes.

In a soft voice, Matthew said, "I have been craving this since the other morning. Something about you just grips me," he leaned in for another kiss, and took hold of Charley by both ass cheeks lifting him and holding him suspended, Charley wrapping his legs around him as Matthew pressed him against the fridge and continued making out with him. How long they kissed was of no importance, as time is relative in these types of moments.

Eventually Matthew set him on his feet again, took a gulp of his beer, and said, "Was that okay?"

Charley pupils were dilated, him still catching his breath, took a gulp as well, "yeah."

"So if I wanted more, you wouldn't be opposed?" Matthew asked as he ran his fingers down Charley's chest.

"No, I wouldn't," barely came out of his lips before Matthew grabbed him by the ass and pulled Charley back into him, and began kissing him again.

Then Matthew kissed down his neck, and along his shoulders, "Fuck you turn me on so much."

Reaching down, Matthew flipped Charley's shirt over his head, and Charley followed doing the same.

Matthew was a much more muscular guy. He had a nice developed chest and a hard stomach.

Matthew grabbed Charley's belt, and undid it, then the top button of his shorts. The weight of the things inside caused them to drop to the floor. As Matthew lowered the zipper the first inch, it revealed a wet and tented pair of very light pink cotton panties, with a wavy white trim over the legs.

"This is so fucking hot," Matthew said as he laid eyes upon Charley's undergarment. His finger dipping below the trim of the leg, and running down the crotch along Charley's balls.

Charley blushed a bit, looking down as Matthew cupped his whole package in his hand. In a quiet voice, Charley spoke, "Do you want to come to the bedroom with me?"

"I'm dying to," Matthew said, his cock straining against his shorts.

Charley opened the bedroom door and flipped on a lamp. It was fairly dim which was better for the mood anyways.

Matthew approached him and pushed him onto the bed, then began removing his own pants. His bright green boxer briefs had a blue threading and a black waist band.

His cock was thick and was stretching the mesh fabric.

He plopped down next to Charley, and began tracing his fingers over his chest and around his nipples. Charley's nipples hardening in reaction to the teasing sensations. Matthew was propped up on his elbow leaning over Charley, who laid on his back.

"When did you start wearing panties?" Matthew asked, running his fingers down the center of Charley's stomach.

"That started when I met Sabine."

"I wouldn't have thought it to be a turn on for me, but I find it a huge turn on with you."

"Really?"

"Yeah, something about the way it frames you...I couldn't get it out of my mind the first time she sent a picture of your cock all trapped in the fabric."

"That's good, I felt really awkward about it at first, but loved the feeling of the fabric and fit. Plus it made me feel a little vulnerable."

"Do you like feeling vulnerable?" Matthew asked now running his fingers very lightly over Charley's dick through the cotton.

Charley let out a gasp, then answered, "Yes."

"I feel like these make you so much more vunerable. And so sexy. The thought of a guy really rarely crossed my mind. But these make you feel like something else entirely to me, and it makes my fucking dick hard as hell."

Matthew's hand was now cupping and rubbing his whole package in circles, grazing his perinium and pressing into it at times.

"I'm not exactly sure what I feel I am right now. Part of me embraces the feminine aspect, and yet I am so not a girl, or even girly. I guess sometimes I like feeling a little girly though..."

Matthew slipped off his boxer briefs as soon as Charley answered. then kissed Charley hard, grabbed his wrists and rolled on top of him. His hips started grinding his dick into Charley's, both like rocks against each other. Matthew reached down and slid his cock through the side of the pouch, so it was pressed inside thrusting along Charley's cock, and the strap running right between his balls, and rubbing against his ass. Over come with the sensation he began working his hips in rhythm, then wrapping his legs around Matthew. Their cocks both wet with precum coating the panties with dark wet spots.

Matthew pulled back and sat up a minute and in a slightly growling voice, "Damn man, you are such a fucking hot little slut. Rubbing my cock on yours is so sexy." He reached down grabbing and holding both of them in his hands and stroking slowly and squeezing.

Matthew grabbed his phone and snapped a shot or two.

"For Sabine?" Charley asked.

"Yeah."

"You might as well take a video."

Matthew set his phone on the dresser facing them and hit record. Then hopped back on the bed in between Charley's legs with Charley still on his back.

He reached in to the panties from the side, pulling out Charley's throbbing cock and held it against his. Stroking them together. Charley reached over to the night stand, grabbing a bottle, and handing it to Matthew. "This may help. "

Matthew poured some lube on the tips of each dick, working it around them, and then began stroking them both together again.

"God I love having both our dicks in my hand."

Matthew then rolled off to the side on his back, and pulled at Charley to get on top of him. Charley climbed on to Matthews hips, so that their cocks were aligned. Matthew wrapped his hand around them. Charley's dick seemed to disappear in his large hand. The difference in size was so noticeable from this angle. Charley began shifting his hips back and forth, fucking Matthews hand as he slowly pumped them both.

"Mmm, that's it you hot little slut," Matthew said, running his hand over Charley's nipples and pinching them. Then grabbing his ass, began pushing him and pulling him to control his thrusts."

"You like my big fucking cock rubbing against you."

"Mmhmm."

Matthew squeezed his ass hard and pulled Charley a little further up on his cock. Now Charley's balls hung on either side of Matthew's cock. As he ground his hips into him, he felt Matthew gliding from the base of his dick, down his balls and over his ass.

"Damn, you fucking hot little piece of ass, that feels so fucking good. You like riding my dick?"

"Mmhmm. Fuck, that's nice."

Matthew, having seen his reaction before, slapped Charley's dick, making it flex, and leak a little more. Charley gasped.

"Do you like that?"

"Yes, " Charley moaned.

Matthew slapped a few times, then squeezed from the base and stroked upwards, squeezing the head of his cock until a big drop of precum formed at the tip. He wiped it up his hand that he hadn't been stroking with, put it to his lips and licked them.

" I so want to violate your ass." Matthew said, his confidence rising and his lower head driving.."would you like me using your boy hole?" His cock head was now circling his puckered taint.

"Fuck that feels so good..." Charley just kind of sank into it. He worked his hips so he could feel the big cock glide over his asshole. He was absolutely lost in the sensation.

Matthew give a light slap to Charley's balls, making his gasp, and took hold of his hips, pulling him harder against his cock.

Then Charley grabbed the lube, and a bottle of poppers Sabine had given him with a dildo in case he wanted to "reminisce."

He poured more lube onto Matthew's cock, and took a large whiff from the bottle, and offered it to Matthew. Matthew, despite having never tried it before, followed Charley's lead.

Matthew within seconds felt his heart rate pick up, and his mind go blank, every touch, and sensation accentuated. He could feel Charley lift up, grab his cock, and guide it into Charley's hungry hole.

Charley, let out a loud girlish moan as the large head popped into his tight opening. Taking a few deep breath and adjusting to it's size, his mind craving that feeling of fullness. As he relaxed he began sitting back on it. Inch by inch Matthew filled him, until he stretched little hole rested against Matthew's ball sack.

"Fuck that is the tightest little hole," Matthew growled. "You've got such a nice little pussy."

Charley moaned as he rested his hands on Matthew's chest and started sawing his hips back and forth on the cock, head back, moaning like a little bitch.

"Oh fuck yea, you like daddy's big cock working your little pussy? You like that bitch?" Matthew slapped Charley lightly across the face. Then gripped his throat, squeezing slightly, Charley now picking up his pace, and bouncing on his dick. "That's it baby, you ride that cock you little fucking sissy. You like being my little faggot don't you...."

"Uuuhhh-huuuh," Charley moaned in reply.

"Fuck yeah, you ride Daddy's big dick so good."

"Do you like it daddy, do you like my little pussy?"

"Oh god, yes! You are so fucking hot." Matthew was now thrusting into Charley each time he came down on his cock.

Charley,a cock was slapping against Matthew's stomach, flinging precum all across it. Matthew took another hit of poppers, sinking again into the euphoric feeling before putting it to Charley's nose again.

Charley slowed again for a moment, grinding himself, as deep as he could take Matthew, and Matthew slapped his cock again, then took his balls by the base and pulled holding them out from his body.

"Oh god," Charley moaned. He could feel Matthews member swell inside him even more. He reached back and pushed his fingers against Matthew's ass and started working one in