Sailing His Ship Pt. 04

She pulled up to his place, then, touched his thigh and gave it a squeeze. She lowered her sunglasses and stared him in the eye, and said in a 50's jersey noir film type of way. "You've done good kid. "

"Is this where I get on a train or something?

"Unfortunately...I think it is. But this isn't goodbye..."

"Better not be," he chuckled,

She leaned in and kissed him lovingly, and then their eyes met and Charley turned grabbed his bag, and walked away.

A few hours of catching up on his own life came and A went, hours of busy work riddled with images of the last few nights. Images that came with too many questions.

He sent a text out to a few friends, "Anyone want to grab a drink?"

Will: "Yeah buddy, I could definitely get out of the house."

Sam: "I'm game."

"Cool. Aim for 8:30-9?" Charley asked

Will: 9 would be good."

Sam; Works for me.

"Good deal. Meet at the Soggy Muskrat?

Sam:"Might as well."

Will: "Works for me."

He had put off doing his laundry and gathered it, and then opened his bag to add what he needed in there.

A note sat on top, "I left something I thought you should wear to your 'friends night.,' and something else."

Below the note was a red package wrapped in a black bow.

A white pair of panties with a black bow just above the crotch laying in box, and a package below it. It was neatly wound in bubble wrap. A note was wrapped in with it.

"If you choose to use this, I promise it'll be for the better, " the note read. Inside was a small butt plug.

Charley wasn't sure about it. Wearing panties when Sabine was around was one thing, but to wear them when he was going out with friends was another. And the buttplug? Did he really want to be all worked up for his friends?" How would it be for the better," he wondered.

Charley unpacked the rest of his things and threw them in the wash. Next he made a frozen dinner for ease and then hopped in the shower. It occurred to him that he would have to wear pants because he now had shaved legs.

He got out of the shower and without really thinking about it out on the panties. He grabbed a pair of slacks and a long t-shirt just to be sure his panties didn't show if he bent over.

He was just about to leave when his phone buzzed.

"I know you are wearing the panties, but are you using your other surprise?" Sabine asked.

"I didn't think it would be a good idea, if I were just hanging with my friends."

"Awww, you're no fun!"

"Well I don't need to get all horny for them."

"They won't know. And it'll get me all hot thinking about you having it tickle your insides....pleeeaaasssseee?"

Against his better judgment and inner voice, he texted back, "ok, for you."

"Good boy! Yay!"

He made his way to the bathroom, opened the lube and covered the plug thoroughly. Then spreading his legs with his panties pulled down just enough, slowly inserted it, with a gasp and a slight moan."

It felt different moving it with it inside his ass. It kept his cock constantly chubby.

He grabbed a light jacket and headed out the door.

The Soggy Muskrat wasn't anything special. Just a regular bar with pool and darts. It had better prices than the more upscale places. The wood trim was riddled with light up neon beer signs and whatnot, and classic rock was always playing on the jukebox.

Will and Sam had arrived a few minutes earlier and were sitting at a round table top.

"Hey!" They all simultaneously greeted each other doing the ceremonial half hug, back pat thing.

"So how have you been? It's been a while," Charley asked Sam.

"I've been good. The kids are out for summer, so now it's a lot of shuffling to this sports game and that dance recital....ya know."

"The joy of kids."

"Oh man, they're lots of fun, but these scheduled events fill up our weekends."

Will laughed and cracked his invisible whip.

"How's Becky?" Charley asked.

"Oh, she's good. She started taking a cooking class, so finally she's started learning to make things that are edible."

They all laughed.

"That was needed. God I remember being invited for dinner that one time. Never again." Will laughed.

"Sorry about that man."

"What's been up with you?" Sam asked Will.

"Mainly just keeping up with busy season at work. With all the local development, the business has taken on way too many contracts, so that's had me pretty bogged down. That's fine though, as the whole dating app scene has been pretty abysmal lately. My luck just hasn't been there." Will replied. After a pause, "what about you Charley, still trying the app thing?"

Charley responded, "No, thank god!"

"Ooooh, so you met someone, huh?" Sam chimed in.

"Yeah. Kind of snuck up on me. It was at a company affair. She just found me, and we hit it off."

"So is she a coworker?"

"Well...actually, now she's my boss."

"Woah! Sleeping with the boss?" Will's eyes got big.

"Well, she was way higher in the company than me, but literally the next work day after the party she gave me a promotion and I work directly under her, overseeing the whole department."

"Damn dude. Must've done something right," Will fist bumped his shoulder.

"I imagine that was a significant increase in pay," Sam said.

"Yeah. Pretty damn significant."

"Well don't piss her off!" Sam laughed.

Charley laughed, thinking "You have no idea," but responded, "Yeah, I better not."

"Is she hot?" Will inquired.

"Actually, she's really hot. She's a bit taller than me, brunette, slender, nice long legs..."

Will cut him off, "does she have a big rack?"

"Not really. It's nice, but she's not got huge ones."

"Oh, trying something new, eh? You usually go for large in that department."

"They fit her nicely."

"Good for you buddy," Sam jumped in, "We'll have to meet her sometime."

"Yeah, that'd be great." Charley said.

They continued talking, laughing and catching up through a few rounds, when suddenly, Charley felt the buttplug vibrate for a few seconds almost making him jump.

Sam looked at him oddly, "You alright buddy?"

Charley kept his composure, "uh...yeah...I just though a bug bit me or something. Sorry."

Then his phone buzzed. He pulled it out, and read a text from Sabine. "Hey, I don't want to smother you, or ruin your time with friends, but my girlfriends Lena and McKenzie are bored of this bar and are dying to meet you. Would you mind if we joined you?"

Looking up at his pals, "Speaking of meeting her, she's with a few friends and wondering if they could join us."

"Sure," Sam replied.

"Are her friend's hot?" Will asked.

Charley typed a response, "yeah, that'd be great. We are at the Soggy Muskrat. You know the place?"

Looking at Will, "Not sure, never met them. You'll just have to find out."

His buttplug vibrated for a second again, causing his dick to twitch. Then he looked at his phone, "Yeah, we know the place. See ya in five, my dirty little boy." Two more short pulses tingled his insides.

"Well this is exciting," Sam laughed.

"They should be here in five."

"Maybe I'll break my dry spell," Will laughed, and they made a cheers to it.

A few minutes later, Sabine and her friends entered. As soon as Charley laid eyes on her the buttplug started vibrating. Faster than before. And then it stopped.

Sabine was wearing a simple sleek dark red dress, with little accents along the sleeves and bottom, but otherwise simple.

Her one friend was blonde, had a nice pair although held up by their bra, a little heavier than Sabine but still gorgeous. Her ass was a little more "packed," and her lips were big. She probably was about 5'6" and 140lbs.

The other girl was a twig, 5'5" ish, small everything. She was cute, red headed, and probably was under 120lbs.

Both were beautiful women and they all were approaching the table. The plug vibrated again for as few seconds. Charley popped to life, but his friends didn't notice. They were all looking at the entrance.

"Hey Skipper," Sabine jested shifting her hand on her hip and the other in her purse.

"Hey baby," Charley said enamored with her from the moment she came in, and the plug started vibrating hard. They held eyes for a moment and then it stopped as Sam and Will introduced themselves to everyone.

McKenzie, the blonde, spoke next, "I hope we didn't intrude. But Sabine was talking about you, and the night was pretty fucking boring to be honest. The town was a little too quiet tonight. So I suggested she reach out to you, so....

Will interrupted her, "We were just shooting the shit. Makes it better to have fresh company!"

Sabine looked at Becca and smiled, then said, "Next round is on me. Get what you want." Her last sentence was followed by a gaze that wouldn't let Charley go. She was like a hungry predator and him some sort of prey... and it buzzed a few times...

Becca looked at Sabine, "We should do a shot."

McKenzie jumped in, "Tequila!"

Sam pondered, then said, " if I have a shot of tequila, it's my last for the night and I'll be drinking light from here."

Sabine interjected, "Sam, if you aren't up for a shot, I can just get you a light beer..,," she had a cocked smile....

"Well damn...shot it is..." Sam metaphorically took a knee.

"Damn," he looked at Charley, "where did you find her?"

"I found him," Sabine cut in.

"Speaking of which, Sabine has been gleaming every time she talked of you. What kind of wicked magic have you worked on my friend," Becca said.

Charley laughed, blushing, and said..."She's a witch... it's her spell. You'll have to ask her.. " the plug came alive again as soon as he finished his sentence.

"ILL GET..." the plug stopped, " The shots...." Charley jumped up, and made his way to the bar.

"He's cute," McKenzie said.

"He's mine," Sabine shot a menacing and yet sarcastic look at her friend.

"Well then.." McKenzie jested back.

Charley returned a few moments later and then the bartender delivered them their drinks.

Sam piped in, "Is it hard, with her being your boss during the day and your love interest outside of it?"

Sabine, "I think we figured it out. And who is to say I don't continue being the boss outside of work?"

"Woah," Will laughed, "watch out for her,Charley."

Sabine replied, "Seriously, we work quite well together, so it hasn't presented too many hurdles. "

"You're a lucky guy, Sabine is stunning, Sam leaned towards Charley and said it quietly."

Becca stood up, grabbed her shot glass and raised it, "To the love birds!" The rest grabbed their glasses and clanked them.

The banter continued for a while, Will trying to hit on McKenzie throughout the conversation. It was questionable as to whether he was making progress.

Sam got up and suggested they play some pool. Charley and Sabine decided to let the others play first and swap out with the losing team. As they gathered around the table Sabine put her arm on the small of Charley's back. She leaned in and softly kissed his neck, then let her fingers slip below his shirt and into the waistband of his trousers. She ran her fingers over the top of his panties, then just turned and smiled at him. The buzzing inside him started again.

A worried look came across his face, not wanting to get to noticeably worked up in front of everyone. She giggled, then it stopped.

"You are trouble,"Charley gave her a look.

"You knew I was."

For the moment it looked like Sam and Will were playing better than Becca and McKenzie. Will called a shot, looked at McKenzie, and said, "How about a wager? I make this shot, I get to take you on a date. If I don't, I stop suggesting it altogether."

McKenzie, visibly pretended to think hard for a moment, then replied. "Okay. Make that shot, player..."

"Oh, it's in the bag," Will replied in a cocky way.

He leaned in, lined up the shot and...missed. His head just dropped. "Well, I guess that's that."

Feeling bad for him or something, she laughed, "I prefer men that can actually deliver, but I guess I can still let you take me on a date. "

Will looked at her and chuckled, "Not all is lost."

Becca, waiting for her turn, looked at Charley and Sabine leaning against each other. "You guys are too cute. Although, i'm still not sure how you reigned Sabine in. She's always been a little too driven and intimidating for most guys as far as I know. Not many seem to catch her interest."

"Must be my incredible butt," Charley laughed and teasingly wiggled it.

Sabine let out a belt of a laugh, looked at Becca, "Oh yeah, you have no idea...it's hypnotizing."

"And don't for one minute think I'm not intimidated by her," Charley said and winked.

"Gawd, you two are adorable."

They were interrupted by Becca's turn. She played it well, and now they looked like they had the upper hand. One shot away from the eight ball.

Sabine shot a quick text to Charley. His phone buzzed, "Can you imagine what they'd all think if they knew you were dressed in those pretty little panties with a plug stuffed in your ass?"

The vibration started again, right as Charley looked up at Sabine. She kept it going for a few seconds, but it stopped as Becca turned to face them.

"So what drew you to Sabine, aside from her looks."

"I think her drive and determination is what I like most. She seems to know what she wants."

"Oooo, good answer." Becca responded.

Will had started getting a little handsy with McKenzie, and the alcohol seemed to be helping her accept his advances.

Sabine hollered across the table, "Will, looks like you finally broke her down."

"I did show some fancy moves on the table..."

"Hopefully your moves elsewhere are better than those..." McKenzie jested.

Charley looked at Becca, seeing she had no ring on, asked, "So Becca, are you seeing anyone?"

"You trying to pick up my friend? " Sabine joked and gave him an elbow.

" No, not currently. I seem to attract nothing but pigs.and this dating app stuff is shit."

"Yeah, I can understand that," Charley responded, "I never had much luck there myself."

"At least I have friends like Sabine who can spot an asshole like a hawk. She's saved me from some bad ones a few times."

"Got to take care of my girls. Guys can be such asshats. That's why you're perfect for me. You're arent really a guy...." She said the last line snickering, and gave him a pat on the ass.

"Ohh!" Charley got wide eyed.

She looks at Becca, "He's pretty exceptional, and definitely my type of guy."

"You two are fun together. I love the way you play with each other." Becca said. Sabine gave her a hug in response and a friendly peck on the cheek, then with her arms around her gave Charley a hot look and blew him a kiss.

"I know, it's perfect isn't it."

Becca and McKenzie had put Sam and Will in their place. It was Charley and Sabine's turn to play.

"Finally, a chance at some competition," McKenzie blurred out. "The team we played had someone who could only talk big," she looked over at Will and laughed in a flirty way.

"So are you any good at pool?" Sabine asked.

"I have no idea what I'm doing, but sometimes I get lucky."

"Well, you might as well have said we're fucked." Sabine replied.

Sabine had knocked two stripes in. Becca got three solids. Charley went to shoot, and as he bent over and was about to make contact with the pool stick, his plug began to vibrate, causing his aim him to jump a bit and end up missing his shot and sinking a solid.

"Apparently using your stick isn't your strength,"Sabine laughed.

"I guess not," he looked back at her with a sarcastically judgmental face.

She wrapped her arms around her and kissed him.

McKenzie called the 8 ball, but didn't land it. Sabine ended up sinking the rest of the stripes and called the 8 ball for the corner pocket.

A deep breath preceded her shot, but she landed it.

"Damn! Watch out Charley, she's pretty good at knocking balls around!" Will chimed in.

"You have no idea," Sabine said back. Then she gave Charley a big kiss, wrapping her arms around him.

Both Sabine and Charley were a bit tipsy at this point. McKenzie was pretty drunk, stumbling over herself and Will was no better.

McKenzie spoke up, "I think I need to call it a night."

"I can call you a cab," Will spoke up.

"Yes, thank you!" She said

They wobbled off saying their goodbyes. Sam peeled off to get home, "The wife doesn't like when I stay out too late. So I should probably get going. It was great meeting you all, and we'll hang out soon Charley!"

"One more?" Becca asked Sabine and Charley.

Charley glanced at Sabine waiting for her to answer.

"Sure. That sounds good."

They ordered another beer for each and sat back down at the table.

"I still can't get over how cute you two are." Becca said.

"Thank you."Charley said.

"I tend to think so," Sabine said with a warm glance at Charley." Her hand rested on her thigh. Her other hand under the table, and the buzz of the vibrating plug began again.

Charley tried his best not to show it on his face, but sitting at that angle had his cock groaning in it's confines. Sabine's hand casually brushed across it a few times.

After a little banter, Becca excused herself to the bathroom.

"Enjoying my little gift," Sabine squeezed his cock through his pants, still hard from the on and off sensations pulsating in his ass.

"You definitely have caught me off guard a few times."

"Good..." then switching the subject. "Becca's a pretty cute little thing isn't she?"

"Yeah, she's very pretty."

"I do wish she'd find someone nice though. She tends to always attract the wrong type of guy."

"That's a shame."

"I'd love to spend the night with you, but I should probably get her home after this. Maybe we can do tomorrow night at my place?"

"I'd love that."

"Good. She gave him a sweet kiss."

Becca returned to the table.

Sabine sipped down the rest of her beer, then looking at Becca, said, "Should we get you back home?"

"I would appreciate that."

Becca looked at Charley, "It was really nice meeting you, Charley. "

"You as well." Sabine gave him a brief hug and they all made their way out. Sabine glanced over her shoulder and blew him a final kiss before disappearing around the corner.

Charley got home, removed the plug, hopped into bed, and fell asleep in his panties.

The next morning was dark, cloud covered and spewing rain from above. Charley was in no rush to get up, and lingered in bed for a bit.

A text buzzed on his phone. "Hey lover, I had a good time last night. Thanks for meeting my friends."

"It was nice to meet them."

"Guess what!"

"What?"

"Some of our packages arrived."

"Oh yeah?"

"So that should make for a nice night. Any interest in grabbing some lunch together?"

"Sure."

"I will pick you up at 11:30, does that work?"

"That sounds great to me."

Charley sprung out of bed and began to get ready. It was already 9:30.

Her ETA came upon him quickly, and he was startled by a knock at the door. He opened it. Sabine was wearing a cute white sundress with yellow flowers. "You look gorgeous."

She leaned in and kissed him. "Thank you. Did you sleep alright?" She stepped inside and closed the door behind her.

"I came home and just clunked completely out. You?"

"Becca ended up staying over, so we were up for a bit talking, but then yes. I slept quite well. She drove home this morning."

"Oh, that's cool."

"Sooo...," she pulled him close, and slid her hand down the back of his pants, squeezing his ass..."I see you aren't appropriately dressed for lunch with me."

"Uh..." she reached in her purse and pulled out one of the pair of sissy underwear items she had purchased, with the elephant nose crotch.

Then she undid his pants and let them drop to the floor. She yanked his boxers down and lowered herself holding the underwear open for him to step in. He put each foot in and she raised them slowly up his legs, making his skin tingle. "We will need to shave these again."