Sailing His Ship Pt. 04

Sabines fingers traced down and followed the edge of his waistband, then along the edge of the strap pouch, on his thigh.

"You took dare, and you won't get to stay in the game or get fucked tonight," she looked at the larger boy. "I'm not going to tell, are you?"

"Well, no..but I don't know..."

Sabine's fingers tickled up and down Charley's thigh.

"If you want me to suck either of your cock's, you should at least know how it feels. Plus it's hot. I've always wanted to watch a couple of hot guys fuck around."

She got up and plopped right next too the larger boy, and began toying with his cock. She then spit in her hand and teased the head of his cock.

"You don't want me to get bored do you?" She asked.

She took him by the cock and pulled him forward, then got on the floor and yanked him there with her. Taking the smaller guys legs, and pushing them apart, she licked up his shaft then took one dip down on his cockhead. Pulling herself off of it, she licked her lips, and kissed the other guy. "See, not so bad...," then she put her hand on the back of his head and pushed his head forward toward the cock.

His eyes looked at her pleadingly, in a moment that he resisted. "But it's for me."

He gave, and his mouth moved forward. At first he was gingerly working the smaller man's dick.

"That's hot baby, but you really have to throat that dick, she pushed his head harder, until, accompanied by a gag, the member dove deeper down his throat. "Oh, that's it baby," she cooed.

Sabines fingers now were running up and down the fabric over Charley's cock.

The young man continued relaxing into sucking cock, and looked like he was beginning to get into it, though he wasn't trying to broadcast such. The smaller man didn't want to admit to broadcast either, despite his face was telling a sensation of pure bliss.

"Ok, I'm satisfied for now. Your turn."

Sabine's full hand rested against the pouch of the jock, now with Charley's hard cock straining against it.

Another round and she chose the smaller boy. Being completely horned up from having his cock sucked, he chose dare.

"You have to sit in his lap, and rub his cock between your ass cheeks."

Sabine glanced down at Charley, "your cock is so hard baby." Her hand still very slowly rubbing up and down his bulge. "

The scene was now the boy with the smaller cock straddling the larger guys waist. The girl stroking his cock...

"You know," Sabine said, " I had a few other texts with the server boy from today."

Pure panic rose up Charley's being...

"Remember in your office earlier today...I sent him those."

"Oh, god, Sabine...what if people...."

"They won't...he doesn't want to be found out either. And to be completely honest, I sent him some from the kitchen as well, once you had a nice little smooth body."

"How do you know..."

"I know."

"But..."

"But what. I know your little cock got hard when I talked about him. I know it was dripping when I sent you a pick of him hard and throbbing. I know no matter how strange it feels to you, your panties are soaked when I make you think about such things..." her hand came to his lips, pressed in, and the taste of precum flooded his mouth.

"How did he react?"

"He sent me these..." she grabbed her phone and pulled up the texts.

Several more images of the server's big cock were in front of Charley...the girl on the screen guiding the larger guys cock into the smaller boy's taint.. Sabine giving a quick light slap to Charley's balls.

"That's a nice cock isn't it. It would be so fun to watch that plow your throat."

"I don't kn..." he was cut short by another set of fingers stuffing precum into his mouth.

"I even sent him the one of you with a cock in each end...he blew his load on that one." She said before grabbing the whiskey, placing it to his lips and pouring it down his throat, until he gagged a little, and she licked up the bit running down his cheeks.

The boy on the screen was wailing with pleasure as his asshole was stretched and his cock was being sucked by the girl.

"I so want to see your little ass impaled on him, just like on that screen....." her fingers started rubbing his perineum. "Mmm, baby, just imagine wrapping your little hands around that big cock, feeling how much more of your hand it takes up. Could you even wrap your fingers all the way around it? Making you think about that every time you hold your pencil dick in your hands...."

Charley just moaned to her touches.

"Here, get over top of me with your face to my pussy."

He climbed over her positioning himself in the 69 position.

"Eat that pussy baby."

He dove into a soaked pair of panties, shifting them to the side. Her pussy was unbelievably wet.

Her tongue lapped over his restrained cock and balls. She shifted the pouch a little, keeping his cock trapped, but pulling his balls out. She began sucking one at a time. His jockstrap was riddled with dark spots moist from his leaking dick.

The larger boy now was fucking the smaller one from behind, the smaller yelling. "That's it, take his big dick. Yours won't satisfy me, so now you'll just have too accept that you were meant to be a little sissy," the girl said as she stroked his dangling cock. "That's it bitch."

Charley almost jumped when a new sensation rocked him. Sabine's tongue was tickling his freshly smooth little hole. No one had ever licked Charley there, and it felt foreign and dirty. However the alcohol, and the pussy he was devouring kept him from resisting.

He felt her place a small bottle in his hand. He took it to his nostril and inhaled deeply, holding it for a few seconds...his breathing felt slow, his heart rate increased, and the rhythmic circling of her tongue sank him into a raw place of pleasure and acceptance. Her tongue was now invading his little ring.

She stopped for just a moment. "You like getting your ass eaten don't you baby. You like when I lap at your little sissy pussy?"

"Mmmm" was all the came out as he sucked at her clit, his face wet with her juices.

Tongue circled inside him, then...slap...he recoiled too the abuse of his balls for a second, but her tongue and hands kept his ass pressed back.

"Mmm, that's such a good little girl, Sabine caught her breath for a second. Her hand reached below him and freed his cock from it's prison. He was hard, but the fabric jock had kept his cock from fully being erect. Precum oozed out of his cock and dripped all over her.

"Mmm my baby's so wet.

He moaned as she dove back in. Now the girl on the screen had a strapon and was plowing the smaller boy's throat as he took the large cock in his ass.

Sabine grabbed his cock and balls at the base below the balls and squeezed. A guttural sound came from Charley's buried face. A steady stream of clear liquid now coming from the slit of his cock.

She picked up the pace, driving Charley wild, never knowing have someone eat his ass could feel so good. Her hips started bucking, and as she worked his ass even harder until she pulled back for breath, "oh fuck I'm cumming."

She pulled his face hard into her pussy, grinding into it. When her body stopped convulsing, she said, "baby, I want you to blow your load inside of me.

He repositioned and got between her legs. His now hard, but not quite as hard as usual cock felt so good in her pussy. He started pumping it in, then surprised by a sensation pushing into his ass, felt it start vibrating.

"Oh, my poor little sissy can't get it up for pussy now? Does she need a big cock inside her to get off? Are you imagining how stretched my pussy would be, filled with his cum, and your little prick not even touching the inside walls of me..."

"Oh fuck, he groaned, the feelings combined being too much, and he lost the ability to hold back. He unleashed torrents of cum into her. His orgasm shaking him through his core, until he collapsed on her, his now softening cock slowly sliding out her cum filled hole. Part of him felt amazing. Part of him felt embarrassed. So many questions were circling in his head, leaving him conflicted.

" Now you're going to clean your mess off my tits, my stomach, and out of my pussy you little faggot bitch."

Charley began lapping all his precum from her body, amazed at how much had come out. Then her hand grabbed the top of his head and pushed down." That's it baby, clean that pussy."

Her swollen pussy was oozing jizz when his face got pushed into it. She held his head there, and he just started kissing, sucking and licking it all. He couldn't think about it, just do it, lest he fail to please this gorgeous woman he was having way to much fun with. Her hand eased off. Once every bit had been swallowed he came up for air.

"What a good little bitch. Now go get a quick shower.."

Dumbfounded, post orgasmic, and...obedient, he shuffled to the bathroom. Starting the shower, hopping in, a quick soaping, and a quick rinse.

"Leave it on for me," she said as he saw her remove everything and open the glass door. She got herself under the water for a brief moment while she kicked on the other shower head. She also quickly washed silently. Once she had covered all objectives she turned around too see Charley just happily watching her. She leaned in, wrapped her arms around him, held an ass cheek in each hand, and gave him a deep passionate kiss.

As she pulled back she just looked intently in his eyes, "Charley, im pretty sure I'm fallling for you. I like us, I like this. And if I cross a line...well...truly cross a line for you, you just need to tell me."

"Sabine, these have been some of the best days I've ever had. But sometimes I feel a little confused and conflicted."

"For the record, I am absolutely happy with you, and my...desires and fantasies just come spewing out. You are absolutely enough. But you can't deny that me toying with you is great fun for us both."

"I can't deny it turns me on, but I'm still a little freaked out about you telling the server."

"She leaned into his ear...I didn't really tell him. I sent that from my other phone to myself. They're just saved images from..."

"You mean you've been fucking with me the whole..." he said feeling relieved

"I'm pretty sure you like me fucking with you," she smiled.

"Wow, you had me going. I was trying to figure out how to process the whole thing in my head."

"Charley, I'll process it for you. Before you knew it was a ploy, you got all hard thinking about it. Just like you do for me. It made me so hot. And even though you felt conflicted, you kept inviting it and eating it up. It doesn't need a label. It doesn't need an explanation. So you get off on being made to feel small,.. smaller than you really are. So what if a woman suggesting homoerotic behaviors turn you on? So what if you're girlfriend likes emasculating you, while adoring you at the same time? I am not looking for anything but this...the rest..it's just having fun and finding it's fun for you too, " she gave him a soft look and kissed him gently moving her hands to his face.

"So you're my girlfriend?"

"I better be."

"I thought you didn't want labels."

"Let's just say I want this. All of this. All of you."

He pressed her against the shower wall, she gave in. A torrent of kisses met her lips, her cheeks, her neck, her shoulder, and her forehead. Then pulling back and looking into her eyes. "I love us."

"Good girl."

She shut both the shower heads off. "Let's get dry and go on the back deck for a minute.

They dried off and she grabbed two silk robes. She handed him one, grabbed his hand led him outside. The air was cool, and after a hot shower his skin was tight, and his cock completely shriveled. It was comfortable temperature, but it took a minute to adjust.

She pulled out a joint and lit it, "care too partake?"

"I thought you'd never ask," he replied as she took two hits and passed it to him.

"Now you know." He took a few tokes as she spoke.

"I needed that."

"Good. Me too."

A moment of silence lingered as they passed the joint a few times. Her hand rested on the small of his back.

She took a big hit, then kissed him blowing it into his mouth. He held it for a moment then exhaled.

"You're cock was totally hard thinking about that server, and him having a bigger dick than you." She said as she reached inside his robe as he took a drag. Her hand wrapping around his withdrawn dicklet.

"I can't deny that."

"No you can't"

"Could you imagine his reaction if this is all he saw. This tiny little worm," she chuckled as she teased it with her finger tips.

"It wouldn't be my proudest moment."

"I bet you were secretly hoping i did send those pictures."

"I guess, a part of me liked the idea," the pot was kicking in as he spoke.

"Hmmm"

Sabine paused to take a few tokes of the joint before putting it out.

She took his cock in her hand (that had grown beyond it's previous state) and led him back inside.

They returned to the bedroom. She let go and peeled back the covers. She sauntered over to her dresser and pulled out some cotton, striped, white and purple panties and handed them to him.

Charley slid them up his legs. The were stretchy and comfy.

She slid underneath the covers and laid with her back to him. "I want to be held, lover."

He slipped in behind her and wrapped his arms around her. "You are so amazing, Sabine."

She nuzzled back into him, "You feel so right to me."

"That makes me happy."

Charley's eyes opened, unsure of what time it was. The sun hadn't risen yet, and the lights were still on in the bedroom. He carefully slid himself out of bed and made his way to a much needed release.in the bathroom. Then he flipped out the lights and snuggled back ino bed and nestled himself against her, letting sleep take him again.

The alarm clock screamed, she smacked it, grumbling some expletives, then hit it again. It's cries diminished.

"What do you say, we call a sick day?"

"His groggy mind tried to grok what he heard."

"I mean, I call a sick day, and you report to me,..,so you can request one right here. I could use some more sleep. If anything pressing comes about, im sure they'll call or text, "

His head hurt a little from the night before and he still was gaining his senses, but the suggestion was weighed heavily on the "pros" side of things,

With a few worlds tapped into her phone, all was handled. Then she collapsed back into his arms and fell asleep. He leaned in and wasn't far behind.

Charley woke up to an empty bed. The air smelled like breakfast was cooking. He shuffled out of bed and took a piss. Then made his way toward the smell.

"Good morning, cutie." She said in a chipper voice.

"Good morning hot-stuff," he replied, still only wearing the cotton briefs."

She handed him a cup of coffee, and suggested he go sit out on the deck. "I'll bring you this when it's ready."

It was about 70 degrees, the sky blue and the birds chirping away. He still wasn't sure what time it was, not that he cared really. He sipped his coffee and leaned over the deck admiring a truly beautiful day. A slight breeze rustled the leaves on the trees and tickled his skin.

He heard the door slide open behind him and Sabine came out in her silk robe, nipples poking through the fabric and carrying a plate of eggs, toast and bacon.

"Here ya go babe, he took the plate from her and sat down at the patio table. She went back in and grabbed her plate then joined him.

"Thank you so much. This is really nice" he smiled at her.

"Well, I do have to keep my lover happy."

"I think you've successfully maintained that."

"Perfect," she said. "So, I was thinking, maybe we lounge around for a bit and do some online shopping. I'd love to pick out some more fun things to have you wear."

"That sounds like fun."

"Good. I enjoy dressing up that little booty of yours." Her hand brushed his leg, and his skin jumped, as he was still adjusting to being hairless on his legs. "Later I'm going to take you home. As much as I would love your company tonight, I promised one of my friends that I'd go hang out with her. "

"That works baby. I may try to catch up with a few of mine.

Once they had finished breakfast they went to her living room. She connected her phone to the large tv, and began pulling up different sites.

"Ooo, how would you like that one?" She said as a black little pair of panties with lacy edges appeared on a woman. "I think those would look great on your ass. Don't you think you'd look so pretty in those."

It was strange to be called pretty. But his brain couldn't resist her, and it was always getting befuddled with her games. "Yeah, I do."

She added them to the cart and kept scrolling. She selected a few more, some frilly, some lace, some thongs, a garter, some with bows on the front, some with bows on the back. "These with the bows on the back make me feel like your a little birthday package I'm about to open."

"You can unwrap me anytime."

"Good girl. I also want to get you some stockings. You'd look really cute in some knee highs and thigh high's."

She selected various lengths, patterns, and colors. She checked out from that sight, selecting fast shipping. "Hopefully these arrive before you stay over next."

"Already scheming, I see."

"When am I not."

Then she pulled up a site dedicated to "sissy clothing." The images were framed around the men's asses and cocks, all soft and trapped in the fabric.

"This is fun...." She pulled up a pair of sissy underwear with an elephant nose crotch. There was a sleeve for the shaft and an opening at the end for the head. "I can think of some ideas for this." She added a few colors to the cart.

She traced her fingers down the crotch of his panties, feeling his semi-erect cock. "Ooo, is somebody getting turned on thinking about wearing these for me? Or, is someone getting turned on looking at all these cute boys and their cocks?"

"Umm..."

"So both, huh? She laughed, then selected some more lacy things, some with leg cuffs, some with an open ass, different pouch sizes. "These will do."

She checked out like she did before and switched to another site, mainly one of jockstraps.

"You've probably spent a fortune by now, are you sure you want to...."

"Honestly, it's nothing, and just as much for my fun as yours. "

"If it makes you happy."

"Oh, it does."

She scrolled some more, pulling up a few.

"Ooo, I like that one. It'll frame that ass nicely...and this one will frame that package perfectly...oh my, this one will trap that cock," of course she ordered each she mentioned.

"Wow, you have plans apparently."

"Should I not?

"I'm not complaining."

"Good," she said as she kissed his cheek.

"I need to head to the facilities..excuse me a moment."

"Oh, the little boy's room?"

"If you so label it..." he joked.

Charley made his way to the bathroom. Relaxing he hadn't glanced at his phone or looked at a clock that day, he took a gander at the one in the bedroom prior to relieving himself. It read "1:45pm."

"When did I wake up," he thought.

Upon his re-entrance Sabine stood up and said, " what do you think about a snack and then I take you home. I need to tend to a few things that I haven't the last few nights."

"Yeah, I should probably water my plants."

"I told you we could bring them...but yeah. So about this snack..."

"Did you want me to make something, or grab something on the way. "

"I have sandwich stuff."

"Ooo, sandwich stuff," he laughed at her choice of words.

"Shut up," she acted sarcastically hurt.

A sandwich later and a few more prods here or there, the time had come....

The ride was kind of silent. A relishing in the last few days, a grieving of a feeling on pause, joyful and sombering at the same time.