The gray skies were starting to clear as Billy expertly piloted the boat to rest alongside the dock. Cutting the engine, he quickly tossed lines to Toby and Ali. They pulled the boat in against the dock and tied it to the waiting cleats. The bumpers Billy had put out squeaked as the low waves in the harbor gently lifted and lowered the sailboat, their home for the next week, up and down. His parents had graciously offered to let them borrow it for the trip, a vacation for the group of the childhood friends, reuniting after another year away at different colleges.
Ali and Toby had arrived on the island on the same ferry the day before. They met up at the terminal and spent the whole crossing talking non stop about what we’d been up to for the past year and their upcoming adventure. The conversation was just starting to slow when the ferry docked and they disembarked, walking off with their bags and scanning the waiting crowd for Billy. He waved them down and greeted them warmly then led them to the car. On the way to his parent’s vacation house they stopped in the little town to get dinner and supplies, Billy leading them to all the best shops and avoiding the tourist traps. Ali and Toby followed along, remembering some of them from previous visits.
They stopped at a hardware store, a bookstore, and a boutique where Ali picked out a new bikini. They picked up dinner from a little restaurant and, having planned their meals ahead of time, they made an efficient trip through the grocery store, splitting a week’s worth of food, snacks, and drinks. With their packed bags still in the car, it was a tight fit as they took the short drive to the house. They unloaded the food, dropped their bags where they would be sleeping, and sat down to eat and continue to catch up.
Each of the friends took turns telling each other of their adventures throughout the year, the trials and tribulations of their freshman years in college. From the way Billy told it he’d spent most of the year partying, but seemed to have spent enough time focusing on his classes to at least decide that he was probably going to major in some form of engineering, or biology, or maybe business. Ali had been much more studious, always knowing she would study psychology, and was well on her way to getting her prereqs out of the way. Toby’s experience had been somewhere between the two. They still weren’t sure of the direction they wanted to go, but had become more comfortable with his non-binary demiboy identity, using gender neutral pronouns full time now, not just with their friends. The conversation broadened as the night drew on. They reminisced, shared their dreams for the future, and discussed the trip they had ahead of them until they couldn’t keep their eyes open any longer.
…
They were all yawning in the crisp morning air as they loaded the boat, none of them having gone to bed until the small hours of the morning. Their bags were thrown haphazardly into the cabins, then the food passed down to Toby in the galley. Designated as chef for the trip, Toby loaded up the cabinets, fridge, and freezer with the provisions, then started the kettle, boiling water to make tea for them all. While Toby did that Billy and Ali set about making the boat ready to sail, doing a final check of the lines, the dingy, the fuel and water tanks, the computers and electronics, and everything else the boat needed to set sail. When the final checks were complete they locked up the car, grabbed some pastries from the cafe, and cast off.
The calm sounds of seabirds and lapping waves in the harbor were punctuated by the staccato hum of the diesel motor as it pushed them out into the bay. While Billy navigated them towards open water Ali and Toby went inside to get the cabins set up. Ali had the cabin in the bow and Billy and Toby would be sharing the one in the stern. The dining table could be turned into another bed, but Billy and Toby said it would be too much hassle. The real reason they were sharing had more to do with what they expected to get up to at night. Billy and Toby had been experimenting and eventually having sex since they hit puberty. It started as messing around after the lights went out during a sleepover and instantly became the highlight of any time they could get together. Slumber parties, camping trips, and days left home alone all had the extra thrill of lust.
Ali was the only one who knew, having caught them once at a sleepover birthday party at Toby’s house, the first that their parents decided Ali had to sleep separately from the boys. Toby had been disappointed that they wouldn’t be able to stay up all night talking together but excited by what Billy and Toby could get up to instead. They were making out and touching each other under the blankets with their underwear around their ankles when the doorknob slowly turned and Ali snuck into the room. She didn’t see much, but their frantic shuffling and Billy’s empty sleeping bag on the floor told the story. Her only response was a tactful raised eyebrow while they pulled on their underwear under the blankets.
As they got a little older and it became easier to get time alone together the sex became more frequent, then one day it stopped all at once. Billy wanted to ask a girl out and didn’t think it would be right to be sleeping with them at the same time he was going out with someone else. Toby didn’t want to stop him, she was really cute and they were sure she would say yes, and they’d never talked about a relationship. They were just best friends with benefits. Still, they missed more than just the sex when it was over.
Billy’s relationship came and went, plus one or two more but they didn’t get back together, just friends through highschool then away to university. Toby had a couple flings this last year at school but nothing that stuck. All three of them were single going into the trip, a situation that had all of their brains spitting out fantasies port and starboard, unbeknownst to one another.
…
“That’s done,” Billy announced from the other side of the table, exhaling more smoke into the already hazy compartment, grimacing at the now acrid taste coming from the roach in his fingers.
“Give it to me,” Toby said and took it from his outstretched hand. “I gotta pee anyway.”
Ali hadn’t smoked in a while and was blissed out on the bench next to them, head leaning back listening to the smooth electronic music playing throughout the boat. When she didn’t show any sign of getting out of their way Toby stood on the bench and stepped over her. Their first real night on the boat and already the main cabin was a bit of a mess. Remnants of dinner and snacks filled the galley, drink cans and playing cards fought for room on the table. Their heavier layers, necessary earlier when they were outside in the evening chill, were now discarded around the cabin.
Toby climbed up the stairs and opened the hatch to the stern. The cool crisp air was a sudden contrast to the smokey humid warmth below. They walked out into the dark and took one last puff off the joint while looking up at the stars, then flicked it into the water. They spent another minute marveling at how little light pollution there was out here before unzipping his fly. They heard the hatch and Billy’s footsteps as their stream started to splash into the ocean. They assumed he needed to relieve himself as well and would wait his turn or go off another side of the boat. Instead he walked up behind them and wrapped his arms around their chest, pressed his body against mine, and leaned his head over their shoulder.
They were both a little drunk, a little stoned, a little cold in the ocean breeze. He was warm and strong behind me, and sounded confident and playful when he whispered into Toby’s ear.
“I want you.”
He swallowed hard and responded in a voice that sounded more like begging than they meant it to.
“Yes please.”
One of his hands drifted lower, eventually brushing mine aside to take a gentle hold of their cock. He held the tip between two fingers, pointing it upwards so the stream formed an arc and made as much noise as possible when it hit the rippling water below. His feet shuffled closer and he felt his erection press against their ass.
“I haven’t been able to think about anything else for weeks, months maybe” he whispered urgently, then began to kiss and nibble their ear. “No one at school was ever as good as you.” As their stream tapered off he started to stroke their cock slowly while telling them how good he was going to fuck them later.
“What about Ali?” Toby asked.
“Sure, her too if she’s into it,” he responded.
“No you idiot,” they giggled. “What if she finds out?”
“So what if she does?”
I was going to say more, but he started to kiss their neck and found the spot where their neck meets their collarbone that makes them melt and they stopped thinking about such things.
They did have enough cognitive function left to consider that if they left him in this state he wouldn’t be able to last as long later in bed as he had been bragging about. They softly took their hardening cock from his grip and tucked it back into their pants. They turned around and knelt on the teak in front of him, lifted his shirt up and saw the head of his uncircumcised cock poking up past the waistband of his sweatpants. They ran their hand up his leg and over his cock, leaned in to swirl their tongue in his bellybutton, then down, to play with the head of his cock with their tongue and lips.
Billy groaned loudly. They were glad of the loud music in the cabin that would mask it from Ali, assuming she hadn’t completely passed out. They pulled his waistband down below his balls and started to play. His cock was long and thick and would have eclipsed their more average member if they pressed them together. Toby could fit about half of it past their lips before it began to be a challenge. They took it deep for a bit, then kissed and licked up and down his shaft. After sucking and stroking his cock for barely a minute they could tell he was about to explode. They knew he would be pent up and have a huge load so they pulled off and let it shoot into the ocean for a moment, then took his pulsing cock as back into their mouth. His hands gripped their hair, pushing and pulling, shoving deeper and fucking his cum down their throat. It was a familiar taste, nostalgic, neither good nor bad but one always associated with a pleasure in their memory.
He fucked their throat then held them as far down as they could manage. Toby had underestimated the amount of cum he still had for them but was able to swallow most of it. They looked up into his eyes while his cock twitched a few last times and saw his relief and satisfaction, plus a spark of something more.
Alone in the cabin Ali decided now was as good of time as any to use the head. She giggled a little bit at the pleasant way her head spun a little as she stood up, a result of the booze and the gentle rocking of the boat, and was grateful again that she didn’t get sea sick. She was happier than she’d been in months. The stress of school and everything that came with it were melting off. It felt so good to finally let loose after such a long year of focusing strictly on her studies. The only thing that could have made this trip better was someone to share her bed with at night. She’d had a few nights with a boy at the beginning of the year, but a combination of her focus on school, and poor luck at the few social events she’d made it to, resulted in a dry spell lasting the rest of the year. She had her vibrator tucked away in one of her bags with her underwear, but she would have much rather have had someone warm and strong to get her off.
Ali was just about to pull down her shorts, thinking about how unfair it was that the boys could just stand up and go off the back of the boat, when she glanced through the small porthole in the bathroom that looked out onto the back of the boat from just above the deck. The light was dim and her view not entirely unobstructed, but there was no mistaking the scene that was going on before eyes. She bit her lip as she watched Billy with his arms wrapped around Toby’s smaller frame and his lips pressed against Toby’s neck. Memories of catching the two of them in bed together came flooding into her mind’s eye. She felt a little embarrassed to be spying, but as Toby turned around and dropped to his knees there was no way she could tear her eyes away.
She could feel herself getting wet as she watched, and almost subconsciously her dominant hand slid over her body and under the waistband of her shorts and panties. Her fingers slid past her clit to her entrance, feeling just how wet she was, then using some of that wetness as she played with her clit. She wished she had her toy, but it was in her cabin and she thought if she went to get it she might miss the whole thing. As she listened to Billy’s moans and suppressed her own, she started to imagine herself in Toby’s position, then what it would be like for both of them with their hands all over her body.
She was annoyed when Billy didn’t last long enough for her to finish. Feeling pent up and frustrated and like her pussy might start dripping through her panties, she finished using the bathroom as the boys headed back inside.
Toby let Billy pull him in for a long deep kiss when he stood back up, but pushed his hands away when he reached for his cock. “Not now. We’ve been out here too long already,” he whispered, looking back at the hatch to the cabin. “Ali’s gonna come looking if we don’t go back in soon.”
“I don’t care,” Billy replied in a low voice that was almost a growl, looking into their eyes. “I want you and I don’t care who knows.” Toby felt their cheeks start to burn at the passion in his voice and his eyes that told them he meant he wanted them for more than just sex.
“Well I do.” They tried to change the subject quickly, not sure how they felt about the emotions he’d sensed in his friend. Despite having sex regularly they had always just been friends with benefits, nothing more. He swallowed hard as he looked into the taller boy’s eyes, so full of lust and longing. It was hard to resist his friends’ desires, and his own, but the fear of the embarrassment he’d feel if they were caught by Ali again won out.
Billy’s laughter finally broke the tension as Toby reached out to tickle the side of his stomach, a tactic they’d often used to get away when the two would wrestle when they were younger and he was using.
“Fine, fine,” Billy said through his laughter, stepping back. “You win. I’m going to get you back for that later tonight though.” He tweaked Toby’s nose then turned around and walked back inside, stumbling just a little from the intoxication and the rocking of the boat. Toby took a few moments to collect themself before following, taking a deep breath to settle his nerves and letting their his erection settle down to something less noticeable through his tight shorts.
There was a different energy in the cabin when Toby descended back down, a bit of awkward tension in the air. Ali was worried about the redness of her cheeks, even though she could have passed it off as a reaction to the alcohol without even lying, but Billy was oblivious and Toby too focused on trying to get their cock to settle down. Billy wasn’t making it any easier with his little touches and meaning filled glances.
They talked about the forecast and where they’d anchor the following day for a while until, with an exaggerated yawn, Billy announced he was ready for bed. Toby and Ali quickly agreed at the same time, talking over one another in their haste to escape the awkwardness they each thought they were experiencing alone. With a little giggle and a quick hug the three retreated to their separate rooms.
Toby barely had time to close the door behind them before Billy pulled them down onto the bed and started to tug at their clothes. They could only laugh at their friend’s eagerness as they let him pull off their shirt. Billy kissed their chest aggressively, occasionally sinking his teeth into their skin hard enough to leave a little mark, as he pulled their shorts and boxer briefs off together. Once he had Toby naked he descended on their cock without hesitation, making up for a certain lack of skill with enthusiasm. Toby dropped their head back, lost in the pleasure as Billy’s hands and mouth roamed over his body. They held a hand over their mouth to silence a groan as he took his balls into his mouth one at a time, sucking gently while his hand stroked his cock up and down. It was only when his tongue started to move lower that they stopped him.
“Wait, I need a shower first,” they said, knowing what Billy had planned next and pulling his head away. Billy groaned and flopped down onto the bed.
“Fine, just hurry,” he said with a grin and sarcastic sigh.
Toby stuck out their tongue at his friend then dug through a bag for their pouch of toiletries, thanking themself silently for including a bottle of lube in with his other things. Stepping through the door into the head, they blew a kiss and winked at Billy and closed the door behind them. They didn’t take any extra time getting ready but they also didn’t rush. They took a few deep breaths to relax as the hot water ran down over their head and they rubbed themselves all over with soap. Squirting out a bit of lube, they made sure they were ready for the night ahead, then rinsed off the excess, turned off the shower and dried off.
On the other side of the boat, Ali had immediately stripped off her clothes, dug her little vibrator out of her backpack, buried herself in blankets to mute the buzzing, turned it on to a low setting and held it against her swollen clit. She bit her arm to stay quiet as the first waves of gentle pleasure washed over her and she imagined what was going on in the other cabin. The sound of the shower running brought her out of her reverie for a bit, thinking there was no way they were done already, until she realized why one of them, Toby she assumed, might want to be clean before they really got started. When the shower turned off she turned her toy up and let her imagination run wild.
Suddenly a little embarrassed, Toby hesitated before opening the door back into the cabin he was sharing with Billy. They took one more breath and turned the handle, and any hesitation vanished when they saw Billy waiting naked for them and the way he looked back at them. Without a word Billy took their hand and drew them back down onto the bed, laying the wet towel down on the bed underneath them. He kissed and caressed them again much more gently now. His hands wandered over their still damp skin as his tongue pushed its way through their lips to explore their mouth. Toby didn’t resist at all, finally letting go of their reservations and giving up all control of the situation to Billy.
For a while they made out, Billy’s body pressing Toby’s down into the bed. When they finally had to break away for air, both of them panting as they stared into each other’s eyes, Billy could no longer resist and rolled his friend over onto his stomach. His lips started at Toby’s neck and he kissed his way down their back. His hands squeezed their butt then one of them slid under his hips, lifting them up a little then wrapping around their cock. It was as hard as his own as he rubbed against their butt, feeling Toby press back against him. His mouth moved lower and lower, past the small of his back and to his cheeks. He gave one of them a nibble then pushed his tongue between them. Even through the blanket Toby bit down on his moan of pleasure was very audible as Billy started to eagerly tongue his hole.
The feeling was unfamiliar but oh so pleasurable, and soon Toby had to tug his friend’s hand away from their cock to keep the feeling from overwhelming them. The last thing they wanted to do was cum this soon. Billy resisted for a moment, then took the opportunity to use both his hands to spread Toby’s cheeks wider apart and push his tongue in a little deeper.
“P-please,” Toby groaned after a few more moments. “Please, I…” He couldn’t even come up with the words to finish the sentence, but it was enough for Billy. Kneeling with his legs spread out over Toby’s legs and taking the bottle of lube from where they had set it on the bed, he squeezed a generous amount between their cheeks. Toby gasped a little at the cold, and then pushed their face down into the pillow as they felt Billy start to rub it in with his middle finger.
“Good boy,” Billy whispered into Toby’s ear as he felt their hole relax as he massaged it gently, taking his time. A little harder and the tip of his finger popped inside, and he heard a whimper come from Toby’s covered face. In and out his finger slid, and as it got easier he added a bit more lube, then slowly added a second, feeling his friend’s hole stretch around them. He stroked himself a little as he continued to warm Toby up, precum squeezing out in anticipation.
“I-I think I’m ready,” Toby squeaked out, turning their head to look back at Billy behind them.
“Are you sure?” asked Billy, not wanting to hurt his friend. Toby just nodded in response, a blush and a grin growing on their face, even though they weren’t entirely sure.
“You’re not that big,” they teased.
Needing no further encouragement, Billy slid his fingers out and squeezed out more lube onto them then rubbed it onto his cock. He angled it down until the tip was pressing against Toby’s eager hole. They raised their hips up a little further and pushed back as Billy pushed forward. Toby almost regretted teasing their friend when the head of his cock started to stretch him wide, but as soon as it popped inside the feelings of pleasure running through him overwhelmed any indecision.
“Fuck you’re tight,” Billy groaned, causing Toby to blush even harder.
“Shh,” they hushed him. “Ali might still be awake.”
“Mmm, fine,” Billy moaned as his cock pushed further into Toby’s ass. The words were barely any quieter, making Toby wonder if Billy had actually heard, but then they felt his cock pushing against his prostate and any objections were lost, overwhelmed by the waves of pleasure coursing through him.
“Oh god, Billy,” they gasped before he grabbed a handful of their hair and pushed his face back into the pillow and his cock bottomed out inside his friend. He gave Toby a few minutes to get used to the feeling then started to move again. As he started to thrust slowly in and out he could hear Toby still making noise. Was he crying?
“Are you ok?” He asked with concern, letting Toby lift up his head. “Should I stop?”
“Don’t you fucking dare,” they replied, wiping their eyes and looking back. If they were crying, they were tears of pleasure, and the lustful look in their eyes made Billy grin. Reassured, he grabbed Tobys hips with both hands and started to fuck him earnestly.
“Silly boys,” Ali thought to herself in her cabin, able to hear every grunt and moan. “Billy at least should know how easy sound passes through a boat like this. Or maybe he does and he just doesn’t care.” That last thought made a shiver run up her spine at the idea of him wanting to be heard, maybe even wanting her to join in. She turned her vibrator up one setting higher, and almost immediately felt the orgasm that had been building inside of her break through her control and wash over her. It was the first one she’d had in a week, and she knew it wouldn’t be the last she had tonight. She rode it out, making it last as long as she could, then turned her toy off to give her now extra sensitive clit a break, and started to use her fingers instead. She slid two inside of her for a little while, listening to the boys fuck so close by, imagining what it would feel like to have one of them inside her instead.
…
…
Despite normally being a late sleeper, Toby woke up first. They were immensely comfortable between their two friends but knew they wouldn’t be getting back to sleep, so after waking sufficiently they extricated himself from the bed with as little disturbance to their bedmates as they could manage. They knew from experience that Billy would wake up when he was ready and it would take more than a little shuffling to get him up early, but Ali was curled right up next to him and was a lighter sleeper. Once he’d managed that and found a clean pair of boxer briefs to pull on they padded out into the galley to start boiling some water for tea. While they waited for the kettle they wandered out onto the deck. A quick look around told him that they were still alone in the picturesque cove so they stretched and relaxed openly in the morning sun.
Toby was standing on the bow admiring the view when they heard soft footsteps coming from behind him. They could tell just from the sound that it was Ali.
“Sorry if I woke you,” they said softly without turning around as she stepped up behind him and wrapped her arms around their waist. As she pressed her body to theirs, they could feel that she was still as naked as she had been when he’d left her in bed. Her reply to their apology was a soft shush and series of soft kisses on their neck, shoulders, and back. Toby let out a little gasp when her soft lips found a particularly sensitive spot on their neck and turned around to face her. She had a soft, sleepy, mischievous smile on her face as their eyes met and the next kiss landed on their lips. Her arms went over their shoulders and theirs wrapped around her waist as they shared a long soft kiss.
“Don’t apologize,” she said softly in one of the short moments when their lips were apart. “I wanted to let you have me all to yourself.” Toby gulped a little at the passion and desire in her eyes and her voice. She reached between them as their tongues intertwined and palmed the bulge in their boxer briefs. They wondered why they even bothered to put them on as she stroked their shaft through the thin stretchy fabric. His hand reached lower, too her tight little butt, and when they spread her cheeks a little they could feel the buttplug with its shiny jewel still in her ass from the night before. Toby played with it a little as they made out and they decided how they wanted to use her, since she had made it clear that’s what she wanted when she’d declared her submissive desires the night before.
It didn’t even take a word to get her on her knees, just a bit of gentle pressure on her shoulders. She obediently knelt in front of them as they leaned back against the railing that wrapped around the deck of the boat. With one of her hands between her legs and the other on their leg she started to kiss and lick their cock through the fabric of their underwear, soaking them with saliva in spots before sucking them dry. She spent extra time at the tip, tasting the precum that was already leaking from their cock into the fabric. Toby groaned from the stimulation, the warmth and the soft pressure, and played with her hair as she played with their bulge.
Neither of them were in a hurry and both were enjoying the tease, so it was a few minutes before she began to pull down on the elastic waistband of their boxer briefs. She let it catch on their stiff cock, pulling it down until it finally sprang free to slap against their stomach. They both giggled a little as she pulled their underwear the rest of the way off and tucked it somewhere it wouldn’t blow away. Their eyes met again and this time locked together as she leaned forward, her lips reaching for their cock again. Toby let out a long sigh when the first pressed against the sensitive tip and her tongue reached out to lick in circles around the head. She lickedtheir shaft and brushed her lips over every inch of him, but each time her lips started to wrap around the head of their cock she gave a cute little smirk and pulled her head back to tease him some more.
“Little brat,” they said with a grin when they figured out the game she was playing. She wanted him to make her. She looked up at him with wide eyes full of fake innocence as she continued to tease their dick. The next time she took the tip between her lips their grip on the hair on the back of her head tightened and they pushed her down hard, forcing their cock into her mouth as she tried to pull back. The fingers on her clit sped up as more and more of their length pushed its way between her lips.
The night before had been clarifying for her, and she felt almost none of the shame she so often had when giving in to her submissive desires. She felt free and more herself than ever as she let this boy who she’d known for so long have their way with her mouth out in the open air. The ache of her knees and her throat were more than worth it for the waves of pleasure she felt her fingers stroking her clit and the thrill of being in such a vulnerable and exposed position. It felt like no time before she was on the edge of an orgasm, but with the decision the boys had made that she wasn’t allowed to cum unless both of them agreed, and Billy still asleep, all she could do was edge over and over. She didn’t even really mind though. It would have been nice to cum, but the physical pleasure she still felt, the always ready for more state the denial left her in, and the way it made her feel so useful, like such a good girl, were even better.
…
The boy’s usually wore something while they were underway, Toby with their boxer briefs and Billy in a tight fitting pair of speedos, but Ali seemed to have decided to go naked for as much of the trip as possible. With her relatively flat chest and lack of anything swinging between her legs meant there was little extra risk to her helping to sail the craft nude. With the calm breeze and flat water there really wasn’t that much to do once they were underway anyway. Most of the time Billy took the helm, teaching the other two about sailing as they went and telling them which ropes to pull, and when. There were long stretches of time where nothing was needed besides a steady hand at the helm, so once Toby and Ali got bored of learning the best way to move with the floor at an angle and picking Billy’s brain about sailing they had to find other ways of entertaining themselves.
Billy did his best to keep the boat steady as the ocean passed beneath them, and even though there were a few dips and turns here and there he thought he did a pretty good job considering the two sets of lips making their way up and down the shaft of his cock. He gripped the wheel tight as he strained to keep himself upright and the boat straight while Ali sucked on his balls and Toby licked his shaft from base to tip. The biggest jolt came when Ali took the head of his cock in her mouth and Toby pushed her head down until Billy’s entire cock went down her throat. Toby stared into his eyes then kissed his hard stomach as they held the occasionally struggling girl’s head against his hips. When they finally let her up to breathe, they only gave her a moment before they pushed her down again, this time not quite as hard, moving her head up and down on Billy’s cock. Her eyes were watering a little but full of satisfaction at her ability and how much pleasure she knew she was providing.
They tried their best to make Billy cum while he steered the boat, but with his focus and determination he was able to resist long enough for them to get bored and give up, deciding a naked nap on the large outdoor couch near the helm would be more fun. Billy grinned, both from a joy at winning and from knowing how much better an orgasm he would have later that night due to his ability to resist. He watched and occasionally stroked himself as Toby and Ali cuddled on the sofa gently kissing, touching, and grinding on each other as they napped in the afternoon sun.
Source: reddit.com/r/eroticliterature/comments/10q8551/sail_away_m19f19nb19_bi_oral_anal_threesome_work