Buggered to Bermudabyvoluptuary_manque©
The Wrightsville yacht harbor dipped beneath the horizon off the stern of the big sloop. As its hull neatly parted the waves, the rigging beneath the taut sail hummed while the breeze of the yacht's passage gave relief from the muggy July heat of the North Carolina coast. Brenda watched the coast disappear for a few minutes and then turned to the woman sitting beside her.
"I had no idea the Promiscuous Miss was so big! When you invited us out to sail to Bermuda I have visions of being kind of cramped below decks but this is posh. It must have cost you guys a fortune."
Sally-Ann grinned over her Tom Collins. "With a busy website and a half dozen mall outlets, the Glistening Cucumber has been good to us. And since Hal works so hard at making it go when he suggested we get a boat for when we do have time to relax, I told him to go for it. After all, it's his only real hobby. The rest of his life is the business."
There was a lady-like snort from Sally-Ann's other side. "That's presuming you think having a lingerie and adult toy emporium isn't fun in its own right." Melissa took another pull on her Mojito. "And since this trip is supposed to degenerate into an orgy fairly soon, I'm presuming we'll be testing some new products? So Hal can legitimately write off some of the expenses as a business trip?"
Sally-Ann smiled benignly, "Well, naturally. Glistening Cucumber owns the Promiscuous Miss, after all, and she is listed as a product research lab on the books so of course most of this trip will come off the corporate taxes. I mean, we didn't write the law and if the government doesn't want us taking any advantage, they would change it, right?"
Brenda giggled. She looked down into her glass and was surprised that it was still half full. Her Bobby was in charge of the bar and she suspected he'd made the drinks pretty strong if she was starting to feel silly this soon. "So when do we all get naked?"
Sally-Ann wrinkled her freckled nose and nodded to her right. "Oh, about the time this one has finished her third drink. It takes a while for Melissa to loosen up."
"Hey!" Melissa protested, "It's not easy overcoming the inhibitions twelve years of Catholic school pounded into me. I just consider myself lucky that the nuns didn't convince to shower fully dressed." She held out her glass for a refill as Bobby came by with a tray. He managed to mix her a new one and hand it back without spilling it all over the women's sailing togs before heading off to carry beer to the rest of the group.
Brenda looked down at the tote bag between her knees. Sally-Ann had handed everyone brand new Glistening Cucumber totes when they boarded and now the youngest woman in the group decided to explore the contents. She rummaged through several bottles of skin flavorings, different scents and consistencies of lubricant and from the bottom pulled out a wrapped box. Turning it one way and then the other, she gave it a shake, shrugged and tore off the wrapping to unveil a sky blue leather harness that matched her eyes and an impressive silicone dildo that matched her pale skin.
"Whoa! What's going on here? What am I supposed to do with this? Are you all into girly play? I'm supposed to bugger Bobby? You know he'll never let me do that."
Melissa hiccupped gently. "Will, too. You just wait. Gloria will strip down right in front of him, pull off his pants and give him a full contact lap dance. Then, before he can cum, she'll coax him up onto his hands and knees and introduce him to the delights of prostate massage. While he's cooing and humming over that, our hostess here will strap herself in, grease her bad boy up and before Bobby-boy knows it she'll be fucking him half blue. They ganged up on Gary like that last trip and I got butt-fucked all the way to Bermuda. I'd be sitting quietly and the skipper would ring a bell. I'd have to get up, drop my drawers (if I had any on!) take my tube of KY to the capstan and bend over. Everyone, and I mean everyone would line up and fuck me. Pussy or ass, it was up to them. All I could do was stand there and cum over and over until they'd had enough. Then on the way back it was Gary's turn. Fun? Man!"
Brenda put the box on her lap. "Hang on. Everyone lined up and sodomized Gary? I didn't know he was bi."
Sally-Ann winked. "Except for Marco, I don't think any of the guys here are, at least not very much. But men in prison aren't either, usually. I've never seen any of them kiss each other or give blow jobs but with enough encouragement they'll do each other's butt, at least out here at sea where no one else knows."
Brenda's eyes were like headlights. "I—I never realized. When you said this trip would be wild, I had no idea. Sally, I've never let Bobby fuck me up the ass before. I was always afraid it would hurt. I mean, he's pretty big . . ."
Sally-Ann grinned in response. "Is he, now? That's good news. I mean, I'm not a size queen or anything like that but I do enjoy being well stuffed. You just send him up to the master stateroom some time. Tell him I've got something he'll like."
"Hey, Bobby's in good shape but if this trip is the way you describe, he may need to sleep at night."
Melissa snorted again. "Honey, this boat is full of all kinds of aids. Believe me, the men manage. I not only got sodomized every day but come night time I'd be lying there in the dark knowing some stud was headed my way with a cock full of cum just waiting to shoot his load into my pussy. And I never found out who it was until the first light the next morning. By the time I got home, I had to take another three days vacation time to recover so I didn't walk bow-legged into the office."
Brenda was dumbfounded. "Really? Seven times up the ass and once in the pussy every day for nine days out and nine days back? Wait a minute. How long will we be in Bermuda? Twelve days, no? I mean this trip is a month long isn't it?"
"That's right, but I only got buggered every day to Bermuda, remember? While we were there and on the way home I only got laid two or three times a day, unless you count the latent lesbian, here." She elbowed Sally-Ann.
"Am not," Sally-Ann stuck her tongue out. "I was just filling in the time while my next lover recharged and you jiggle so well when you're getting pounded I couldn't resist. Besides, it got Gary all charged up so he kept on you for two weeks after you got back, you said."
Melissa blushed and hiccupped again. "He did. 'Sa good thing my coil was still workin' or I'd have to skip this trip takin' care of a kid. Way he's talkin' this may be our last. 'Mean, we've got the house, his practice is boomin' . . . 'bout time to start a family, he thinks."
Sally-Ann reached out and gently took the glass from Melissa's hand. "Sounds like you're ready honey. Shall we let the guys know it's time?"
"Yep," Melissa rose and pulled the hoodie off over her head followed by the bikini top underneath. Her soft handfuls bounced gently. She hooked her fingers inside her waistband and shoved Capri's and thong do the deck, revealing a smooth, well-waxed sex. She winked at Brenda. "Well, you wanted to know when to get nekkid. 'S time, time to go strut our stuff and get stuffed."
The other two stripped down. Brenda started to shove her clothes into the tote bag but Sally-Ann stopped her, pulled out the harness set and handed it to her. "You keep this nearby."
They swayed and jiggled back along the deck to the cockpit. Hal had put the computerized yacht on autopilot and he, along with Gary and Marco were watching Gloria slowly peel off her clothing piece by piece, swinging her hips slowly in front of Bobby's goggling eyes.
Melissa bent to Brenda's ear and whispered, "Tolja. You just watch. Won't be long before you're putting that new dong up his chute and he'll thank you for it. Whole new load of fun for you two when you get back."
By now Gloria was naked, her full, voluptuous figure glowing tan in the subtropical sun. "Well? Hyou know you wan' me, macho. Let's see that polla, Bobby, show me hwat you can to with it. I bet you can chinga a chica real good, no?"
She untied the string on his sweatpants, grabbed the legs and pulled it off under his butt and down to his knees. Bobby's cock stood proud at attention. As Brenda had said, he was pretty big. Gloria settled down sideways on Bobby's lap stroking his cock with one hand and his face with the other. The man responded by grabbing her by the buttcheek and boob.
To Brenda's amazement, the scene unveiled just the way Melissa described and it wasn't long before her husband was on his knees and elbows with closed eyes and a contented smile humming and moaning softly while Gloria's gloved fingers worked magic up his butt and all over his prostate gland. With a knowing, self-satisfied smile, Sally-Ann pulled a well-used leather harness from her tote. It was cordovan red and went well with her dark hair. The dildo was big, black and ominous looking as it jutted aggressively from her crotch. Staring lustfully at Bobby's buttocks, she slathered thick lubricant all over the dong and then fastidiously wiped her hands on a rag. She nodded at Gloria who gave Bobby a sharp spank and stepped to one side.
Completely unaware, Bob felt something much larger than Gloria's fingers press on his anus. "Hey!" he exclaimed as the knob pushed through his sphincter muscles.
"Hey, yourself," Sally-Ann growled with a slap on his ass, "Hold still, honey, you'll be surprised how good this feels. Most men just love it." She grasped a hip in each hand and thrust her pelvis forward running the big dildo all the way in.
"Ah?" Bobby's eyes went wide with astonishment. The woman withdrew slowly and then thrust again bringing an appreciative moan. As she began to pump in and out her lover's eyes closed and his jaw went slack. Underneath him Gloria kept up an expert hand job making sure he was hard and fully rampant. Then she whipped out a silicone cock ring, stretched wide and slipped it over his package, clear down at the base.
"There now, macho, you gon' stay nice an' hard while we make you feel sooo good. Then when I'm done wit' you, you do me up the culo like I done you. Make me squeal, no?"
Melissa reached for Brenda's harness box with a mischievous grin. She pulled out the flaps and removed the big, peach-colored dildo. Brenda blinked at the odd shape.
"Here," Melissa chuckled and reached for a tube of wintergreen lubricant, "you put this big, fat end inside. That way when you push it catches your clit and G-spot and feels as good to you as it does to him. If you've got good enough muscle control you won't even need the harness. I keep mine in the nightstand so I can surprise Gary with it. Go on, put it in."
Blushing slightly, Brenda did as commanded. The cool wintergreen inside her snatch made her inhale. "Ooo, that feels good!" She strapped the harness over it and adjusted the straps while Melissa coated the business end with a bottle marked Sexy Heat.
Just as she finished Sally-Ann chirped and moaned and then pulled out. She leaned down next to Bobby's ear. "Don't you move, now, we're not done with you yet, not even a little bit."
Melissa put a hand on Brenda's naked butt and gave her a push toward her husband. "Go get him, girl; peg 'im a good one."
Unsure of herself but game to try, Brenda stood behind her bent over man and put the tip of her dong on his glistening brown star. Copying Sally-Ann's technique she grasped each of Bobby's hips in a hand and pushed forward. The dildo went in half way but the squeeze on her own parts was a bit of a shock. Maybe this could be fun.
Gloria stood next to her, her own black harness and purple phallus at the ready. "Use hyou back, honey. Hyou got to learn to fuck like a guy. Do him just opposite the way when he fuck you. Si, tha'ss better. Ride him, chica."
As she began to get the idea, Brenda looked up and saw Sally-Ann lay face down on a mat, spread her thighs and arch her back. Turning her head to one side with a smile she asked, "Well, who's first?"
Marco knelt between her legs, a big squeeze bottle in one hand. He squirted oil all over her buttocks and rubbed it around before laying his stiff cock between her ass cheeks and sliding up and down. Sally-Ann lifted her butt in time with him for a while until he paused briefly, put the helmet against her anus and took her hard. She gasped and then grinned. "Fuck me, Marco," she growled. Leaning down on his elbows, the man took a generous globe in each hand and with a slow, measured rhythm pounded against her ass.
Brenda was now in the groove. Not only did it just feel good but the sensations of power were amazing. Suddenly she was gripped by a set of unstoppable contractions that made her scream and left her breathless. She pulled away and stood still for a minute, blinking. Orgasms were nothing new but this one was different, one that she wanted to experience again.
Hal took her hand. "You just come on over here and kneel down next to Sally-Ann, Brenda. No, leave the harness on, it's sexy and it's your turn."
"B—be careful. I've never been buggered before. Don't hurt me?"
"Not a chance, pretty thing. I'll be real careful with you. We don't want you deciding you don't ever want to get it like that again."
Dropping to her knees, Brenda put her chest on the mat, turned her face to one side and closed her eyes. Warm oil dripped onto her ass like cake frosting and Hal rubbed it all over, taking particular care with her perineum and anus. Brenda trembled a little. To her surprise, instead of tickling as she expected it felt good, really good. Then a blunt shape pushed gently on her star and began to buzz. The frequency was slow and to her amazement her sphincter muscles relaxed. The thick vibrator slowly entered, past the first sphincters and then through the second. The vibrations radiated through her body reaching her G-spot and clit. She took a deep breath and let it out in a long, soft moan.
"Ah," Hal chuckled, "Like that, do you? Good, because I'm gonna like what comes next."
The vibrator slipped away to be replaced by the head of Hal's stiff cock. He pushed. She gasped. He held still for a few moments and then started a series of short thrusts. With each one Brenda squeaked but she pushed back against him. Soon he was hilt-deep in her ass.
"Now, girl, this is what you're here for. You're the new one so you get the complete treatment, buggered all the way to Bermuda. Just. Like. This!"
His pelvis slapped against her buttocks as the rest of the crew cheered. Even Sally-Ann and Bobby, who were getting the same treatment whistled and hooted as Hal took Brenda through the squeaks to the whimpers to the moans, loud cries and finally to a scream as the most powerful orgasm of her life wracked her again and again and she collapsed, panting.
Brenda looked around. Sally-Ann had a very satisfied expression and Marco was cleaning off. Gary had tied his wife's wrists to the railing and was sodomizing her enthusiastically just as Gloria pushed Bobby onto his back, straddled him and then sat hard on his manhood. As she predicted, the Cuban let out a squeal. "Macho, tan grande eres! Hyou stretch me, Bobby, hyou stretch me big time. Do it feel good when I do this? She rotated her hips and bounced up and down. Apparently it did.
The clear, Gulf Stream night was a riot of stars. But with no moon coming in through a porthole, Brenda's stateroom was so dark she couldn't see her hands. She shivered. Each woman had stuck her hand into a bowl and pulled out the number of a stateroom. When they were gone, the men had done the same but waited a while before following. Brenda figured it was to let her apprehension/anticipation build. Who would it be tonight? Or tomorrow night? There were only four men and eight nights to Bermuda. Sooner or later Bobby would be in bed with her but this time she was sure he wouldn't take, "No!" for an answer when he reached for the tube of thick lubricant. Buggered all the way to Bermuda! And it won't be just the guys, either. Melissa and Sally-Ann weren't kidding, I bet. Hot cocks and bright dongs, I'm going to be so used.
A faint whisper of logic suggested that everyone was getting used. She wasn't really getting any more shared than the other women or, for that matter, than the men. But it didn't feel like that, down deep in her primal brain. Her man was letting his woman be the buttered bun in a sort of orgiastic bonding ritual with the other men, that's what it felt like, and how did she feel? Kind of—of resigned, resigned and compliant. That's what he wants from me. And I'm giving it. Not that I have a lot of choice. I mean this boat is seventy-one feet long and while that's big it's not big enough to get away from anyone. --And—and the strange thing is I don't want to get away. There's no place I'd rather be now than here and no time I'd rather be here than now. Lassitude spread out from her groin as she heard the cabin door open. Someone was coming for her.
A warm man-smelling body got up on the bunk with her and on her. As his lips pressed against hers and his tongue drove into her mouth, Brenda raised her arms and wrapped them around his neck. He stroked her face and ran his hand down her side to her hip, reached under and fondled her backside. With a quiet little murmur she went limply soft and willing.
"So, how do you want me tonight, lover?" Brenda whispered when her mouth was finally free of his burning kiss, "I've got lots of ways to make you feel good. Which one do you want to start with?"
The response was a wordless chuckle. The man began to kiss his way down her body starting with her earlobes and then working his way down her neck. He spent a goodly while on her nipples and aureoles, sucking and nibbling and then back and forth across her belly. She clutched his head with desperate hands when he reached her sex and started long, wiggling licks from the back of her labia to the clitoris and back again. After he had done this long enough to make her moan his tongue returned to her clit and began a vibrating dance. Brenda gasped. She would climax soon, she knew. What would he do then? Would he make her cum again and again until she begged for mercy and told him to do whatever he wanted? Was this how the other women became such willing catamites, how they surrendered their asses for the men's' pleasure?
The man smiled in the dark as he felt her tensing under his torment. She was hot now but she had no idea how hot he could make her. Before Brenda could climax the man pulled back, grasped her by the hip and rolled her over face down. She was about to protest when he spread her buttocks apart and began to run the tip of his tongue from her pussy back along her perineum and then round and round her anus. If she was hot and ready before, her desire was now a crying need. Oh please, fuck me, finger me, do something so I can cum! I can't stand much more of this. Please?
Finally he stopped the 'torture' and she felt the bunk bounce slightly as he climbed between her knees. She heard the pop of a plastic bottle opening and then felt the warmth of the Hot Lube dribbling all over her butt. A blunt mass pressed on her brown star. Well, of course. That's why he spent so much time driving me mad; he wants my ass, just like Hal did. There's no question, now. Buggered to Bermuda, that's what I'm getting. I'm the new girl and that's what I get. The strange thing is, I want it!
Brenda's needy body surrendered completely. The hot, stiff phallus drove deep into her compliant backside. Unconsciously she lifted her hips in response, pushing back to help him. Now the plundering began. In a slow march rhythm her anonymous lover thrust and withdrew, grunting with effort. Keeping time with him, Brenda moaned softly, breathily and whimpered. They sweated in the humid heat of the cabin, sweated in streams that ran down her sides and soaked the sheets beneath. It seemed as though dawn would come before he finally finished but at last with a groan and his own set of spasms and contractions the man was done. He rolled off and lay panting next to her.