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Cruising Four-Way

Category: Group Sex
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Part 1

My friend Jeff won a one-week trip of the Caribbean on a cruise line for 2 couples, including a 2 bedroom suite. He called me up and said that his girlfriend Rebecca couldn’t go but did my wife Colette and I want to come along anyway? I checked and her work schedule wouldn’t allow her to go so I suggested we invite our friend Scott too and make it a guys only scuba diving trip.

It was all set and the three of us were looking forward to the day when we’d go to Miami and board the boat. If you’ve seen my BDSM submission, “Blindfolded & Humiliated”, you’d know that the five of us have formed our own little group sex gang.

Rebecca and Colette know us too well and told us to take along our latest STD test results with us and not fool around with anyone who didn’t have their results with them too.

We boarded the boat on a Saturday and checked into our suite. One bedroom had two double beds and the other had a king bed. We changed into bathing suits, t-shirts and sandals and went up to the pool deck to see what women were onboard; single, MILF or freak. We didn’t see too many single women and none of them were attractive. The rest of the women seemed to be with husbands and children. So we bought drinks and watched Miami slide by as we headed out to sea.

We were hanging about in the pool and getting hammered. As the ship headed south, Scott nudged me and pointed out a really hot tall blonde with a large fake rack, nice abs and long legs. Her bikini top was skimpy and too small, allowing lots of sidewall to peek out. But instead of a thong, she was wearing a high-cut tankini bottom that showed her firm buttcheeks perfectly. She also had a pierced belly button and I could clearly see through her top that her nipples were pierced too. Jeff beat us all out and walked up to her, handing her a drink. She introduced herself as Lisa. Scott and I turned away as they made small talk so that we wouldn’t fuck up Jeff’s chances.

After a 1/2 hour and more beers, Scott & I could tell that Jeff was making headway with Lisa. She was rubbing her hand along his forearm and laughing at Jeff’s BS, showing off her pierced tongue. As they left the pool deck and headed up towards the ships’ nude sunbathing deck, Jeff looked back at us with a grin on his face. Scott told me he hoped she turned out to be a freak so that all three of us could bang her in a four-way. We chatted up a few late-arriving ladies but none seemed keen on talking to a pair of white and black buddies. A few minutes later, Jeff came running back, grabbed more drinks and told us to follow him because Lisa had already given him a blowjob and wanted to suck us off too!

We got up to the secluded sundeck, rounded the corner to find Lisa slobbering all over Jeff’s fat dick. She was topless with her hot ass peeking out of her bottoms and her tiny tan lines gave me instant wood. She left Jeff and came over to me, pulling my suit down enough for my meat to flop out at her. She told Jeff and Scott to watch and keep an eye out for others coming up the stairs. She sucked it into her mouth with a lot of spit then turned me around to bend me over and toss my salad. Damn, this woman was all freak! She made an Ooh! sound when she found that my ass was already receptive due to Colette’s training it with sex-toys. As her moist tongue pushed its way in, it almost felt like I was taking a shit in reverse. Lisa flipped me around again, shoved three fingers up my ass, pressing on my prostate hard and had me squirting down her throat in less than two minutes. She was a world class cocksucker.

Lisa pushed me away and ordered Scott over. She made some cooing sounds when she saw Scott’s long black monster. He’s even thicker than Jeff and I are, with a coke-can thick 10 incher but his head is smaller compared to Jeff’s 7 incher and my 8 incher. Lisa had about half of Scott’s crank down her stuffed throat when she suddenly gagged, bent over and threw up a little. He mascara was running down her face as she gasped for air. Jeff used a towel to clean up and Lisa grabbed Scott’s meatpole and sucked her cheeks in really hard, putting a lot of suction on it as her hand flew up and down his shaft and her other hand was probing between his buttcheeks. Scott tensed up after only a minute of this and blasted a thick, creamy load into her gaping mouth. Whew! Scott and I headed back to the pool bar but saw Lisa & Jeff walk downstairs towards the cabin a little while later.

As Scott & I headed back to our suite to get changed for dinner, we were wondering how Jeff had done with Lisa. We got our answer when we opened up the door, walked into the salon and saw Jeff & Lisa on the couch. Actually, Jeff was kneeling on the floor with his upper body laying on the couch getting boned up the ass bareback by Lisa’s very real and very large cock! Holy crap, Lisa was a she-male. They glanced at us but didn’t slow down one bit. Lisa was really slamming her hips into Jeff’s backside, making that hot meaty slapping sound we all love to hear. I couldn’t believe he was taking all that meat that hard. Ever since Colette started using ever-larger strap-on’s on me while we’re playing out dominant sex games, I’d begun to have secret fantasies of doing it with a tranny. Here was my chance.

In our scenes, Jeff and I both had been getting a steady diet of Colette’s strap-ons and he blurted out “Mike, it’s like getting fucked with a meat strap-on!” Scott asked Lisa if we could get in on the action and she said the more the merrier. I was amazed at her appearance. Other than her cock and balls, she looked every bit a woman. She was hairless all over, her ass was round and firm, her hips flared out from a tiny waist and she was gorgeous. Scott and I both stripped down all the way and walked over to the lucky couple. I grabbed some of the lubricant that was laying out on the table while Scott straddled Jeff’s waist and stuck his long, black cock in Lisa’s face. I had Lisa stop for a second so I could lube her up and get her ready for my girthy dick. This time, she had managed to get Scott’s lengthy cock down her throat and I leaned around her to see that she had her tongue out licking his balls. She was drooling spit and making all kinds of sexy choking sounds.

I nestled up behind her and lined my fat cockhead with her soaking wet asshole and began pressing in. It slipped out of alignment a couple times until Lisa finally grunted and pushed her asshole open, allowing me to get the head in. Lisa had a sharp intake of breath and her anus clamped down on me but I held onto what I had and didn’t let it slip out. We’d got our wish, we were having a FREAKY four-way! Scott was getting a blowjob, I was getting my dick squeezed by Lisa’s tight starfish, Jeff was getting fucked hard by a meat strap-on and Lisa was getting spit-roasted at each end while her cock was buried deep in man-ass. Totally fuckin’ hot scene.

I eased my fatty into Lisa’s asshole the rest of the way. As I bottomed out I could feel that she hadn’t cleaned herself out adequately but that didn’t stop me. I knew from personal experience that it would just get softened and churned up by my pistoning cock, allowing me to penetrate further. Since the whole scene was so hot, none of us lasted long before we started cumming one by one. First was Scott, roughly holding Lisa’s head against his belly as he squirted come down Lisa’s gagging throat. Next was Jeff. He and I had been slamming our hips at Lisa while she remained motionless to help prevent my dick or her dick from slipping out. I knew Jeff was really close because his muscular frame swells up just before he comes. He was wearing a condom to save his come and he filled it up while grunting and sweating through his orgasm. I took that as my cue to grab Lisa by the hips, push her forward all the way into Jeff’s loosened ass and went into a back and forth blur of sweaty, pumping meat. Lisa’s anus tightened on me in a rythmic pulsing fashion so I knew she was squirting her load deep into Jeff’s ass as she grunted and swallowed Scott. That’s all it took to set me off as my cock swelled up even more and blasted a hot load of goo into the mess lodged deep inside Lisa’s bowels.

There was total silence other than gasping and panting as we all gained our breath back for a few minutes. Then Scott unstraddled Jeff and went to the mini-bar to get us all beers. Jeff eased forward until he was sure he wasn’t going to have a mess and I felt my cock softening inside Lisa’s fudge-packed ass. I asked Lisa if she was worried about making a mess and she said yeah, we’d better go into the bathroom and pull out over the tub. She’s a big girl at 5’8″ and 130 lbs but Scott and Jeff helped me pick her up and carry her into the bathroom. Lisa leaned against the wall with the hot shower aimed at her ass, telling us the best sex is always a little messy. As my fat cockhead plopped out of her ass with a loud wet fart, she messed herself a little before she could get her anus dilated shut. She moved over to sit on the john while Scott and I soaped up and cleaned our dicks over the sinks. Jeff had walked over to Lisa and had her remove the condom, sucking down his load and cleaning his dick with her mouth.

Part 2

The four of us got cleaned up, Lisa went to her cabin to get dolled up and the three of us changed into sport coats and slacks for dinner. The four of us went into dinner together and had a great time, laughing and getting to know Lisa better. Afterwards, we all went dancing in the bar, taking turns grinding our cocks into Lisa’s ass and crotch. We got a booth and discussed what we’d do the rest of the week. Lisa proposed that we set up a sex schedule. She took charge and said in the evenings all three of us would fuck the hell out of her in whatever manner our filthy minds could dream up. In the afternoons, she would take one of us to the cabin for more intimate one on one sex. Lisa pointed out that Saturday was already shot and the next Saturday wouldn’t allow us any time for sex because we’d make port and be off the ship early. That meant that each guy would get to be intimate with her on two afternoons through the week. But in the mornings she suggested that each guy also be the “focus of attention” twice in that week, with Lisa and the other two guys gangbanging him. Six days of non-stop sex, morning , afternoon and night.

Scott, Jeff and I were stunned silent for almost a minute while Lisa looked at us with half-lidded eyes. She said she was our mistress for the week and if we didn’t agree to the schedule she would have no problem hooking up with other guys on the ship. All three of us quickly agreed to our new mistress’s demands. The three of us drew our names out of Scott’s panama hat for the morning and afternoon sex sessions. It was me, Scott, then Jeff for the afternoons and Scott, Jeff, then me for the morning orgies. Perfect.

We danced a little more and went back to the cabin early. Lisa stopped off at her cabin on the way back and brought her entire bag of sex toys.

We all stripped down naked as soon as we stepped inside our suite, but Lisa had on a stunning mylar push-up bra with most of her tits hanging out again, followed by a mylar garter, fishnet stockings and platform fuck shoes. She’d gone commando the whole night! She lined us all up, kneeling on the rug and told us that whoever did the best job sucking her cock could get her ass. She walked up to me, thrust her hips forward so that her cockhead was rubbing against my face. I glanced sideways at Jeff and could see that the scene was turning him on. His cock was bonehard with the veins throbbing. I opened my mouth as wide as I could and tried to remember what I liked best about deepthroating and tried to do the same to Lisa. The only problem is, as I began sucking on her cock I realized it was even longer than Scott’s! She wasn’t as thick as Scott, about the same as Jeff and me. But she had to be at least an inch longer than Scott’s 10 incher.

I grabbed her balls with my left hand and the base of her shaft with my right as I sucked on the head. I started talking dirty to her. “Do you like doing it with girls as well as guys?” She replied yes. “Do you want me to suck it slow & sexy or hard & slutty?” She said slutty. “When you do it with girls, what’s your favorite thing?” She told me she liked to push the girl on her back, move her legs behind her ears and fuck the girl’s cunt hard while they rubbed their tits together. That got me so turned on I began sucking her hard and trying to swallow her. But every time I got her thick, spongy cockhead at the back of my mouth I’d gag hard and have to stop to keep from throwing up. Lisa must have liked the sounds I was making because he cock was steel hard. I was surprised a dick that big could be that hard.

But she stopped me after 5 minutes and went to Jeff. Jeff was able to deepthroat her with ease. When he saw me and Scott looking at him with shock, he said Rebecca had been making him suck and deepthroat her strap-ons. Lisa almost came after only two minutes so she went to Scott and placed her pink cock in his face. He eagerly began licking the head, slobbering it with lots of spit. Then he bent his head forward and gagged about 3/4 of her meat down his throat. He came back up gasping for air and then repeated his motions, reaching between her legs to push his fingers into her ass. He turned her around and mashed his face between her buttcheeks tossing her salad with loud slurpy sounds. Lisa was moaning loudly when she turned around and jammed her meat deep into Scotts mouth and came hard. Looks like it was Scott who was going to get her ass but how he was going to get that club of his all the way up her anus I had no idea.

We all moved to the king-size bed. Lisa had Scott lay down on the bed facing up. She told me that since I’d had her ass earlier that day that it was only fair she was going to have my ass now. Scott began using his fingers to lube up her ass with gobs of Astroglide jelly until it was gaping a little and shiny with grease. Her cock was halfway back to hard when I laid down and began licking her. Jeff had gotten the digital camera out and was taking closeups. She placed herself over Scott in the reverse cowgirl position, having me hold Scott’s cock in place while she slowly squatted down on his monster. As his cockhead began indenting her asshole, she started to wriggle her hips side to side. She said it helped easing a big object into a tight ass and helped reduce any discomfort. She squatted there wriggling for a good couple of minutes and then it seemed her asshole dilated and Scott’s pointy cockhead wedged in. Lisa let out a gasp and began posting up and down by an inch. She wriggled her hips some more and took in another 4 inches. Her cock was leaking copious gobs of pre-cum that I kept licking off her tip. Jeff had stood up on the bed and Lisa was idly sucking his cock as she concentrated on getting Scott’s meatpole up her tight ass.

Lisa had about 8 inches of black cockmeat in her violated ass when she stopped moving down. I asked her what was wrong and she replied that it had reached her sigmoid sphincter where the colon narrows down. It would take more wriggling and jiggling to train her sigmoid to open up and allow such a wide invader deep into her bowels. I was asking myself how the hell I was going to get her even longer dick into my intestines when she must’ve read my mind and said it wasn’t so much the length once it was past the sigmoid, it was the thickness that made it difficult. I renewed sucking her cock and was making really nasty slurping sounds when she finally sighed and sat down on Scott the rest of the way. Damn, she looked hot sitting there with 10 inches of thick black sausage thrust deep into her belly and her cock was throbbing up and down as her heart beat. I immediately turned around on my knees, leaned forward until my head & shoulder were flat against the bed and scooted backwards until I felt her wide cockhead wedge into my buttcrack.

While Lisa grabbed the tube of Astroglide jelly, she kept her ass flat against Scotts belly while doing a stirring motion with her hips to keep him hard and deep. Lisa had her right and left hands’ middle and index fingers in my ass, slowly dilating and pulling my ass apart and open. She told me to ease back. I did until I felt her wide head nudged up against my gaping anus. She told me to slowly but steadily keep pressure on her dick but to wiggle my hips back & forth a little like she did to ease it’s passage. I’d been getting trained by Colette for months now and some of her vibrators were even thicker than Lisa’s cock. Colette’s purple Emperor was about the thickest that I could handle. I had found that once I had the head’s wide part past my sphincter, the rest was easy. I was following Lisa’s directions when she told Jeff to kneel down and shove his cock into my mouth. I know it’s mental gymnastics on my part but so far I didn’t mind the freaky stuff with Lisa because that was just sex with a chick who happened to have a dick. But Jeff’s male dick thrusting in my mouth got my mind off things at my other end and next thing I knew Lisa had 8 inches of her cock deep in my ass before it nudged up against my sigmoid colon.

At that point, Lisa started posting up and down on Scott’s mammoth meat about four inches at a time while holding onto me. I remained steady while Lisa plunged in and out of my ass and Jeff thrust his fat cock into my mouth until he had it wedged down my throat and I was drooling spit and slobber all over his balls. Once again, none of us lasted too long and all of us came within less than a minute of each other. I could feel Lisa’s cock swell up and get harder as her breath became ragged and husky. Jeff’s cock swelled up too as did his well-defined muscles. Lisa came first with her cockhead wedged hard against my sigmoid and I could feel every pulse, every squirt of her sperm against my colon, making me spurt my cum all over my thighs. I was moaning my lust into Jeff’s crotch with my nose jammed hard against his belly when he thrust hard into my mouth and held it there as he spasmed his jizz down my throat. I swallowed hard to rub his cockhead like Colette does to me and he spasmed one more time before pulling out and wiping his cock on my lips.

My moaning and gulping set Scott off because I could feel the bed jiggle as he pumped a big load deep into Lisa’s intestines.

We stayed like that panting, until Lisa spoke up and said everyone remain where they were and to slowly begin having more of the same sex in the same position. By this time, my prostate was hurting, but in a good way. I’d come that afternoon on the pooldeck from Lisa’s BJ, come later on with my dick stuffed up her ass and now had spewed a big load all over my sticky thighs. But I knew I had one more in me because the whole situation was so mind-blowing and hot. Jeff got up and pushed his crank into Lisa’s face again, her jaw opening wide like an anaconda to swallow him. While Lisa’s cock never went completely soft it did soften a little bit, enough that I was able to wriggle my ass back onto the remainder of her shaft, with her balls squished against mine. That was all it took to get me completely hard again. I began pistoning my ass back and forth along her shaft and my ass could feel her cock gradually get harder. But soon she was hard enough and long enough that when I bottomed out her spongy head was jammed hard up against my sigmoid colon. My ass was feeling completely stuffed and filled but I knew soon it would become too painful if I kept trying to get her lengthening girl-meat past my sigmoid.

Lisa solved the problem for me by stopping me and wriggling her hips as she steadily kept deep pressure on my sigmoid with her prick’s plum-shaped head. And then I felt it; her cockhead had slipped a couple inches further into my rectum, past my sigmoid. I grunted very loudly and came right there. Lisa grabbed my hips and pulled me the rest of the way onto her lap. She was sitting completely skewered by Scott’s wide meat and I was totally splayed out, arms and legs up in the air with only my asscheeks squished firmly against the base of her stiff pole, when Lisa shot her second blast of cum into my meat-packed bowels. At this point, Jeff pulled out of her mouth, turned around and backed his ass up so Lisa could suck his cock from behind while he bent forward over me and vacuum-sucked the residue of cum from my cock. Scott was loudly grunting the arrival of another load of cum in Lisa’s belly.

We all got our wind back, stumbled into the bathroom and cleaned up. Lisa and Jeff went back into the master bedroom and slept while Scott and I retired to the other rooms. We were talking and laughing about how the girls would never believe this unless they saw it for themselves.

Part 3

The next morning saw Scott and I getting woken up, me by Jeff sucking my cock and Scott by Lisa sucking his cock. We proceeded to have our morning orgy, complete with orange juice and champagne mimosas. Scott was on deck as that morning’s star attraction. We did a quickie where Lisa backed her ass up onto Scott’s meatpole while Jeff fucked him in the ass and I got a sloppy blowjob.

After we’d gone up to the pooldeck, nude sunbathed on the upper deck and had lunch, Lisa and I went back to the stateroom to snuggle. Once we got there, she put on her fuck-me platforms and stood face to face with me as we slow danced and french-kissed. She began working her down to my happy place when she asked me what my fantasy was. I told her I wanted to tie her up. She got out these cool straps from her bag and allowed me to tie her up so that she was facedown with her head towards the headboard. I stacked a bunch of pillows up, sat on them, grabbed her head and fucked my fat meat down her throat. She was making all these hot moaning sounds complete with little squeaks and slurps as her spit ran down my balls onto the sheets. I took her largest vibrating buttplug out of her bag and eased it into my anus and then I turned the dial to the max. She began bobbing her head up and down on my thick cock, with her lips stretched and wrinkled at the corners from the girth of my manhood. Just as I began to swell up prior to cumming, I jammed my cock all the way into her mouth and told her to stick her tongue out and lick my balls. I came as if I’d been electrocuted, spasming and twitching my cum down her gullet.

She licked my cock as it softened and then I untied her, kissing her gently. We laid side by side and as her feather-soft touch revived my manhood, she asked me what I wanted to do next. I rolled onto my back and lifted my ass & legs up. She got a wicked grin on her face. Lisa leaned down, removed the buttplug and began tonguing my ass, squishing her tongue deep into my ass like she’d done the day before, her face mashed between my cheeks. She got me really wet back there. Then she got up and filled a small anal enema bulb with sexlube and squirted the entire thing into me. My dick was raging hard by then in anticipation. Lisa squatted down and nudged her long, thick meat between my asscheeks until it came into contact with my clenched anus. She told me to push as if I was trying to take a shit. I did and she was able to wriggle her hips a bit and get the head of her meat plugged into my anus, just past the sphincter. This time I felt no discomfort, only a pleasurable feeling of being totally fucking stuffed full of warm, throbbing cockmeat. I made a loud grunt, UNH! to let Lisa know it felt good. She was leaning over me, looking intently into my eyes as she squished another 6 inches into me before her glans wedged up against my sigmoid.

She started talking dirty and said this time, no distractions, I’m going to get the rest of this fucker up your belly before I let you come again. She kept leaning into me, keeping pressure on my sigmoid as she samba’ed her ass back and forth to minimize the discomfort deep in my bowels. I could feel the sigmoid loosening up and all of a sudden the head bludgeoned its way in, widening my sigmoid so that the rest of her dick could squish its way deep into my ass, violating my bowels to my very core. I estimated that her dickhead was above my belly button inside me! UHHH! She leaned forward and deeply french kissed me, still wiggling her hips. She said lets give it another minute or two and then I’m going to literally fuck the shit out of you, we’re going to dirty up the sheets. UNH! She got back up and planted her arms on either side of my head and began slowly thrusting her hips against my ass. As she pulled out I could feel the strangest sensation of suction as her bowel-filling meat pushed and pulled on the wall of my intestines. OOHHH! My dick was rock fucking hard, veins swollen and throbbing. Lisa leaned over and grabbed the camera off the nightstand and took numerous pictures. Zoomed in on her cock stretching my anus wide, zoomed out for a wide angle POV shot, zoomed in on my straining cock & balls, you name it.

Lisa put the camera down and began picking up the speed, fucking me for real now. I had my hands on her tits, squeezing them hard as I supported her weight by hooking my feet into her armpits. She really began buttslamming me now, her hips spanking my ass with that meaty smacking sound. UNNHH! My cock began to swell, she began to swell up and she started longstroking her cock in my ass, pulling all the way out leaving my anus gaping wide then plunging back in until her balls were squished up in my asscrack. It was the feeling of that, her balls jammed into my asscrack, that set off my explosion of an orgasm. She pulled out a little bit, hoisted my hips a little, leaned down and sucked the most intense load of my life out from deep within the base of my cock. Then her orgasm was upon her and she threw her hips at me in a frenzy, my bowels totally loosened as she oozed her goo deep inside of me. My sigmoid is so much more sensitive than the rest of my rectum and I could feel every squirt and every twitch, prolonging my orgasm too.

Two days later on Tuesday was my turn for being the center of attention from Lisa, Scott and Jeff. My prostate was really killing me by then from all the daily nonstop sex. Shooting 3-4 loads a day was taking its toll and I wasn’t in my 20’s any longer. I had Lisa get on her back with her feet on my shoulders so I could fudgepack her bowels real good. This would fulfill a really freaky fantasy of mine. Then, Scott got behind me and eased his fat monster into my ass. By then, ,my ass was so pliable I was able to take Lisa’s skinny arm all the way up my ass to her elbow. So Scott’s dick was little trouble at all. Then I had Jeff squat on Lisa’s face, facing me so that she was tossing his salad and I could suck his manmeat. We got a nice rythm going. I was moaning and slobbering on Jeff’s fat dick with his thick head rubbing my throat as he thrust in and out. I could tell that Lisa had her tongue wedged deep inside his ass as far as her tongue could go. Scott was really pounding hard into me, fucking me as hard as he could. I was so over-stimulated that I just started coming and never really stopped for about five minutes. It just sort of drooled out of my pee-slit in one continuous orgasm. Lisa’s anus started twitching and clamping down on the head of my penis, signaling that her orgasm was seconds away. I glanced down around the wide pole stuffed in my mouth, pulsing its load down my throat and saw Lisa spurt onto her belly. My anus’s twitching set Scott off. He’d a saved a big load up by skipping an orgasm the night before and I could really feel it’s warm goo coating and spurting against the tightly packed walls of my bowels. I felt Scott’s warm breath against the back of my neck as he grunted through his orgasm, pinning me tight, OOHHH! UNNNHH! AAWWWW!

The best part of the whole trip is that Lisa moved south to move in with Scott. They’ve been together now for six months. The six of us get together almost every weekend since we all live within ten miles of each other. Our scenes are pretty wild. Sometimes the three girls will get together and lez out while us three studs have a manly three-way. This is the basis for another article but the best of all was when Rebecca had her birthday. She had Jeff and me lie on our backs and scoot our asses together, joining our asses together with an 18″ doubleheaded dildo. Then she squatted down on our cocks, taking both into her pussy at the same time. Then she had Scott ram his impossibly wide manmeat down her throat until she was gagging and coughing. She topped it off by having Lisa shove her long, thick cock up her asshole while Colette was piston-fucking Scott’s ass with a strap-on. Colette was sporting a dildo as big as Lisa’s cock. Rebecca said she loved feeling a real cock in her ass while feeling big firm tits rubbing against her back at the same time. Smokin’!

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