Copyright 2006 Herb Cat. Do not reproduce or distribute this story without the author's permission.
Please note: this story depicts oral and anal sex between males. If any of these offend you or are illegal to publish in your jurisdiction, or you are under the age of 18, read no further.
The characters, locations and incidents in this story are fictional. Any resemblance to actual events or locales, or persons, living or dead, is entirely coincidental.
As an author, I welcome feedback on my writing. Please send any comments about this story, positive or negative, to Herb_Cat@mailcity.com. Thank you.
The Pillage and Plunder Cruise
R I C K, I wrote in big block letters on the self stick name label. I was careful to center the name and not to smudge the felt pen. "Hello, My name is RICK." There, that looks pretty good. Then I thought there could be other Ricks on board, and I quickly squeezed a B period in at the end. Immediately I regretted the addition. How stupid, I thought to myself. Now the nametag looks asinine and so what if there's another Rick. Anyone talking to me on this cruise will call me Rick, not Rick B.
I handed the Magic Marker back to the young bare chested stud seated behind the registration table. Man, did I once have pecs like that? Probably not, and what muscles I ever had haven't been visible in decades. I pushed the nametag into the plastic holder, slid the rainbow colored cord around my neck, and sidled up to the next position. Pec boy's partner was a blonde wearing a white T and a sailor hat. He handed me an information packet and souvenir bag and welcomed me aboard again.
I knew it was too late now. I was on board, but I was having tons of misgivings about my decision to sign on for this "Pillage and Plunder" Cruise. All around me were studs in their twenties, laughing, slapping each other on the back, already knowing they were going to enjoy themselves for the next four days. Oh, maybe a few were over thirty, and probably someone on board will be over forty. But here I was, a widower in my sixties. What the hell was I doing here?
A steward had my suitcase and was leading me down halls and stairways to my state room. I kept thinking to myself, I gotta tip this guy. How much do you tip a steward? Did the fine print say that gratuities were included in the price? I don't remember. Damn! He was in uniform. He was an employee of the cruise ship, not like the guys at the table who were from Pride Tampa Bay, the group that organizes the annual P&P cruise. The crew must have known this was a gay group that chartered his ship. Were the stewards gay too? This guy did have a nice tight ass inside those white uniform pants. Most of the trip to the state room, I was behind him so I got a good look at his ass. It was only briefly in the elevator that I stood beside him and was able to read his name badge (Mark). Was Mark looking at me? Was he wondering what an old fart like me was doing here?
We got to the room and Mark opened the door for me, showed me the head, pulled back the curtains over the porthole, and put my suitcase on the rack. "Shall I unpack for you, Sir?"
"Oh, no, thank you," I muttered as I looked out the porthole on to the dock. I was glad I paid extra for an outside room. I didn't know but what I might be spending the whole four days in my room, and at least now I could look out the window.
"You're the first one here, so you have your choice of bunks." I looked around and saw two beds. But of course; I had signed up for a double. I didn't want to waste money on a single. But now the reality hit me. I was going to have a roommate. Double damn. What did I get myself into?
"If you tell me which one you choose, I'll turn it down for you, Sir."
"Oh, no, uh, Mark. That's OK." I realized then he was stalling. I fumbled in my wallet and pulled out a five and pressed it into his hand. "Thanks for all your help. I can take it from here."
"Thank you, Sir." He grinned happily and I hope honestly. I had no idea if that was an appropriate tip or not. My late wife always knew the appropriate tip to give anyone.
After Mark left, I thumbed through the information packet and saw I had two hours before the first event, an orientation. I decided to unpack my clothes and then try to familiarize myself with the ship.
I discovered where the dining rooms were, the pool (there were already a dozen young lads in speedos), the weight room, the sauna, and the ball room. I found the deck marked "clothing optional," and there were already three naked hunks sprawled on deck chairs. I came around the corner and found myself back by the registration table. Pec Boy and Sailor Hat were still welcoming guests aboard. The guests were still as young as before. More couples were arriving now, though. Guys who welcomed this opportunity to hold each other tight, to kiss in public. I played a mental game, trying to decide which guy in each pair was the top and which the bottom. Of course, I knew that often mates don't have strictly defined roles but I enjoyed the mental challenge.
I heard Mark's voice and caught a glance of his white ass disappearing down the deck followed by an older gentleman. He was wearing a tan jacket, bermuda shorts and white sox that extended up his shins. From my vantage point, he must have been at least forty, which gave me some comfort.
"The orientation session begins in ten minutes in the ballroom," Sailor Hat was telling the couple who had just registered. I glanced at my watch and confirmed it. So I turned around and tried to picture the route back to the ballroom.
In my mind, I kept asking myself, "What am I doing here?" It's been three years since my Caroline died. We were married before we were twenty and had already celebrated our fortieth anniversary. I loved her like no other. We had a good life, raised a good family, and yes, had good sex. But I always knew that I was attracted to cock more than pussy. I just never acted on it. Oh, I snuck plenty of beefcake mags into the house. And when the internet got established, I became a frequent flyer on the gay porn sites. I fantasized daily about what I would do with a man. But in body, I always remained faithful to Caroline.
When she died, I began to explore my homosexuality. I bought books like The Joy of Gay Sex. I found a gay sex shop and rented gay videos. I went to a gay bar where, on Friday nights, male dancers would strip down to their jocks for tips. But I always went home alone. I read the personals, especially those on websites that sorted them by location. I found that there were actually men who were looking for older guys. But I never found the one who seemed right enough to contact.
In a lot of ways, I knew I was still not ready for an active gay lifestyle, but now at least I could explore it openly. I looked at ads for gay vacations: there were B&B's that catered to gays, there were tours of Europe, there were nudist camps. I considered them all. I didn't rule anything out, but I deliberated about the pros and cons of each option. But when I saw the ad for the Pillage and Plunder cruise, I acted impulsively. I called them up, gave them my credit card number, and before I realized what I had done, I was signed up.
Of course, I could have backed out and gotten my money (well, most of it) back. And several times over the months that intervened I had the phone in my hand ready to do just that. But I never made the second call and now here I was on board the Regal Empress, still wondering, "What the fuck am I doing here?"
What am I looking for? What am I expecting? What do I want when these four days are over?
The organizers were taking their turns at the mike outlining the schedule of events: the scavenger hunt, the best buns contest, the biggest dick contest, the talent events, the day in Cozumel. I had read the literature so I was already aware of all this.
Then we were introduced to the stars. As part of the enticement to get passengers to sign on, Gay Pride Tampa manages to get several porn stars to take part in the cruise. It's a chance to get to meet these guys close up and personal, get their autographs, get to touch them, and get to fantasize about doing something dirty with them. I began to pay more attention now.
Spike appeared wearing a Boy Scout uniform. Hey, didn't he learn that scouts are supposed to be morally straight? Chad Hunt, Logan Reed, one after another I watched the guys parade on to the stage, guys whom I had watched getting fucked in their videos, guys whom I had fucked myself many times in my mind.
The meeting broke up and most of the audience began barraging Spike and the other stars. I figured there'd be enough time later on to meet them, so I wandered back to my room. I passed several crew members in their neat, pressed white uniforms. I caught sight of a couple of well endowed packages, but even though I was among a shipload of gay passengers, I still felt self-conscious about staring. All those years of marriage had conditioned me to be discrete when out in public.
I also passed fellow passengers, and confirmed in my mind that I was doubtless the oldest on board. Some were already parading around the ship in their speedos, and some were even walking around in their tighty whities! Wow! Discretion of not, I had to stare. Could I walk around like that? I wondered.
I was still in a daze when I got to my room and opened the door. That's why I was surprised to see someone else inside. Of course, I knew I would have a roommate, but somehow I expected to find the room just I had left it, empty. Now here was another man unpacking his luggage on my bed. He turned toward me and I recognized the man I had seen earlier with Mark, the tan jacket, bermuda shorts and white sox that extended up his shins. "Hi, my name is Phil. I guess we're bunkmates, Rick B." Phil extended his hand.
"Uh, yeah, hi," I stuttered. I realized Phil had read my nametag with those huge block letters and that fuckin initial. Phil had thinning gray hair, a bit of a paunch at the waist, but actually looked fairly fit for a man in his, what, at least in his fifties.
"I didn't know which bunk was mine. Do you have a preference? Or did you think we'd share the same one?" Phil winked. I should have left some of my stuff out on my bed before I left, but I wasn't thinking. The reality of a roommate was only now beginning to sink in. My last roommate had been Caroline. For three years, I had slept alone. Suddenly I realized I was staring at this guy.
"I'm sorry, Phil. I just feel a little awkward. This is my first time." I realized "first time" could be taken a dozen different ways, and I guess all of them were legitimate interpretations.
"Don't worry. We have plenty of time before supper. What do you say we go get a beer and get acquainted. My treat."
At the bar, Phil got a Bud light, and I got a 7Up. I explained that I really didn't drink, and he was cool with that. We sat down, and Phil began. He was gregarious. Unlike me, he seemed to have no qualms about opening up to a stranger. Phil explained he was from a little town in Wisconsin, right on Lake Michigan. "Trivers, that's how we say it, but it's written Two Rivers." Phil was surprised that I'd actually heard of the place. Somewhere I had read that the ice cream sundae was invented in Two Rivers. Phil laughed. I felt more at ease.
"I'm from Long Island, New York. I live in a retirement community there."
"No shit! You look so young, Rick B."
"Please, forget the B. I shouldn't have put that on there." I told him about my nervousness at the registration table. "I'm 65 by the way."
"Damn. You look real good for 65. I'm 69!" My jaw dropped. Fifties maybe, but I would never have pegged Phil for being my senior. "I guess that's why the organizers put us together. Figured we'd have things to talk about." Phil laughed heartily. He took a swig of his Bud and then turned solemn. "I'm a widower, Rick. Agnes died last year. I'm actually kind of new at this gay scene." I was again amazed. I told Phil about Caroline, and we both realized we had a lot more in common than the decades of our age. Phil also had explored gay porn, he also had tried the bar circuit, and now he felt he was ready to move on, whatever that meant. In a couple ways Phil was already a few steps down the road ahead of me. He had a gay son, so he was familiar with some things second hand. And he had had a couple oral experiences with a man.
"Well, I guess we should get changed for supper," I ventured. Phil paid the tab and we began strolling back to our room. We passed a few couples as we walked, and suddenly I realized that Phil had taken my hand in his. I didn't resist. It felt good. I thought back nearly five decades to the days when I took Caroline's hand as we walked. I had never held hands with a man since I was a toddler holding my Daddy. Now, I was walking hand in hand with a beautiful mature gentleman. I chalked it up as my first truly gay behavior.
When we got to our state room door, I said, "I'm really glad we're roommates, Phil. I'm beginning to think I'm actually going to enjoy this cruise." Then without thinking, I leaned forward and kissed his cheek. My second truly gay behavior.
I leaned back from him. He smiled. "You know, Rick, I've never kissed anyone with a beard before." Phil leaned forward again and planted his lips squarely on my mouth. We kissed lovingly and softly there in the hallway. When we let go, I realized there were other guys in the hall, but it didn't seem to matter any more.
We got inside our state room and closed the door. Phil went over and closed the curtain over the porthole. I doubt that anyone on the dock could have seen anything, but I saw that Phil was just as discrete as I. He kicked off his loafers and pulled off the tan jacket. I began with my shoes and socks. Phil sat on the bed (my bed?) to take off his sox and watched me as my shirt buttons opened to reveal my chest. "Very nice. I like a guy with a hairy chest."
"I got a hairy ass too," I blurted out.
"Sure would like to see that."
I stood in front of him, turned my back, and slid my jeans down my legs, then pulled down my briefs so Phil could admire my hairy crack. "Well, what's your verdict?" I tried to joke. Instead of hearing his answer, I felt his mouth on one buttock. He gave me a long soft kiss, then slid his face over toward the other buttock. The next thing I knew I felt his wet tongue licking my crack. It felt wonderful. I closed my eyes and felt my whole body shudder as he licked my hairy crack. Another truly gay behavior. I realized my dick was getting excited.
Phil stood up, turned me around and kissed me again on my mouth. "I'm also glad to have you as my roommate, Rick. I want this to be a good experience for both of us." Phil then dropped his bermuda shorts. Standing in his t shirt and boxers, he suggested it was time to get showered and dressed for supper.
We took turns in the cramped head, but allowed each other to watch as we showered off. Tonight was supposed to be Leather Night. I had brought along a bomber jacket. I decided with a pair of jeans, a pair of boots, and a pair of shades that would pass for a leather outfit. I watched as Phil pulled out a pair of shiny black chaps and a black vinyl vest. They looked brand new. Under these, he wore a pair of denim cutoffs and a clean gray t shirt. He looked exciting. The way the chaps framed his crotch in front and his ass behind made me quiver. As the coup d'gras, he sported a jaunty motorcycle cap.
When we arrived at the dining hall, about half the passengers were already seated. There was no assigned seating, so we selected a table back from the dance floor. It was a table for four; there were none for two. We sat down and waited to see if anyone would join the two old farts.
I told Phil that in high school I was always getting kidded about being Dick. I hated the name. As soon as I moved away and began living on my own, I called myself Richard. Everyone, my wife, my friends, my coworkers. They all knew me as Richard. If someone tried to shorten it, I corrected them. After Caroline's death, I wanted to do something to mark a new beginning in my life. So I assumed the moniker Rick. Phil said he liked it, that I looked like a Rick, whatever that meant. He reached over and took my name tag, slid it out of its plastic holder and deftly folded the offending initial back. He replaced the card which now simply read "Hello, my name . . . Rick" (the "is" got folded back also.) "There, that's better," he pronounced and handed it back to me.
"Is this seat taken, Mate?" Phil and I looked up to see what was attached to this voice. There stood a gorgeous man, in his thirties, slightly short, brown hair. A stache and small goatee framed a beaming smile. He wore a vest like Phil's, but was bare chested, except for a leather harness that crossed his chest in a Y, with one strap shooting down into his leather shorts. He also wore a leather armband.
"Hell, I know you," Phil said. "You're Peter Raeg! I saw you in Missing Link!" Stupid me, why didn't I recognize him. All the porn stars on board were pictured in the literature. "Hell, no, the seat's not taken. Come, take a load off."
"Thanks, Mate. Lance will be along in a few minutes, if you don't mind." Lance Gear was Peter's lover, I remembered. They had moved to Sydney which explained the "Mate" business. "I like your beard, Rick. In fact, I always preferred hairy guys. I spotted you two right off when I came in here." I don't know how much of Peter's schmaltz was on the level, but he made us feel good, sitting and chatting with us. He was a natural guy with no hint of attitude. Lance did come by, but after shaking our hands and giving Peter a wet sloppy kiss, he said he ought to move on to some other table, spread the wealth so to speak. It wasn't a put down at all, though we would have loved to have his company also, but he was a professional, and he knew the passengers expected to meet the hunks they had masturbated to on the screen.
Fans did come by our table all evening to get Peter's autograph or get their picture taken with him. We enjoyed watching him with his fans. He listened with honest interest as we told him our stories. When the dancing started, he wished us the best of luck and headed on to the dance floor where he accommodated everyone who wanted to dance with him. Phil and I knew we wouldn't see him the rest of the night.
At the bars I had gone to on Long Island, I had sometimes stepped on to the dance floor by myself and shimmied my ass around to the music. Occasionally, a punk kid would come over and dance in front of me, maybe thinking I was a potential sugar daddy, but I had never actually danced with a man. But when Phil asked me, I was ready. The music then was slow and romantic. The couples on the floor were holding each other tight. We stepped on to the dance floor and immediately pressed our bodies together and grabbed each other's ass. Another truly gay behavior, but I was already losing count.
All of a sudden, my anxiety abated. Dancing (well, moving anyway) with my body pressed against Phil's, my hands caressing his ass, his strong arms enveloping me, my head on his shoulder, eyes closed, his head on mine whispering softly in my ear, -- I was finally at peace with this strange world, with my new lifestyle, with myself. The other couples on the floor seemed to disappear. Phil and I were alone; alone in heaven. Then I thought of all the times I danced with my Caroline; we preferred a slow waltz. Now here I was dancing with someone new. But I felt no guilt; I didn't feel I was in any way betraying her, or dishonoring her memory. It was almost as if she were there, smiling on me, finally accepting me for who I really was, blessing my behavior. My eyes began to tear.
"Something wrong, Rick?" he whispered in my ear.
"No, not at all. Damn it, I'm just so happy right now."
"I can tell." Then I realized that I'd grown a boner, and with our bodies pressed together, there was no hiding it from this wonderful man.
"I'm sorry. I didn't realize."
"No need to apologize, Rick. I'm flattered. Let's say we go back to our room and take care of it."
"I'd like that very much." I felt my erection was the biggest thing in the ball room. I remembered as a kid in Junior High getting an uninvited hardon and dying of embarrassment. But maybe this time I was just flattering myself; it probably wasn't all that obvious, especially with the low lighting. And if any other passengers did notice my bulge as Phil guided me to the exit, well, after all, isn't that what a P&P cruise is all about?
Walking back to our room, Phil kept turning toward me and kissing my cheek. "I think I'm falling in love, Rick," he whispered. Finally, just yards away from our door, I couldn't resist. I stopped, turned to him, put my hands on his cheeks and planted a full kiss on his mouth. There was no holding back the tears now. I gushed like a teenage girl who'd just found the "one."
We ran the remaining distance, fumbled with the key, and stumbled into our room. We flopped on the nearest bed and began unbuttoning and unbuckling each other, while trying not to interrupt the string of kisses. Phil got my jeans and briefs down to my knees and starting working on my manhood. I couldn't untangle his chaps-covered jeans enough to reciprocate so I just leaned back and let him take the lead. With me mostly naked, and he mostly dressed but with his cock freed, I began my first gay sex. I knew this was what I wanted, and I allowed myself to swim in all the emotional currents of the experience. As his strong, knowing hands worked on my cock and balls, I kept running my hands up and down his arms. When the precum began to flow, he leaned over and took me into his mouth. I held his head, running my fingers through his thinning hair. Every nerve ending in my body was on high alert, and as he began licking my shaft, my legs began to tremor. Phil had said he'd already had oral sex so I tried to concentrate on his technique, tried to learn from my mentor, but it was useless. My mind was flying in a thousand directions, as my emotions were cascading in only one. I was tumbling into my new homosexual world with all the unstoppable motion of an avalanche. I gave up thinking, as I had already given up resisting. Phil brought me to the verge of climax. He seemed to know exactly when to ease up on the sucking.
"I want us to cum together," he whispered. I realized then how selfish I'd been, relishing his attention on me, and not giving him any. I reached over and started exercising his uncut cock, already hard and oozing.
"Phil?" I mumbled.
"Yes, Rick, what is it?"
"I want you . . ."
"What?"
As I said, my mind had already turned off, so I don't know where this came from but I said, "Phil, I want you in my ass."
"Are you sure, Rick?"
"Not at all, but yes, definitely," was my nonsensical reply.
"Hold on." Rick grabbed his souvenir bag and began fumbling about inside it. He pulled out the tube of KY he remembered seeing there and a condom. We both quickly removed the rest of our clothing, and I laid down face up, grabbed my knees and pulled them up as high as I could. Phil applied a liberal dab of KY on my hole. Then one finger invaded my chute. Fuck, it felt so good to finally have a warm, loving human organ inside me. He continued to lube me up, then tore open the condom. My eyes were glued on him as he rolled it on his shaft. He leaned forward and I rested my ankles on his shoulders. I felt his dickhead pressing on my sphincter and began involuntarily gritting my teeth, but I gave him a big smile. Phil lunged and suddenly his cock was inside me. Oh fuck! My entire body exploded. I felt the heat of a thousand fires. He began pumping; in and out. He took my ankles in his hands and spread my legs wider. It felt like he was going a mile up my asshole.
We both moaned. All those years of hetero sex with children in bedrooms down the hall had trained us both not to yell out the emotions we both felt. We moaned and whispered, "Fuck," "Yes," "Don't stop." Then Phil leaned in, his lips inches from my ear and whispered, "Oh, Agnes." I don't think his own ears heard it. He continued his rhythm and soon his whole body tensed and became catatonic. Then I felt the warmth as he released inside my hole. Simultaneously my own dick, sandwiched between our two bellies, also erupted. Phil collapsed on top of me and I held his sweaty body.
"I love you, Phil."
"I love you, Rick."
"I know."
Phil began to frown as his mind started to take account of the last few minutes of ecstasy. "Uh, Rick?"
"Yeah?"
"Did I call you Agnes just then?"
"Yeah," I smiled.
"I'm sorry."
"No need to be, Phil. I was happy. It made me think we might have something real going here. For my part, I'm ready to start the next forty years with my new lover." We both broke into laughter, as we did the arithmetic.
"It's going to be a great cruise!"
I wasn't sure if Phil meant the literal cruise or the metaphoric one, but my answer applied to both: "It sure is."