Date: Tue, 18 Jul 2006 18:21:19 -0500
From: Herb Cat <herb_cat@lycos.com>
Subject: Pillage and Plunder Cruise

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."