This story is copyrighted by me, Shon Richards.  Please don't plunder it 
for your own pleasure.

	I wrote this story a few years ago and even though I know I can write 
better, I think it has a certain charm.  This is the first part of a FINISHED 
novella that involves a male sub, one eccentric female Captain and a ship full 
of sexually adventurous women.  Yes, it's that kind of story.  There's bondage, 
domination, spanking, oral sex, anal sex, orgies, pirate lingerie and even a 
little romance.  What there isn't any of are pedophilia, nonconsensual sex, and 
anything involving former food.    

	Big thanks to Souvie and Pami who always had an interest in this story and 
bugged me to post it.  Big thanks to Alexis who told me I could do better.  A 
big thanks to all the Thigh Vs. Thigh fans who let me know that funny erotica 
had an audience.

"Her Cabin Boy"
By Shon Richards  


	"Wanted, male between the ages of twenty-one to twenty-five, with an 
interest in pirate history.  Job includes room and board aboard a privately 
owned ship that will be making a voyage to the Caribbean.  Duties will include 
sailing, housekeeping and various odd jobs.  Only enterprising men need apply."

	It was too good to believe, so I read it again.  I had been looking for a 
summer job between college semesters and this looked more like a vacation than a 
job.  Growing up in North Carolina, I also had a passing interest in pirates.  
It was hard not to when you lived in the state that Blackbeard made famous.  It 
was an odd request though; I wasn't sure why pirate history was going to be 
important on a voyage.  Maybe it was a trip to visit all of the historical 
pirate ports.  It didn't matter; I decided to go apply at the address provided.  
A Caribbean voyage sounded a lot better than staying with my parents!

	I went immediately to the rented office that morning.  There was a group 
of men applying at the rented office that I arrived at.  I became a bit nervous.  
My sailing experience was non-existent, and there were at least twenty 
applicants already.  The secretary gave me a package of forms to fill out, and I 
sat down at a provided desk.  It was hard not to sneak glances at the secretary.  
She was extremely cute for a blonde, as well as young.  She couldn't have been 
any older than I was.  I noticed that a lot of the guys were staring at her, 
which made me wonder how many applicants they could process with such a gorgeous 
distraction. 

	The first group of forms was really strange.  Due to the 'scientific 
nature' of this job, total secrecy and confidentiality was required of the 
applicants.  I had to fill out seven forms that stated that I would in no way 
reveal the contents of the questions asked me.  The legal consequences of even 
describing the wording of the questions were pretty severe and graphically 
described.  That should have been a warning sign to me, but instead I was only 
further intrigued.

	After my signatures validated my secrecy, the normal questions were asked.  
My name, address, age, and social security number was expected.  I didn't see 
where my weight, height, hair and eye color came in, but I filled those in 
anyway.  Questions about my health were to be expected I guess, although having 
to state that I had no sexually transmitted diseases made me giggle a bit.  It 
was nice to know I wouldn't be sharing a ship with anyone with VD.  After I 
described myself to the satisfaction of the questions given me, the really weird 
questions began.

	"What town did Henry Morgan become famous for sacking?"  That was easy, 
Panama.

	"From whom did Captain Avery make his one and only conquest?" The Great 
Mogul was the answer I remembered.

	"Name the two female pirates of the Caribbean."  After answering that one, 
the questions got harder.  They ranged from history questions, to vocabulary, to 
identifying the Captain's cut of the plunder.  There wasn't a single one that I 
didn't know, which gave me quite a bit of pride.  I'm just glad that I didn't 
have to mention that I got most of my answers from the 'Pirates Gold' video game 
I used to play in high school.  No matter where my information came from, I was 
on a roll when I ran into questions even stranger.

	"How many women have you had sex with?"  What the Hell does that have to 
do with anything?  My answer was two, although my natural male instinct was to 
pump the number up.  

	"What experiences have you had with bondage, domination and submission?"  
Other than some dirty books and a pair of handcuffs, I didn't have much to 
answer here.  I was getting the impression that this cruise was turning kinky.

	"Are you bisexual?  Are you tolerant of other bisexuals?"  Warning signs!  
A happy heterosexual, I answered honestly and gave my politically correct answer 
on tolerance.  I had this terrible feeling that these guys were hiring a 'cabin 
boy.'

	More questions on my sexual experiences were answered, and to my surprise, 
I was done.  No questions on my sailing experiences or questions on my academic 
qualifications were asked.  After handing in my application, the secretary 
graded the questions on pirate history right there.  I had to keep from smiling 
as she checked each one off.  Then she told me to walk through the door for my 
interview.  Just like that, I had moved to the next phase.  Who would have 
thought all those hours of playing pirate games would help get me a job?

	Steeling myself for the usual professor type, or an eye-patched guy with a 
peg leg, I entered into the inner office.  The lady inside was a pleasant 
surprise just because it was a woman.  The office was almost barren, consisting 
of a desk, a chair, and two chairs in front of the desk.  The shades were drawn, 
giving the room a very dark and almost secret feel.  I closed the door behind 
me, presented my papers to the woman who waited for me.

	Dressed very nicely in a red pantsuit, the stunning older woman behind the 
desk gave me a warm 'hello,' and a firm handshake.  Her red hair was pulled back 
in a very neat ponytail, and her gray eyes looked intensely at me behind very 
thin gold frame glasses.  Small laugh lines betrayed her age, but they added 
detail to an already arresting and fascinating face.  Small lips painted crimson 
parted to flash perfect white teeth at me.  I sat down at her request, and did 
my damn best to not fidget.

	"My name is Ashlyn Drake, and I am the one you will be working directly 
under if you are hired."  She flipped through my application, "Mr. 
William Rosen.  You are the first person to answer all the pirate trivia 
correctly.  What brought you to our unique employment opportunity?"

	"It was the chance to get away from the summer," I answered.  Realizing 
how desperate that sounded, I worked quickly to use all the knowledge I gained 
from reading employment pamphlets in my dorm.  "I also look forward to the 
chance to participate in an actual voyage that has anything to do with pirate 
history.  I'm a big fan of that period in history and I think I can learn a lot 
by working here."

	She tapped a pencil as I babbled, and smirked at me slightly.  Looking at 
my application, she said, "But William, you haven't any idea what the job is.  
How can you be so sure you want it?"

	She had me there.  Not knowing what to say, I shrugged and said, "Because 
I'm naturally enthusiastic?"

	Ms. Drake simply nodded, and for no reason, she unbuttoned the top button 
on her suit.  I did my best to ignore that, and I think I did an admirable job 
of not looking at the resulting cleavage.

	"You see William," she said as she played with another button.  "I am a 
very wealthy woman, and I have done just about everything I can think of at my 
age.  I have known love, I've traveled, I've made enemies and good friends, and 
I've tested myself against the world.  With every whim easily satisfied, I often 
think about those who weren't as lucky as I am.  It's fascinating to me how poor 
people have indulged in the worse debaucheries, when they were the ones who 
could least afford to do so.  Naturally, this has led me to an interest in the 
pirates."

	She lost me there, but I nodded wisely anyway.  

	She unfastened the second button, and ran her fingers down between the 
valley of her two breasts.  I betrayed no emotion as my cock hardened. Somehow I 
believed that she had no idea of what she was doing, and I certainly didn't want 
to call attention to her actions.   

	"The pirates of the Caribbean were foolish, uneducated men who preyed on 
some of the greatest riches of the world," she continued.  "Despite all the 
odds, and despite common sense, these men plundered against over whelming 
forces.  These men engaged in atrocities that shamed the rest of the world.  
There must be something magical about being alone on the sea, that I believe it 
gives people greater freedom.  This is the freedom I'm looking for, and it's 
what I'm planning to simulate on this voyage."

	"Quite simply, I'm creating a ship crewed by women completely under my 
control," she said as her fingers played with the third button.  "I want to 
simulate the absolute freedom and the power the pirates possessed.  I've always 
had power over people, but I suspect that there is even more power if the 
environment of civilization is removed.  On this ship, my word will be law, and 
I intend to test that to the limit."

	"Women?" I gulped.  That third button was loose, and the green of her bra 
was peeking at my eyes.  God, I couldn't help but stare at the softness that was 
barely constrained by her lacy green bra.

	"Definitely women," Ms. Drake answered.  "I'm bisexual, but too many 
failed romances have soured me towards having any lasting relationships with 
men.  At my age, I think I've earned the right to stick to what I like.  Don't 
you agree?"

	I nodded my head.  It was difficult to watch her unbutton her vest while 
listening to her sex life.  Oddly enough, I was giving both my undivided 
attentions.

	"That is where you come in," Ms. Drake said, and she rose from her desk.  
Walking around her desk and standing beside me, she placed her hand on my 
shoulder.  I happily had to look up at her, and somehow not look up her 
cleavage.

	"As much as I prefer female company, I also know that I often need the 
companionship of a male," this beautiful though eccentric woman explained.  "I 
want you to join my crew as we travel to the Bahamas.  You'll serve as my 
assistant as I command my ship, and help me in my experiments.  You'll also 
serve as a status symbol, as I will be the only woman on board with a male 
companion.  The voyage will take two months, and you'll be compensated for five 
thousand dollars a week.  Of course, to earn this money, you'll have to be 
totally obedient, as well as engage in an exercise program, as you do reflect on 
me."

	"Five thousand a week?" I gasped.  "All you need is an assistant?"

	Well," she said as she undid a fourth button.   "Let's just say that 
you'll also be warming my bed.  Do you have a problem with having sex with an 
older woman like me?"  She shed her suit top and let me appreciate her full 
breasts barely held by her bra.

	"No problem at all," I quickly answered.  Sure, I didn't really think 
about the implications of taking the job, but when a lovely woman asks if I'll 
sleep with her, I've found that hesitation is usually a bad thing.  My desire to 
bury my face in her breasts out weighed any reserve I had about being alone on a 
ship with this slightly unbalanced woman.

	"Good, now before I can hire you, I need you to strip down," she said 
simply.  She sat on the edge of her desk and rested her hands on her crossed 
legs.

	Before I could think of a good reason not to, I stood up.  As crazy as 
this all sounded, and as unlikely as it was that I was auditioning for a 
decadent sex cruise, a part of me was hoping that all of it was true.  People 
like me don't get selected to be the sex toy of attractive older women, and I 
was finding that the opportunity to become one was too rare to ignore.  This was 
all happening so fast; I was stripping before I my courage backed out on me. 	

	Sucking in a deep breath, I unbuttoned my white shirt, starting at the 
top.  Ms. Drake watched me intensely, and I felt a small bit of pride swell up 
in me.  I knew I didn't have a bad body, I play too much basketball to go 
flabby.  I dropped my shirt on the chair, and kicked off my shoes.  This was the 
hard part coming up now.

	Trying to ignore my shyness, I unzipped my pants and pulled my pants down.  
My cock was springing from my underwear, and I could feel the heat on my face as 
I blushed.  My heart was pounding in my chest, and I wasn't sure if I could 
continue.  This woman was so confident, so clinical and so beautiful, she was 
intimidating the hell out of me.  Kicking off my pants, my fingers gripped my 
underwear and hesitated.  Ms. Drake simply raised her eyebrows as she looked at 
me, almost amused by my shyness.  Biting my lower lip, I took off my underwear 
and put it on the chair as well.

	There I was, all six feet four inches of me, standing nude in front of my 
new boss.  I had no idea what to do with my hands, as it's hard to be casual 
with a large erection.  

	"Not bad," Ms. Drake said as she stood up.  She walked around her desk to 
me.  Her hands reached down and squeezed my ass, and I remained absolutely 
still, although my cock did throb a bit.  I felt her hands touching my back, and 
I almost sighed when she gently grabbed the back of my neck.  She ran her 
fingers through my short brown hair, and I was just praying that maybe I we 
could have sex right here and now.

	"Your cock looks about the right size," Ms. Drake said as she gripped my 
manhood firmly.  "We still have to check your fit though, so put on this 
condom."

	Handing me a small condom package, she then said, "Of course, if you are 
hired, you'll have a full medical and we won't have to use these again."

	I was already rolling the sheer latex onto my cock.  The surreally of what 
was happening was making me follow along numbly.  A rich woman wants me to put 
on a condom in her office?  Fine with me.  Auditioning for the role of a boytoy?  
I can do that too.

	With my condom in place, and after Ms. Drake checked it for slipping, I 
was treated to the sight of more of her clothes being removed.  She wiggled out 
of her pants, and I was able to appreciate her porcelain legs.  There was a bit 
of inadequacy on my part; the muscles that rippled under her legs put my legs to 
shame.  She might be an older woman, but she was healthier than any woman I had 
ever been with was.  The hard curves of her legs and buttocks were turning me 
on, not that I really needed any more arousal.  My new boss turned around, 
presenting me with her inspiring buttocks.

	"Go ahead William," she said, looking at me over her shoulder.  "Board me 
and let's see how you feel."

	Touching her carefully around the hip with one hand, I used my other hand 
to guide my cock into her warm tightness.  Penetrating her slowly, I controlled 
myself from just ramming into her.  Her lips parted for my cock, and closed 
around me tightly.  After a lifetime of sliding into Ms. Drake, I was finally 
completely inside her.  My cock was throbbing in time with my pulse, and I 
thought I would explode just from being here.

	"Very nice," Ms. Drake purred.  She leaned over and was flat on her 
desktop.  "I like the feel of your saber, but let's see how you fence with it.  
Let's see some action William."

	Encouraged, I allowed myself the exquisite pleasure of a simple thrust.  
Unlike my previous experiences with other women and their vaginas, Ms. Drake's 
seemed to flow around me.  There was a constant pressure around my cock, but 
never any resistance.  My hips bumped gently into her ass; I didn't go any 
faster because there was simply no need.  I was enjoying myself too much to want 
to climax.  I also wanted nothing more than to get this job and my sensitive 
modern male mentality told me that women weren't fond of getting their asses 
slammed by a raging male.  

	"So tell me William," Ms. Drake, her voice low and gasping.  "Can you go 
any faster or does your weapon always require such careful aim?"

	Ok, so I was wrong.  My future job on the line and five thousand dollars a 
week at stake, I swallowed my sensitivity and let her have it.  I planted my 
feet firmly, and reached under her waist for support.  Her ass felt wonderful as 
my hips crashed into her, my cock was surging as I stabbed repeatedly into her 
sex.  The desk was moving under our impacts, the tiny scraping of the floor in 
sync with Ms. Drake's moans.  I was lifting her with my thrusts, and my 
breathing grew faster as my climax approached.

	"Quit, quit, quit," she breathed, and I stopped in mid thrust.  "I want to 
save you till we get on the ship," she said as she slid easily off of me.  I 
looked at her with disbelief, I was so close to climaxing, and she wanted me to 
stop?

	"Wipe that look off your face," she said as she pulled her pants back on.  
"Take the condom off, and masturbate for me.  You can tell a lot about a guy by 
the way his face looks when he cums."

	"You mean masturbate, right here?" I asked.

	"Sure, don't worry about the mess, I have people to clean it up," she 
responded, her lovely breasts disappearing under her jacket.  "Well?  What are 
you waiting for?"

	This was embarrassing.  "It's just that I've never masturbated in front of 
someone before."

	Her head titled to the side as she smirked.  "There's no room for shy 
people on this ship," she said.  "I admit, I do find a bit of modesty 
attractive, but you'll have to overcome this if you want to work with me.  Think 
of it as your final test, if you can't masturbate while I watch, then maybe this 
job isn't for you."

	Trapped between my greed for this job, and my embarrassment at performing 
a personal act, my desire for this job won out.  I slipped off the condom, and 
dropped it into the garbage can by her desk.  Resisting the urge to close my 
eyes, I faced Ms. Drake and held my cock in my hand.  The corners of her lips 
turned up slightly, and I could see the little pink of her tongue.  Not wanting 
to stall, I stroked myself.

	It was easy once I got started.  My cock had deflated slightly, but the 
memory of her tight pussy was still in my mind.  Placing my fingers around my 
cock, I stroked myself from base to tip.  My fingers would stop just short of my 
head, as I was too turned on and too sensitive for stimulation there.  Ms. Drake 
watched me the entire time, her hands folded on top of the desk.  I had the 
impression that I was being studied, and for some reason, that turned me on even 
more.  

	My other hand was on my hip, and I looked right at my future boss as I 
felt the surging in my cock.  Not thinking of anything but my own immediate 
pleasure, I finally ejaculated.  My legs trembled as the force of the orgasm was 
much more than I had experienced before.  My essence sprayed out of my cock, and 
I decorated the side of her desk with my messy fluid.  I didn't care though, I 
was shuddering as I climaxed, and I was shaking my hand faster as I drained 
every bit of my semen out.  

	The sound of Ms. Drake clapping brought me out of my bliss.  "That was 
excellent for a first time exhibitionist," she said.  "I think I'll definitely 
have a place for you on my ship."

	Before I could say thanks; she pressed a button on her phone.  The side 
door opened and the secretary walked into the room, and I was still butt-naked!  
I rushed to put my clothes back, while Ms. Drake laughed the entire time.  The 
cute secretary just ignored me however.  She got down on her knees, and began 
wiping up the mess I made with a box of tissues.  I didn't know which 
embarrassed me more; the fact that I was nude and everyone else was casual about 
it, or the fact that it was taking an awful lot of tissues to clean my mess up.

	"We set sail two days from now, but come by the ship tomorrow morning so 
that our doctor can give you a clean bill of health.  If you check out ok, then 
you'll need to bring a passport the next day, then we'll be off."

	"How much clothes should I bring?" I asked, still embarrassed by the 
secretary trying to remove a stain from the carpet.	

	"Don't worry about that," Ms. Drake answered.  "If you pass our doctor's 
tests, then we'll buy all the clothes you need for your duties.  All you need to 
bring is your passport and that enthusiasm you mentioned earlier."

	"Now you better go," Ms. Drake said as the secretary finished with the 
carpet.  "You might not pass the physical, so I better audition some more 
replacements just in case.  Ms. Kent here will give you the address you need.  
Good luck, because I would be disappointed if I had to leave without you."


To be continued.