Sailing -- Part 1

[Guest faggot hole]

For my sophomore and most of my junior year in college i was in a "relationship" with my Economics professor.  i got straight As; but in honesty i think the As had nothing to do with the fact that he was fucking me.  i got an A in the introductory course that was taught by a different professor (and i had no interest in fucking her).  True, the fact that he was fucking me 2-3 times a week might have encouraged him to give me the benefit of the doubt in grading, if that situation ever came up, but i think i pretty much earned those As.

 

But i digress.

 

my prof. was a stunning looking man, late 30s or early 40s, more than 6 feet tall, awesome body, prematurely graying hair, piercing blue eyes.  He walked around campus like a true athlete and girls swooned.  Sorry girls.  This dude is seriously into boys. 

 

Anyway, we are laying on a bearskin rug in front of a roaring fire at the prof's lakeside lodge on a late November afternoon, in post-coital haze.  Prof is sucking on a blunt and passes it to me.  i take a hit and pass it back.

 

"What are your plans for semester break?" He asks.  Exams end just before Christmas and the second semester doesn't start until mid-January.

 

"Don't have any plans, really.  Probably go home and hang with my dad and brother.  Why do you ask?" 

 

"Well, my buddy Jim is moving his sailboat from Florida to one of the islands and he's looking for crew.  I'm going to help him out and i thought you might like to come along."

 

i thought about it for a few moments.  "I don't think so," i said.  "i can't afford air fare to Florida and beside, i don't know the first thing about sailing.  i wouldn't be any help."

 

Prof. responded.  "Don't worry about it boy.  I'll cover our airfare.  And believe me, you'll pick up on boating really quick.  Come on, we'll have a great time in the sun."

 

So i agreed and emailed my dad to tell him i would not be home for Christmas.  As the departure date grew closer, prof started instructing me on the elements of sailing after we had fucked, and told me stories of his previous abventures in the islands and with his buddy Jim.  When i suggested that i really needed to get some clothes for the island climate, prof told me not to worry, he'd make sure i had appropriate clothing.  So, when he picked me up for the airport, on the day after my last exam, i had packed light -- couple pair of shorts, a couple tee shirts, tennis shoes, a couple pair of sox and toiletries.  As it turned out, of these few things, i would use only the toiletries.  When we arrived in MIami and got into our hotel room, prof handed me this tiny little plastic bag.  "What's this?" i asked.  ""All the clothing you'll need on the boat," he responded.  i opened the bag and saw one of those absurd, expremely low cut Japanese speedoes, in black, and a thong in royal blue.  As things turned out, i wouldn't wear even those "garments" very much.

[Giftundpozempfangb]

so far it started good, now I happened on it on the boat looking forward

 

[whorepig]

Too bad there isn't more was just getting good

[mike43]

Great starters hear more

[atlbtmpig]

nice start

[Guest Lempriere]

I love sailing stories.

[Guest faggot hole]

Sailing --Part 2:  i don't know much about boats but Jim's boat was one impressive vessel.  Two masts and like acres of sail.  I later learned the details.  It was what is called a Ketch, it was 56 feet long, had two "staterooms," two bathrooms (heads), a lounge and a fully functioning kitchen downstairs (below decks), radar, sonar, GPS, the works.  I have no idea how much this boat costs, but it clearly costs more that i was ever going to be able to afford.  Jim had assembled a crew of 4;  himself, the Prof and two other guys, Matt and Mitch.   i don't count myself, as i learned that i had not been brought along to crew the boat, but rather to service the crew.

 

The Prof and i checked out of our hotel the morning after we arrived and took a cab to the docks.  We easily found the boat and Jim was there to welcome us on board.  He and the Prof kissed each other, after which the Prof introduced me and Jim reached out and tousled my hair, like i was some kind of pet dog.  "You guys put your gear in the aft stateroom," Jim instructed.   The Prof showed me the way below decks. We stowed our gear and the Prof told me i could lose my tee shirt.  We went back above decks, me in my cargo shorts (and barefoot -- the Prof told me that tennis shoes were bad form on a yacht, i could wear boat shoes or go barefoot.  i didn't have boat shoes, so ....)  Over the next few hours we welcomed Matt and Mitch aboard (again a lot of kissing among the guys and a lot of exclaiming about how good everyone looked), Jim and his crew hauled anchor, and did the riigging, whatever, and under the power of an inboard motor, we putt-putted out of the marina and headed for the open seas.  Once we were out of the marina, the crew rigged the sails, and the Prof sent me down to our room to change,  "lose the carge shorts.  Wear the thong i bought you." 

 

By the time i returned above deck wearing the thing and feeling awfully self-conscious, the sails were fully set and catching the wind (i don't think i have the nautical terms right here) and the guys were each relaxing with a beer, except Jim who was at the wheel.  The prof introduced me to Matt and Mitch as his student who he had been fucking.  The Prof looked at me and said, "I could use a blow job right now."  i looked at him and arched my eyebrows, as if to question "here,now?"  "We're among friends, Josh," the Prof answered.  Look around.  There are no other vessels in sight."  He pulled down his shorts exposing that unbelievable, magnificent cock that he knows i cannot resist.  He spread his legs.  i walked over, knelt between his legs and took his awesome cock in my mouth and started working on it.  All the time he and Matt and Mitch were talking, catching up on the events of their lives since they had crewed for Jim the year previous, driinking beer.  It took maybe 15-20 minutes for me to bring him off, but when i did i was rewarded with a fantastic load, every drop of which i swallowed.  When i finished and the Prof came down from his orgasm-high, Mitch said "I could use one of those."   The Prof instructed:  "Take care of Mitch for me, Josh."  i scrambled on my knees to between MItch's legs.  He pulled down his shorts revealing a better than average cock, but nothign spectacular like the Prof's.  Still, it was the Prof's friend's cock and i went to work on it.  MItch grabbed my head on both sides and started long-dicking my throat, moaning and talking trash all the time.  it didn't take him long, he was essentially masturbating using my throat rather than his hand.  He pulled out and shot his load all over my face and chest. 

 

i was turned on, and indeed a spot of precum had formed on the pouch of my royal blue thong.  Matt discovered it ."Hey Prof. Your bitch, has this disgusting spot of pre on his thong.  That's disgusting."  Matt apparently was not offended by Micths's cum all over my face and upper body.  But the Prof said, "Yeah, that looks kind of gross.  Take the thong off, Josh," he instructed.  "Give it to me."  So i took it off and started to use it to wipe the cum off my face.  "Leave that cum where it is," the Prof instructed.  "Give me the thong." So i did, and he threw it overboard.  For the rest of the journey, except when we were eating, i was completely naked, covered only by cum.

[phillyhank]

Hot story!  Please continue.

[seaguy]

And in cum pig heaven.

[Guest faggot hole]

Sailing -- Part 3:  It wasn't constant sex, as i had thought it was shaping up to be.  Obviously, it takes a lot of work to keep a boat like that going, on course, and afloat, and the crew actually was pretty busy just doing the stuff of sailing.  But every once in a while, one or two of them would take a break and come looking for me. 

 

But i'm getting ahead of myself.

 

One of the crew, the guy Matt, was a trained chef and he did all of the cooking.  The first night, when we were called to dinner, Matt onjected that i was naked at the dnner table.  "Disgusting.  And unsanitary."  He turned to the Prof.  "Do something about your bitch.  He's not eating at my table like that."  The Prof told me to put on the Japanese speedo that he had got for me, and i did.  Then Matt, and the others, complained that i looked ridiculous in that outfit, but they agreed that i'd look okay without the public hair, so after dinner they laid me out on the table and shaved me.  i was completely hairless below the eyelashes (and i stayed that way all the time i was "with" the Professor). 

 

It turned out that the aft stateroom was for me and for whomever was fucking me at the time, although the fucking did not take place exclusively below decks.  There was considerable fucking on the deck, and with me tied to one of the masts.  And the crew was as varied as four men could possibly be, with the one common denominator:  these guys LOVED to fuck -- and LOVED to have their cocks sucked (two common denomnators, i guess).  Jim our Captain was, as i have said, over six feet tall and a magnificent specimen of manhood.  Jim was married (to a woman) and was the CEO of a company that hed been in his wife's family for generations.  He was an aggressive fucker, highly physical and very verbal.  Jim didn't believe in foreplay.  No need, from his perspective.  i was there to take loads and get fucked, not to be seduced.

 

Matt, the chef, was shorter, around 5'9' or 10', but solid, muscular but not ripped.  Matt liked to have his cock lubed by my spit and throat slime before he fucked me and so sex with Matt involved a considerable amount of cocksucking on my part before he finally stuffed my pussy.  This was time consuming and frequently we had an audience of one or more of the other crew members waiting their turn at my cunt and razzing Matt to get on with it.  Also, Matt had tremendous endurance; he could fuck me for an hour, oblivious to the complaints of his waiting comrades, before finally nutting.  

 

Mitch was tall and skinny.  He looked like what i thought an accountant or office manager should look like.  But that frail body supported one of the largest, fattest cocks i had ever sees -- truly the dick of death,   I was absolutely shocked, and indeed scared, the first time i saw Mitch's tool.  But i guess guys with super-sized cocks learn how to feed it to a bottom, and Mitch was gentle and patient as he talked me through the process, like i had never taken a cock before.  

 

And the Professor, of course, was like a lover; gentle, firm, taking his time, yet truly dominant.

 

i think each of the guys unloaded at least twice, and more often three times a day during the 8 or 9 day journey.  As i said, we fucked pretty much everywhere a boy could be fucked on that boat.  The last fuck was on the aft deck, in broad daylight.  The prof was fucking my brains out as we sailed into port to the cheers, i must say, of the marina crew and the crew of the adjacent boats was Jim docked.

[iwannafux]

Wish I had a prof like that!

[sam_puppy]

I would love to read more

Edited August 26, 2015 by sam_puppy