Greg, Jeff, Brett and Hank all went in on a syndicate to buy a racing sailboat after their divorces were final. It made the financial burden easier, and always ensured there was a crew for the races. It was about 30’ long, with a small cabin just about right for two people, with a small, triangular-shaped bed in a tiny cabin in the bow.
Greg is your total linebacker type – big, beefy, blonde, hairy, quite a lot like the guy in the “Your Dad Wasn’t A Metrosexual” Canadian Club ads. Jeff & Brett get teased all the time about being brothers. They don’t look all that much alike, but they have the same average frame, short wavy brown hair and wire-framed glasses. Post-divorces, they also both appear to be bi these days. Hank is the classic Southern Italian stocky bear, with wolfish gray/blue eyes, and a face that perpetually needs a shave.
For the race out to the Farallons and back, Greg announced that he was bringing, “…a bottle of Jack Daniels, a bucket of Kentucky Fried Chicken, and a hooker.” Yeah right, but sure enough if he didn’t come striding down the dock, in that rangy, rolling sailor’s gate of his with all three. The hooker’s name was Steffi, and she actually seemed nice, and not skanky at all. She settled in up in the front cabin with her bag and a book. “Come down whenever you want,” she said airily.
“So what’s this little adventure going to costs us?” I asked Greg. “Well, with tip it works out to about $150 each. She’ll do anything we ask her to, but we only get to fuck her 10 times total between the four of us. So I figure we’ll pro-rate it that way once we get back.”
We got the boat ready, left the marina, and joined the small flotilla of sailboats heading out the Golden Gate. About an hour into the race, Greg announced, “Okay boys, I’m in.” He went down into the cabin, and with his back to us, stripped off his t-shirt, and kicked off his sandals and cargo shorts. He thumbed down his white jockey shorts and walked ahead into the cabin. You could almost sense more than see his big, thick penis swaying in the air in front of him. He ducked into the cabin and pulled the curtain closed behind him.
Steffi’s eyes widened. “Your picture doesn’t do you justice,” she purred. “You’re one really well endowed man.” “Yeah, and I’m one really horny, well-endowed man,” Greg replied, “Let’s get the party started!” She opened her legs and gave a little wave of encouragement – as if he needed it. In the cramped, small space, he crawled between her legs, with his huge, swollen erection bouncing back and forth against her thighs. He grabbed the top of his huge shaft with one hand, with his index finger sticking out, and pushed his finger inside her, with his cock following right behind. He slipped in easily until he was about halfway in and then she grimaced, “Hold on a moment baby, give me a little time.” So Greg rocked back and forth, in and out, gently and slowly easing more of his prodigious length inside of her. Eventually, with one last gasp from her and one more groan from him, he was buried inside her. At this point, with the process of penetration behind them, they began to fuck. And how. Her feet were braced up against the low ceiling of the cabin, and he thrust himself in and out of her with long, deep, plunging strokes of his big, red 9” cock. The motion of the boat rocking in the waves only added to their heightened pleasure. After about 10 minutes, his breath started to come in gasps. She reached down between his thickly forested legs and squeezed his congested, stone-like testicles. “Hold on baby, wait for me,” she whispered. “Can’t. So fuckin’ horny, gonna blow,” Greg gasped. His thrusts became faster, even frenzied, and a low growl began deep in his throat. Incredibly, Steffi felt his penis get even longer and thicker as his orgasm swept over him, and he roared like a bull as rope after thick, squirting rope of his semen poured deep inside her.
After a moment to get their breath back, he rolled to one side and in long, slow, delicious motion, his still-erect penis slid out of her, ending with a small, wet plop that made them giggle. His sperm was everywhere, on the bed, in their pubic hair, on their bellies. “Wow, I’ll be getting more of that today, won’t I?”Steffi asked? “You betcha,” Greg said with a lazy grin as he got up and came out into the cabin.
The three other guys were in the cockpit applauding when he came out. His penis was now flaccid, but still very long and thick, an angry purplish-red, glistening with his and Steffi's juices. He grabbed the base and twirled it at the guys helicopter style. He grabbed a cloth from the galley, and wrapped his penis in it, rolling it from side to side to dry himself off, then dabbing at the copious amounts of semen on his legs and belly and pubic hair. Then, he tugged on his jockey shorts, still obscenely swollen and stretched by his big genitals, threw on the rest of his clothes and sauntered up on deck.
He collapsed in the corner and grabbed a Heineken out of the cooler. All expansive and last-name basis now, he turned to Jeff and Brett and said, “Okay, Costerman and Ettore. Does one of ya wanna go jump that shit, or you just gonna homo yourselves off all day?”
More to come shortly. Everybody gets off at least twice before the day is through.
Greg is your total linebacker type – big, beefy, blonde, hairy, quite a lot like the guy in the “Your Dad Wasn’t A Metrosexual” Canadian Club ads. Jeff & Brett get teased all the time about being brothers. They don’t look all that much alike, but they have the same average frame, short wavy brown hair and wire-framed glasses. Post-divorces, they also both appear to be bi these days. Hank is the classic Southern Italian stocky bear, with wolfish gray/blue eyes, and a face that perpetually needs a shave.
For the race out to the Farallons and back, Greg announced that he was bringing, “…a bottle of Jack Daniels, a bucket of Kentucky Fried Chicken, and a hooker.” Yeah right, but sure enough if he didn’t come striding down the dock, in that rangy, rolling sailor’s gate of his with all three. The hooker’s name was Steffi, and she actually seemed nice, and not skanky at all. She settled in up in the front cabin with her bag and a book. “Come down whenever you want,” she said airily.
“So what’s this little adventure going to costs us?” I asked Greg. “Well, with tip it works out to about $150 each. She’ll do anything we ask her to, but we only get to fuck her 10 times total between the four of us. So I figure we’ll pro-rate it that way once we get back.”
We got the boat ready, left the marina, and joined the small flotilla of sailboats heading out the Golden Gate. About an hour into the race, Greg announced, “Okay boys, I’m in.” He went down into the cabin, and with his back to us, stripped off his t-shirt, and kicked off his sandals and cargo shorts. He thumbed down his white jockey shorts and walked ahead into the cabin. You could almost sense more than see his big, thick penis swaying in the air in front of him. He ducked into the cabin and pulled the curtain closed behind him.
Steffi’s eyes widened. “Your picture doesn’t do you justice,” she purred. “You’re one really well endowed man.” “Yeah, and I’m one really horny, well-endowed man,” Greg replied, “Let’s get the party started!” She opened her legs and gave a little wave of encouragement – as if he needed it. In the cramped, small space, he crawled between her legs, with his huge, swollen erection bouncing back and forth against her thighs. He grabbed the top of his huge shaft with one hand, with his index finger sticking out, and pushed his finger inside her, with his cock following right behind. He slipped in easily until he was about halfway in and then she grimaced, “Hold on a moment baby, give me a little time.” So Greg rocked back and forth, in and out, gently and slowly easing more of his prodigious length inside of her. Eventually, with one last gasp from her and one more groan from him, he was buried inside her. At this point, with the process of penetration behind them, they began to fuck. And how. Her feet were braced up against the low ceiling of the cabin, and he thrust himself in and out of her with long, deep, plunging strokes of his big, red 9” cock. The motion of the boat rocking in the waves only added to their heightened pleasure. After about 10 minutes, his breath started to come in gasps. She reached down between his thickly forested legs and squeezed his congested, stone-like testicles. “Hold on baby, wait for me,” she whispered. “Can’t. So fuckin’ horny, gonna blow,” Greg gasped. His thrusts became faster, even frenzied, and a low growl began deep in his throat. Incredibly, Steffi felt his penis get even longer and thicker as his orgasm swept over him, and he roared like a bull as rope after thick, squirting rope of his semen poured deep inside her.
After a moment to get their breath back, he rolled to one side and in long, slow, delicious motion, his still-erect penis slid out of her, ending with a small, wet plop that made them giggle. His sperm was everywhere, on the bed, in their pubic hair, on their bellies. “Wow, I’ll be getting more of that today, won’t I?”Steffi asked? “You betcha,” Greg said with a lazy grin as he got up and came out into the cabin.
The three other guys were in the cockpit applauding when he came out. His penis was now flaccid, but still very long and thick, an angry purplish-red, glistening with his and Steffi's juices. He grabbed the base and twirled it at the guys helicopter style. He grabbed a cloth from the galley, and wrapped his penis in it, rolling it from side to side to dry himself off, then dabbing at the copious amounts of semen on his legs and belly and pubic hair. Then, he tugged on his jockey shorts, still obscenely swollen and stretched by his big genitals, threw on the rest of his clothes and sauntered up on deck.
He collapsed in the corner and grabbed a Heineken out of the cooler. All expansive and last-name basis now, he turned to Jeff and Brett and said, “Okay, Costerman and Ettore. Does one of ya wanna go jump that shit, or you just gonna homo yourselves off all day?”
More to come shortly. Everybody gets off at least twice before the day is through.