Pete had set the tone. Gladly accepting the apparent no-dress code, David and JM followed and removed board shorts and tees, remaining in minimal Speedo bikinis. Everything was thus very European. After a few hours of sailing, a gourmet lunch (which had been provisioned by the marina hotel) was set out and eaten as they anchored near a small deserted island. But Pete decreed no alcohol. He was anticipating some heavy late-day sailing and wanted to be sure everyone was able to perform in heavy weather.
Fortunately, there were no storms that day and the perfect day sail ended around six. Pete invited the guys to enjoy sundowners on deck after they anchored. They talked and agreed that if Pete could find another boat, he could count on them for help. Obviously, Pete had found them to be compatible company. It turned out that Pete was a New York banker with a condo on the Lower West Side. This was their annual family vacation–and both his young boys would be in school within a few days. Phone numbers were exchanged. Pete also made it clear that he was bi, attracted to David and JM, and possibly ready for a non-family event later in the week. (He had been sporting a semi most of the day–and kept rearranging it within the small red pouch of his thong.)
David and JM were tired from the hot, bright sun and desperately needed restorative showers. They walked the short distance back to the B&B and decided to shower together. They were tired, but incredibly aroused by the near nudity of the entire day on the water–and Peter’s suggestive poses. Fortunately, the shower was large and designed for two–this was Key West after all. Soapy hands were soon caressing, pressing, squeezing, stroking, penetrating. Both cocks were at full attention. “I’m gonna do you JM.”
“Yeah, but then it’s my turn. We’re gonna flip tonight. I’m feeling a little like I want to pitch. I wanna do you. Pete sure set the tone.”
“If you’re a really good boy bottom, I might let you.”
The two young men semi-dried and headed for the king.
“Assume the position. I’m going to destroy that tanned ass of yours.”
“Yes sir.” JM already was into David’s occasional dominant attitude.
JM dropped his shoulders onto the mattress, grabbed a few pillows for support and pointed his muscled ass at David in submission. David approached, knelt behind him, and slapped the thighs farther apart. Then he trailed his lubed fingers along the hairless crevice, rimmed the twinkling pink opening, and inserted an index finger deep inside. JM moaned his pleasure in response. David squirted some flavored lube on the rim and inside. He worked the finger around, finding and then scraping the prostate. Then he dove in, pushing past the sphincter with his curled tongue while he latched his lips onto the rim and sucked as his hands grabbed JM’s hips to steady him. JM murmured out a string of obscenities and pushed back into David. “You’ve got the most talented tongue and lips on the planet. I love it when you eat me.”
“And you’ve got one of the tightest, tastiest boy cunts in Key
West–although I must say, that statement is without real research on my part.”
Soon David replaced his tongue with long fingers: first one, then two scissored, then three. He was big and girthy and the all-day denial had brought him to a peak level of stiffness and size. Finally, it was time. He positioned, grabbed JM’s hips, placed the dark head at the tunnel entrance, and pushed. JM took a deep breath and David popped in through the tight sphincter and froze. “God, I love having Davey inside me.” David reached under, collected some of JM’s precum and began to massage it into his dick. JM jolted with the sensitivity of the edging, and growled, sounding like a panther in heat. “You are so good, David. I’m ready. It’s time to drill.”
So David began his hip driven pile driving, hitting the prominent prostate with each stroke. JM squeezed and trapped David deep. So David stroked JM’s dick rapidly and pulled him into his lap as he sat back on his calves. One hand under the balls, the other stroking at speed. JM was helpless. He was too aroused. He could feel the sap rising in his pole, boiling out of his swollen balls. He was going to explode. And so he shouted out his eruption as David caught most in his fist. Then he rubbed some on JM’s chest, and pinched the swollen, sensitive nipples. Finally, in near torture, he massaged the cream into and palmed the sensitive head. JM responded with a deep gasp and a severe jerk. The super-pleasure was just too much. JM’s anal muscles suddenly contracted and David could feel himself being milked to a powerful series of spasms and blasts. Not quite simultaneous, but close enough. David fell on and trapped JM into a tight embrace and began licking his earlobes and neck.
“Mon Dieu, we’re good together. Just enough practice to know the e-zones, the timing, and the pleasure spots. I think I’m just about ready to take the next steps with you, David.”
“I’m tired. Let’s skip dinner and turn in early. But you probably need another quick shower.”
“That is not exactly what I meant. We can talk later. But remember, I get to be the big spoon. And I’m claiming my drilling rights later. I didn’t get the flop to your flip yet. This evening is not over.” JM got up, rinsed off in the shower and dried before crawling back into the bed.
David spooned into JM’s gut and wiggled his glute muscles into place. JM in turn raised David’s thigh and placed his semi-hard long snake between the thighs, poking the space just under David’s balls. JM reached around, fisted David’s cock and held him tightly against the dick head. “Go ahead and try to sleep now lover!”
David squeezed his thighs together, trapping JM. “Oh, babe, you are good. I can handle this position for a few minutes. What do you think of Peter? He’s definitely a dad that I’d like to fuck. And he may be around next fall when we are working the Street. He could be an interesting guy to know. He’s with a major hedge fund and specializes in acquisitions.”
“I’m going to leave him to you this trip. I’m looking to find a chicken. My goal this week is to take a cherry. This may be my last chance before we commit to exclusivity.”
“Good luck. This is Key West–there are no virgins within a hundred miles.”
“Oh, I think maybe I’ll find one. You can have the dads.”
“I’m okay with that–so long as they all look like Pete.”
Both guys dropped back on their pillows and eyes began to drop. David turned away and rested on his front, scissoring his right leg forward. But JM was not ready to sleep. He relaxed, then played with his phone until he heard David’s breathing begin to slow. He put the phone on the end table, turned toward David and smiled. Then he began one of his favorite patterns. He had hung back, waited and then pounced when his prey least expected, like a big cat. David was dozing, turned away. Suddenly, JM moved. He covered with his strong dark body, pushed David to the mattress and immediately began to use his lubed fingers in David’s fount of pleasure. Then he easily slid his dick into David just as David had reached that moment of almost sleep. David was rock hard within seconds; JM pumped from the side, long easy strokes which became steadily faster and deeper. David was quickly writhing in heat and pushing back into JM. Sleep was forgotten. He lofted his ass in welcome. But JM had other plans. “I want to see you, love. On your back.”