JEFF'S BACHELOR VACATION Bill Drake (billdrake@hotmail.com)
FOR ADULTS ONLY. The following contains depictions of sexual acts between men. If this is inappropriate for your age or offends you, go no further. The story is fiction.
Thanks to those who've written in for past stories. If you like this one, feel free to send me a note: billdrake@hotmail.com.
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Jeff's Bachelor Vacation
Chapter 4
After a quiet, lazy morning, Jeff found himself looking forward to mid afternoon at the pool area bar. He should have felt sexually satisfied after the intense fucks Ed the Corporate Daddy threw him the day before. But the more sex he was having, the more he craved. If he was in a post-relationship hangover after the breakup with William, this was like the hair of the dog.
So after a nap, and a few hours reading a good book, Jeff showered up and put on his speedo, the one he wore the first day. Grabbed a towel and flip flops and headed down to the pool.
He was disappointed when he got there. No, Ed wasn't giving him the cold shoulder this time, but the young father was occupied with two hyperactive little girls in the kiddie pool. Apparently, family duties preoccupied him today. He saw Jeff and gave a quick, silent apologetic look. Jeff smiled back and shrugged his shoulders. Oh well, he could get a good swim in, work off some of the afternoon drinking he'd been doing. He'd normally been religious about his workouts, but the last two days had slowed that down.
So he got a real workout of a swim in. When he was done, he wasn't in the mood for a drink, not yet, and the afternoon sun still shone too brightly. Jeff didn't want a sunburn. He went back to his room to wash up and get dressed for dinner.
Evening meals were actually the worst part of this all-inclusive vacation. It was like being on a cruise without knowing anyone. That's why Jeff was surprised when he saw DILF Guy from the other day catch his attention and wave him over. After all the man was sitting at a table with his wife and another couple.
Nervously, Jeff walked over.
"Well if it isn't my happy hour buddy from the bar," he said like they were long lost college friends. "I didn't catch your name," he said
"Jeff," came the reply, and the 27 year old felt a little guilty for having slutted out like this, not even knowing the guy's name.
"Peter Mills," the confident man said, half standing out of his chair and grasping Jeff's hand in a firm handshake. "Why don't you join us, Jeff?" Unlike Ed, DILF Guy didn't seem shy or to need to hide anything. Though why should he? Jeff thought. These other people didn't know anything.
Jeff was surprised how quickly the conversation flowed. Mrs. Mills was an attractive woman, thin and poised, and it made the younger man feel a little bad he'd been responsible for the marital betrayal of Mr. Mills. But he had no idea what arrangement they had, if any. And it certainly wasn't the DILF's first time fooling around outside his marriage, Jeff surmised, based on the way he'd been so laid back about their earlier tryst.
At one point he saw the man smirk, almost secretly, then felt it. A foot nudge against his ankle underneath the ankle. Jeff smiled automatically, but passed it off as his reaction to the conversation he was having with the other husband. It didn't help that this man was smoking hot. A retired Army Captain, he had the fit muscular build bulked up from his age but honed from his recent deployment. His blond hair was still cropped military short with silver coming in at the temples, making Jeff guess he was in his mid 40s at least. Maybe 50, but if so the stud was aging really well.
As Mrs. Cantrell talked to the Mills, Jeff found himself more engrossed in conversation with Captain Cantrell, and every word the man said about Army life, or their three kids, or their small town in Indiana seemed like the most interesting thing ever, if only because they gave Jeff a chance to look into the military man's sea blue eyes and bask in the warmth of his smile and attention.
Jeff was taken a little off guard when the man asked him, "You like cigars, Jeff?"
"Um, never had one," he replied. He never particularly cared for the smell of them, and most of the guys he saw smoking them around Boston were major douchebags. But he had an intuition they were a passion of the Captain, so he left it at that.
The man had a gleam in his eye. "Feel like trying? Or at least giving me company while I enjoy mine? Kate can't stand me smoking anywhere around her."
He seemed so jovial and kid-like, Jeff found himself nodding in agreement, which got a big smile out of the man. "Honey, Jeff and I are gonna go outside and enjoy a smoke," he announced, standing up from the table and patting the sport coat pocket where he had a couple of cigars ready. "Ellen, Pete, excuse us."
"Sure thing, Steve," the DILF said with a conspiratorial look at Jeff. It was like he thought the Captain and Jeff were sneaking off to hook up, and while Jeff would have been happy with that, he knew he was just going out for a cigar and some more conversation.
The two found a secluded corner of the poolside bar, which was now empty during dinner hour, the blue glow from the pool lights casting a soft light all around. If anything, the lighting made the Captain that much more desirable. 6'2" and with a larger build than Jeff had initially realized, the Captain's size filled out his sport shirt and coat perfectly.
"Aw yeah," the Captain said, pulling out two cigars and running one under his nose, offering the other to Jeff. "Not all guys like cigars, but if you're gonna give them a try you might as well start with one of these beauties."
"Expensive?" Jeff asked on a hunch.
"You bet," the ex-military man said proudly. "Diamond Crown Maximus. About 20 bucks a pop and worth every penny." He put the tip in his mouth and pulled out his Army lighter. He practically purred as he sucked in the smoke. "Ah yeah, bud, been waiting all dinner for this."
Jeff copied his motion. The Captain watched in anticipation as he put his lighter up and light his new friend's cigar.
The smoke was acrid and the flavor strong but Jeff suppress his cough and did his best to hold in the redolent smoke. He wanted to impress the Captain. It took a minute but by the fifth puff or so he was starting to get used to the strong sweet-bitter flavor.
"Like it bud?" The Captain grinned around his own cigar, relishing the smoke.
"Surprisingly yes," Jeff admitted, now feeling butch as having mastered this masculine ritual and enjoying being brought into the company of this handsome, older man.
The Captain gave a light pat on Jeff's back, firm almost a slap. "Cool, I got me a new smoking buddy. You can keep me company the rest of the week," he growled.
"I don't want to waste your expensive cigars," Jeff replied, taking the cigar out and holding it to the side, aping the Captain. He was getting the hang of how often to inhale.
"If you're enjoying it, it's not a waste, Jeff," the man said. "Besides, cigars this good aren't meant to be enjoyed alone."
"Well, thanks, Steve." Then he added, "At least let me buy you a drink."
"I wouldn't object to that bud. A double bourbon, one ice cube."
The pool bar was closed so Jeff went inside and found a bar to get the drinks, a double bourbon for the Captain and a beer for himself.
"Cheers, bud. To new friendships."
"To new friendships," Jeff chimed in as they clinked glasses.
They talked, like old friends, until there was a lull in the conversation. The Captain seemed to be looking Jeff over. "You're the one right?" he asked in a straightforward manner. "The one who's real good at giving head. Steve told me about some dude who blew him yesterday, and I put two and two together."
Jeff felt guarded all of a sudden, but the Captain's next words put him at ease.
"Don't worry bud, it's cool. I'm just a little jealous, that's all."
"Jealous?" Jeff reacted. That was the last word he'd expected.
The Captain's large hand reached down and cupped his genitals, where a cock had already started firming up. He looked around and seeing no one, he grabbed Jeff's hand and brought to the hard bulge. Jeff couldn't tell the dick size exactly but knew it was real thick. He took a minute to explore the length before pulling back, afraid they'd be detected.
"I could use a talented mouth."
"I got a room," Jeff offered, and the Captain smiled.
They walked around the building toward the one where Jeff's room was, but all of a sudden the Captain gripped his wrist and stopped him. He gestured to a deserted alcove. "Here," he said softly. "I wanna be able to finish my cigar."
Jeff was nervous but he followed the handsome man and crouched down, a lump forming in his throat as he anticipated the Captain's cock. The man was neither rushed nor slow in unzipping and pulling out his dripping erection. It wasn't long, maybe a hair shy of six inches, but the Captain had a fat prick, genuine beer can size. Jeff wondered how he managed to fit that thick monster inside his wife or any pussy for that matter, it was just so wide.
It wasn't easy getting it into his mouth, for that matter. He had to stretch wide and loosen his jaw the best he could and take his time. Slowly inching the hard meat past his lips, past the tip of his tongue. The Captain's cock was sure delicious, though, salty and sweet from the precum and just a hint of manly musk. More pushed into him as the Captain took some initiative, pushing his hips forward to sink his meat into Jeff's cocksucking mouth.
He had to fight off a gag a couple of times, but Jeff did it. The Captain's hairy ball sac pressed against his chin as he sank the last millimeter inside. "Goddamn, you're good," the man said softly, running his fingers through Jeff's soft hair and enjoying his cigar. He held Jeff's head steady as he started pumping his hips, pushing the fat cock in and out of the younger man's mouth. Jeff wondered why he'd made a comment about wanting a talented cocksucker. When a dude takes charge fucking face like this, he doesn't need talent, just a receptive, willing mouth.
Those thrusts got faster, more insistent, making Jeff's tear up in his eyes. Then on one strong inward stroke, BLAM! Hot briny ex-officer seed flooding his mouth and throat. Jeff moaned excitedly as he swallowed and sucked down a third man's ejaculate on his bachelor vacation. If William could only see him now, he thought with a bit of spite and pride and sexual satisfaction. The Captain was ten times the man that William was.
And Jeff got the surprise of the night when he stood up and the Captain gave him a deep appreciative kiss as he tucked back in and zipped up. "That was awesome, bud."
Jeff felt embarrassed because his own wad was dripping down his hand. He'd come big time as the Captain used his throat.
The Captain pulled out a handkerchief, "here you go." Then giving Jeff a hearty look head to toe, he added. "You'd be the last guy I'd expect to do that, but damn you're the best. Pete talked you up, but didn't do you justice."
Jeff wiped up and made himself presentable again. The cigar had burned down. It was time to get back.
As they rejoined the others back in the dining area, Jeff thought he'd feel embarrassed or ashamed or something. But he just felt happy, really happy. He kept seeing DILF guy eye him across the table, trying to read if something was up. Maybe he was sending signals he wanted his bone drained, too. But eventually the Mills took their leave, calling it an evening. Then the Cantrells. Jeff was feeling buzzed from the evening's alcohol and tired from the sun, the swim, the sex and the long day and he wandered back to his room, whistling the whole way.
Jeff had barely started to fall asleep when he heard it. A gentle knock, then a more persistent one. DILF guy must want some of what his buddy got earlier, Jeff surmised and got up and walked across the room in the dark, opening the door.
A masculine presence suddenly entered the room, shutting the door quickly and wrapping his arms around Jeff's nude upper body. A hungry mouth latched on his, probing with a thick, insistent tongue. That aggressive kiss, so different from DILF guy or the Captain. Pure lust, no finesse. Strong hands gripped Jeff's briefs and pushed them down, appreciatively gripping Jeff's bubble butt cheeks with his fingers, kneading the muscle and zeroing in on the warmth of Jeff's crack. Eager, almost possessive.
"Sorry I couldn't get away earlier, man," the voice said. It was Ed the Corporate Daddy and all of a sudden Jeff relished the now familiar feel of his warm muscle and bulk and the obvious, insistent thick hard on pressing against Jeff's own crotch. "Been thinking all day about this."
He didn't seem to wait for Jeff to reply but instead walked the trimmer back into the room, toward the bed. He peeled off his T-shirt, and Jeff's body shook as he heard the sound of the zipper of Ed's shorts. Then their bodies reconnecting in the dark, Ed's warm muscle and girth bare and pressing into his own toned chest and abs, the man's club like cock dripping wet against Jeff's light stomach fur.
"Unf," Ed growled as he practically hoisted Jeff's body onto the mattress and immediately crawled up on top of him. Gone was the hestitant Ed, replaced by the take charge and horny Ed. He parted Jeff's strong legs and leaned down.
"Oh God!" Jeff cried out as he felt that thick, long tongue lick his exposed asshole. Corporate Daddy was actually eating him out! The sensations... the very idea of it... made Jeff's prick rock hard against his contracted abs. Ed's wife must be the recipient of some incredible pussy eating sessions, he thought, cause this man knows what he's doing. Incredibly, the top man kicked it up a notch, increasing the miniature drill-like stabs of his tongue against Jeff's pucker, which was now spasming and going wild. He wanted to get fucked and in the worst way.
It took Jeff a second to realize that Ed had stopped and was now leaning up, crawling between Jeff's splayed open legs and positioning himself over Jeff's supine body. Even in the darkness, Jeff new Corporate Daddy had a big proud smile on his face.
"You like that, buddy? I watched a gay video to see how you guys do it." Ed said. "Looked pretty wild but I wanted to try it."
"You're the best," Jeff breathed. "I'm serious, man."
"I thought it'd be gross," Ed admitted, "But I got turned on as fuck. Knowing I'm gonna be inside that tight hole."
"You leaking?" Jeff asked, running his hands freely on Ed's big body. Anticipating having this larger man pile drive him.
Ed laughed. "Dude, like crazy. I been thinking all day about doing you again." His voice sounded serious and lusty again.
"Try it without lube."
Ed's voice sounded even more turned on, if possible. "Seriously, man?"
"Yah. Rub your precum on my hole first and push in."
That's what Ed did. At another point, Jeff would have been scared at the intrusion for such a large dick without proper lubrication. But he was turned on as fuck. Somehow each sexual encounter of the week made him hungrier for the next.
Between the spit and pre-cum, the fit was tight but Ed's cock wedged inside the tightness of Jeff's hole. "Holy fuck!" the young Daddy gasped at the amazing sensations. "I'm not gonna last long buddy."
"Go for it," Jeff urged, wrapping his legs around the man's hips and butt. The first hard thrust made the eyes roll back in his head. Then the next. By the third, Jeff was moaning in excitement. Every shitty moment of the last year, the arguments with William, the loneliness after the break up, was getting fucked out of him. By some married dude who shouldn't be as good at this as he was.
Ed's mouth now reconnected with Jeff's. This man had taken to kissing, all right. A few more strokes and Jeff could sense Ed was near orgasm. The high whimpers, the rigidity of his upper body muscle, the impetuousness of his fuck thrusts. Then Ed came, loudly, and Jeff's guts received the heavy sperm deposit inside him.
Ed breathed heavily as they broke their kiss. "Whoa boy, that was awesome." He ran his hand along the side of Jeff's face, a surprisingly loving gesture and one that made Jeff's cock twitch. "I think I came a gallon in ya buddy," The big man added.
"I can feel it," Jeff said. "Feels great."
Then out of the blue, Ed's voice was softer. "So... is this what you and your boyfriend liked to do?"
It was a weird question to ask, but it made Jeff's heart race. "Um, yeah. But you're better at it."
Again, he could tell Ed was smiling. This was confirmed as the man reached over and found the bedside lamp. "There," he said as the room was illuminated. "I want to see you." Then slowly, he leaned forward for a kiss, slower this time.
Jeff still hadn't gotten off and his body quivered and his cock jerked in horniness. Ed was still buried in him and he couldn't help but hump his ass back and forth on the large phallus.
Ed realized and chuckled. "I left you high and dry, man. Sorry about that." His hands now ran appreciatively along Jeff's perfect torso. "I can go again. I swear you make me feel like I'm 19. Fucking all night."
The words excited Jeff but not as much as the hard inward shove of that cock. Corporate Daddy had some real power in those glutes. Ed looked down intently, watching the reaction on Jeff's face as he fucked harder and faster. "My buddy likes it hard, huh?" he said in a growl as he started going double time with his hips.
Jeff's hands gripped on to Ed's meaty chest, partly to admire it, partly to brace himself for the loss of control. One, then two, then six heavy shots of semen bursted from Jeff's dick, coating his chest as he nearly blacked out. When he came to, Ed's face was crunching into the telltale signs. "Oh, fuck, I'm gonna come again. Inside you, buddy. Oh fuck!" This ejaculation was smaller than the first, but Jeff was impressed at his new friend's sexual prowess.
They disconnected, and Ed ran his hands along Jeff's now spermy body. "I gotta get back, I'm afraid. I wish I could stay." What a difference a couple of days makes, Jeff thought.
"It's OK," Jeff said. He actually relished being alone and getting some well-deserved sleep.
The Corporate Daddy lifted his body up and stepped off the bed. "Mind if I rinse off? I don't want my wife to smell the sex on me."
Jeff nodded, too tired and fucked out to speak. His eyelids shut as he heard the water start. He was beginning to drift into slumber when he felt soft lips on his. A quick peck. He opened his eyes and saw Ed dressed again. Looking like a normal 30-something suburban dad, like dozens you'd see at this resort, only a hotter version. And that endearing smile on his face.
"Thanks buddy, you're the best. See you tomorrow."
"Yeah," Jeff managed a sleepy reply.
Ed turned off the lamp and a moment later the room door opened and shut and Jeff was alone, jizz dripping on his chest and sides and leaking out of his well-fucked hole. He'd wake up with all crusted in the evidence of their pairing but for now he didn't have the energy to do anything other than sleep.