By: Unknown Author & Ryan Michaels
"I'm gonna fuck her one of these days," Sean said to Andy, something he said pretty much every day.
"Yeah, yeah, same old story. You're all talk. Why don't you put your money where your mouth is?"
"Fine, dude, what do you want to bet?"
"Twenty bucks you won't get in her pants."
"You're on."
"Ok, if you're so confident, let's say we up the ante and make it thirty bucks if you can get in her pants tonight."
"No problem," Sean grinned. "In fact, I'll bet you fifty that not only can I fuck her tonight if I try, but I'll also get her to get down on all fours and do her doggy style."
Andy burst out laughing. "You really think so, huh? Only thing you're gonna do tonight is your own right hand."
"Fifty bucks," Sean repeated.
"Ok, dude, it's a bet!"
The two lifeguards, standing in the shade of the guard chair, looked out at the subject of their conversation. Jenna, also a lifeguard, was belly-down on a surfboard, gliding around the kids' swimming area. A wet blond ponytail lay against her tanned back. The deep blue suit she was in both showed, and hid, enough of her taut physique to make her worth watching.
Both Sean and Andy had tried to find out first-hand what was underneath that suit. Both had been rebuffed, not unkindly, but firmly. The rebuffs hadn't done much to quell either their interest or their horniness. Both men were hot looking, and knew it, Sean in a blond-surfer-dude way and Andy in a tall-dark-and-handsome way, and each had gone on to glory with a good many women. Still, the unattainable had its attractions. The two men watched for a moment longer, and then Sean went up the ladder and into the chair.
"You watch," he said in a quiet voice. "Gonna get some relief tonight."
"Yeah, from jacking off," Andy laughed.
******
All three lifeguards were on duty until the swimming area closed at seven. It was a beautiful day, and it took the efforts of all three to evict the last few kids. It was almost seven thirty by the time the sandy shoreline was empty in both directions. The sun was no longer shining, but it was still light out.
Andy and Sean walked out of the men's showers twenty minutes later, each clad only in shorts and sandals. The conversation about how Sean was sure he could get Jenna had started up again as they were drying off and putting their shorts on.
"Besides," Andy was saying coming to a standstill just outside of the door to the men's showers. "How will I know if you got some? What, you think I will just take your word for it and hand over the cash?"
Sean laughed. "How about you watch us doing it?"
"I doubt I'll get an invitation, not that you're gonna either," Andy laughed.
"What if I do, though?"
"Well, in the highly unlikely event that you do, unless you're gonna try to fuck her outdoors or something, there's no way I'm gonna believe you without witnessing it," Andy laughed.
"Hey, outdoors, why not," Sean said. "The cove's usually deserted at night. I'll take her down there, and you can hide behind the rocks and watch."
"Dude, you're overconfident. If you go up to her and ask if you can fuck her, she's gonna slap your face."
"If I can get between her legs first, she can slap it all she wants." He glanced over at the exit from the women's showers. "Dude, here she comes. Get out of sight."
Andy ducked back into the men's shower entrance, and Sean went up to Jenna. Jenna was wearing a bikini top and shorts, and damn, she looked hot. Sean was more determined than ever to find out what was underneath those shorts.
"Hey, Jenna," he said as coolly as possible.
"Hey, Sean," she said. "What's up?"
"I was just wondering what you were gonna do tonight."
"No plans. Why?"
"I thought maybe you and I could take a walk down to the cove. Just talk, you know."
"Talk, yeah, right. Like you ever have just talking on your mind," she chuckled.
Sean grinned. "Look, Jenna, I can't help it. You're hot, and here we are together, day after day, and, well, I'd just really love to get to know you better… intimately."
Jenna looked away for a moment and smiled. "At least you're honest." Her voice dropped a step. "And I must say you're pretty hot yourself. It's not like I haven't thought about you... that way." She reached out and touched his chest with a cool index finger. The tip of her finger slid down, across his left nipple, and then her hand dropped to her side.
He shivered slightly and said, "You're just teasing me, aren't you?"
She looked up at him and then laughed. "Yeah, sorry, I couldn't resist. But I was planning to go for a walk along the shore before I went home anyway, so I guess we could walk to the cove together."
"Cool," Sean said. "Oh shit, I left my house keys in the men's showers. Hold on, I'll be right back." Sean then went over to the entrance and pulled Andy by the arm inside the room. "Dude, did you hear that?"
"Yeah, she agreed to go for a walk with you, big deal," Andy laughed.
"Yeah, well once I get her down to the cove, I know I'll be able to convince her," Sean said confidently. "You just make sure you get there right after we do, and don't let her see you."
"Sure thing, dude, whatever," Andy said.
Once Sean returned to Jenna they started to walk down the beach. The moon was up, and that was the only light, but it was enough to see by, and he hoped that Jenna couldn't see well enough to notice that he already had a raging hard-on. He knew that Andy didn't think he could get into Jenna's pants, but he was confident that he could, and would.
The cove, a rocky, secluded area known as a lover's haunt, was about a ten minute walk from the swimming area. Sean and Jenna didn't talk much, despite Sean's mention of conversation. They rounded the point and walked into the cove with its encircling rocks.
As they came to a stop Jenna turned to face him. "So, you said you wanted to go for a walk and talk, but you didn't say a word the entire way. You brought me here to try to get into my pants, didn't you?"
Sean wasn't sure if she was angry or flirting. "No… I, ah, well… yeah," he admitted.
Jenna took a step towards Sean, and for a moment he was expecting to get hit, but Jenna moved in and pressed her lips to his. Sean had been told before that he was a great kisser; he knew how to use his tongue. Her lips parted for it, wanted it; she needed it. Sean could feel, to his amazement, her body pressing against his, pushing against his erect cock. His hands slid down her bare back, and then, as his hands moved over her shorts, down the soft crease of her ass, she pulled away from his embrace, suddenly.
"What?" he asked breathing hard.
"You really want to fuck me, don't you?" she asked softly.
"Yeah!" he said. "Of course I do."
"Well, I haven't had sex in a while, and I'm actually considering letting you," she said.
"Cool," Sean said, stepping forward. "Let's do it!"
She put her hand in the middle of his bare chest. "Wait," she said. "I said I was thinking about it, but before I can decide there's something I want you to do for me first."
"What? Anything," Sean said excitedly.
"I'm glad to hear you say you'd do anything, because I have a secret fantasy. I want you to fulfill it for me, and then maybe you can fuck me."
"What is it?"
"I've always wanted to watch two guys together," she said.
"What?" Sean gaped at her. "You mean you want me to..."
"...go down on another guy," Jenna finished.
"But..." he swallowed, "You said if I helped you with your fantasy you might let me fuck you. You expect me to agree to do that with no guarantee that I will get to fuck you after?"
"If you'll suck off another guy, then I will let you fuck me."
"Suck another guy's cock? I don't know..."
"Ok," she said. "Then you can forget about getting with me tonight… or any night." She turned away from him and began to walk away.
He let her get a few steps away before calling out, "Wait!"
She turned and he jogged up to her as he thought Just tell her what she wants to hear so you can fuck her. Once you get in her pussy, you don't have to follow through with it.
"Look, I'm not saying I wouldn't do that for you, if I had to, to be with you," he started and then continued, "but there's no one here but us. So how about you let me fuck you right now, and then I'll do that for you just as soon as I can find a guy who would let me do that to him?"
"What about Andy?" she suggested.
"Andy?" Sean said questioningly. "I dunno if he'd be into doing something like that."
"Well, why don't you ask him and find out?"
"I will, I promise," Sean said.
"Great, let's find out now, shall we?"
"Now?" Sean said. "Well Andy would be home by now, and it would take too long for him to…"
Jenna turned toward the rocks and cut off Sean as she said, "Hey, Andy, show yourself."
"What are you doing? Andy's not here," Sean tried to cover.
"Uh huh," Jenna said. "Come on out Andy. The jig's up. I know you're there."
There was a moment, and then Andy stepped out from behind the curve of rocks. "I, uh, I can explain," Andy stammered.
"No need," Jenna said. "It's quite clear that you were hoping to get a porn show tonight while you stroked off back there. But, maybe we can do better than that."
Andy looked from Jenna's face to Sean's face and then back to Jenna's. "What do you mean?"
"I told Sean he could fuck me, but he had to suck off a guy first with me watching. And, since you're here hoping to watch him fuck me, I think you should be the one he sucks off… if you're a good enough friend to help your buddy get laid, that is."
Andy didn't answer for a moment and then said, "Can I watch you two doing it afterwards?"
"Dude, what are you saying?" Sean exclaimed.
"Sure," Jenna said to Andy.
"And you won't tell anyone what we did?"
"Dude!" Sean exclaimed again.
"I promise," Jenna said.
"Well…" Andy started but Sean interrupted him, determined to be heard this time.
"Hey, dude," Sean said, "I realize that maybe it's just a mouth on your cock to you, but do you realize that I'm the one who is gonna have to suck cock?"
"You're free to refuse," Jenna said. "Of course, you'll be stuck with a date with your hand tonight if you do."
"Fuck, I can live with that," Sean said.
"Well, ok, but I'm horny now," Jenna said, and then turned to Andy. "So, it looks like you're gonna be the lucky guy who gets to fuck me tonight, if you want to, that is."
"I'd love to fuck you!" Andy said.
"No, wait! Fuck! I'll… I'll do it," Sean said reluctantly. "And then I get to do you, right? You're not just gonna run off when we're... done?"
"If you suck Andy's cock in front of me, you can fuck me after, I promise."
"Ok," Sean said and took a deep breath. "Then let's do this and get it over with."
"You sure?" Andy asked.
"Yeah, I'm sure… that I don't wanna suck cock. But I also know for sure that I wanna fuck Jenna, so whip it out and let's get this done."
"Ok, dude," Andy said as he reached down and unsnapped and unzipped his shorts. "You better appreciate what I am willing to do for you just so you can get some pussy," he added as he pulled his shorts down.
What he's willing to do? Sean thought. I'm the one who has to put a dick in my mouth!
Sean may not have been at all fond of the idea, but what he didn't know was that Andy, like a lot of young guys, had had fantasies about other men, and that Sean had played a starring role in some of them. However, he had quickly come to realize that in his case they weren't just natural curiosities, but that he was indeed bisexual. So, he was actually excited by the idea of Sean sucking his cock for real, and because of this already had a major hard-on, which was easy to see now that he stood in just his boxer shorts. He slipped his hands inside the waist, pulled them down, and stood naked before his two onlookers.
Sean had seen Andy naked literally hundreds of times in the showers, but never like this, never with a hard-on. Sean was nervous, but the prospect of knowing what he was going to get afterwards took the edge off his fear.
"You too," Jenna said to Sean as soon as Andy was naked.
Sean turned. "What?"
"I want both of you naked."
"Shit," Sean grumbled, and then reached down and unsnapped and unzipped his own shorts and pulled them down. His own boxers followed. His hard-on stood up, rigid and slick, from his curly blond pubes. He was hard because of her and had remained hard since they first started walking, and he hoped and prayed she thought that he was horny for her, and not hard for his buddy's cock.
"Go ahead, go down on him," Jenna said.
Sean slowly, hesitantly, knelt in front of his friend. He just stared at the hard cock of his buddy that was now pointing at his face. He cringed a little and then moved his head forward. Just as his lips neared the big swollen head he cringed again and said, "I can't do this!"
"Yes you can, if you want to get your own cock in here," Jenna said.
Sean looked back over his shoulder to see that Jenna had removed her shorts and had slipped her fingers inside her bikini bottoms.
"Do it to him, and then you can slip that hard cock of yours right in here," she said as she stroked a finger along her covered slit.
Sean looked at her pussy longingly. He knew he had to have her pussy and knew what he had to do to get it. He also knew he would have to just force himself to put a cock in his mouth, so he turned his head around and just propelled his head forward and slipped his mouth over the head of Andy's penis. He'd never once thought about doing this, and he couldn't believe he was. He also didn't know how he was going to do it. He'd never thought of how big an erect cock actually was and how women managed to fit it in their mouths; and Andy was well-hung. The head by itself was a mouthful. How would he fit anymore in? He didn't know what else to do so he just suckled on the big head and stroked the underside with his tongue, scrunching his eyes shut so he wouldn't have to see it in his mouth.
Andy began to moan in response, and those moans increased in volume as his hips bucked and some of his cock slid into Sean's mouth.
Sean gagged, pulled back, and took his mouth away. "Andy," he said looking up at his friend.
"Yeah, dude," Andy said, breathing hard.
"Take it easy, ok? It's not like I've done this before, or even want to be doing it, so just let me do what I can do and don't try to ram it down my throat."
"Ok, sorry," Andy said.
"And, warn me, ok? You know, when you're gonna…" Sean couldn't bring himself to say the word.
"Yeah," Andy said. "I'll tell you, don't worry."
"I hope you are asking for a warning so you don't get surprised and choke or something," Jenna said.
"What?" Sean said looking over at her. "You said I had to suck a guy off in order to fuck you. You never said anything about swallowing his… stuff!"
"Well, you guys always expect the girl to swallow when she sucks your cock, so what's good for the goose is good for the gander," she said.
"I'm sucking cock for you, but I'm not fuckin' doing that!"
"Ok, have it your way," she said. "But if that's the case you may as well stop sucking him off now, because if you don't go all the way my fantasy won't be fulfilled… which means Andy will get to fuck me instead of you."
"Fuck!" Sean cursed, and then turned and lowered his mouth back onto Andy's dick. It's amazing what the power of the pussy will make a guy do! Sean thought as he began to work the head on Andy's cock.
Andy trembled and began to move his hips, trying to push more of his cock into his buddy's mouth. Sean gagged again and pulled off to warn Andy again not to try to shove it in his mouth, and then took the head back in once more.
Without even really trying, and without Andy pushing, Sean soon found more of Andy's cock in his mouth. He had somehow managed to take about half of it now and began moving his lips in the way a baby does when sucking on a pacifier, suckling on it. Andy's grunts became deeper as Sean tried moving his head up and down on the shaft, and Sean shocked himself at how easily he was now sucking on it.
Andy reached down and touched Sean's hair. "Yeah, dude, suck me," he said. "Suck it, suck it!"
Several minutes later Andy groaned, and his back arched. "Oh, god, get ready, I'm gonna cum, really soon!"
Yeah, which means I'm gonna have to swallow, really soon! Sean thought.
"Oh, god, here it comes, here it comes!" Andy cried out, and Sean closed his eyes tight again, and then the cum spurted out into Sean's mouth. He tried hard not to gag and puke as the bitter tasting liquid went in his mouth and he forced himself to swallow it down his throat.
To Sean, Andy's orgasm seemed to go on forever. It seemed like he would never be done. But, finally, the spurting liquid stopped, and Andy's cries turned to moans.
Sean removed the cock from his mouth and stood up right away. "Ok, time to hold up your end of the deal," he said, looking at Jenna as he wiped his mouth while scrunching his face, as he could still taste cum on his tongue.
She grinned. "Yes, you did what I asked, and a promise is a promise," she said as she undid her top, exposing her tits to the night air.
Sean went to her and caressed them, feeling her nipples hard underneath his fingertips. She was horny all right. She moaned softly. Evidently she really did get turned on watching two guys.
Pushing Sean's hands away from her tits, she stood and slid her bikini bottoms down and off. Sean's cock was so hard it ached, and it was dripping from his own fluids, getting wetter as he saw her now fully exposed, shaved pussy. He wouldn't last long, he knew, but he was going to get to put his dick inside Jenna's hot pussy, finally, so he didn't really care.
"What position do you like?" she asked.
"Doggy style," Sean said.
"You got it," she said, and then got down on all fours in the sand. She moved her knees apart and lifted her ass up to him.
Sean knelt between her spread legs. He reached down and grasped his own cock in his hand and maneuvered the head into place, pressing it against her wet pussy. Then he took her hips in his hands and thrust upwards.
Horniness took over. Usually he was a slow, methodical lover; tonight he was nothing but an animal longing to fuck and cum. She lifted one hand and began to play with her clit as he fucked her. He grunted with each deep thrust, and she moaned, desperately horny herself, fairly quickly nearing her own orgasm.
Standing, naked, watching his buddy fuck some pussy, Andy felt his cock stiffen again, and he reached down and began to jack himself off.
Soon Sean was ready to cum, and so was Jenna, and they came together. She lifted her ass higher and spread her legs wider as he thrust deeply and the spurting began.
Andy, watching, saw his friend's ass tighten, his head go back, and his back arch as his orgasm began. As Sean's orgasm slowed down, and Jenna's throbbing began to fade away, Andy cried out as he brought himself off again and his cum shot out onto the sand.
Sean leaned down, his belly pressing against Jenna's bare back, and whispered, "That was fucking amazing!"
She smiled and said, "You were pretty good yourself. I'm sure Andy would agree."
Sean blushed, and slid his cock out of her. "You're really not going to tell anyone what I did, you know, with Andy, are you?"
"Nope. But maybe we can all do it again. You think?"
Sean reached for his shorts. "You mean let Andy watch us have sex?"
"Yeah… after you suck his cock, of course," she smiled.
"I'm afraid that was a onetime only deal," Sean replied.
"Not if you want to fuck me again," Jenna said.
"Fuck… the power of the pussy," Sean grumbled as he pulled his shorts on.
Once he was dressed, rather than waiting for Jenna to get dressed, he walked away from the cove and sat on a rock a little ways away, his mind on what he had done with Andy, and whether or not he could bring himself to do it again to get some more of Jenna's pussy. And if it was even worth doing it again just to have her again.
Andy had stayed with Jenna, which Sean hadn't really even realized, his mind having been elsewhere when he had wandered off.
As soon as Sean was out of sight Jenna went to Andy, and placed a hand on his bare shoulder. He felt her cool breath at his ear. "I told you," she whispered. "I told you he would do it. You owe me fifty bucks."
Andy grinned. "Hey, no problem, you won fair and square. Not only did you manage to make my dreams into a reality by getting my best bud to suck my dick, but you managed to do it while making him believe that I'm straight. He still has no idea that I am bisexual."
Andy knew that he'd lose the bet to Sean when he'd made it, and have to pay him the fifty bucks. But, in his wildest dreams he never thought Jenna would be able to get Sean to suck his cock, and therefore she would have had to pay him fifty bucks and he would have broken even. Now he was out a hundred bucks – but it was worth it - and he didn't have that much cash on him. "I'll be able to pay you tomorrow," he said, and then had an idea. "Unless you want to go double or nothing?"
"What did you have in mind?" Jenna asked.
"I don't know… how about this: I bet you can't get him to let me suck his dick."
"Too easy," Jenna laughed. "I could get him to do that, no problem."
"Ok, so you want a real challenge, huh? How about I bet you double or nothing that you can't get him to fuck me," Andy said.
"Oh, now that does sound like an interesting bet," Jenna cooed. "You're on," she said and extended her hand and they shook on it.
******
"It's about time. What were you guys doing back there?" Sean asked as Andy and Jenna arrived at where he was sitting. "You weren't fucking were you?" he said sounding a bit jealous.
"Of course not," Jenna said. "We were just talking about the weekend."
"Oh," Sean said as he stood up and the three began walking. "What about the weekend?"
"Well it turns out neither of us have anything to do this weekend, so we decided we'd hang out together. Do you want to join us, or do you have plans already?" Jenna asked.
"No, no, I don't have any plans," Sean said perking up a bit. "I'd love to hang out… any chance I'll get to fuck you again?"
"Maybe," Jenna grinned. "That is, if you do something for me first."
"Of course, I figured there'd be a catch," Sean smiled, shaking his head. "Yeah, I'll do it," he said having made up his mind after thinking about how tight Jenna's pussy was and how good it had made his cock feel, that it was worth doing what he had done, again, just to get to fuck her even once more.
"Great, then it's a date," Jenna said.
Sean smiled at her and nodded.
"I can't wait for the weekend to get here so the fucking can begin!" Andy said.
"Me neither, buddy, me neither," Sean said as he slapped his buddy on the shoulder, his head filled with the thought of sticking his cock back in Jenna's tight pussy again.
Would Sean feel the same way when he found out it was Andy he'd have to fuck, first? Would he do it just to get his cock back in Jenna's pussy again? This was one double or nothing bet Andy was hoping to lose! It would be totally worth it, in the end… literally!
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