Last Fling

by Ben Boswell

  "Your wife is a great fuck," he slurred. "I wish I'd taken her to the prom!"

  It took me a second to sink in. "Prom? You have a college prom?"

  Tina was sitting beside me. She giggled. "Naw, we're seniors.... you know.... high school seniors."

  Jack actually spit out his beer at that, "Oh shit, we're goin' to jail."

  Tina giggled. "Naw, age of consent is 16 in Nevada. But we're all 18 anyway… well except for Chuckie the retard who was left back in middle school. He's 19." He looked up from fucking Leslie and gave Tina the finger.

  Jack shrugged at all of this and continued working his pecker into Jeannie's teen mouth. With his hand on the back of her head, he fucked her face forcefully. Jeannie may have been young, but she was experienced enough to take his huge cock. She even fondled his balls with one hand while stroking the exposed part of his shaft with the other. Jack closed his eyes and with a loud growl dropped what must have been a huge load into her mouth, because when he pulled out, it was running down her chin and onto her chest.

  Tim must have decided he was tired of waiting for Chuck to finish, so he kneeled down in front of Leslie. He grabbed a thick handful of her hair, lifted up her head, and pressed his cock into her mouth. For the next couple of minutes, Chuck and Tim hammered her roughly from both ends, until as if by design they both shuddered and came at the same time. They exchanged a couple of high fives and then turned to give me a big smirk.

  All those near-simultaneous climaxes created a natural break in the action. I went over to the other boat and helped Leslie get herself together then aided her as she unsteadily climbed back onto Jack's boat. She plopped herself down in the passenger seat, and watched the band finish up with a dazed look on her face. The kids had also had enough and they soon cast off. We finished off another round of beers and followed suit.

  Jack took the wheel on the way back across the lake, and Leslie and I both sat quietly. I, at least, was lost in thought. Things had definitely taken an unexpected turn or five. I was desperately, brutally jealous. My stomach was churning. I wanted to just grab Leslie. Shake her. Hit her. Yell. Something.

  But I was also paralyzed. I could have headed all this off at a half-dozen spots, and I hadn't. Hell, it was my idiotic willingness to take her to that fucking whorehouse that had, more than anything, set all of this in motion. But it was also the strip club and the lap dance and sitting at the blackjack table instead of taking her to the comedy show. From Leslie's perspective, I could see how she might think I was not only cool with all this, but actively encouraging it. Even on the boat, she'd seen me trying to feel up Jeannie and get a handy from Tina.

  But I was still angry. Yeah, we'd had a threesome and I got a handjob, and in the meantime she'd fucked one guy all night long, and then gotten gangbanged by a bunch of kids. She'd even given them her ass! Something I never got. Was this the real Leslie? A cheap slut willing to fuck any stranger with the guts make a move on her. Had she been doing this all along? I started replaying every event of our past eight years together, suddenly seeing dozens of events in a new light. Platonic friends became, in my mind, illicit lovers. Every girls’ night out a wild orgy. Business trips a cover for an affair with her boss.

  I shook the cobwebs out of my head. No, whatever had happened this weekend was just a blip. Sowing wild oats. A last fling. I knew that. I had to know it. To believe it. It was the only way to keep myself sane. I knew we'd have to talk it out… but not now… not yet.

  We got back to the marina and tied up the boat. As we got to the car, Jack tossed me the keys. "Hey bud, you mind driving? I'm beat. I'm gonna sit in the back and chill."

  "Sure man," I replied as amiably as I could.

  Leslie climbed in the front seat with me and we started to drive. She gave me a little smile and a massaged my neck. It felt good, and for a moment, it was just the two of us again, and I knew everything would be alright. I gave her a grin and squeezed her knee. We settled in for the ride back to Vegas.

  Jack dozed off as we set off, but after about twenty-five minutes he woke up. Leslie glanced back at him. "Hey, sleepyhead, feeling better?"

  "Sure thing honey, just got a little headache."

  "Aww, poor baby," she cooed. "Well, I know just the thing for that."

  Before I even realized what was happening, she had hopped into the backseat with him.

  He chuckled. "You’re a horny little thing, ain't you darlin’?"

  I adjusted the rearview mirror and saw that Leslie was stroking Jack's crotch through his jeans. My heart fell.

  Then Jack threw me a lifeline. "Baby, I think you're barking up the wrong tree. I doubt I have anything left."

  Leslie snorted. "You had enough for those whores!"

  "You're one to talk! How many dicks did you take on?"

  Leslie softened. "You're right. But those guys were just the minor leagues."

  "Come on," Leslie whined. "Get it up, and I'll make it worth you while."

  He chuckled. "I don't doubt that. You're a little spitfire. But what's the rush?"

  "Those boys stretched me out pretty good, and I wanna see if I can take you back there."

  I glanced into the rear view mirror in time to see my wife pull down Jack's zipper and fish out his thick prick. She stroked him roughly up and down.

  "You sure?"

  "Mmmm hmmm," she moaned as she leaned over and started wetly slobbering up and down his shaft.

  "We can try, but the only girlie's ever taken me that way was a Tijuana mama with more miles on her than a long haul trucker."

  "I like a challenge," she said with a giggle.

  She stripped off her bikini bottom and bunched her dress up around her waist. Then she climbed into his lap and impaled her pussy on his thick cock.

  "Oh fuck that's good," she groaned.

  "Yeah it is," he agreed. "Let's just keep doing this."

  "Nuh uh, I wanna try it." She looked over her shoulder and our eyes met in the rear view mirror. "Pass me the lotion from my bag, will you baby?"

  Her eyes were heavy lidded and glassy, the combination of pot, lack of sleep and horniness. But even still, there was something of my old Leslie in there. She seemed to pause for a moment, maybe reconsidering, I don't know, it was just a fleeting thing. Then he thrust deep again, and her eyes rolled into her head.

  She moaned and gasped at me, "hurry baby."

  I sighed and reached into the passenger seat, tossing her bag into the back. There was fumbling, the sounds of lotion squirting, and then Leslie groaning softly.

  I adjusted the rearview mirror. I looked back to see my wife riding Jack's cock while her middle finger churned slowly into her own ass.

  "Here let me help you with that," he grunted softly.

  She reached back with both hands and spread her ass cheeks wide. Jack squeezed a thick gob of lotion onto his fingers and then pressed both his index and middle finger into her bottom.

  She let out a shuddering growl, "Oh Jesus." But it was obvious from the way she was grinding into his groin that she loved it. I looked away, trying to focus on the road.

  After a few minutes, I heard him ask, "You wanna try it?"

  "Uh huh, but slow," she replied.

  I looked in the mirror again and saw her rise up, letting his big tool slide out of her pussy. She grabbed his cock and he palmed her ass cheeks, spreading them obscenely. Slowly, she rubbed the mushroom shaped head of his cock against her anus, up and down, up and down, until suddenly with a grunt, she pressed just the tip inside her.

  The car began to rattle violently. I looked up to see we were veering off the road. I swung the car to the left, over-correcting, then back to the right, again off the road, slamming into a pothole. Leslie screamed like a stuck pig. I swung left again, hitting another bump before finally regaling the road.

  "Watch where you're going!" she hissed. "He nearly split me in two!"

  I couldn't help it. I looked back again, sure enough her ass was now deeply impaled on his shaft, a
t least half of that thick tool wedged into her bottom.

  She was huffing and puffing like she'd sprinted a mile.

  Jack chuckled softly, pulling her close. "Just relax sweetie, at least it's mostly in now." He starting thrusting gently, pumping his big cock in and out of her ass.

  "Oh God," she sighed. "You're so fucking big. You make those boys on the boat seem like children."

  He laughed. "They were children."

  I groaned. Children or not, they were hung about as well as I was.

  "You know what I mean."

  "Do you like it?" He asked.

  "It hurts.... But yeah."

  They fucked like that for a while, each of them grunting softly.

  "I want the rest of it," she moaned.

  "Yeah?"

  "Yeah."

  I looked back again. He still had her cheeks spread wide, and now he was thrusting into her harder, deeper.

  "Oh... Fuck.... Ugh... God... Jesus... Fuck.... Jesus...." She grunted as each stroke came closer to filling her completely.

  And then suddenly with a triumphant squeal, she forced herself down those last inches, completely embedding his cock in her ass.

  "I did it, I did it," she gasped proudly.

  He chuckled. "Now make yourself come," he said with a moan. "I want to feel you come with my dick in your ass."

  She sighed. "I dunno if I can. It's... It's too much."

  He pressed her backwards, so that she was leaning away from him, still impaled on his cock, but now with her back arched, her head lolling back, inches away from mine.

  "Rub your clit," he commanded.

  "Okay, okay," she breathed softly.

  I turned my head and panned down her body. Her eyes were clenched shut, her mouth open and gasping, her tongue licking her lips. Her neck was red and splotchy, from the sun and Jack's kisses. Her breasts were thrusting toward the car's ceiling, her areolas puffy, nipples hard as erasers. Then down between her legs, I could see her snatch, pink and glistening, and below, just the base of his cock as it disappeared into her ass.

  She reached down and rubbed her pussy, two fingers finding and encircling her clit. She moaned loudly. Jack reached up and grabbed her breasts, squeezing them roughly, gripping her nipples and pulling them, stretching them as Leslie growled lustily.

  "Damn, you're a hot slut," he grunted.

  "Yes," she moaned.

  "Say it!"

  "I'm a hot slut."

  "Again."

  "I'm a hot slut. Oh God, I'm a hot slut," she hissed, her body suddenly beginning to spasm violently. "Oh fuck, oh fuck, that's good."

  He grunted and wrenched her toward him. Gripping her tightly, he thrust his cock raggedly into her ass.

  She squealed loudly over and over. "You're tearing me apart," she hissed.

  "Oh God," he grunted. "Fuck!"

  They both went still, panting as they caught their breath. He slowly eased his prick from her battered asshole. Leslie giggled.

  "What's so funny?" He asked.

  "I can't believe I did that."

  "Yeah?"

  "I'll be walking funny for a month."

  "Was it worth it?"

  She slowly lifted herself off him and curled up beside him. She looked up and our eyes met in the mirror.

  "I dunno," she replied softly.

  After a few minutes she dozed off, and when I looked into the back, I noticed Jack gazing quietly out the window, a happy grin on his face.

  IV

  We made the rest of the drive home in silence. My mind was racing, my stomach churning. We'd planned a "last fling," but what had happened was way more than I'd expected or wanted.

  I'd figured we would just drink and fuck, maybe some dirty dancing, basically the kind of stuff that had constituted “wild” when we’d first started dating. But the idea of buying each other lap dances and then a threesome with a whore was just something I'd never considered. And then Jack. And the boys on the boat. And Jack again. We'd gone from a "last fling" to a descent into madness.

  Worse, at each step, it was Leslie leading the way, pushing the envelope. I knew she was a sexual creature. I wouldn't have wanted to marry a woman who wasn't. But I never realized, never even contemplated, that she had this inside her. It was like I didn't know her. It scared me.

  At some level, I'd always assumed I was the degenerate one in the relationship, the one who'd suppress his crazy desires in order to have a happy, stable married life. But my intern and barrista fantasies suddenly seemed tame now that I realized that Leslie's thoughts, her fantasies, were raunchier and more extreme than I'd considered.

  Was there more? What was she planning for the rest of the trip? And when we got home, would this all go back under wraps? Or would she want to embrace swinging? Would I one day come home to find her fucking the gardener or gardeners, trying to see if she could take two cocks in her ass?

  It was dizzying, and it occurred to me that I just wouldn't be able to live that kind of life, live with the uncertainty that would come from knowing that inside my sweet, little Leslie was a "hot slut" just waiting to burst out.

  As we turned on the strip, I roused them both. Leslie pulled herself together just as we approached the valet. She was a little unsteady, but I let her start toward the entrance while I hung back with Jack for a moment.

  He shook my hand, and I shuddered slightly remembered the sight of his fingers plowing into my wife's ass.

  "So you want me to call you guys later?" He asked hopefully.

  I sighed. "I don't think so, Jack."

  "Oh... Okay." He paused. "We good? You and me?"

  "Yeah," I replied curtly.

  I tried to pull my hand away, but he held me firm. He leaned in close.

  "You want my advice?" He asked. Then not waiting for my answer he continued, "Don't over-think things. She's a great girl, and everyone had a little fun. It don't mean shit."

  I sighed and nodded. "That's easy for you to say," I muttered under breath as I pulled away.

  I caught up with Leslie and helped her to our room. She was wiped out, and she basically stumbled into bed and passed out again. I sat in an armchair and watched her for a while, but it had been a long, long day....

  ***

  I awoke to a bright sunrise exploding through our window. Leslie stirred when I started walking around.

  "Where's Jack?" She asked groggily.

  "Gone," I replied brusquely.

  She started to say something, paused, and then said finally, "That's probably a good idea. Things got a little out of hand, huh?"

  "A little?" I said tersely.

  She sat up and gave me a hard look. "You could have stopped it any time."

  "I could?"

  "What are you saying?"

  "I don’t know," I replied, looking down.

  "Yes, you do. You're saying something."

  I sighed. "Oh, come on Les. You were completely out of control. Those guys on the boat. And then in the car, what the fuck was that?"

  She stood up and padded over to me. "I thought we were just having fun, going with the flow."

  "It's scary. I didn't know you had that in you."

  "What, that I like sex?"

  "Sex is one thing. What you were doing is to sex like crack is to beer. It's like discovering I'm married to a porn star."

  She smiled. "A lot of men would like that."

  I shook my head. "No. A lot of men like the fantasy, not the reality of it."

  Her smile faded. "Okay, so what now?"

  "I don't know," I replied. Then after a pause, "Can I ask you a question?"

  She nodded.

  "How long?"

  "Huh?"

  "Well, you said something on the boat. That you'd done something like this before. And I just wondered."

  "Oh jeez, Dave, this isn't a good idea."

  "I need to know."

  She sighed and swallowed hard. "Okay, yeah, I was a little crazy before I met you. Drank too much, experimented.
You know, college."

  "Anal?"

  She nodded.

  "Girls?"

  She smiled.

  "Multiple guys?"

  "Sometimes."

  I shook my head. "And what, you've been like suppressing that all these years. Is that the real you?"

  She looked at me quizzically. "I don't know what..." She paused. "It's all the real me. I used to do crazy stuff, and then I grew up, settled down. It's what people do." She paused again and then in an exasperated tone added, "God, I just thought we were having fun."

  "Maybe you were."

  She rolled her eyes. "Oh yeah, the strip club, the threesome... Okay, so I got a little out of hand. I can make it up to you. Lets get gussied up tonight and see if we can pick up another girl to play, just the three of us."

  I shook my head. "No, Jesus, Leslie, you're not getting it. I want less craziness, not more. And the problem is that now that I know you have this inside you, I feel like I don't know you."

  She shook her head sadly. "Well, I don't know what to say. I'm sorry this experience turned sour for you, but I'm not going to apologize for things I did before I even met you, and I'm definitely not going to apologize for having desires and fantasies."

  "You don't find it, I dunno, degrading?"

  She snorted. "That's always it, isn't it? Anything out of the ordinary makes a woman a whore. Well, sorry, Dave, I'm not a whore and I'm not a victim." She looked me straight in the eye. "I like to screw. I always have. If there were no consequences, I'd probably do things that would make your head spin. Heck, I probably have. But there are consequences, I know that, which is why I've never, ever cheated on you. I just thought we were giving each other a free pass this weekend."

  "I never agreed to that."

  "Yes, you did. You did when you put your dick in that whore's mouth."

  "Oh really? You might have explained the quid pro quo."

  "Oh please. You knew. You knew when you let Jack pick me up.”

  “I didn’t realize what was happening. You could have made that more clear.”

  She chuckled. “The only way I could have made it more clear would have been to announce that Jack wanted to fuck me out loud at the blackjack table. Would that have been better?”