Last Fling

by Ben Boswell

  It came as a shock. For a woman who’d never been with a girl before, my wife was surprisingly comfortable with it. I probably should have thought more about that, but then they came over to me. Leslie pulled down my pants and Elena slipped a rubber on my prick. The girls took turns licking my dick, stopping occasionally to kiss wetly. They worked well as a team, passing my cock between them with what seemed like practiced ease.

  After a while, Leslie took my hand and the three of us climbed on the bed. Leslie pushed me onto my back and climbed aboard. She slowly made love to me while Elena kissed between us, going from Leslie's nipples to mine. A few minutes passed and Leslie slowly lifted herself off me, sliding up until her wet, trimmed pussy was at my face. I buried my tongue inside her sloppy-wet snatch, eliciting a loud growl. At the same time, Elena straddled my hips and impaled herself on me. When Leslie saw what was happening, she climbed off.

  She whispered in my ear, "I want to watch you inside her."

  Leslie slid down for a better view, her face now inches from my dick as it disappeared into Elena's pussy. Elena rode me slowly, expertly, and when she lifted up off me, she encouraged my wife to suck my dick, now covered with Elena's juices. I didn't want to turn Leslie off, so instead I flipped Elena onto her back and proceeded to bang her harder. Leslie lay down beside me.

  She licked my ear lobes and then whispered, "Yeah, fuck her. Fuck her hard."

  We switched around another couple of positions. The most memorable was the way we finished, with me taking Elena from behind while she licked Leslie to a screaming orgasm. I came what felt like a gallon.

  But as memorable as it was, the fantasy, or maybe even the retelling, are more exciting than the reality. At the time, I can remember noticing that Elena looked worn beyond her years, and I couldn't help but wondering how many other guys had been where we were even that evening. Her room was shabby around the edges, like an aging motel room. Plus, since Leslie had been on the pill since college, I wasn't used to the sensation (or lack thereof) of wearing a rubber. And because it was approaching 4:00am, I was tired and my buzz was turning into the beginnings of a hangover. Enjoying the whole experience was more work than it should have been.

  We got dressed and straightened up. As the cab drove back to the hotel, we could see the sun starting to peek over the mountains to the East. Leslie dozed off on the ride, so we didn't talk much. And at the hotel, we just sleepwalked to our room and collapsed onto the bed.

  II

  I woke up around 10:00am, with a nasty headache, and the terrible feeling that Leslie would probably be horribly upset when she awoke and remembered the previous night's events. I took a long, long, hot shower. But when I got out, I was pleased and surprised to find Leslie awake, with a room service breakfast on the way, and a smile on her lips despite the somewhat haggard look in her eyes. We munched on a light meal, drank some much-needed coffee.

  “That was some night,” Leslie noted.

  “I’m sorry. Things got out of hand.”

  She gave me a curious look. “Having regrets?”

  “Yes.”

  “Really?”

  I wasn’t sure how to answer. She didn’t seem angry. Was this a trap? That wasn’t Leslie’s style. But then again, little of what had happened last night was Leslie’s style as I knew it at least.

  “I don’t want screw things up between us.”

  “Well, we certainly screwed things up last night,” she replied with a grin.

  “You know what I mean.”

  “Right, but, well, I thought this was a last fling. A last chance to get a little crazy.”

  “Sure, but we’re not that crazy to begin with. This is more like a first fling.”

  “Oh, come on, we’ve gotten silly in the past.”

  “I am pretty sure a threesome with a prostitute is different in kind from dry humping in a night club.”

  “Or skinny dipping in Hippy Hollow?”

  “That was just us, though.”

  She raised an eyebrow at me.

  “Well, besides the other nudists and the Peeping Toms,” I admitted. “But you know what I mean.”

  “Well, I had fun last night,” she insisted. “And I know you did too. And, what happens in Vegas, stays in Vegas.

  I raised my coffee mug. “What happens in Vegas, stays in Vegas.”

  We clinked the coffee. She went off to take a shower, while I sat back, finishing my cup, watching Sports Center on TV and thinking about what a cool wife I had.

  ***

  We were moving pretty slowly that day. We managed to make it across the street to Caesar's to browse the shops and admire the recreation of the Roman forum. Leslie picked up a pair of shoes and a couple of silk scarves. We had a light lunch and then went back to our hotel room for a well-deserved nap.

  It was nearly 6:00pm when we woke up, somewhat refreshed, but still in agreement that a relatively quiet evening would do us good. We had an early dinner, and then I wanted to hit the tables for my first time on the trip. Leslie joined me for a while, but disappeared after an hour to explore the hotel and entertainment options.

  I had started off really hot and was up over $1200 almost right away, but unfortunately, I lost a couple of big hands. I kept saying to myself that if I could just get back to $1000 up, I'd walk away, but instead I seemed to be trapped in an endless cycle of win-one-lose-one that had me falling further and further from my goal.

  Still, I was having fun. We had a good table. Gladys, a retiree from Florida, was at the far left, puffing on cigarettes and drinking scotch and sodas. It was funny seeing her snort at the beginners who kept joining the table, making dumb bets and walking away down $200 in 5 minutes. To my right was Jack, a slender Texan with a bushy mustache, bolo tie, and a ten-gallon cowboy hat. Mid-forties, handsome in a weather-beaten way. He was a hoot, really playing up his straight-out-of-central-casting persona. The cocktail waitress was “darlin’,” the dealer, “partner.” He was a regular. The pitbosses knew him and came around and periodically joked with him.

  Leslie returned around 11:00pm.

  "How's the table doing?" she asked.

  Jack gave her big smile, "It suddenly got a lot better."

  She smiled back, and then leaned over and kissed me on the cheek.

  Jack guffawed. "Well, damn, son, you may not have a lot of luck at cards, but you sure seem lucky at love."

  I introduced them. Leslie reached out to shake his hand, and he took it and kissed her hand. She giggled.

  "So, anything going on?" I asked.

  "Naw, just a couple of crappy bands playing the lounges. I was hoping to get tickets to the comedy show at midnight, but they're sold out."

  "Well, that's okay," I replied. "I don't want to walk away quite yet. I think my luck is turning." I was on a short winning streak that had gotten me back to even from over $500 down.

  She yawned. "Yeah, well I'll probably turn in soon anyway."

  At that point, Jack jumped in. "Hey, if you want to see the show, I've got an extra ticket. Won it at the seven o'clock drawin'."

  Leslie perked up. "Yeah?"

  "I was just gonna use the extra seat for my hat, but you're welcome to it. You can have the other if ya want," he said to me.

  I shook my head no. "I think I'll stick it out here." I turned to my wife, "You want to go with Jack?"

  She raised her eyebrow at me and then smiled. "Sure, why not. Meet you back in the room?"

  "Naw," I replied, "check back here first. I'll be the guy with the huge pile of chips in front of him by then."

  She kissed me on the cheek and then she and Jack went off to the comedy club.

  My winning streak continued long enough to get me up $800, but then I hit a terrible run. Dealer kept pulling fives on sixteens, I'd split aces and get dealt a pair of threes on them. By the time Leslie came back around 1:15am, I was down over $2000. My luck had to turn.

  She was real tipsy and giggly. She leaned in close and whispered in my ear, "So are you comin
g to bed with me? Or should I make other plans?"

  She didn’t seem tired anymore.

  "Just give me a few minutes," I said distractedly as the dealer dealt another hand. "I'll be right there."

  “You sure, baby? Some of those comics were pretty raunchy. I have some crazy thoughts in my head.”

  The dealer dealt the next round. Blackjack! There was no way I could leave now.

  I looked over my shoulder and saw Jack standing a few yards away.

  “You should buy Jack a drink,” I suggested. “You know, to pay him back for the comedy club.”

  She gave me an impish grin. “I’ve already had more than a few. Who knows what might happen if I have more.”

  The dealer had started the next hand. I got an eight and three, and the dealer had a five showing. My luck was definitely changing.

  “I’ll meet you guys at the lounge in a bit. Go ahead,” I muttered distractedly.

  I didn't even watch her leave. Things had finally turned my way. Not enough to get back to even, but I won enough hands to be able to leave the table with a modicum of pride, even if I was still down $1200 for the night. I looked at my watch and realized it was now past 2:30am. More than the few minutes I’d said, but I figured Leslie would forgive me.

  I went to the lounge. A very bored looking band was playing 80s covers to an even more bored looking group of patrons. No Leslie though. Drat. I hoped she wasn’t upset after all.

  I hurried up to the room. I put the keycard in the door and pushed it open.

  I heard them right away, but it didn't register at first. I remember wondering what Leslie was doing watching porn this late at night. Then I stepped into the bedroom. Leslie was naked, on her back, her legs draped over Jack's shoulders. He was standing at the foot of the bed, clad only in his black socks and cowboy hat, pistoning his cock into my wife. Whether from shock or exhaustion, for a while, I could only stand there watching. They'd been at it for a while, that was clear. Leslie was moaning and groaning through breathless gasps. Jack had rivers of sweat rolling down his cheeks onto his chest. At one point, he pulled out and several times lightly slapped Leslie's snatch with his bare member. For the first time I noticed how hung he was, his cock seemed to be the size of one of those "tall boy" beer cans. He then plunged back into her, making Leslie throw her head back in passion and growl, "Ohhh, fuck yeah!"

  I snapped out of my trance. "What the fuck is going on?" I demanded.

  Leslie looked over at me. "Oh God, Dave, did you see his cock?"

  Jack shot me a big grin, "I bet her $100 she couldn't see my pecker and not end up in bed with me."

  Leslie giggled. "You owe Jack a hundred bucks!"

  She grabbed his hands in hers and slung her hips against his groin. "Oh baby, oh baby," he moaned, accelerating his own movements.

  "Give it to me!" she hissed.

  That seemed to push him over the edge. He let out a loud yowl and his knees seemed to buckle slightly. He slowly pumped her for another few moments, and then with a sigh let his thick, wet dick slide out of my spouse's pussy.

  "Oh wow, that was amazing," she gushed. She sat up and looked over at me. "Not as good as Dave, of course," she said with a wink, "but wow!"

  He just gave her an exaggerated 'aw shucks' grin in response.

  She stood up and gave Jack a big, wet kiss and then walked over and gave me a peck on the cheek. "I'm going to get cleaned up and be right back," she said as she ambled to the bathroom.

  Jack sat on the bed and pulled on his boxers. He looked up at me with a cautious smile. "Hey buddy, no hard feelings, right? Normally, I'd never make a pass at a married lady, but after she told me about your adventures last night, I figured you'd be cool with it. Maybe even like it?"

  I sort of stammered something noncommittal, and he seemed to get the point.

  "Well, I better be going," he said, standing up and reaching for his pants.

  Just then Leslie re-entered the room.

  "Oh no you don't," she said gaily. "I'm not done with you... or with this," she said as she reached into Jack's boxers and stroked his member.

  "Honey, you done tuckered me out," he drawled.

  "Well, then you're just going have to stay the night and rest up so you can finish what you started," she answered.

  He shrugged and let her pull him back over to the bed.

  "You just rest up and let me take care of everything," she cooed.

  He lied back and closed his eyes as Leslie pulled his boxers back off. She started stroking his cock firmly while she starting kissing and sucking on his nipples.

  Jack let out a gurgling moan, "Oh baby, you are good at this."

  Leslie looked up at me. "Join us, baby."

  I hesitated. "Naw, honey, I'm really beat. Maybe later," I replied lamely, hoping she'd take the hint and send Jack on his way.

  She looked back and forth from me to Jack cock and then sort of shrugged, "Ok, baby, the door's open." Then she leaned down and began licking his shaft.

  I stumbled out of the room and collapsed onto the sofa feeling despondent. My hope that being out of room would insulate me turned out to be misguided. I could clearly hear them in the next room, although I did manage to doze off for part of the night. I don't know how many times they did it. I know it was at least two because I had to walk past them to go to the bathroom twice, and each time they were at it.

  The first time, Leslie was riding Jack, her eyes closed as she slowly rose and fell on his big shaft. Her hands were on his chest, allowing her to remain steady as she rose up, higher and higher, until his huge cock was just barely inside her before impaling herself roughly back onto his cock. There was a disturbing single-mindedness to her performance, as if there were nothing else in the world other than the sensation of his fat prick filling her again and again.

  His hands explored her body casually, pinching her hard nipples, squeezing her firm ass. She bit down on her lip, shivering as she climaxing, but even then she didn’t stop. She continued to ride him, faster and faster, as if determined to milk every last drop of pleasure out of him even as she sought to drain him of every last drop of jism. I didn’t stay to watch the end, and Leslie didn’t even seem to notice me, though Jack did give me a wink as I slinked by on my way back out to the living room.

  When I awoke again needing to pee around six in the morning, I was torn. I knew they were fucking again. Hard, to judge from my wife’s squeals of passion. I could have held it, but part of me, I guess needed to see what was going on. He was between her legs, really laying pipe, making a mockery of the notion that missionary means staid. But it was Leslie who had me mesmerized. She was gasping and thrashing, squealing like a woman possessed. They say size doesn’t matter, and maybe he had mastered some hidden technique that I was I couldn’t observe, but from what I could see he was just pounding her hard, and his huge prick was driving her mad with passion.

  ***

  I woke up to the sound of voices. Jack was coming out of the shower with a towel around his waist, and Leslie was ordering breakfast from room service. She had a hotel robe draped over her shoulders, but it was open in the front, exposing basically everything, the valley between her pert breasts, the flat of her stomach, her closely trimmed muff. Despite what I had witnessed the night before, her casual nudity around him felt like a kick in the stomach. She was comfortable with him, not embarrassed and regretful.

  Jack was all smiles. "Man, what a night!" he exclaimed. "Won big at blackjack, and then I got lucky!"

  Leslie giggled.

  "Hey, I owe you guys," he continued. "Listen, I've got a powerboat out on Lake Mead. What say you guys join me on the water for the day. Get a little sun, have some beers. It's beautiful."

  "That would be great," Leslie exclaimed quickly. Then she looked over at me, "can we go?"

  I realized that after our first night's activities, I would look like a total ass if I showed how jealous I was. And anyway, out on the water seemed a better option than spending the day
in the hotel room. From the way her robe hung open, I was pretty sure that breakfast would quickly segue into another round of Jack fucking my wife with his oversized tool if we stayed indoors.

  I nodded. "Sure, honey, it'll be fun."

  Leslie and I ate some breakfast and then showered.

  She’d slipped on a sheer, flowered sundress over her bikini. She was in a good mood, wearing the sort of giddy smile you only get from a night of really good sex. Or at least that’s how I read it. She seemed to notice I wasn’t in quite such a good mood.

  “You okay, Dave?” she asked.

  She was packing up sunscreen and a paperback.

  “Yeah,” I muttered.

  “I wish you’d joined us.”

  “You didn’t seem to need me,” I replied dourly.

  She grinned involuntarily as she reflected her time with Jack. “True enough, but it would have been even more fun with you involved. It’s weird seeing your spouse with another person, right?”

  I nodded. Fuck. She had me. She’d given me a threesome, and now I just had to suck it up that she had sex with Jack.

  “But sort of hot too, right?” she added. It felt like she needed me to validate it. I couldn’t bring myself to puncture her good mood.

  “Yeah,” I replied. “What happens in Vegas –“

  “Stays in Vegas!” she exclaimed eagerly. She kissed me on the cheek. “Come on, this’ll be fun.”

  III

  Jack was waiting for us downstairs in a vintage, baby blue Caddy. I sat in front with him, making uncomfortable small talk while Leslie napped in the back. I mean, what do you say to a guy who just spent the night railing your wife?

  “Nice car.”

  “Thank, buddy, restored it myself. Got a big ol’ yard full of wrecks I work on.”