TITLE: When Anything Was Possible Pt 2
AGE: 41 - 50
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We weren't expecting Jackie's girlfriend Nina to show up any time soon. But, it was her I heard call "Go on Bob, fuck her!"

It sounded like a good idea, even if I'd had it first. After all, Jackie was naked and stretched out face down on a poolside chaise lounge. Her hands were above her head gripping that chaise lounge's top rail. I was naked, kneeling between her legs and in possession of the necessary equipment. And, because I was leaning in, my hands busy rubbing sunscreen in to Jackie's shoulders the bouncing head of my cock was probing, teasing over her pussy's soft slippery contours and sometimes over her smaller alternative entrance. That made the question in my mind, was it Jackie's ass her girlfriend expected me to take? It was Jackie's hushed–for my ears only-"My ass if you've got the balls, "that settled the matter.

The hands I ran lightly down Jackie's sleek flanks were slick with coconut scented sunscreen. And of course, so was the finger I ran down her perfect ass's silky cleft. My index finger was barely a knuckle deep when Jackie pushed her ass up and back. Taking what she wanted, she left herself spiked on my stiffened finger. And, as I began a slow spiraling retreat Jackie, her breath already quickening whispered "now, fuck me!"

Jackie still gripped the chaise lounges top rail, but she was only halfway up on her knees. So, I was up on all fours as my cock's sunscreen slickened head probed and then began to penetrate. I backed off once, reentered and with Jackie panting out happy sounding noises I pushed deep with one slow, smooth thrust. It wasn't the first time I'd stopped snugged deep in the slick, molten heat of Jackie's tight full-length anal embrace. This time though, I took my showboating time, daring to ignore her increasingly adamant demands for harder as I continued to slide in one agonizingly slow fully penetrating thrust after another. Anyway, it was definitely working for me, and considering the animated, loud, and increasingly enthusiastic noises coming from Jackie, a guy could be forgiven for thinking she was every bit as orgasm bound as he was.

Nina put in an appearance about the time I was thinking; fuck her if she doesn't like the show we're putting on. But then, there she was, naked and settling to her knees beside the chaise lounge. Jackie's face was turned away, so she didn't even know her instigating girlfriend was right there and about to go up close and personal. Did I care that it was Nina's encroaching finger that triggered Jackie's explosively vociferous climax? Hell no; after all, it was me her anus's climatic spasming pushed over the top.

It was my landlord's fault, not that he was paying for the three day getaway his fuckup had initiated. But, on the bright side my erotic boutique was getting a spiffy-new parking lot. And, having decided, fuck it, closing for a Sunday and Monday seemed like a good call. That's why me, Jackie, my store's young lesbian inclined and utterly uninhibited store manager, plus the rest of my store's crew, along with a pair of significant others were able to make an escape to my favorite nearby high desert resort. The crew included Asha, whose Japanese features and California beach bunny body along with her recent sexual exploits had earned her the nickname of, Tres. Monica was my store's assistant manager, a Latina hottie. And, even if she didn't make a big thing of it, I knew she and her live-in boyfriend Mario did some casual swinging. Then, there was Roger, also like Asha a part-timer. Another College student, Roger was a tall good-looking guy, who rumor had it hadn't yet scored with any of his licentious coworkers.

Jackie and I got a head start and settled in to a swank three-bedroom condo with its own private pool and access to room service on Saturday. And, we weren't expecting to see Mario and the rest of the crew until sometime early Sunday evening. That left Nina, Jackie's hot blonde girlfriend, and we hadn't been expecting to see her before late Sunday afternoon. Jackie, who made a habit out of non-monogamy, had told me her normally monogamous, but otherwise sexually adventurous live-in partner had expressed a desire to push the boundaries. So, the way I saw it, just about anything was possible.

Sure, Jackie and I eagerly anticipated Nina's arrival. That doesn't mean we were hoping for an early one. But there we were, me totally getting-off on doing Jackie right in front of her girlfriend. Of course Jackie knew she was there; after all, it sure wasn't me fingering her clit. I was the guy clutching her hips as he slowly worked seven inches of hard cock in and out of her ass. She took it, murmuring "Harder Bob," while continuing to ignore her clearly unconcerned girlfriend. Anyway, I was frantically pistoning cock in and out of Jackie's spasming asshole, while a whooping Nina's practiced finger extended her orgasm. Jackie who freely admits to liking, as in seriously gets off on taking it up the ass was still making unintelligible guttural cries when I pulled out, grunting in an animalistic frenzy as I splashed a final massive ejaculation across her ass.

Nina laughed, slapping her lover's cum splattered ass as she teased "Told you so!"

"Didn't count," Jackie snapped back.

"Yeah, well you came! Uh-huh, and I'm pretty sure that was Bob pounding his big dick in to your ass, while you girlfriend, screamed your fool head off," a chuckling Nina answered.

Putting an end to the debate, Jackie rolled to her feet, ran the few necessary steps and dove in to the pool. Nina and I exchanged a knowing glance, both of us laughing as we slapped a high-five. And, of course by then I'd gotten my first good look at Jackie's naked girlfriend. Nina, as I already knew was blonde; and because she was lasered just as wickedly bare as Jackie, I was left staring while still wondering if she was truly a natural blonde. But, she had long legs, an awesome ass and big firm boobs; so, who cared anyway? And, she sure didn't seem to mind my appreciative stare either.

"She tells me everything you know," Nina explained. I nodded, not sure I bought in to that everything bit. But, I was happy to shut-up and listen. And, I was only a teensy-weensy bit skeptical when she claimed "Jackie says anything goes. So, I guess that like her, I'm free to fool-around. So, yeah count me in!"

"That'll be virgin territory for Jackie," I said ahead of an enthusiastic "But, hot damn girl, you're off to an awesome start!" And, because I was thinking it, I just had to add "Don't know; but, sometime this weekend I'm going to make you cum right in front of her, and I'm going to be looking in to her eyes when I do!" Then, already headed in for a quick shower, I turned back to add a hopefully encouraging "Hey Nina, just don't do anything Jackie wouldn't do!" It's always good to leave them laughing…right!

There was an inflatable rubber raft in the pool, the French kind. They look kind of like a monster size waffle, only the depressions are round and big as typical cup holders. And, in anything less than a full on petal to the metal fuck they hardly ship any water at all. Anyway, when I walked back out on the patio Jackie and Nina were stretched out on that rubber raft. They were making out while doing a clit polishing pelvic bump-a-thon. I moseyed around, found a spot with a good view and parked my butt pool side. I popped the top on my beer and watched to see which of the rock n' rolling duo would cum first. Nina did; but I say Jackie cheated. At least I hadn't expected to see her slide off her obviously near-orgasmic girlfriend. But she did; and then, she quickly maneuvered the raft so I was looking right up between Nina's wide spread legs. So, from my front row seat I watched Jackie work one, two, then three, and finally all four fingers in to Nina's obviously well-lubricated pussy. Then, while running that handful of fingers in and out she began to rub a thumb back and forth across Nina's well-exposed clit. They were making out; but of course I was watching Jackie's hand. Still, I knew Nina was screaming in to Jackie's mouth as she came.

Jackie whispered something in to Nina's ear. And I swear she was cackling when she pushed Nina off the raft. Nina came up sputtering, but was laughing as she questioned "What, so you're daring me?"

Nina didn't need to worry about getting me up. There was a towering length of hard cock waiting for her when she arrived. And, while Nina braced on my thighs and bobbed her pretty blonde head up and down that cock's full length, her girlfriend was sitting right there beside me. Actually, the bitch was swigging from my beer when she wasn't busy describing her cock-sucking girlfriends handful of non-lesbian sexual exploits. "No really, this is only the third time she's actually had a cock in her mouth, or so she claims anyway," A snickering Jackie gleefully explained. "Yeah, but she wound up jacking one of the guys off," she explained. "Gosh, and I suppose the other guy must have gotten bored; anyway, he flipped her over and fucked her," she added before reaching out to push her scowling girlfriend's head back down. So, I was braced back on my elbows Jackie running a fist up and down my cock while Nina sucked on its head. But, when I began to blow hard, correctly interpreting my condition Jackie let go, jamming Nina's head down as she squealed, "Oh yeah, you're gonna swallow this time girlfriend!" Nina did too; with big geysering spurts of cum exploding in to her throat.

The girls showered, got dressed, and then we went grocery shopping. So, Roger and I were able to grill burgers while the girls fixed corn on the cob and put together a big mixed salad. Cold beer and some primo bud worked for dessert. Later, with everyone, for some silly reason or another having decided to wear their swim suits we baked in the condo's Jacuzzi. Maybe it was the pot; whatever, it was a fun, but still seriously tame evening. And then, somehow I was alone. Asha was sequestered behind a closed bedroom door, doing who knew what with Jackie and Nina. Monica was in one of the smaller bedrooms entertaining Roger and Mario. Somehow I just didn't suspect a four on one was in the cards.

, It was way later, and I was crashed on a sofa out in the Living room. I came awake, but only because someone was sucking my dick. I cracked an eye and discovered it was Monica, down on her knees indulging in a late-night snack. It was actually our first sexual hook-up; which yeah, is weird to say the least. Anyway, I was pretending to snooze when Monica slapped an open palm down on my belly and cried "Faker!" But then, she was laughing and peppering my face with kisses. And then she was up and straddling me, still kissing me as she maneuvered herself in to position. She was squealing a resounding "Yes" as she slammed down taking every saliva slickened inch of me with that first downward plunge. I started to reach for her ass and got my hands slapped aside. "Let me, "Monica growled, her hands pushing hard against my chest as she rock n' rolled her way in to a quick little orgasm. Then, seeing as how I was still fully loaded, I took her bent over the back of that sofa. And, I was congratulating myself on a pretty good first fuck when Monica huffed out a breathy "Sorry, gotta run; Roger and Mario have a double-penetration waiting for me!"

The sun was up, and unfortunately so was I; unfortunate, because of course I was alone. I got coffee started. Then, steaming mug in hand I headed for the patio with a later swim in mind. Anyway, still decked out in my finest birthday suit I was swimming lazy laps as the others filtered out. Only, to my utter horror they were all wearing swim suits. At least for the girls it was skimpy, and in Monica's case less than skimpy bikinis. But, so what; it was still a, what the fuck moment; so, I ignored them.

Jackie and Nina sauntered over. Miffed, I ignored them and returned to swimming laps. Perfect, they ignored me. Sure they did; except Nina parked her sexy ass on the pool's edge. Not Jackie, she dove right in. I expected her to swim some laps; but no, all she did was clamber right back out.

Clueless, I thought, huh, and let it go at that. But being curious and of course horny, I swam over to where Nina still sat. Standing was an option, instead I leaned my forearms across Nina's knees, a move I knew would gently nudge her thighs a bit further apart. It worked, so I wasn't looking up when I asked "All good?"

"With me," Nina affirmed.

"OK," I said, and then asked "So, how come I'm the only one naked?"

"Beats the fuck out of me," Nina fired back. "But, Jackie came out wearing a bikini; so, well I suppose we all figured suits were like, you know de rigueur!"

"So, maybe we should get the party started by getting you out of yours," I suggested, already set to reach for the tiny micro-thong, stretched provocatively tight between her casually parted thighs.

Nina caught my hesitation, laughing as she reached up and slipped the knot holding her bikini's top in place. She tossed it aside and purred "You're move Bob!" Then, when she rocked up on one hip, I tugged. She rolled up on to the other hip and I tugged again. That left me holding half a bikini. A toss left it lying beside the discarded top. And by then Nina was braced back on her elbows, not exactly purring but definitely puffing out long slow breaths. That left me staring at her prettily exposed and very bare pussy. As laser bare as her girlfriend's, it was a duskier darker shade of pink that contrasted nicely with the café au lait of her thighs. And, pretty near blowing me away, amidst all that dusky pink was this big, definitely plus-sized clit. I could have been wrong of course; but, that tasty looking morsel didn't even appear to be aroused. Nina interrupted my gawk, her voice low and real sexy as she said "Jackie says I can't fuck you until after you make me cum!" So, I was looking up in to her grin when she suggested "And, well I really want to be fucked; so like, maybe you should get busy and make me cum!"

The invitation was unambiguous as a kick to the balls; still, Nina was obviously trembling. Well, I'd never had a woman quite that eager before; still, I assumed it was in anticipation. Just to prolong things a bit I offered a friendly warning. "Careful Nina," I teased. "If you start doing everything Jackie orders you to do, you're going to get real good at being really, really bad!" And then, with a tug I pulled her closer. And, growling like Tony the Tiger I started my day off with the true breakfast of champions, a big tasty helping of warm wet pussy.

Somebody was horny, and that somebody came lickety-split. And, because I thought that just maybe watching her girlfriend cum loudly and damn near faster than a speeding bullet would get Jackie's goat, well yeah, I let it happen. Once Nina got started, and went orgasmic, she made like the Energizer bunny and just went on cumming and cumming. Mostly because I really wanted to fuck her, but also because I wasn't sure Nina would ever stop, I did.

Most likely it had been quiet for a while; but, I didn't notice it until I was clambering out of the pool. I stood up, looked around, and wondered if maybe I was expected to take a bow. Instead I helped Nina to her feet, where she stood on shaky legs. She turned, looking about ready to head for where Jackie watched stretched out on the same chaise lounge we'd taken her on the day before. Nina hesitated, returning Jackie's knowing "Dare you" head tilted stare. Somebody should have blown a whistle; because, it was game on, at least as far as I was concerned.

Nina began to turn back, but I stepped up caught a fistful of blonde hair and pulled her head back. It left her turned sideways, her face angled enough to leave her eye to eye with Jackie. I pulled harder and Nina went with it, letting her back bow. I was between her legs, my hips pushing her's even further forward. It didn't matter; the head of my cock was still pushed between her thighs and right up against her pussy's wet heat. Her back was a taut bow as I began to work my cock in and out between her thighs. "Ask for it," I husked in to her ear, even as I gave her another forward nudge.

Nina, who was sucking in sharp gasps managed to make her "do it Bob…fuck me," sound like a defiant challenge. It was, just not one aimed at me.

It was a stretch, but I slipped in to Nina, one hand braced on her hip to steady myself. Her pussy flamed around my cock, slick as wet silk as I worked in a slow handful of gentle half-jabs. Actually, all I could manage were those half-jabs; but then, they seemed to be doing the trick. Anyway, even with Nina's breath coming in quick, sharp gulps, her occasional "yes-yes" still sounded clear on that silent patio. I didn't know, but maybe those jabbing thrusts were catching her G-spot, or maybe with the way I had her body arched my thrusts were pulling something tight and maybe generating some clit tickling friction. Whatever, Nina's excitement continued to ramp-up. It was going to be a race; but, I really did want her to cum first. And she did, not loudly, and maybe not even breathing, her body rigid and shaking as a flood of her pussy's juices poured down my half-exposed cock.

It was only luck, but only a few feet away was a vacant patio chair. I managed to signal with a jabbing finger. Roger got the message and gave it a push. It slid close enough for Nina to grab it after I helpfully suggested she might just want to "Grab it, and hold on tight!"

Nina locked her fists around that chairs arms, bent over and looking straight in to Jackie's eyes as I slammed lunging thrusts in to her from behind. Me, well I was much too busy to bother with anything silly as catching Jackie's eye. Besides, I just happened to know she knew what it felt like to be fucked, and fucked hard. She even knew what it felt like to be center stage in front of an audience, while some grunting half-crazed fucker swamped her pussy with an eruption of cum. And, lying there stretched out on a chaise lounge she watched that same grunting half-crazed fucker do the same to her just barely post-orgasmic girlfriend.

We had skipped breakfast, but we did do lunch. We ordered it from room service and ate out on the patio. Our room service waiter was still cleaning up, which didn't stop Mario from banging a wild doggie style fuck in to a loud and obviously appreciative Asha. I'm not sure the poor guy even noticed; because, like me he was watching the action out in the pool. The rubber raft was the stage; and, Monica had an orgasmic Jackie's legs pushed back above her head. Jackie came screaming "Do me bitch," while clutching a double handful of Monica's hair. She stopped screaming, which with Jackie meant she had also stopped cumming. But, she still held that double handful of hair and used it to encourage Monica up from between her legs and up on to her body.

Whatever Jackie whispered in Monica's ear, the answer was a clear "Nope not covered by that fucking raincheck!"

I assumed Monica and Jackie were haggling over the rainchecks they had claimed the day Asha and Jackie had swapped oral in my office. And, that had been after Asha had sucked off one of the stores customers, a regular from way back in the day. At the end Monica had been there making like a spectator and after declining to join in the fun, the girls had traded rainchecks.

Seeming to reconsider, Monica dared a challenging "Fuck it, I dare you!"

After a wild whooped, Jackie disentangled herself, rolled off the raft, hurriedly exited the pool, and made a dash for the condo. Too bad, but the room service guy was gone by the time Jackie came strutting back on to the patio sprouting nine very realistic inches of hot pink rubber dick. I knew it was a nine incher; but only because I had rung it up for her. At the time a nine incher was all we had in hot pink. Anyway, it swayed as Jackie walked, jutting from the gleaming black leather harness she wore buckled around her waist.

That guy from room service will never know what he missed. But then, neither will you; unless of course you watch for the next part of this story. ENJOY