Tuesday 7th November 2017

I’d just watched Jill’s shapely ass sashaying away from me as she headed towards the elevators hand-in-hand with Rocco. The last few minutes hadn’t gone anything like I’d expected.

When I’d switched her normal work clothes for sexy, revealing clothes and then sent her a smiling emoji when she said she had to work late, I’d thought I might be pushing her into the arms of her handsome boss Chris. But ever since I’d arrived at the meal, and especially since we’d retired to the bar, it had been the gruff-looking Union boss who’d been putting the moves on my sexy wife. She’d not said anything, but I was pretty sure Jill’s acceptance of Rocco’s advances was her way of sending a message to me. Her way of telling me that I may have pushed her in a certain direction today, but that she was the one who’d ultimately make the decisions. It was her body, and even if I nudged her towards Chris, she might do something and sleep with someone entirely different from what I’d planned.

And now, with Chris gone to the restroom, I was sat alone in the bar wondering how things were going to develop. I smiled ruefully to myself, a shudder of fear and anticipation running down my spine as it dawned on me that I had no idea how things were going to play out this evening. On the two previous occasions, we’d played this game, we’d either jointly agreed things or I’d been in the box seat. But this whole unexpected development with Rocco had added extra fuel and fear to the fire.

I’d never met this guy Rocco before, and Jill had only met him a handful of times, yet she was now upstairs in his hotel room having sex with him. What if he turned out to be some kind of deviant? What if he didn’t want to play by the rules and wanted to steal Jill away from me? What if … what if … that was the bottom line, I’d let Jill go upstairs with a guy we didn’t know from Adam. Less than three weeks ago, we’d been a normal couple doing normal couple things. Faithful for more than twenty years, and here we were with me alone in the bar and Jill upstairs with the second new man she’d been with inside ten days. No doubt kissing him like they’d kissed on the dance floor. No doubt giving herself and her sweet body to him just as she’d given herself to Daryl.

How the hell had things moved so far and so fast in such a short space of time? How had we moved from ‘pause’ to ‘full speed fast-forward’. Things going faster even than when we’d tried swinging. I knew I had a big dollop of the blame for this – it had been me who’d dressed Jill up and sent the emoji – and this thought didn’t make me feel great. If Jill was upstairs with some kind of deviant or sicko, then I’d never forgive myself.

These thoughts of guilt and worry were interrupted by Chris’s return. He smiled sheepishly at me. “You okay, man?”

“I’m honestly not sure, Chris. How well do you know this Rocco guy? Is he okay? Will Jill be okay with him?”

Chris actually looked relieved. Relieved that my only concern was with Rocco’s trustworthiness. Rather than the wider issue that he’d been the enabler to my wife being upstairs having sex with another guy, and how I might feel about that.

“It’s okay, Dave,” he reassured me. “Rocco’s a standup guy. I’ve known him a long time, and he’s got a wife and kids at home. He’s not going to do anything crazy with Jill, anything she doesn’t want.”

The confident look on Chris’s face and his reassuring tone and words made me feel better. Taking the edge off my fear, allowing my gut-wrenching excitement at the evening’s developments to finally start to sprout and bloom as my fear receded.

Seeing the change in my demeanor gave Chris the encouragement to ask something that I guess had been on his mind all evening. “Well, Dave, when Jill told me about your little excursion into the wacky world of swinging, I have to say you could have knocked me over with a feather. I’ve got to ask, how the hell did the two of you make a move like that after so many years of marriage?”

From the look on his face, he wasn’t poking fun or anything like that. He was genuinely intrigued at how a couple he’d known as friends for the last few years had come to such a potentially life-changing decision.

“Come on, Dave, man. Spill,” he encouraged, his smile gently mutating into a conspiratorial smirk. His smile implying a kind of ‘come on, we’re all guys together’, that this was nothing more than locker room banter that guys should share.

The nerves I felt at answering his question temporarily distracted me from what was happening upstairs in Rocco’s hotel room. He might be a friend, but looking across at Jill’s handsome and suave boss, I felt hugely embarrassed to own up to my fantasies about Jill and other men. I knew I’d feel too belittled to make such a direct confession to a guy like Chris.

“I guess after all these years we just thought it might add a bit of a spark to try something different. We had a bunch of friends telling us how great it was and so we took the plunge. I went with a woman called Gemma and Jill had some fun with a guy called Daryl.”

Chris grinned. “Hell man, if I’d known you wanted to play games like that, I’d have offered to help you out myself.”

Not knowing how to react, I tried my best to make light of his comment with a laugh that came across as anything but relaxed. My strangled throat revealing my nerves, my mind full of thoughts about how things would now be between Jill and Chris in the future.

Chris and I talked about it a bit more, and the more we talked the less awkward I felt about the subject. Chris asked me about how what we were doing felt for both of us, and aided by another couple of rounds of drinks, I tried to get across the bewitching mix of excitement and jealousy. I did my best to play armchair psychiatrist, explaining that we could only do what we were doing because we trusted and loved each other so much and so deeply. That if I had any doubts about Jill’s commitment and love for me, then the whole set-up would be too frightening and painful to contemplate. But that being secure in our love, we were able to enjoy the intoxicating mix of emotions of allowing each other to go with different partners.

Inevitably Chris repeated his earlier texted thanks about the sexy outfit I’d dressed Jill in this morning, as he playfully asked if I’d be kind enough to do the same every Tuesday and Thursday. By then I was feeling sufficiently relaxed to joke right back. “Why stop at Tuesdays and Thursdays. There are five days in the working week and busy executives like you and me deserve a few office perks.”

Our conversation seemed to be running out of steam a little when Chris’s phone beeped with an incoming text. Chris smiled as he picked it up and read the message, handing it to me. ‘Dave, Chris. Why don’t you guys come upstairs now? We’re in room 1805. Jill and I are taking a bit of a breather. We need a bit of a break before round two! Rocco’

“What do you think, Dave? Are you up for it?”

Confessing to another guy that you want to head on upstairs to watch another guy have sex with your wife is a hell of a thing. But I guess we’d talked enough and the booze had done its work enough that I just about managed to force down all those ingrained behaviors to shrug my shoulders. “Why not?” was about all I could stammer as I got to my feet and tried to pretend I was more sober and relaxed than I actually felt.

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Neither Chris nor I spoke in the elevator, my friend having the presence to realize small talk was probably the last thing I wanted right now. It felt like an eternity as the elevator hauled us up to the eighteenth, where my wife was waiting for me in bed with another man. Finally on the eighteenth, as the doors shut behind us, they seemed to shut with the finality of cast iron doors clanging shut as a prisoner leaves his cell on death row. Only the final destination ahead.

The corridor seemed to go on forever, allowing me plenty of time to wonder what I’d find the other side of the door we eventually knocked on. As Chris knocked to announce our arrival, I was struck by the thought how the lifestyle Jill and I had briefly dabbled in had just ‘jumped the species barrier’ as students of epidemics say – jumping from our private little group into the full reality of Jill’s work and ‘real’ life.

It was a sobering thought which I had no time to think about as the door was almost immediately opened by a bare-chested Rocco, who smiled at me as he peered around the edge of the door and invited us in. Taking a deep breath to try and counteract the huge jolt of adrenaline my body had just created, I was both looking forward to and fearful of what I’d find inside.

As I walked in behind Chris, Rocco gave me a self-satisfied grin, his smile meaning he didn’t need to really say anything. The first thing I noticed was that the President of the Union obviously warranted more than a standard hotel room. Mr. Rocco Rosetti had a large and luxurious suite, meaning that Jill was nowhere to be seen as I entered. No doubt further into the suite, lying on some large bed after her recent exertions with her new lover.

As I carried on through the small vestibule into the suite’s sitting room, I looked back to see that Rocco wasn’t just shirtless, he was butt naked. Sitting close to him at dinner and at the bar, it had been clear to me that he was a bear of a man, not blessed in height but with a width of body that suggested manual labor and great strength. Now seeing him unclothed, the impression was even starker. His chest seemed infeasibly broad, the thick carpet of dark hair only emphasizing his virility and masculinity. I tried not to stare, but my eyes went to the thick hose of a cock hanging sticky and limp between his legs. No doubt only recently limp, having done its work and shot its seed deep into my Jill’s body.

Rocco caught my momentary glance at his manhood, but said nothing, playing the cool guy as he walked naked towards the minibar and asked Chris and me if we wanted a drink. Chris asked for a bourbon and although the only thing I really wanted was to see Jill, I found myself asking for a cognac. As he rummaged around fixing the drinks, Rocco read my mind and not even bothering to look at me, told me, “She’s through the door just behind the TV. Be my guest.”

Being given permission to see my own wife was a step too far. As he turned and handed me my drink, Rocco could see my angry reaction. Holding his hands up, he tried to apologize. “Sorry, Dave. I didn’t mean it to come out like that.” He then held his hand out in a mixed gesture of contrition and friendship, and I found myself in the surreal position of shaking hands with a butt-naked guy, trying not to look at the swinging meat between his legs, fresh and shiny with the mixed juices of him and my wife, juices from their recent coupling. Taking my drink, I decided to ignore him and go through and find Jill.

Stepping past the TV and through the adjacent door, our eyes met even before I was fully through the door. I was overcome by a strange nervous feeling. Something I’d not felt since our early dating when I’d sometimes felt in my heart Jill was still actually Callan’s girl. With Daryl, it had felt totally different. I’d been the one doing the giving. This time I’d given the first tiny nudge, but then it had been Rocco doing the taking and Jill doing the giving. That’s why I felt so damned nervous, so much in need of a sign from Jill. Seeing the way Jill had been dancing with and making out with Rocco, I was in urgent need of some TLC and reassurance from my sexy wife.

As our eyes met, I immediately knew Jill was as nervous as I was. My feelings were all over the place and I didn’t know where to look. At Jill’s sweet and nervy smile or at her half-naked body which was on display to anyone who cared to look, with the duvet only covering her bottom half. I don’t think she’d ever looked more sexy or more beautiful to me in all our years together. Sitting there as she was, propped up in another man’s bed. Her full and shapely breasts gently falling and rising with the rhythm of her breathing, several love-bites obvious on her tits and chest, her nipples still swollen and showing her continued arousal.

“Hey you,” was all my nervous wife could manage to get out.

“Hey yourself,” my equally adolescent reply, as I continued walking so I could close the distance. Walking around the left-hand side of the hotel bed so I could hug the woman who was still everything to me, despite her current position propped up in another man’s bed.

Our embrace seemed to go on forever. As we held each other, squeezing tight, a little voice kept asking why this felt so different than the time with Daryl. For now, I ignored the question, preferring instead to luxuriate in the reassuring feel and touch of my wife. Just for a moment forgetting the other two men in the suite. One of whom had already fucked my wife, and one of whom almost certainly planned on fucking her before the night was over.

Finally, we’d hugged enough to release each other, pulling back so we could look at each other. Jill looked less nervous now, a gentle smile playing around her lips. “Are you okay, honey?” she asked me, my heart skipping a beat with happiness at her concern for my feelings. (I know, stupid after so long together, but at that moment I really needed the reassurance.)

Our lips met. I needed this more than answering her question, my smile telling Jill what she needed to know.

But my moment of calm and reunion was rudely interrupted, as I felt a rough hand on my left shoulder, turning away from Jill to be greeted by Rocco’s grinning features.

“Room for a small one,” he asked me as he squeezed by, before looking at Jill. “Scrunch up, Jill, baby. I’ve got a promise to keep for Dave. He waited patiently downstairs and now I’ve got to make good on my promise to put on a bit of a show for him. To make love to his pretty wife while he enjoys a ring-side seat.”

I was back to wanting to smash him in the face, although in truth I couldn’t argue with the truth of his words, but the way he teased me left me feeling angry and like some circus-show freak. Again he flashed a half-apologetic smile as his naked body pushed next to Jill in the bed. Pushing her away from me and putting his naked body as a barrier between me and my conquered wife.

As if to emphasize the point, he snaked a thick and hairy arm around Jill’s naked shoulder, his hand on her shoulder marking his territory as he turned from me and smiled at Jill. “What do you think, Jill, baby. Are you ready for round two? Have you got your second wind back, to go a few more rounds with this happy old man?”

His self-deprecating comment wasn’t fooling anyone. Modesty was the last thing on his mind as he lined Jill up to show me what he could do to her. What games he could play, and how he could make her squeal and moan in response to his love-making.

I suddenly felt very awkward, my kiss and hug with Jill broken and now feeling the odd man out, fully clothed as the naked couple looked at each other in bed, Rocco turning Jill’s face towards him as he gently kissed her lips.

Their kiss seemed to last an eternity as I saw Jill’s passion and excitement build as the kiss continued. I was ashamed to admit to myself, but despite how I’d bridled at Rocco’s sarcastic teasing, I felt the blood flooding into my dick, unable to tear my eyes from the couple in front of me. My own breathing was soon getting short and shallow in a poor man's mimic of Jill and Rocco’s own excited breathing.

Again I felt a hand on my left shoulder. “Don’t they look hot. You’ve got a hell of a sexy woman there, Dave, buddy. If I’d had a woman like that waiting for me at home, hell I’d probably still be married,” my wife’s grinning boss announced.

By now, both Jill and Rocco were oblivious to anything but each other, Rocco’s rough hands now alternately cupping my wife’s soft flesh and then rolling her nipples, winning a series of satisfied and contended moans from my wife. Looking at the way the older man was skillfully manipulating Jill, I knew that we were in for a repeat performance of what he and my wife had been doing ever since she’d teased me and led Rocco towards the elevators.

I couldn’t help but draw the comparison between Rocco and Jill and our only similar experience, with Daryl and Jill. That had been game-playing within a safe little fantasy world created by bored couples within the middle-class Miami suburbs. This was real life, Jill sleeping with a Union boss while her boss of the last five years looked on and waited his turn.

They continued to kiss and toy with each other’s bodies, Rocco slowly moving Jill so that she was lower in the bed and he was resting between her legs. The lower half of their bodies were still covered by the duvet, and I realized the full depth of my kink as I cursed this and the fact that I couldn’t see what was going on below the duvet. For a moment I toyed with pulling the duvet back, before realizing this would have been a humiliation too far.

I was still thinking about this annoying veil when I heard Jill’s mewling squeal that told me without a shadow of a doubt that the hairy Italian had penetrated her with his fat cock. As if to emphasize the point, Jill wrapped her arms tight around his thick neck and pushed her panting mouth hard onto his, crushing their faces together in the heat of her passion.

Fuck, why did I find this so arousing? Twice in the last minutes, I’d let this guy poke fun at me, yet here I was saying nothing and doing nothing as I looked on almost as excitedly as the lovers themselves. Willing them on, waiting for Rocco to speed up and do Jill properly. Almost mentally licking my lips at the prospect of the sound of Jill’s orgasms which I knew I’d soon be hearing.

To my abnormal mind, it was all a perfect tableau. Coming together in a perfect picture. My loving wife’s arms wrapped tight and possessively around another man. Her moans and sobs heartfelt and emotional as I saw the shape of Rocco’s steam-hammer ass moving up and down beneath the pure white fabric of the duvet. The combined shape of Jill’s splayed thighs and his muscled ass all the more erotic for the fact it wasn’t directly seen. Jill’s eyes screwed tight shut as she blocked out everything except the man between her legs, the man deep in her body pounding away at her and making her feel so good.

They went at it like this for an age, with Jill’s excitement building every minute until I could tell she was on the edge of coming. She can only have been moments away when things started suddenly changing. Rocco turned his head leftwards and looked past me, before then turning back to Jill and whispering something in her ear that I couldn’t catch.

Her response was instant, as her eyes burst open and just like Rocco she looked past me, her eyes suddenly showing confusion and a little panic.

I felt a rising nausea in the pit of my stomach as I turned to look behind me, instinctively knowing what I’d see. I’d been so pre-occupied with what was happening between Jill and the Union boss, that I’d not heard the rustle of Chris’s clothes as Jill’s boss had stripped naked. Now standing only a foot behind me and gently stroking a menacing and very hard erection.

As Jill continued to look at her boss with that ‘deer in the headlights’ look of confusion and indecision, I wondered if this was the first time Rocco and Chris had shared a girl like this. I wondered if this had been their plan all along.

Seeing or hearing no active resistance from my wife, they jointly took this as a sign of consent. Rocco gently reaching behind him to unlock Jill’s legs which had been locked around the small of his back. This allowed him to pull back and move to the right-hand side of the bed, as Chris squeezed past me and replaced Rocco between my wife’s still wide open legs.

During this seemingly well-choreographed maneuver, the duvet was kicked away and I found myself gazing at my wife’s engorged and battered pussy, her lips puffy and still pushed out in the shape of a fat ‘O’ shape by the girth of the cock she’d been enjoying all evening.

I don’t know why, but somehow this sight brought it home to me afresh just how far our marriage had moved away from the normal and conventional monogamy. A monogamy we’d happily practiced for the twenty years we’d been busy raising and nurturing our family. I didn’t think of this realization as either a good thing or a bad thing. It was just a moment of thinking ‘hell, everything’s changed so much’, mixed in with an indefinable sense of not knowing where this new direction of travel would take us.

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This sense of the huge changes that had taken place in our marriage was amplified exponentially over the next hour or so as Chris got into the position he’d no doubt wanted for so many years and lowered his hips on top of my wife. Unable to stifle a shit-eating grin as his PA of the last five years finally surrendered and took his big cock. His PA, my wife, emitting a long low moan of satisfaction as his cock plugged the hole so recently vacated by his friend Rocco. His hips soon moving up and down to take Jill back up that hill towards the climax that Rocco had denied her.

For the next hour, the two of them took turns to enjoy my wife’s charms. This is a little unfair as a description, as Jill was anything but a passive vessel as Chris and Rocco switched back and forth as they tag-teamed a very happy and fulfilled woman. I counted at least four climaxes Jill enjoyed as these two virile alphas temporarily set aside their natural competitiveness to share together the receptive female available to them.

Towards the end of his second turn on Jill, Chris asked me if I wanted a go.

I was genuinely torn. A big part of me was ashamed to admit just how much I was enjoying watching this carnal and debauched threeway scene, with my Jill at the center. This part of me was happy just to watch and enjoy the show. But another part of me wanted to be one of the guys, to be one of the guys ravishing and pleasuring my wife.

When Chris had made his offer, Jill had been totally out of it. She was just coming down from her second climax, and I was pretty sure his words hadn’t registered with Jill. So when Chris moved out and it was my cock rather than Rocco’s much thicker cock that she felt nudging into her, Jill’s eyes opened with a look of surprise. In that split second, Jill’s eyes and face cycled through a mix of different emotions. First, surprise that she was looking at me rather than the Italian’s features, which she’d expected. Followed fractions of a second later by a look of slight disappointment at the dimensions of the new cock occupying her. Followed, I’m glad to say, almost instantly by a look of happiness that it was now the man she loved who’d joined the fun and games in bed.

Seeing this last emotion on that face which meant so much to me immediately made me feel a hundred percent sure that I’d made the right decision. It felt wonderful to be deep inside Jill, this amazing and satisfying feeling making me forget that I was the third guy to be enjoying my wife this evening. Even though she did seem a bit looser and less snug than normal, being enveloped by her pussy and feeling her soft arms and legs wrapped around me was a heavenly feeling beyond description.

As I pushed all the way in and kissed the love of my life, I knew there was a totally different quality to our love-making compared to what she’d been enjoying with Chris and Rocco only moments earlier. I saw this in her smile, and I had no doubt she saw the same thing as she looked up at me. Two people happy, knowing that the new games we were playing were only adding to our love and happiness. In no way detracting from or undermining our deep love.

Jill and I made love like this, luxuriating in our closeness and the feel of each other’s bodies. In some ways back to that freshness and novelty we’d known so many years ago. The feeling was so wonderful that I knew I couldn’t hold on for long, and I whispered a ‘sorry’ so that only Jill could hear, and made one final lunge as I pushed deep and groaned with the joy of release.

We held each other close, the tight hug giving way to gentle and tender kisses until years of habit told me it was time to lift myself up and take my weight off Jill.

Only unlike those years of habit, this time when I lifted off, I didn’t roll to the side so we could kiss and cuddle our closeness. I rolled to the side and immediately felt the warm flesh of another male rubbing against me as Rocco moved in, still hard and unfulfilled and ready to replace me inside my wife.

Having shot my bolt, I had a middling to mild case of the ‘spent balls blues’ as I sat at the side and had to wave goodbye to the wonderful closeness we’d just shared. Watching with a limp dick, spent balls and lowered adrenaline as first Rocco and then Chris took my wife again. Both of them bringing her to intense climaxes as Jill’s arms and legs wrapped around them, just as they’d so recently been wrapped around me. Until both of them had, having lasted longer, finally shot their seed deep inside my squealing, sobbing and very happy wife.

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As Jill and I snuggled close in the backseat of the cab, neither of us had the energy or desire to talk. Chris had (very generously!) told Jill to take the Wednesday off, so I guess we both knew that the talking which was needed could wait til tomorrow when we would have the energy and perspective to cope with discussing this latest and unexpected detour in our marriage.

What I didn’t know at the time was that the conversation we were about to have wouldn’t just be a backward-looking assessment of how we both felt. It would also be a discussion of something that would have a major impact on the rest of 2017 and the months beyond. Something that had seemed so innocuous when Jill had told me about the negotiations, but which was to prove anything but innocuous as events rolled forward.