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Four's A Crowd

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“This is weird, right? Tell me this isn’t weird?”

Harry gave him a wide-eyed stare tinged with confusion. “You said you wanted to do it,” he replied, and Jack could’ve sworn he sounded hurt by the implication that there might be second thoughts, even though those second thoughts would’ve had nothing to do with Harry in the least.

“I do,” Jack hurried to reassure him. “I do want to, it’s just….” He frowned. “Well, I mean, it’s your ex. It just seems…odd.”

They were waiting in the sitting room of a penthouse hotel suite—because that was the kind of thing Harry could afford, and more importantly, Taylor could afford. Because that’s who they were waiting for. Taylor bloody Swift.

And Joe, said a voice somewhere in the back of Jack’s mind. And maybe he didn’t want to admit that he was less apprehensive about having group sex with Harry’s ex-girlfriend than he was about being naked in the same room as his very tall, very fit co-star.

“I don’t have a problem with her being my ex,” Harry said earnestly. “Do you have a problem with her being my ex?”

“No!” Jack replied. “No, it’s not that. I’m just—” This was all backfiring on him very quickly, and he wasn’t sure how to salvage it.

As it turned out, there was no need. A knock on the door sounded before Jack could get another word out, and then the door opened to reveal Joe and Taylor, who walked in hand in hand, making Jack suddenly self-conscious about the way he and Harry were sat on the sofa exactly twenty centimetres apart, like a couple going through marriage counselling.

Jack wondered belatedly if he should move closer, or if that would just make the awkward distance more noticeable to Joe and Taylor, who had sat down on the other sofa opposite them.

Now Jack was really sweating, and he was never more thankful than when Harry got up to hug Taylor before sitting back down again, their thighs pressed close together now.

“I guess we should talk things through?” Harry said.

Jack spent most of the discussion quietly observing. Taylor and Harry handled most of the negotiations, particularly the use of condoms and whether it would be safe to go without. Jack was aware of Joe’s eyes lingering on him in the meantime, but he focused on Harry’s hands instead as they fluttered through the air in time with his slow speech.

By the time they moved things to the bedroom, they’d decided to use condoms for the sake of clean-up, but unprotected oral sex wasn’t off the table. Jack wasn’t sure what exactly that clause would lead to just yet, but his mind was already spinning from the possibilities.

Taylor and Harry seemed far too familiar for having only dated for a handful of months six years ago, and Jack couldn’t help but wonder if there was more to the story. He didn’t have the chance to ask, as they started stripping each other bare as soon as they stepped into the room, leaving Jack and Joe to play the part of voyeurs.

Jack sunk into the chair next to the bureau that Joe had chosen to perch on while they watched their respective partners undress each other. The sight felt reprehensibly taboo somehow, like the first time Jack had watched two women together in porn as a boy and wondered if it was something he wasn’t supposed to have seen.

Despite his unease, Jack found himself unable to take his eyes off the sight of Harry’s hands running along Taylor’s hips dragging her panties down to the floor before kicking off his own trousers into the corner of the room. Once they were both totally nude, Taylor took Harry’s face between her palms and kissed him deeply.

Harry melted into it. Jack worried that he would fall over if Taylor let go of him, but even after breaking the kiss she kept a steady grip on his jaw and upper arm to keep him stood upright.

“Should we go first, then?” she asked, looking between Jack and Joe for permission.

Jack’s eyes connected with Harry’s, and he knew the younger man could see the stirrings of fear in his face. Harry gave a tiny nod.

“Let’s give them a show,” Harry said firmly. He climbed up on the bed and got into position on his hands and knees like he’d done it a thousand times before. Maybe he had.

Taylor had moved away toward her bag to pull out a rather complicated-looking harness that Jack recognised from some of his more shameful internet searches. The dildo attached to it was small, smooth, and a pearlescent pink, which suited Harry rather well, Jack thought.

His breath quickened when Taylor finally slotted herself into place behind Harry, their bodies at an angle to give Jack and Joe the best view of what was going on. She lubed up her dick but didn’t bother to even finger Harry before pushing inside him.

Jack jumped a little in his seat, but Harry didn’t react as if she’d hurt him. It was the complete opposite, if the way his cock jumped against his belly was any indication of how much Harry was enjoying himself.

Before long, Jack was enjoying himself, too. Taylor had drizzled more lube onto her silicone cock after the first few thrusts, and now she was really going at it, pounding hard into Harry with her long nails digging into his hips while he folded himself down against the bed with only his arse tilted up to meet Taylor’s insistent movements.

Joe seemed to be thoroughly enjoying the show as well if the sound of his zipper was anything to go by. Jack was too afraid to take his eyes off of Harry and Taylor to look, but Jack could hear the sound of Joe’s hand working his own cock, even over the noises pouring out of Harry’s mouth as Taylor fucked him into incoherency.

Not wanting to be left out, Jack finally unbuttoned his own fly to take his cock out, wanking himself off slow as he watched Harry come undone.

Jack was hard well before Harry started to come, but he didn’t cease the movement of his hand until he could see Harry’s abs clenching, could hear the muffled high-pitched cries of orgasm—

And then Jack couldn’t see or hear anything at all, because there was another pair of lips on his, a large hand spanning his jaw to hold him firm as a tongue pushed into his mouth, searching for reciprocation. Once the shock had worn off, Jack gave it, giving himself over to the kiss and letting Joe take the wheel.

Jack was vaguely aware of the fact that both their cocks were out, but that didn’t truly register until Joe pulled away to reveal that Taylor and Harry had cleaned up a bit in the time that he and Joe had been kissing. Taylor was sat against the pillows on one side of the bed with Harry curled up into her side, leaving the other empty and inviting.

Jack felt his heart rate ratchet up before Joe reached down to tug at his hand. He gently coaxed Jack up and out of the chair and over to the bed instead, where Jack laid down flat on his back, stiff as a board with nerves. He’d had stage fright before, but never like this.

Joe picked up on his anxiety instantly. “Do you want Harry to get you ready?” he asked as he peeled off his shirt, revealing a body far broader and more toned than Jack had ever been lucky enough to possess.

Jack felt his throat close up. He nodded, feeling Harry’s hands on his shoulders before the other man came into view again, kneeling between his spread thighs. He smiled down at Jack reassuringly.

That was the whole point of this insane endeavour after all. Jack had made a drunken confession about wanting Joe to rail him into next week, and after ensuring that Jack wasn’t dissatisfied with their current arrangement, Harry had started making plans to give Jack exactly what he’d asked for.

Joe had known going into this what Jack wanted, and Jack knew that Joe knew. But Jack still couldn’t look the other man in the eyes as Joe stripped down at his bedside, choosing instead to stare intently at Harry, whose hands were a soothing balm as he unbuttoned Jack’s shirt and pulled down his trousers to leave him bare.

This was probably the wrong time and place to have such a realisation, but Jack was surer now that what he felt for Harry was something closer to love than friendship, and that while that love was fulfilling in its own way—and no matter how good the sex was—there were other things Jack needed. Harry wasn’t, and couldn’t be, everything.

Jack realised he’d been lost in his own head while Harry undressed him when he suddenly felt Harry nudging a pillow under his arse. Suddenly, everything became very real again, and Jack started to panic.

“I’ll go as slow as you want,” Harry reassured him as he reached to take the lube from Taylor.

But that wasn’t what Jack was worried about. He’d seen Harry finger himself at least a dozen times, had done it to him on more than one occasion. Jack wasn’t afraid of the pain, he was worried about the attention. All these eyes on him, analysing his reactions to having something put up his arse for the first time. Now, he wished he’d agreed to let Harry de-virginise him instead, but some deep, primal part of him wanted—needed—it to be Joe.

“Okay?” Harry checked as he slid his fingers down below Jack’s balls to his hole. He probed gently before pushing in, the copious amount of lube making for a surprising lack of resistance.

Jack nodded even though it didn’t feel good, certainly not the mind-numbing sort of pleasure that seemed to overwhelm Harry anytime he had a finger up his arse. He stared up at Harry without blinking while Harry worked his finger in and out a few times before pushing in a second.

Jack’s breath hitched in his throat. Two felt different. Very different.

Suddenly, Jack could feel Joe’s eyes burning a hole through his skull, but he didn’t break Harry’s gaze.

“Good?” Harry asked. He wasn’t moving his fingers much, keeping a slow but steady pace as Jack’s body grew accustomed to the feeling.

Jack wouldn’t say it felt ‘good’, exactly, but two fingers definitely felt better than one, and now he wanted more. He nodded, hoping Harry would take the hint.

Harry didn’t, at least not for a few agonising minutes of anticipation. When Harry finally pushed the third finger inside along with the first two, Jack immediately began to regret his eagerness. Three was a lot. Too much, maybe.

“Just relax,” Harry encouraged. “You can take more than you think.”

Jack knew that from second-hand experience but being on the receiving end was a lot different. It felt like an eternity before the burning pressure faded to something more bearable. He nodded, still looking up at Harry, to signify that he was ready. Physically, at least.

Nothing could have prepared Jack for the reality of having Joe take Harry’s place, looking larger than life as he climbed onto the bed to kneel down between Jack’s knees. He was unabashedly naked as he palmed his cock, which was thankfully very average but by no means unimpressive.

“You sure about this?” Joe asked with a smile. “Not too late to back out now.”

Jack nodded, putting on a face of false bravado that he assumed wasn’t in any way convincing. “I’m sure,” he said, even though he was beginning to think he’d never been less sure of anything in his life.

Jack felt overwhelmed by a strange mixture of satisfaction and revulsion when Joe finally lifted his legs to brace them over his arms. He was spread wide open, his face white hot with shame and anticipation before Joe’s cock even brushed up against his arse. Then there was an unforgiving pressure, and release, and Jack suddenly couldn’t breathe he felt so full.

He was still, very still, as Joe slowly pushed into him to the base. Jack was worried if he allowed himself to move a single muscle that he’d come just like that, just from having Joe inside him. But not just that. From having Joe covering him, surrounding him, his arms bracketing Jack on either side of his head like a cocoon. Jack knew now why Harry loved this so much, and now he wished he didn’t.

Some part of him, maybe the same part of him that wanted this so badly, was terrified to let any of them, even Harry, know that he liked it.

Harry must have sensed that Jack was getting lost again, because suddenly his lips were moving softly against Jack’s, giving him something to ground himself with.

Harry pulled away just as Joe started to actually thrust. It took Jack a minute to sort through the cacophony of new sensations assaulting his body before he realised that Taylor was lying on her back next to him now and that Harry was sat on top of her.

They weren’t fucking again, not yet, but that changed just a few seconds later when Harry impaled himself again on her strap-on, letting out a sound that was somewhere between a moan and a yell.

Jack alternated between watching Harry ride Taylor and watching Joe moving above him, muscles flexing wetly under the dim illumination coming in through the window. He couldn’t seem to focus on anything even though Joe was barely moving in him at all—each slow drag of Joe’s cock inside of him felt like it was magnified by a thousand even though his own cock wasn’t being touched at all.

Somewhere in the haze of it all, Jack turned to watch Harry again and found himself meeting Taylor’s mouth instead. She tasted like lime and mint, and for a second everything went quiet.

Then Joe was fucking into him even harder, and Harry was bouncing on Taylor’s cock like he’d die if he didn’t come. Jack didn’t think about the fact that Harry couldn’t touch him like this until it was Joe’s hand wrapping around his dick instead, pulling in counterrhythm to his own thrusts until Jack was coming in messy spurts over his stomach.

His balls felt drained afterwards, like they ached from how empty they were, and Jack was a little disappointed that he’d come before either Taylor or Joe. Harry hadn’t even gotten a second orgasm in.

Joe had stilled as soon as Jack started coming, but once Jack’s head flopped back onto the pillow with a sated sigh, Joe unexpectedly pulled out. Jack sat up, startled, and braced himself on his elbow, trying to figure out what was going on.

Harry had rolled off of Taylor already and was lying facedown next to Jack. He smiled sweetly. “Hi,” he said in near-whisper.

“Hi,” Jack said back.

Above them, Joe and Taylor were breaking out another strip of condoms. “You don’t mind switching?” she asked. “Harry suggested it over the phone, but he said he wanted to surprise you.”

Jack was surprised. He hadn’t considered the fact that he’d be having sex with not only Taylor’s boyfriend but Taylor Swift himself, and with a fake cock nonetheless. Harry had seemed to like it though, and Joe still hadn’t come. It wouldn’t be fair to deny Harry the chance to experience something that Jack had finally decided was earth-shattering.

“I don’t know if I can get it up again,” Jack admitted as Taylor wiped off before putting on another condom and re-applying lube. Joe was doing the same, just on the other side of the bed now.

“Well, I do love a challenge,” she replied with a wink.

Jack spread his legs in answer and waited as she pushed into him easily. It was less overwhelming than being fucked by Joe, who was bigger in every sense, but the curve of Taylor’s strap-on pressed against Jack’s prostate on every thrust in a way that Joe’s cock hadn’t, and suddenly Jack understood why she hadn’t seemed concerned about the fact that he’d just come.

Next to him, Harry was getting more or less the same treatment, Joe pounding into him froggy-style with little restraint. Once Jack looked at him, he couldn’t look away, mesmerised by the soft punched out exhales pushing Harry’s lips out into a tantalising pucker.

With Jack on his back and Harry on his stomach, it was easier for them to kiss, but Jack didn’t let their lips stay connected for long. He was transfixed by the sight of Joe rabbiting into Harry’s arse even as he felt the stirrings of his own orgasm, or something like it, beginning to build in his lower abdomen.

He still wasn’t hard, hadn’t been since the first time he’d come, but there was a definite pressure building as Taylor fucked him harder and harder, and Jack wasn’t sure what to expect. It was almost like the beginning of an orgasm, the muscles in his pelvis tightening and tightening and then tightening even more.

The sensation didn’t change as Taylor continued to fuck him; it only got more intense, and then suddenly Jack’s eyes rolled back in his head as his mind emptied of everything else but the feeling of white-hot pleasure radiated through his body, making his legs lock up around Taylor’s waist as his dick leaked in a steady stream down his hip and onto the sheets.

When Jack was fully-conscious again and Taylor had pulled out, he could see that Harry and Joe were still going at it, but that Joe’s rhythm was stuttering, like he was just barely keeping himself from tipping over the edge. One look at Harry told Jack that he was close too, his eyes half-lidded, mouth gaped open around the shape of his low, guttural moans.

“Come inside him,” Taylor ordered breathlessly.

That was all it took before Joe’s hips juddered against Harry’s arse. His face was twisted up in an expression that should have been unattractive at best, ugly at worst, but Jack couldn’t tear his eyes away.

Harry whined quietly as Joe’s thrusts ceased, but he didn’t move, didn’t try to push back against the cock still splitting him open. He didn’t even try to rut against the sheets, and if Jack didn’t know for sure that he hadn’t come yet, he would have suspected that Harry was already asleep.

Taylor still hadn’t come yet either, but they were all exhausted by the time that Joe pulled out of Harry and flopped down into the tiny space between him and Jack, plastering every bit of his sweaty body along theirs.

Taylor observed them in silence for a long moment. “I’m gonna get some water,” she said, pausing only to peel off the strap-on harness before exiting the room.

Joe turned to one side to face Jack as soon as she was gone. “Do you know how to go down on a girl?”

Jack almost had enough energy to be affronted, especially when Harry’s laugh carried from the other side of the bed. “I was straight for all intents and purposes before Harry,” he pointed out.

Joe hummed in approval. “Good,” he said. “I want you to eat out Taylor when she gets back.”

Jack’s eyes nearly popped out of his skull.

“What about me?” Harry demanded childishly. He sat up, revealing a disgruntled expression that reminded Jack of an angry kitten.

Joe rolled over again to face him instead. “I’ll do you,” he said confidently.

Jack wondered if that meant Joe was bisexual too, if he’d sucked cock before this. Maybe Jack wasn’t the first guy he’d fucked.

Taylor wandered back into the room, arms laden with water bottles for each of them. They drank their fill while sprawled out on the bed, and then Joe nodded to Jack, signalling for him to take charge.

Jack whirled around and quickly pressed Taylor down into the mattress, carefully examining her features for any evidence that he should stop. Aside from a bit of mild surprise, she didn’t seem troubled by the manhandling. Even less so when Jack got her legs around his neck and started to lick into her, slow at first to get a feel for what she liked before coming up for air.

Jack glanced over at Harry, who was lying back in the same position, but where Jack expected to see Joe’s head, he found Harry’s hand working feverishly over his cock. Joe’s mouth was delving lower, he realised with a jolt of surprise, eating out Harry the same way Jack was eating out Taylor.

With that image burned into his retinas, Jack resumed his thorough exploration of Taylor’s cunt, savouring the experience he knew he might not ever have again.

She was sweet under his tongue, and the high-pitched cries streaming out of her were even sweeter, especially when paired with Harry’s more familiar cries of ecstasy as Joe went down on him with the same fervour.

Jack knew without looking when Harry came, his moans increasing in volume to rival Taylor’s, and it only made him more determined to make Taylor come. He needn’t have worried—her thighs clamped down tight around his ears only a few seconds later, her legs trembling as her pussy contracted against his mouth.

The flesh between Taylor’s thighs was rubbed raw from his beard by the time Jack pulled away, and he could feel his facial hair dripping with her wetness. Harry was on him before he could make an attempt to wipe at his face, hungrily kissing the taste of Taylor off his lips and tongue.

“Thank you,” Harry said, like Jack had been doing a favour for him and not the other way around. “Did you like it?”

Jack glanced up at Taylor and Joe, who were wrapped around each other at the other end of the bed, gazing curiously back. Harry was like that, always forgetting that there were other people in the room.

“Maybe a little too much,” Jack confessed honestly.

Harry smiled, apparently content with his answer. “Good,” he said, placing another wet kiss against Jack’s lips.