Caught in the Middle

by Kira Barker

  Jack looked a little spooked, but his voice was even as he responded.

  “I guess.”

  “Furthermore, I think Erin would feel neglected if she was the only one who wasn’t getting anything up her ass today, so I think we should do something about that, right?”

  I definitely liked where this was going, and so did Jack.

  “I guess that’s fair, too.”

  “The logical conclusion of that would mean that I fuck you while you fuck her, don’t you think? It also comes with the benefit of you having to do most of the work because she’s a truly insatiable cunt sometimes, and it’s only fair that you start making up for screwing with us by screwing us.”

  Jack tried to hide a laugh with a loud snort, incapable of keeping a straight face.

  “I think I like your idea of how I can redeem myself.”

  “I bet you do,” Simon said and leaned in to steal a quick kiss, surprising Jack, but clearly not in a bad way. “Remember, she has to ask for permission before she comes, so if you feel like she’s getting close, increase whatever you’re doing to make it twice as hard for her to hold out. That’s how you get her to scream the loudest.”

  I didn’t even try to tone down the angry glare I sent them both, and they only had twin, nasty smiles for me.

  Returning to the bed, Simon swept off the remaining pillows and blanket to make room, then slowly tipped me forward, one hand on my shoulder, the other supporting the weight of my torso in the middle of my stomach, until my body rested in a mostly horizontal position, the side of my head, shoulder, and knees balancing me, my toes now up in the air. I was suddenly glad that the pillows were gone—they might have been comfortable at first, but I didn’t mind not accidentally suffocating myself this way.

  “Hop up behind her,” Simon directed, then grabbed the condoms and lube he’d also brought down from the attic.

  The mattress dipped underneath Jack’s weight as he knelt down behind me, gently running his hands up the insides of my thighs to help me spread them as much as I could. I would have loved for him to do more, but he obviously waited for Simon’s instructions.

  “I don’t want your cock anywhere near her pussy. For now, that’s mine. But feel free to use your fingers to work her into a frenzy—you know that she likes to be stuffed.”

  In my position it was easy to hide the inevitable eye-roll, but while Jack was busy liberally pouring lube over my anus and anything that might even remotely resemble an erogenous zone in the neighboring region, he couldn’t stop himself from laughing softly.

  “How do you manage to say shit like that without cracking up?”

  “Practice,” Simon offered, for once sounding a lot closer to laughing himself than I was used to. “If you want a good laugh, ask Beth about verbal the next time you see her. Erin takes to it like the needy little slut that she is, but I hated it. I think that’s the only part of my training where she actually beat me into submission, and when she thinks I’m acting like a mopey whiner, she still whips it out randomly in conversations.”

  “Did you call her today?”

  “And get insulted? No way. Besides, she would have trashed my ass for slipping up like I did, and I’m not particularly fond of getting my balls handed to me like that.” Suddenly Simon was leaning close to me, his breath warm against the side of my face. “But if, for whatever reason, you should develop a grudge against me, I’m more than happy to let you and my former Mistress hatch a plan of how to make sure it won’t happen again.”

  That said, he crawled back until he was crouching behind Jack. My position didn’t permit me to directly see any more than the left side of Jack’s body from knee to shoulder, but the mirror on the outside of Simon’s wardrobe gave me the perfect view of what was going on behind me. While Jack reached for me to spread my butt cheeks with one hand so he could easier toy with my anus, Simon pressed himself flush against Jack’s back, one hand reaching up to his hair, the other wrapping around his cock to start stroking him slowly. The fact that I was incapable of moving anything except my hips back toward whatever Jack was going to do to me while I was forced to watch them was enough to make my vagina contract around the painful absence of anything stimulating.

  Jack wasn’t that much of a tease, though, and as soon as he started working one finger through my sphincter, his outer hand reached underneath me, sure fingers finding my clit and circling it in a slow, building rhythm. I forced myself to relax rather than tense with anticipation while I mulled over Simon’s words.

  What little he’d told me about this Beth woman made me both eager and scared to finally meet her, and while I didn’t think that I had much of a sadistic streak myself, seeing Simon suffer at her hands while maybe playing a similar role as Jack did right now made me lick my lips in anticipation. Not because I felt like he really deserved it for being as human as the rest of us, but because I knew that it was something he’d like, too, and the competitive aspect of seeing just how hard he could be pushed before he yielded so I’d have something to compete with eventually was appealing, too.

  Jack cut through my musing when he let out a low moan, apparently borne out of Simon kissing and licking along his shoulder, his free hand playing with Jack’s nipples. Jack’s cock looked almost ready for the next stage while he was still using only one finger inside of me, making me jerk my hips back as hard as I could when he pushed in the next time. A shudder ran through me when barely an inch deep became several all of a sudden, and Simon laughed softly when he looked for what had caused Jack to still.

  “You’re boring her, you know? What did I tell him, slut?”

  “That I’m insatiable, Sir?”

  “Right you are,” Simon confirmed, then murmured something into Jack’s ear that made him laugh, but also relax a little.

  A second finger joined the first with much more enthusiastic motions, and for a little while I didn’t give a shit about what was going on around me as I just let myself sink into the wonderful sensations created by Jack’s hands.

  Then they were gone, leaving me wanting for more, and when I saw him reach for the condoms, I knew I was going to get it very soon.

  The last time Jack and I had been in a similar, if for me less restrictive, position, he’d been slow and careful, but whatever Simon had whispered to him earlier made him abandon the concept quickly—or maybe it was the fact that my ass wasn’t painfully tight anymore, and while there was still the familiar burn of being stretched out as he thrust into me, it was a delicious burn now that made me arch my back and moan into the sheets underneath me. Strong hands gripped my hips for stability, then he pulled back out until only the head of his dick was still inside of me before he thrust back up, his balls slapping against my labia.

  He set a slower pace than I would have liked, and I guessed that Simon was responsible for that, too, but I cared a little less about it when Simon left his post behind Jack and instead crawled over to me. Sitting down with his back against the headboard, legs to either side of my shoulders, he then shimmied down into a half-reclining position until his crotch was right in front of my face. I didn’t need any directions to take his cock into my mouth, but when the angle remained awkward, I felt a sudden jerk at the ropes criss-crossing my back when Jack pulled my torso up. Simon slid down further, then grabbed my hair to steady my head so he could push himself deeper into my mouth, effectively fucking my face.

  In short, I was in heaven.

  Sadly, it was only a short duration soaring above the clouds as before long, Simon was hard enough to make the angle of his cock hitting the back of my throat uncomfortable, and the second time I gagged, he stopped. I must have looked rather disappointed because he laughed softly and leaned in to kiss me hungrily before he pulled back again.

  “Don’t worry. You’ll get plenty more of that before we’re done.”

  Then he returned to his previous perch behind Jack, in passing slapping Jack’s ass playfully.

  “Didn’t I tell you to finger fuck h
er, too? It’s been more than ten minutes now, and she hasn’t even started panting. That’s not really a performance up to my standards.”

  Jack was quick to remedy that, making me hold my breath for a few moments as I felt them slide into me. I still would have preferred Simon’s cock, but when he rotated his hand so his thumb was back on my clit, I didn’t really care all that much anymore.

  Meanwhile, Simon reached for the lube, and Jack slowed down when he felt Simon’s finger at his asshole. He earned himself a slap for that which was loud enough to make me guess that it had been a hard, real one, making Jack lose his rhythm for a second, but then pick up to his former speed.

  “Ease up, then bear down on my finger. Unless you’re too sore from earlier?”

  “The only thing that’s sore is my ego,” Jack replied, pressing the words out between closed teeth.

  “We’ll see about that tomorrow,” Simon told him, and used his other hand to cup Jack’s balls.

  Jack moaned, and his thrusts became erratic until he found a way not to hurt himself fucking me, which turned out to be using deeper thrusts than before, as deep as he would go. Taken together with what his fingers were doing inside me, I felt my orgasm swelling, a sweet, bright light on the horizon.

  Jack really seemed to have less problems than I’d expected, judging from the way he obviously got worked up within minutes. Before long he was leaning further over me, panting into my ear in the most delicious way as he ceaselessly translated any of Simon’s motions into pushing into me. Maybe it was the sheer physicality of the moment, with the restriction of bondage just adding to it, or it was the fact that I felt so relieved that we’d somehow managed to find a way out of what seemed like a massively tangled situation this morning, even with a long way ahead still; whatever it was, it made my resistance dwindle, and before long, the sounds leaving my throat drowned out Jack’s.

  “Please…” I started, low under my breath, but Jack must have picked up on it, because suddenly there was a third finger pushing into me, and the thrusts of his hips gained momentum. “Please may I come?”

  “Already?” Simon asked, his usual teasing tone immediately making me bite the inside of my cheek to keep from groaning.

  “Yes!”

  “Oh, I don’t know about that,” he mused, taking his time with replying, all the while giving Jack time aplenty to increase everything he was doing to me.

  “Please!”

  It was easier this time to beg in Jack’s presence, maybe because I now knew that he’d seen me do it even when I hadn’t been aware of it, or because it had become a usual part of my routine. That didn’t change the fact that I was very close to that razor sharp edge, and two weeks without any rougher kind of tumbling had taken their toll on my ability to hold back, too.

  “What do you think? Shall I let her come already?”

  I wanted to reply even though I knew he was asking Jack.

  “I don’t know. Do you usually let her come this fast?” Jack asked between pants, and I would have loved to kick him for it, but I couldn’t even forcefully clench any muscles that would help him decide.

  “No. But I feel generous tonight. How about this? Erin, you may come as soon as I have my cock up Jack’s ass.”

  That made me want to throw a physical fit, but all I could really do was buck against Jack, who didn’t seem opposed to the additional stimulation. The worst thing about it was that it was completely out of my control or influence. I had no way of telling how much Jack had loosened up already, or how much time Simon wanted to take. What I knew for sure was that I couldn’t hold out much longer, although I tried my best to distract myself for the moment. Then even that failed, and I was getting frantic.

  “Please, you can’t do this to me, I can’t hold it any longer! Please let me come!”

  Simon just shook his head, grinning, making tears of frustration well in my eyes.

  “You know the condition. You don’t get to come unless Jack wants my cock in his ass. It’s not my fault that he’s too busy fucking you to give a shit.”

  Maybe if I’d not been half insane with the need for release, I might have thought of that earlier, but it took me another couple of seconds to decipher that.

  “Jack? Stop being such an asshole and ask him to fuck you!”

  “What, I don’t even get a single nice word?” He grunted, then had the audacity of sinking his teeth into my shoulder, almost making me lose control from the extra sensation.

  I gritted my teeth and closed my eyes, doing everything I could to hold out longer—rattling off lists in my mind, thinking about my octogenarian neighbor having sex—but Jack seemed determined to make me fail, judging from the way he practically ground the pad of his thumb into my clit.

  I sailed past that point of no return and knew that now it was only a matter of time before my body would start to convulse. Forgetting all about propriety and how I usually acted around Jack, I started pleading with him at the top of my lungs.

  I almost didn’t make it when suddenly he went completely still above me and grabbed my bound left hand with his right that wasn’t busy turning my genitals into the promised land. His forehead touched down on my shoulder, right where he’d bitten me moments ago, and he let out a low groan, followed by a rather emphatic, “Damn!”

  It was pretty obvious what that meant, and the moment he pushed forward, into me again, I let go. Bound as I was, with Jack’s fingers in my pussy and his cock in my ass, I couldn’t evade, couldn’t even move properly, which heightened the sensation of heat zooming through my entire body. Muscles locked and clenched, making me shake all over, while harsh breaths found their way out of my chest. It felt so fucking good that it was almost painful, and only got better when my mind cleared and I realized that Jack had started fucking me in earnest again.

  A quick look in the mirror revealed than his motions where shorter than they felt to my hypersensitive body, but watching him pretty much fuck himself on Simon’s cock, and thus also pushing into me, was mesmerizing and incredibly hot. My body calmed down a little but not much, the constant stimulation not letting the need inside of me ebb away. By the time I had caught my breath again, I was so fucking turned on that I likely would have had to start begging anew, only that Jack had ditched his manual stimulation so he could support himself better above me, lending me some matter of respite. Not that I necessarily wanted respite, but not feeling like I was about to explode any moment now let me appreciate the raw sensations every thrust brought with it, and that was satisfying on its own.

  Then Jack’s motions became less coordinated, and Simon finally took over, grabbing his hips and driving into him with slow, controlled rolls of his hips. I doubted that would have been enough to make me come, but then Jack was also getting massive stimulation from his cock still sheathed deep inside of me, and when he finally lost it, he came with a series of moans and grunts that was whipping my own libido back into a frenzy.

  Simon pulled out of him as soon as Jack stilled, and pulled off the condom with one hand while he leaned into Jack and nuzzled his neck playfully. Jack grunted something incoherent and moved off me, rolling onto his back, eyes wide and his chest still heaving.

  I half expected that Simon would just finish by jerking off, or maybe have me suck him off, but the telltale ripping noise of a new condom wrapper had me perk up and gave me about a five-second warning before Simon leaned over me, then picked me up and flipped me over onto my back. Normally he was pretty quick in undoing his own knots, but this time there was some extra needless jerking on ropes involved as he freed my legs, the bliss of being able to stretch those muscles the best thing I’d felt in a long time—until he pulled my hips toward him, put my raised legs up on his shoulders, and thrust into me hard enough that my entire body rocked into the mattress. Jack’s fingers had felt great, but now having Simon’s cock in my pussy was simply amazing, and he certainly didn’t hold back.

  He did lean further into me, forcing my legs to his sides and mak
ing my hips rock up to allow for deeper penetration, while one of his hands reached up and grabbed my breast, swollen, red, and sensitive from the ropes that had restricted blood flow for half an hour now. I started to moan, then cried out when he really dug his fingers in, squeezing hard enough to hurt, but not half as hard as I wanted him to. Grinning down at me, Simon increased his pace, fucking me harder, and before long he had me right where I needed to be again.

  Instead of listening to my begging, he shifted himself further over me until his mouth could reach mine and drowned out his own orgasmic shout by thrusting his tongue into my mouth and sealing my lips with his. I took that as a sure sign that I might as well go ahead, but it was the same to me as I couldn’t have staved off the second orgasm that rocked through me.

  It took me a little while to gather my stray thoughts. Thinking was hard, moving was hard, too, and I wanted to do neither. I felt sweaty and gross and awesome and warm, with one hot body half lying on me, another pressed to my side.

  Then there were eager lips seeking mine and I responded immediately by letting them in, then another mouth placing lazy, wet kisses all over my jaw and the side of my neck. Finger moves, teased, explored, but for the most part stroked gently, and then Simon rolled me onto my side so he could start undoing the rest of the ropes. I complied automatically but never stopped devouring Jack’s mouth until the restriction around my torso lessened, and a tingling, burning kind of sensation spread through my tormented tits.

  I tried reaching up to cradle and massage them, but hands batted mine away, and when I tried again, Jack and Simon each grabbed one of my wrists and pushed them into the sheets next to my head, then went back to work, kissing and licking and sucking the pain away. It took a while, and they didn’t stop when my hisses turned to needy moans. I was too tired and spent to keep my eyes open, so I had no idea whose hand reached between my thighs and started masturbating me to a third climax, one that I didn’t even think to ask for.