Caught in the Middle

by Kira Barker

  Simon’s return on mostly silent feet brought my attention back to him. He seemed faintly amused, but the look on his face turned more stern as he caught my gaze. From the edge of my vision, I could still see that he was carrying a medium-sized flogger in his left hand, the leather strands trailing down to his knee.

  “Don’t squeeze too hard. He won’t like that,” he advised.

  Before I could make any sense of that, he brought his arm back, then sent the strands of the flogger flying for my leg. They hit me mid-thigh, not very hard, the contact more tickling than actually painful. Inadvertently, I shrank back even thought I tried not to, and my grip constricted, prompting Jack to give my breasts a rather harsh squeeze in between the mostly sensual massage they’d been receiving so far. When Simon hit my other thigh just a little harder, I managed to constrain any tensing to above my wrists.

  The next time the flogger made contact with my body, it actually stung, the fourth time the sensation was mildly painful. I tried to steel myself somehow for it, but my concentration was so frayed between the new sensation and everything Jack was doing to me right then that it was almost impossible. It didn’t really matter, I found out with the next, now decidedly harder impact of the leather strands with my leg, because the pain didn’t distract me from the need scorching through my body—no, it clearly added to it.

  Simon kept going like that for about a minute, regularly looking at my face and judging my reaction between taking aim. I was sure that by the time he stopped, my thighs must have been red—they certainly felt warm with a light burning sensation radiating from them. I relaxed, feeling just a little proud of myself for not uttering a single sound.

  I probably looked a little smug, too, because something changed in Simon’s eyes, and before I could brace myself, he used his free hand to slap me firmly between my legs.

  It was definitely discomfort rather than surprise that made me grunt, but before that had even properly registered, his fingers were back inside me, and not just probing like before. Unlike any other guy who’d ever touched me before, he seemed to know exactly in what direction to move and where to press, causing freakishly strong sensations that threatened to buckle my knees. Jack’s hands moved back to my upper arms to support me, and while I immediately missed the contact, I couldn’t quite bring myself to care when Simon’s thumb found my clit.

  “Holy fucking—” I started hissing between my teeth, but cut off when Simon dropped the flogger and wrenched my head back by my hair again. Leaning in, his mouth was tantalizingly close to mine—close enough to kiss—but the way he stared at me told me rather plainly that he had no intention of doing that.

  “My, my, aren’t you a horny little slut? If I’d thought I’d get you to almost come that quickly, I would have set this up differently.”

  His fingers didn’t still then. No, they sped up, and all I was capable of was a terribly embarrassing sound between a moan and a gasp.

  “Do you think I should let her come already?” he asked Jack conversationally, getting a low chuckle in return.

  “I don’t know. Do you think she deserves to come?”

  For that he deserved a harder squeeze from my fingers, but that only made him laugh.

  “No, I think she hasn’t really worked at all for that privilege,” Simon mused, then had the audacity to grin in my face. “But you should know that you only get to come when you beg me. Understand?”

  Gritting my teeth, I made the stupid decision not to reply right away, and only got a moment to regret it. Instantly he withdrew his fingers, making me feel terribly empty, but before I could react, he slapped my pussy again. If it had stung before, now it hurt, the next, even harder slap making me cry out as I tried to wrestle myself free from Jack’s grasp. Without me really noticing, he’d turned his supporting grip into something very much like a vise and had stepped back far enough to let his cock slip out of my hand.

  Simon paused for a moment, and this time I wasn’t dense enough to be stubborn.

  “Yes, I understand, Sir!”

  Part of me wanted to plead for him to stop, but I bit down hard on my tongue to keep myself from that. It was hard enough to manage to keep my thighs apart when all I wanted to do was clamp my legs together, but I didn’t doubt that such a maneuver would come with an even stronger retaliation.

  “Good,” Simon said as if nothing whatsoever had happened, then let go of my hair so he could bend over and pick up the flogger again.

  My breath was coming in harsh pants, and it took a few more seconds for the pain to subside, but that left me very conscious of the fact that I was still worked up as hell. How I could be so turned on by something like that was a detail I chose to ignore for now, but then it fell right in line with everything else.

  “Turn her around.”

  At Simon’s direction, Jack eased his grip on me long enough to let me flip around at his nudge, coming to face him now. He flashed me a smile as he wrapped his fingers around my arms again, then pulled me flush against his body so that my breasts were mashed against his chest. My chin almost collided with his collarbone before I steadied myself, and I quickly widened my stance when he whispered a soft, “Legs,” into my ear.

  Then the flogger bit into my left ass cheek, just as hard as Simon had hit my thigh before, making me buck into Jack before I could brace myself. Jack chuckled under his breath and pushed his hips forward, causing his cock to rub against my lower belly.

  “That eager, are you, hm?” he remarked, and for a split second the usual impulse was there to bite his head off. Not even the flogger assaulting my other ass cheek helped.

  Surprisingly, Jack nudging my face slightly with his nose before his warm lips pressed almost sweetly against mine did the trick.

  The intimacy and sheer gentleness of his kiss astounded me, enough so that it took me a moment to react when his tongue moved against my lips, seeking entrance. The flogger hit me just hard enough to make me wince, thus opening my mouth, and Jack took that as a welcome invitation to proceed. My mind caught up then and I deepened the kiss, losing myself in it just for a moment.

  Then I noticed that Simon had broken his rhythm and stopped, distracting me again. I really didn’t want to break the kiss, and besides, I couldn’t really turn my head well in this position anyway, but I was instantly suspicious. That was likely the reason why I didn’t jump when his palm came down on my ass instead of the flogger, but the new sensation made me moan into Jack’s mouth.

  Simon picked up a steady rhythm, hitting each cheek five times before moving to the other. More than one moan and a few grunts escaped me, but Jack swallowed all of them. Maybe it was that distraction, or maybe it was the different sensation that let my body cope much better, but by the time Simon stopped and Jack pushed me away, my mind was once again reeling with need.

  Jack looked a little worked up himself as he smiled at me, then flipped me over again so that Simon could grin into my face. I tried not to react, but that was impossible, even more so when Simon took the chance to lean close himself and capture my lips hungrily with his.

  Jack’s kiss, even when it had become more heated, had still retained that sweetness. Simon’s was different somehow, more demanding but also tantalizingly teasing. I made a sound low in my throat when he moved back the second time, only to capture my bottom lip between his teeth and suck on it before letting go.

  My erratic breathing rhythm had slowed down somewhat in the brief respite I got, but I knew that was over when I caught the gleam in Simon’s eye. No doubt, he enjoyed himself quite a lot when he reached between my legs, and after only a cursory tickle over my clit started slapping my pussy once more.

  My first reaction was to try to shy away, until I noticed that he’d moderated the force behind each slap to where it stung, but also felt strangely enticing, almost pleasant. It took me a little while to come to grips with that realization, and a little longer still until I could make myself relax into the steady rhythm. Simon stopped looking away from my
face so he could hold my gaze—his aim was steady enough for that—and seeing him watch me with that intensity only added fuel to the flames.

  He stopped eventually, which instantly made me yearn for more, but he didn’t give me a chance to dwell on that. At his nod, Jack let go of me, and Simon reached for my hair again, if a little less forceful than before as he turned my face up to his. I had to admit that, even though it hurt a little, I really liked that, too.

  “I think you’ve been lazy long enough. Time for you to show some gratitude.”

  His words confused me, but when he let go and instead reached for my shoulders so he could push me down into a kneeling position, I got an idea of what he might be up to. Sure enough, he reached for the button of his jeans, opened the fly and pushed the denim down to his thighs, letting his cock see the light of day. Unlike Jack, he wasn’t completely hard yet, which made me wonder just how much of a distraction coordinating everything must be for him.

  Kneeling, with my thighs spread and my wrists still locked together behind my back, there wasn’t really much I could do, but I dutifully opened my mouth, because what else was there to do? Besides, he really had a nice cock, and if I couldn’t touch it with my hands, it was only fair to give it some attention with my lips and tongue.

  “Good girl,” Simon muttered, then stepped closer and reached for the back of my head. I was surprised that I felt more puzzled than irritated by the unlikely praise, but then his dick was close enough for me to reach, and I closed the distance quickly so that I could swirl my tongue over the glans and then take him into my mouth as far as I could.

  Simon groaned, his fingers threading deeper into my hair, and he pulled just enough on my roots to signal me to get going. I set to the task with as much alacrity as I could muster, which, in all fairness, wasn’t that much.

  I’d never really given much thought to giving head, mostly because it had never really done anything for me. Sure, most guys expected it, and if they were ready to go down on me I felt obliged to reciprocate, but that had been the extent of enjoyment for me so far.

  Today was definitely different and turned even more so when Simon let out a low moan, then bunched up a good portion of my hair in his hands and actively started to guide my head, rather than let me set the pace.

  He had a perfectly proportioned cock, and I was happy that, besides a hint of clean sweat, all my nose picked up was that purely masculine musk, but that wasn’t it. Physically, there wasn’t much difference, but in my head this felt completely detached from any other blow job I’d ever given. Maybe it was because for the first time ever I got to this place already so worked up and horny that I was sure I would come embarrassingly fast the next time anyone stuck anything up my vagina. Maybe it was entirely in my head—the whole setting, the fact that I was restricted in my movement by the cuffs, the knowledge that I had to keep my legs spread because I had been told to. Or maybe it was the simple fact that, technically, I wasn’t sucking him off so much as he was fucking my face, now holding my head steady while thrusting his hips forward.

  Whatever it was, I really didn’t give a shit. It was a fucking turn-on and I loved it, and everything else was secondary.

  Then Simon’s grip and rhythm changed, and the next time he thrust into my mouth, he went in deeper, bumping into the back of my throat. Immediately my gag reflex came alive, making me want to buck away, but that wasn’t quite that easy with the way he kept my head in place. I coughed, or tried to, tears welling up in my eyes. A moment later he eased up, only to try again with similar results. This time he let go completely, giving me a chance to pull away and clear my airway until I could breathe freely again. The use of my hands would have been nice, but since he made no move to disconnect the cuffs, I had to make do with rubbing the spit that had ended up on my chin all over my shoulder.

  I didn’t get a chance to do more than glance up at him before he caught my head once more and resumed fucking my mouth as if nothing had happened. My pulse was still elevated and only dropped slowly, but before long he told me to take a deep breath and tried again.

  I was so not the queen of deep throating, and for the first time ever I actually cared about that.

  “I think you need a distraction,” Jack said from somewhere surprisingly close to me. Then his hand was on my ass, making me rise into a higher kneeling position, and before I fully registered what was going on, he was pushing his head between my legs while maneuvering me back with his hands on my thighs until I was effectively straddling his face. When I looked down, he flashed me a grin, then grabbed my hips and raised his head. For a few seconds straight, the ability to think pretty much fled my head.

  But, damn, he knew how to work that mouth!

  When I managed to get a grip on myself again, I realized that Simon had let off, but when I looked up at him now, he pointedly stared down at his now thoroughly hard cock.

  “Suck me off, slut. I don’t care how you do it, but you better get the job done fast.”

  I flashed him what I hoped was a hungry grin, although it got thwarted midway when Jack did something amazing with his tongue on my clit, but Simon didn’t seem to mind my indecently loud moan. He did lose patience, though, and grabbed my head, against his previous direction. I really didn’t mind.

  And when he came down my throat a good five minutes later, I was more than happy to swallow.

  If I’d thought I’d been worked up before, I was borderline crazy with need by the time Simon pulled me—rudely—off Jack’s face and pushed me toward the sofa, where I ended up in a half-crouched sprawl. How I hadn’t come yet was beyond me—likely overstimulation—and Jack had done his part to tease and lick but never quite fulfill what he was promising. He also looked rather smug as he followed us, then plunked down onto the sofa behind me, completely ignoring my death glare. Somewhere along the line he’d lost his clothes, but I didn’t really feel inclined to stare at all that muscle, tanned skin, or the black lines roving up his right bicep to his shoulder right now.

  Tired from kneeling for so long and with my arms still locked behind my back, I was kind of helpless as he pushed me around and rolled me onto my side, then had me pull my knees up toward my chest. I stopped wondering what that was all about when I felt his finger, cool and slick with lubricant, stroke over my anus.

  Reason, and more medical experience than I liked to admit, told me to relax, but instinct made me tense up. It didn’t hurt when he started easing one finger through my sphincter, but then the dreaded burning sensation started up, making me clench in earnest.

  “Easy there,” Jack cooed as he removed his finger, only to return with an even more liberal amount of lube. His other hand found mine, letting me hold and squeeze it, and when he tried again, it went marginally better. “Just bear down on my finger if you can’t relax. It will get better soon.”

  I wanted to snap at him that I knew exactly what I should do, but held my tongue instead. Not because of Simon’s warning this time, but mostly because my mind was still too frayed to come up with the eloquence required for our usual banter. That realization made me smile, which turned into a wince when Jack’s first digit made it fully inside. But he had been right; it got better from there, also because the wave of need inside me receded slowly, letting me unclench other muscles in the general periphery.

  The couch dipped on my other side, and when I opened my eyes, I looked right into Simon’s face. He was naked, too, and still soft thanks to my not-quite-superior skills, but I had a feeling that by the time Jack was done with me, that status would have changed, too. He seemed more at ease than before as he settled onto his side, then leaned over me to steal a kiss while his hand skimmed from my shoulder down to my breast.

  I tensed briefly when I felt Jack add a second finger to the first, but it didn’t take him long to open me up enough to let me enjoy the intrusion. Simon did his part to make me relax, his mouth now kissing a trail down to my breasts while his hand slid over my stomach and between my half-parted legs. />
  “This isn’t your first time anal, now, is it?” Jack ventured a guess as he sped up, and got a low moan from me in return.

  “Third. And that’s part of the problem, I think.”

  “We have all the time in the world,” he assured me, then laughed when I practically jumped when Simon’s roving fingers reached my clit. “Well, we do—you don’t.”

  A terrifyingly true statement, I realized, when Simon didn’t linger for long but instead slid one probing finger into my vagina, perfectly in sync with Jack’s. Muscles clenched and need surged, and I almost came right there. The problem was, neither of them seemed inclined to stop, and my brain was very happy to inform me just how good it would feel if it wasn’t just fingers penetrating me, but cocks.

  I realized that I was about to come, and this time I wouldn’t be able to hold back anymore. Quite frankly, I felt rather disinclined to try. So far there’d always been something to distract me, but now everything just added up to drive that wave higher and higher. The way the skin on my thighs, ass, and labia was still warm and sensitive from the spanking; Simon languidly sucking on my nipple; their fingers going deeper and deeper, spreading me open while rubbing against each other through the thin layers of skin in between; and not to mention the mental impact all that had on me, and I lost the battle before I even realized that I’d given up on it.

  What I hadn’t factored in was that other people were keeping better track of my reactions than I was.

  I was just about to come—moments, less than seconds away at the most—when Simon withdrew his hand, and Jack’s followed suit immediately after. That left me hanging, high and absolutely not dry, an infuriating inch away from my orgasm.

  “No! No no no no no!” I muttered under my breath, then tried in vain to somehow wrench my hands free to finish the deed myself, but of course that was impossible. I felt Simon’s almost silent laughter against my tit before he bit none too gently into it, then got up in one swift motion.