Caught in the Middle

by Kira Barker

  “Definitely an improvement, but I’m not sure that will be enough,” Simon remarked as he withdrew his hands, then used more wipes to clean his fingers than seemed strictly necessary.

  I wasn’t sure if he wanted my input on that, but I couldn’t really come up with anything until he walked to my side and hunkered down next to me again. Now he didn’t focus on my face, but somewhere lower on my body. I got my answer to that question when he reached for my breast, getting a good grip and squeezing before his fingers found my nipple. I hadn’t really missed being touched there until now, but as such things went, I immediately rued the loss of contact when he withdrew his hand.

  “How sensitive are your nipples?”

  I really didn’t know how to respond to that.

  “Kind of lacking comparison here, but not too sensitive, I guess. Why?”

  Suspicion laced my voice, and Simon’s grin was enough to make me want to wrap my arms protectively around my boobs. But that was, of course, entirely impossible with my arms tied down, leaving my breasts completely at his mercy.

  “That needs to be remedied. Your lack of comparison, I mean, not your constant need to sass off.”

  Reaching into the pocket of his pants, he pulled out a chain, and when I saw what was attached to both ends of it, I tensed without intending to.

  “Oh, don’t worry. They don’t hurt half as much going on as they do coming off,” he tartly informed me as he reached for my breast, then fixed the clamp around my nipple.

  Bracing for pain, I was almost disappointed when the actual result of the jaws of the clamp closing wasn’t too bad, also not on my other nipple, either. The paddle was decidedly worse.

  Stepping back, Simon eyed the result critically, then crouched down right in front of me, a terribly amused look on his face.

  “I think part of what ruffles your feathers so much is that you’re forced to be so passive. Maybe a more active role will spice things up for you?”

  I wondered if I should point out that I still wasn’t bored, but his statement made me frown for another reason.

  “You tied me to a bench. How can I be anything but passive?”

  “The devil is in the details,” he observed, then picked up the chain that connected the nipple clamps, and using his other hand, pulled it between my upper arms. The sudden increase in tension that quickly turned to pain made me hiss, but that didn’t seem to deter Simon one bit.

  “Open your mouth.”

  I did, because with him yanking on my nipples like that, I felt disinclined to antagonize him. He pulled harder on the chain, which made me gasp, and carefully pushed it over my chin and into my mouth, making the sleek metal press into my cheeks. Immediately, I put my head down, trying to alleviate the pain, but that only resulted in the chain dropping from my mouth when the slack increased. My pulse spiked when I realized what had happened, but try as I might, I couldn’t manage to pick it up with my teeth once more as the motion inevitably made my body move, and the chain slide back onto the bench between my arms.

  “Don’t do that again,” Simon warned with gleeful malice in his voice as he retrieved the chain and put it back between my lips. He immediately grabbed my chin, forcing my head to remain bent back, the pain in my nipples a red hot flash that made thinking hard. I squirmed, but that only worsened my predicament, so I made damn sure to remain immobile while he kept staring into my eyes.

  “Let’s play a little game. You obviously like the flogger, and I think you’ll enjoy the paddle, too, but as this is your first time getting worked over well with either, I think it’s just fair that I give you a means to tell me exactly where that point is between pain that feels so damn good, and pain that doesn’t. See, I’ll even give you some of the power back that I’ve so sneakily acquired by tying you up like this.”

  Somehow I got the feeling that this had nothing to do with fairness, or mercy for that matter. He confirmed my guess as he went on, forcing my chin even higher.

  “The rules are easy. As long as you can stand me hitting you with the flogger or paddle, you are allowed to keep your head down, thus keeping the strain on the clamps to a minimum. Once you grow tired of that, or it simply becomes too uncomfortable, you just need to raise your head, and I’ll give you a break. When you’ve had enough of that, drop your head, and flogger or paddle it is again. Sounds like so much fun, doesn’t it?”

  I only took a moment to stare at him when he let go of my chin, then quickly dropped my forehead onto my arms, doing my best to maximize the slack in the chain, now securely between my teeth. Even then my nipples still hurt, but the sensation dimmed to the point of being the lesser of two evils when the flogger hit my back moments later. That wasn’t so bad, particularly as Simon took it easy for a while, but that mostly served to make me suspicious. It felt too much like he was biding his time, and I already knew that there was no way in this that I could actually win.

  His focus soon switched from my back to my ass, then thighs, then he exchanged the flogger for the paddle. Before, he’d just hit my ass with it, now he also brought it down on the top of my thighs, and that made me realize that I actually preferred that more compacted kind of contact, at least until he put more force behind it. I felt that balance he’d been referring to slide toward the uncomfortable part of pain, but still tried to hold out as long as possible—until the next slap hit me squarely between my spread legs, making me scream and jerk forward. The dull throb in my nipples increased to hot pain before I realized that I’d jerked my chin up, panting loudly around the chain that I thankfully still gripped between my teeth.

  “Thought that would get your attention,” Simon let me know way too sweetly as his fingers slid over my still-stinging flesh, finding my clit again.

  Even with the pain in my nipples, I relaxed, then realized that it actually factored well into the heady lust spreading through me. It was a little too strong, too stark to fully enjoy, but it did something to me that I hadn’t expected. Exhaling shakily, I closed my eyes and let myself fall deeper into the sensation.

  A minute passed, then two, and for a little while I was getting a little concerned that I might have to resort to asking for that pesky permission to come, but then the discomfort in my nipples turned to agony and I reluctantly let my head droop again. Immediately Simon’s fingers stilled, but his hand remained cupping my sex a little longer before he withdrew it with a not-quite gentle slap.

  Oh, but he clearly had found himself a new favorite target.

  I fully expected the paddle, and likely harsh enough to make me jump as much as my bonds would let me, but instead it was the many strands of the flogger that came down on my pussy, bringing a lot of weirdly enticing air and a contact that was soft enough to make some of the tension leak out of my weary legs. Of course he didn’t keep it to such a low, comfortable, almost teasing level for long, but even when he increased the force with which he sent the flogger straight for my labia and sometimes even my lower stomach, it wasn’t just easy to bear but made me yearn for more.

  And then it was the paddle again, steady, fast and increasingly more forceful, but even with a different sensation, the result didn’t change so much. It felt good, actually great, to the point where I did my best to push my ass farther into the air to give him better access. Everything except the paddle coming down on my pussy dissolved into the background static of my mind, with only my nipples remaining as two unsteady blips of awareness. Soon it was impossible to concentrate on anything else, and he just kept on going and going and going…

  Until three successive hard smacks that came with enough force to rock my body tore me right out of that floating space, making my eyes go wide as I screamed, unable to give a shit about the chain any longer. Dumb luck let it remain between my lips, and once I could think past the blinding pain radiating from my pussy, I raised my chin jerkily enough to put some extra insult to the pain I inflicted on my poor nipples.

  My mind was too addled to react properly, so I didn’t shy away at all
when his fingers cupped my still-aching flesh, massaging it slowly rather than doing something directly stimulating. Not that it wasn’t stimulating now that agony had dulled to ache, feeling like a hyper aware second heartbeat between my legs.

  “Good girl,” he praised again, and I could hear the smile in his voice. “I think now you’ve earned yourself that reward.”

  And then two of his fingers slid into me while his thumb ground into my clit, and I could have wept with gratitude. Maybe I was actually weeping, I couldn’t say, with sweat stinging in my eyes, and now drool leaking out of my mouth. Very appetizing, but I really didn’t give a shit, because there were two fingers fucking me fast and hard, sensually rubbing against the plug that made everything so much more intense and tight that I felt my climax rolling over me as if it had slapped me in the face out of the blue. Tensing all over, my head dropped, more as a reaction to the wave of need sluicing through me than anything else, and his fingers slid out of me again.

  Breathing heavily, I felt my pulse skyrocket as I waited for the inevitable—scolding, followed by more of that paddle, and I doubted that any kind of head jerking would bring relief now.

  Instead, the telltale sound of a condom wrapper tearing was loud in the silence, then I felt Simon half-climb onto the bench behind me. I didn’t react at first when I felt his cock slide up and down my slit, but then he thrust into me, making my breath catch in my throat for entirely different reasons than before. Shit, that felt so fucking good!

  Getting finger fucked should maybe have been a clue, but feeling his cock in me now make me realize just how much my position and the butt plug tightened up my vagina. The sensation was somewhat reminiscent of last Saturday, but with everything else going on, mainly the dull aches coming from all over my body, it was hard to relate. And really, once he picked up his pace, I didn’t care whether he was just lenient with me, or I’d actually managed to sneak that orgasm by him. Right now my body overruled my mind, forcing it to focus entirely on the sensation of getting fucked deep and hard.

  Maybe it was because I’d only just come, but it didn’t take long for tension to ratchet up again, and this time I felt almost obliged to do him that favor and beg. I still waited until I felt there was no way around my release any more, which was a good thing, because the moment the first “Please!” made it over my lips, he stopped and pulled out, making me scream in frustration.

  “Not so fast, slut,” he ground out, and slapped both of his palms flat down onto my ass cheeks. Compared to what had come before, that didn’t even sting.

  Grunting in frustration, I tried to move back to grind myself against his cock, even though I doubted that this way I could make him slide back into me. Simon quickly disabused me of that notion by grabbing my hips and holding me steady, and only let go with one hand when I finally stopped pushing against him.

  I felt a brief tug and the plug slid out, leaving my ass with a weird sensation as air rushed in before my sphincter clenched shut again. There was certainly enough lube in evidence not to need a refill now—something I was really grateful for in hindsight—and he didn’t hesitate, but grabbed his cock and aligned it with my anus before starting to work himself into me.

  On Saturday, Jack had been very diligent in prepping and spreading me open, and I’d enjoyed that as much as I’d dug actually feeling his cock inside me. Now I think I would have gone insane if Simon had dragged things out, and, bless him, for once he didn’t do everything possible to drive me up the walls. The shallow thrusts he used were slow if deliberate, but the moment he felt my body yield, he pushed harder while pulling me closer with both hands on my hips again.

  There was some discomfort and maybe a little pain, but when he started fucking me in earnest, all that got swept away by one of the most incredible sensations I’d felt in my entire life.

  “Keep that chain in your mouth,” he warned, then grabbed my hair and wrenched my head back, making me yowl with pain and surprise both. Yet again that got swallowed quickly, paling compared to everything else.

  And wouldn’t you know it, as close as I’d been before he switched things up, I was rather quick to find myself in the very same predicament yet again—and this time, I didn’t hesitate.

  “Please let me come! Please! Let! Me! COME!”

  The bastard actually slowed down a little, making me grunt in frustration until he let go of my hair, his chest partly leaning against my back while his hips were still doing most of the work.

  “Wait,” he warned, his voice raspy and hot against my neck.

  “Please! I can’t…! You have to…! I…”

  “When the clamps come off, you may come.”

  He only left me with a split second to process that before his hands groped for my breasts, and another while my mind caught up to the fact that blood rushing into previously constricted tissue might come with some additional discomfort. Then the clamps were off, “additional discomfort” proved to be the understatement of the day, and I came so violently that I jerked up hard enough to drive my shoulder into something that didn’t feel like muscle only. But Simon didn’t falter, not for a second, and drew out my climax by continuing to fuck me steadily.

  I felt like I came crashing down when the haze of lust cleared, my aching nipples like two clear pinpricks of centered attention, but then Simon’s hand slid from where it had been back on my hip to between my legs, zeroing in on my clit with determination. And, just like that, the next wave started building, or maybe it was still an extension of my last orgasm—I really didn’t care. With the chain now useless, I spat it out, buried my face in my arms, and started my litany anew.

  “Let me come, please, let me come!”

  “So soon again?” Simon taunted, or tried to, but almost out of breath as he was, it could have been a note of surprise, too. He certainly didn’t slow down, but instead slid the fingers that had been busy worrying my clit down to thrust into me, and used the ball of his hand to keep friction going where I needed it the most.

  “Please!”

  “Hold it. Hold it, I said!” he shouted when he felt me start to shiver underneath him.

  Biting the inside of my cheek hard, I tried to hang on, one more second, one more…

  “You may come after I do,” he ground out, already thrusting irregularly, and two jerks later he stilled deep inside of me, while his fingers fucked me frantically.

  That third orgasm wasn’t as hard as the one before but still sent me screaming, my entire body alive with need. Simon’s fingers kept going until I sagged underneath him, spent and shivering and smiling wide enough to hurt my cheeks.

  The very small part of me that was still checking in with the world and not soaring in the clouds noticed that Simon was rather quick to shake off his own post-orgasmic haze, and set to undoing the ties that kept me fixed to the table with the condom still hanging from his cock. I might have snarked about his priorities, but then he was done getting the ankle ropes untied and helped me to lie down and stretch out my legs, and that felt so fucking wonderful that any desire to give a speech dissipated into contented relaxation. The ties that held my wrists followed, and last came the rope that held my arms together, leaving me draped over the bench, half on my back, half on my side, unwilling to move a muscle except to maneuver myself into an even more relaxed position. Simon grinned down at me briefly before he took care of that condom, then returned to me and leaned against the bench in the vicinity of my hips.

  “Congratulations! You survived,” he offered, smiling.

  “Are you sure? Because I’m not sure I can feel my legs,” I joked, instantly ruing my words when he reached behind him and pinched the fleshy part of my thigh.

  “Seems responsive to me.”

  He laughed, deflecting my feeble attempt of swatting him. I made a face, then let my eyes roll back to stare at the window above me, not really seeing the clouds streaming by. Simon caught my hand where it now rested idly on my thigh.

  “Wrists are okay?”


  “Perfect,” I purred, then raised both arms to look at the already fading impressions the ropes had left. “Although I’m not sure I would have noticed if my fingers would have fallen asleep. You had me a bit preoccupied there.”

  Simon answered that with an even brighter smile.

  “You’re a tough cookie, you know that? I didn’t really expect I’d get to use the paddle much except to scare you, but not protesting here.”

  I couldn’t help crack a smile on my own, feeling a little stupid how proud his words made me feel.

  “Again, I’m missing data to compare it to, and this time there’s no reason to help me out there right now, mind you, but at least to me it seemed as if you got some mileage out of my ass.”

  If I hadn’t been quite so physically exhausted, I might have face-palmed myself then, but as it was, I got to see the full glory of his smirk.

  “That I certainly did.”

  “You know what I mean,” I accused.

  “I do, but it’s nevertheless the truth.”

  Scrunching up my nose, I pulled one of my legs up onto the bench, then shifted, trying to catch a glimpse of my ass.

  “Just how bad does it look back there?”

  “Nice and red,” Simon confirmed, then put his palm almost proprietarily onto the aforementioned war zone. “A little warm still, but in an hour or two you won’t see anything anymore. Maybe you’ll feel it a little when you sit down later, but there’s no deep tissue bruising and no marks.”

  That astonished me a little, because some of the fingerprint-shaped bruises from Saturday were still in evidence, if fading now, and what little manhandling the guys had done while they had me between them was laughable compared to what Simon had put me through today. Just thinking about it made me blush, although I wondered if that was even visible, with my face likely still red and blotchy from exertion.

  “Surprised?”

  “Kinda. A few of those strokes felt like they should leave marks.”