Dreamspinner Press Year Five Greatest Hits

by Tinnean

“Show me?” he asked.

  I thought I got it—he didn’t want to go poking around without me there, although the place was almost unrecognizable from my old home.

  “She’s cleared nearly everything,” I said as I led him through to the bedroom. The mattress was bare, four pillows neatly stacked at the end. Will nodded.

  The closet did have one packing box left, and I pulled it out to start assembling it.

  “This all yours?” Will gestured to the few clothes still hanging up.

  “Yeah,” I said. “I’ll check the drawers as well. I’m pretty sure I got most of it when I moved out.”

  “What about books and things? DVDs or anything?”

  “Living room,” I said. “For whatever she’s left me with.”

  He snorted with laughter, then immediately apologized. “This situation must suck for you.”

  “It’s fine,” I said. “Honestly. I just want to be with you, and now I am.”

  “You’re so cute,” he teased. I grabbed his ass as he passed.

  It only took a few minutes to dump the last few bits of clothes into my packing box, and then I pulled it through to the living room to collect the things that Will had collated for me.

  “Is there anything else?” he asked.

  Silently, I took his hand and led him through the few rooms where I’d spent five years of my life. It seemed cold now, and so far away. I wanted to show him, in my own way, that this was sort of a metaphor for my life now—the old me was gone. I’d packed up the parts of my life that I wanted to bring forward with me, and everything else was irrelevant.

  “I’m ready to go,” I said as we closed the bathroom door.

  “Are you sure?”

  “Yeah. Let’s go.”

  WILL HAD called me when we were both on lunch and told me to answer him with just “yes” or “no.” I’d laughed and agreed.

  “Are you alone?” he started.

  My eyes fixed on Esther, my co-manager, slowly chewing on a mouthful of salad, looking like a cow as she blinked big brown eyes at me curiously.

  “No,” I said decisively.

  “Okay. Would you like a session tonight?”

  “Yes. Please,” I added as an afterthought.

  “Will you be finished before five?”

  “No.”

  “Before six?”

  I thought about it. “Yes.”

  “Okay. Meet me in the playroom at seven, then. You won’t see me when you get home, so don’t panic.”

  “Yes?” I said as an unsure question, not sure how else to answer him. Will laughed.

  “Yes, indeed. I’ll see you tonight.”

  “Yes.”

  “Bye, Jesse.”

  KNEELING ON the hard floor in the playroom, I was glad he’d told me I wouldn’t see him when I got home from work. I wasn’t entirely sure where he was. I’d come in as normal and showered, then wandered around naked for a half hour or so until I needed to head up to the playroom to be in position on time for him. I hadn’t seen him once.

  Despite his conspicuous absence, my Master still walked into the room right on time. He gently petted my hair while I kept my position strong, then walked to the stereo system to set some music on to play.

  When my collar was affixed safely around my neck, Master led me to the area where the rope and pulley system usually lived. I’d noticed the sling when I’d walked into the room, but being the good sub I am, I’d ignored it and put it out of my mind. I wasn’t quite sure how I was supposed to get into the thing, though.

  “Did you ever play trust games when you were younger?” Master asked. “When someone stands behind you and you lean back until you start to fall, and you have to trust that the other person will catch you?”

  “Yes, Master.”

  “The sling works in the same way. I’ve rigged it up and it can take a person of about three times your weight. But you need to relax back into it and trust that it will take you.”

  “I trust you, Master.” The words were unnecessary, he knew I trusted him, but it felt nice to say it.

  He stood behind me with his hands on my shoulders. Because of the way the sling was positioned, there was nothing for me to hang on to; I just had to do it. Really, when I fell, it wasn’t that far at all. There was still a little twist of fear that it wouldn’t catch me, though—just enough to keep things interesting.

  It was strangely comfortable, the thick, black straps supporting me where I needed it, but leaving areas exposed enough for me to really feel like I was floating. Master moved around me, shifting my weight and changing my position until he was happy that I was safe, and then he buckled my ankles to high straps, spreading and exposing me rather thoroughly.

  My tan leather cuffs were secured around my wrists, and he looped a long length of rope underneath me, securing each wrist to the other but with enough slack so that I could move them. I had a feeling I was going to be in this position for a while, but I didn’t mind. It was comfortable.

  “I would normally do this session with a sub a lot sooner than this,” Master said as he moved around the playroom, collecting an assortment of toys as he went. “Unfortunately, with you, I find myself often distracted.”

  I smiled and stayed silent.

  “I think, at least at first, I’d like to blindfold you for this.”

  “Yes, Master,” I said softly.

  “If you would like me to take it off, just say so. It’s going to be a fairly intense session, and I will, of course, respect your limits. Relax, sweetheart. That’s all you need to do for me tonight.”

  He kissed the end of my nose and wrapped the heavy black cloth around my eyes, gently lifting my head to wrap it around and knotting it on the side so it wouldn’t be uncomfortable. With my eyesight removed, I could sink a little bit further into my subspace, and for the first time I noticed that the music Master had chosen wasn’t thumping rock. Tonight it was a bit slower, jazzier really. Sensual and erotic, but still with a beat. It was nice.

  I jumped a bit when Master snapped a cock ring around the base of my dick, which was lying semi-erect on my stomach. He moved away again, and when he returned there was a soft thud of him setting something down before I felt him between my legs. I quickly realized it was his spanking chair; he was sitting down for a better angle to play with me.

  Master leaned in and pressed a soft kiss to each of my inner thighs, tickling the hairs on my legs with his breath. Then he kissed each of my testicles and gently licked the area underneath them. I was feeling quite relaxed and dreamy already.

  A wet, probing finger gently caressed the wrinkled skin of my hole, not pushing forward to penetrate, just stroking there to stoke my arousal. All the way from the base of my spine to my balls, that one finger worked the whole area, stopping to rub tantalizing circles where I wanted it the most.

  “Shh,” Master implored. “Relax, let it happen naturally.”

  I stilled the needy wriggling of my hips and tried to follow his instruction. After long minutes where he kept this up, adding more and more lubricant, finally the tip of one finger pushed achingly slowly into me.

  I’d been fingering my own ass for pleasure for years, but never like this. Even when he prepped me for sex, Master was always quick and efficient: one finger, two to stretch, a few pumps of the fingers, a third to be sure, twist them over to tease, fingers out, cock in.

  The tip of his index finger stopped right at the first knuckle. All the clenching in the world wasn’t making it move. Only with my relaxation did it push in further.

  I caught on quickly.

  Every time I started to tense up, Master would stop whatever he was doing. It was difficult to let go when he was being so deliciously teasing with me, but I got there eventually. He added a second finger, his middle finger, switching it out with the first with long, practiced strokes until I started wriggling for more again, and then he stopped.

  When he removed both fingers, I whimpered with the loss. The next thing I felt was c
ooler, definitely a toy and not part of him, just thicker than his two fingers. It was liberally coated with lubricant, and when the flared base hit my ass cheeks, my suspicions were confirmed—it was a butt plug.

  Whoa.

  A vibrating one.

  I got the impression he had sat back to watch me squirm, and, as I thought, he didn’t do anything while my stomach muscles clenched and my cock leaked warm fluid. I huffed in annoyance and sank back into the security of the sling and lay supine for a few moments, ignoring the toy.

  “Good boy,” he said at my submission. The toy was switched off and gently removed.

  I took the few moments to meditate and try to take myself deeper, where I was anticipating his will and relaxing in the way I knew he wanted me to. More lube was added to my ass.

  The pressure of the next thing barely registered—it was small, I knew that much. Only when the next thing pushed through the ring of muscle did I realize they were anal beads. I’d used them on myself before, but never with Master, and I was filled with mixed feelings of excitement and dread. Excitement, because I knew they could be fun. Dread, because I knew that they could be manufactured in a variety of ways, including vibrating, and large.

  The next three popped in with no problem at all. Master added more lube for the next one. Again, no problem. The fifth and sixth started to stretch me. The seventh made me grunt. Master gave me time to adjust before adding more lube for the next one. Remembering the lesson he’d been teaching me since we started the session, I forced myself to relax.

  I surprised myself with how easily the dreaded eighth slowly glided into me. There was no pain. No awkward tension like the smaller one before had caused. Just the delicious feeling of fullness and a lovely stretch as my ass opened to accept it, then naturally closed behind it.

  Number nine was accepted equally as easily. I nearly started to panic for the next one, but with one long exhale, I took myself back to that place of utter relaxation. It took longer for Master to push the last bead in; the pressure mounted against my asshole until I felt it start to stretch. I wanted to squirm and clench in my bonds, but that wasn’t what Master wanted of me. With a little pop, number ten lodged itself inside me.

  It was euphoric.

  I felt no need to vocalize anything; I just floated on the feeling of weightlessness and achievement as Master gently massaged my ass with lubricated thumbs. To have something that large inside me, and my asshole closed and containing it, was slightly strange. Even with butt plugs there’s always a certain amount of stretch, even when the largest part is inside.

  “They’re going to come out now,” Master said in a low voice after a few minutes. “Remember to stay relaxed. You can come if you want to.”

  There must have been a loop that Master pulled on because sure enough, the pressure started again from the other side, and the largest anal bead stretched out my asshole again.

  “Don’t push it,” Master warned. “Just let it happen.”

  It was instinctive to try and force the offending item, but with a little willpower I found that lovely relaxed place again and felt Master’s approval as the tenth bead popped out. The ninth came out equally slowly. As did the eighth. The pleasure was delicious, but I wasn’t about to come. He paused, letting me recover from the three largest beads, then suddenly, and without warning, the last seven beads were yanked out of my body in a series of clench and release contractions in my asshole, and I screamed as I came furiously all over my own chest.

  Master hummed in pleasure and my cock leaked even more as he proceeded to lick my skin clean.

  By the time he was done, I was just about ready to have him take me down, carry me to bed, and let me sleep for the next eight hours.

  His words, “Are you ready for the next part?” forced me to reevaluate the situation.

  “Yes, Master,” I said as soon as I was sure I was.

  His fingers returned to me. I wasn’t sore at all, not in the way I could sometimes be after a rough fuck. It was like my ass had been gently persuaded to take the intrusion and not forced, and that made all the difference.

  Master’s fingers found my sweet spot and slowly teased my cock back to life. I wasn’t fully hard, but the cock ring helped, and I’d get there soon enough. His third finger didn’t hurt, nor stretch me. When his pinkie tucked up inside me, too, I felt that old desire to fidget rise up again. Master held still until I relaxed; even I could feel it now, the conscious effort to stop clenching those muscles that I thought I had no control over. He used his other hand to add more lube. A lot, lot more lube.

  His hand changed shape inside me. It was only when I felt the tip of his thumb at my entrance that I figured out what he was attempting to do. Then I really did clamp down in panic. I was glad for the blindfold then—I didn’t want to see his disappointment when he realized I couldn’t do this for him.

  “You can do this,” he said, reading my thoughts. “Just find that place again.”

  It took some time, and some work, but I got there. He never stopped moving his fingers and gently teasing the rim of my asshole with his thumb, so when I reached that place he just needed to push forward a little bit and, completely to my surprise, it worked in with only the tiniest amount of pain. Less pain than when he fucked me.

  Deep breaths and that headspace where I wanted nothing more or less than to please him let me move past the next hurdle, which was him pushing gently further inside, over the widest part of his knuckles where I might have winced a little bit, but the headspace felt too good and pulled me back under before I had a chance to contemplate it.

  Master turned his hand just slightly, and I felt my ass close over his wrist. His whole hand was inside me. His fingers were still stretched out and long, grazing against my prostate, and he sighed softly and might have said “breathe,” but I didn’t hear it properly. When his fingers curled, my cock sat upright and started to pay attention again, and by the time I could feel his fist clenched inside me, I was building to another orgasm.

  “Jesse,” Master said slowly, authoritatively. “Are you okay?”

  “Yes,” I replied. “Yes, Master. Can I see?”

  “There’s enough slack on that rope for you to be able to reach up and pull the blindfold off,” he said in the same measured voice. I followed his instruction, awkwardly bending one hand up behind me to give the other room to stretch up to my face, while Master kept his hand absolutely still.

  My eyes readjusted to the light and focused immediately on his face. Fuck, he was beautiful.

  Clearly this was costing him a huge amount of concentration. His reddish hair was darkened with sweat and stuck to his forehead, his T-shirt had been discarded at some point so his chest was beautifully bare, and his eyes were dark with passion.

  And his hand. Fuck. It was inside me. Seeing it and feeling it together brought about a new intensity of pleasure. Slowly, so slowly I had to make sure it was real, his hand started to move. Over long minutes he built up a rhythm of measured thrusts, twists, and pulls that had me writhing again; the rules hadn’t changed, though, and those movements caused him to stop. Only when I was truly submissive, giving him only my body and everything that came with it, would he move.

  This time when I came, it was actually the most intense orgasm of my life. Which I would never have thought possible, since I had already orgasmed once in the session. I was too far gone to ask for permission, to warn him, or even to make any noise as his knuckles gently massaged my prostate, and I kept coming, waves and waves of it, over and over.

  I knew how to relax to let him pull out slowly; he’d already taught me how to do that when he removed the beads. I was slowly coming back from the amazing rush, one that was both mental and physical—the best kind.

  Master hadn’t come yet. With my eyes drifting half closed, he cleaned me up, then rose and came to stand at one side of my head.

  “This won’t take long,” he said with a smirk.

  His long, gorgeous cock had been removed
from the confines of his leather pants and his beautiful, talented hand was jerking it in measured, practiced strokes. I looked up at him from under lazy eyelids and opened my mouth, my tongue licking my bottom lip in anticipation.

  Some of his come hit my mouth. The rest painted my face, across my cheek and neck and chin. I licked off as much as I could and let him smear his leaking cock over the other cheek. It cooled as he released me from the bondage, and I made no effort to wipe it off.

  My knees didn’t work when I attempted to stand. My fantasy of him carrying me down to bed came true, although a detour to the shower proved a wise choice. We were both covered in sweat and lube and come.

  There was no doubt I was still floating from the intensity of the session as I curled myself around him in bed, shocked to note that we had been in the playroom for a number of hours as I glanced at the clock on the nightstand. It didn’t matter. I was about to sleep in his arms. Nothing else mattered at all.

  IT WAS rapidly approaching 5 p.m., and time to go home, but I was far from finished with work. I had a stack of paperwork from suppliers to work through and complete before I could finish for the day.

  There was a knock on the door to my office, and my co-manager stuck her head around the door.

  “Hey, Esther,” I said with a sigh.

  “There’s a rather ridiculously handsome man out front asking for you. Says his name’s Will.”

  I grinned, despite my tiredness. “Would you let him in? I’m up to my eyeballs in shit right now.”

  “Sure. Can I ask for his number?”

  “No, Esther,” I laughed. She pouted and disappeared.

  I tried to pay attention to my paperwork, but the knowledge that Will was somewhere in the building made my insides all squirmy. There was another light knock at the door, and I called out for them to “come in.”

  He shut the door behind himself and walked over to me with the calm confidence of a man who knew he was fucking sexy.

  “Hey,” I said, pulling his mouth down to mine for a long kiss.

  “How’s it going, baby?” he murmured as we parted. He dropped lazy kisses down my neck.