A Masochist's Adventures in Wonderland
Chapter 25
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I was still lying on my side on the couch when Ash peeled himself out from behind me, climbed off the couch while I still lay there, and started moving around his apartment. I didn’t look to see what he was doing.
He came back over carrying a glass of water and sat down on the coffee table in front of me. “Sit up and drink some water,” he told me.
I heaved myself off the couch. My ass felt strange when I put my weight on it.
I took the glass and swallowed a gulp.
“How do you feel?” he asked.
My hand flew to my head and I rubbed my eyes. “Kinda foggy.”
“I meant your ass. How does it feel?”
“Different.”
“Does it hurt?”
I had to think about it. “Not really?”
He pulled a different butt plug out of his pocket and held it up in front of me. “I want you to use this during the week from now on. It will keep your stretched and open so your ass is ready for me whenever I want to use it. You don’t have to do it every day. Two or three times a week should be enough from now on.”
I looked down at the plug. It was bright pink and it was big—bigger than anything I’d ever used before.
It looked bizarre. It looked like some kind of circus prop—or the porn equivalent of one. Sticking that thing in my ass didn’t seem like anything any sane person would do.
I couldn’t let myself think that. I wouldn’t have used any butt plug on myself at all ever without Ash’s influence pushing me to do it.
His own words made the decision for me. He wanted me to do this so he could fuck me in the ass without hurting me.
Letting him down or denying him something he really wanted sounded worse than turning myself into some kind of sex freak.
I took the plug out of his hands, looked away, and mumbled, “Yes, Sir.”
“If you feel okay, you can stand up and put your dress back on. I don’t think you should do anything else tonight. Just go home and relax. Let your body adjust to what we did tonight.”
I put the glass down on the coffee table, got to my feet, and put the plug and the lube bottle in my purse before I tied my dress over my lingerie.
It still made me feel sexy in a hidden way. No one who saw me could see anything unusual about me.
He came over to me, kissed me, and we said our goodbyes. I went through the process mechanically not feeling much of anything.
I went home and put the new plug completely out of my mind before I went to sleep.
The following week passed uneventfully except for a few anal playtimes in the privacy of my own bedroom.
These playtimes didn’t differ from the others. I used the plug on my knees and worked the plug into myself from behind. I also used it on my back, sat on the plug, and worked it deeper into myself by rocking on it the way Ash had me do it that first time.
I always fantasized about Ash taking my ass the way he did during our last session. If anything, I fantasized about him taking my ass even more forcefully than he did then.
I started to fantasize about him holding me down and having his way with me anally the way I usually fantasized him doing it vaginally.
I didn’t know if he wanted me to take the plug with me to our next session or if that would just be my home toy from now on.
I put the plug and lube in my purse before I left. He didn’t give me any instructions on what to wear, so I wore casual clothes.
I found him sitting on the couch in his usual relaxed posture. “How did your week go?” he asked.
I nodded. “Pretty good. I can’t complain—unless you want me to.”
He didn’t take the joke. “I’m talking about my instructions to you to use that butt plug on yourself. Did you do it?”
“Yes, Sir. I did it.”
“Did you have any trouble with it?”
“No, Sir.”
He waved his hand at nothing. “Take your clothes off and go up to my room. Wait for me there.”
I dropped my purse on the chair and started getting undressed. So we were going back to his room.
I climbed the stairs and stood in the center of the room to wait. I didn’t know what to expect, but he seemed more likely to let himself go in this room than he did downstairs or anywhere else.
This was his personal private bedroom. He allowed himself more pleasure here. He went further, showed his animalistic side here, and connected with me more here. It was more intimate.
I faced the windows so I would have something to concentrate on while I waited for him to show up.
When he did, he started circling me the way he usually did when he was about to take our playtimes to the next level.
He cast a critical eye down my body each time he passed me. “Put your hands behind your head,” he ordered.
Raising my arms like this exposed me to his scrutiny. I kept my eyes down now. I didn’t want to see him scowling at me every time he walked past in front of me.
I wasn’t looking at him when he walked away. He did something behind me near his bed. He always seemed to take his toys out from under the bed. What would he use on me this time?
He came back over to me and stopped in front of me. I only looked up for an instant and immediately looked back down when I discovered his sharp eyes locked on me.
Unfortunately for me, looking down at the floor put me in a perfect position to see him attach a normal-looking clothespin to my left nipple.
This wasn’t one of the high-tech nipple clamps he used on me in the car. That one had a screw that adjusted the pressure and made it tolerable and even pleasurable.
This was the most ordinary, mundane, primitive wooden kind of clothespin my mother used to use to hang laundry on the clothesline in our backyard.
The wood bit into my sensitive skin. No force on God’s green Earth would ease the pressure when the pin closed its jaws on my nipple.
I gasped out loud and then whined in agony when the pain spiked into my chest. Ash completely ignored me writhing and squirming in front of him. He took a second clothespin from his other hand and attached it to my right nipple.
I had to look away when I noticed him holding four more clothespins in his hand. He planned to use them on me. I would have to be blind not to see that.
“That’s right,” he murmured. “Keep your hands behind your head. I want to see that you’re doing this of your own free will. I want to see you giving yourself to me because you want me to do this. I want to see that you’re mine to play with.”
I couldn’t stop convulsing in pain, but those words turned me on the way they always did.
I was doing this for him. This was what he wanted—to see me give myself to him—to anything he wanted to do to me.
Those words restrained me better than any rope or handcuffs ever could. I couldn’t put my arms down for anything—not if he wanted me to do this.
He walked away and came up behind me. I didn’t know what to expect and I didn’t dare to look behind me to find out.
He wrapped one arm behind me, leaned his mouth in close to my ear, and without warning, he laid his flat fingers on top of my clitoris and started rubbing.
“You’re going to be my little plaything tonight,” he breathed. “Do you know that? You’re going to be a little toy for me to play with the way I want.”
I thrashed and howled as the pleasure of his fingers mingled with the pain of the clothespins. I was his plaything. He really could do anything he wanted to me.
The influence he had over me kept me locked in place to stand here and take it. Even the pain seemed like another form of foreplay.
He worked me into a screaming frenzy before he pulled off and left me there wailing and crying out. The explosive combination of pleasure and pain racked my nerves—and it didn’t go away because the clothespins were still there.
He walked around behind me for a few seconds. I didn’t see what he was doing before he struck me across the hip and thigh with the same black leather flogger he used on me the first time.
He hit a lot harder now. The leather left a path of stinging tendrils running down the outside of my thigh, but it didn’t hurt nearly as much as the clothespins.
The flogger actually felt good by comparison. I probably would have protested him hitting me that hard with the flogger. Now it came as a welcome distraction from the agony of my nipples.
He delivered an identical cut to my other thigh, walked around in front of me, and fixed me with the same hawkish glare.
I trembled before that look. Here we go. It was all starting. He wouldn’t back down until he wrung every last drop out of me.
That look told me loud and clear that he planned to take me further than we ever went together before. Everything leading up to this moment had been child’s play.
He stuck the flogger handle in his pocket so the falls hung down the side of his leg.
Then he started clipping more clothespins in rings around the other edge of both of my nipples.
I screamed and thrashed and cried in front of him, but this mind-boggling influence he had over me wouldn’t let me put my arms down no matter what.
He kept glancing up at my face to make eye contact before he attached the next pin. Why did he have to be so ironclad determined about everything?
My shrieking and wailing meant nothing to him—except that it meant everything to him. This was exactly what he wanted from me. Was he getting hard right now watching me suffer?
He used up all the clothespins in his hand and left them in place when he walked away. I looked everywhere around the room and out the window for any help—but of course there was no help to find.
I had to look anywhere but at him. This pain pushed me to my limit.
He walked around me in those maddening predatory circles again, and this time, he slashed his flogger whenever he pleased.
He whipped it across my stomach from behind, down my back, on the back of my thighs, and between my legs on the insides of my thighs when he walked in front of me.
The nightmare really started when he stopped on my left and flogged the clothespins he just attached to me. He didn’t hit them hard enough to knock them off. He just hit them hard enough to make me scream out as more pain tore me apart.
He didn’t do it for very long—just long enough to show me that he could. These clothespins were nothing compared to the level of pain he could give me if he really wanted to hurt me.
He stopped with the flogger—and came back with another handful of clothespins.
He stopped in front of me and stood there for a long time just watching me spasm and jolt in all directions trying to cope with this.
His expression never softened, not even when he said, “I love it that you’re willing to do this for me. It’s such a turn-on to see you surrender yourself to me like this. You have no idea.”
He barely got the words out before he bent over and started attaching more clothespins to the rest of my body.
He started by attaching a row of clothespins to the thin, sensitive skin underneath both of my collarbones. These pins hurt with a completely different kind of pain. They didn’t have any flesh underneath to soften the bite.
Then he added two more lines of pins down both sides of my stomach—right where they would hurt the worst.
In the final insult, he attached more pins to my clitoris, pussy lips, and the mound of flesh across my pubic bone.
I couldn’t bring myself to look down to see what he was even doing. I didn’t want to know.
“Spread your legs wider,” he ordered.
I sobbed and moaned in agony when I stepped apart. What in the name of God did I get myself into?
Even thinking that, I couldn’t put my arms down. I was too deep in it even to consider walking away.
He attached the last pin, stepped away, and started circling again. He passed his hand up and down the pins to flick them in place the way he did in the car.
Brushing them like this actually hurt worse than hitting them with the flogger.
He paced all the way around me until he stood behind me again. The flogger would hit me any second now and my nightmare would be complete.
He leaned in close to my ear again. “You’re all mine, aren’t you?” he half-whispered.
“Yes!” I shrieked.
“You love being mine, don’t you? You love it when I make you mine. Say it.”
“YES!!” I roared and broke down in the middle of that word to howl in agony again.
Lightning quick, he grabbed me by the throat in one hand, pulled me all the way back against his body, and his fingers plunged into my ass.
“You’re a perfect little plaything like this, aren’t you?” he growled. “You’ll do anything I say and take any punishment I dish out just to make yourself my toy, won’t you?”
“YES!!” I bellowed and then screamed as his fingers blasted me into a dizzying orgasm.
All the pain exaggerated the energy build-up. There didn’t seem to be a difference anymore between one kind of stimulation and the other. They both amplified the energy off the charts.
It exploded as never before. I flailed in his arms, but he only tightened his grip to hold me in place.
I didn’t even finish orgasming before he let go with both hands. My knees almost buckled in that moment when he no longer held me up.
I probably would have fallen if all those clothespins weren’t there. I didn’t want to move. Moving would only make them hurt more.
I expected him to step away and inflict some other torture on me, but instead, he grabbed me by a combination of my hair and my hands where I held them laced together behind my head.
He tipped me forward and used that hand to hold me in place in a bent over position.
He ripped his pants open and drove into my ragged, exposed pussy from behind.
He had placed the clothespins strategically so they all hung forward and out of the way of the angle he used to enter me.
He plowed in and teased my asshole with his thumb while he fucked me extra hard. The same thing happened. Gravity caught the clothespins, pulled them down toward the floor, and made them hurt more.
That pain melted together with the pleasurable, blissful relief flooding outward from my channel to every inch of my body.
The pain felt unbelievably arousing now. I didn’t notice it while it was happening, but I actually wanted to feel it. It made my pleasure and desire so much more acute.
The clothespins on my clitoris and mound acted like the magnets. The pins stimulated me into orgasming harder and more times than I would have otherwise. The pain enhanced everything he did into an intoxicating cocktail of sensations and carnal delight.
He didn’t ease off in the slightest. He didn’t try to make it last longer to give me more pleasure.
He fucked me fast and hard and came quickly before he stood me up straight again.
He left me standing there in turmoil with all these surges of power racing through me. I kept screaming, crying, moaning, and seething in such a confused tempest of pleasure, pain, and a mindless desire for more—more of everything and anything he could do to me.
He didn’t give me an instant to collect myself before he pulled the flogger out of his pocket and started using it again.
He didn’t do it harder. He didn’t have to. He struck the clothespins again—all of them.
He swatted them lightly—expertly—and flicked one of them off my stomach.
I screeched as the wood pinched on my skin. It hurt a thousand times worse coming off than it did either when he put it on or while it was on.
I didn’t think anything could be worse than having them on. This definitely was. That moment when the wood scraped off and snapped away hurt worse than anything.
The pain didn’t go away now that the pin wasn’t there. The ache kept going on and on. I couldn’t even put my hand down to rub the spot.
He waited an eternity before he went back to hitting all the pins—and then popped off one from right at the edge of my mound.
I didn’t even try to be quiet or to stop myself from screaming out all the agony of what he was doing to me.
All this pain broke my body down into a quivering mass of nerves. It was a miracle I could still stand up at all and he still had God only knew how many pins left to go.
I couldn’t even watch while he flicked off three more, one from my stomach, one from my collar bone, and then he hit me between the legs.
He had to hit a lot harder to knock the pin off my pussy lips. That one stuck, so he had to hit it twice.
I shut my eyes howling in agony while he worked his way methodically up and down my body. He hit the remaining clothespins again and again, just to give me another little dose of pain before he decided he could take the trouble to snap another one off.
My brain got lost in the fog of all these sensations. I did feel a tiny hint of pleasure when he whipped the clip off my clitoris.
Then came the inevitable rush of even more torturous pain after the clip fell off. My pussy ached like anything, but he didn’t rub me to turn me on or make it easier.
He left the clips attached to my nipples until the very end. He whipped off all the clips from my collarbones, stomach, and pussy first.
He worked at random to remove the clips from anywhere else. He didn’t use any systematic approach. He never gave me any sign beforehand which clip he planned to knock off next.
When he removed all the others, he returned to the same place on my left. He slashed the flogger back and forth across my stomach, inner thighs, back, and pussy in between hitting the clothespins still attached to my nipples.
“This is mine,” he snapped between hits. “This is all mine. All of this is mine to play with and tease. Do you hear that? This body is my playground. I do what I want here. You take it and enjoy it.”
I was screaming too loudly to argue. Of course it was his to do what he wanted here. We both already knew that.
He hit my breasts again and three clothespins snapped off. The cascade went much more quickly after that.
He hit the last ones off, but I barely felt it. The tide of aching, smarting pinches all over my body dulled my senses. I couldn’t tell any particular spot from the next. It just felt like my whole body hurt.
He didn’t step in to make it better—not at all. He left me standing there for what felt like a long time.
I shut my eyes and just gave myself over to moaning in agony. When would it be over?
I couldn’t even hope for it to be over. I didn’t want to leave this place of being his. I just wanted to stay here no matter what it cost.
He came up behind me again. “Put your arms down,” he told me.
I almost collapsed then and there. My shoulders throbbed with even more pain if that was possible.
He wrapped a blanket around me in a tight package, but instead of putting me in bed, he picked me up, carried me to the couch, and pulled me sideways onto his lap.
I couldn’t put my arms around him the way I would have liked to, but the blanket seemed to do it for me.
He steered my head onto his shoulder while I moaned and whimpered in the last throes of agony. I knew he would push it farther this time and I was right.
I shut my eyes and tried to pull myself back to normal. The pain didn’t go away. It would haunt me all week. Just when it started to ease, I would come back next week and do it all again.
Was this what my life was turning into? Was I really this messed up—that I got off on this?
I didn’t even really need a safeword anymore. I would never use it. I would never stop him from doing anything he wanted to me.
I would have sat there a lot longer. I might have chosen to stay there on his lap all night long.
In a little while, he shifted me off his lap, settled me on the couch, and left the room.
He came back with my clothes and purse, put them on the coffee table in front of me, and sat down. He rubbed my legs and sides through the blanket.
He didn’t say anything to break the silence. There didn’t seem to be anything to say.
I shut my eyes and turned my face into the cushion. I really didn’t want to leave. I would rather have spent the night here in his bed, but maybe he had other things he needed to do.
He read my mind and left the room again. I must have fallen asleep because I woke up a few hours later in the dark. Streetlights and traffic lights shone through the window.
I looked around. Ash wasn’t here. I was alone except for my clothes and purse sitting on the coffee table.
He came back right then and switched on the lamp next to his bed. It shone far enough away from this couch to cast the room in a low, soft glow.
He sat down in front of me and put a plate of steaming enchiladas on the coffee table in front of me. “Here. Eat some dinner,” he told me. “You need it.”
I sat up and groaned. The same carpet of painful pinches covered my body. They felt like millions of small bruises encasing me in a dull ache—just enough to remind me of what he did to me.
He put two glasses of water on the table and picked up a plate for himself.
I hauled myself out of the blanket. Every move felt like swimming through peanut butter.
I picked up my fork in one hand and the plate in the other. “Did you make this?” I croaked. “Thank you.”
“You’re welcome. You can take a shower before you leave if you want to.”
He didn’t mention me spending the night again. Maybe he would never let me spend the night with him again. Maybe that window had already closed.
The enchiladas tasted incredible. He must have been an amazing cook on top of everything else.
Then again, a lot of single men got to be really good at cooking. They had to so they could eat decent food.
He ate his dinner silently next to me. The inevitable moment crawled closer with every passing minute. I would leave here and go back to my life away from all of this. Was this really what I asked for?
I asked for something real with him, but this whole experiment just turned into a more elaborate version of what it was before. We didn’t seem to be building anything real—not anything I could recognize.
I didn’t know him any better now than I did then. I didn’t share any more of his life than I shared then—except for his bedroom.
Thinking that repulsed me. I didn’t want to stay here as his sexual plaything. This wasn’t what I asked for.
I finished eating, said, “Thank you,” again, and started getting dressed. He didn’t once suggest during the whole process that I could stay over if I wanted to.
I didn’t want to because staying over wouldn’t bring us closer, either. I had already stayed over more than once. Staying over didn’t change anything.
I got dressed and sat down to put on my shoes and socks. He stood up to stack our plates together.
He was on the way out of the room to take our dishes downstairs when my phone rang. I pulled it out of my purse and checked the screen. The call was from Riley.
“Isn’t it a little late for you to be calling me at this time of night?” I asked. “Shouldn’t you be asleep in bed right now?”
“You are not going to believe what I just found out!” she blurted out. “I was going over the files from the Maynard Sutherland case…..”
“You were going over them at home at ten o’clock at night?” I snorted. “You really need a life.”
“Will you shut up and listen for a second? I found something! I found the break we’ve been looking for. Maynard went through a bankruptcy seven years ago. He lost everything and had to rebuild from scratch.”
“Yeah. I know that. We’ve already gone over all the documentation from the files.”
“Not everything. The names of all his creditors were listed in the bankruptcy, but they were all company names. No individuals were named because all the companies were limited liability corporations.”
“That’s why the files don’t tell us anything.”
“Yes, they do. His creditors lost everything and he got off scot-free. He walked away and started again. He rebuilt his empire and all his wealth in seven years.”
“He didn’t walk away scot-free,” I pointed out. “He ruined his reputation. Some of those companies were powerful and influential in his field. They could have made it so he wouldn’t have been able to rebuild at all.”
“That’s exactly what I’m telling you! One of the people on the board of the biggest company—the CEO, in fact—the one person Maynard screwed over the worst—he’s a member of the BDSM club! You were right, Lucy! Maynard did join the club to get close to someone. He joined the club so he could reconnect with the guy and win back his favor.”
I gulped. I didn’t want to ask, but I had to. “Who is it?”
“His name is Ash Keiff. He’s a wealthy local business mogul and he’s listed as one of the officers in the club. I also found records of the two of them doing business or at least meeting for deducible business lunches in the days following Maynard’s initial membership to the club. It looks on the surface like the guy decided to give Maynard a second chance, but I think it’s more likely that Ash Keiff decided to reel Maynard in and get revenge on him for screwing him over. Either way, we finally got ourselves a suspect.”
Ash walked into the room right at that moment and saw me on the phone. He had no idea what Riley just told me about him.
I stared at him with a thousand thoughts rushing through my head. All this time…..he was a suspect in Maynard Sutherland’s murder.
I had been doing all of this with Ash ever since Riley and I started investigating this case. I fucked him and I let him fuck me. I let him do all this perverted stuff to me. I let him get inside my head.
I had a flashback to that night at the very beginning of our relationship. We sat on the couch and he asked me about the case.
Was he trying to find out what I knew? Did he take me as his submissive so he could influence me or at least keep an eye on the case?
None of that mattered because he was a suspect.
I mumbled into the phone, “I’ll call you back,” and hung up.
He stopped in the middle of the room and frowned at me. “Is something wrong?”
I could barely make myself heard. “You…..you did business with Maynard Sutherland….You were involved in his bankruptcy…..”
His eyebrows darted together in the middle. “Yeah? So? Everyone knows about that.” He frowned a little deeper. “Don’t you already know about that? It’s a matter of public record.”
“You……he owed you money……He joined the club to get close to you…..to get back in your pocket……”
He made a face and threw himself down to sit on the bed. A wooden box rested on top of the bedspread. A plastic ice cream container sat nestled inside the box containing all the wooden clothespins.
He started arranging the stuff in the box while he talked and then slid the box under the bed.
“I assumed you already knew about all of that,” he muttered under his breath. “I assumed you would have asked me about it long ago. That’s why I never brought it up. I didn’t think it was an issue.”
“But….you’re a suspect……You could have killed him….”
His head shot up and he narrowed his eyes at me. “Do you honestly think I would kill a man in cold blood—actually tie a plastic bag around his head and watch him suffocate—for a bunch of money I can never get back?” He shook his head and went back to what he was doing. “If you really think I’m capable of that, then we don’t belong in the same room with each other.”
I stared at him—and it clicked. This whole thing had been wrong from the start.
I thought I knew what he was capable of. I never would have believed until right now that he would be capable of something like that.
That was the very thing that made this all wrong. I didn’t know him. I didn’t know him nearly well enough to be messing around with him like this.
I certainly didn’t know him well enough to be going as far as this. I let him get into my head. I let him in willingly.
That was my mistake, not his. He tried to warn me and he was right. I didn’t know enough to make that decision.
I did know enough to make it now. Dead calm came over me when I put my phone in my purse. I hung it over my shoulder. “Riley and I will contact you in the next couple of days to ask you some questions about this.”
I walked past him on the way to the door. I would never set foot this apartment again. I knew that with absolutely no doubt.
His voice snapped behind me. “Lucy—stop!”
I froze on the threshold. Would he always hold that power over me even after I decided I didn’t want him to?
I turned around slowly to find him leveling me from his place on the bed.
“If you walk out that door right now, you take nothing with you,” he went on. “You leave behind what’s mine.”
I didn’t know what he meant. I didn’t have anything of his. I was walking out with my clothes and my purse the same way I walked in.
His eyes gave me no room to answer or to argue. He held me in an unbreakable grip. He would always be able to look at me like that.
He eased off the bed, got to his feet, and stopped right in front of me. “Get down on your knees.”
I sank onto my knees. I didn’t even know why except that he still held this power over me. Walking out of his apartment would never be enough to break that bond.
He flipped up the flap of my purse and took out the large plug he gave me last week. I had forgotten it was there.
He left the lube—as if I would ever use it again.
Then he squatted down in front of me, pulled up my shirt, and unclipped the body chain I always wore around my waist.
That hurt. I didn’t know losing the chain would hurt this much. I was the one who broke the bond. He never did anything to me that I didn’t want.
He stared straight into my eyes the whole time he was down there at my level. I was the one who had to look away.
I winced back tears feeling the chain slide against my skin—until it wasn’t there anymore. It was gone. He was gone. It was all gone.
He stood up straight, coiled the chain into one hand, and used the other to cup my chin and lift my face so he could look straight down into my eyes.
His face blurred in tears, but I already knew what I had to do. This rushing feeling of kneeling in front of him—the flooding sensation of so many overpowering emotions engulfing my whole life—it still took me over. I couldn’t leave.
He stroked his thumb down my cheek only once before he walked away and sat down on the bed in the same place.
He made a fist around the chain, propped his fist against his thigh, and looked at me across the room.
That moment ended it. It was over. The spell broke. He no longer controlled me or influenced me or held any power over me at all.
I stood up and all those feelings died away in a breath of wind. He was nothing but a man sitting there on the bed.
I turned around and walked out of the apartment, never to return.
End of Book 1.
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Thank you for reading, everyone. This book is 80k words, so we will break it there and start up with Book 2 tomorrow morning. Stay tuned to find out what happens next!
