A Masochist's Adventures in Wonderland
Chapter 21
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I woke up from a sound sleep—and froze when I saw Ash lying on his side right in front of me. He was wide awake this time.
His eyes traced every shade of my expression. He must have been lying there awake the whole time and watching me sleep.
He didn’t lie with his arms around me now. He left a few inches between us.
The blanket still encased my whole body—and so did the gag in my mouth and the rope around my legs.
He immediately pushed himself up on his elbow. “Good morning,” he told me. “You slept well. That’s good.”
He bent over and started unbuckling the gag. When he finished pulling it out and laying it aside, he peeled off the blanket away and finished untying and unwinding the rope. He threw it over the side of the bed onto the floor and pulled my thighs apart.
“Spread your legs so I can take these out of you,” he told me.
I rolled over on my back while he stuck two fingers inside me. He did it so clinically. This whole operation reminded me of going to a visit with the gynecologist.
He scooped out the two glass balls he put inside me last night. My juices covered them, but he didn’t seem to notice.
He used his other hand to tip me back onto my side, tucked the blanket around me, and went off to the bathroom. I heard him rinsing the balls under the tap followed by a silence. He must be drying them.
He came back into the room, put the two balls on the dresser across the room, and lowered himself onto the mattress in front of me.
The blanket surrounded me in a bubble of comfort. I could finally relax. That was the moment when I realized I wouldn’t have been able to relax like this last night. I was too worked up when he brought me up here.
I wouldn’t have been able to cope with him taking the gag or the rope off or taking those things out of me. He actually did me a huge favor by leaving everything in place until I got some much-needed rest.
He raised his hand and raked his fingers through my hair to push it back out of my face. He trailed his fingers behind my ear to arrange my hair back there.
“How do you feel now?” he asked.
I thought about it. What could I say? I wasn’t sure how I felt except that I felt rested and much more relaxed than I did last night.
“What did you use on me that first night when we did it?” I blurted out.
He frowned. “I don’t understand what you mean.”
“You put some kind of clamp on my clitoris—but it didn’t feel like a clamp. What was it?”
“Oh, that. It was magnets. They fit on either side and squeeze together to act as a clamp.”
I looked away and wound up rolling onto my back to look up at the ceiling.
“Are you okay?” he asked. “Are you okay with everything that happened last night?”
I barely glanced at him. “I’m fine with it. Why? Did I not seem okay with it?”
“I just want to make sure. Was there anything you wanted to talk to me about?”
I didn’t have anything I wanted to talk about. I didn’t have a problem with anything he did to me last night, but it did make me think. All of it made me think a lot more than I realized at the time.
I rolled onto my side to face him, but I didn’t say anything. I studied him trying to figure him out.
My attention unnerved him. His eyebrows jumped together in the middle. “Is something wrong?” he asked. “Did you like being tied up?”
“I always like being tied up.”
“I mean did you like being tied up like that—in an uncomfortable position?”
“Yes, I liked it. I didn’t snap my fingers, did I?”
“What about the ben wa balls? Did you like them?”
“Yes, I liked them.”
He hesitated. “What about the anal play? No one has done anal on you before, have they?”
Now I had to look away. I rolled onto my back again so I wouldn’t have to look at him. “No, no one has ever done it on me before.”
“Did you like it?” he asked.
I didn’t answer. I couldn’t decide if I liked it or not. I didn’t like it and I didn’t not like it.
I had no opinion about it at all for some reason. It just sort of happened. I had never experienced anything like it before in my life.
I had also never experienced anything I felt this vague about. I didn’t even seem to be able to think about whether I liked it or not.
“Talk to me,” he went on. “I need to know if you liked it or didn’t like it.”
“I don’t know,” I murmured. “I don’t know if I liked it or didn’t like it.”
“Would you like to try it again?”
‘I’m not sure.”
“Would you be willing to try it again?” he asked. “Is it something you definitely don’t want to do again?”
“No, I don’t feel that way about it.”
“Then would you be willing to try it again?” He changed his tone and a tiny hint of iron crept into it—just enough to let me know I didn’t have a choice but to do what he said. “Turn over and look at me when I talk to you.”
I rolled onto my side facing him and looked up into his eyes. They brimmed with a combination of emotions and expressions. Was he angry? Was he confused? I couldn’t tell that, either.
“Now answer my question. Are you willing to try it again?”
“Yes, I’m willing to try it again.”
“Tell me what you were feeling when I did it.”
“I’m not sure what I was feeling.”
He compressed his lips in a very distinct expression of annoyance. “We aren’t going to get anywhere if you keep stalling me like this, Lucy. I asked you a question and I expect you to answer me. I can’t be your dominant if you don’t tell me what you were feeling when I did something new to you. What were you feeling when I did it? Tell the truth and don’t tell me you don’t know or that you aren’t sure or any other evasive answer.”
That one moment when he pursed his lips put the fear of God into me. It startled me much more than what he said or how he said it.
Making him annoyed at me was the last thing I wanted. I really, really didn’t want to find out what happened if I annoyed him.
“I felt….I don’t know….I felt like….like it was so out of this world that it wasn’t even in the same dimension as any of my senses or whatever apparatus I use to feel things—like my sensations and mind it weren’t wired to process that. It felt like…..like it wasn’t real.”
“Anything else? Did you find it arousing in any way—apart from everything else that was happening, I mean?”
I couldn’t hold eye contact with him at all when I said, “Yes, I found it arousing…..but not in the way I find everything else arousing.”
“What do you mean?”
“I mean….it was….just….wrong…..and dirty….and uncomfortable…..and….and wrong……I guess…..that’s what I found arousing about it……that it was wrong.”
“I want you to shut your eyes right now,” he told me.
My eyes obeyed that command instantly. I shut my eyes and curled deeper into the blanket.
His voice drifted into my brain. “I want you to concentrate on your asshole right now—on the sensation of me stretching it. Do you feel that?”
“Yes, Sir,” I mumbled.
“You feel me sticking my thumb in your ass while I fuck you. Do you feel that?”
My mind rushed back to last night. I had to steady my voice before I said, “Yes, Sir.”
“Now roll over onto your stomach and lie down flat on your face.”
I did it without opening my eyes. I didn’t know what he planned to do.
He pulled the blanket away and left me lying there naked on the bed. He got up and moved around the room somewhere away from me.
I opened my eyes enough to see him rummaging around at the foot of the bed. I didn’t know what he planned to do, but I kept my eyes open after that.
He stretched out on the bed next to me again and stayed propped up on his elbow.
“Take this,” he told me and pressed something into my hand.
I glanced down at the object. It was the small cylindrical vibrator he used on me previously.
“Stick it between your legs. When I tell you to turn it on, you’ll turn it on. When I tell you to turn it off, you turn it off? Do you understand? Press the button to turn it off and on. Press and hold the button to make the vibrations increase. Understand?”
“Yes, Sir. I understand.”
“Go ahead and put it between your legs, but don’t turn it on until I tell you to.”
I shoved my arm underneath my body and positioned the vibrator right on top of my clitoris. I fingered the cylinder until I found a small, barely detectable raised button sticking out of the silicone surface.
I heard him doing something back there. His voice floated into my brain again from what felt like a long way off.
“I’m going to play with your ass again right now,” he told me. “You’re going to turn on the vibrator and I want you to imagine me fucking you in the ass with my cock. Do you understand that?”
I gulped. “Yes. Sir. I understand?”
“Does that turn you on? Does it turn you on when you think about me fucking your ass?”
I opened my mouth to say I didn’t know, but I stopped myself from saying that. He obviously didn’t want to hear that, so I just said, “Yes, Sir.”
I didn’t know if I wanted him to fuck me in the ass with his cock. That sounded like the most brutal, painful, unhygienic thing ever—but I did find it arousing. I couldn’t even explain why.
The very thought of someone touching a person’s asshole sounded like the worst idea in the history of bad ideas. I never would have gone along with this if he asked me beforehand if I wanted him to—or even if I was willing to.
Now I found myself going along with it—not because I necessarily found the idea arousing but out of pure insatiable curiosity to find out what it would be like.
Obviously I knew about tons of people who loved it—gay men, for example. Plenty of straight people loved it, too. I even vaguely remembered Riley mentioning it.
I must have deliberately purged the conversation from my long-term memory. I didn’t remember what she said about anal sex. I wasn’t sure I wanted to remember.
I couldn’t envision her receiving it. Maybe she did something like that to her submissives.
I didn’t want to know about that, either. I really didn’t want to know anything about Riley’s sex life.
If that many people liked it, maybe I would like it, too. How would I know if I never tried it for myself?
The reality was that I had tried it for myself—only once—last night. Maybe if I tried it again, I would start to like it.
Ash made a good point when he asked if I definitely didn’t want to do it again. I couldn’t say I definitely didn’t want to do it again. Why not try it again?
If I really didn’t like it, I could refuse to do it. He wouldn’t force it on me. I understand him well enough by now to know that.
He controlled himself too well and he proved to me a thousand times that he really did have my best interest at heart.
He never did anything to me that I didn’t want and he swore to me that he never would.
He brought me back to reality real quick. “Turn on the vibrator.”
I pressed the button and the cylinder started vibrating between my legs.
It started as a low buzz—barely enough to warm up my skin. The gentle vibrations spread through me and helped me relax, but they didn’t really turn me on—not much.
I pressed and held the button. The vibrations escalated.
I stopped when they did start to turn me on. I started to float into the clouds of rapture.
I stiffened when he grabbed my ass cheek and pulled it sideways. The air hit my asshole. Here it came.
Something cold and wet touched my sensitive skin. Him playing with me with his thumb last night left the skin ultra delicate and already stretched wider than it should have been.
“Increase the vibrations,” he ordered.
I pressed and held the button again. The vibrator picked up speed and I started cycling higher toward having another orgasm.
He pressed whatever it was tighter into my asshole. The cold slipperiness lubricated it—and something penetrated. It was smaller than his thumb.
“Feel me fucking your asshole,” he rumbled in my ear. “Feel me making you cum from reaming your ass with my cock.”
I gasped and my eyes flew wide open. I could only stare as whatever it was intruded deeper. It stretched me wider.
The sensation of horrible, awful wrongness—the darkness from last night came rushing back—but the vibrator made it all so mind-blowingly hot in a filthy, alien, violating way.
This represented everything I thought I stood against—everything I wanted to fight and work to eradicate from the world.
I became a cop to stop things like this—and yet it turned out to be one of the most blisteringly erotic sensations I had ever experienced.
I pressed and held the button again. The vibrations built to a deep, penetrating buzz. That vibration spread through my body. I couldn’t hold back the tide. I was going to cum any second now.
He worked whatever it was into and out of my asshole faster in an unmistakable fucking motion. He was fucking my ass. Was he using his finger? Something told me it wasn’t that. It felt too smooth.
In that moment, I got a mental flash of him kneeling behind me and holding my hips while I knelt in front of him on all fours.
He pulled me into his thrusts while I slammed his thick cock deep into my ass. Holy fuck, that turned me on! Just thinking it blasted me into madness.
I wanted him to. I really, really wanted him to. I couldn’t even understand why because, even as I thought that, I knew it was wrong.
The wrongness, the forbidden cruelty of it—it made it irresistible.
He wasn’t using his cock on me. He couldn’t be. He lay next to me on the bed fully clothed. He still wore the same suit from last night.
Whatever object he used on me stretched me more and more as he pushed it in. It became uncomfortable, but not painful.
The uncomfortable sensation actually made it so much more arousing. It electrified me. I started to scream.
I screamed louder and harder than ever before. He drove it in harder and deeper as my screams escalating. The sensation that he was violating my asshole became so acute that I didn’t know how to cope with it—but that sensation made me orgasm harder.
He pushed it all the way in—and then the stretching feeling stopped.
Whatever he used on me lay buried deep inside my asshole. It didn’t move.
I couldn’t stop wailing and crying out from all those sensations crashing in on me at the same time.
“Turn off the vibrator,” he told me.
I pressed the button and wilted on the bed still reeling and moaning from all these sensations. I couldn’t decide if they were pleasant sensations. I couldn’t even identify most of these sensations.
He left me lying there for a minute. The feeling of that thing embedded in my ass somehow turned off my rational mind. I couldn’t think even to decide what to do with all of this emotion and sensation.
His voice cut so much deeper now. He sounded dangerous. “Roll over onto your back.”
I had to summon all my willpower just to move. I wouldn’t have been able to move if his voice hadn’t acted on whatever part of my mind he controlled now.
I had to move slowly. I kept waiting for the thing to hurt me even though it didn’t.
I turned over and groaned when I stretched out on my back. My weight pushed the thing deeper into my ass, but I still didn’t feel enough to stop this—not yet.
As soon as I got into that position, I noticed Ash standing at the foot of the bed beyond my feet. He was in the act of taking off all his clothes.
His eyes went deadly hard. “Prop yourself up on your elbows and spread your legs for me,” he ordered.
I had to go through another agonizing process just to summon the brain power to push myself up on my elbows. Everything felt different with that thing in my ass. Everything about my thinking worked differently as long as it lay there inside me.
I pushed myself up and let my thighs fall open. He looked straight up at me with my crotch laid bare right in front of him.
The minute I got into that position, my eyes locked on him. The rush of pure carnal desire nearly made me cum again right then and there.
Holy fuck, he looked hot! He did something to me just from looking at me in that position.
He must be able to see that thing inside me. I still didn’t know what this thing was, but I did know about butt plugs. This must be one.
He crawled onto the bed on his hands and knees, took a position over me, and lowered his stiff, hard cock into my waiting slit.
The plug made my pussy extra tight and skyrocketed me into the cosmos.
“Feel me fucking you in the ass,” he ordered. “This is my cock ramming you in the ass right now.”
Those words worked their charm on me. My eyes slipped out of focus as a colossal wave of pleasure and scorching erotic power took hold.
I felt him. His cock compressed my asshole around the plug and made it feel a thousand times bigger than it was.
He started pumping into me. Each thrust made my ass ride down on the plug. My ass rocked on the bed and drove the plug in tighter—but it never moved.
I felt it. I felt his cock breaking my asshole apart. It didn’t hurt. It just felt so unbelievably thick, hard, hot, and brutal.
The darkness consumed my mind. I fell into a vast sea of pure darkness. He was fucking me in the ass just like all those people I considered so messed up.
“Look at me,” he ordered.
I looked up, but the hard, commanding glint in his eye only made me orgasm. I couldn’t focus on holding eye contact.
I floated in and out of focus again and again feeling all the dark, filthy wrongness of his cock violating me. That darkness made me cum so much harder than ever until he shot his load and collapsed on top of me.
End of Chapter 21.
