A Masochist's Adventures in Wonderland
Chapter 23
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My phone buzzed on my bedside table. I picked it up and checked the screen. The notification was a text from Ash. Are you in bed yet, baby?
I sat all the way up so I could answer him. Yes, Sir. I’m just going to bed now.
I’m going to video call you. I want to watch you masturbate with your butt plug.
My heart turned a somersault. He had never done this before.
He only gave me the plugs yesterday. I hadn’t gotten a chance to try them yet.
I put the phone down and opened the drawer in the bedside table to take out the box of plugs he gave me.
The phone rang before I had a chance to take out the first plug. I had to stop what I was doing so I could pick up the phone.
It wasn’t the normal phone ringing. It was the video chat app. I turned it on and Ash’s face appeared in front of me. He was in his apartment. This was different.
“How do you want to do this, baby?” he asked.
“I…..I’m not sure. I was thinking…..” I trailed off.
“You should probably take your pajamas off first.”
I mumbled, “Yes, Sir,” and got out of bed to take off my pajamas.
I had to put the phone down. I wound up putting it face up on the bed where he couldn’t see me.
I realized too late that I probably should have propped it against the lamp so he could watch me get undressed, but it was too late.
I picked up the phone and looked around the room. “How should I do this?” I asked.
“That’s what I’m asking you. How would you be most comfortable? Do you want to lie on the bed? How were you planning to do this?”
“I don’t think lying on the bed is the best way to do it—especially if you want to watch. I would have to hold the phone with one hand. I would only have one other hand free to…….” I trailed off again. I didn’t want to say it.
I didn’t even know how I would begin to masturbate when I had a butt plug in.
I did know, though. He demonstrated it yesterday. I had to use my vibrator while I used the plug on myself.
I saw and felt enough yesterday to know I would need both hands free.
“If you’re leaving it for me decide, then I think I should kneel down on the floor,” I told him. “I think that will be the best way.”
“Do whatever you feel most comfortable doing. I’m only here to watch. You do whatever you want to do.”
I resisted the urge to tell him I didn’t want to do this at all. Using the butt plugs on myself wasn’t even my idea. I wouldn’t be doing it at all if he didn’t tell me to.
Having him watch me do it would only make it harder, but this was the situation I got myself into when I agreed to obey him as his submissive.
I took out the box of plugs and my vibrator, knelt down on the floor to open the box, and took out the smallest plug.
It sure did look small compared to how tight it felt yesterday when Ash used it on me. I wouldn’t have thought something so small could make me feel so stretched.
That feeling lasted for the whole thirty hours since I left Ash’s apartment. I kept feeling something inside my ass for the rest of yesterday.
It was still there when I woke up this morning. It was there all day today while I was at work.
It didn’t feel right, but the wrongness was starting to wear off. The mind-blowing hotness of doing something so forbidden was beginning to erase ahu inhibitions I had about it.
It aroused me in such a different way than normal sex, but anal play aroused me just the same. It wasn’t worse. It was just different.
I unscrewed the cap from the lube, pulled out the smallest plug, and squirted lube around the tip. I had no idea how much to use, so I only used a little bit.
This time, I propped the phone right in front of me so I could see Ash without holding onto the phone with my hands. He stared back at me from his apartment.
“Go ahead and get started whenever you want,” he told me. “Do whatever feels the most natural and the most comfortable.”
Masturbating like this didn’t feel natural or comfortable because I never masturbated like this. I always masturbated in my bed with my pajamas on and the covers pulled all the way up to my neck.
I should be turning this into a performance for Ash’s visual enjoyment.
Another part of me realized it wasn’t about that at all. He didn’t want entertainment or even stimulation. He stayed too quiet even to tell me what to do. He just wanted to watch.
I made sure to position the phone securely enough against the wall that it wouldn’t fall over, took the plug in my right hand, and the vibrator in my left.
I rocked forward, but it turned out to be too awkward to hold both and use both at the same time. It made more sense to hold myself up on all fours.
I wouldn’t be able to do that without putting one of them down. I still needed to hold onto the plug, so I put the vibrator on the floor.
I moved my right hand behind me, touched the tip of the plug to my ass, and spread my knees so I could ride the vibrator right there on the floor.
The vibrations hit me from the front and the cold lube touched my sensitive asshole from behind. The two sensations combined with the view of Ash’s face in the phone camera window.
I locked my eyes on him. Just looking into his eyes like this turned me on instantly and I groaned in an agony of desire.
“Do you feel me fucking you in the ass, baby?” he murmured.
My lips pouted open and I gasped as I slid the plug in. Holy fuck, it felt good.
I rocked on the vibrator feeling myself wind up to an explosion. I worked the plug in and out pushing it in deeper.
The stretching, intrusive sensation plunged me back into that unholy place of pure, raw, unchained madness. I couldn’t speak, but I also couldn’t tear my eyes away from Ash’s face even when I couldn’t completely bring him into focus.
“That’s right,” he murmured under his breath. “Fuck that ass. That’s right. You know you want my cock in your ass right now. You want me to bend you over and pound you ass until you scream. You feel that right now, don’t you?”
I moaned louder. I couldn’t stop panting in desperation. I did want that. The thought of him actually fucking my ass with his fully erect cock sounded like the hottest thing I could possibly imagine.
For some reason, I could imagine him doing that and watching me from the front at the same time. He really was fucking me in the ass right now.
I worked the plug in deeper—until I realized it couldn’t go in any deeper. The flared base touched my asshole. That was as deep as it went.
The realization distracted me and I looked around. “What’s wrong, baby?” Ask asked.
“I just…..” I pulled the plug out and looked it trying to put the pieces together.
For a start, the plug itself was totally clean apart from the lube. It wasn’t smeared with shit the way I thought it would be, but that wasn’t what stopped me from using it.
The plug itself really looked small. It was nowhere near as big as his cock. How would I ever take his cock if this was all I could handle?
I never would have believed it was this small. Now it didn’t look anywhere near big enough. It didn’t feel big enough, either. I needed something bigger.
Ash’s voice cut in on my thoughts. “Baby? Talk to me, Lucy. What’s wrong?”
“I just…..feel like……like I need something bigger.”
“Go ahead,” he told me. “Use the next size up.”
I mumbled, “Yes, Sir,” and switched off the vibrator so I could think straight for this operation.
I pulled a tissue from the box on the bedside table, put the smallest plug on the tissue, and set it aside where I wouldn’t see it. I would deal with all of that later.
Then I put lube on the next larger plug. That one didn’t look big enough, either, but I knew better than to try anything bigger—not on my very first time. I didn’t want to hurt myself.
The tube of lube was only about three inches long and no bigger than my pinkie finger. The second squirt of lube almost emptied the tube. I would have to do something about that.
I would need more lube for all the times I masturbated this week when I used the butt plugs on myself. I would have to get some more lube from the drug store or something.
This was turning into a major project, but that would have to wait, too.
I switched on the vibrator and straddled it in the same position. I extended my right hand behind me—and looked straight at Ash when I started working the plug into my ass.
It started as easily as the smallest plug. The width didn’t challenge me at all. It just felt amazing and deeply, deeply intoxicating.
“That’s right, baby,” he murmured. “Take it nice and deep in your ass. You want that, don’t you? You want me to fucking destroy that ass. You feel that, don’t you? You feel me fucking you and making you cum for me.”
I whined in ecstasy as the plug got thicker toward its widest end. The dark, violating feeling overpowered me and skyrocketed me out of my mind. I wanted him. I wanted him to nail my ass as deep and hard as he could.
The vibrator escalated those sensations so much faster.
“Take it all the way in, baby,” he told me. “Take that cock and let me fuck you.”
I pushed the plug in as deep as I could stand and worked it in and out to fuck myself. I couldn’t focus my vision anymore. My eyes rolled back in their sockets and I heard my moans rising to cries of desperation.
He didn’t say anything else. I got lost in all the dizzy waves of pleasure rushing through me. The vibrator excited my clitoris, but this position also sent those vibrations through my pussy and even to my ass.
The vibrations made the plug so much more stimulating and arousing.
My asshole stretched to its limit to take the widest base of the plug, but even that wasn’t enough.
I escalated and started to cascade into a whirlwind of orgasmic pleasure. I couldn’t stop now, but right in that moment, in the moment when I fucked my ass with the widest part of the plug—even then I wanted more.
I wanted his cock. I needed it. I wouldn’t get it tonight, but I would get it. I had to.
The untamed rawness of having him really nail me in the ass—I couldn’t think of anything hotter than that.
All the fantasies I’d been having about someone holding me down and doing whatever they wanted to me—this was it. This was the natural endgame to all of that. What would he be doing if not that?
I didn’t understand half of what I was thinking in that moment, but I did understand this. I needed to something bigger. This plug wasn’t big enough, either.
I didn’t know how big I could go, but I had to try. I just wouldn’t be trying tonight.
I was already spiraling into insanity feeling the plug tear my asshole open. I pushed it in to its widest depth and worked it over my tight asshole so much harder than Ash ever did.
I could do it to myself. He would never do something to hurt me. He played it safe to protect me.
Now I wanted to feel him using me. I actually wanted to feel him hurting me in that way. It felt so wrong—so against everything I thought I wanted.
I could do that and still be perfectly safe because he wasn’t the one hurting me. I was doing it and feeling him do it.
That sensation hurt, but it also blasted me into an earth-shattering orgasm of ultimate carnal bliss. He was using my ass in the most brutal possible way. He was holding me down against my best efforts to struggle free while he took what he wanted.
I couldn’t see him anymore. My head drooped as I screamed out every broken desire pouring out of my heart.
I didn’t have to explain any of this to him because he obviously already knew exactly what I wanted.
I could have kept going. I pushed the plug all the way in. My asshole eased around the base and the plug settled into its place right up against my ass.
This created a brand new sensation with the vibrator. It turned me on in a different way—an easier, less confronting, more comfortable way.
I felt myself starting to get turned on again, but I didn’t want to go there tonight. If I kept going now, I might never stop, so I pulled the plug out, sat up, and turned off the vibrator.
I set the plug on the tissue next to the other one, rested forward on my hands, and shut my eyes. I needed to get myself together, but I also felt myself starting to crash. I really just wanted to be asleep in bed right now.
“That was beautiful, baby,” Ash murmured. “Thank you for sharing that with me tonight. I love the way you take it in the ass.”
I couldn’t think well enough to answer or even to open my eyes. I gulped. Even that small sensation threatened to shatter me into another orgasm. I really needed to go dormant right now.
He read my mind as usual. “Get in bed, baby. Take your phone with you.”
I barely opened my eyes enough to pick up my phone and crawl into bed. I didn’t look closely enough to make sure the phone was even pointed in the right direction so Ash could see me.
I tilted the phone toward me. Maybe he could see me and maybe he couldn’t.
“Good night, baby,” he breathed. “I miss having you in my bed. I’ll be holding you in my arms tonight. Now turn off the lamp, hang up the phone, and go to sleep. I’m with you. I’m with you right now…….”
I couldn’t think well enough even to say, Yes, Sir.
I hung up the phone without even saying goodbye to him, turned off the light, and collapsed. I didn’t even remember to put the phone on the bedside table before I completely passed out.
End of Chapter 23.
