A Masochist's Adventures in Wonderland
Chapter 24
_______________
I was just coming up the stairs to my apartment when I spotted a delivery package sitting propped against the door in the hall.
I stopped in my tracks when I saw it. I didn’t order anything—which could mean only one thing. I was supposed to meet Ash tonight, so he must have sent it.
My surprise turned to excitement when I picked up the package and took it inside. Plain brown paper covered the outside. The package didn’t look like anything special.
I put it on the kitchen counter, tore off the paper, and found another handwritten note in the box inside.
Wear this under your clothes tonight. You can wear anything you choose over it.
I looked into the box and found the lingerie he had me wear last time, but the leather harness wasn’t here.
I took a shower and put on the lingerie in front of the mirror. It looked stunning, especially with the body chain I already wore.
I chose a simple, wrap-around maxi dress to go over everything. That would make it easier to take off when the time came—which would be sooner than later if I knew anything about Ash.
I drove across town to his apartment, went upstairs, and slowed down when I walked in and found him sitting on the couch as usual. Why did I think it would be any different?
My excitement died when I stopped in my usual spot. He studied me like a specimen under a microscope—as usual.
His direct stare killed my excitement. I was here for him to evaluate, not to enjoy myself.
I couldn’t hold his gaze, so I pulled the box of butt plugs out of my purse, put the box on the coffee table in front of me, and put my purse on the chair.
I straightened up, but I kept my eyes down. I already knew where this was going and what he would ask before he asked it.
“Take your dress off,” he ordered.
I untied the ties. I didn’t have to do anything else to take my dress off and put that on the chair, too.
I felt him checking me out in my lingerie when I stood up straight in front of him.
I got the same stomach load of tension when all the same old questions rushed back into my mind. Would he be satisfied with what I had been doing this week? Would he find any fault in it—or in how I dressed for him tonight?
Was I doing any of this right? Was I being good enough as a submissive for him to keep me on?
“So?” he finally asked. “Which plug have you been using?”
I couldn’t look at him. “The biggest…..Sir.”
His eyebrows shot up. “The biggest! Why did you escalate so quickly? I hope you didn’t hurt yourself.”
“No, Sir. I didn’t hurt myself.”
“Then why did you escalate so quickly?”
I shrugged at nothing. “You said……you kept saying…..you wanted me to work up to full penetration…..you know…….so you could fuck me. You said that’s what you wanted…..”
“Is that what you want?” he asked.
I nodded down at the floor. It took me a week of experimentation before I could finally admit that to myself.
Using a butt plug on myself sounded so ridiculously out there. I never would have been able to take it seriously—not seriously enough to keep doing it for a whole week.
Getting fucked in the ass for real—getting fucked in the ass by Ash—actually having him take me like that—that was the motivator. It was more than a motivator. It was rapidly becoming an obsession.
I fantasized about it every time I used the plugs. It was the only thing I thought about.
I never put in the plug and left it there. That would have been too weird.
I always thought about him doing it to me—with his body—actually holding me and fucking me like that for real. It was the only thing about anal play that I wanted—and I wanted it bad—real bad.
“All right,” Ash replied. “Then that’s the one we’ll use. Show me what you’ve been doing.”
I picked up the box, took out the largest plug, and put the box back. I couldn’t hold his gaze when I opened my purse and took out the bottle of lube I got from the drug store.
I hadn’t used the lube from the box after that first night. I didn’t want to use it up. The tube was still in there.
I returned to the same spot, squatted down, and popped the lid off the lube bottle.
Ash got to his feet just then. “No, no,” he interrupted. “I changed my mind. Don’t do it there. Come over here.”
I looked up. I didn’t know what he meant, but he showed me by waving me toward the couch.
He even walked over to me and put his hand behind my shoulder to guide me where he wanted me to go.
He steered me to the couch and he stopped me in front of the thick, padded leather arm on the other end—the end opposite where he usually sat.
He took the plug and the lube out of my hands. I had no idea was to do.
I looked around trying to figure it out when he pulled a small black toy out of the pocket of his suit jacket. It was the same toy he made me sit on in the passenger seat of his car.
He handed it to me. “Straddle the arm of the couch with this inside you. Show me how you ride this thing like you want someone to fuck you.”
I looked down at the toy in my hand. My brain took a minute to catch up with exactly what he was telling me to do.
He didn’t give me a chance to figure it out. He stepped behind me where I couldn’t see him. That left me to follow his command by myself.
The first part I understood perfectly well. I stepped forward and spread my legs to straddle the couch.
The garter belt fell against my thighs. I looked so much more sexual in this position.
The procedure for sitting down on this toy took another mental effort. I angled it toward my pussy, pulled my panties aside, and slipped the toy inside before I sank the rest of the way down onto the couch arm.
I didn’t realize what he meant about riding it until my weight actually sank onto it.
The couch arm actually felt like straddling and riding a person—a person with a nice, hard, juicy cock buried inside me.
Holy fuck, it felt good. It overpowered me with the need to fuck.
I propped my other arm against the couch just as if I was holding myself up on a man’s chest while I rode him.
My eyes drifted half-shut in hot, dreamy desire as I picked up speed and rocked on it.
I held the base of the toy down on the couch arm so I could angle my hips back and forth in exactly the right rhythm.
Ash ran his hand up my spine from behind. “That’s good,” he murmured. “Fuck that thing the way you know you want to. You’re so fucking hot when you arch your back like that. Come on. Show me that ass. I’m gonna fuck you so hard, baby.”
His voice lulled me into a trance. I could convince myself as long as I kept my eyes unfocused that I was riding him on his bed.
I never imagined riding the arm of the couch would feel like this. It introduced a whole new dimension to pleasuring myself. This might turn into my new favorite way to get myself off.
He stroked his hand down to my waist, closed my hip in a powerful fucking grip, and then stroked down to my ass.
He pushed me a little farther forward. “Stick that ass out for me to fuck, baby,” he growled. “That’s right. You know what I like.”
His voice mesmerized me into arching my back and sticking my ass out farther. I really wanted him to fuck me like this. I wanted to cum like this.
That was the moment when the cold, slippery lube of the plug touched my asshole. I had gotten used to it now and it turned me on instantly.
I threw back my head and moaned for it. I floated into the fantasy I always had this week about him taking my ass from behind.
He kept murmuring and growling under his breath. Damn, he sounded turned on—as turned on as I was.
He worked the plug in harder and faster than I usually did. He stretched my asshole more than I would have felt comfortable with, but it felt so much more like him fucking my ass when he did it like this.
I no longer controlled the rate or the depth. He was doing it to me—which was what I really wanted.
He worked it in to its widest depth. The plug spiked me straight into the heights of stratospheric madness on the way to an epic orgasm.
I whined and screamed as the plug stretched my asshole to its limit. I was going to cum any second now—and then the sensation changed.
He pulled the plug out and something warm, soft, and much, much bigger touched me. It was him.
The lube surrounded it in slippery wetness, but the hot, living thickness of it sent me reeling out of my mind into something closer to mental chaos.
He was actually doing it. I was actually pushing into me.
He clamped his hand on my shoulder right at the base of my neck. That grip wouldn’t let me go.
His usual sultry murmuring undertone changed to a low snarl of brutal, feral, predatory lust. “Come on,” he rumbled. “Give me that. This is mine. You give me that ass. You’re mine to fuck any way I want to. Come on. Back up that ass and take it like a good girl.”
I couldn’t move, not even to rock on the toy inside me. His cock exploded my world apart—and my body apart.
He wasn’t that much thicker than the biggest plug. That extra little bit of girth felt so much bigger—now that I knew he was really driving his living cock into my asshole.
I gasp and then really did scream as the intensity shattered my defenses. He didn’t let go of my neck—not at all.
That crushing hold told me loud and clear that he was going all the way in.
He grabbed my hip with his other hand and pulled me back into him. That one small movement electrified all the nerve endings up my channel and excited me on the toy in my pussy.
I rode down on it and blasted into a powerful orgasm. My scream turned to a broken cry of ecstasy and he drilled the rest of the way in.
I couldn’t stop rocking on the couch arm—and dropped back into the fantasy of him fucking me in the ass—except that it wasn’t a fantasy. He was really doing it.
He stroked in and back out picking up speed and power. His cock was much longer than the butt plug. He broke open more of my defenses on the way in, but that only made me cum harder for longer.
The longer he did it, the more the sensations kept firing back and forth between my pussy and ass. They worked together with each other.
His cock rubbed against the toy with only a thin layer of my flesh between them. They excited each other. Each one made the sensation of the other more acute and intoxicating.
I wavered in a haze of so many explosions going off inside me. I barely became aware of him pulling out of me.
His jiz oozed out of my asshole when he did. He must have cum in my ass.
His warm hands kept stroking up and down my back, rubbing my shoulders, and guiding my hips back and forth on the couch arm. I didn’t seem to be able to stop fucking this toy.
He leaned forward, wrapped one arm around my waist, and his other hand took hold of my wrist—the one holding the toy in place.
His mouth pressed against my ear in a hot, low seductive whisper. “Nice and easy,” he breathed. “Power down now. Slow down….and ease off…..that’s it…..slowly……”
He didn’t wait for me to do it. I wouldn’t have been able to. I couldn’t think with all these waves of pleasure coursing through me.
He used his arm to lift me off the couch, held onto my wrist to force me to pull the toy out, and physically carried me off the couch arm so I couldn’t ride it anymore.
I kept howling in moans that wouldn’t stop. My body buzzed from all these orgasms. My asshole never felt more stretched and ravaged.
He kept his arm around my waist, sat down in the middle of the couch, and tipped over to pull me onto it while he held me from behind.
I curled onto my side and he guided me into him so we both lay down side by side.
I shut my eyes, but I didn’t drift off. Doing it like this energized me more than I ever imagined. I could have kept going.
Where would it end? Would I ever be able to stop once I started?
He had to stop me. I couldn’t do it on my own. Was this what I was turning into—this sex maniac who would do such perverse things and couldn’t get enough of it?
End of Chapter 24.
