She was behind me again, and I was readying myself for a continuation of the teasing torture when, instead, she started lubing up my butt. My breathing stopped, as something started putting pressure on my hole, slowly opening it and sliding inside me. This was no finger, it was thicker, much thicker. She kept pushing as I worried my sphincter would tear, when, suddenly, it just slid in, my hole closing around it. I could feel it inside, pressed against my gut. It wasn’t painful, it was… strange.
“I’ll be back in a while. Don’t move.” She jested as I heard the door close.
My arms and legs were starting to fail me when she finally made it back. My mouth was dry and sticky, not having dared to remove the handkerchief, and I had very much grown accustomed to the object in my butt, to the point that, some slight movements actually made it enjoyable. I was still hard and horny as I had never been before.
She stroked my shaft a couple of times as she walked by me, which made me moan, muffled by my filled mouth. She dragged a chair and sat on it, only few feet in front of me. She was still wearing her suit and gloves, but now she was sporting a strap-on dildo as thick as my arm and maybe half its length. She laid back on the chair, her butt sitting on the edge, and pulled out a phone. With a touch, a slight hum materialized in my ass, a vibration, surprising me and making me moan again.
My cock beat due to the unusual feeling, and although it wasn’t quite enough, the alternating vibrations were undoubtedly adding up.
“So, I was thinking to fuck your ass with this,” she said as she stroked the large dildo. “But then, that may actually make you cum to full relieve; Do you think you deserve it?”
Considering I had almost no brain function left, this question made me freeze. I couldn’t speak, obviously, although maybe even without the muzzle I’d still be unable to articulate a thought at that point. So, I had two choices, nod or shake my head. I didn’t want her to fuck my ass with that, so that would be a shake, but that would imply I didn’t deserve to cum, and boy, I think I deserved that more than anything in the world. But if I nodded consent to cum, she’d take it as I wanted to be fucked in my ass. So, baffled, I just stared, my eyes wide open.
She waited patiently, using her phone to alter the speed and vibrations in my ass as she just stared at me. She didn’t ask again, she didn’t rush me. She waited.
Finally I gave her a slight nod.
“Good choice Buddy. Good boy.”
She stood up immediately and to my surprise, she removed my gag, and started undoing my bindings.
“I want to cum, Mistress, I don’t-“ I started to speak while she untied one of my wrists.
She turned around and slapped me hard, making my eyes tear up.
“I’ll teach you to speak only when asked,” she added simply and continued undoing my bindings.
I rejoiced in being able to move. My back felt as if it had been trampled and my arms as if they were going to fall off. Once completely free, she turned me around on the table and started locking me down again. My arms were tied down by my sides, the collar held me against the wood, and two flaps raised up and pressed my head keeping it in place looking up, preventing me from turning it.
I could see now above me, hanging from the ceiling, the array of poleis and hooks that she was using to fix my bindings. It was impressive.
She stood up on the table with me. I cringed as her thin heels moved around me, scared of what they’d do if she were to step on me. On the other hand, the zipper on her suit was, not only still open, but it now went even further, giving me a great view of her pussy and part of her ass.
She hooked a rope to each of the cuffs in my ankles and passed them through two hooks, placed on either side of the top platform, her heels being the only thing that allowed her to reach. Gracefully, she jumped down and from right above my head, she started pulling both ropes, lifting my legs in the air. At the push of a button, the table started lowering again, and with it, my legs started first moving up and then towards my chest, bending my body, leaving only my shoulder blades on the table and everything else in the air, my knees right above my head on the sides, and in the center, a threatening, hard, erected cock.
I groaned in discomfort, not pain. I wiggled around trying to free some of the stress on my body without much luck until she pushed a pillow under my back, which made the whole thing almost ok.
She started pulling the object off my ass; Again, to my surprise, it was actually pleasant feeling it move inside me and slowly slide out until it reached a point when it just popped by itself rapidly. I could see now what my intuition had told me so far, it was indeed a butt plug.
She was fixing it to some sort of leather piece when she commented:
“It looks like you did clean yourself well, almost like you knew what was going to happen,” she laughed. “Now, you realize you can’t move, right?”
I nodded, her face turning serious.
“Well, you better do your damn best to control your gag reflex, or you’ll have a really bad time.”
Without giving me time to speak, she bent over, held my mouth open from my cheeks, just like she did in the bar, and put the plug in my mouth, holding it in with her palm as her other hand latched it behind my head.
I immediately understood the warning. Just the idea of having something that came out of my ass would be enough to make me throw up, but actually feeling it, actually tasting it, was way overboard.
My tongue recoiled trying to avoid the rubbery surface to no avail. The bitterness in my mouth, the smell coming through my nostrils… it was all too much and no warning could have helped that. My throat started to constrict as I gagged. My head tested the strength of the flaps that held my head in place.
She grabbed my cock and started stroking it. It wasn’t like that was going to solve anything, I thought, one thing had nothing to do with the other, but it was so sensitive that suddenly my brain switched priorities, and although I was still disgusted, I no longer had a physical reaction to it. I was, instead, mesmerized by the plastic glove sliding over the skin of my shaft.
“Good boy,” she added smiling. “Do you want to stop?”
I could hardly nod, but I could most definitely not shake my head, and obviously, I could not speak. She laughed
“I’ll take that as a No.”
She crossed her leg over my legs, which now floated next to my head. She started inching forward and started pouring lube on the dildo. Then, some on my ass.
I inhaled deeply, having forgotten the smell that would come with it. This almost made me gag again, but I managed to control myself.
I could feel my eyes opening wide, almost popping out in attention to the dildo coming in contact with my ass. In that position, I could actually see my ass. I thought that maybe that had been the first time in my life that I saw it, not in a mirror. It looked slightly red, and not completely closed, but the girth of the toy was way bigger than the hole.
“Relax,” she said simply.
And she started to push in. To her credit, having me completely at her mercy she could have split me in two, but instead, she went nice and slow, letting me adapt before starting to move. With some discomfort and, what I’d call minimum pain, an inch of the toy finally found its way in. She left it there for an instant and applied more lube on both ass, and toy. She caressed my balls as she started pushing in again, and a drop of, I imagine, pre-cum, splashed in my neck.
She went another inch deep and, although the discomfort was still there, pleasure was appearing also. My dick was even larger, it seemed to me, larger than it had ever been.
She grabbed something from the bed and put it around my balls and the base of my dick. It was some sort of cock-ring that I had never seen before. She pulled it tight and locked it; now everything looked even bigger. Then she continued pushing down.
She went about one-third of the toy in before she switched directions, she pulled it out almost completely, applied more lube, and went back in. With each inch she gained inside my body, I thought I could feel my insides rearranging, and at some point, I could even see a bulge on my belly. With dismay, I realized she had gone all the way in. By that time, my neck, chest, and face were a slimy mess, and, I imagined, the plug in my mouth was the only thing preventing it to go in there too. That was a shitty consolation, pun intended.
I was fixated on the bulge next to my navel, as she expertly and mercilessly hammered me. At this point, I couldn’t tell if there was discomfort, maybe even pain; Blissfully, it would seem that my brain decided to focus on the good sensations.
Even though I didn’t know this was possible, I felt I could cum any moment now and I wouldn’t even need my cock being touched. As the thought crossed my mind, she pull the large toy completely out.
I gasped on my plug-gag. Was she going to leave me like that?
Unexpectedly, she removed the gag from my mouth. My tongue started swirling around and I started gathering the filthy drool that had accumulated to spit it out. Like reading my mind she said:
“No spitting.”
That, of course, wasn’t all. She grabbed a metal instrument from the bed and started inserting it into my mouth, placing pieces of rubber or silicon on my teeth. She then started turning a screw and unstoppably, my mouth cracked open. Each twist opened a bit more until I thought my jaws were about to be dislocated.
She shook my cock, which by that time was acquiring a worrying purple tone. Threads of goo fell on my face, some of them finding the interior of my newly opened mouth. At this point, that didn’t even feel nasty compared to what came before.
She got in position again and started pushing the dildo down. This time, without warm-up, which produced a dull pain. She went all the way in, immediately battering my ass with no reprieve, and, behind that initial pain, it was pleasurable.
Without pause, and with impressive dexterity, she undid the ring on my crotch, threw it on the bed, and grabbed my shaft in her hand, closing on it tight, smashing it in her palm.
Still, I was building up and closing in for orgasm, mostly from the rubbing of the dildo inside of me. It piled up in a different way than it does when my cock is stimulated, remaining on a much thinner edge before orgasm. Finally it happened, and she didn’t stop. She continued drilling as my constrained dick attempted to throb in her hand while spitting large streams of cum she artfully aimed at my mouth. Before I could realize what was happening in the bliss of overwhelming pleasure, I had to start swallowing to avoid choking on the puddle that was settling in my throat.
She cackled, as she continued pounding and milking, even when nothing else was coming out anymore. I screamed, overstimulated to the point where my ears started buzzing and my eyes were starting to blackout. Finally, she pulled the dildo out of me and let go of my cock, leaving it hanging, finally limp, slowly drooling all over me. Goes without saying, that had been the most incredible orgasm I’ve ever had, the most intense pleasure I had ever felt, and anything else that happened and seemed, untoward or wrong, was meaningful at the end. It was all worth it. I would, without a thought, do it again; Or worse.
After a while, she removed the pillow and raised the table again, letting my back and legs finally rest. She removed the device from my mouth, which although it sounds improbable, I had forgotten I had. My tongue explored my mouth tentatively and on its own, not sure if trying to get rid of any remains or savoring them. In my current state, it was really hard to tell.
“What do you say Buddy?”
“Eh?” it’s all I could manage.
She slapped my face twice, one on each cheek, one on each side of the hand. That stung and hurt, especially the second one.
“Didn’t your parents teach you manners? What do you say?
I thought for an instant, presently afraid of what she’d do if I got it wrong.
“Thank you, Mistress,” I finally decided.
“Good boy.”