I was obviously going to get fucked. That was fine by me, while I had found it a bit humiliating I soon got over that, and it turned out that I actually enjoyed it a lot.
Ma’am’s fingers disappeared.
“Relax boy.”
I felt something large at my entrance.
“You will remember this old friend I imagine.”
I began to stretch as a large phallus pressed relentlessly against me. I could feel some knobs and lumps, it was the very large dildo that had been used on me before. It’s greatest circumference was at its end and it narrowed as it went along, but it was covered with smooth yet prominent knobs.
I relaxed as best I could, the painful part was getting the large end past my sphincter. It kept moving slowly into me without hesitation. I had forgotten how much the initial penetration hurt, I grimaced and instinctively tried to clench down. It didn’t matter, the huge invader kept coming, I forced myself to calm down, the moment I did it slipped through and the pain faded. More and more of it entered me until it reached painfully deep inside.
Mercifully it stopped. Ma’am must have seen the sudden tension in my body and it moved back a very small amount.
Nothing happened for a couple of minutes, Ma’am was clearly doing something behind me, maybe she was locking it in place but I didn’t know.
I felt her hand under my chin, lifting my head. I was blind behind the hood but I could feel her eyes staring at me.
“Don’t cum boy. This is your last chance to show me that you have learned some semblance of control.”
From inside the hood I mumbled, “Yes Ma’am.”
Her hand moved, and so did the dildo. It slowly pulled away, probably about five inches before going back in again.
I didn’t understand, Ma’am was still in front of me. For some reason I looked around despite my head being wrapped in tight leather. I didn’t think there was anyone else here so what was going on? Ma’am answered the question for me.
“That man who was here delivered something that I’ve borrowed from a friend. A fucking machine, a very nice one too.”
Now I understood, there wasn’t a person behind me, slowly pushing the big dildo in and out, it was a machine.
“Let’s see what this baby can do, shall we?”
She paused, “well?”
“Yes Ma’am.”
I mumbled from behind the hood.
“What was that boy?”
“Yes Ma’am, please use the fucking on me.”
“Are you sure boy? You don’t sound very sure.”
She loved this game.
“Please Ma’am, please fuck me up the arse with a huge dildo. Make the machine fuck me for as long and hard as you want to Ma’am”
“Well I was just going to mess about for a few minutes, but clearly you want a whole lot more than that. Good boy.”
The dildo immediately started moving faster inside me. At maximum penetration it was very deep indeed, almost painfully so, but Ma’am had set it up just right. It was withdrawing about five inches before burying itself deep in me again. Ma’am speeded it up a little more and my cock stiffened in the cage.
There was something quite scary about being taken like this. The dildo wasn’t going too fast yet but I could feel the power of it. There was no hesitation, no pause, it just went in and out.
I felt some lube trickle down my crack to ease its progress.
The length suddenly changed, becoming shorter. It only withdrew a couple of inches now, meaning I was much fuller most of the time. I could feel my body being gently pushed forwards each time it filled me.
Ma’am slowed it down slightly.
“Let’s see how this feels boy.”
Suddenly I felt the dildo twist inside me, one way then the other. The small knobs covering it were now being dragged up and down, and across my prostate gland. To my shame it felt very good and my cock agreed.
“Oh, look at that. Is that good boy?”
“Yes Ma’am.”
I still wasn’t sure about the feelings that being penetrated gave me. They were definitely exciting, but it was odd too. I decided to enjoy it, it wasn’t like I had a choice anyway.
The twist had added something extra to the mix for sure. The now familiar tingle in my groin had become quite intense. The dildo wasn’t going to stop, it would pound away until Ma’am stopped it.
I felt a surge of submissiveness, I couldn’t help myself. I wanted the huge dildo deep inside me, filling me, rubbing against my delicate passage.
Ma’am increased the length of the stroke and the speed. I was getting a proper seeing to now. My cock was straining and tingling. I was feeling very hot and bothered under the tight leather hood. Ma’am left well alone for a few minutes, watching me carefully.
Suddenly I felt the beast withdraw an inch or so. I didn’t want that, I wanted all of it in me, I wanted to be full. Ma’am hadn’t strapped me down in her usual vigorous manner and almost unconsciously I began to move back into the thrust. I could use my arms and legs to force my arse onto the dildo each time it pushed into me.
I let out a little moan of pleasure, I wanted to be fucked harder. Ma’am didn’t oblige and left me desperately searching for more. The strap around my middle dug in each time I tried to push myself back.
She knew what was happening, of course she did.
“You love this, don’t you baby? Do you want more? More big cock inside you?”
“Ohh, yes Ma’am. Please fuck me harder.”
I felt myself get even hotter under the hood but I didn’t care. I did want more, it felt too good not to want more.
Instead Ma’am shortened the stroke again, and slowed it down. She kept the twisting motion going though. I moaned, this wasn’t what I wanted. I arched my back and tried to fuck the dildo. My hips started moving, trying to get more friction from the twisting knobs.
It wasn’t enough though, whatever I tried to do with my body I couldn’t get as much stimulation as I wanted.
“You’re desperate for more cock, aren’t you baby?”
I moaned.
“Yes Ma’am.”
“How desperate?”
“Please Ma’am, I want to be fucked harder, give it to me Ma’am. Let the machine loose on my willing arse.”
“Are you sure baby?”
“Yes Ma’am, yes!”
The machine moved, back to its original position, where it could fill me completely. Ma’am kept the strokes short, I was properly stuffed, and the twisting felt utterly delicious.
My cock twitched with pleasure, then suddenly the machine stopped.
“What are you trying to achieve boy?”
I wasn’t sure what she meant, I was just trying to get as much pleasure as I could.
“I don’t know Ma’am, I just know that it feels really good and I want more.”
“Are you trying to have an orgasm boy?”
Oh shit! She was right, I would have ridden that big cock as hard as I could, until the inevitable happened. I had never cum from anal before but I knew that I could, and I knew that I had got completely carried away again. I had wanted Ma’am to allow the machine to take me to an orgasm.
“Ma’am, I just wanted to feel good, you know how much I enjoy being penetrated. But I guess if you had kept going then I would have cum.”
“You were actively trying to get as much pleasure as possible, and there would be a definite end result to that, wouldn’t there boy?”
“Yes Ma’am, I’m pretty sure there would.”
I didn’t know what else to say, anything else I said would either be a lie, or incriminate me even more.