Jason Part 4

The expression on my face must have resembled that of a frightened deer caught in the headlights of a car, because Mistress Maureen chuckled and told me, “I had this dildo specially made just for you. It was designed from the measurements of your own erect penis.”

I’m not that big, I thought! But then I looked down at my own dick, which was still sticking straight up in the air despite my fear. I guess my being down on the floor on my knees, and staring straight at the realistic-looking dildo —— the color matched her skin-tone perfectly —— that was now right in front of my face, that from this vantage point, it’s a whole different story. I was going to be on the receiving end of this thing!

I looked at this by now close-up dildo with a mixture of dread and curiosity —— and, secretly, a bit of anticipation, too, but I wasn’t going to let that on. This dildo was going to be plundering my virgin asshole in another few minutes!

Mistress Maureen grasped my chin with her hand and whispered, “Open your mouth, Jason darling. I want you to think of this thing as if it were a living part of my body. I want to feel your tongue on it. I want to feel it sliding into your mouth. Open up now.”

With her other hand wrapped around the dildo, she inserted it between my lips and let go. Her hands then rested on my shoulders as I licked all along the head of this thing. It was hard, but soft on the outside like skin, and it did indeed feel a bit like a real thing. Except that it was cold. But my mouth was making it warm now.

She pushed it a little further into my mouth, so that it was just touching the back of my throat. For weeks now, I had practiced doing this on a smaller, plain dildo, so my gag reflex was fortunately not hindering me now.

Then she began gently fucking my face with it. Just a little in and out movement, as I continued to tongue the thing. I could handle this, I thought.

A couple of minutes later, Mistress Maureen stepped back, away from me, and instructed Tom to prepare the bed and me.

She watched as Tom quickly and efficiently went to work. He placed a bolster on the bed, close to the foot of it. Then he told me to kneel on the bed, with my knees spread wide around the bottom of the bolster, and I was to lower my stomach and chest so that they rested on top of the bolster.

It was soft, like a bunch of pillows piled on top of one another, but it was strong, so that I didn’t sink down, as just plain pillows would have caused me to do.

The bolster was kind of cube-shaped with rounded edges, but it was slanted so that my ass was raised higher than my chest and head. Between my thighs, the bolster had a ring with two soft leather straps about one inch wide attached to it. Tom pulled the straps up and fitted them so that each ran back along my inner ass cheeks —— holding my ass wide apart and immobile —— and then attached the straps to the sides of the bolster, one strap on either side of my waist.

Though my arms were free, I couldn’t move my hips at all.

I heard Mistress Maureen ask Tom to bring her the lube and then she dismissed him back to his corner.

This was it! It was going to happen right now!

When I first got on the bed I had turned my head so that I could watch everything in the mirrored wall. I now watched Mistress Maureen standing behind me, as she squeezed gel from the tube onto her palm and grasped her strap-on dildo in her hand and rubbed the lube on. She was looking straight at me, spread out and waiting helpless on the bed before her.

Then she stepped closer to me, and I felt her slippery finger penetrate my asshole. She added more lube and worked it in. A second finger now helped to loosen my sphincter as she massaged the lube in and out, spreading the slick stuff around the outside of my asshole a bit and then inside me again.

My eyes had drifted shut and I was floating in heaven by the time I realized that she had suddenly replaced her fingers on my asshole with her strap-on dildo. Did I say the dildo was soft on the outside? Now it felt like steel. A battering ram seeking entrance into my most intimate personal place.

“Open yourself for me, Jason. Let me in now, darling.”

My body was not my own anymore. I knew that. I was her slave and I belonged to her, completely. She wanted in, and —— truth be told —— I wanted her in, too.

Mistress Maureen leaned into me again, pressing the head of the dildo harder against my asshole. I arched my back, tilting my almost immobile pelvis a bit more, and pressed down, pushing out against her as I had been trained to do. Pushing out actually facilitates easier penetration. Now I was going to find out exactly how.

Plop! As soon as I began pushing out, the head of her dildo went inside of me. And in it slid in one long relentless stroke, down deeper and deeper inside my rectum until all of it was now in. I stopped pressing, but suddenly now felt a little nauseous because of all the pressure I put behind getting it in. I had to close my eyes for a moment.

I was filled! With her! Or at least with the dildo that was attached to her. She was wearing the dildo that was an identical twin to my own cock. I suddenly realized how close that made us!

I opened my eyes and watched her in the mirror. She had waited a couple of minutes for me to fully experience this new sensation.

Then she grabbed my hips with her hands and pulled the dildo out of me a little bit. And then she pushed back in again. Out and in. Out and in. Each time she penetrated my ass a bit more, the stroke longer and a little stronger.

Her hips moved powerfully against my ass. Her strap-on slid in and out of me faster and faster until she had developed a steady, yet slightly abrasive rhythm. It felt good, but I can’t say it didn’t also hurt a little.

Who was I kidding? Mistress Maureen knew me. She knew exactly what I “secretly” wanted. She knew I wanted this, in just this way. I wanted it steady. I wanted a fast pace. I wanted it hard and yes, a little abrasive.

I wanted to feel exactly what I was experiencing. I felt it all. Every bit of it.

And I watched it all happening in the mirror.

She leaned forward over my body and slid her hands up my back to massage my neck and shoulders. Then she stood up again and increased her rhythm. Faster and faster, she fucked me harder and harder. I was going to come, I just knew it. And she never told me I couldn’t! Did that mean that it was allowed!

She then suddenly reached down underneath me and grabbed my balls, pulling on them, and squeezing them a little. Oh, man!

I grunted. I moaned. I came —— loud and hard!

The next thing I knew, Mistress Maureen was pulling out of me very slowly, until I heard another “Plop!” as the dildo’s head at last came out.

I expected to be released now, but I should have remembered that Mistresses never do what is expected.

“Don’t move, Jason darling,” I heard her say. “We’re not done yet. The night is still young. Oh, Tom! Come here please.”

(End of Part 4)

Copyright © 2001 The Dominion Group MissBonnie

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