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(This is a continuation of my story about a fun stay at a Dungeon-for-rent in Chicago. If you haven't already done so, please read "Fun in the Dungeon Ch.1" before reading this story. Hope you enjoy the second part of our little adventure!)
After our exceptionally kinky afternoon in "the Chamber," Tommy and I enjoyed a nice dinner in downtown Chicago. Excited to continue our play, we returned to the Dungeon and freshened up in the sleeping quarters.
"Ready for the Red Room, babe," I asked.
"Can't wait. How do we start?"
"Same as this afternoon. I want you to wait for me in the room, naked, while I put on my new outfit."
Tommy (who I will call Thomas throughout our fantasy session) left me to change into the new costume that I bought for the occasion. This time, I went for the classic dominatrix attire. A black leather corset with attached garter straps. Black fishnet stockings, and black patent leather strappy stilettos adorned with pointy silver studs.
But the main attraction was my big dick! I had strapped on a realistic cock and balls made by a company called Real Cock. (if you would like the details, please read my story "Fantasy Night Ch.2).
I entered the Red Room and found my obedient lover sitting naked in a wooden chair. His eyes almost popped out of his head when he saw what I was wearing.
"Do you like my outfit?" I teased.
"I sure do" he replied, appearing a little nervous. I think he found my look a little intimidating. We've had strap-on sex before, but the dungeon atmosphere, and my leather dominatrix costume, combined with my big fleshy penis, must have been quite a site!
I slowly walked up to my subject, my cock just inches from his face.
"The way you're staring at my cock, I think you would like to kiss it. Is that right? Would you like to kiss my penis?" I asked. And my lover nodded. "You must do better than that. What would you like to do, Thomas?"
"I want to kiss it... and put it in my mouth."
"That's more like it. You may have my cock, but first you must pleasure my behind."
Turning around, I displayed my firm, pale ass cheeks. I stepped away from Tommy's chair and instructed him to kneel behind me.
"Here it is, Thomas. Show me how much you like my ass."
My all too willing lover began to lovingly kiss my ass cheeks and lightly lick my crack.
"That feels nice, but I want more. And I know you want more." I reached behind and spread myself wide, exposing my puckered little hole. "Is this what you want, Thomas."
"Yes"
"Then show me how much you want it."
My man started with just one light flick of his tongue, tickling my anus. It felt wonderful. Tentative at first, he continued licking me, becoming bolder, exerting more pressure, and using broad strokes of his wet tongue.
This was when I noticed that if I looked to my left, I could see all the action in a strategically placed wall mirror. What I view. Me dressed in a black leather corset, complete with garters, fishnets, and spiked heels, having my ass pleasured by my very handsome naked lover.
And... I was sporting a big erect penis!
"You're doing great Thomas. You can stick your tongue inside me if you want."
I spread myself even wider and felt my man's eager tongue slither past my sensitive sphincter and into my rear tunnel. God, what a feeling!
"Fuck me, Thomas!" I panted. And I asked him to take over holding my cheeks apart so that I could fondle my fake penis. I moistened my hand with saliva and rubbed it all over my phallus, making it glisten in the soft lighting.
Now I was watching us in the mirror. My subject was enthusiastically rimming my asshole while I masturbated my cock. I can't even describe what a turn on this was for me. But now I wanted my lover to suck my cock.
"You've done very well so far, Thomas. Now, as promised, you get to suck my dick."
I turned around and presented him with my shiny penis.
As I watched in the mirror, Tommy began kissing and licking the head of my cock! This was about as sexy as it gets. I was fixated on watching us in the mirror as I encouraged my lover.
"Good job Thomas. Lick my penis. Show me how much you love me. Grab my thick shaft and massage it while you lick my glans." I alternated between looking down, and turning to watch the action in the mirror as my wonderful man played with my cock. "Now stick it in your mouth and suck on it," I instructed. And I instinctively began to pump my wet phallus in and out of Tommy's mouth.
As I have often done for my man when the roles were reversed, Tommy moistened a couple of his fingers with saliva, reached around and slowly inserted them in my ass. My already relaxed hole accepted them eagerly, and now I could enjoy the physical pleasure of having my back door gently probed while I watched the incredible cock sucking action up front.
I was loving every minute of this, getting more aggressive with each thrust of my cock, forcing it deeper into my subject's mouth. But I was anxious to move on.
"Good boy, Thomas," I panted. "Now it's time for your reward."
I pulled my cock away as he slid his fingers out of my ass. I took his hand and led him over to one of the devices in the dungeon: a piece of BDSM furniture called a St. Andrews Cross. It's a tall, X-shaped wooden cross, equipped with leather wrist and ankle cuffs designed to restrain the subject. I had my lover face the apparatus and I securely buckled his wrists and ankles to the cross.
Since I was wearing a big strap-on, which I had just used to fuck Tommy's mouth, I'm sure that my man knew where this session was heading. But now that he was strapped to the device, unable to move, naked and fully exposed, this became very real for Tommy. He was about to get fucked by a leather-clad, cock wielding dominatrix!
I stood behind my subject and kissed his neck, then gave it a few playful bites. Again, there was a mirror off to the side, enabling us to watch the action. We both watched as I grabbed my cock and rubbed it teasingly over my lover's ass cheeks.
There was a rack on the wall next to the cross that held a variety of kinky accessories, including several paddles and flogs. I grabbed one of the less menacing looking flogs and swung it back and forth as Tommy watched apprehensively in the mirror. As I mentioned in chapter 1 of this story, Tommy and I are not into the pain thing, but watching us in the mirror... well something just came over me, and I couldn't resist giving my subject a few light swats on his cute little ass! Tommy flinched, but didn't protest. So, as we both watched, I flogged my lover! I needed to restrain myself from hitting him to hard and actually hurting him. This wasn't part of my original plan, but I couldn't believe how much it turned me on. Maybe there's something to this S&M business after all!
"You took that very well, Thomas," I whispered in his ear. "I hope I didn't hurt your butt too much. Let me kiss it and make it better."
I knelt and planted a few soft kisses on my man's behind. But I was on a mission. This was about pegging my lover's ass. So, as he watched in the mirror, I spread his cheeks wide and kissed his puckered asshole. Tommy flinched at my first touch and as I continued to kiss and lick him back there, he began to moan with pleasure. He had never watched me lick his ass before, so I tried to make it as visually exciting as possible. I pulled away from him and jerked my cock while I ran a finger along his crack and teased his hole. I looked to see that he was watching, stuck out my tongue as far as it would go, and while spreading his cheeks with both hands, I jabbed his anus forcefully, tongue fucking him as he squirmed and moaned.
When I had had enough of his ass, I stood and whispered in his ear. "I'm going to fuck you now, Thomas. But only if you beg me. Do you want to get fucked?"
"Yes"
"Not good enough. Tell me what you want."
"I want you to fuck me."
"Fuck you where?"
"In my ass. Jessica, please stick your cock in my ass."
"Well since you asked so nicely," I teased. "Now let's get you lubed up."
I grabbed some lube off the nearby shelf and applied a generous amount to my fingers. Tommy was ready for me and my first finger slid all the way up his ass easily. Gradually, I pressed two, then three fingers into his hole, stretching him out for my cock.
Now as we both watched in the mirror, I greased up my strap-on, making it shine in the light.
Without further ceremony, I rubbed my cock briefly along Tommy's crack then pressed the head firmly against his pucker. I paused, not moving an inch, for at least a minute or two, making my man squirm in anticipation. Then without any warning, I applied more pressure, forcing the first inch into Tommy's ass. He groaned as it popped inside, and once again, I paused, making him wait.
"My next push is going deep, Thomas. You have no choice in the matter, I'm just going to do it. I'm sticking my penis all the way up your ass."
I didn't do it right away. I waited again, torturing my subject with anticipation. Then in one quick, steady motion, I slid my member up Tommy's ass. He moaned loudly as I entered his deepest recesses. My pelvis pressed against his ass cheeks, and I lightly bit his neck as his whole body quivered. I paused again, my penis fully imbedded in my lover, then slowly started to fuck him, sliding almost all the way out, then penetrating him deeply.
We were both mesmerized as we watched ourselves in the mirror. We had made videos of some of our sex play, but this was on a different level. I'm in black leather. My lover is naked and bound. We watched intently as I moved in and out of my lover's back passage and I gradually picked up the pace.
It was time to bring this session to it's inevitable conclusion. I pulled my cock most of the way out of Tommy's behind and applied a fresh coat of lube, greasing it up for my final assault.
"Are you ready to come for me, Thomas? I whispered in his ear.
"Yes, I'm ready Jessica," he panted.
I squeezed a big glob of lube into my hand, reached around and applied it to my man's erection, And as I pushed my phallus up his rear, I started to run my hand along his shaft and over his swollen glans. Tommy was shaking all over and breathing heavily as I fucked his ass and masturbated his penis. I squeezed his cock hard and forcefully penetrated him deeply. It wouldn't be long now!
I switched to shallower, rapid thrusts up his ass, and pumped away at his shaft as fast as I could, gripping him even harder as my hand ran over his lube-slickened head. Tommy screamed as he suddenly began to shoot into my hand! We both watched in the mirror as thick streams of warm cum shot from my lover's cock as his entire body convulsed violently.
Still watching in the mirror, I withdrew my cock from Tommy's ass. I had captured most of my man's juice in my cupped hand, and now I used it to coat my cock, fantasizing that I had actually cum inside my lover. I slowly inserted myself back in Tommy's anus one last time, watching as it slid in easily, well coated in lube and cum,
Tommy had obviously had enough. I slowly exited his rear.
"Good boy, Thomas," I whispered.
I unbuckled the restraints, we embraced in a long kiss, and we retired to the bedroom.
It had been a perfect day of fun in the Dungeon!
-Jessica B.
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