Role of a Lifetime
By: Kenneth Kirk
(© 2021 by the author)

The author retains all rights. No reproductions are allowed without the author's consent. Comments are appreciated at...

kkirk@tickiestories.us

Chapter 32

I lathed Brant’s sphincter with saliva for a minute or two, probing into his warmth from time to time and feeling his sphincter relaxing.  I backed away and applied some lube to my fingers, then placed the tip of my middle finger against the quivering rosebud where I wiggled it.  He was ready.  His hole opened with minimal pressure so I could insert the middle finger, knuckle by knuckle as he moaned his pleasure.

For a couple of minutes, my finger firmly probed, twisted, and thrust inside his sphincter, making his anus ready physically and emotionally for deeper, greater penetration.  He grunted each time my finger pushed deeper and groaned each time the finger rotated to massage new areas of the surface of the guardian muscle.  My index finger joined its brother and together they spread him wider.  I pushed all the way in, turned my hand down so the pads of my fingertips could introduce themselves to his awakening prostate.

“Ooooooh!” he moaned.  His dick was so hard it hovered below him almost parallel to his abs, dripping continuously onto the bed.  I separated my fingers a few millimeters so each finger could track along the curved side of the sex gland.  For several minutes, I thrust my fingers into him gently, caressing his prostate lovingly and he moaned and wriggled around my fingers.  As I petted his prostate his breathing grew heavier and somewhat ragged.  “Oooooh!” he moaned again and again.

“Do you want more than little fingers in your butt?”  I held still with my fingers straddling the bulge of his prostate.

“Ooooh, ye-yes!”

“Are you sure?”

“Fuck, yes!  Give me cock.”  I didn’t move for a few seconds.  “Please.  Sir.”

“Good,” I said.  Slowly I withdrew my fingers while, with my other hand, I picked up the small dildo.  When my fingers were out of him, I lubed the rubber dick and brought it to his sphincter.  His rosebud had grown pink and swollen with the attention it had been receiving.  It throbbed with each beat of his heart almost in time with the bobbing of his dick below as it twitched and drooled.  I put the tip of the dildo against his opening and it went immediately in a fraction of an inch.

“Oh, god!” 

“If you want it, push back on it,” I ordered.

Brant arched his back to push his ass back and his flawless butt swallowed several inches of the black cock while he cried out, “Ooooh, fu-u-uck!”  He paused, drew a big breath, shifted his knees a couple of inches nearer me, and pushed back again until he had all 6 inches.  “Ooooh, ye-es!” he cried.

Frankly, I was amazed at how easily and eagerly he had impaled himself on the dildo, clearly feeling little or no pain.

“Good boy!”  In reward I turned the dildo within him to give him some delicious friction.  I pulled it slowly out and began thrusting slowly, sensuously.  I noticed my own cock was excited by all this ass play as it stood out at full attention while I worked that dildo into that gorgeous asshole.

 I drove the dildo with my left hand as I grabbed the leather slapper with my right.  Catching him unaware, I swatted his butt cheek with the slapper.  It was hard enough to sting a bit and leave a reddening in the pale flesh.  It was hard enough to get a startled yelp from Brant.

“Lie down flat!” I ordered.

He complied, which brought his legs into the sides of my knees and changed the angle of the dildo protruding out of him.  I shifted to put my knees outside his legs and pushed his legs together.  Holding the dildo in place I lay down on his back, my dick snug against his perineum and balls.  He lay beneath me with his head turned to the right.  I grasped the back of his head to hold him down while I dropped my face beside his.  He looked over at me with intense vulnerability as I narrowed my eyes at him. 

“You’re doing well so far, boy.”

“Uhm, thank you, uhm, sir.”

At the back of his head I tugged on his hair which lifted his chin somewhat.  I leaned in and took his mouth, not in a gentle loving kiss, but in a ravaging assault full of manly lust and passion and control.  While my lips and tongue conquered his mouth he whimpered like an alpha dog just taken down by his challenger.  While I tamed his mouth, I rolled off him so I could get the right angle with my arm to resume the pillaging of his needy hole.  I could feel him moving back to meet my thrusts.  That pleased me because he was obviously so turned on he was working subconsciously to amplify the friction.  I released his mouth and moved completely off him.  He looked at me with a little fright and a lot of erotic emotion and submissiveness.

“On your back,” I growled and he flipped himself.  I moved back to his legs, pushing them straight up from the mattress and over his head.  Two inches of the black dildo protruded from his furry butt.  I picked up the slapper and ran it across his side while I resumed plundering his hole with the dildo.  His dick was red with the blood that made it so swollen and it was drenched with precum. 

I twirled the slapper in my hand so the feather-duster was available.  Without stopping the movements of the dildo, I lightly tickled his balls and perineum with the duster, eliciting a weird yelping moan from him.  His cock jumped and he reached out to take it into his hand.  I quickly twirled the slapper again and slapped the back of his hand while yelling, “No!  What did I tell you about not touching your dick?”

“Ow!” he cried and dropped his hand.  “Couldn’t help it,” he explained lamely.

“Don’t do it again!”  I sounded like a South LA dominatrix and almost laughed at the look on his face which was 50% horrified at what had happened and 50% extremely excited.

In pretending anger, I jerked the dildo out of his ass and threw it onto the floor, leaving his hole gaping open and painfully empty, I supposed.  I took a few seconds to lube my cock while he looked at me fearfully.  Carefully, but quickly, I slid my randy prick into his very welcoming warmth, relishing the fleshy squeeze as I pushed all the way in.  Even though he had been thoroughly fucked by the small dildo, I had 2 more inches in length and significantly greater girth, so his minimally trained hole had to stretch noticeably the instant I sank into him.  I don’t think he felt pain since everything was already so relaxed in there, but the feeling did surprise him.

“Oh, baby,” he moaned.

Once I was fully inserted I leaned down until I was flat on his torso, pulling his legs back to his sides, opening his ass even wider, and bringing my face down to his.  Holding his ankles at my shoulders, I reached around to grab both wrists.  I brought his hands up to the top of his head and held them firmly there.  All the while I held his gaze while I lowered my face toward his.  When I was only a few inches away, his lips parted and his mouth opened to receive my kiss.  But I didn’t kiss him.  I stopped maybe 4 inches above him and spat into his open mouth.

“Wha--?” he started, but I stopped him with a searing kiss as I finally pulled back and gave him a hard thrust into the guts.  Again my kiss was a ravaging of his lips and tongue.  I pushed my lips, even my teeth into his oral cavity forcing him to open wide while I almost ate his tongue.  Meanwhile I pounded him as hard and fast as I could in that position.  Finally I had to release his mouth because we were both so short on air.

I pulled off a few inches while we gasped for oxygen.  As soon as he had some air, he started wailing to match my grunting as I threw pipe into him at an amazing pace.  Still holding his hands behind his head, I fucked his ass as long and as hard as I had ever fucked before.  It was so good!

“Awwwww,” he wailed.  “Fuck me!  Fu-uck me, Sky!”

I rammed him as deeply as I could and then stopped completely because I was about to cum myself and wasn’t ready to end this marathon.  His ass muscles began to clench around my cock as if trying to milk the seed out of me.  I took a deep breath and pulled out of him as I released his hands and pushed myself up until I was on my knees.  I stared down at him and was touched deeply by the level of trust he was exhibiting.  Shit, this was fun!

We stared at each other for a moment.  I saw his hand twitch a few times and I knew he was about to grab his poor dick to get his much-deserved relief.  Staring me in the eyes, his jaw clenched and his hand shot out.  His palm landed on the back of his rigid shaft and his fingers closed around it.  He’s like a rebellious little boy, I thought as I stifled a laugh by grimacing at him.  I swatted his hand with the leather slapper and bellowed, “No!”

He gave his dick a stroke and I brandished the slapper at him while I grimaced to look as mean as I could.  “Do not!” I shouted as I swatted his hand hard enough to hurt.  He dropped his hand and the defiant look on his face.  He seemed emotionally hurt more than physically hurt.  At that moment he was not having fun. 

I moved a bit further back from his body and said in a calmer voice, “Get up onto your knees and face the wall.”

He looked surprised, but meekly complied.  When he was facing away from me I moved forward until I was against his ass.  I put an arm around his torso, pulling him back against my chest.  I snarled into his ear, “You broke the rule – twice.  Now I have to restrain your hands because you’ve been a bad boy.”

“No-o-o-o!” he wailed like a 17-year-old grounded just before the prom.

“Ye-e-e-e-es,” I echoed back sarcastically.  “Now, move up until your knees are a few inches from the headboard.”

He did.  The headboard was comprised of a couple of white bars running horizontal across the entire king-size bed and several vertical pipes to stabilize the structure.  It was quite sturdy and offered a multitude of locations for tying off a restraining rope.

“Good boy.  Now extend your arms to the side and grab the bar.”

He did.

“Don’t let go.”  My voice had lost its angry edge and was just firm at this point.

I picked up a wrist band, wrapped it around his wrist and pulled it snug.  “Too tight?”

“No.”

I tied the string into a knot  I looped one piece of the nylon rope through the ring on the wrist back and tied the end to the post on the side of the headboard.   He whimpered and I wasn’t sure if it was a hurt whimper or an aroused whimper.  When I was sure the rope was secure, I repeated the entire process with his other wrist.  When I was done tying him up, I moved back behind him, added a fresh squirt of lube to my rock-hard battering ram and scooted up to his ass.

I ran my cock along his crack and across his swollen rosebud.  “Just so you know, I am going to fuck you until I fill you with my big load.”

“Ye-es, Sky.  Fill me,” he said in a begging tone.

I lifted his ass until I could slide my knees forward and position my cockhead at his entrance.  His hole was gaping, wet, and begging for me.  I pulled his body down onto my lap, impaling him to the max with my 8” in about 2 seconds.

He gave a guttural yelp as he settled his butt cheeks against my thighs.  I reached in front of him, found his nipples, and pinched them.  He yelped.  I brought my hands back to his butt and raised him about 4” off my thighs.  Holding him steady I raised my own hips to drive my cock up and into his intestines.  He grunted.  I pounded.  He whimpered.  I pounded.  He cried out, “Oh!”

For several minutes I thrust up into him.  Then for a couple of minutes I rested while he rose off me and fell back onto me in a beautiful self-fuck.  I was so close to cumming I thought I would once or twice, but I did not.

Without withdrawing I pushed him higher so I could pull my knees back and get into a taller position.  I moved back a bit, pulling him with me and pushing his shoulders down as I moved.  This realigned our bodies so I could fuck him from behind rather than up from below.  That allowed me to put more power into my thrusts.

I knew I wouldn’t last long once I resumed my fucking, but I also didn’t want to last too long as we were both tiring and I had to be able to get him off before he was too exhausted.  So I took a deep breath and drove into him for all I was worth.  After a minute and at least 100 pushes into him, my balls leaped up to my groin and I fired.

“Take it, babe!”

“Oh, yeah!” he cried as he squeezed me each time I shot, amplifying the sensations and probably the power behind the shots.  With each blast of cum, I thrust forward into him as we both screamed, “Oh!”

When finally my seed was spent, I wanted to stay inside his warm center for a long time, but I wanted to get him to cum spontaneously as soon as possible, so I pumped him a few more times, then pulled out leaving him sort of hanging off the headboard with cum starting to drip from his ass and precum dripping from his dick as he moaned in frustration at being empty and not able to cum.

I sat back on my haunches and picked up the long, thick “Big Daddy”.  I lubed it liberally and got back to my knees, still breathing hard to recover from my exertion and my ejaculation.  I moved forward, grasping Brant around his midsection with my left arm while my right hand guided the fake cock to his cum-covered bum-hole.

When he felt the rounded tip of the dildo against him, he whimpered, again in fear or excitement, I couldn’t be sure.  Knowing he had never had anything this thick in his perfect butt before, I rotated it with only the tip inside.  I pressed against the walls of his sphincter as I shifted the pressure in a circular motion.  He gasped for air and began to moan.  I increased the pressure and a little more went in, but still he had not yet taken the full girth.  I gradually pushed harder and the resistance his body gave to forward progress increased until finally there was a pop and the dildo was through the sphincter and into the inner sanctum.

“Oh my gawd!” he screamed.

I stopped with about 2” inside.  I began pressing outward again to massage the interior of his sphincter into submission.  Soon the dildo began moving, opening him wider and then deeper than ever before.  “Oh, oh, oh!” he cried.  When the dildo’s balls hit his perineum, I was very impressed.  By this point, he was simply moaning constantly, except when he had to draw in some air.

“Good boy,” I said soothingly.  “You’ve taken it all.”

“Feels s’good,” he gasped.

“What do you want?”  Of course I knew the answer to that.  But I want him to admit it, to hear himself tell me he wanted to be fucked.

“Oh, make me cum!”

“Do you want to get fucked by this big dildo until you cum?”

“Uh, ye-es,” he mumbled.  I was sure he wasn’t sure he wanted that, but above everything he wanted to cum and if that meant getting fucked by this big dildo, he would take it.

To be sure he was used to the size and not in any pain, I gave him several deep thrusts slowly and firmly.  He pushed back, opening his ass as much as he could and proving to me that he was comfortable enough to want more.

I picked up the pace as I pounded him with the rubber cock which I aimed as much as possible for his prostate.  From his gasping and wailing I think I accomplished that well.  Each time the dildo passed over his prostate he gasped as though that had never happened before.  After about 2 and ½ minutes his voice began to rise in pitch and volume which told me he was almost there.  I picked up the pace to the maximum I was capable of as his breathless high-pitched wailing became so loud I wondered if he could be heard on the street 23 floors beneath us.  Only a few more pounding thrusts were needed.

From beside him with my arm around his belly, I looked at his dick.  He stopped wailing as he drew in an enormous volume of air, held it for a second and then threw his head back for a full-throated soprano scream that hurt my ears.  His cock exploded a cum-shot that lasted a full second and released at least a table spoon of spunk across the bed underneath him and struck the wall so hard I thought it probably chipped the paint.  Three more shots almost as intense but not quite as full still managed to reach the wall in front of him.  I counted 8 more shots onto the sheets below him until he was finally done.  I had dropped the power behind my thrusts until the dildo was just rocking inside him.

Slowly I withdrew the dildo.  As quickly as I could I untied the restraints as he gasped for air and cried a bit.  Gently I laid him on the mattress far enough to the side to avoid most of the now-cold cum on the sheet.  Tenderly I kissed his forehead and jumped down to get a wet and warm washcloth for a quick mop up of his now hyper-tender ass.  I pecked him on the lips and said, “Just rest for a minute.”  I lay down on the far side of the bed away from the horrific mess on the sheets and tried to read his thoughts from a couple of feet away.   

Brant looked over his wrist band at me, appearing somewhat vulnerable and a little subdued after all our activity.  His intense stare and his somber lips made me wonder what was going through his mind as he processed all we had done over the past hour and a half.

To be continued...

Posted: 11/19/2021