“Bend over the pool table and spread those cheeks, boy,” Jack demanded. “I’ll give you something to remember.”
Jack squirted some more lube down the crack of my ass and used his cockhead to work the lube around my gaping hole.
“Reach back and guide my cock into your sphincter,” Jack instructed.
I positioned the enormous bulb at my once tight bud and began to push back, ready to feel the power of Jack’s throbbing rod buried in my empty ass.
I pushed back, but Jack also drew away, teasing me and not letting his cockhead penetrate my horny hole.
“Beg for it bitch,” he barked.
“Please, Sir, please don’t tease me. Fuck my virgin ass. Shove that big cock in my empty ass.”
Without warning, Jack grabbed my hips and plunged forward, impaling me on several inches of his wickedly fat fuckstick. I stifled a scream, biting on my fist to keep from howling bloody murder. The butt plugs and rubber dick had loosened me up, but I was nowhere near ready for the girth of Jack’s giant mushroom head as it split my ass wide open.
“Take it slut,” Jack laughed as he plunged inch after inch of steel fire into my tortured rear-end. I was seeing stars as I fought back the urge to scream, firmly trapped between Jack and the pool table, incapable of fighting off Jack’s onslaught. He was literally branding me with his hot poker and I knew I must submit to his abuse. I was beyond the point of return and I only hoped the intense pain would subside shortly.
“That is still one tight hole, boy,” Jack sighed as I felt his balls bang against mine, his entire length now encased in my man-pussy.
He left his cock firmly planted for some time as I struggled to accommodate the massive spear. With a steady slow pace, Jack began to fuck my ass. The searing pain was slowly replaced by a not unpleasant fullness as Jack worked his rod in and out of my hole. As his fat boner massaged my prostate, I began to enjoy the fucking, an incredible mix of pain and pleasure that made my dick as hard as stone.
Jack pulled all but the plum sized head from my depths and remained motionless. I pushed back, wanting to feel more of his rod buried up my anus.
“You want it, huh?” Jack snorted.
“Yes, Sir,” I pleaded. “Fuck me hard. Take my cherry ass. Make me your bitch.”
“You are my fucking bitch,” Jack laughed as he rammed his tool back into me. Taking a firm hold on my hips, Jack began to piston fuck me with reckless abandon. With each deep stroke, I let out a grunt.
“Oh yea, fuck that hole, Sir. Fuck me deep. Fill my ass with your seed.”
For twenty minutes, Jack fucked me with unrelenting stamina. Periodically he squirted some additional lube on his piston, keeping my ass wet and willing. Without touching my own dick, I erupted twice while he fucked me, shooting two sticky loads all over the floor. His cock had found my g-spot and while my ass ached, I didn’t want him to stop.
At long last, I felt his cock start to twitch in my tattered hole and with a loud moan, he erupted deep into my bowels, squirting an endless load of jizz up my ass.
“Take that cum, bitch. I’m unloading my seed deep into your pussy. Holy fuck,” he sighed.
Jack remained hard even after filling my ass with his spunk and he continued to fuck my sloppy hole for several more minutes. Unbelievably, I came a third time as he pounded my poor butt.
Finally, Jack pulled his enormous rod from my ass and I felt his huge load leaking from my gaping hole.
“Lick me clean, slut,” Jack ordered.
I happily took his fat pole into my mouth and swallowed every last drop of his oozing cum, even as his warm jizz leaked from my ass and ran down my legs.
“You may have some trouble sitting down for a couple of days, boy,” Jack laughed as he reached for his shorts.
“No problem, Sir,” I sighed, my ass already throbbing with a dull ache.
“Fuck Craig, you are one horny little slut. I had no idea how easy you would be to convert to a full-time bottom.”
And I was converted. My ass remained tender for a week but I couldn’t wait to service Jack again.
On Wednesday Jack called my cell phone just before lunch. “Meet me in my van in the parking lot in twenty minutes.”
Jack had a custom van with a convertible couch in the back that he and Martha took on roadtrips. As I walked up to the van, the back door slid open and Jack ushered me inside.
“Strip down boy and get between my legs,” Jack demanded.
Here I was in the parking lot of my office, naked in the back of my neighbors van, giving him a blowjob in broad daylight. But I was happy as hell when Jack fed me a huge load, better than any lunch plans I could envision.
These lunchtime blowjobs became a regular event, as Jack would fuck my face two or three times per week. As the ache in my ass finally subsided, I begged Jack to fuck my ass during one of the lunch sessions.
“I’ll fuck your ass, bitch, but not here in the van. Too cramped. You got any ideas?”
I immediately thought of the mensroom in the basement. “Meet me in the mensroom on level 0 in five minutes,” I replied.
Sure enough, the basement was deserted, so I grabbed a big wad of liquid soap and made my way to the last stall, stripped naked, and waited for Sir.
“You in here Craig?” Jack asked as he sauntered into the mensroom.
“Last stall,” I croaked, nervous but horny as I lubed my recuperated hole with the liquid soap.
Jack opened the door and laughed out loud. “You are the fucking horniest little bitch I’ve ever turned.”
I unzipped Jack’s trousers, fished out his magnificent tool and went to work. Within minutes, he was rock hard. I bent over the toiled and spread my sudsy cheeks. “Please fuck me, Sir,” I pleaded.
Jack pounded my hole without mercy, equally as turned on by the thought of public sex as I was.
“You like that, don’t you bitch?” Jack chuckled.
“Sir, yes, Sir,” I grunted as my ass took each deep, powerful stroke.
Luckily no one entered the restroom and when Jack finally unloaded into my ass, I collapsed exhausted onto the toilet.
As I taught several classes that afternoon, I felt the remnants of Jack’s mighty load leaking out of my again sore ass. Between classes, I returned to the basement bathroom and jerked a big load into the toilet bowl that I had recently been bent over.
Jack never again had to raise the issue of revealing my indiscretions to my wife. I am now his willing bottom slut and look forward to our regular sessions. He tells me a couple of his Navy buddies are coming to town next week for a reunion, and I’m expected to be the main entertainment. To be honest, I can’t wait. The thought of servicing multiple cocks already has my little clit rockhard.