He Always Has a Plan - 1. Chapter 1

I sat on the train watching the trees pass as I sipped on a brown bagged 24oz can of Bud Light. Nervous and excited with memorized instructions, I felt my cock stir in the well-worn “uniform” under my shorts as my mind wandered.

I finished off the beer, grateful for the slight buzz, and noticed I was only about ten minutes from my stop. I got up and grabbed my bag which had very little in it to find the bathroom to throw out my empty cans before arrival, ignoring any suspicious eyes from the other passengers on the crowded train. The pain in my bladder reminded me of its fullness and longing for release in the nasty train toilet knowing better than to think I was allowed. The use of the bathroom on the train for anything more than sending pictures on my journey was forbidden.

I checked the time, lock the door, shoved my tight denim shorts down, and held it under my fat furry ass to take a picture, making sure the worn straps of my jock were visibly framing my round, perky cheeks.

Your hole is almost at the station, Sir.

I reveled in the familiarity and ease of speaking in such a way that used to be so foreign and filled me with discomfort back then as I sent the photo with the short notification of my whereabouts. A smile crept across my face and I followed up with something silly as was my usual habit.

<pig, angel, devil, tongue, and spurt emoji>

It wasn't necessary but it had become something of a tradition because the one thing that kept me coming back, kept me comfortable, and felt safe when my limits were pushed well outside the lines of what I thought was my comfort zone were the underlying tones of playfulness, connection. A glimmer of giddy desire in His eyes behind the stoic face when I was servicing him. The freedom to laugh in disbelief and pleasure when a predetermined limit had been stretched then erased by new experiences. The comfort of not taking anything too seriously yet trusting Him to have no hesitations when a plan was put in place.

CC: Gabriel will be there to pick you up.

I could read the untyped words that would’ve said I’ve missed you before he sent another message.

CC: He has been briefed on your tasks to complete before your arrival, boy.

My heart fluttered and my cock twitched - The game was afoot.

Thank you, Sir.

I saw the large black SUV with its suited driver standing outside, complete with captain's hat, as I stepped from the Long Island Rail Road. You’d think I was getting picked up by the Secret Service and I smiled to myself thinking back to the specific plan sent to me earlier this week. My normal luxury accommodations were stripped away and I was meant to take the train or jitney like the rest of the weekenders as opposed to the helicopter service He had normally spoiled me with. There was always a thrill when I felt like an escort in my overtly, usually quite musky, skimpy attire He had requested I wear on the public journeys He would send me on to meet him.

As I walked down the steps toward my ride in waiting I caught a glimpse of the man I had become familiar with and was reminded of how hot he was. With his aviators, square, tan, clean-shaven jaw, broad shoulders, and barrel chest - all enhanced by the unusual uniform of an expertly tailored suit. I couldn’t imagine how hot he must be in a suit on that warm day and was grateful to be in my cut-off shorts and t-shirt that barely reached my waist with sandals on my freshly pedicured feet.

“Good to see you again Aden,” said the driver’s deep voice.

“You too Gabriel.”

I went to get in the back when he stopped me and opened the front passenger side door.

“We have an errand to run,” he said, taking my bag and placing it in the back seat.

This is odd I thought, but just as I climbed in and clicked the buckle of my seat belt, I felt my phone vibrate.

CC: Gabriel will provide the first load for you.

A grin crept on my face, betraying my confusion after rereading the text and registering what was about to happen. He’s had me service other guys from time to time but only when He was there to watch and direct, it has definitely never been His staff. I read it again to make sure I didn’t misinterpret the message before looking at Gabriel as he slid behind the wheel.

“Is He for real?” I asked, incredulous.

“Does He ever joke about this kind of stuff?”

Yes, Sir

I texted the words back with hands that trembled in nervous excitement.

I had always had a sort of crush on the handsome, kind man I had grown to know as His right-hand man, and under any other circumstances, I may have even tried to make a move on my own.

“We have a six-minute drive to the store, you better get to work,” Gabriel said while turning on the engine.

“Store?”

Gabriel didn’t answer which was slightly frustrating but not surprising, and only responded by unbuttoning the waist of his pants and sliding down the zipper before sliding the gearshift into drive.

I knew there was no choice in the matter and to be honest, I wasn’t mad at having to suck off the sexy driver. As soon as he started to press the gas to put the heavy vehicle in motion I realized my timer had started.

I undid my seat belt and reached over to feel the bulging pouch that was quickly firming under my touch. I leaned over to get my face closer and as I fished out his member from the confines of the white, straining, slightly damp cotton under his black slacks, I was pleasantly surprised. I knew he would be well endowed from the sizable package that was hard to miss in his normal attire, but I had no idea he would be uncut. I got a delightful whiff of musky, sweaty masculinity when I tucked the elastic under his full, heavy ballsack and sighed.

I looked up at him for reassurance, my hand stroking his thick shaft, only to see his eyes focused ahead on the road in front of us and turn back to the warmth radiating from his lap to get to work. He smelled delicious like man, sweat, and hints of piss and precum. I took a deep inhale of his furry bush and felt his cock throb against my face.

“Five minutes,” he said softly, letting me know there was no time for me to make pleasantries with his meat.

I pulled back the delicate foreskin around his thick, glistening head to take him into my mouth. I could taste his precum and sweat as I slid my tongue around the pulsing uncovered tip forcing out a soft moan from his plump lips.

I work the head as I find and softly pull his hairy balls, allowing for more of his musky scent to fill my nostrils and the car, driving me crazy. He lifted his hips, forcing his pants to slip slightly lower which made my job just the slightest bit easier. I swallowed him as far down as I could at that angle and intensified the attention with my hand on his nuts. He started breathing heavier as I worked his shaft with every tip and trick I had learned from servicing the man I was there to visit many times before. Gabriel had a very sizable piece but it was not as big as His. I got all the way down on him, the gear shift dug into my chest and hitting my head against the steering wheel as I bobbed up and down.

"Three minutes left, sir,” his voice choking out between stifled moans.

I let out a muffled chuckle at his formal addressing of me. Even though I was His boy and ordered to service one of His staff members, I was still to be regarded formally.

My nose was almost buried in his bush, throat muscles milking his shaft with an expert reflex as I raced against the clock. I pulled off, replacing my mouth with my hand, and stroked him fast as my face makes its way lower to start sucking on his balls and the sound of wet pumping skin mixed with his increased groans of satisfaction filled the car.

“Oh fuck! He said you’re great at that.”

“Mmmhmmm” I moaned with pride with both of his large, hairy, sweaty balls in my mouth.

I could feel them start to tighten up, pulling from my tongue, as my hand rapidly pumped his pulsing shaft that was steadily leaking.

“One minute left, and I’m just about ready,” Gabriel panted.

I switched back to his cock, following my fist with my lips, sucking and stroking, free hand tugging at his sweaty, spit-lubed sack. I am ready to swallow his load.

“You need to take it open mouth and on your face,” he gasped with urgency, giving me the final task to complete this command.

I pulled off and turned my head while continuing my hand’s rhythm, angling him to catch his splatter like the cum addicted slut I had become since I met Him.

I felt the first rope of hot spunk hit the back of my throat.

“Uh Yah!” I moaned in encouragement with an open mouth as I instinctually swallowed while keeping my mouth open and pulling my head back slightly.

The next shot landed across my lips and outstretched tongue. The car slowed down while Gabriel shook and grunted obscenities of praise until we came to an abrupt stop as more thick ropes of his tangy jizz splattered my face until my beard, nose, chin, and even forehead, were painted. He moaned and shook with his leg tense against the break. After a deep exhale he grabbed the base of his cock from my hold and swiped the cum around my reddened, sweaty, gooey face.

“Clean it up,” he said in a way that made me have to stifle a chuckle - he was following orders but he definitely was not naturally dominant like He was.

I sucked his cock back into my mouth, thoroughly cleaning between his head and foreskin and down his coated shaft. I savored the mix of his flavors as he reached under me to put the car in park. I heard the camera of his phone click and then the wooshing sound of a message being sent as I nursed the last bit of sperm from his piss slit. I knew a picture of me, face covered in jizz, lips wrapped around Gabriel’s softening meat was on its way to Him but I didn’t care, I was so turned on and proud I completed the first task, knowing there was a big smile across His perfect lips when he received the photo. I shifted back into my seat and unfolded the passenger mirror.

"Wow.. that was a lot, and thick," I said with true awe at the amount of seed glazing my face.

Gabriel folded his cock back into his pants as I admired my reflection.

“Thank you,” he said with genuine gratitude and what must have been desperate relief.

“Anytime He wants I guess…” I said with a shrug knowing that really is the only answer, “Can I get a napkin?”

Gabriel didn’t respond which was weird because he was usually so accommodating.

I was about to reach into the glove box when my phone buzzed.

CC: That’s my good boy, such a hungry cum slut

Under the message was the photo Gabriel had sent to Him and I couldn’t help the flush that rushed to my slimy cheeks. I had grown to love the salacious words He would call me as much as the sweet pet names during softer moments. I learned they were not to degrade me but to free me and teach me to take pride in my pleasures.

CC: Now go inside and let them know you are here to pick up a package for me.

I smiled as I typed my response realizing He got me a present.

Yes, Sir