CaddySack

Hello readers! Thanks for checking out my latest story. It does contain reluctance themes so if you don't like that stuff, just DON'T READ IT! But I really hope you all enjoy it. If you have any suggestions for a chapter two, feel free to leave a comment. They're always fun to read. As always, all characters are 18+ years old.

Thanks again,

Firebird68

*****

"Okay, boys. Great round." Said the tall, bearded man who I was caddying for. "Let's head to the 19th hole. Drinks are on me."

He shook hands with the rest of the men in their golf group and then turned towards me.

"Here you go, son."

He handed me a hundred-dollar bill and shook my hand.

"Thank you very much, sir." I said, thrilled at the big tip.

"Anytime," he replied. "Just take my clubs to the valet and give them this ticket. They'll know which car to put them in."

He handed me the valet ticket then headed to the bar with the rest of his friends. I tucked the bill into my pocket and lifted his golf bag onto my shoulders, heading to the valet area. I handed my ticket to the head valet attendant. He looked at it and then snapped his fingers at one of the junior attendants who took the slip and grabbed the corresponding keys before heading off to bring the car around.

"You got a lucky one this time," the head attendant said to me. "I've heard Mr. Redfield tips well."

"He certainly does," I replied. "Which is good for me. I can use all the money I can get. Tuition isn't going to be cheap next year."

"I hear you. College gets more expensive every day. Luckily, I never bothered with that stuff and now I'm making two hundred a night in tips bringing rich people their cars. It's all about connections. You gotta know who's gonna pony up when they get good service. Anyways, we'll take his clubs. Thanks, kid."

I left the bag and headed down the side of the clubhouse to the employee area. The locker room was empty. I had been the last group of the evening at the prestigious Shadow Oak country club. The valet man wasn't kidding when he said connections were everything. It was only through my father's connection with one of his employers who was a member here that I even got this gig caddying. I would come here after school and go out with one or two groups depending on how quickly they played, and then I almost always got a pretty generous tip on top of the wage I was making from the club.

I changed out of my uniform; a collared polo shirt with the course logo on the right side and khaki pants. I slipped on my street clothes and grabbed my duffel bag to leave. As I was leaving, I passed the shower room on my way and heard a noise coming from it. Curious as to who was still here, I peaked around the corner and into the shower room. In the far corner, a guy was standing with his pants around his ankles and a woman was knelt in front of him, her head moving back and forth in front of his crotch.

It wasn't hard to figure out what they were doing. They were so engaged in their antics that they didn't notice my head sticking around the corner. I turned back out of sight and smiled to myself. The man was Fabien. Fabien was a twenty something tennis instructor from Italy. This wasn't the first time he had been seen doing some "extra workouts" with his lesson takers. I pulled out my phone and opened up the camera app before slowly peaking it around the corner and snapping a few pictures of the two of them and filming a quick ten second video. I figured it would be good for a few laughs around the locker room with the other caddies this weekend.

I looked at the pictures I had taken. The woman was dressed in a pink tank top and red tennis skirt. Her long blonde hair obscured her face from this angle but it was clear she was sucking him off, especially from the video. I put my phone in my pocket and slipped out of the room and headed to my car. For my eighteenth birthday, my father had agreed to pay half for a car. I had saved up a few thousand dollars after four summers caddying and a friend of my dad's who owned a car dealership had gotten us a good deal on a second hand 2013 Chevy Silverado. It wouldn't have been my first choice and burned through a lot of gas, but it was a nice car.

I threw my bag in the backseat and climbed into the driver's seat. I began absently checking snapchats and sending streaks. I jumped when suddenly a car door opened directly to the right of mine. I looked over to the car next to mine and instantly recognized the pink tank top and bleach blonde hair. She was entering an expensive Porsche SUV crossover. As she finally turned somewhat towards me, my jaw dropped. I recognized her. She was the step-mom of a girl, Sarah Thompson, who was in my class. I was never very close friends with her but her dad was very rich and after Sarah's mother died when she was a sophomore, her father had remarried some thirty-year-old blonde woman with huge tits and a big butt named Jessica. It was pretty clear that he was in it for her looks and she was in it for his money. Anyway, Sarah didn't really like her step-mother very much. They weren't very close and she was only fourteen years older than her.

It dawned on me what this meant. I had just caught Jessica cheating on her husband. I had a few options. I could show the images to her husband and ensure she got served with some divorce papers. I could ignore the whole situation and pretend I hadn't seen it. Or I could play it to my advantage. I opened my phone to the pictures of her in the locker room and stared hungrily at her busty figure sucking off Fabien. My father had told me that you didn't get anywhere in life without taking the initiative, so I hopped out of my truck and walked around to her door. I tapped on the window of the Porsche, startling her as she looked up from her phone. She rolled down the window.

"Can I help you?" she asked.

"Yes, hello." I started. "I work for the course here."

"Oh." She replied.

She tried to hide it but I could tell from the look on her face that her level of respect for me and interest in the situation had decreased.

"I actually go to school with your step-daughter." I continued. "Sarah and I are in the same grade."

"Okay well it's nice to meet you." She said. "I have to go."

She started to roll up the window.

"Just a moment. I have something you might want to see."

I pulled out my phone and opened up to the video of her in the shower room and turned the screen toward her. She stared at it blankly for a couple seconds before her eyes flashed with shock. She turned toward me angrily.

"How did you get this?" she demanded.

"You were in the staff shower room." I answered. "I am a member of staff. Do you think your husband would be so keen to discover this?"

"No!" she snapped quickly "No. please you can't show my husband this. Please."

"Convince me."

"What do you want?" she sighed. "Money? I have a few hundred dollars cash in my wallet you can have."

"I was thinking you could show me the skills you demonstrated in this video firsthand."

"Seriously?" she asked angrily. "No way! Forget it. Not going to happen."

"Okay then," I said. "I'll just send this to you step-daughter. I have her contact in here somewhere. Maybe I have her snapchat..."

"Wait!"

She grabbed my wrist through the open window.

"Fine, I'll do it."

I smiled to myself, internally ecstatic.

"Follow me, Mrs. Thompson." I said.

I walked back to my truck and climbed in the driver's seat. Reaching down to the side of the chair, I pressed the switch that controlled the position of the seat and the electric motor slowly moved it backwards until it was in the farthest back position. Jessica appeared next to the open driver's door and looked up at me.

"Get in." I instructed her.

She sighed and went to go to the passenger side.

"No." I said, and she stopped. "Get in."

I pointed to the space in front of my seat.

She gaped at me.

"You have got to be joking me right now." She said, exasperated.

"I'm not. Now get in." I replied.

I moved me left leg to the side so she had room to crawl up into the cab on her knees in front of my seat. It was a tight fit but her petite, busty frame fit perfectly with her head directly in front of my lap. I shifted my leg back in and shut the door, closing us in.

"You do the honors." I instructed.

She glared up at me but seconds later, her perfectly manicured nails were unbuttoning and unzipping my cargo shorts. Her small hand reached in and pulled my semi-erect dick through the hole in my boxers.

"Get to work." I said. "And make it good. Your spot in the will depends on it."

With one last glare, she leaned her head down and engulfed my hardening member in her plush, red lips. She ran her tongue along the head of my cock and began applying a light sucking pressure. I sighed in pleasure and gripped the steering wheel, enjoying the feel of her mouth on me. Soon I was at full staff and throbbing under her ministrations. I turned the key in the ignition, starting the truck and lightly pushed her left foot and leg out of the way so I could access the pedals. Shifting into reverse, I pulled out and began to leave the country club. Jessica stopped sucking and looked up at me confused.

"Where the hell are we going?" she complained.

"Did I tell you to stop?" I demanded. "Get back to it now, or else."

She whined and gave me her best evil eye but it just made her look even sexier as she returned to my rod. I began the slow drive home which was a good twenty-five minutes away, and longer if I took the backroads, which I was going to. I wanted this to last. Meanwhile, Jessica had begun a slight bobbing motion, sucking the head and first bit of my shaft in and then going back up. Her tongue massaged the underside of my shaft while her lips maintained their tight seal. She began slowly taking a bit more at a time, her lips sliding further down and leaving more of my member covered in saliva.

She got a few inches of my nine inches down before the tip hit the back of her mouth, triggering her gag reflex. She bobbed a few times, hitting the tip of my penis into the entrance to her throat before pulling off and taking a break.

"Nobody said stop." I called down at her. "Get your mouth of that dick. Now!"

Jessica coughed once more before resealing her lips around my steel rod and continuing to move up and down a few inches. I was eager to hear her gagging on my length again so I reached down with my left hand and grabbed her head and began forcing her down. I hit her gag reflex again and continued pushing as she began choking but I almost drifted off the road trying to focus on the two tasks and had to let go and correct my truck back between the lines. Jessica backed off my dick, breathing hard and coughed. I glanced down at her. Her eyes were watering and there was a string of saliva connecting her lower lip to my penis.

"Stroke it." I instructed.

She swallowed and obeyed. Her soft right hand gripped my shaft and started stroking up and down. The saliva made for a great lubricant and it felt excellent having her small, smooth grip jerking my cock. The sound filled the otherwise fairly silent truck. She placed her lips around the head of my penis and began sucking on it while her hand stroked smoothly and evenly. I was still eager to delve deeper into her mouth but I couldn't think of a way to grip her head and keep from crashing.

As we pulled up to a stop sign, I had a chance to think and an idea came to mind. Accelerating away from the stop, I reached down with my left hand to the side of my seat and found the button to control the distance of my seat. I pressed the forward button. Jessica let out a startled sound as my seat began moving towards her, slowly driving my head further past her lips. She tried to back her head off my crotch but the back of her head backed up into the bottom of the dashboard beneath the steering wheel, stopping her movement. She began to whine as my cock continued forward, boring into her throat and ripping sweet coughs and gags from her. She had no room to move her head and was forced to just stay there as her throat was slowly filled by my girth. I let go of the button when I felt her lips and nose press into my crotch and navel. I could feel her attempting to get her arms up past my thighs to push off of me, but there was simply no space. She was crushed in there nice and snug and there was no movement, just my cock bulging her throat.

Every glorious gag and choke was heaven to me. It felt like a wonderful massage along my entire length. Her convulsing throat involuntarily attempting to milk my cock. Life wasn't so good for Jennifer. She was wriggling and squirming in an attempt to dislodge to nine inches of thick steel rod from her tight, tight throat. She only managed to get labored breaths in through her nose when she was able to move it off from where it was crushed against my crotch.

As we came to a red light, I leaned back in my seat to take a look at my little fuck toy. Her face was red and flushed and her eyes were squinted and watering as they silently pleaded up at me to release her from the compromising position. I stroked her bleach blonde hair and moaned as her throat twitched once more, sending electric spikes of pleasure through me. I didn't even notice the green light until someone behind me honked and I quickly returned my eyes to the road.

I could feel my load coming. I had only had a few blowjobs from the few and short-lived girlfriends I had had. And none of them even came close to this. I held on for a few more seconds but I knew I was about to blow. Jessica felt my cock swell in her throat and let out a muffled shriek around my base. That sudden vibration instantly set me off and my load simply erupted down her throat. There was no better word for it. Mammoth streams of hot spunk flooded her esophagus and she had no choice but to try to swallow what she could. Most of the thick cream went straight into her stomach but some of it backed up and spewed from her nostrils.

After I had unloaded about a gallon of cum into my little cum bucket, my orgasm was finally finished and I felt my rod begin to soften slowly. Jessica tried to move her head to the side and slide my spent cock out of her poor throat, but I clamped my thighs together firmly keeping her still stuck on me. I took a deep breath and looked at my surroundings. It was amazing to me that I hadn't crashed during all that. I realized that I was however doing about twenty five miles an hour in a forty five zone and was glad that I had taken the back roads and there was no one behind me any longer. Jessica whined and choked on my soft member that was still lodged in her windpipe and continued to draw labored air through her now cum-filled nostrils.

Despite having just blown the biggest load of my existence, I felt my cock twitch as the feelings and it began to grow again. I could see outside I was almost halfway home so I knew I still had plenty of time to enjoy Mrs. Thompson's sweet hole. She let out a muffled cry as she felt my cock reverse it change size and start growing once again, stretching out and bulging her neck once more. She squirmed and struggled to get free but I still had a good twenty minutes and I wasn't about to let my cock-sleeve go.

The ride resumed its earlier routine of me keeping the truck on the road and Jessica reluctantly milking my balls. I was hard as steel again and she was feeling every inch in her tight little throat, but this time I could relax and just enjoy it with the edge taken off from my first load. I leaned back into my chair and settled into my cock-holster for the remainder of the ride. When I eventually pulled into my parents' driveway, I still hadn't cum. I knew I wasn't too far off it, but I wasn't close enough for my comfort, being parked outside the house where my mom and dad were. I shut off the truck and pressed the button, slowly moving my seat back and removing my rigid shaft from its cozy home in Jessica. As it left her mouth, strings of saliva and cum tracking back to her pretty lips, she dropped her head and coughed, recovering from the fierce abuse of her esophagus.

"Get out, Jessica." I said, opening the car door and moving my left leg giving her space to exit.

She weakly climbed out and leaned against my truck drawing in ragged breaths. I stepped out next to her and took her arm, pulling her to the rear of the vehicle. I dropped the tailgate and lifted her up onto the bed, pushing her onto her back and spinning her around until she was upside down and her head was hanging off the edge of the tailgate. Before she could react, I had lined my slick cock-head up with her lips and slammed into her mouth until she was kissing my balls again. My shaft had lost a little bit of its hardness during the transition, but a couple times hilting myself in her tight hole quickly restored any lost rigidity.

Jessica's arms pushed at my chest and torso in weak attempts to push me away, but I easily grabbed her wrists and pinned them to the bed without interrupting my thrusting. I hammered back and forth, mesmerized by the sight of her throat bulging and expanding to an absurd amount every time my hips went forward. Each down-thrust ripped gag after gag from her sweet mouth. My balls slapped into her nose and forehead making a slight noise. I fucked away at her face for a few minutes before the familiar sensation built to a peak and my balls tightened, ready to deliver their payload. I rammed in once more time, bottoming out in her throat and released the floodgates.

This was my second orgasm of the night but it wasn't any bit lacking. I powered shot after shot of hot jizz straight down her throat and into her stomach. I released Jessica's wrists and grabbed her huge breasts, groping them and further fueling my peak. She simply laid there, too exhausted to fight it and just struggled to keep the torrent of cum down. Her efforts failed however and the flood of cream backed up her windpipe and leaked past her taut lips and dripped down onto her face. My orgasm finished and I came down as the last of my jizz seeped into her esophagus. Before my cock could begin softening, I pulled out my phone and snapped a few POV photos of Jessica's body splayed out before me, throat bulging and lips pressed to my crotch.

I slowly pulled back and watched as her neck returned to its original shape. Jessica rolled onto her stomach and choked and coughed up bits of cum onto the pavement below. I tucked my soft penis into my pants and went to get my bag from the backseat of my truck. When I returned, Mrs. Thompson had climbed off the bed of my truck and was bent over the tailgate breathing hard and occasionally coughing.

"Well," I said, contentedly. "That was great. Best drive home I've had."

"Whatever." Jessica replied, her voice a bit hoarse. "Are we done?"

"For now." I answered. "But if I were you, I'd keep my schedule fairly clear. And I would remember this address. You'll be here again."

"But you said..." she started

"Shut it." I interrupted. "I didn't say anything. If you weren't a cheating slut, you wouldn't be here in the first place. Now you can go home to your loving husband. Just make sure you wash all the cum off your face and brush your teeth."

"How am I supposed to get home?" she demanded.

"I don't know. Call an Uber." I suggested. "You can charge it to your husband's card. I'll see you soon."

I turned toward the house and started up the driveway leaving her standing there in shock. I threw my bag on my desk chair and fell onto my bed. A few minutes later, I was drifting off to sleep with a smile on my face.