The Boss of Me

This is a work of fiction; any resemblance to a person living or dead is unintentional. The stories in this series are set in the early 1990s.

* * * * * * * * * * * * * * * * * * *

My stomach churned as I drove the six blocks from my house across the main drag of Stockdale and then down Charity Lane to the house of Katelyn's family. I wasn't even this nervous before my first date with her, but oh so much had changed since then.

In a span of roughly 24 hours, I'd had a hung Black man masturbate me and feed me my own cum, then blast his own seed down my throat. Less than a day later a horse-cocked white man massaged my prostate, pressed my face into his ass for forced rimming, then showered me in cum -- all as a part of a daylong lesson on the joys of anal satisfaction.

In the two weeks since I'd started this job I'd been on a dizzying journey from inexperienced-but-curious teenager to some kind of passive-but-impressionable initiate to a secret sex club with no scruples, no inhibitions and no boundaries.

That had to be part of this runaway anxiety as I wheeled my car to a stop in Katelyn's driveway: All of this cum-soaked transformation, from the sensations on my skin to my gullet and now burned into my thoughts and taste buds, had occurred since I'd done so much as even get my last kiss from my girlfriend.

Was I still even a boyfriend? A man? Worse -- and pouring gas on the fire in my stomach -- would Katelyn see me different, smell me different, taste me different? Because God knows, the musk from Russ' balls, taint and ass was still embedded in my nostrils and the back of my throat.

My self-conscious fretting was broken by the sound of muffled yelling as I pulled in the driveway. It was definitely Katelyn's voice.

"Danny, you little prick! I'm going to fucking KILL YOU and your stupid little fuck-face friend!"

Katelyn emerged from the garage in front of me, stomping and eyes wild with rage. Her red tank top was darkened in a random splotched pattern -- apparently by something very wet.

She stopped and turned back toward the house just as her younger brother bolted out of the garage with another boy, both armed with Super Soaker squirt guns, and ran laughing across the front yard. She started after them but stopped abruptly and threw up her arms in frustration.

"Mother! Fuckers!" she shouted at no one in particular. She marched over to my car window, sputtering. Water dripped from the hair on the back of her head.

"Look at this! I can't go out like this! They completely ruined this night!"

"No, it's all right," I said, feeling immediately calmed in the knowledge that this distraction might work to my advantage.

"It's just water... I think." I touched the sopped ends of her blond hair. "Yep, just water. Take your time, dry off and change and we'll still have a nice evening. I can wait here, or come in and wait."

Katelyn stamped her foot and huffed. "Grrrrrr." I took her wrist in my left and and shook it.

"C'mon, babe. It's not like Pizza Hut takes reservations. We'll eat when we get there." I shook her arm until she made eye contact with me. She exhaled deeply and made a little smirking smile.

"You're right. It's been too long and I can't let that..." she turned her head toward the yard and shouted, "LITTLE TWAT! ruin our night. You can wait here -- I'll be out in a minute or two." With that Katelyn bounded up the driveway, through the garage door opening and into the house.

I heard cackling laughter and saw her 11-year-old brother and his buddy on the lawn. They were aiming their Super Soakers at me. I started cranking the window handle the instant I sensed their malice, and managed to get the glass most of the way up before two powerful streams plastered the car. Some water got in, but only enough to spritz the dashboard and side of my head.

Rather than get angry, I laughed and shook my head thinking about what those streams of liquid reminded me of in recent history. Then sighed.

I don't know how long I was lost in reverie before my eyes caught a flash of yellow move in the garage through my windshield. The tube top had been replaced by a tight concert T-shirt commemorating The Cure. I knew from what she'd told me that she'd attended the show with her former boyfriend -- the one she'd let slip was nicknamed "Kickstand" by his friends, causing me nonstop feelings of inferiority. And my god -- if I'd felt insecure about a theoretical monster cock, the last few weeks had made it a real, daily nightmare. Who said six inches was average?

Katelyn's back was to me as she opened the door of a refrigerator in the rear of the garage, behind her father's Coup de Ville. The light in the box flicked out as she shut the door, turned and strode toward me with purpose and maybe a dash of anger. She had a brown paper bag in her left hand.

She slid into the passenger seat and dropped the bag on the console, next to my right elbow.

"I need a mood re-arranger," she declared, and reached into the bag. She fished out a Budweiser tall-boy, cracked it open and sucked the foam of the top and then a good one-third of the can's contents in one toss of her head. Her eyes were watering when she pulled the can away from her mouth.

"Ahhhh," she sighed with a dazed smile. "Fuck those fuckers!" I was staring at her, and we both laughed as if on script. I was side-glancing her braless tits nipping out through her T-shirt when she handed me the beer.

"Drink up," she said with a laugh in her voice. "You need to fix your mood, too. I have three more in the bag." She handed me the can with her right hand and slid her left along my bare thigh.

I wasn't thinking of female nips, or rimming male ass, or even washing fucking cars as I felt the cool effervescence of the lager tingle my tongue and her lips glide up my neck toward my ear.

* * * * * * * * * * * * * * * * * * *

The quitting bell blared across the car lot. Only problem -- it wasn't quitting time. In fact, it was the opposite of quitting time -- 10 minutes before 11 a.m. on a Monday morning. Thinking it was a mistake, I pulled the trigger grip on the hose end and resumed washing cars. But the the alarm went off again. And again. And again.

I sighed, realizing since there were no customers in the lot and no impending tornadoes, the signal was clearly meant for me. I dried my hands on the chamois, laid it on the edge of the soap bucket and walked to the sales office. Standing on the other side of the plate-glass door was Russ Wilks, his bare forearms crossed over his white dress shirt and a smile creasing his face.

He held the door open and ushered me in with a sweep of his arm, then shut it behind me.

"Something up?" I asked, puzzled. "It's not lunch time." Russ chuckled as he bolted the lock and flipped the signed from "Open" to "Closed."

"You are correct, Petey," he chuckled. A big palm clapped down on my shoulder and spun me toward his office. "It's story time! I can't wait to hear about your big date on Friday night."

I sighed -- he had apparently noticed that I'd been avoiding the office since work started that morning. When I last saw Russ on Friday afternoon he'd just filled me with sex advice for my date with Katelyn... as well as a face full of hot cum.

Never mind that -- damn the old horny goat -- his instructions actually worked; I was aswirl with emotions about it. Both the new level I'd gotten to with my girlfriend, and trying to reconcile that with the ambiguity wracking me due to my crash-course in man-on-man sex.

If Russ had heard my sigh or sensed my reluctance he gave no indication. Rather, he steered me to the chair on the visitor side of his desk. He did notice my glance up over my left shoulder, at the television set in the upper corner of the room -- the one rigged with a video camera. Russ laughed.

"Don't worry, sport. Haskell's too busy to be watching TV today." I looked up and saw a glint in his eye. He shifted in his chair to get comfortable, pushed it away from his desk and leaned back. His hands were clasped over his stomach.

"Well? How did it go, son? Did you get see a new side of Katie? The BACK side?" He winked and laughed. I sighed again. I knew I wasn't going anywhere until I told the story.

"It went... good. I have to hand it to you, some of that stuff actually worked."

Russ sat up a bit and raised a hand, palm facing me. "Stop stop stop. Don't give me the Cliff Note's version, boy! Start at the beginning."

I took a deep breath and exhaled slowly. "OK. After I left her and went home to change clothes, I went down to her house to pick her up. We were going to go to Pizza Hut, drive around a bit and go to our usual spot."

"The big storage lot behind Gattler's lumber mill?" I nodded. "Shit," he laughed, "kids have been going there for generations. Half this town was conceived behind that giant pile of sawdust in the back."

"Well, you want the whole story, right?" I said a bit peevishly. He held up both hands and nodded in concession, as if to say "OK, continue."

I settled into my chair and glanced anxiously at the TV set one more time, but decided what was to be was to be. It wasn't a matter of trust anymore with Russ and Haskell -- in for a penny, in for a pound.

"Anyway, she was all jacked up when I got to her house. Her little brother and his twerpy friend had sprayed her with Super Soakers, and she was stomping around like a banshee. Which was good for me, since I was still recovering from, well, you know."

"Eating your first asshole?"

I looked at Russ. He wasn't smirking or being cocky -- just matter-of-fact.

"Yeah. That. Among other things. So anyhow, her being out of her mind turned out to be a good thing. It calmed me down and then, when she came back out in dry clothes, she'd also copped a bunch of her dad's tall boys."

"Oh! Great mood-enhancer!" Russ said.

"Right! That's what she said! She drank two by the time we got to Pizza Hut, and was starting to act pretty loosey goosey. In fact, at that point I was starting to care more about keeping her upright, because a couple of our friends were there, too, and when we went out to the parking lot they shared some of their pot with her."

"You didn't partake of the hippie lettuce?"

"No," I said. "I wanted to keep my wits. God forbid I forget any of your lessons."

I was being sarcastic but he replied with an enthusiastic "Good! And smart play to keep her conscious. I may have the morals of a goat, but I draw the line at fucking inanimate objects."

Good to know, I thought. I hadn't been aware of any Russ-imposed boundaries up to that point.

"One of my friends, Tony, was as wasted as she was and he's always got pot, so he was hitting on her and she was acting all flirty."

"Oh, fuck. Don't lose that pussy!"

"Yeah, right?" I agreed. "Anyway, I managed to get one of her friends, Debbie, into the conversation to distract Tony and steer Kate away from the herd. It wasn't hard -- she was pretty wobbly on her feet. I got her into the car, and decided to turn the air conditioning to 'low' to keep her perked up."

Russ's chair squeaked as he sat forward suddenly. "Damn! That's a pro move, son! I'm impressed! Okay, okay -- just fast forward to Gattler's. I don't need a travelogue."

I sat up, too, toward his desk. His blue eyes were drilled into mine, and it looked like his hands were fidgeting in his lap. Russ was really into this.

"Okay, once we got there I did a once-around drive-by to make sure we were alone back there. She had her hands on my crotch most of the drive back from Bryce City and my cock was pretty sore from being caged up..."

"She didn't pull it out on the drive? No road head?"

"No! Just constant rubbing. The pot had kicked in at that point and it was all I could do to keep the car between the lines while she rubbed my junk and nuzzled my neck." I looked at Russ; he was wide-eyed and nodding.

"As soon as I put the car in park and killed the lights, she practically jumped into my lap and her mouth was all over mine. I had to struggle to get my seat belt off! Her tongue was down all over the inside of my mouth, practically down my throat. I grabbed her tits with both hands and...."

"Show me."

"What?" I stammered as the movie playing in my head screeched to a halt.

"Show me," Russ said. He pushed his chair farther from his desk, leaned back and patted his thighs with both hands. I sat, dumbfounded... what did he... want me... to show... him?

"C'mon, Petey. You licked my ass and ate my cum... you can show me how Kate kisses." He slapped his thighs again, for emphasis. Guided by some autonomous force I stood from my chair and moved around Russ' desk.

"Did she straddle you, or go side-saddle?"

"What?" I was dazed.

"How was she sitting on you? Show me." I thought about it, and then positioned myself so both legs were on his right side. I sat on his lap, wrapping my right arm around his shoulders. His left hand slid up my left rig cage, around to my chest and cupped what would be a breast on a woman.

I could feel the outline of his rising cock against my left ass cheek, the bulge of his left bicep under my arm and the heat of his torso radiating out of his open shirt collar. He leaned in toward my ear, Old Spice mixed with soap and cigarettes and coffee in a heady aroma, and whispered urgently: "Show me."

Our eyes locked; neither of us was breathing. I closed my eyes and leaned in across the inches that had separated us until my lips lightly touched his. They were remarkably, surprisingly soft. I felt dizzy but fought to stay focused on what he wanted -- to repeat what Kate had done to me.

So I pulled back, wetted my lips with all the saliva my anxious mouth could produce, and plunged back in. Mouth open, just like Kate, I surrounded his lips and ran the flat of my tongue along where his top and bottom lips met, forcing them open with raw pressure, raw lust.

As I did with Kate -- apparently as any horny man would do -- his tongue leapt forward and engaged mine fervently, like two sweaty wrestlers struggling for a grip. His left hand gouged at my nipple and his right hand clapped onto the back of my head, pulling me tighter. My cock urgently pressed against my shorts; his massive meat inflated insistently against my underside.

"Mmmph! Mmmmmm!" came a deep thrumming from his core. I struggled to stay focused.... What was Kate doing at this point? My tongue gouged the roof of his mouth, and then I pulled it back and roughly chewed his upper lip. Did she feel the stubble against her teeth, as I was feeling? Was her groin on fire, like mine?

Russ brought his right hand to my chest, joining his left, and yanked his head back so quickly our parting mouths made a sloppy "pop."

"Fuck! Fuuuuuucckkk, girl," he said, eyes wild. "You fucking want it, don't you?" His left hand jammed between my thighs, around and under my balls, right to the root of my cock. His rigid fingertips stroked my taint through my jean shorts.

A series of short panting sighs came out of me and I fell back into his mouth, my lips already parted and tongue darting for purchase. Regaining a moment of lucidity, I struggled to remember what I did next with my drunk, high and horny girlfriend.

I pulled my swollen and slobbered lips off of Russ' mouth, leaving his tongue searching.

"Russ... " I huffed. "I ate her out. I did what you said,"

"What?" His eyes reopened and he focused on mine. "What did you say?

"I did what you told me to do. Don't you want me to... to... do what I did?"

"Fuck yes. Fuck yes."

"I took her to the backseat of the car. I took off her shorts... she was fucking sopping wet. I ate her out and did what you said. You know, with her asshole."

Russ nodded and took two deep breaths to gather himself. He put his hands under my armpits and lifted, steering me off his lap.

"Okay," he said. "Yeah. Okay." When I was standing his hands flew to his belt buckle, then his pants button and zipper. He kicked off his shoes and in one motion his khakis and boxers swept off his legs. His magnificent manhood sprang free, its head peeking purple from his foreskin and slicked with precum, and he threw his pants onto the floor to his right against his filing cabinet.

I stood not sure what to do next. He saw that indecision and resolved it instantly by cupping his balls and pulling them up the thick shaft of his cock.

"See that taint? Kinda like a pussy, right?" Sure enough, there was a crease of skin under his balls, running right on down to his fur-covered ass. I nodded.

"Show me how you eat pussy, lover boy. And see this?" he said, swirling a fingertip over the slicked, nickel-sized glans poking from his foreskin. "That's her clit. And I already know you know where her asshole was. Get to it."

Russ parted his legs farther and slid down in his chair so that all of his sex was available to me. He didn't have to say anything more; I slid into kneeling position, put my palms on his hairy upper thigh and pushed my face into his taint.

My cock hurt so much from being bound that my stomach was fluttering. But perhaps that feeling was simply some kind of confirmation that my latest heterosexual conquest was nothing of the sort -- maybe it was just the latest step in a larger blueprint to turn me into... what? No matter what or why, I knew who was the architect. And my tongue, mimicking what I'd done to Kate, slurped up and down the taint and then, reading hip movements and moans, finally down into the cavern of the asshole.

"Ooooohhhh fuuuu....." came the keening moan. Just like Kate. I moved my hand up the thickening shaft of his cock, feeling the veins bulging against my fingers, and swirled the pad of my thumb around his pre-jizz-soaked cockhead -- just as I had rotated that thumb with alternating pressure on Kate's clitoris.

The combination of my tongue slurping roughly over his asshole and the teasing of my thumb had Russ squirming. He slid lower in his chair to give me more access, and I used the position to slurp liberally, as wet as possible, from his pucker on up the fake vulva crease to the base of his balls. Then I set up on my knees, pulled his stiffened member to my lips and alternately tongued and sucked the sensitive tip of his penis.

"My God, Petey," he sighed, plopping a palm on the top of my head and grabbing a handful of hair. "Is this what you treated Katey to?"

"Mmmm hmmm," I said, emphasizing the "hmmmm" so the vibrations would tease his swollen glans even more. I pulled my mouth away. "And then this, from the master."

I stared up until he made eye contact. When he did, I slowly slipped the middle finger of my right hand into my mouth and coated it with saliva, then slowly lowered it into has ass crack. I knew I found the prize when his eyes widened. As he taught me, I pressed steadily until I felt the ring of muscle grip my fingertip, then summoned the memory of what I did next with Katelyn.

Shifting forward, I wrapped my lips into an "O" over Russ' glans, tugged his foreskin back lightly so I had more sensitive flesh to lick. As I sucked and lapped eagerly, I began to press my finger more firmly against his sphincter, and -- just as Katelyn had done -- his hips shifted and he met my pressure with his own.

After a long second of tension, my finger popped into his ass, up to the first knuckle. Katelyn had made a sighing, gasping sound; Russ simply grunted and bucked his hip up.

Just as I had with Katelyn, I took that as a signal to keep going and added more pressure, more finger into the rectum, all the while keeping wet pressure on the clit and the glans. My girlfriend had rewarded me with a sopping cunt; my boss rewarded me with a steady flow of sweet, sticky precum, which I eagerly lapped up.

I began stroking Russ' engorged shaft with my left hand and dove back into his perineum with my lips and tongue. His breathing grew ragged, just as Katelyn's had on Friday night, and based on the instructions he had given me himself, I began the final sequence.