Taming the Asshole Ch. 1

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Man joins swapping couple on Halloween.
5.5k words
4.28
93.2k
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Part 1 of the 2 part series

Updated 09/22/2022
Created 03/04/2002
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I hated Halloween. I hated dressing up to go to parties. The costumes were always lame and quickly thrown together. Personally, I thought Halloween was just another excuse for people to get drunk. Nothing good has ever happened to me on Halloween. In fact, I usually got into some kind of trouble. When I was a kid, I would invariably end up with a bloodied nose after a fight with the neighborhood bullies trying to steal my candy. A couple of years ago, while driving home from a Halloween party, the police pulled me over and I received a major speeding ticket. That one cost me a pretty penny. Since then, I have avoided Halloween like the plague, usually hiding at home watching television, and jacking off.

Why I let Lynn talk me into going to a Halloween party this year was beyond me. Deep down I knew it was because she had been flirting heavily with me since breaking up with her boyfriend. She was dropping serious hints that she was interested in taking our friendly relationship to a new level.She owns me big time. I completed my authentic golfing outfit with a Scottish tartan wool watch cap and headed out the door. I pulled out of the parking garage and headed off to the party.It was definitely blowjob time.

"Wow! I like your costume," Lynn said when she met me just inside the door at the party.

She gave me a rather timid hug and a light peck on the cheek. Her long blond hair was pulled back into a ponytail, which danged out behind the stylish cowboy hat she wore. She was tall for a woman. I barely had to tilt my head to look down into her hazel colored eyes. One of the things I liked about her was her athletic build. I would have to ask her if she had played any sports in college or high school.

She had chosen to dress as a cowgirl. Cut-off denim shorts hugged her hips and ass tightly. She had tied off her white button-down shirt just above her belly button and left enough buttons undone to show off her ample cleavage. I could not help but glance a bit too long at her impressive rack. She caught me eyeing her cleavage and blushed.Mmm, I can't wait to get a look at those titties.

"I'm happy you decided to come. I know you hate these kind of parties, but I promise you'll have fun this time."

"You know you own me, right?" I said, dragging my eyes back up to her face. She giggled and grabbed my hand, leading me off to get a drink.

Thirty minutes later, I weakly leaned back against the deck railing, reveling in the exquisite pleasure pulsing through my cock as Lynn practically bathed it with her saliva. She was kneeling on one of the padded cushions from a deck chair. She had discarded her cowboy hat after I had unbuttoned her blouse and started kissing and licking her cleavage. As soon as I had started pulling on her bra and trying to untie her shirt, she had pulled back and slid to her knees.

I was not about to complain as her mouth was pounding up and down on my cock at a perfect pace.Oh God, she's done this before for sure. I could not remember the last time I had felt such great pleasure from a blowjob. Without the cowboy hat, she was even more beautiful. I could hardly believe my luck.

She lightly rested her small hands on the front of my thighs as I slid my hand behind her head and lightly gripped her ponytail, watching her full lips traveling up and down my slick cock. Seeing her lips wrapped so tight around my cock brought a groan from deep in my chest and my eyes briefly fluttered shut as a twinge of pleasure shot through my body. Occasionally, she would look up to watch my face, her mouth not missing a stroke, her eyes big as they stared deeply into my eyes.

I gripped her ponytail in a tight fist and clenched my ass muscles tight. I began forcing her head up and down faster and harder, forcing her to take me a bit deeper as I felt the beginnings of my orgasm approach. Her nostrils flared as she breathed deeply through her nose with each upstroke. I panted louder when I felt my balls tighten up and my cock begin to swell to new proportions.

"Oh yeah, Lynn. That's so perfect. God, you're sucking my cock so good. I'm gonna shoot my cum right down your throat. Is that what you want? Or should I jack it off all over your face?" I asked, causing her to moan around my throbbing prick. I think the naughty words aroused her even more.

I opened my eyes again, not wanting to miss a second of her sucking my cock, and was shocked to see a man and woman standing behind Lynn, watching her suck me. Immersed in the blowjob, I had not heard them come out on the deck. He was dressed as a Viking, complete with fur vest, horns on his helmet, and a sword strapped at his side. I am tall for a man and on the hefty side, but this dude was huge. He easily towered over me and had at least 50 pounds on me, all of it muscle. Various tattoos adorned his muscled arms. The only thing out of place with his Viking attire was his black hair. I had always pictured Vikings as being blond and blue-eyed.

Holding onto his heavily muscled bicep was a woman clad as a medieval bar wench. Her worn dress looked rough and authentic. The low cut white shirt she wore hugged her tits and left her shoulders and upper chest bare. The suspenders of her dress pressed around the sides of her breasts, letting her nipples show clearly through the thin white shirt.

She immediately reminded me of a younger, slimmer, less busty Raquel Welch. Her short, auburn hair, what little bit of it showed from under her white, frilly maid's hat, was ragged and uncombed. She stood submissively at his side with her eyes averted and her hands resting lightly around his arm.

A Viking and his Wench, how quaint. I quickly tried to absorb the situation and not let Lynn know strangers were watching us. I looked back down at her mouth plunging up and down on my cock and forced my hand to keep a steady pace, guiding her head just right.Oh God, almost there. I was so close to cumming and nothing was going to stop me at this point, especially some dude dressed up like a Viking.

"Looks like she sucks a mean cock," said a deep gruff voice.

Lynn's eyes shot open in shock. I stared down at her dumbfounded as she moved her eyes up to look at me questioningly, her lips still stretched around the shaft of my cock. Instinctively she tried to pull her head back to look around for the source of the mysterious voice, but I held her in place. My other hand came up to hold her head, desperate to prevent the inevitable termination of the blowjob. Anger flared in Lynn's eyes when she realized my intent. Her fingernails dug sharply into my thighs as she pushed back with all her strength. I winced in pain when her teeth began to drag along the soft skin of my penis. Relenting, I let go of her head.Fuck!

"Fucking asshole bastard!" she growled, as she sprang to her feet, wiping the back of her hand across her reddened lips.

With a glare, she turned on her heel and marched past the Viking and his Wench. Halfway to the house she stopped and turned. She started towards me, stomping loudly as she started buttoning her blouse. Stopping next to the deck chair, she quietly finished buttoning her blouse. Neither I, nor the Viking and Wench said a word as she gave each of us a withering look. Her cheeks were flushed deep red and she was quivering in anger.

"Lynn..." I said raising my arms in a surrendering motion.

"Fuck off!" she spat as she reached down and snatched up her hat. "Don't ever call me again," she said as she turned and marched back into the house.

I stood there in total disbelief at the sudden turn of events. This Halloween had actually been promising and now this happened. My eyes slowly left Lynn's departing figure and traveled back to the Viking and his Wench. His face held a blank look. I saw a small smile flick across the lips of the Wench before quickly disappearing.Who the hell is this asshole? Anger surged through me as I reached down to tuck my aching prick back into my pants, standing up fully to address him.

"What the fuck, man! Why in the hell did you do that? Are you a moron or something? Christ!" I yelled.

"Whoa, buddy," replied the Viking, raising his hands in a calming motion. "If you didn't want an audience you should have gone some place private."

"You couldn't have waited like two frickin seconds until I came?" I asked in exasperation as I zipped up my pants.

"Mmm, I suppose we could have," he said with a calmness that was rapidly making me livid.

"You're a--" I could not continue, I was so choked with anger.

Before he could respond, the Wench quickly stood up on her tiptoes and whispered something into his ear. He listened intently until she finished and then looked down into her face, thinking. Her face was tense with anticipation. It was obvious she had either asked him for something or suggested something and was awaiting his answer.

"You're sure?" he asked her with surprising tenderness. She quickly nodded, smiling gleefully. He patted one of her hands gently before looking back at me.

He cleared his throat and said, "Look, buddy, I'm sorry we screwed things up for ya there, but I, uh," he looked back down at the Wench before continuing, "have a little proposition for you."

My anger quickly faded. I raised an eyebrow questioningly, not sure about this turn of events. He paused a second, apparently not quite sure how to proceed. He nodded once to himself and then addressed me again.

"We want to make it up to you. So I'm gonna just give this to you straight. My pet here wants to play. And since she's been such a good little wench lately, I'm allowing her to pick her playmate tonight. She has picked you. What do ya say?"

"Wh-What do you mean?" I asked suspiciously.

"I mean she wants to play with you dude. As in fuck you."

I just stared at him for a few seconds, dumbfounded and confused.Is this guy serious? He was offering me his girlfriend or wife or whatever she was to him. The serious look on his face told me he was not pulling my leg. My cock had finally deflated, but my balls were still aching with need. At this point, I would do just about anything. My gaze moved from the Viking to the Wench and I admired her sensual curves. She had a gorgeous body and something about the way her eyes looked into mine cemented the deal.

Turning back to the Viking, I said, "You mean just her and me, not you? I don't go for that gay shit. Sorry, no offense intended."

He chuckled. "Yeah, just you and her. Trust me, I don't go that way either."

I did not have to think long. "Ok, so uhmm, well, how are we gonna do this? We just gonna do it here or what?"

"You know that Motel 8 on Route 28, just south of town?"

I thought a second and said, "Yeah, I know it."

"Meet us there in an hour. Just come into the room. Room 15," he stated as he tossed me a key ring with a key and a metal tab attached to it. The tab said "Motel 8" on it. I looked up to say something else to him, but they had already turned and were entering the house.I guess he's not much for chitchat. The motel was 20 to 30 minutes away, so I had a good half hour to kill.

I went back into the house and grabbed a beer from the bar. I nervously wandered the house, avoiding people. I was not in the mood to mingle. The last thing I wanted to do at this point was to chitchat with some boring asshole dressed up as a pirate. I took a complete tour of the house, keeping an eye out for Lynn. She had obviously stormed out of the party and was not coming back. There was no way I could go over to her house and try to make up. She would see through me in a second.Oh well, fuck her if she can't take a joke.

Checking my watch, I knew it was time to go. I pounded my beer, dumped the empty bottle into a trashcan, and went to my car without saying goodbye to anyone. I sat there for ten minutes unable to get up the nerve to start the car.Could they have been serious? Finally, I told myself to quit being a pussy and started the car. I gunned it out onto the highway, knowing I was going to be late. I parked behind the hotel after finding a secluded spot not lit up by the towering overhead parking lot lights. Wishing I had brought another beer from the party, I got out of the car and went into the hotel.

I walked slowly into their dimly lit room, feeling awkward and out of place.Man, this is weird. My jaw fell open when I saw the two naked figures on the bed. Stretched out on her back was the woman, Wench, her head propped up on several pillows. The soles of her feet were planted flat on the bed and her heels pressed up against her ass, her knees spread open insanely wide, lewdly displaying herself to the Viking.

Between her spread thighs on his belly was the Viking, his face mere inches from her completely shaved womanhood. Her pussy was almost babyish in appearance, so completely hairless and puffy looking. The Viking was gazing in fascination at her fingers as they moved in quick, practiced circles around her hard, wet clitoris. Her face wore a mask of pure pleasure; eyes squeezed tightly shut and mouth agape. Her hair, now cleaned and combed, framed her face perfectly. Her small pointy nipples, stood up proudly as if on display just for us.

Hesitantly, I sat in a chair near the bed, feeling embarrassed and unsure. The room was hot and smelled of sweat combined with raw sex. My face flushed hotly. Neither one had noticed my entrance.Well, what the hell am I supposed to do now?

The Viking took two thick fingers and inched them inside her horny, gaping hole. She whimpered as he ground the edge his fingers back and forth across the bottom of her opening, thrusting them upward to probe her deep wetness. The Wench pushed her head back into the soft pillows, thrusting her hips up into his probing fingers, obviously wanting him to penetrate even deeper into her ravenous cunt. Her spare hand was pulling and pinching her left nipple with unabashed enthusiasm. I watched as her slim hips began to shake and her fingers became a blur over her bare mound.

The Viking's fingers began assaulting her hole faster and harder, his fingers sawing in and out at a feverish pace as the wet sucking sounds from her pussy filled the room. The look of concentration on her face was quickly fading into one of pure, unashamed bliss and I had a feeling she was about to explode in a massive orgasm. My cock felt thick and stiff in my pants.

Suddenly, the Viking stopped his vigorously plunging fingers. He roughly grabbed her hand and forced her fingers away from her red, engorged clitoris. I could actually feel her audible groan of disappointment from across the room. Her head shot up from the pillow, looking down at him in genuine frustration, her eyes silently pleading him to let her continue.Holy shit, he's cruel.

"Not yet, my naughty little wench!" said the Viking sternly. "You're gonna please me first!"

The Viking crawled up toward the headboard and leaned back against it. Spreading his large thighs wide, he pulled her by the hair toward his massive pole.Fuckin' A! He's hung like a damn mule. Seeing him nude, I could see that he was very muscular and hairless, except for the tuft of trimmed hair above his massive stalk. Additional tattoos adorned his thick muscular chest.

With a whimper of disappointment, she allowed him to pull her up between his thighs, where she knelt and lowered her face to his manhood. I had a hard time believing he was that big. His cock stood straight up toward his belly button. It was incredibly fat and bloated. Thick, ropey veins meandered up the shaft to the purplish colored mushroom head. His large, egg shaped balls hung low in his soft scrotum. Taking a quick guess, I would have said he had to be at least 9 or 10 inches in length.No way she takes that whole thing in her mouth.

Her hand closed around him forcefully, gripping the base and pulling the skin taut. The tips of her fingers did not even meet around his fat shaft. Her mouth descended to the head of his cock. Without a pause, she sucked it into her hot mouth and pushed her mouth downward. Her lips stretched wide and her eyes closed in concentration. I could see her cheeks sucking inward as she tried to get his pulsing prick deep into her throat. Amazingly, her lips slid almost to the very base of his prick.Fuck me, she did it!

She paused briefly at the very bottom, her hand keeping a very firm grip on the base of his cock. As her mouth slid back up his pole, I heard her draw in a lung-full of air through her nose. Her hand and mouth quickly merged into a rhythm of up and down movements making the Viking groan and pull her hair harder, forcing her up and down faster.

I stared at her wet lips moving up and down on his impressive root. It was extremely shiny with her saliva. I noticed her ass pushed way up in the air. From the angle of my chair, I could see her wet pussy and asshole between her spread cheeks. Thin shiny rivers of her juices were sliding down the insides of her thighs. I reached down and gripped my cock through my pants, giving it a squeeze as I imagined my cock sliding into her from behind. As if reading my thoughts, she turned her head and looked back at me, while shaking her ass. Signaling with her eyes, she looked at my crotch and then toward her wiggling butt. I knew that was my cue.Finally.

I slid out of the chair and knelt at the edge of the bed. My face was level with her spread-open twat. I licked my lips and leaned in, smelling her hot, wet, musky female juices. I pressed my lips against her puffy cunt lips.God, yes. I felt her juices totally coat my lips and chin. She was so incredibly wet and slick. Her skin was so soft and wet that my lips were gliding over her labia without any friction. I extended my tongue, flicking at her lips and clit, feeling her ass squirm, pressing back into my mouth. I flicked faster and harder at her clit and heard her moan around the Viking's cock. The Viking began grunting with each thrust of her mouth down his erection.

Wanting to make her cum with him, I extended my tongue, making it into a hard piece of wet tongue-flesh. I began pushing my face back and forth into her, my tongue pounding in and out of her horny fuckhole. She quickly established a rhythm with me, pushing her ass back at me as I thrust my tongue forward into her gripping pussy. My nose banged into her slit with each thrust and my face quickly became drenched with her copious juices.

She growled deep in her throat as the Viking gripped her hair in his big fist and began madly pushing her sucking mouth down on his prick. I could tell he was close to spurting a huge load into her. I wet a finger with her juices and inched it deep into her ass. She screamed hysterically around his cock and her body quivered uncontrollably.

The Viking laid his head back, his facial features softening as his orgasm began overtaking him. "Oh, dear God! That's it! Take it-- Take it all! Yesssss!"

He let out a deep, long moan and I could tell he was spurting load after load of hot cum deep into her throat. His massive cock muffled her squeal as she ground her hungry twat into my mouth as hard as she could. I thrust my tongue inside of her as deeply as I could and wiggled it fiercely. Her wet cum exploded as her pussy muscles contracted around my tongue, milking it. I licked and sucked her cum as fast as I could, trying to keep up with her overflowing juices.Holy shit, she cums a lot.

I slowly pulled my finger out of her ass as they both sagged into a quivering mass on the bed. The Viking disengaged from the Wench and rolled to the other side of the bed. He breathed deeply and closed his eyes, obviously enjoying the warm afterglow from his massive orgasm. The Wench looked back at me and grinned brightly when she saw her juices smeared and dripping from my face.

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