Shag Story
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  • Added : June 10, 2020
  • Words : 2267
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An Introduction

By Cal

I’d gotten there much earlier than we’d planned, I’m anxious like that. I fidgeted in my seat for what seemed an inordinate number of minutes and wondered if I’d been stood up before ordering my second Old Fashioned when Erica walked in with Dean, and boy was I smitten. Like jaw-hit-the-table and tongue-went-lolling-about smitten.

She was forever trying to hook me up whenever we weren’t together, which was on, off and some other times in-between as well. We indulged each other’s fantasies while at the same time managing to not fall in love with each other. If there was ever a relationship of convenience this was it. I hadn’t seen her much the last few weeks, but she’d texted saying there was someone she’d been dating that I had to meet, and so here I was.

Dean was a rugged kind of handsome, crew cut up-top and a stubbly beard covering a rigid jaw line with an easy smile. He was in the construction business and looked the part too, wide shoulders and well-defined pectorals under his v-neck, tapering down to a slim waist, and sturdy legs in narrow jeans ending in handmade cowboy boots.

It was with Erica that we had determined I might be at least bicurious, but we’d never really done much but talk about it, and then proceeded to critique a dozen MMF pornos she pulled up on her iPad before fucking wildly with fantasies flashing in my tightly scrunched eyes.

Having been a former hostess at the jazz club, Erica was able to get us a pretty private spot in the back, where the music was just loud enough that you could still conduct a private conversation. After a strong handshake, Dean slid into the horseshoe-shaped booth, sitting in the middle with Erica and I on either side.

We made small talk as the lights dimmed and the band started up with some Dave Brubeck and sprinkling in some Wynton Marsalis for good measure. I must’ve been gawking a bit too obviously at Dean because Erica decided to tease me.

“Oh just blow him already!” she laughed.

Embarrassed, I chuckled too and looked away, but not before we made eye contact. His eyes appeared to be twinkling, either from interest or bourbon, or both. She’d told me stories about him being dominant, and how he was slowly initiating her into a world of D/S relationships starting with the dungeon he’d built from scratch. For the first time that evening I sensed the undertone.

My experience of BDSM was limited to what I’d read in erotica here and there, and the fur-lined handcuffs, blindfold, and flogger from a set of naughty toys she’d picked up on a whim. Invariably though the conversation turned to sex soon enough. Dean asked where I lay on the sexuality spectrum. Even though I wanted to answer wherever he wanted me to, I maintained decorum and replied somewhat demurely.

“I really don’t know. Can’t say I’ve experienced anything beyond heater sex.”

“That’s okay,” he replied. “There’s always a first time for everything. Like now.”

I almost physically had to shake my head to make sure I’d heard him clearly. If the light was any brighter, he’d have noticed me blushing. I looked over at Erica to see if she’d heard what he said, and oh what the hell they were making out now.

He broke away from their kiss and put his hand on my left knee. I shuddered, just like I had when we shook hands. Dean was the embodiment of power and control. There was something in his voice, his touch, his entire being that made you turn to quivering jelly in the most submissive way possible.

Like a snowman melting into the ground in the sunlight I slowly shrunk down under the table. Would anyone see? Did I even care? Nope. That was the effect Dean had on me.

His jeans were starting to tent with his erection as I reached for the zipper and pulled it down. The magnificent member inside stood erect at a 45-degree angle and pointed even further upward as he scooted lower in the seat to give me access.

In the low light his log-like penis twitched and beckoned to me. With no hesitation I wrapped my fingers around it. I pulled down the foreskin and licked the sticky head. Fueled by pure lust I gobbled the tip of his knob, slobbering all over it. I was thirsty for him, no doubt.

I let my lips slide down the shaft, swallowing every bit of it until my eyes burned and chest heaved for air, but still there was more of it. With a grunt I exhaled, and came back up, before going down again, trying to gain new ground and appreciating the girth that strained my untrained jaws. I waggled my mouth trying to inhale as much of it down my throat as I could and that started him bucking in his seat as my head banged on the underside of the table. His stout fingers went in my hair, grabbing my short curly locks as I continued to suck on him but with my tongue stuck out and rubbing against the underside of his rod, a trick I’d remembered from a previous girlfriend.

In a pause between songs I panicked as I heard the waitress ask if anyone wanted another drink. Dean’s hand remained where it was clamped, holding my head between his legs as he ordered another round for the table. And then the drums started up once again and back I went to my oral duties. Blowing a real, live dick was quite a different experience from Erica’s strap-on and a treat in itself.

I brought my hand up from my lap where I was stroking myself to caress his hanging scrotum and that seemed to rev things up a gear or two as his cock lurched in my mouth and his fingers tensed and then yanked hard. Like a good little slut I swallowed as he spurted in my mouth, a couple of smaller squirts and then a thick gush that coated the inside of my throat. I stayed in position for a few more beats before I swirled my tongue up and around it, getting every last bit of it I could.

Slowly I crawled back up to my seat and looked around guiltily, a cheeky smile playing on my lips as Erica looked at me and laughed. She leaned across him and grabbed me by the shirt and proceeded to kiss me deeply and quite brazenly.

“Shall we take this party back to my place?” Dean asked, looking right at me.

“Yes Sir,” I blurted out without a second thought.
We piled out the exit in the back of the club to the lot where Dean was parked. Erica and I walked arm-in-arm, reverentially a couple of steps behind him. He stopped and then kissed her forcefully, grabbing her by the ponytail, his other hand reaching down between her legs. Her fingers were like talons on his back, holding on for dear life. He pushed her face down against the side of a car, kicked her feet apart and lifted her dress. Erica moaned, palms flat on the parked vehicle as he leaned into her and kissed her neck. I watched, mesmerized, at this show of dominance. Dean looked over at me, and with a tilt of his head, indicated me over. He reached out and caressed the side of my face, and then pulled me closer.

His breath tasted like everything I’d imagined… whiskey, leather, musk. Dean kissed me, hard. His tongue was demanding, as our teeth clashed and lips ground against each other. With one hand playing between Erica’s legs, he used the other to hold me in a kiss I wished would never end. Finally, I came back to earth and feeling emboldened, I bent down to his waist. His wide leather belt had the cliched big buckle that I pulled apart. Sliding the rawhide over, I worked the button and loosened the waistband. For the second time that evening I slid down the hefty metal zipper. He was already as hard as an I-beam as I maneuvered it out of his Jockeys.

Dean guided my head down and as I prepared myself to suck him again, he pushed me instead towards Erica’s spread thighs. He yanked the gusset of her panties aside roughly, causing her to yelp and I leaned into her, inhaling her arousal and dipping my tongue into her dripping honeypot. She moaned aloud as I buried my mouth in her wetness, and she bounced up and down, riding my face. This was oral I was more familiar with and settled in happily, lapping away at her. But it was barely a minute before I felt his foot nudging me as I knelt there, and knew my turn was over.

He stepped forward and slowly slid into her, and by the time his pole was fully inside her, she was on her tiptoes despite her high wedges. He started to pump, causing her to gasp incoherently as he backed out and then impaled her repeatedly. I stayed on my knees, barely inches away, transfixed again by the raw power Dean exuded. The squelching of their sex and slapping of skin on skin were the only sounds I heard, their profiles blending into the shadows of the dimly lit parking lot.

She was close, I knew the signs. First her fingernails started scratching the top of the car, then she began her low humming moan which was accompanied by her shaking uncontrollably, this was going to be a good one. He released her hips and reached up and around her breasts, squeezing hard. She squealed so loudly he brought one paw around her mouth before crushing her tit again. That was all it took, his palm muffling her screams as she went into an orgasmic paroxysm, thumping against the parked car while his stout body pinned her rigidly against it.

“Shhh… shhh… there’s a good girl… yes, you were wonderful my darling… shh now, take a deep breath for me, yes, like that.” His voice was soothing and she relaxed, body slumping limply against what I only just noticed was a white Escalade.

He pulled out of her, and to my amazement, his member remained as erect as when he’d started. Seeing my slack-jawed expression at his monster cock shiny with their juices, Dean added “I saved this one for you too, pet.”

The hairs on my arms stood up and a shiver ran down my back. I had never been called that before, but somehow, it felt just right. After making sure Erica was alright to stand on her own, he helped me up and stood me next to her, in a similar pose.

I sensed his hot breath on the back of my neck. Then he took my earlobe in his mouth and I was turning into a pile of putty right where I stood. He reached around and undid my belt, then my slacks and pulled them down, along with my very sensible boyshorts. A demanding hand went around my clenched buttocks, his coarse palm claiming them for his exclusive use.

He whispered in my ear, “Do you want this?” and all I could do was lean back against him and sigh my approval.

Using his calloused finger he touched my tip, dripping with pre-cum, and he rubbed it all over the head, then gently stroking the length. It took a supreme effort of willpower to not spray my load on the car right there and then, but I squeezed my eyes and persevered. I felt him poking against my exposed bum, and with both hands, I spread my cheeks for him. Quickly he slipped on a lubricated condom, and then had to bend at the knees to account for my shorter height, but then there it was. Dean’s magnificent penis pushing against me, at me, in me, into me. My almost-virgin ring that had only ever experienced Erica’s strap-ons, was getting gently, firmly, hungrily impaled.

My breath caught in my throat at the exquisiteness of that moment. He stopped a couple of inches in to let me adjust myself, before I pushed back against him. His dick surged forward, the wider base opening me up. Again he paused, patiently.

The only sounds I was capable of were small grunts as we started to rock together in unison. His balls were slapping against my thighs as my greedy ass swallowed him up. The clenching and releasing was getting to him, and Dean leaned forward and bit me on the shoulder, sinking his teeth as deep into the skin as his shaft was inside me.

I looked down to find Erica sucking on me, a hand cupping my sack and the other encircling my rod. Her tongue swished up and down as her cheeks hollowed out, and oh sweet mercy I was in sheer heaven.

Derek finally let go of his bite, threw his head back, and keeping his solid lumberjack grip on my hips, started pistoning into me. How Erica kept her face on me while I got jackhammered like that I’ll never know, but with a long groan and shudder he came, and so did I sending streams of ropey cum into her warm inviting mouth. His penis pulsed inside me with a life of its own, before it finally softened and slid out. It was a couple of minutes before anyone could breathe again and sort out their clothing.

Derek nodded at the car we’d been using as our prop. “Hope we didn’t ding her up too bad, need a ride?”

“Again, you mean?” I retorted saucily as we piled into the SUV.

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