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Author's Notes

"This is the twentieth in the series. Each story can be read independently but is even better enjoyed in the series. The main characters, like Ashley, are based on real people. Their names, personality descriptions, some photos and many circumstances are theirs. <p> [ADVERT] </p>Some creative license is taken to enhance the enjoyment of writing and (hopefully) reading. Thank you for your support and encouragement in the series."

“Hi. My name is Ashley,” I said with a ring of bouncy enthusiasm. “Where do I sign up?”

“I’m Trix. Aren’t you a pretty blonde thing?” the slender brunette in her mid-thirties said, leaning against a motorcycle outside the suburban Phoenix bar. She took a drag on her joint and looked up with her squinted dark brown eyes, offering a smile. Her worn Harley tank top was tied in front, revealing her bare abs above her short cut-off denim skirt and black army boots. Her tanned, leathery skin told the story she was used to being in the hot Arizona sun wearing as little as possible. Her skin already glistened with sweat from the fast-rising temperatures of the desert’s sun. “Whatever you're signing up for, I want to be first,” her raspy voice added with a low snigger. Her eyes brazenly sized up my five-foot-eight athletic, curvy, thirty-five-year-old features.

“Uh, thank you?” I said, caught off guard by her bold flirtation. “The motorcycle club?” I added. “I heard there’s a ride today. I’m new in town. Is there someone I need to talk to?”

“Inside,” she said, unashamedly continuing to strip me with her eyes.

“Okay, thanks!” I answered as I turned toward the weathered, sunbaked, rustic door ready to begin this new adventure. Walking through that door was like walking into a new chapter of my life.

My life has become fast-paced and complicated. It’s how I like it. I’m an adventure seeker and adrenaline junkie. I’ve used my determination and assets to quickly climb the ranks in the banking industry as a rising star. Not to sound vain, but I’m confident, beautiful, smart, dedicated, and willing to do whatever it takes to get what I want. Much of it came following the example of my mom, Pam, a true work whore who has unashamedly fucked her way to the top as a banking executive.

If I’m honest, my attitude and drive are also from the influence of my perpetual indebtedness to Cliff. Two years ago, my over-confident risk-taking led me to wager my full submission to him on a golf game I knew I would win. I underestimated him in the game and what it would require of me in the following months of submission. I have no regrets. He’s changed my life, showing me what I really am and my deepest carnal desires. The more I surrendered, the more I craved being used. Despite my professional outward appearance, I relish the depths of depravity my clandestine submission to Cliff requires.

Things have changed fast. One month ago I saw an opportunity I couldn’t resist. I applied for a promotion at a bank in Phoenix that would take me away from life as I’ve known it in the Midwest. The process moved quickly after bank executives flew me in for interviews, examined my portfolio, and confirmed my willingness to do whatever it took to get what I wanted. My new adventures have taken me to the Southwest.

Excited for the move and change, I traded my car in for the freedom and the feel of power between my sensitive thighs of a new red Harley Davidson. Within two weeks I settled into my new place and job, eager to meet new people in my new city. A handsome new colleague recommended a motorcycle club he had heard about not far away.

Everyone in the bar turned when I walked in. Two guys were sitting at a table near the entrance. Two other men, including a tall skinny guy and a lone, pretty redhead stood around them. The redhead wore only a small black string bikini top that barely contained her full breasts, tiny cutoffs, and boots, leaving little to the imagination of her tanned, freckled body.

I was silhouetted by the bright Arizona sun behind me as I stood in the open doorway. All eyes looked in my direction. “Is this the motorcycle club?” I asked. “I was hoping to sign up for the ride. My name is Ashley.”

“Yeah, this is it,” the large man sitting at the table said as if holding court. “Doin’ a poker ride today. Startin’ in about 20.”

“Poker ride?” I asked.

“Fuck, she’s hot,” the lanky guy crudely said, with his eyes glued to my tits.

“Easy, Gasket,” the man at the table said. “We’re glad to have you join us. I’m Bronx, the club president. We have different kinds of rides to mix things up,” the big man continued, redirecting his attention to me. “Themed rides, adventure rides, fundraising rides. Every once in a while, like today, we hold a poker ride.”

“Sounds fun,” I said.

“We’ll ride all day making five stops, finishing here. You draw a playing card from a deck at each stop. The rider with the best hand at the end wins.”

“Great,” I said.

“Some just do it for ride and to see the hand they get. Others get in on the wager to win it all. Bein’ this is your first time, Little Lady, you probably want to just see what cards you get.”

“I’m here for the full experience,” I said. “Deal me in.” 

“Damn.”

“Easy,” the big man said to Gasket. “Keep your cock in your pants.” He looked at me. “Have it your way, Ashley. That’ll be five hundred. The club gets ten percent, and the winner takes home ninety.”

“Sounds good,” I said.

“We leave in 15,” Bronx said, standing up. When he stood I saw the magnitude of his size, rising to about six-feet-five, approaching four hundred pounds. Folds of his fat rolled out of his faded red tank top. He wore a pair of baggy Levi jean shorts. “You’re not wearing that on the ride,” he said, half in the tone of a question, the other half as an order. “Red, take her back and get her something different to wear. We can’t have her passing out from heat exposure on her first ride.”

“What’s the matter with what I’m wearing?” I asked, looking down at my white top, black jeans, and boots.

“Fuck no,” he said with a laugh. He gestured to the redhead, pointing toward the back of the bar.

“Come with me,” she said.

She took me to a back room next to the restrooms by the rear door to the bar. “Lose the pants,” she said. “I have a skirt you can wear.”

I took my boots, and black denims off. I stood there in only my white top and thong.

“Damn,” she said, almost with a jealous tone. “They’re going to love you.”

“Oh good,” I answered naively. “I’m hoping to meet new people.”

“Oh, you will,” she said, as she bent over to pick up a low-rise short frayed denim skirt. When she stood up, one of her ample tits fell out of her bikini top. Her puffy areola was as large as any I’d seen, pierced with a bar.  

My mouth dropped open at the sight of it.

“Like it? Bronx does too,” she said as she manhandled her breast back into the tiny black constraint. She handed me the skirt. “This might be a little small, but that’ll only work for you,” she said, with a wink. “The best thing about these rides is we will be way outnumbered by the men.

I wrestled the tiny skirt up my legs, doing my best to cover my proud booty. The bottom of my ass was completely exposed, not to mention my labia. “Do you have any other skirts?”

“That looks perfect,” she said. “We better get the fuck out there before they leave.”

Brazen cheers and catcalls greeted us as we walked out of the bar. They were almost drowned out by the roar of engines. More than twenty other bikers showed up for the ride. There were only two other women other than Trix, Red, and me. Red mounted the back seat to Bronx’s bike.

I put my helmet on, realizing I only saw one or two other riders wearing them. I immediately felt like it stood out like a beacon as a first-timer. The moment Red squeezed on the back of Bronx’s bike, he set out to lead the way, followed by the rest of the pack. I quickly joined in. It was exhilarating to be out on the open road with the rumble of the band of bikes around me. I felt a part of something. The warm air bathed my arms, body, and legs. We gradually picked up speed, adding to the adrenaline coursing through my body. No one could see my broad girlish smile hidden behind my black helmet.

I noticed that Gasket and other riders kept maneuvering for positions around me, stealing glances at my ass. I blushed under my helmet, understanding why they would prefer positioning themselves near one of the few women on the ride, hoping for a chance. I knew better than to tease them by offering better views, but I couldn’t resist. It felt good to have attention from new men in my new city. They weren’t complaining. It was just some harmless fun, right?

As we picked up speed the vibration of my engine intensified, radiating up toward the leather seat. I had never experienced it because I always rode my bike wearing jeans or thick pants. My almost naked labia pressed against the soft leather, making it helpless to the vibration. Having the attention of men around me with the direct vibration of my bike on my pussy triggered arousal throughout my body. “Oh fuck,” I said to myself beneath my helmet. I could feel my nipples tightening. The metal frame against the inside of my sensitive thighs heightened the response. My breathing quickened. “This can’t be happening,” I thought to myself. “I’m such a slut.” I wanted to slow my bike to ease the vibration, but the pack increased speed again moving down the freeway. If I slowed down, I’d fall behind, signaling the wrong message to Gasket and the other men I had been teasing. Yet, if I increase the bike’s speed to keep up, it would be like being tied down on a bed with a vibe strapped to my pussy, completely helpless to it. I had no choice but to keep up.

The climax grew gradually, which I knew meant it would become more intense. I took deep breaths trying to slow its climb and hold it off. I raised my ass to ease the vibration, but that only caused the bottom of the skirt to slide up further, exposing more of my ass to the men around me. The more I did, the more I dangerously teased them, sending a clear message. Seeing them watch my ass only aroused me more. I lowered my body again, forcing my full weight to press my helpless pussy against the intensifying pulsating of the bike. I was getting so wet, which caused my labia to slide more across the soft leather. If I raised my ass again, they would see how wet I was.

Sweat formed on my forehead under my helmet. My nipples were rock hard, further betraying my arousal for those around me who might notice. I gasped as the climax grew closer, quickly toward the point of no return. I was desperate for us to arrive at the first stop to save me from the danger of an orgasm while riding and the almost certain embarrassment that would come from it.

Bronx signaled the first stop was off the next exit.

“Please, please, please,” I begged the motorcycle gods that somehow I’d make it. The more I pleaded, the harder and faster the climax approached. My mouth grew dry. My stomach tightened with all the strength of my core. My legs twitched while I did my best to hold tightly to the bike with my strong thighs. We pulled off the exit. I felt the immediate relief of stopping at the stop sign at the top of the exit. It was only brief as the pack turned right and rocketed down the isolated road. The faster they went, the more intense the climax grew. I gripped the handles with all my strength as my entire body quaked in my seat from the orgasm. I screamed in my helmet. “Fuck yes!” We were still half a mile from our destination. I had no choice but to hold my pussy down against the intense vibration of my bike, especially in the lower gears. I suddenly gushed, completely drenching my seat. Euphoria and cold chills covered my body despite the warm desert air. The force of it caused me to squirt my juices to either side and behind me. I bucked in my seat, doing my best to maintain balance. Fuck, it was intense. I just hoped no one noticed. I lowered my ass again against the wetness of my virgin leather as my breathing eased.

“New-be is a bike whore,” Gasket said as he pulled up next to me. “You were fucking yourself on your bike! They’re not going to believe it when I tell them what I just saw.”

I quickly removed my helmet and flung my blond hair to the side. “Please, Gasket. Don’t say anything,” I whispered desperately. “I didn’t mean to fuck myself. It just happened.”

“It fucking did just happen,” he said. “I got sprayed by it. I thought it was raining.”

“Please,” I pleaded. “That’s never happened to me before. This is my first ride with the club. Please don’t embarrass me.”

A broad smile came across the lanky man’s face. “Our little secret,” he said.

“Thank you,” I replied, relieved. “I knew you’d understand. I appreciate it.”

“But it’ll cost you, bike whore.” 

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“Cost me? What will it cost?”

“A favor,” he said. “You’ll owe me.”

“You’re not serious,” I said.

“Watch me,” he answered, starting to step off his bike.

“Okay, okay,” I answered, reaching my hand to his shoulder. “You have a deal.”

“Deal, bike whore,” he said. “Our little secret. Time to grab a beer and pick up our first card,” he added as he walked away.

I couldn’t believe what just happened. I got off my bike and walked toward the bar. The inside of my thighs were drenched. I did my best to dry my pussy and the bottom of the skirt with my petite hand. It did little good. My nipples pressed through my bra and a semi-transparent white top. I felt naked as every head turned when I walked into the bar. Pitchers of beer were already being emptied. The anticipation grew for the first draw of cards. I tried to blend in but secretly felt horny as hell.

This became my first opportunity to see who else was on the ride. Except for the few of us women, it was almost all men. Red was on the ride with Bronx. One other woman was with her husband. The thirty or so men ranged in age from early twenties to early seventies. Some looked clean-cut and professional while others looked like they’d be more comfortable in a bike gang than a motorcycle club. Some were decked out in expensive bike gear while others were dressed casually.

It didn’t take long for several men to move closer and start hitting on me. I’d be lying if I said I didn’t like the attention. I playfully flirted back, my pussy still buzzing from the climax on my bike. The attention from all the guys meant I had all the free beers I wanted. It made me even hornier. Knowing myself, I was aware things could easily get out of hand. I also knew it was going to be a fun day.

As we drank beers and played darts, I started to relax more. The men were flirting hard and jockeyed for my attention. I’m not one to back away from opportunity. I mercilessly flirted back with them. My playful flirting only emboldened the men. The sexual tension escalated fast. 

I was especially drawn to a tall, muscular guy named Tom. He was about my age with short light brown hair and around six-foot-two. He said the club and its rides were an escape from the stresses of his work as an attorney. We hit it off with a lot in common like enjoying new adventures and being outdoors.

Bronx announced we were heading out for our next leg of the poker run. He instructed everyone to pick up a card from Red on the way out.

“Want to make a little side bet?” Tom asked as we walked toward the exit.

“What do you have in mind?” I asked, flirting back with a wink. 

“It’s our first card of the ride,” he said. “High card? Loser buys beers at our next stop.”

I hesitated.

“You don’t have to,” he said back-pedaling after my delay to answer. “I know we just met.”

“Oh no, I’m in, handsome,” I answered, never one to back away from a challenge. I offered a coy smile and playfully pushed on his broad shoulder. “The problem is, I’m already getting all the free beers I want. That would be a waste. I’d want to play for higher stakes.”

“Oh really,” Tom said. “What do you have in mind?”

“Your shirt,” I said without thinking, stunned at the words that just came out of my mouth.

Tom smiled broadly, also surprised by my boldness. “Are you kidding?”

I only smiled back in response. “I never kid when I make bets.”

“You’re on.”

A thousand butterflies filled my stomach. My pussy moistened again. What did I just do? I really am such a slut. There was no backing out now. We walked together toward the door. Red handed Tom a card from the top of the deck.

“New girl feeling lucky?” Red asked as I stepped up to take my card. “You look hot in my skirt. Looks like you’re making a lot of friends.”

“I am and like my chances,” I answered back teasingly with a glance toward Tom.

“Hey everybody, the new girl is feeling lucky,” she announced loudly. She waved the top card around in the air, drawing attention to herself before dramatically sliding the card inside the front of her shorts.

The entire bar of bikers laughed and cheered at her impish move. 

“Then you better get your card and see how lucky you are,” she said, licking her lips while locking her eyes onto mine.

My jaw dropped in surprise. “Seriously?” I asked.

“It’s all in fun,” she teased. “At least I’m letting you use your hands.” The look on her face showed how much she was enjoying publicly embarrassing me as an initiation to the club.

I blushed as the crowd started chanting, “Lucky! Lucky! Lucky!”

My strong competitiveness kicked in, especially after being publicly challenged by her. I also felt horny from my climax and all the attention I was getting from the guys. I stepped in closer, locked eyes with her and slowly pushed my hand down the front of her shorts. I’m more attracted to men than women, but if she wanted to dare me like this in public, I was happy to play along and make the most of it. I suddenly realized she wasn’t wearing any panties. My fingers slid down the back of the card, causing the knuckle of my petite middle finger to move down the folds of her already-wet pussy. My knuckled paused to circle her clit before stroking the length of her folds. 

“I know it’s in here somewhere,” I teased, answering back with as much confidence as she challenged me with.

Red’s knees buckled, not expecting my playful response to her challenge. She thought I’d blush, pick the card out quickly, and back off at being teased. She was trapped and immediately became wetter from my touch.

I smiled and looked her in the eyes as if she met her match. My petite knuckle pressed harder against her clit, circling it faster. “How could a card that size get lost in here?”

The watching men roared with laughter. Red’s arousal grew as the crowd watched Bronx’s girl being fingered in disbelief.

“Oh fuck,” Red said. “Wait, wait!” She tried to pull away.

The bikers all cheered. “Lucky! Lucky! Lucky!” 

Red looked at Bronx, with a pleading stare to be rescued. She couldn’t believe Bronx was allowing it to happen.

“Fuck, the new girl’s good,” Bronx said.

The crowd watched the show in disbelief. No one had ever been allowed to touch Red. She was Bronx’s property. Men had been put in the hospital for trying, but no woman had ever tried. Red attempted to publicly embarrass me by putting my card down her shorts. I was happy to turn the tables and win respect from the watching crowd. I moved in closer and turned my hand in her shorts, allowing my middle finger to slide into her already-sopping pussy.

Red’s body convulsed from the growing climax. Her left tit shook loose from the tiny strings of her bikini top. Her large, pierced puffy nipple was completely exposed to the bar.

The crowd of bikers cheered, all the more.

“Please, Bronx,” she pleaded, never been taken by a woman before, let alone in public. She reached up to adjust her rogue tit back into her bikini top.

“Leave it,” Bronx thundered with a smile, enjoying the show.

Red’s breathing intensified from the involuntary exhibitionism. “Oh fuck! Oh fuck! I’m going to cum!”

I suddenly pulled my fingers and card out of her shorts. They were drenched.

Red’s knees buckled again. “No, no!” she cried. She was so close to climaxing she didn’t want it to stop even though her humiliation made her desperate to be rescued.

“She’s all yours Bronx,” I said with a wink. 

“Fuck yes,” he growled. “I like this new girl.”

I relished the attention in the room. I raised and waved my petite hand above my head. “Anyone want to suck my fingers to get a good taste of Red?” I asked as I wiggled my dripping digits in the air. The room roared. Several men and Trix hungrily moved closer.

Red’s face turned beat red with a murderous look. “You slutty little whore,” she growled. 

“It’s all in good fun,” I mimicked back playfully.

“No one is getting any of Red,” Bronx suddenly roared, “except me.” He appeared like a giant wall next to me. 

“Then I guess this belongs to you,” I conceded, wiggling my fingers toward his gargantuan face.

Bronx claimed his prize. One at a time, he took each finger into his mouth, sucking them in and licking them clean in front of the watching crowd. Red’s face grimaced as she watched her man savor and lick my fingers clean in front of her. I moaned for effect, further humiliating her.

“You’re welcome,” I said teasingly as I pulled my pinky finger from his lips, leaving the two of them to contemplate what just happened. I walked up to Tom to compare cards. “We still have a bet,” I said, showing my wet queen of hearts.

Tom’s face sank, showing his eight of clubs. “You are lucky and fucking hot,” he said. “That was incredible.” 

“I’m just that good,” I answered feeling invincible. “That’s only a small taste of what I’m capable of.”

Tom took off his shirt and tossed it at me, hitting me playfully in the face before falling crumpled in my hands. I was more impressed than I anticipated, seeing the lines of his fit abs.

“Better luck next time,” I said. 

“Oh good,” he said. “I’m glad there’s a next time. Blackjack at the next stop?”

“You’re on,” I said, feeling indomitable. I smiled boastfully, admiring the view of his toned, muscular upper body beginning to sweat in the Arizona heat.

Beer flowed and Red dealt cards at each stop. Tom won our next side bet at the second stop with the six of clubs to make fourteen. That beat my twelve when Red handed me the two of diamonds. 

“I always pay my debts,” I said as I started to take my top off.

“I’ll take your bra,” Tom said boldly.

“Fuck no,” I said. “You gave me your shirt, I’ll give you mine,” I flirted, knowing my bra would cover me like a bikini top in the Arizona sun.

“You got my shirt because it’s what you said you wanted,” he answered playfully. “I won this time, and it’s my call. I can pick something else if you prefer.” 

“Fuck,” I said as the whole bar watched what I would do next. I unclasped my bra, pulled my straps down my arms, and yanked my bra out from under my top. I threw my bra at him. The sweaty transparent top did nothing to hide my large tits. My hard thimble-sized nipples betrayed my intense excitement at seeing the way Tom looked at me and the exposure to everyone watching. My pussy moistened from the arousal. I knew I would be helpless to another climax getting back on my bike with how I was feeling. I watched as he dropped my bra into the trash can as we left the bar for the next leg.

The pace and intensity of the playful flirtation rose with the desert heat for the rest of the day. It was the most fun I had in a long time, including since making the move. I loved getting out on the open road on my bike with new friends. Even more, I loved all the attention I was unashamedly attracting from the men. 

The sun began to set as we arrived back at our starting place. I couldn’t remember ever feeling hornier except maybe with Cliff in Costa Rica. I knew my day or the fun was not over. I’d get dinner from Tom and he’d get the fuck of his life after. Everyone went into the bar for a final beer and the last card dealt by Red to see who won. Red handed Tom the ten of clubs, completing his flush.

I stepped up behind him and received my last card from Red.

“Damn,” I said, looking desperately for some kind of connection between the five cards. They were nothing but a random, worthless assortment.

“The dealer always wins,” Red said with a wink and her devious smile. “Never fuck with me until I’ve dealt your last card.”

“Shit!” I said, realizing she’d been playing me all day long, dealing me terrible cards.

“Time to show your hands,” Bronx said, ready to announce the winner and prize.

Tom was quick to put his hand down, certain of victory. We all followed.

“Fuck, that’s a bad hand,” Gasket said. In that moment he dropped his royal flush, ten to ace of spades. 

Tom’s face fell in defeat.

“Congratulations, Gasket. You win,” Bronx announced.

“Keep the money,” Gasket said. “I’d like to claim another prize. Don’t you all think Ashley deserves the proper initiation to our club?”

The crowd started chanting, “Lucky! Lucky! Lucky!”

I looked up at Tom. “What does that mean?” I asked.

“It means you’re the prize if you want to be.” 

My pussy tingled as I watched all the men close in around me. I relished how much fun the day had been flirting with them, especially Tom. I smiled, secretly feeling like I had just won, despite the worst poker hand of my life. I wanted to make new friends. It’s time for them to get to know the real me.

“Take me home after?” I asked with a glance toward Tom.

“Absolutely,” Tom said.

I pulled my shirt off and said, “Fuck yes, then. Come get your prize. It’s time to be properly initiated into this club.”

The circle closed in around me, with Trix pushing to the front.

Published 
Written by cliff_edger
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