Wild Wendy
I came here from the east looking for thrills and a couple of bucks.
I quickly found a money maker in gambling. Blackjack, poker, craps. I thought I was such a pro. I was nearly making more in a day than barmaids did in a month. Then again, they're just women. The most popular game at the time was Faro, and I was best. People lined up to play or watch me play. The game is as chance dependent as can be, yet I rarely lost. I recall multiple streaks exceeding eight or nine wins. Not to brag. Gorgeous lady luck was on my side. I became a regular dealer. The gaming became easier, though I still handed the occasional win, just to keep them coming back. But they were only small sums. All intentional.
Then there was one day. It was mid cattle season, which is of course when the population of this town swells. All the rowdy cowboys come, my favorite marks. They love the gamble, there's plenty of them, they're often drunk, and most importantly, cattle season means they have money. And this is the most popular saloon 'round here. I sat at my usual table. It was the same group of lovable bastards as last year, the year before, and the year before, and so on. It was me, the ever slick red fox. Charles, my accomplice, pal, and the town coward/drunkard. The saloon's owner, whose name escapes me. And a bunch of other nobodies. It was a dull day. No targets. I saw a cowboy in the corner. His attire gave it away, as well as the fact he was only ever here during the season.
I'm a natural snoop. So I made my biggest mistake. I asked about him. Charles of course knew who he was. His eyes lit up at the sight. "That's Wild Will, the nastiest madman you'll ever see. I heard he once shot a man for dropping a nickel." A man to my side interrupted. "His aim's so good, I heard he ricochetted the bullet right of the nickel mid-fall and it hit the fellow right between the eyes." It seemed everyone knew about him. I just scoffed. "He looks pretty short to me." I looked over another time. I could see him sipping from his mug, glancing at me. He heard. I showed no fear. Lunatic or not, I was safe in here. Only in here.
The next couple of months flew by. As usual, I was on a roll. My hands moved at the speed of lightning, and my victories boomed like thunder. I even bagged a few, particularly charmed bar women. The sex was great; I didn't even have to get to a red-light district. Anyway, back to the card games. Charles assisted me as he always had, and we scored tons of winnings. But there was one problem. I often looked towards the corner. Each time I did, I could spot Wild Will peering over at me, not so much me but more importantly my cards and strategies. I was truly afraid now. He was onto me.
It was soon the next night. Cattle season was almost over, and it was last call on drinks. I was as drunk as I could let myself be; things were dandy and I was still mostly winning. I was full of pride and stupidity, and it was about time for me to wrap up the night. "If anyone else wants a go at the king of cards, now's your chance." There were no takers, except for one. It was Will. I ushered him over. "Come on over, little guy. How about we play some Faro?" William sat himself in front of me, and smiled, exchanging a large sum of money for chips. He was missing his lower right canine. I put down a good deal of my earlier winnings to open the bank. I looked up at him, and briefly scrutinized. For a psychopath, he was pretty well-dressed. A white cotton shirt with a stand up collar, and black dress pants. You could have seen leathery boots which could have cost a lesser man a fortune. His hat was a dutch, and a bit too tall for his head.
The cards were face-up in my custom dealing box. All of his large sum was placed on Three. He stared zen-like at my hand as it moved, tracking it. I hesitated, but continued. I burned off the first card, the "soda". The next card was my card, and sure enough it was Three. I felt like sweating. He was really onto me. As I was the banker, drawing the Three meant he of course lost his money. But he just laid down more money. "More." I was again tense. Maybe he wasn't onto me, maybe he really was just insane and wanted to waste away his money. So be it, then. He placed the chips on the Jack. I first had to draw the player's card, then I drew another banker's card. It was the Jack. I had to think quickly now. If I won again, it'd be suspicious... or an upset and broke Wild Will might even end me. I fiddled inconspicuously with my dealing box. "One more game." His voice was strained, and gritty as always. I finished toying with my box. He scooped every last dollar from his pockets, and even change. And all of it was placed on Five. Then everything went in slow motion. My hand drew from the box. Will's hand snatched mine by the wrist, and held it up. I was caught, two cards in my hand, one hidden behind the other. I was instantly exposed as a fraud. "You used a rigged box. Not to mention, you used prepared cards." Wild Will smiled minus a tooth, pointing to the slightly odd edges of two of the cards in my hand. The reaction from the crowd was quiet, but still there. Boy was I fucked.
I lost. He scooped away all of his money, and the money I put down, and again cracked that smile minus one tooth. I immediately tried to slink away and out of the saloon. But he just continued to hold me by the wrist. I dropped my handful of cards. "I said all or nothing. That includes your life." My heart skipped a beat. Not only was I caught, but I was in for much worse. I was dragged out, and on his way out he took his revolver from the saloon owner whose name escapes me. We walked outside. Everyone said Wild Will was insane, which caused me to practically tremble in fear. If he shot a man for dropping change, I could only imagine the fate of a sleazy conman like me, who tried to cheat him out of his money.
I expected us to arrive at somewhere secluded, so no one will see my brains splatter. My surprise when we entered a hotel. I figured he'd rather have room service clean up the mess. He threw me into a room and locked the door behind us. I prayed. Here was a killer cowboy about to do in an unarmed sharp like myself. I laid there on my back, awaiting death. Will flung off his hat, revealing tresses of long, blonde hair. He unbuttoned his classy button-up shirt and showed me bandages which tightly hugged his chest. My gut reaction was that he had a nasty chest wound, but on seeing the lack of blood, and him slowly unwrapping, I wised up. A pair of firm breasts bounced forward, and wrappings fell to the floor. Wild Will was a chick. She then undid the pewter buttons of her sturdy, striped trousers. Correction: Wild Will was a chick with a dick.
I was flabberghasted. Not so much that she was a woman, and had a cock. But that it was almost twice the size of mine. I examined her again, much like I did during our game. She had a taut belly, and breasts that could easily give you a handful. For a woman, she did have a pretty impressive amount of muscle. Yet she was still better looking than half the gals I met at brothels. She definitely seemed much taller from my position. "Suck it." Her voice was different from the one she feigned at the saloon. One could have easily mistaken her for one of those classier girls, were it not for her word selection. She had a nice voice and better features, but I was a man of principles. I would not suck a dick. She reached into her pocket and pulled out a wad of my dollars. "Don't you want your money back?"
I got up to my knees in front of her. I was drunk and it was a lot of money. I slightly widened my mouth. I took in the tip of her red and knotted coyote cock. My lips pursed against it, and my tongue started to massage the rod's end, lathering it in my spit. I didn't dare look up to see the smile that I was learning to hate. I couldn't help but taste her precum and inhale her scent. It tasted bitter and she reeked of arousal. I slid my lips downwards, my mouth engulfing more of the length. I could only take about half her cock without deepthroating. She thrusted against my face and I knew what she wanted. I placed myself on all fours, my hands and knees. Her dick was still crammed into my mouth, and I started to swallow more. Taking cues from many good time girls I've been with, I began to deep throat.
I shifted forward. Her thick, juicy meat sank further and into my throat. I gagged by reflex; I had never took a cock down my throat, or anywhere else. It felt warm and wet, and every time it plunged a bit deeper, I could feel it throb. It ran a shiver up my spine. I found the experience... Disgusting. She, greedy for satisfaction, forced me to go faster. Pretty soon, the girthy member was being pistoned into and out of my throat. I gasped for air between thrusts, sometimes interrupted from my gulps of sweet air by the cock again drilling into me. My nose was often right up against her crotch, her entire nine or ten inches of length hilted into me at a time, while all I could do was pant for air and let my esophagal muscles tighten by reflex. Her knot was only partially swollen, but still felt like a fist being forced past my lips.
The bitch didn't warn me. She came down my throat as soon as I gulped air, causing me to choke on some of the gooey load she spewed down my windpipe. I coughed, hacking the repulsive, salty stuff. I was aggravated, and choked so much I swear I almost died. That moment, I had the compulsion to bite down on the dick still lodged in my mouth, and considering how drunk I still was, it would have been likely. But I saw the pistol still holstered at her hip, so I just muttered. She leisurely dragged out of my mouth, leaving the taste of her salty cum. I spat the remainder on the floor somewhere, having had to swallow the portion she pumped down my throat. I looked up at her, weary and hoping this to be over. She simply told me to turn around, so I complied. Hands grasped at my trousers, and started to pull them down. This was so very humiliating; a woman undressing me like a piece of property, just to fuck my ass.
My pants dropped, as I remained there, on all fours like some craven slut. She peeled off my drawers as well, leaving me nude from the waist down. I held my head low, embarassed. My bare ass was hers for the taking, just a bit more than the scarlet tip of my smaller shaft poking out from the sheath. I let my tail hang to the side, tense as I prepared for what was to come. I felt a wet tip against my tailhole, and so I loosened myself to lessen the pain to come. The prod was followed by a sharp pain. She pounded into my ass. I was partially glad I lubricated her first, but I could still feel every inch of pulsing length slide in. It was sickening and felt odd. I could feel every slight bump, groove, and even vein of the hard on. It worked it's way into me, leaving a slimey wet trail that I could feel within me.
Then came the pain. I cringed in agony. In a smooth motion, she shoved the entire dick into me. I wanted to die. It stung and ached and felt like being split open at the seams. It was quickly starting to dry thanks to the growing friction, which was even worse. I swallowed down a whimper and took the anal abuse like a bitch, which was the best one could do. Her hips met my ass with maximum brutality, the bastard's hands at my shoulders. I lifted my head from hanging low, and gazed up at her. She looked down at me, smug. I saw her tits swaying along with her motions, my body being rocked back and forth as well. I would have punched her if I could have lifted up a hand. She just put her hand at my head and forced me to look back down at the floor.
She angled her thrusts. My face was against the floor as I remained limp, holding back groans. I felt an odd prodding of her tip against a certain spot inside me, the feeling strange yet pleasurable. My cock hardened, which I tried to resist, the repeated jabbing getting to me, precum dripping from my own tip. I bit my lip. There was no way I'd let myself cum. Honestly. By now her knot had fully swollen, which I feared more than the anal and my own orgasm. I felt the two huge lumps push against my rim, trying to penetrate. I was already too stretched; the bigger than a fist knot couldn't possibly fit.
But it did. She forced in the knot, and I felt like I had truly been torn apart. The cock gave a last thrust against my prostate before disappearing into me. I practically screamed in pain and came at the same time. My load was clear and watery, gushing against the floor. For the first time since I was a child, I felt like sobbing. The moments afterwards were just as terrible. The ache remained, my asshole stretched and stinging. I cringed in pain as she jiggled herself inside me to further my torment, the slightest movements worsening the agony. She was cumming again, the spurts of her second load burning me within. I had to... Beg for mercy. I did so until she was satisfied, and then started to yank. I was more prepared for this one, but nonetheless moaned just as hard as her cock ripped out of me prematurely. I nearly collapsed. That day was an eventful one for my anal virginity.
She turned me over, leaving me on my back. I felt terribly dizzy, and still buzzed. The pain seemed to radiate out; at the time I couldn't have stood if I wanted to. Her pants were fully dropped. Instead of balls, she had a pair of tender cunt lips. She wanted me to lick her clean, so I had to oblige. I leaned forward and my tongue extended, sliding against the shaft. It was wet with cum, a taste I could never grow a liking to. I slurped downwards, trying harder to ignore the taste, my tongue running over the knot. I followed a trail of her seed that lead down her sheath, and just between those lips. My tongue wedged itself between them, tasting some of her moisture.
This was more to my liking. My tongue ran expertly up and down the slit, leaving it slick and glistening. I pushed my muzzle up further against her, forcing myself onto her. I saw her giving in, trying to bite her lip. I finished lathering her labia in my saliva, every bit of pink left wet. I tongued into her, the dextrous muscle creeping inside. I wormed in about a couple of inches, and let my tongue squirm. It swished about inside, tasting more of her humidity and leaving my saliva. She tried to pull my face away, but I knew she was enjoying this, else she would have pulled harder. I withdrew and replaced it with my fingers, two of them slipping into her. She was really starting to lose it now, making attempts to pry me off. But I retained fortitude, working digits in deeper while my tongue lashed at her urethra right above her sexhole. I felt her climax, inner walls clamping down as they would for any other woman, though I forgot she still had a dick and thus her cum dribbled onto my hair.
I felt a growing stiffness between my legs, anticipating what was to come next. Oral always led to vaginal in my book. Given, I cheated a crazed killer who turned out to be a hermaphrodite and fucked me in the ass. But I've turned worse situations around. But she instead pulled up her pants and drawers. "Name's actually Wild Wendy. Thanks for the fuck. You were tighter than any brothel girl, and it didn't cost me a cent." She walked away coolly, picking up her shirt and dressings as well as dropping handfuls of my money. I tried to play it off as well. "James." As soon as she left, I picked up my dollars. She left a tip. Then I looked at my fingers. There was a small amount of her blood, at most a drop. I smiled in triumph.
I stuffed my pockets with green and pulled up my pants, still feeling sore back there. I tried to imagine what kind of person Wendy really was. And whether anyone would believe this, not that I'd ever tell to anyone. Except you. The next day I limped over to the saloon, hungover and sore all over. Nothing was quite the same after that. Plenty of people beat the tar out of me thanks to how badly I cheated them. They figured Wild Will roughed me up pretty badly, however, so they held back some. They were right. I no longer scammed my challengers, but never again did I have the same luck I used to. It's been a few years after that night. Every cattle season, I can't help but occasionally look at the corner of the room. I haven't seen her since, but I know she'll be back. She left me half hard and half naked. But I popped her cherry. And when that bastard comes back, I'll be the one fucking her in the ass. Fair and square.