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Alexandra, Damsel in Distress

"First experience with a trans-lady"

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I finished my beer and set the empty bottle on the rickety table. “I’m gonna wander on up the street and see what’s happening. Anyone wanna come?” I announced, rising from my seat.

“Yeah I’ll go, but I gotta piss first,” Sarge said, draining the last of his beer.

“We’ll catch up in a bit,” Digger added.

I nodded and made my way outside. The cool night air felt good as I turned to admire the historic station to my right and tried to imagine what The Drive was like a hundred years ago. Depot Drive, or The Drive as it was referred to, had a long and infamous history. From the historic station to the west for three full blocks to the east, everywhere you looked was a piece of history. During the heyday of the railroad, The Drive earned its well-deserved reputation. The street was lined with saloons at street level and hotels, brothels, and gambling houses above. All of this packed with travelers, railroad workers, con artists, and criminals. The Drive’s infamous reputation became known far and wide, and one famous First Lady disembarked just to see it for herself.

During Prohibition, the bars simply moved underground and set up candy stores, barbershops, and with other businesses as fronts. Several underground passages were built for patrons to easily move from one speakeasy to another without being seen. When prohibition ended, the bars and taverns moved back to street level. Later, other illicit endeavors utilized the hidden network for their operations.

As modern modes of transport took over and rail travel faded into history, The Drive faded too. The hotels closed one by one and the brothels were raided and shut down, but many of the bars remained. The Drive’s rough reputation continued as bikers, drug dealers, prostitutes, and criminals moved in.

In the mid-nineteen-eighties, the city decided The Drive needed to be cleaned up and transformed into a place for decent people. They bought, or simply took several of the abandoned buildings and demolished the more dilapidated structures. Property owners were warned to clean up their properties or have them condemned and taken. Increased police presence pushed out the drug dealers, prostitutes, and criminals. New sidewalks and street lamps were installed and trees were planted all along the street.

When beginning the project, city leaders envisioned The Drive as lined with cafes, ice cream shops, art galleries, and other family friendly establishments. However, they overestimated their ability to erase the long sordid history of The Drive. The bikers stubbornly refused to be pushed out and maintained their hold on the West End of the street. In addition, the big money investor, who they had been more than happy to assist in acquiring the entire eastern block, suddenly changed his plans and instead of restaurants and shops, he opened several bars, taverns, and night clubs. Other than a couple of new restaurants, The Drive remained primarily three continuous blocks of bars and taverns. The first block to the West belonged to the bikers. The third block, to the East, was the new clubs and restaurants catering to the Yuppie crowd. The middle block had one biker bar, a pawn shop, The Tropic Lounge, and a vacant lot where two buildings had been demolished.

The Tropic was the one place where the bikers and the yuppies mixed, along with the third group on the street, the pool sharks. Louie, the owner of The Tropic, liked to play pool and he was good, so were all of his friends who hung out at The Tropic. Some very high stakes games were played there, if you were gonna play pool at The Tropic, you better be damn good and have a lot of cash. In addition to his income from the club and playing pool, Eddie was the bail bondsman of choice for The Demons, the local outlaw motorcycle club, a very lucrative position to hold. Being the one the club turned to for bail meant that Eddie always got paid, even if a member jumped, and also meant that The Tropic was under the club’s protection. No member would ever get out of line in The Tropic or let anyone else cause problems. Being a bail bondsmen also meant that Eddie had a good relationship with the police. So when the city’s push to clean up The Drive came along, the cops refused to hassle Eddie the way they did the other bar owners.

A typical night on The Drive meant parking the bike in front of Tarantula’s at the West End and having a few beers there, then making my way from bar to bar until arriving at The Tropic, then working back down the street. All night long, groups meandered up and down the street in and out of each bar along the way. Only occasionally did we wander up to the eastern, respectable end of the street, and then, only to have a little fun putting a scare on the yuppies. They never wandered down to our end of The Drive. The farthest they ever made it was The Tropic. They came there to get a cheap buzz as the drinks were a third the price of those at their respectable clubs. We only tolerated them out of respect for Eddie.

The cool night air had barely filled my lungs when I heard a scream and the sound of people running. I turned in time to see a blonde woman run past me and three yuppie douchebags chasing her. Instinctively, I stepped in front of the lead douchebag. He ran into me full force and went sprawling into the gutter. His two friends skidded to a halt, staring dumbly at their buddy sprawled on the ground and raising their hands as they slowly backed away from me. I was at least six inches taller than either of them and probably a hundred pounds heavier.

“Hey man, we don’t want no trouble with you,” one of them said.

“Then you shouldn’t be harassing women on my street,” I sneered, taking a step toward them.

“That ain’t no woman! It's a dude in a dress!” the one on the ground shouted, slowly getting up and brushing himself off.

I half turned and glanced over my shoulder. The woman had stopped about twenty feet down the street and was watching with a frightened look on her face. She was slender, about five feet tall, and her low-cut top showed off firm round breasts. Her short black skirt didn’t quite cover the lace tops of her stockings and her stiletto heels accentuated her long legs. She had a great set of legs and looked all woman to me.

“Looks like a woman to me,” I sneered, turning back to the douchebag.

“It’s not, it’s a freak pretending to be a woman,” he shouted again.

“Yeah!” his friends chimed in unison.

I narrowed my gaze and stepped closer, forcing the douchebag to retreat. “You’ve got ten seconds get the fuck outta here!” I growled.

All three quickly retreated to what they thought was a safe distance, then douchebag turned back and shouted.

“What, you wanna suck her dick!”

All of the commotion had drawn attention inside and when he turned to run, he ran square into Digger’s massive barrel chest.

“This one’s cute and feisty, he’s all mine,” Digger grinned, grabbing Douchebag's ass.

Douchebag yelped and twisted away as his friends raised their hands and slowly backed away as Sarge advanced, his sixteen-inch Bowie gleaming in the street light. I noticed movement behind Digger and signaled Sarge to put his blade away just as two cops rode up on bicycles.

“What’s going on here, guys?” Officer Jenkins asked, stepping off his bike.

Jenkins was cool, he worked the drive a lot and never hassled anyone over petty shit. The regulars on The Drive knew him well, and we all had his back if needed.

“These boys seem to have a problem with the lady,” I answered before the douchebags had a chance to speak.

Jenkins cast an amused look toward Douchebag and friends. “You boys having a problem with this lady?” Jenkins asked.

Jenkins’s partner was new on The Drive and a little big to be pedaling around on a bicycle all night. He’d been trying to catch his breath since they pulled up. Now he swung off the bike and loomed over the douchebags.

“That ain’t a lady, it’s a dude in a dress,” Douchebag nearly shouted at Jenkins.

“And what were you going to do about that?” Jenkins glared.

“We were… uh, nothing, officer. We weren’t doing anything. it was just a... a misunderstanding,” Douchebag answered, his voice faltering as he realized what he was about to confess.

With a doubtful expression, Jenkins nodded and said, “Stay right here.”

Sarge, Digger, and I subtly taunted the three, being careful not to draw the attention of Jenkins’s partner. Jenkins walked over to talk with the woman. After a brief conversation, Jenkins returned to inform the douchebags that she didn't want to press charges and warned them not to cause any more problems. As they skulked away, Jenkins turned to Digger, Sarge, and I.

“I appreciate you guys stepping in to protect the, uh... lady, and it’s all right to put a scare in those idiots, but please tell me it wasn’t going to go any farther than that,” he said, glancing down at the knife hanging from Sarge’s belt.

“Just keeping the streets safe from the criminal element, Jenkins,” Sarge grinned.

Jenkins tried to hide a smile as he shook his head, “Yeah I'm sure you are, Sarge,” he scoffed, climbing on his bike.

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“We’ll be keeping an eye on those three, just to be sure they don’t run into anymore trouble,” Jenkins warned as they swung their bikes around and pedaled away.

As Jenkins and his partner rode off, the woman cautiously approached. I turned, getting my first good, head to toe, look at her. Long sexy legs, round hips, narrow waist, plump breasts, pouty red lips, smoldering green eyes, and long silky blonde hair, certainly looked like a woman to me, a beautiful sexy woman at that. Despite the accusations against her, I felt a familiar hunger growing in my loins.

“You okay, hun?” I smiled, stepping closer.

She flinched a little at my approach, but recovered herself and smiled nervously. “I’m fine, thank you so much. Those guys might have killed me if you hadn’t been here,” she said, her voice soft and feminine.

“Always happy to help a damsel in distress,” I smiled. “They call me Beast,” I said, offering my hand.

Her nerves seemed to settle a bit as she placed her small hand in my massive paw. “Alexandra. It’s lovely to make your acquaintance, Beast,” she giggled a little. “So, are you really a beast?” she asked, stepping closer.

“When I need to be,” I grinned, squeezing her hand gently. “This is Sarge and Digger,” I said, introducing her to my friends.

“Nice to meet you both, and thank you too. Such colorful names too,” Alexandra said, seeming to get past her nervousness.

“No problem, you gonna join us for a drink?” Sarge smiled.

“Oh, I’ve had enough excitement for tonight, I think I’ll just get a cab home, but thanks for the offer,” Alexandra declined.

“I can give you a ride if you want,” I offered. There was just something about her and I couldn’t let her get away so soon. I found her intriguing and had to know more.

“Are you sure? I don’t want to disrupt your night more than I already have,” she said, batting her eyes at me.

“Nah, it’s no problem, I want to make sure you get home safe,” I heard Sarge snicker as I spoke to her. I looked over and Digger was trying to suppress a laugh.

Alexandra laid her hand on my chest and moved closer. “Such a gentlemanly beast. Thank you so much,” she said, brushing against me.

“You two have fun,” Sarge called as he and Digger walked away snickering.

I slipped my arm around Alexandra’s waist and walked her to my bike.

“Mmmm, I’ve always wanted a big hog between my legs,” she giggled as I swung my leg over the seat.

"Just wait until you feel it vibrating between your legs," I winked at her.

An excited smile covered her face as she climbed on and held me tight, pressing her firm breasts into my back as we rode up the street. She squealed and squeezed me tight as I cracked the throttle and the bike shook beneath her. Her breath was hot in my ear as she directed me to her house. By the time we arrived, her hand was rubbing my rapidly swelling cock through my jeans.

“I can’t wait to get this in my mouth,” she said, squeezing my swollen shaft as I switched off the bike.

She kissed my neck as she climbed off the bike. Taking my hand, she led me to the front door, her heels clicking on the driveway as her ass wiggled beneath her tight skirt. I still couldn’t believe this wasn’t all woman, but she had never denied the douchebag’s accusations. I just couldn’t see how it was possible and, at this point, I didn’t care, all that mattered was that I wanted her.

The door clicked shut behind us and Alexandra melted into my arms. Our lips met in a heated kiss as her fingers unbuckled my chaps and belt. My hands covered each of her smooth firm ass cheeks as I explored her warm mouth with my tongue. A rush of cool air met my rigid shaft as she freed it from the overheated confines of my jeans. I groaned into her mouth as her warm fingers wrapped around my shaft and started slowly stroking me. One hand began fondling my heavy balls as the other slid over my throbbing dick. I began opening her blouse to expose her lacy black bra and the firm round breasts within.

Alexandra shrugged the blouse off and let it fall to the floor as she cupped her breasts and teased the hard nipples through the lace cups of her bra. I reached for her, sliding my rough hands over her smooth flesh up to her bra clasp and quickly released it. A hungry growl rumbled deep in my chest as I took in her smooth creamy skin and perfect round breasts capped with stiff pink nipples.

With a giggle, Alexandra pulled my T-shirt up and lightly drug her manicured nails over my hairy chest, sending a shiver through me. She stepped forward, pressing her breasts into me as she kissed and bit my neck. Her hand returned to my swollen cock and she began kissing her way down my body, dragging her hot tongue over my flesh as she went. Once on her knees, Alexandra lifted my cock and began licking and sucking my big hairy testicles. I groaned aloud as she sucked one into her warm mouth. She stared up at me and licked along the underside of my shaft up to the swollen leaking tip. She swabbed the sensitive tip with her talented tongue before parting her soft pink lips and sliding them down over my aching cock.

My eyes closed and I pushed my hips out at the unbelievable sensation of her warm wet mouth engulfing my stiff member. Her tongue massaged the underside of my member as she bobbed her head, taking more and more of me each time her lips slid down my pole. She gagged a little as my thick cock entered her throat. She pulled back, took a breath, and plunged her mouth down my shaft again. I felt her throat expand around the swollen head and her lips reached the base. My knees went weak and I grabbed her head for support. She moaned around my cock plugging her throat and I nearly came from the intense sensation.

I stepped back, pulling my cock from her delicious mouth and lifted her up to kiss her again. I picked her up and her long legs wrapped around my waist as I squeezed her ass and our tongues dueled in the moist heat of our joined mouths.

“Oh fuck me, Beast! I need you inside me,” she breathed, breaking our kiss.

I kissed her neck and breasts as I carried her to the couch and laid her upon it. She lifted her legs as I gripped the waistband of her panties and slid them off of her and there it was, a stiff little cock pointing up at me. She pulled her legs back and lifted the smooth hairless nut sack exposing her pink little rosebud. She looked so hot, I lined my thick hard cock up with her tiny hole and pushed. Her eyes went wide as her opening stretched around my swollen cock. I continued pushing until her tight entrance yielded to my invasion and my fat tip slipped inside her hot passage.

“Ohh, fuck me,” she moaned as my thick tool pushed up into her.

She was so tight, I pushed slowly, trying not to hurt her. Her eyes closed and her mouthed formed an, 'oh,' as she breathed out. I groaned from the tight grip around my hard shaft as it slid deeper. My hips met her firm ass and my bone was buried to the hilt in her tight boi-cunt. I leaned down to kiss her hot lips as her tight hole squeezed my throbbing meat. Our tongues danced together and I began slowly pumping my hips, stroking her hot tight hole with my hard shaft. Her hands stroked my chest and pinched my nipples as I picked up the pace. She moaned quietly each time I bottomed out in her clutching pussy.

“Oh, oh, harder, fuck me harder,” she begged.

I pumped my hips faster, plunging my cock deep inside her. My hips slamming into her ass hard. My mind was spinning from the electric pulses emanating from my throbbing cock as it plunged in and out. I felt the pull in my balls and knew I wouldn’t last much longer. Grabbing her ankles, I pushed her legs back and drove my cock into her harder and harder until with a final deep thrust, I exploded inside her. She screamed as I unloaded deep in her boi-pussy. My legs trembled and my hips jerked with every hot burst of cum. I gasped for breath as my cock twitched in her flooded cavern. I slowly stroked her a few more times as I caught my breath and the intensity of my orgasm faded. She moaned and pulled me down on top of her.

"Oh, you are a beast," she sighed, pressing her soft lips to mine.

As we kissed, I noticed the cum on her flat stomach and breasts. I scooped it up with my finger and fed it to her between kisses. We kissed and caressed each other, regaining our strength before she sucked my cock back to life and rode me to another gut wrenching orgasm.

The following night I walked into Tarantula’s, as usual, and Bull got up from the table as I approached. Bull was a big man, almost as big as me, and known for being a little unstable. He walked up and stared me straight in the eye with an accusing look. He sniffed a couple of times.

“You fucked the girly boy, didn’t you?” he accused.

I stared back at him unsure how to answer and prepared myself for a fight.

Taking my silence as confirmation, he exclaimed, “My brother!” and threw his thick tattooed arms around me.

“See he knows, I told you guys, ain’t nothing like fucking hot girly boy ass,” he announced, turning back to the table.

“Oh god, now there’s two of em,” Sarge shook his head.

The whole table erupted with laughter.

Published 
Written by BadDog9
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