The Highwayman

I awoke slowly, blinking in the weak light from the single sputtering candle in my dingy room. I slept in a tiny cramped loft above the stables in the infamous Flophouse tavern. After taking a moment to re-evaluate my lodgings, it became obvious that this boy needed money, and fast. In this day and age, with my limited work experience and resources, there was only one source of easy money: the Golden Gap Way.

I slid my black silk shirt on (a true highwayman must always look his best), and tugged on my soft, suede riding boots. I popped up the caging trap door and dropped lightly onto the hay-covered floor, letting my eyes adjust to the slightly dimmer lighting. My faithful steed Shadow trotted towards me as I was retrieving my bag of gear from its hiding place in the rafters. Examining the contents, I found both pistols, still loaded. I then drew my most prized and most expensive possession, my glimmering steel rapier, the weapon of a gentleman.

I crept to the entryway to the stables, checking for roaming patrols, because your humble narrator was wanted for many dastardly deeds, and was also not paying his rent. Seeing the coast clear, I led Shadow out into the open night. I swung up into the saddle, dangling my sheathed sword along his flanks at the ready. Taking a deep breath, I settled my nerves, spurred Shadow ahead, and raced off in search of riches and excitement.

Flying down the road, chased by a growing cloud of dust, I scanned for the telltale lanterns of carriages. As Shadow and I crested a steep hill, I saw the glimmer of moving lights in the distance. We moved back under the cover of trees on the side of the road. I quietly dismounted, and lashed him to a low-hanging bough. One drawn pistol in my hand, I crouched, and waited. My heart racing, I could hear the hoof beats pounding on the hard road, carriage wheels clattering, I gripped my pistol tighter. As the rattling carriage raced past, I leapt up and out, snatching a hold of the luggage rack on the rear.

The carriage’s momentum swung me around, and I clutched tightly to the bags lashed there. Holstering my pistol, I slowly and quietly crawled up onto the roof. Keeping low, leaning into the wind, I crept towards the coachman, once again drawing a trusty flintlock. I knelt behind him, and cocked the hammer back, causing him to immediately whip around. With a rakish grin, I gestured towards the creek that paralleled the road. With a frightened swallow, he sprung from the bench, sailing out into the water, rolling and splashing downstream. Without guidance, the horses began to slow gradually. I took the reigns, guiding them to a stop on the side of the empty road.

Wondering who my passengers are, I hop down, strolling around to the carriage door. I pause, taking a moment to compose myself, brushing the dirt from my clothing, and pulling my baby-fine brown hair back. I pull my rapier, and yank the door open, lunging up and into the compartment. I freeze as I land, the tip of my rapier barely grazing the pale cleavage of a young woman. I stared in awe, her black velvet gown contrasting her fair skin. Her short copper-colored hair brushing her collar, her eyes wide with fear. As I watched her more, I noticed her heavy breathing, which made her breasts strain against the low collar of her gown quite lusciously.

Slowly lowering my rapier, I bowed deeply, smiling up at her through my curtain of hair. I took her shaking hand, and kissed it lightly.

“Well fair maiden, you have the pleasure of being robbed by the most courteous highwayman of them all. I’m Sebastian.” As I held her soft hand, lightly stroking it against my cheek, she replied that her name was Lana. My tongue flicked out, brushing the inside of her wrist, causing my fair maiden to shiver, biting her lip.

“I…I have no money…please take whatever you want from the luggage”, she whispered nervously.

Still holding her hand, I slowly drug my tongue across her palm and responded that I’d have to take my compensation some other way. She glanced down at me nervously, so I smiled up at her through my hair, nibbling her inner wrist gently. At that, she gave a shaky sigh, and sank back into the plush seat.

Leaning in towards her, I slowly pushed up her soft velvet sleeve, baring her pale arm. Slowly kissing my way up her inner arm caused her to begin to tremble. I then took her arm, kissing the inside of her elbow lightly, and then sucking on it, gently at first, but then harder. Lana groaned almost inaudibly as she reached out, running her fingers through my soft hair. I rose up and leaned towards her, my lips barely brushing the side of her neck.

As she gasped softly, I gently bit her neck, caressing the soft skin with my tongue as I did. Her strong hands gripped my back, pulling me closer. Caressing her neck with one hand, I continued to lick and nibble my way up the other side. Wasting no time, she pulled up my shirt in the back, dragging her nails up my firm back, causing me to gasp against her neck. I pulled back, smiling wickedly and in one smooth motion pulled my shirt up and over my head, tossing it to the floor of the carriage.

Hers eyes widened, running all over my pale upper body as I sat and smirked. I slowly drew a dagger from my belt, and told her to hold very, very still. I then eased the cool blade between her quivering breasts, and slowly pulled it down, cutting the soft fabric. Her dress began to fall open following the blade, revealing her lacy corset. I sheathed the dagger, gripped the dress, and ripped the torn fabric from her, leaving her sitting panting in her corset and stockings. Her breathing was speeding up, and her cleavage rising and falling with each breath.

I rested my hands on her bare thighs, causing her to shiver again slightly. Leaning in, I slowly slid the flat of my tongue across her heaving chest. Her fingers buried in my hair, I traced the line of flesh along the top of her corset with my tongue, the tip of my just barely brushing the edge of her areolas. At this she gasped, clutching my head to her soft bosom. I smiled, rubbing my cheek against the soft flesh, slowly snaking out my tongue to brush her skin. Rising up again, I softly bit her upper breast, sucking gently, my hands caressing her back.

I ran my hands down her back, slipping them beneath her, and cupping her ass gently. I clutched the soft flesh, leaning up to kiss her gently. Her tongue rushing into my mouth, I sucked on it fiercely, my hands massaging her soft buttocks. I then slowly crouched down, kneeling between her thighs, one smooth, stocking-clad leg resting on each of my shoulders. Lana’s body quivering with anticipation, she spread herself wider, offering her neatly trimmed mound to me. Teasing still, I slowly licked along the line of her hip, watching her leg shake.

Switching sides, I slowly drug my tongue along the line of her other hip. Eyes glued to her glistening pink slit, I leaned in, smiling up at her through my curtain of hair. I slowly spread her lower lips with two fingers, and delicately ran my tongue along the length of her moist cunny. Encouraged by her moans of approval, I began sliding my tongue back and forth across her slit, lightly flicking her clit with the tip of my tongue.

I then pressed my face against her warm crotch, thrusting my tongue deep into her tight, warm crevice. Sucking delicately on her bud, I began working my tongue around inside of her, caressing her tender inner walls. I slowly pulled my tongue out of her warm recess, gently dragging it along the length of her pink slit.

I pulled my face from her crotch, and slowly began to push one finger up into her tight, hot pussy. Kissing her deeply, allowing her to taste herself on my lips and tongue, I curled my finger inside her pussy, stroking her insides. Her writhing and groaning hastened my ministrations, and I began sucking her clit with fervor as I slid my finger in and out of her glistening slit. I then began slowly easing my fingers in and out of her gorgeous hole, being ever gently with her tender flesh. Rising to my knees, I lifted my head from her crotch, and began to quickly untie her restraining corset.

Her own hands rushing to help me, she was quickly sitting nude on the soft seat, panting expectantly. I grinned wickedly as I rose to my feet before her, watching her eyes running across my bare torso, her hands balling into fists in frustration. Her hands quickly wrapped around me, pulling me close. She kissed me passionately, pressing her soft body against mine. I sighed, feeling her firm nipples glide across my bare chest. I sucked fiercely on her writhing tongue as her hands began to fumble with my belt. My pants loosened, her hand quickly snaked inside, gripping a hold of me, causing me to groan into her open mouth.

I stood slowly, my pants crumpling to the floor, and her small hand still stroking me feverishly. Her small pink tongue suddenly flicked out, caressing the head of tip of my cock, leaving it glistening with her saliva. As I sighed in pleasure, her lips quickly wrapped around me, sucking gently. She slid about half of my length into her mouth, her lips stretched wide around my girth. She then pulled her mouth off of me, and began slowly slicking along the length of my shaft, causing it to spasm with each movement of her tongue.

Not being able to take much more of this, I reluctantly pulled away. Seeing the ache in her eyes, I took her hand, pulling her to her feet. I stepped out of the carriage, feeling the cool breeze on my bare, sweating flesh. Looking up at her, I took her hand again, and pulled her out onto the dirt road, my red-hot member brushing her thigh. Then I pushed her up against the side of the carriage, spreading her thighs. Watching her breath speeding up in anticipation, I gripped myself, and slowly ran the head along her wet slit. I gripped her pale right thigh, and lifted her leg up, pressing myself against her moist opening.

Being gentle as could be, I began slowly pushing against her, letting her adjust to the size. Her fingernails digging into my bare back, I slowly pushed my entire length into her, watching her eyes widen with the sensation. Fingers digging into her thigh, I began slowly pulling myself back out of her, savoring each gasp and moan from her mouth. I held her leg up with one hand, my other hand stroking the small of her back. I began thrusting back in and out, but only using the top half of my cock, watching her whimper in frustration. Then I pulled almost all the way out, and then suddenly plunged it all back into her, causing her to arch her back in pleasure, the head of my cock bumping her cervix.

Her nails scratching my back, she clutched me closer as I slid in and out of her tight recesses. Her leg wrapped around my waist, holding me tight as she moaned against my neck. I cupped her ass tightly, ramming into her, feeling her bite my shoulder. Speeding my thrusts up, savoring the sensation of thrusting between her moist lips, I kissed her deeply. Keeping a steady rhythm thrusting, I began licking along the side of her neck, kissing gently.

My tongue ran up the side of her neck, flicking her earlobe. I lightly traced the edge of her ear with the tip of my tongue, moaning quietly. Burying my cock deep inside her, grinding my hips into hers, I gently bit her ear, exhaling my hot breath into her ear with a shaky groan. Her breathing began to speed up even more, her fingernails digging deeper into my back as she groaned. I panted in her ear as I struggled to control myself.

She tensed up, biting my shoulder, nails digging into my back. I groaned into her ear, begging for her to cum. Her body began shaking, spasming, I could feel her muscles squeezing me tightly inside of her. Finally she gasped, body still twitching slightly. I grinned, and flexed my cock inside of her, eliciting another gasp of pleasure. I slowly withdrew myself from her depths, watching my dripping shaft emerge. She whimpered slightly, looking at me questioningly.

I merely smiled at her, and slowly turned her around to face the carriage again. She glanced back over her shoulder at me, and I slowly spread her legs, stroking myself slowly. She groaned in anticipation, bending over, gripping the muddy wheel of the carriage. I gripped a hold of my shaft, and slowly ran the head along her dripping slit, watching her quiver at the delicate touch. With one hand slowly rubbing the small of her back, I gently pushed the tip of my cock into her.

I groaned softly as I tenderly thrust into her, my hands caressing her back lovingly. Gripping her hips, I began slowly sliding in and out of her tight hole, savoring every moment of it. I grinned as I saw her hand snake down her belly to rub her clit as I slid back into her. My thrusts sped up, and her gasps did as well. My eyelids fluttering, I moaned, knowing I couldn’t last long like this, but not caring.

Clutching her soft thighs, I began plunging in and out of her moist pussy. She moaned beneath me, thrusting that luscious ass back against me, driving me deeper. I ran my hands up her body, clutching her soft breasts as I grinded my hips against hers. I slowly grazed my palms across her pert little nipples, enjoying her whimpers of frustration. Feeling my own climax building, I grasped her breasts as I slid in and out, feeling my body tense and shake.

I plunged one last time deep into her, spurting my seed deep inside her. She moaned, writhing against me as I continued to spurt into her. Finally sated, I leaned against her, panting, kissing her shoulders and the back of her neck. She turned her head to the side as I kissed her cheek and asked if her debt was paid. I brushed my lips across hers, pinched her hard nipple, and replied, “Not even close…”

I slowly pulled myself out of her, she gasped lightly at the sensation on her tender flesh. She leaned against me, kissing my bare arm gently. She shivered slightly, and I looked down, seeing my jism trickling down her inner thigh. I took her arm, and began walking down the grassy hill towards the meandering creek. We reached the soft bank, and I began slowly walking out into the water, towing her along behind me.

“Have to clean you up…so I can dirty you again”, I said with a grin. With that, I moved behind her, wrapping my arms behind her. Resting my chin on her shoulder, we sank neck deep into the water. Huddled in each other’s warmth, we sat, and sat.