The Highwayman of Helmstadt

Slowly at first but quickly draining faster, the dairy disappeared right before our eyes. There weren't any visible holes for the milk to drain out of, so the witch seemed to have been honest about the jug being enchanted. As the very last of the liquid faded away it revealed a small pile of coins sitting at the bottom of the jug. I scooped the coinage out of the vessel and looked it over, astonished by the whole process. The coin looked perfectly legitimate, the witch had made good on her deal.

"Certainly a novel source of income." I mused, idly playing with the coins in my hands. Irma kneeled down next to the jug and started to inspect it, examining the interior as well as the art engraved on the outside. She seemed to be lost in thought while she studied the depiction of the very pregnant female and I remembered that she had said she wanted children eventually. Well it made not have been how she imagined it happening, but in a way I would be giving her what she wanted.

Watching my slave fiddle with the enchanted jug, I started to ponder my long term goals. There was a primal urge deep in my gut that demanded I sire as many children with Irma as possible so I would have to plan around that desire. My simple camp here wouldn't work for raising children so I would need a more permanent structure. Settling in town wasn't an option, it was too close to the city guard and I enjoyed my current freedom from the noble's extortionate taxes and uncaring laws.

What if I had a home out in the woods? Something big enough to house my slave's offspring and give them a place to live and eventually learn my trade. With enough time I could easily sire a loyal band of young brigands all bound to me by blood. The difficult part would be actually building a small homestead, trees would need to be cleared and the home itself would need materials and labor. Perhaps the witch could help me, maybe she had some mystical way to assemble a structure?

Mentally, I shelved the idea away for another time, it was something to think about while I trained Irma and grew used to the idea of dealing with a witch. I still had enough supplies to remain idle for at least a week and I intended to enjoy the down time. My focus turned to Irma again and I caught her attention. "You seem enamored with the art on that jug." Irma was still lost in thought but she looked up at the sound of my voice.

"I uh..." she stammered. "I did want to have a child eventually. I always wondered what it would be like to be a mother." I closed the distance between us and embraced her from behind, murmuring in her ear while I started to grind my crotch into her rotund rump.

"Does it excite you?" I whispered in a deviant tone. "The crude and savage bandit capturing the refined and respected lady of Silverwood manor?" Irma's breathing became heavy and she tried her best to ignore me, though she knew she couldn't escape my probing questions and groping hands. "Maybe you secretly hoped a brigand would capture you and have his way with you, ignoring all the social rules and restrictions of proper courting while he ruthlessly fucked you and finally put your body to use." I emphasized my point by stripping off her simple gown and harshly squeezing her bosom, the resulting streams of milk making it clear that I was already altering her body to fulfill my desires.

Irma whimpered and weakly protested under my assault, halfheartedly trying to deny my accusations but I ignored her pleas for me to stop and kept the pressure going. "Nobility means nothing, you're just a fertile bitch for me to rape and breed as much as I please. Running away won't even be a possibility, I'll keep you constantly pregnant, your belly so fat with my spawn that you'll have to slowly waddle everywhere you go!"

By this point I had worked myself up so much that I simply dropped my trousers and lined my stiff cock up with Irma's wet slit before ramming it in, Irma groaning loudly as I suddenly filled her. I took hold of her wrists, using my grip on her arms as leverage to pull her onto my cock while I started to roughly fuck her, the two of us grunting and gasping while we stood there naked in the middle of the camp. Lewd slapping sounds filled the air as I thrust away at her, pounding her asscheeks like a fat drum.

My climax started to speedily approach so I grabbed her shoulders and held her in place, managing a few last desperate humps to try and work my dick as deep into her passage as possible before I blew. "You're just my personal breeding slave now!" I snorted out in a lust-fueled frenzy. "Get pregnant you arrogant slut!" I came hard, moaning as my prick throbbed and shot jets of seed directly into Irma's womb, filling her to the brim with warm sticky cum. Irma seemed to fight it but then shuddered and loosed an animalistic groan, orgasm hitting her when her tight cunt felt my rod pulse and release a satisfying heat deep inside her.

Irma went limp after she came but I continued to hold her up while I felt my balls dump their very last reserves into her receptive hole. When I felt I had gotten as much into her as I could, I awkwardly walked us over to my bedroll and laid her face down, laying on top of her soft and pliant backside. She was knocked out cold, the intense copulation and rough climax too much for her to handle. I took a few moments to enjoy the afterglow, but as I fondled her sleeping form my flagging staff started to grow erect again in her snug tunnel.

I gave Irma's colossal rump a few good smacks but she didn't wake, her light snoring letting me know she was going to be out for a good while longer. "Can't get away from me that easy." I mused aloud. "Sleep all you want slave, your ass is still mine." Fully aroused again, I set to work on Irma's sleeping pussy, maintaining a slow and steady rhythm until I couldn't hold out. Sighing with satisfaction, I pumped a second load into my royal slave before laying atop her once more and finally succumbing to sleep myself.

When I woke in the morning I was still lazily laying on my patrician plaything. She made for an excellent mattress with her inviting and pliant curves. Eventually I rose from the bedroll and dressed in my usual trousers and padded gambeson, the light armor offering some protection without sacrificing mobility. I woke Irma with a hearty slap on her full bottom, snickering mischievously as she woke and remembered the fierce pounding I had given her last night. "Wake up breeding slave," I taunted her, "it's time for breakfast so hurry up and get to work."

Yawning and bleary-eyed, Irma donned her peasant gown and prepared our meals while I used my whetstone and tended to my weapons. When breakfast was prepared we sat down to eat and Irma decided to use the time to start a conversation.

"This isn't something I ever wished for." I gave her a fearsome look and she quickly corrected herself. "I'm sorry, this isn't my fantasy, Lord Gilbert." Her tone was a little sarcastic but I wanted to hear what silly thing she had to say this time, so I let it be. "My fantasy was a worthy suitor proving to me that he was a kind, goodhearted, honest and strong man. A smart and handsome gentleman that would accept I was more than capable of continuing to rule my manor." She scowled at me when I snorted contemptuously and laughed at her prim and proper scenario.

"I don't believe you." I told her, enjoying the way her scowl transformed into an offended glower. Annoying the upright and noble Lady of Silverwood manor never ceased to amuse me and I was almost hopeful she would retain some of her highborn arrogance since fucking it out of her felt so damn gratifying. "You might pretend that's what you want, but you're lying to yourself." She opened her mouth to counter, but I cut her off. "You sat there for years, I'm willing to bet, waiting for your imaginary perfect match. Deep down though, you knew nobody would ever meet your requirements and so you hoped someone strong and powerful would come take you by force and save you from the prison you had confined yourself in."

Irma was stunned for a heartbeat or two, serious contemplation and self-doubt evident on her face before she regained her composure and cleared her throat, adopting a dismissive attitude.

"Well, I'm sure a sniveling criminal and lowlife would think something like that, trying to justify his actions." I chortled again and followed up with an observation.

"You've cum every time I've had my way with you. You can lie to yourself all day, but your body is honest about what you really want. You haven't even tried to run away since the first time I pinned you down and had my way with you."

"Yuck," Irma grimaced and made a disgusted noise, "you know that's because I can't hope to outrun you. I don't care at all for your horrid and brutish animal advances, you knave."

"If that were the case, you'd fight and struggle even if it meant dying." I told her coldly. "I once ambushed a peasant woman on the road that was taking her crop to Helmstadt. Even with my dagger at her throat, she still screamed and kicked and punched when I took her body as a toll for using my road. The thought of death didn't stop her from struggling and fighting. I admired her tenacity so much that I let her go after I filled her womb with my seed. The strong do what they please and the weak obey or die. You're not willing to die, so you've already given up and accepted that your servitude is the price you pay for life."

"You talk an awful lot for a lowly brigand." Irma huffed, crossing her arms and pouting like a young village girl.

"My mother stole books and taught me to read speak properly." I answered flatly. "Your mind and your tongue have to be as sharp as your blades if you want to fight for a place at the top." Irma stayed silent, clearly not interested in continuing the discussion but I knew she was still listening. "Disagree with me all you want, it won't change reality. You're the bottom bitch of our little two person gang and your body's already figured that out.

That's why you cum every time I fuck you. Your body knows that its purpose is to take the seed of a strong male and bear his children. Soon enough your belly will swell with my spawn, your tits and ass will grow and your body will do everything it can to be as feminine as possible to appeal to the dominant male."

"You're sick." Irma gagged, the few words containing an impressive amount of scorn. I just laughed again, knowing that I would be proven right as time went on and I kept inseminating her.

"Well," I stood and faced her, "since you have such a low opinion of me already, I may as well enjoy myself." I advanced on Irma, my wolfish grin and rapacious stare already very familiar to her.

"No no no, stop! Please! I told you, I don't want this!" Irma protested and reflexively stepped back but made no real effort to escape my clutches. In no time at all, I had her on her back in my bedroll with my iron-hard shaft shoved deep inside her. She made wonderful noises as I hammered away at her depths, her halfhearted complaints turning to excited moans with each stroke of my shaft. With one hand I started to tease and toy with her clit, her voice going up an octave when I touched the little nub of flesh.

She was nearing the edge already, her blubbering protests and ragged gasps making it hard to understand her, but she stammered out her thoughts nonetheless.

"F-fuck no please! I don't want to cum! I'm not a slu- ah, mmm... Fuck! I'm not a slut! God, please don't cum in me anymore, I don't want a nasty bandit's baby growing in my womb! I'm supposed to be the Lady of ah... Silverwoo-" She cut off with a cry of pleasure, her orgasm interrupting her when I buried my throbbing cock in her tired cunt and filled it with my hot, thick cum. She howled in ecstasy and her greedy pussy squeezed and massaged my lance as if to coax out every last drop of semen. Irma might say otherwise, but her body knew its purpose was to submit to me, take my seed and reproduce.

When I was sure I had pumped the very last of my pearly ropes into her fertile and receptive womanly tunnel, I stood and took a moment to inspect my handiwork. Irma was in a daze, her expression a mix of conflicted contentment and exhaustion. Shining white in the sun, a thin stream of the overflowing amount of cum I stuffed her with dripped from her lower lips. Her heavy tits heaved as she took deep breaths of air. Primal and predatory, something from deep in my gut told me that this is how a woman should be.

She should be naked, out of breath and utterly satisfied. Her sex filled with my either my seed or progeny. Her entire being subservient to my desires and all of her energy devoted to pleasing me and producing my offspring. The rush of dark thoughts made me heady with power and lust and I retreated to my favorite stump, honing my already razor-sharp blades until I calmed down and re-balanced myself. Cruelty and viciousness were powerful and useful tools, but they were best utilized in precise, measured amounts. Still, the temptation to give in lingered; spend the whole week rutting her, frantically mate her like a crazed animal and don't give her even a second of peace until she had a visible baby bump. No, I would remain composed and reserved. Careful and calculating, as a skilled brigand should be.

I spent the whole rest of the week fucking Irma's brains out, never letting up or slowing down. I would take her while she cooked and cleaned, mate with her when we bathed in the nearby stream, ravage her senseless until we passed out and slept. From morning until night, I kept her pussy stuffed with my stiff erection, regardless of if she begged for mercy or screamed for more. Finally at the end of the week I gave her a break and let her sleep in, free of molestation. By now I was sure that she knew her place, that her role was to serve me. When she woke and discovered that I had let her sleep in and wasn't balls deep in her snatch, she looked both relieved and disappointed. She cooked breakfast without direction or complaint and we ate silently for a time before she addressed me.

"You win." She almost whispered. She looked at me to check if I was listening and continued louder and more confidently when she saw I was. "I give up. I'm done fighting and surrendering feels too good." She sighed dejectedly and smiled sadly, placing a hand on her stomach. "At least I'll finally get to be a mother. Maybe I really would have never gotten pregnant if not for you."

"Good." I replied curtly, nodding when she looked up at me. "Behave well today and I might get you a gift." Irma looked quizzically at me, but I didn't elaborate. After breakfast, I sat and freed my penis from its prison, looking expectantly at Irma as it throbbed and pulsed with need. Without complaint or hesitation, Irma approached and stuffed it into her mouth, methodically bobbing up and down as she slobbered on my cock.

She may not have been the most enthusiastic cocksucker, but she didn't resist when I grabbed her head and pulled her down on my dick. The pleasure was too much and I came hard and fast, Irma gulping and swallowing obediently as I sprayed cum down her throat. She pulled her lips off my sausage slowly, cleaning my spear before she swallowed one last time and smacked her lips and exhaled.

"Good work, slave." I commented, groping her clothed bosom for good measure. Irma nodded and returned to her chores, wiping her mouth with her arm. I gathered my equipment and prepared the horse I had stolen, intending to lay an ambush on the road once again. When everything was sorted, I pulled Irma away from her tasks and bound her hands together with rope before leashing her to the horse. "Today's a test," I told her as I secured her bindings, "we're going to the road, but this time I'm not going to gag you. Follow my rules, do what I say and you'll get a nice reward."

"Yes, my lord." She meekly answered and I mounted my steed before setting off at a reasonable pace, Irma walking along beside me. When we reached the road I immediately returned to my favored spot behind the old oak, anchoring Irma's restraints to one of its sturdy gnarled roots so she couldn't simply run off at the first sign of trouble. The hardest part of being a highwayman was sometimes the incredible boredom that would set in when waiting for prey to come down the path, but this time I was prepared.

The time ticked by as we waited and I entertained myself by harrying Irma, grasping and bouncing her sizable rack, groping her inviting rear and playing with her however I pleased. She would struggle and fight to keep her voice down until a gasp would squeak out of her mouth and I would shush her sternly before continuing to paw at her voluptous curves. Hours passed until the sounds of a lone person walking down the road reached our ears. I tweaked Irma's nipple one last time for good luck before we both froze and peeked around the old oak to spy on the traveler.

A pretty young woman was strolling along the road, a sizable satchel slung over her shoulder. She was fair skinned as was typical for northerners, though she lacked the sun-kissed tan of a peasant and the porcelain white pale of a noblewoman. Her golden blonde hair was in a long braided ponytail, swaying gently as she walked. Her figure was mostly hidden by the clothes she wore, a simple but elegant short dress along with good quality leggings.

She was certainly middle class, possibly a merchant or even a burgher member of the local government. She was the perfect prey. I moved out onto the road, shortsword and dagger in hand as I blocked the young woman's path. She halted immediately, her hands reflexively clutching her satchel. Perhaps she had something quite valuable in there, expensive trade goods or maybe important documents. Frozen in place, she made no attempt to run as my long easy strides brought me face to face with her and I recited my usual line.

"There's a toll to use this road." The young woman's anxiety shifted to annoyance and she fired back at me.

"There's no toll on merchants entering Helmstadt, the baron repealed all of them two years ago." Low ugly laughter rolled from my lips and I took a step toward her, my menacing stance making her shy away.

"I don't work for the baron. I don't work for anyone. You used my road, now you owe me payment." The young lady nearly caught me off guard when she pulled a knife from her satchel and swung wildly at me. My reflexes were fast enough that I avoided the worst of the strike and her blade slashed harmlessly across my gambeson until it grazed my left cheek, the shallow cut far from critical but still stinging with pain. She kept flailing frantically, she was no duelist but her unpredictable attacks kept me on the defensive.

An opening presented itself when she swung too hard and overextended her arm, her wide miss leaving her vulnerable. I delivered a swift kick to her midsection and she doubled over in pain, dropping the knife which I kicked away. Losing no time, I bound her hands and feet and dragged her behind the old oak, the huge tree granting me some concealment while I caught my breath. Irma was still there, wide-eyed at the sight of my new captive and the wound on my cheek.

"You're hurt." She stated with some concern, watching as I held a bandage to the minor wound and staunched the light bleeding.

"It's fine, nothing serious." I reassured her. "You didn't give me away, so you're doing well so far. Keep your eyes and ears open for anyone else showing up on the road." With my sentry set, I rifled through my defeated opponent's bag. There were small glass jars of various herbs and spices, along with papers detailing orders from customers. My assumption was true, she was a merchant managing a small but profitable spice trade. There was also a rather fancy hand mirror in her bag, along with a pair of leather hair ties. All things considered, I was quite pleased with the haul, though I still had a subdued young lady to deal with.