The Highwayman of Helmstadt

"Gag her while I get a better look at the rest of her goods." While my slave reluctantly did as I asked, I stripped the young merchant of her clothes. She started to recover from the blow I had dealt her and struggled helplessly against her restraints, her shouting muffled by the cloth Irma had gagged her with. The removal of the merchant's dress and leggings revealed a healthy youthful body, her bosom and hindquarters both a respectable size and her muscles were lightly toned.

"Not bad. I prefer a curvy, plush, properly female build like yours Irma, but she has her own appeal." Irma examined the squirming captive merchant for a short time before beseeching me.

"Lord Gilbert, do you really have to... be with her? You've already taken her wares and you can always lay with me." I shook my head, grinning cruelly as I disrobed and presented my growing erection to the two unfortunate women.

"The strong do what they wish Irma, I would have thought you'd have taken that to heart by now. Consider this another lesson." The young merchant's eyes went wide as I knelt over her naked form and started to rub my engorged penis against her slick pussy, her muffled shouts slowly turning to reluctantly aroused moans. "Not putting a nubile young woman like this to good use would be a terrible waste." I told my prisoners, relishing the fact that Irma was going to witness a demonstration of my virility.

"Good thing she wandered down my little part of the road, who knows how long she might have gone without a proper breeding? Fortunately she'll be leaving here with my bastard planted in her and her womanhood put to good use." Irma and the merchant both watched in suspense as I slowly drove my shaft and glans into the young woman's cunt, pushing deeper and deeper until I had totally filled her tight hole.

Fully lodged in my prey, I turned my attention to Irma and pulled her close so I could lock her in a savage kiss. She closed her eyes and submitted to my advances, letting me do as I wished until I broke the embrace, both of us gasping for air. "Remove her gag." I told Irma. "Feed her some of your milk. Give her a taste of what her body will produce when I'm done with her." My fallen noblewoman did as I asked, removing the merchant's gag and stuffing her mouth with a nipple before she could even start to protest. I reached over and squeezed Irma's udder and forced milk into the young lady's mouth, filling her cheeks until she finally relented and started to swallow the nourishing drink.

The sight of my slave breastfeeding another beautiful woman stoked my already burning passion and I started to thrust in and out of the trader's tight tunnel, stuffing her lower lips while my slave filled her upper ones. Irma seemed to enjoy the unwilling attention on her nipples and started to masturbate, her fingers working frantically at her moist sex. The profane show excited me even further and I began to fuck the unlucky trader at a brutal pace, battering the poor young woman's pelvis with my crotch.

The deviant show Irma was performing for me combined with the exquisite pleasure from ravaging the captive merchant swiftly drove me to my limit and I held out for a few last desperate thrusts before it was too much for me. I wrapped my arms around the prone trader and took greedy grasps of her ass, using the leverage to drive my phallus as deep into her vulnerable vulva as possible. I shook with pleasure and howled in ecstasy as I came, my sack and rod pulsing and throbbing as they blasted my cum into her uterus and conquered her very core.

Irma came shortly after me, shuddering and moaning as she brought herself to climax, her tit still shoved in the young woman's mouth. I laid on my captive and relaxed momentarily, kissing Irma when she crawled to me and sought intimacy in her afterglow. The captive trader shook as she came, laying still and panting as we all recovered from the odd threesome, her stamina or willpower had evidently been drained by the ordeal. When I felt sufficiently rested I withdrew from the young lady's well-bred pussy and shoved my groin in Irma's face until she got the hint and sucked my manhood clean.

My work here was concluded and I had Irma load the merchant's satchel onto my horse while I dressed. I threw the despoiled merchant's clothes on her tired, disheveled mass and gave her a parting speech. "Good try, but you had no chance against a stronger opponent. Shame I won't be around to see you get nice and pregnant with my bastard. Once you birth that one, you know where to go if you want another." I laughed maliciously as I walked away, mounting my horse and collecting Irma before heading back to my camp.

Leaving the menial task of storing the rest of the stolen goods to Irma, I took the hand mirror and hair ties I had pilfered and made sure they were in good condition. They were still of good quality so I surprised Irma and presented them to her, explaining when she gave me a quizzical expression. "I told you I'd give you a gift if you behaved, so here you are."

"This is... thank you Lord Gilbert." She accepted the gifts, hurrying off to the fireplace to sit and preen herself. I followed and sat behind her, running my hands through her long raven hair. She seemed to stiffen up at first, unsure what exactly I was doing but she relaxed when I began to fashion her beautiful hair into two long braided pigtails, a traditional hairstyle worn by northerner women.

"You know how to braid? Irma asked incredulously.

"My mother taught me when I was very young." I told her, the feel of her soft hair and the meticulous task putting me at ease. "It was one of the ways I could care for her, repay her in a small way for all the things she did for me."

"Do you miss her?"

"Yes." We spoke no more, a comfortable silence setting in until I finished, Irma handing me the leather hair ties to secure the strands of braided hair. She was incredibly alluring with the new hairstyle, the long black braids tempting me to grab them and pull as I pushed her down and had my way, but there would be time for that later.

"You have quite the divided nature," Irma observed, "you're clearly not a good man, but you're capable of gentleness." I snorted in amusement at her comment.

"Yes, only a gentleman would attack that lone woman on the road and force her to take his seed. Don't get any delusions, I'm treating you well because you've pleased me and been obedient, not out of some misguided moral obligation. I have no reason to punish a loyal and useful slave." After that there was no more discussion and we retired to my bedroll, a new day greeting us in the morning.

Finished with breakfast, I approached the magic jug the witch had given us and drew one of my daggers. A quick prick of my finger yielded a few drops of blood that fell into the silver vase and drained away. That familiar feeling of discomfort grew and within minutes the witch strode out of the trees and into my encampment, her ever-present smirk still as disquieting as the first time I met her.

"You have need of me, Lord Gilbert?" The sorceress asked, her voice rife with amusement as if I were the most entertaining thing in the entire realm.

"I do, witch. I need a more permanent home that will have room for my many children, as I intend to keep my slave permanently pregnant. I'm willing to pay if you have some means of clearing an area in the woods and building a good sized hovel to hold my wealth, slaves and spawn." The enchantress rubbed her chin as she considered my request, cackling gleefully when she came to a decision.

"This can be done, though it will take some effort from my coven. We will happily give you your bandit lair, but in return we ask that you give us an apprentice."

"How will I do that?" I asked. "Do you want to me kidnap a traveler on the road and press them into your service?" She cackled again, laughing as if I had told her quite the jest.

"You have already done so, Gilbert. The unlucky tradeswoman you left ravaged and defenseless near the road will make for a fine student." She grinned uncomfortably wide and almost whispered in a conspiratorial tone. "After all, she is already broken and bred. The perfect clay to mold and shape however we wish. Now, wait three days and then head across the road and into the forest. One day from the road you will find your new haven." With the deal done, the witch walked away and vanished into the woods.

Time flowed rapidly like a river, Irma and I packing my stolen wealth and supplies and preparing to move. There was some minor trepidation on my part, but so far the witch had been fair in her dealings and I was excited to live in an actual home again. Living in a rough camp for most of my life had hardened and tempered me like a fine sword, but I needed space if I was going to raise multiple brats into a criminal band.

Any time I had available while packing I spent dominating Irma, often shoving her down to the ground and pulling on her pigtails while I impaled her on my spear and drowned her womb in warm spunk. Three days passed and just as the witch instructed we set out to the road, crossing it and heading into the forest. We wandered for a day after that, blindly stumbling into a large clearing just as we started to wonder if the sorceress had tricked us.

We were greeted by a modest but good sized dwelling, its sturdy wooden walls flanked by open earth that would be perfect for gardening. Exploring the inside of the small manor revealed a large master bedroom, a kitchen and dining hall, a nursery, and a number of smaller bedrooms. We took some time to unpack and settle in and I was looking forward to sleeping in the huge bed that stood prominently in the master bedroom.

I was quick to lay out new tasks for Irma, it would be her job to cook, clean, and manage the garden while I continued my banditry and fleeced any travelers foolish enough to come down the road without sufficient protection. The first day I left for the road and left Irma alone at the manor, I actually hid nearby and watched, waiting to see if Irma would try to run and escape her servitude. My efforts in training her paid off however, and she happily went about her duties, maintaining the home and beginning a simple garden with herb seeds that I had purchased at some point from the witch.

When the evening came and I was certain she was committed to her new role as my faithful servant and personal cum receptacle I gave her back the fine red dress she was wearing when I had first caught her. Of course, I had made a few small modifications to the dress, making strategically placed cuts that left her breasts, rear, and crotch exposed when she wore it. She was quite grateful to have it back, even with the adjustments I had made to it. She looked incredible in the fine regalia with her femininity on display, open and accessible for me to take advantage of whenever I pleased.

Days faded into months and Irma's suggestive clothing combined with my ravenous sexual appetite resulted in her belly starting to show an obvious baby bump. Finally my efforts were bearing fruit, my slave was pregnant with my child! Watching her move about the home, her belly swelling with my child, her breasts leaking delicious milk, her whole body conquered and transformed by my advances, it all drove me wild with desire.

I would often ambush her in the kitchen while she was preparing a meal or cleaning and catch her in my grasp, trapping her in my embrace while I groped at her heavy tits and pressed my groin into her well-cushioned bottom. The holes in her dress would prove to be very useful, as all I had to do was drop my trousers and then there was nothing between my rapacious rod and her pregnant pussy. I would move her against a table and she would bend over and brace herself on the wood while I penetrated her from behind, both of us moaning with delight as I filled her greedy snatch with my throbbing erection.

"Well? Are you happy?" I interrogated her as I thrust back and forth into her tight sex. "Finally a strong male to mate you and fill your belly with his children, putting your womb to use and fulfilling your purpose?"

"Fuck, yes!" Irma gasped. "I submit! To hell with nobility, I don't care anymore! Dominate me! Fuck me, cum in me, breed me! Give me more children than I can count and keep me permanently knocked up!" I grinned devilishly at her surrender, she had truly realized that she was happier with me dictating her life and breeding her properly.

"Good slave." I muttered in her ear. "You'll get what you want. I'll keep you endlessly pregnant, your womb permanently occupied. You'll bear a whole army of brigand bastards for me!" We both cried out as I carefully grabbed her gravid middle and used the leverage to drive my turgid cock as far into her depths as it would go. We howled and crooned as we both climaxed, Irma's already impregnated womb still greedily squeezing and milking my shaft for every last spurt of male essence.

Giving her fat rump a playful slap, I withdrew from her snug embrace and left her to continue her duties while I went to maintain my weapons and armor, enjoying my post-orgasm high and the relative solitude my bandit outpost provided.

The days and nights kept rolling on until a knock at the front door roused me out of my meditative state while I was working on my shortsword. Warily, I approached the door with my blade in hand and opened it slowly. The witch stood there, her signature grin still as unsettling as ever. I relaxed very slightly, enough to lower my weapon and the witch's grin grew; she was clearly amused when others found her frightening or off-putting.

"Hello again, Lord Gilbert." She expertly curtsied, her form impeccable but her tone still irreverent. "Our relationship has been nothing but beneficial and I come to offer you a gift."

"Really? A gift?" I asked somewhat incredulously. The witch simply maintained her unnatural smile and continued to speak.

"Your slave will give birth today. I can ensure this and every last one of her births will go smoothly and without complication." For the first time ever, I watched her smile fade into a cold and detached neutral expression. "This will be a gift, no payment needed, no tricks or malicious deceit. My coven and I offer this freely to show our appreciation of our dealings." She smiled again and I almost found the familiar expression comforting after witnessing her almost deathly neutral lack of emotion.

Thinking better of refusing a sorceress, I accepted her offer. "Excellent." She purred as she strode confidently into my home, heading straight for the kitchen. I followed cautiously, noting that the witch had perfectly measured steps and made almost no noise as she went. Irma was busy in the kitchen and noticed us enter, giving me a questioning look when she saw the witch.

"She says you will give birth soon." I explained, Irma nodding her head in understanding.

"I could feel it." Irma mentioned. "Little kicks here and there. I'm not surprised today is the day."

"She says she can make this birth and any others go without complications." I elaborated as the witch drew closer to Irma.

"If you would please remove your clothing?" The witch asked Irma, smiling when my slave looked to me for confirmation.

"Strip." I ordered, and Irma did so, revealing her gravid middle and swollen breasts. The witch reached out and placed a hand on Irma's abdomen, seeming to examine it before nodding to herself. Producing a small glass vial, she poured its contents down Irma's throat before she could even protest, holding her mouth and nose shut until she swallowed.

Irma opened her mouth to complain, but the sorceress shushed her and pulled another item from her cloak. In her hand was a small golden box and she lifted the top, the vessel's lid opening on delicate little hinges. She plunged her index finger into the ornate container and when she pulled it out it was covered in a vivid red substance that looked to have a paste-like consistency and texture. The witch began to use this red mixture to paint an intricate and indecipherable symbol on Irma's belly, a vaguely geometric shape beginning to take form on her soft skin.

The process took a few minutes but the witch finished and put away her golden box before wiping her finger on her cloak and stepping back to inspect her work.

"The ritual is done." The witch spoke, commanding Irma and I's attention. "From now on her births will be free of trouble." She turned to me and smiled again. "She may also be slightly more fertile. Do not be surprised if you find your dream of a small army of descendants coming true." With her business done, the witch quickly left, politely shutting the front door behind her as she went.

Later in the day, Irma went into labor and I attended her as she gave birth to beautiful twin girls, joyful tears filling her eyes as I held them with her. We named them Katrin and Irene, and I had no doubt they would grow up to have their mother's beauty and their father's determination. Privately, I swore to myself that I would teach them to fight, teach them how to survive in the cruel world, how to struggle and clash until they reached the top of the food chain.

Someday they would accomplish great things and I would watch them claw out a great fortune from life's iron grip. Until then, I had a devoted slave that was eager to bear me as many heirs as possible. I smiled as I watched Irma beam happily, elation and pride clear in her face. She was still as beautiful as ever and a familiar urge to breed her welled in my gut. My daughters were destined for great things, but I was going to make sure they had plenty of sibling competition.