Well, maybe at first

"I'll try." The man gasped as he settled between her thighs, but Werner knew that as small and tight as her sex was that his penis was going to tear her open. Christine however was far less experienced in these matters. What little she knew about the maid's role in her first union was that she must bleed upon the man's sword as he stabbed deeply into her. She had nothing to compare it to, but when she felt the hot length of the Verderer's member sandwiched between their bellies, she was pretty sure that this man was above average in both length and girth.

"This may hurt a little, Evelyn." The Verderer murmured as he reached between them to position his manhood against her slit, rubbing it along the slick petals to lubricate the head. After her close escape from Prince Henry, and then again with the bandits in the King's wood, Christine knew that this moment was inevitable; who better to make her a woman than this good man? Not that she had any choice in the matter. By this point all she could do was moan softly and cling to his neck as she waited for the inevitable loss of her maidenhead. The first two times he rocked forward actually felt pretty good as his swollen head pressed against her dripping folds, but on the third thrust it slipped into the entryway of her channel and the pressure of his manhood beginning to fill her made her stiffen in his arms. "My God, you're tight." Werner growled into her ear as he shifted forward to prepare for the next thrust.

Not for the first time the Verderer wondered about this maid and how it came to be that she was wandering alone through the old forest. She was clearly used to a finer life than he, and her father was certainly no common merchant. Some of the most successful merchants lived like nobles and their daughters were as pure and soft as this, but how could a young woman from a family like that end up alone with her brother in the forests? The most likely explanation was that she was fleeing an arranged marriage, that would explain why it was he and not some fat wool merchant that was going to claim this prize.

"I'm a virgin," Christine repeated softly into his ear. "No man has ever touched my naked body, not to mention laying with me like this." Judging by the grip of her pussy around his cock, the Verderer had no reason to doubt her claim. God this was going to be good!

"I know," the Verderer's voice was heavy with excitement, "that's just one of the reasons I couldn't keep away." He rocked forward again, and Christine felt her insides being slowly ripped in two. She was right in her assessment, there is no way that something that big would fit into her delicate body.

"Oww, it hurts." She whimpered, "you're too big." To her relief the Verderer eased back a little, and she could hear the effort in his voice as he softly kissed her temple and whispered encouragement.

"I'm sorry, but I just can't stop now." Christine felt a moment of panic; she didn't want him to stop, just to be a little more gentle. She felt him shift his grip again, grabbing a handful of her hair he tilted her head back so his lips could find hers for a passionate kiss. This position also arched her back and lifted her firm breasts up against his chest, and the combination of sensations from her mouth and nipples made her forget anything else for just a minute. Then, just as the kiss ended, he stabbed deeply in an abrupt thrust, forcing his way into her like an iron wedge splitting into an oak log. The proof of her chastity was shredded as pain exploded from her loins. Thankfully, the way his mouth covered hers swallowed up the sharp scream and even as she felt her inner core stretched open, Christine wondered if he had been clever enough to silence her like this.

"Aiiighh!!" Her next much softer exclamation was as much one of wonder as pain, because although his manhood had torn through her hymen, her young body had somehow stretched to accommodate his girth. Nothing had prepared her for the feeling of being filled like this, she could feel the throbbing inside her where the Verderer's penis had ruptured her maidenhead but although it was painful, the sensation of being stretch open from within was surprisingly fulfilling. Thankfully, after that sudden invasion, Werner stilled his body and let her get accustomed to the feeling as long as he didn't move the pain wasn't bad.

"I'm so sorry, to have to hurt you like that." He murmured, "but it was the best way to do it." In his arms he heard Evelyn sniffle softly, but she seemed to understand, and he began to rock deeper into her tight passage. Each firm thrust brought a whimper or grunt, and he had to cover her mouth with his hand to keep her cries from alerting the boys downstairs. God this felt good! The feeling of her virgin pussy clamped tightly around his cock was unlike any he had ever felt. Knowing that he was the first man to ever breach her like this made the experience even better. "It'll feel good soon, Honey, I promise."

Christine could only hope he was right. In spite of the tender words of encouragement, the Verderer still had his hand firmly over her mouth and gripped her hair even more firmly and pushed as deeply as he could into her petite frame. She could feel the head of his cock bumped into a fleshy wall deep within her, she could only imagine that this must be how a Christmas duck might feel once it had been stuffed with mincemeat. She breathed a soft sigh of relief when he backed out nearly all the way, but then in one long smooth stroke he filled her again. This time, as her back arched upwards her cry of pain was less sharp, and she began to sense a little of the pleasures of the flesh.

"How are you doing?" The Verderer asked lifting his hand from her mouth so she could breathe freely and speak. She knew he had tried to be careful, and now that he was no longer moving the discomfort was bearable. If fact, she felt a womanly satisfaction in knowing she had accommodated a man of his size.

"It's OK," she whispered hoarsely, "just be gentle, please." Werner wished there was even just a little light in the small room so he could see the beautiful woman laid out beneath him, he tried to picture her perfect breasts bobbing with the rhythm of his thrusts, and those clear blue eyes staring at him in wonder as he stretched her open for the first time. To be fair he admitted, other than the orgasm he had given the maid before laying her on her back, most of the pleasure so far had been for him. The Verderer was not an unkind lover, and he resisted the urge to satisfy his burning need by plunging into her again and again. Instead, he reached for Evelyn's hand and drew it down to where their bodies were joined.

"Touch yourself," he ordered her firmly, "rub your clit while I fuck you." Then his free hand slipped behind her knee, and he lifted it almost to her chest as he slowly increased the tempo of his thrusts.

Christine wasn't exactly sure what he meant by clit, but her fingers were soon jilling the folds of her sex in time with his steady rocking. She felt the heat and size of his manhood as it slid past her fingertips, and she wondered idly if all men were this large. The rubbing helped with the discomfort a little, and then there was something else too. A growing need that was becoming as strong as the pain, and slowly her moans changed into gasps of wonder.