Chapter Four: Crossdressing

[Webnovel ©Lynnifer Ice]

(Content Warning: Mention of mature themes)

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"Wait a minute... You want a woman to seduce the strongest Alpha, knowing that he is gay?" Azariah stared at her great-great-uncle dumbfounded, "Do you have any idea how messed up that sounds?"

"Hmm," the Guild Master stroked his beard in thought before looking back down at Azariah. "Perhaps it does sound a little crazy, but that is why you are going to pretend that you're a man. It'd be easier to sell the story if you pretend you're a transgender male instead of a pansexual woman. You know, the men born with the female parts."

"Oh my god, Uncle!" Azariah exclaimed, standing up, shaking her head, "That sounds too weird coming from you! For your information, a transgender male is a female to a male without changing physically, which is optional because some do change their body parts. They don't need to be born with it to identify as it."

"Azariah, you turned 28 this year. It shouldn't sound weird at your age," the Guild Master sighed, ignoring her gender lesson. "Although considering I am 107-years-old, I can see where it might be weird. It's a simple plan, though, and you're the best S-Class Assassin in this guild. That's why I am giving you the assignment. If you can't pull it off, then nobody can."

"If I am the best, then why do I need to go undercover and seduce him first?! You know how much I hate their kind! They're the reason the rest of our family is dead! Why can't I just kill him as soon as I see him?!" Azariah shouted, anger coursing through her veins, letting the hatred drip like venom into every word that left her mouth.

"I hope you know you're the only one that yells at me without repercussions, Azariah," the Guild Master sternly said. "It is precisely because of your hatred for them that you need to be the one to do this. You have always wanted to get revenge, and now, here is your chance handed to you on a golden platter! Besides...," he breathed out, "Arcadio Hrodwulf is surrounded by others 24/7 to ensure that he lives. He has many more enemies than just our guild. That is why you need to gain his trust; so that he will let his guard down. If you try to take him out when others are around, and he has his guard up, he or they will surely kill you."

"Uncle... What am I supposed to do about my voice, then? It doesn't exactly sound very masculine. Wouldn't my voice give me away?" Azariah poked, feeling uneasy for once about an assignment.

"Well, you could ask your friends for help. Be sure to take a communications lacrima crystal with you so that you can check in daily with your progress. This assignment could last weeks or months, possibly even years. That is why you must succeed in gaining Hrodwulf's trust. The fastest way is through seduction. People tend to lower their guard and are usually alone when they have sex with another. Another thing, you are to take a herbal remedy each night to ensure that you don't get knocked up. Do you understand," Guild Master Wyett focused on his great-great-niece, needing her to fully understand the risks and nature of the operation.

"I understand...," Azariah sighed. The Guild Master patted her shoulder in reassurance.

"You'll do fine. You have your father's spirit and your mother's cleverness and my skills," he told her with a small smile. "Now, go back to the dorm hall upstairs and ask your friends to help you look and act like a man."

"Yes, Uncle...," Azariah pouted but nodded her head, leaving his company and heading up the east stairs to make her way to the dorm hall. She opened her shared bedroom with her friends and found them still going at it with each other. She rolled her eyes before closing the door with just enough force to make them jump.

"Fuck, Azariah! Why can't you knock like a normal human being?" Candice complained when Yunki and her had to abandon their fuck session as they separated themselves.

"Yeah," Yunki agreed, panting, "Why can't you? We were almost finished! Why are you back so early, though? Did the briefing not go well?"

"The briefing was fine," Azariah gritted as she sat on the edge of her bed. "I just feel pissed off."

"...-because we were having sex without you?" Candice tilted her head before Yunki flicked her forehead. "Ow! What was that for?! I will bite off your dick if you do that again, Yunki," she threatened him while rubbing her forehead.

"You dummy. Azariah is pissed because she has to fraternize with the enemy. You know how much she hates werewolves. Not to mention our guild has been at war with them for well over a century," Yunki scolded Candice before turning his attention back to Azariah. "So, what can we help you with?"

"I have to become a crossdresser for this assignment and pretend I'm a transgender male. So, I need your help," Azariah swallowed her pride as she asked her friends for their help. After all, who else could she ask without it being awkward?

"You want us to get dressed for this, or can we continue being naked?" Yunki shamelessly asked, sounding amused.

"I don't think it matters. You two will just go back at it once I leave," Azariah rolled her eyes.

"Damn straight, we will," Candice laughed, tossing her head back.

"Well, first things first, then, we need to strip you down. There is no way you can leave looking like that. You'll blow your cover the moment those beasts see you," Yunki commented as he hopped off his bed, leaving Candice's side. "Alright, beautiful.~ Let's get to work!" He chuckled as he wiggled his fingers, reaching out for Azariah.

"Don't forget about me!" Candice chimed in, hopping over to Azariah.

"Eh! Whoa, whoa! Not so fast!" Azariah squealed as her friends made short work of her clothes. "Why did you have to take off my undergarments too?!"

"Well, you need to seduce this Alpha, right? So, instead of those gorgeous lace panties, wear some silk boxers," Candice shrugged as she twirled the pair of lace panties around her pointer finger.

"I think she should keep the lace. Lace is attractive whether you have a dick or a vagina or whatever gender you are. At the least, though, you should wear black lace instead of your rainbow collection; black is sexier," Yunki decided, reaching over to Azariah's small dresser. "Oh, and by the way... You may have A-cup breasts, but you'll need to wear a binder," he added.

"A binder? That sounds highly uncomfortable," Azariah deadpanned.

"It can be," Candice agreed.

"Nonetheless, it goes," Yunki commented as he fished out a pair of black lace panties. Then he went to his closet to grab some of his clothes, "You know, it's a good thing we wear the same size, Azariah." He came back over with some clothes, plopping them on her bed while Candice grabbed an extra binder she had from her dresser.

"Is this all really necessary?" Azariah grimaced as Candice wound the binder tightly around Azariah's chest. Yunki just smiled as he slipped the black lace panties onto her, securing them in place at her hips.

"Yes," Candice beamed as she and Yunki began to tug Azariah this way and that as they changed her into a dark-colored oversized long-sleeved shirt to hide her defined curves and a pair of black fitted jeans. A chain belt was hidden under the shirt to keep her pants up and be used as a weapon if necessary. A couple of black combat boots and Candice's black leather jacket finished her outfit.

"You know, it's a pity about your hair...," Yunki sighed as he grabbed a pair of scissors from off their shared desk, "I always loved that it was long - the perfect length to wrap around my hand and pull back. You don't see many male werewolves in this day and age with long hair, though. Just as he reached up and grabbed Azariah's high ponytail, Candice snatched his wrist.

"Now think about what you just said there, Yunki," Candice chided, "You said her hair was the perfect length to wrap around your hand and pull back, right?"

"Yeah, but...," Yunki raised an eyebrow, confused about what Candice was getting at.

"What usually happens after seduction, moron? Sex. Sex happens!" Candice tossed her hands up in the air. Yunki's lips made an o-shape when the realization hit him; he took the scissors away from her hair. "Exactly!" Candice squealed, "What if this Alpha enjoys pulling hair too?! You and I both know she will end up sleeping with him at some point. Let's just give her a man bun!"

"Ugh... Don't remind me," Azariah seethed, loathing the very idea of having to touch the Alpha.

- End of Chapter Four -