Harem Overlord: I ALWAYS Finish Quick!-Chapter 107 Being Anal About It [R-18]

**WARNING: If you felt ANY discomfort from the last chapter... better turn off the novel now.**

**You've Been Warned**

Ryan smirked as he saw the frightened servant kneeling in front of him. Walking over, he bent down, placing his hands around Tammy's neck, choking her with all his strength.

The young blonde squirmed against his hold and struggled to get free but was too weak to fight him.

Tammy whimpered, clutching at her throat, feeling her life gradually slipping away with each passing second.

"Are you ready to answer my questions?" Ryan asked.

"I. . . don't know. . . what you want me. . . to say," Tammy panted, unable to breathe correctly under such a tight grip. "Plea-se," she cried out in desperation as she began losing consciousness from lack of oxygen.

Ryan loosened his grip and placed a finger on the woman's lips to silence her before moving his free hand down between her legs until it touched the opening of her ass.

Tammy moaned into her hand, tears welling in her eyes, when the tip of his finger found her tiny hole and pressed hard enough for it to go inside.

She couldn't help herself anymore and released a muffled scream, gurgling noises escaping her mouth.

Ryan gave her ass another little push. Then two fingers slipped deep inside. "Answer my question, or your suffering will continue," he threatened before pressing his thumb on the clenched muscle above her anus, causing her asshole to loosen just enough for him to put three of his fingers inside her back passage.

"Ooooh! Nooooo!" the blonde whined, pushing her hips backward to feel more Ryan's fingers inside her.

"Whore, are you enjoying this? Maybe I should fuck you harder so you remember this lesson," Ryan growled as he worked his digits deeper and deeper inside her ravaged body until all five were buried within her guts.

Tammy gasped with every thrust and cried in agony as her ass became fuller with each penetration. The pain was unbearable, but it was also turning her on even more than before.

She wanted to beg him to stop hurting her, but instead bit down on her own arm to keep silent, hoping she would be able to endure the punishment a little longer if it meant having another orgasm.

"Who are you, really?" Ryan asked, twisting his fingers inside the woman's ass. "What relationship do you have with the human empire?"

Tammy could only grunt and cry out while trying to think of how best to answer his questions without being killed by the man who seemed hell-bent on fucking her ass until it turned into an open wound.

"Answer me or suffer," he said, fingers twisting around each other inside her anus like an accordion.

"I... I don't know," Tammy moaned, squeezing her eyes shut as the pleasure grew more powerful than any pain ever experienced before.

She couldn't believe this was happening. Subject one was only supposed to be F-Rank!

This man was not F-Rank and clearly knew more than he was meant to.

Although she was only an F-Rank, she had an A-Ranked specialty in covert operations that allowed her to go undetected even from C-Ranks! But she got cocky and saw an opening when the Duchess left.

She regretted joining the military. When she first joined, there had been promises of great rewards, but all she got was stuck on an assignment watching an F-Rank.

Yet when she thought about rewards, Tammy thought she'd rather be loyal to the man who had his fist deep inside her ass, as that was all the reward she could ever ask for.

What she felt between her legs was beyond anything she had ever known.

"If I tell you everything I can, will you... leave my ass alone?" Tammy begged, wanting to take advantage of the situation as much as possible.

"Maybe," he replied, his hand still buried in her bowels.

"Fine." Tammy sighed and took a deep breath through her nose. "They told me to follow you, and I saw an opening once the Duchess left."

Ryan pulled his fingers out with a slurping sound and then shoved them back inside, causing the woman to scream out with another muffled whimper from the intense painful pleasure.

"That's all?" Ryan asked. He reached into the woman's ass and grabbed something hard. 𝘧𝓇𝒆𝗲𝓌𝙚𝙗𝓷o𝘷𝒆𝘭.𝐜𝚘𝒎

"P-Please!" Tammy cried, tears rolling down her cheeks while trying not to shatter into pieces from pure ecstasy at what was happening between her legs.

She didn't understand why she felt this way or how he could make her feel this good. She only knew for sure that she wanted more than ever before.

"I thought you were supposed to be trained by Dr. Rubenstein," he continued as he held his fist inside her hole, waiting for her body to relax enough to pull out his fingers. "Why would the grand empress send someone untrained on a mission like this? That doesn't make sense..."

"I... I don't know! Please don't take your hand out yet! Don't stop! Oh, fuck! I'm so close!" Tammy moaned, biting onto her arm to keep silent instead of begging him to go faster.

The pain was lessening now but replaced with pleasure so strong that she couldn't believe anything else existed besides herself and her ass being fucked.

"If you want me to continue, you'll need to answer my questions properly."

Tammy gasped n bliss when Ryan began moving his fingers back and forth. "Oohhh yes," the blonde whimpered, squeezing her eyes shut.

"What is the human empire's purpose in brainwashing me?" he asked.

"I-I d-don't kn-know," Tammy stammered, closing her eyes as she moved her hips back against him.

"Then don't expect to be rewarded," Ryan said as he pulled out his hand from her ass, leaving behind a blazing trail where they had been inside. He grabbed hold of her ponytail again and yanked it forcefully until her face pointed toward his groin.

The woman coughed painfully at this sudden movement making Ryan smirk. He slapped the young woman's cheek several times before finally letting go and looking down at the bruises already beginning to form on the woman's flesh.

"Tell me what the grand empress's plan is!" he demanded, grabbing her chin. His fingers dug into her skin hard enough for her to cry out in pain, but he didn't care. "Or I won't let you off with a simple punishment."

Tammy gagged and bit her lips so she wouldn't scream too loudly. She needed every ounce of strength to keep herself alive and not spill any information that would lead him to Dr. Rubenstein or the grand empress.

Tammy closed her eyes tight as tears welled up in them while trying desperately to think about something other than being fucked by that man who seemed like a god with how his hand felt between her legs.

It was all she could do not to pass out right there and then, giving away everything she knew because that's precisely how good he was feeling.

"Tell me," he continued, pressing his thumb on her clit, causing the blonde's body to shiver.

"Oohhh," Tammy moaned softly, still refusing to speak even though the sharp slap across her cheek caused her vision to blur and blood to drip from her mouth. "Plea-se," she whispered through bloody lips. "Don't... Don't make m-me d-do th-this..."

"Who is Dr. Rubenstein?" Ryan asked, massaging her sore face until it turned back to its original color as he ensured he had hurt her enough for her mind to start thinking properly again.

"A g-great h-healer wh-who c-can help us t-t-turn f-f-fools into p-p-princes!" Tammy replied in a hoarse voice while keeping her eyes closed tight.

"A great healer?!" Ryan repeated in shock before smacking her on the nose and forcing open the woman's eyelids with his fingers so she couldn't hide behind closed eyes. "That's all you have to say?! Do you think I'm some fool?"

"I kn-know you're not a fool! I just don't wan-nt to d-d-die yet," the blonde stammered, finally opening her eyes to look at him, but quickly shut them when he grabbed her ponytail again.

The man was clearly furious, which was strange because he didn't usually show anger toward others.

His gaze was cold and scary as he looked at her with menacing dark green eyes.

"What is the empire's purpose with me?" Ryan demanded, still gripping Tammy's hair as hard as he could, pulling it forcefully, causing her head to turn left and right.

Tammy gasped each time her neck got yanked from side to side. It felt like a fire raged between her shoulders.

She struggled to hold herself upright against the pain. Her arms trembled uncontrollably from being pulled around by such an unfamiliar feeling of helplessness.

"W-W-What do you want me t-t-to d-d-do?!" she begged, tears already streaming down her face once more for how painful everything seemed. "They'll kill me. I can't tell you anything!" she whimpered, realizing that she only wanted this all to stop. She knew there would be plenty more for her later if she continued to live.

"If you tell me, I can help you live," Ryan said as he reached down and gripped the young woman's hand, squeezing tightly enough that his fingers dug into the soft skin of her palm and began cutting off blood flow into her hands and feet. He wasn't going to allow any chance of her escaping in case she tried something funny or betrayed him somehow.

The blonde cried out in agony as blood rushed through her body in a wild torrent so strong that it made her feel lightheaded and dizzy with pleasure.

"I-I w-w-w-will t-tell y-y-you everyth-thing," Tammy promised, gritting her teeth hard enough to crack them, but not before he squeezed too hard and caused the pain to worsen even further. She could barely speak due to the pain rippling throughout her body, but the words were still loud and clear. "B-But I n-need an oath," the blonde stammered. "A heavenly oath..." she added when she saw the man about to release his grip on her hand. "Swear... swear that you will h-help me live if I tell you."

"Fine." Swearing the oath, Ryan waited for the girl to speak.