Jessica fucking the man slowly, with deep, accurate thrusts as she held his hips; Katrina standing behind her, both hands cupping the younger girl's breasts from behind and massaging her nipples, and her own cock pushing at the crotch of her jumpsuit.
Chapter Four: Deflowering a Virgin
Katrina was changing in the next room when there was a timid knock on the door.
“Enter,” she ordered.
The door slid open and a petite strawberry blonde girl entered the room, her hands behind her back. “Miss Katrina, my name is Jessica Chatsworth. Today is my first day.”
Katrina was lacing up her boots when the young girl entered, so she turned and looked over her shoulder. The girl was innocent looking, very young, probably just of legal age that month. She has a small frame, only stood about 5’4 and had very pretty, long blonde hair with just a touch of red. This girl, she mused, looked about as threatening as a mouse. How she got assigned to interrogation was a mystery.
“I see. Well, come in. You can join me on my next case. A young guy, about your age. This may work out well. Have you finished your training?”
“I graduated with honors, Miss Katrina.”
“Good. Well, get yourself into a uniform. You’re about to have your first lesson in the real world.”
**
Jessica was looking at the leather harness in her hands with some discomfort on her face. She moved it around and around in her hands, wondering which end was which, and curious about the phallic looking latex protrusion.
Katrina was buckling her harness in place, positioning a black glossy dick between her legs so it pointed outward. She smirked at the young girl. “Men,” she explained, “Are very simple creatures. For years, we tried interrogating them with drugs, pain, torture. All along, it was obvious – women, as interrogators, were more effective. Because we have a capacity for cruelty far more than men. And men are terrified of us.”
Jessica nodded, looking at the strapon harness Katrina was in. In her all black sheer jumpsuit the black straps and cock almost looked like part of her – it was smooth, elegant. Very menacing.
“You take a man, you shove a dick into his mouth, or you sit on his face and nearly take his life away with that scent he used to found addictive – it fucks their minds so thoroughly that they become putty in your hands.”
Jessica nodded, listening.
“Or, you crush their balls in a vice, or with the heel of your boot, and they burst into tears like little boys. You ejaculate them onto their own face or mouth, and their pride is destroyed. Their egos, Jessica, are their weakness. Fragile, pathetic little boys.”
Jessica licked her lips nervously as Katrina stepped over to help the young girl into her harness. She told her to lift her leg, and she slide the harness up around her hips. She pressed the base of the dildo into the younger girls crotch and tightened it into place. Feeling Katrina’s breath on her face, the girl’s cheeks flushed.
“Don’t be ashamed if you get sexually excited by this,” Katrina smiled. “No one said you couldn’t like your job, Jessica.”
“Alright,” she replied softly.
Katrina turned the girl by her shoulders and made her face the wall mirror. “Stand up straight now. Don’t you like it?”
Jessica found herself strangely aroused at the sight of herself in the new harness; the dick was glistening, and seemed almost a part of her. She was still a virgin herself, but the thought of pushing that penis into a man’s mouth or ass was exciting to her. But it made her blush.
**
Jacob was face down on this large, uncomfortable steel frame that spread his arms out over his head, and opened his legs up wide. They had removed all of his clothes and he felt terribly vulnerable in the cold room, and was shivering in no time as he watched the men place a variety of tools and gels on a metal table in front of him.
The table was slightly low to the ground and his wrists and ankles were in metal shackles that gave no slack. His flaccid penis was positioned inside of a small hole in the base of the table.
When the door slid open he tried to lift his head but couldn’t see anything from his position.
He heard two sets of boots and saw a glimpse of the two women, not recognizing the sweet petite blonde girl. When his eyes met hers, he let his mouth open a little. She was beautiful.
Indeed, when Jessica looked at Jacob she felt the same – and instantly felt some sadness for the man. This was a man she was there to break, destroy, then send to be executed.
Katrina walked in front of Jacob at once, and his eyes fell to the stiff member that now protruded from her crotch. “You ever sucked dick, Jacob?”
“No,” he said softly.
“Jessica, come here. Put your cock in his mouth.”
It was all very sudden for Jessica, and she did not have time to adjust. But she walked right over and averted her eyes from the pleading man’s gaze. When he tried to turn his head Katrina leaned over and held it in place.
There were muffled noises and gagging sounds as Jessica pushed her member into Jacob’s mouth. Through the sheer material of her uniform she could feel his breath coming from his nose, right against her crotch, and it felt good.
“Ease back and forth, Jessica. It’s ok. You won’t choke him.”
Indeed, she did choke him though, his eyes watered and tears were streaming down his face in no time, but she kept pumping. She moved her fine hips back and forth slowly, holding his head with her hands when Katrina let go and walked around to the other side of the table.
“Keep pumping,” Katrina ordered, squeezing lubricant onto her fingers and moving to the man’s vulnerable ass.
He had no idea she was back there; he was too consumed with not choking, his eyes shut tight as Jessica held his face now in her hands, delicately pushing strands of hair out of his eyes. She was now mesmerized with the sight of all 8 inches of her black latex cock pushing in and out of his mouth. He had opened his mouth wider now to give her less resistance, and opened his throat as to not gag. His pink cheeks sucked in and out with each shove of the cock, and he was moaning softly.
Then, suddenly, he jumped, the table rattled, and the cock popped out of his mouth and he screamed, “AHHHH!!!’
Jessica looked up to see Katrina smiling, her hand somewhere between his legs.
“This boy is tight,” she commented out loud, her index finger pushing through the walls of his tiny asshole. “Shut him up, Jessica.”
Jessica nodded and pushed her cock back into his mouth, and he kept sucking, gasping at the same time though, twisting as Katrina’s hand moved back and forth. First one finger, then two, wiggling them around a bit, turning them, then making it three.
“He’ll be just fine. You’re about to fuck a man for the first time, Jessica. Once you deflower a man with your cock, you own a part of him forever.”
Jacob’s eyes were now open, and he was looking up at her, begging her with his gaze. She found him to be so beautiful, but she was so turned on by how humiliated he was. The tears had stopped but his eyes still begged, and he let her pump her cock in and out of his mouth with ease.
“Come around here, Jessica. I’ve prepared his hole for you.”
There was a distinct “pop” when her cock came out of Jacob’s mouth, and he lifted his head, gasping, and said, “Please..wait…”
Jessica smiled at him but moved out of his line of vision. With both women behind him where he could not see, Jacob struggled on the table in vain.
“Look at the way his ass moves back and forth,” Katrina said to Jessica. “Learn to enjoy watching them writhe and try to get away.”
“I do enjoy it,” Jessica said. “I earned high marks in the academy because my natural leanings toward sadism were so high. I had lost virtually no points for compassion, even in the hardest virtual reality tests.”
“You don’t feel sorry for this man?” Katrina asked.
“No, Miss Katrina. Not at all.”
Jacob gasped, turned his head what he could. “Please, I’m begging you, I told you I will do anything you want. You know I will cooperate with you.”
“Entertain us with your ass cheeks, then, Jacob. Let’s see them wiggle around for us.” Katrina smiled at Jessica.
Jessica smirked, and watched the boy jiggle his ass cheeks, his face now buried down to hide himself. Without warning, Jessica gave his right ass cheek a firm open hand slap that echoed throughout the room and made him gasp in pain.
“Tighten them up, boy!” Jessica snapped, in a tone Katrina had never heard, and one that impressed her.
He tightened his cheeks together and Jessica put lubricant on her finger, then with ease spread his cheeks open and pushed it in, causing him to wail in pain.
“That’s not very tight!” she scolded. “I want to feel you gripping my finger. Pump. Squeeze it.”
Katrina snickered and paced around, watching Jessica with amusement. Jacob was grunting and shifting back and forth as he tried vainly to please the young blonde.
“He’s got a strong ass,” Jessica told Katrina, taking out her finger and wiping it on a cloth. “Can I take him now, Miss?”
“By all means,” Katrina waved toward her with approval. “Just position yourself solidly behind him, and go slow at first. Let the head of your cock pop through the asshole, then slide it in, letting it find its way until he has accommodated you all. Then hold his hips, and ride him. After he’s lose, you can fuck him pretty hard.”
Jessica’s eyes lit up. Jacob was whimpering to himself, apparently in disbelief over what was about to happen.
Katrina walked over to him to pet his hair. “Isn’t this sweet? Two virgins?”
Jacob gasped in pain, eyes shut tight.
“It won’t go in,” Jessica complained.
Jacob wailed, and Katrina, without hesitation, slid her cock into his mouth to shut him up. She looked at Jessica. “Add more lubrication to your cock. Now, Jacob,” she turned to him. “You have to relax, or it will hurt more. Trust me. Loosen your muscles like a good boy for Jessica. She’s knew at this and isn’t as graceful as you may like.”
Tears were once again streaming down his face.
“Ok,” Jessica grunted a little, then sighed as the head of the cock popped through, and she found the length of the shaft to disappear slowly but easily into his creamy cheeks. The sight of it was fascinating to her, and she slowly, carefully slid it back out almost all the way. Then, in again.
Meanwhile, Katrina was holding his head in place and watching her young protégé at work. Smiling, she asked, “Does it turn you on, Jessica?”
“Oh, yes!” she sighed, watching the cock pump in and out of the man’s tight ass. She held him by the hips and started pulling him back on her when she pushed forward, and he whimpered in pain.
“It looks so slick..” she said, licking her lips. Her hair was falling in her face now, her cheeks flushed.
“You are a very beautiful young woman, ” Katrina said to her, watching the young girl glow with passion as she took the man from behind.
“Thank you, Miss Katrina,” she smiled, “can I keep going? Can I go faster?”
Katrina slid her own cock out of Jacob’s mouth and he gasped in pain, drooling now, the saliva dripping to the floor. He lowered his head weakly and just moaned. Katrina walked over to the young girl and observed her activity.
“Yes, keep going. You’ve got it now.” She smiled from behind her, watching the young girl’s passionate enthusiasm. From behind, she saw the petite blonde’s ass as she rode it and out of the pinned prisoner, and she slowly reached up and put both palms on her cheeks, feeling her rhythm as she fucked the man.
Jessica was holding his hips as she pumped in and out of him, aware and aroused at the feel of Katrina’s hands kneading into her round ass cheeks. She felt the woman’s breath at the back of her neck, and felt the distinct feel of the latex cock she was wearing push up against her crotch. It felt good.
Next, she felt two hands slide around her jumpsuit and cup her breasts, and then she was on fire. She was pumping faster, her eyes closed, and she felt the two strong hands massage her nipples to hardness with ease, and then a warm mouth on her neck.
She found herself squeezing her thighs around the cock that was now between her legs, rubbing it in against her pussy. The man’s moans were music to her ears, and soon she turned her head over her shoulder, opened her mouth and accepted the woman’s tongue early.
For some time they remained this way; Jessica fucking the man slowly, with deep, accurate thrusts as she held his hips; Katrina standing behind her, both hands cupping the younger girl’s breasts from behind and massaging her nipples, and her own cock pushing at the crotch of her jumpsuit.
And they were kissing; full lips, eager tongues, and the young girl tasted sweet to Katrina, she was a hungry kisser, her mouth small and delicate.
Jessica found herself letting go of the prisoner’s hips to reach down to the crotch zipper of her jumpsuit, unzipping it as she still took Katrina’s tongue eagerly into her mouth. Her fingers found her wet pussy and went to work, massaging and rubbing herself to near climax in a matter of minutes.
She found herself reaching under and grabbing the tip of Katrina’s latex cock and pulling it toward her, straddling it, aching to have it inside of her.
Breaking the kiss, Katrina smiled, whispering to the young girl, “You want to be fucked right now, this way, for your first time?”
Jessica let out her breath, “Yes.”
The younger girl kept her eyes closed; she was mesmerized by the sensations of the moment, from having her cock inside of the tight young man to feeling Katrina unzip her jumpsuit and start massaging her breasts from the inside. She gasped at the feel of her cool latex gloves against her naked erect nipples, and suddenly was aware of a sharp penetrating thrust between her legs.
Katrina reached down and used her hand to guide her cock into Jessica’s tight pussy, and listened to the girl’s gasp as it entered her. She buckled and went over the prisoner’s ass, still holding her cock tightly inside of him, now laying over his backside.
Jacob, half delirious with pain and humiliation, was only vaguely aware that the young girl was being fucked from behind as she slumped over his naked body; he heard he cries of orgasmic pain and felt a shock wave through him every time she was pumped by Katrina as it shoved Jessica’s cock further into him.
He was vaguely aware of anything but the final removal of the cock from his ass, and the sounds of the two women sucking each other’s nipples, going down on one another and ultimately cumming. In fact, he thought that was just a dream, really, a surreal bizarre twist of reality as his ass continued to pulsate painfully long after the cock had been removed.
Jacob even dozed, exhausted, and was awakened by the scent of wet, hot pussy and suddenly in darkness. He sensed it was the younger girl, and her scent was sweet, he felt suddenly safe between her thighs, and his tongue willingly and eagerly because to explore the walls of her pussy.
Then he heard Katrina’s voice, from behind, say, “My turn to fuck him, you tell me if he isn’t licking well enough, Jessica.”
Then pain shot through him as a new cock was shoved deep into his tight asshole, and he cried out in pain but it was muffled by the younger girl’s thighs. She squeeze his face with her legs and said, “Keep licking.”
With every thrust at his ass his face was pushed deeper into Jessica’s pussy, until finally she gave an exasperated sigh and stepped off of him. He blinked at her and saw she was naked – and so amazingly beautiful – he wanted to crawl into her arms and be held by her, she looked so delicate and innocent.
Smiling at him, she turned around, bent over, and spread her ass cheeks close to his face. Katrina shoved her dick in harder, pushing him forward, ordering, “Tongue her hole. I’m watching.”
Hesitantly, he let his tongue out of his mouth and tried to position it on her asshole, but the thrusts kept him off balance. Jessica looked over her shoulder impatiently. “Stick it IN!”
Katrina pumped him deeper, so deep that pain shot through him, and he gasped in pain and pushed forward what he could on the table and pressed his tongue delicately into the young girl’s ass. She spread her ass cheeks for him and backed up a little, pressing her ass into his face.
“There you go,” she said.
Katrina pumped harder, and with each thrust his nose was pushed deep into the warm crack of her ass as he vainly tried to move his tongue and find the hole. When he did, he bit back his disgust at the act and pressed inside, feeling her asshole give way and allow him to enter.
Then, thankfully, he fell unconscious.
***
After the prisoner had been sent to his cell, barely conscious still, Katrina brought the young girl into her office and had her sit down. Jessica’s cheeks were still flushed, and she had pulled her long hair back into a clip.
“You have a tremendous amount of potential, young lady,” Katrina smiled.
“Thank you, Miss Katrina,” she replied.
Katrina sat back in her chair pondering the girl for a moment. “I have a unique case for you. There is a man I had earlier today, a friend of young Jacob’s. His name is Allen, and I was unable to break him. Together, I think we could.”
“Show me the way, I’m ready,” Jessica smiled.
Katrina grinned at Jessica’s eagerness. “Easy now. He’s resting, and his balls are going to be quite sore for some time. I think we’ll give him a day or two to recover before unleashing you on him.”
Jessica smiled.
“But I think we may be able to break him with some deep anal training and torture, some masculinity re-programming and perhaps something even more sadistic.”
Jessica was still beaming. “I can’t wait, Miss Katrina.”
Katrina stood. “Excellent. Then I’ll call on you when we’re ready. You did a good job today.”
Jessica nodded and excused herself.
When she had left, Katrina sat back in her chair, arms behind her head. Yes, it had been a good day.
But the next day would be even better. She had some plans for Allen. Plans indeed.
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