Making a Woman of Him Ch. 09

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Chester witnesses Catherine's secret life.
5k words
4.25
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Part 9 of the 17 part series

Updated 11/02/2022
Created 02/19/2014
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ElRoylk
ElRoylk
330 Followers

It took until about mid-day before he finally felt like his normal self. He'd been in a fog all morning, the pain from all of the attention to his peter distracting him. He knew he wasn't quite sharp when he failed to answer the questions posed by Professor James in History, something he should have, did! know but wasn't quick enough to respond.

Sitting in the cafeteria, getting ready for his next class he suddenly realized he hadn't brought all of the materials he needed for the following day's debate. His first thought was to just go back to his room at the men's house and pick it up, but the deal he'd struck with the two houses was he wouldn't return before the week was up.

It wasn't like him to cheat on a deal, but this was crazy. If he didn't have his notes, he'd let his team down. His mind raced through the possibilities, sneak in through the back door and up the back stairs -- he'd have to pass by John's room, he'd be screwed. Monday. First Monday! First Monday night almost no one would be at the house -- what was it this month...a movie. That was it. They'd be at the movie house. He gathered his books, dropped the tray on the conveyor and left for class, relieved he had pulled himself together.

It was after dark when he approached the house, concerned he'd be seen in spite of it being empty. Still, he chose to go in through the back door and up the back stairs. If anyone was home, they'd likely be in their rooms, or in the front room. Carefully opening the door and closing it behind him, he softly moved through the darkened kitchen. Stopping at the bottom of the service stairs he listened for any sounds of televisions or conversation. Hearing nothing, he moved quickly up to the first landing, stopping again to listen.

His heart pounded at the sound of something, a noise from upstairs. He calmed his breathing and listened. Something, but he couldn't tell what. Someone was home, that was certain. He waited, debating what to do: it was likely nobody who cared about his deal, but if it was, he'd be in a lot of trouble. It was likely they wouldn't even know he was there -- he'd just keep going to his room and quietly leave again.

Still scared, he continued more slowly up the next set of stairs to the 2nd floor landing. The sounds were louder now -- voices and...a woman's cry! He froze, staring down the hallway from the open doorway, listening -- a slant of light coming from a room down the way. There it was again! A cry for help! Sobbing! Chester moved quickly toward the sound, keeping as quiet as possible, until he could tell which room it was coming from. John's!

"No! Please! I'm sorry. Yes! I'll do better! I will. I will. Please. Just...noooooohhhh...OHHH!"

And then a slap! They were hitting her! Shaken, he didn't know which way to go -- to just leave, get his things and run, or see if he could intervene. He couldn't live with himself if he left her -- he had to see what was going on. As softly as he could, he peeked through the opening in the door. He didn't know what to expect, but the scene in the room was beyond anything he could have imagined.

John and Millard were smoking! Smoking in the house! It was one of the rules they could get expelled for! He took a whiff and realized they weren't smoking cigarettes! Pot! They were smoking pot! Before he could completely comprehend the idea, his eyes locked onto a young woman, her back to him, dressed only in her bra and panties (he noted their design immediately, and unconsciously registered she was well brought up, conservative, and uninventive). As he took another look, he gasped. Her hands were tied above her head, held there by ropes attached to two hooks in the ceiling. Her legs were spread behind her, and she was leaning at an angle away from him.

Millard looked up at the noise and before Chester could get away, he grabbed him by the shoulder. "Hey, John, lookee here! It's our friend Chester! Chester, you faggot. What are you doing in the house?" Millard dragged him in.

"No!" The woman gasped, trying to look away. "No."

John looked to her and then to Chester, smiling grimly. "Well, well. Isn't this an unpleasant surprise. Have a seat, Chester. We'll deal with you in a moment."

He slumped into a chair near the door and waited, looking up at the woman. Something about her, her voice, her build. He knew her. Who was it?

"So, Catherine, one of your girlfriends is here. Shall we have a little party?"

Catherine! But...what? What was she doing here? And like this?

"He looks a little surprised. Any reason he should be surprised to see you like this? Don't you share your secrets with all the girls?" John moved behind her, raised his hand and slapped her ass cheeks, the sound echoing in the room with her cry of pain. "We asked you to do us a small favor. We told you what the consequences would be if you disobeyed us, and now, it appears you've decided to test our will. Is that it?"

"No," she gasped between sobs. "No. I told you what I had heard. I had no idea Roxie was seeing someone else. I swear it!"

Chester panicked at the implications, his heart racing.

"But," Millard said menacingly, "but you knew something was up. You said it yourself." He moved over to her and unsnapped her bra, letting her breasts swing down. He pulled the straps and cups up over her head out of the way.

Chester saw now that she was stretched across the edge of a table at about 60 degrees. From where he was, he could just see the edge of her breasts and a single nipple. He could see tears streaming down her face.

"No. Please. Don't. What are you doing?"

Millard was fiddling with some kind of black box on the table -- visible to Catherine but not to Chester. Eventually, he pulled a red wire from it, with some kind of metal clip on the end. He held her breast and clipped it to her nipple. She screamed in pain and tried to struggle, but the way she was trussed up, she couldn't move.

Chester turned his face away, the image of her agony causing a strange reaction in him.

"Chester!" John commanded. "Get over here."

He shook his head, not wanting to comply.

"Mother fucker. Get your candy ass over here. You're a girl, right?"

He shook his head again, but found himself walking over to John's side.

"You know Ms. Cruline, right?" John pulled Catherine's face to the side, forcing her to look at Chester.

He nodded, asking her silently if there was anything he could do. At that moment, Millard held her left breast and attached a second clip to that nipple. She screamed the moment she felt his hand on her breast, but John held her head, facing him.

"Now, now, Catherine. You know you want this. Obviously you must have wanted it, or you wouldn't have misbehaved, right?" He made her look up at him, his eyes cold. "Tell Chester you want it. He's a little scared we're hurting you."

She tried to turn her eyes away, her sobs wracking her body. Between gasps, she opened her mouth. "It's...it's okay...Chester. John's right. It's... what I expected."

He let her head go and she cried openly.

Chester stared at the clamps on her nipples, her breasts hanging free, the wires going to the black box.

"It seems a little unfair that Catherine is the only one undressed, don't you think, Chester?" John looked over at Millard. "She probably hasn't seen a girl quite like you before."

Before he could think, he blurted out, "Oh, she's seen all of me already..." and then realized it was probably not the right thing to have said.

The two stared at each other and then down at her. "What? Another little secret? My my, Catherine, you are just a box full of secrets today, aren't you." John motioned to Millard and stepped back. "Asshole," he turned to Chester. "Since you two are on such intimate terms already, how about losing the clothes. Now!"

He knew it was stupid to protest, either he or Catherine would just get hurt, besides, what did he care to be naked? It was puzzling to him, didn't they think he was gay? Why would they want him to be naked if they were as homophobic as they seemed? As he began to undress, Catherine stiffened, her mouth open in a silent scream.

Millard had turned on the machine, and quickly turned a knob.

"OHHHHGOOODDDDDD!!!! FUCK FUCK FUCK!!!" She screamed after the initial charge of electricity coursed through her nipples in that first instant, recovering only when Millard had adjusted it, after the fact.

"Stop it, you little cunt!" John slapped her hard on her ass cheeks. "Pull yourself together. You know what to say if you want this to stop. Now shut up!" He slapped her again.

Chester had dropped his slacks, revealing his silk briefs. He was ashamed. Not at being naked, but at the realization that the suffering Catherine was going through was arousing him in some horrible way. Looking down, he saw his erection beginning to push the panties away from his body.

"Holy Mary, mother of Christ. Would you look at that Millard? The guy's getting off on this. Mother fucker." John grabbed him by the arm and pulled him in front of Catherine so she could see him. "Look at that, little lady. Your girlfriend is getting a hard on watching you suffer."

Catherine's face was red and puffy from crying. The pain from the electrical stimulation had subsided a little, but it came in pulses, obvious to Chester as she screwed up her face every few seconds. He looked down at her nipples, pulled away from her body by the weight of the wires, the teeth of the clips pinching into them. He felt his penis pulse.

"Oh, god. No. Oh. No....nooooo..godddd, please. Stop. Make it stop. He...he can't see me this way...he..." She continued to plead with them, but they only seemed to enjoy it more.

"She actually wants this, Chester. Really. She gets off on it. Seriously." It was Millard, his fingers resting on one of the machine's black knobs.

"Everything. Off." John motioned to Chester to finish stripping.

"Holy shit. John! Did you know this queer was hung like a horse?"

Chester blushed deep red at the attention his erection was getting. Looking up, he saw Catherine staring at him, her mouth opening and closing, whether from pain or the shock at his size.

"I thought you said you two were buddies, Chester. Looks to me like she's never seen you before." John walked behind her. "Let's make it a little easier for you, Cate." John put the joint in his mouth, took her panties in his hands and slid them down to her thighs exposing her cheeks and her dark triangle of hair. "That's more like the way you like it, right, darling?" He put his palm on her ass, lightly rubbing it. "How many?"

She just sobbed, shaking her head, tears falling onto the table.

"I asked once, and I won't ask again!" He raised his hand, ready to strike her.

"15. I deserve 15 for disobeying you."

"You know the drill, honey. And as we have agreed, no penetration of your pretty little virgin twat. But...15. If I know you, you will be dripping by seven." He raised his hand and brought it down hard.

"OHHH GODDDAMIT!!!" The slap caused her to jump against the table, her eyes screwed shut. "One," she barely could say it. "Thank you."

Before she'd finished saying it, his hand came down again, and she screamed, her body jumping.

Chester watched, helpless as the two men alternately spanked and jolted her. More alarming to him was how stiff he had become, his peter harder than he'd ever seen it. He stood exposed to her, naked in a way he'd never felt before. Grimly, he was silently thankful she couldn't really see him; her eyes were either closed or filled with tears.

With the sound of the 15th slap echoing in the room, Catherine was barely able to mouth the final thank you, struggling to breathe. It looked to Chester as if her arms would be pulled from their sockets.

John had reached behind him for something out of a desk drawer. "Chester may need a little help figuring out where to put that thing, Cate. Hold still."

It was obviously a gratuitous remark, but from where Chester stood, he couldn't begin to understand what he meant by it. He watched as Millard pulled her cheeks apart and saw her open her eyes, shake her head and whisper a protest. "No." Even from where he was standing, he could barely hear her. Her eyes focused on his erection and her expression changed. She just shook her head side to side, staring at him and silently protesting.

The two had finished whatever they were doing behind her and he watched as they unzipped their pants. He couldn't see their penises, but he assumed they were hard and that they would rape her. Although, he wasn't sure if it was rape. John had said she knew how to make it stop. Why didn't she make it stop?

"You first, John. I believe it's your turn." Millard stood back, his cock now visible to Chester.

John reached up and gently stroked her breasts, letting his fingers glide down to her nipples. Chester watched him, his fingers so light. He watched her face, her expression of alarm as John's fingers got close to the clamps. She shook her head, her soft 'Nos' like puffs of steam from a locomotive. Even though his fingers never touched her nipples, she erupted with a scream of pain.

"FUCKKKKKK...NOOOOOO!!!!" Her body convulsed in agony.

When she started to buck against the table, Chester finally understood what had happened. John had obviously shoved his penis into her and was pounding against her. John's grunts mixed with her protests as he moved into a steady rhythm.

"You...little...slut," John exhaled with every push, "tell...Chester...you...want...THIS." He shoved hard at the end, her face popping open from the invasion.

She shook her head, tears flying off, trying to catch her breath. Streams of mucous flowed from her nose across her lips.

"Yeah, Cate. I think Chester needs to be reassured again." Millard knocked an ash from the joint into her hair and took a drag.

"Uhhhnn, I...I'm...I...unhhhh...OH FUCK!" John had reared back and shoved into her, hard. "I LOVETOBEFUCKEDINMYASS!"

It took several seconds for Chester to decipher what she had said, it all came out in one stream. He was shocked -- they were fucking her in her ass??? He'd never known people did such things. And it was so dirty!!!

John apparently was climaxing, he held her by her shoulders as he pumped into her, her head bobbing from the motion until he had finished. He smiled wickedly at Chester when he had recovered, pulled out of her with a small pop and pulled up his trousers. "You're turn, Millard. I think she's lubed up for you."

"Catey, my girl. You know how I like it." His hands came down to spread her cheeks as he pushed up against her.

"Please," she begged, her breathing was ragged. "Let me catch my BREATH!" She was shoved forward again as Millar impaled her, drops of liquid flying from her face.

"Tell me, you little bitch!" He shoved deep inside her.

"Fuck...me...in...my...ass...Mill...ard...so...I...can...stay...a...vir...gin." With each syllable he pounded her, her breasts bobbing against her chest, the wires threatening to fall off.

"Nice, unhhh, hunnh, Chester?" Millard looked up at him between thrusts. "She...unh...likes it in the...back...door...god this is sweet, Cate. So...fucking...sweet." He stopped for a second, his right hand drifting down to the box on the table. "You ready?"

"No...no...please Millard, noooooohhhh!!!!"

"Here we go sweetie...just the way you like it." Whatever he did, she stiffened, her face thrown back in pain as he shoved himself deep into her. "God that is fucking fantastic. John, I can feel the throbbing all the way down here. Fuck!" He brought his fingers up to her nipples and suddenly he went stiff, the electricity jolting between them.

Chester didn't know what to do -- the two of their faces both screwed up in agony, their bodies stiff, Catherine's cries of anguish filling the room, the sickly sweet smell of pot inside his nose. He saw John out of the corner of his eye, but the motion hardly registered. He stared at Catherine's breasts, the nipples red and vibrating, Millard's fingers pinching them, his face in pain, his body pushing hard against her.

And then it was over. Millard's hands fell to the table, his body went limp against her, his breathing labored and irregular. "God, Cate," he said eventually, "that was so fucking awesome."

Her eyes were still shut, tears streaming down her face, her mouth making small shapes with her breath. Her bra had slipped down her arms to rest against her head making a strange tiara.

"But, my friend," John interrupted the quiet, bringing Chester's attention back to the room, "she's not finished, are you, Catherine?" His voice wasn't like Millard's, Chester noticed. He enjoyed the torment, but Chester got the feeling Millard enjoyed...Catherine. "Answer me!"

"No..." she shook her head. "I haven't cum yet."

"But you want to, don't you, you little twat?"

She nodded, her eyes opened and pleading, but with whom Chester couldn't imagine. Not with him! He had nothing to do with this!

Millard pushed away, leaving her hanging, figuratively and literally. John's hand came around in front of her, stroking at her bush. She jumped at his touch, sniffling back the stream of liquid coming out of her nose. Chester watched as his fingers slid down between the table and her legs, between her legs.

"Say it."

She shook her head, her sobs changing to moans. "Please...don't...please...no...don't...you...no..."

"SAY IT!"

She jumped again as John's fingers caressed her, sliding into her vagina, running along her clit. She looked up at Chester, her eyes darting between his face and his pulsing cock, shaking her head. "I...ohhhh....fuck...ohhhh....god, no...John...don't...no...don't make me..OOOHHH!"

"Tell him. Beg him. We won't let you cum until you do." Underscoring his point, he pulled his hand away.

She moaned, licking her lips and looking around her wildly, first at Chester and then to see if either of the other two were anywhere in her line of sight.

"Do we need to start over again? I know you can sometimes cum that way..." John's hand moved across her ass cheeks, softly emphasizing the threat.

She inhaled sharply and shook her head. "NO. Please. No. Okay. Yes, okay! I'll do it." She looked at Chester, her face miserable. "Please, Chester. I need to cum. I need...you...to...fuck me in my tight ass."

He stared at her and then at John's impassive face behind her. He looked over at Millard, smoking the joint and watching the scene. Millard shrugged and sat down, unconcerned.

"Come around here, Chester, ol' girl. Usually we'd do this a different way, but as soon as Catherine saw that monster, we knew she wouldn't be happy without it up her ass...so...since you've disobeyed our agreement, you've got a choice..." John stepped back inviting Chester behind her.

It was his turn to shake his head. His mind was a swirl of confusion. Put his peter in someone's rectum? With other boys' ejaculate? He had lost track of whatever John had been saying.

"So...here, or there?"

He looked up confused, tears blurring his vision. "Wha...?"

"Shit. Listen, butt-fucker. You take it up the ass all the time, right? Well, now it's time to give it to our Cate, here. Either you fuck her tight little ass with that mother-fucking beast god gave you, or she'll just have to endure a spanking, just a tad bit harder than you just saw. And as for you...well, that we'll have to think about..."

"Please, Chester." She looked at him, her eyes begging. "Just do it. They mean it. They'll hurt me. It's the only way I'll be able to cum, and they won't stop until I do. Please."

He stared at the three of them, trying to clear his thoughts. Just last week he had been minding his own business, trying to get through school and on with his life. Now, after only a few days at the women's house, his whole life had been turned upside down. Looking at the cruel expression on John's face he thought it was Yvette's, the pain of what she had done to him rising up and threatening to overwhelm him.

ElRoylk
ElRoylk
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