Making a Woman of Him Ch. 09

"Well, Catie, ol' girl, I guess that's your answer..."

"No! I'll...do it. I'll do it. Just show me what to do..." He looked down at the floor as he walked behind her.

"What?!! You've never fucked anyone in the ass before, Chester? You've got to be kidding!" John's confusion looked sincere, staring at Millard to see if he believed it. "Well, alright then. Come on over here and let's take your cherry!" He backed away a little more, careful to not touch him as if he might catch a disease.

"Spread her cheeks, Ches."

Standing behind her, his hands pulling apart her beautiful ass cheeks, he saw now what they had been doing: written around her pink asshole in permanent marker were the words: Fuck me here, I'm a virgin. He stared at the wrinkly hole, a dribble of cum dripping out, and he swallowed.

"Don't delay the inevitable Chester m'lad. Take that prick of yours and help her over the edge!" Millard had gotten up to witness the taking of Chester's virginity.

He had trouble pulling her cheeks apart and pressing his penis against the hole until he realized he had to step closer to her. With his thighs practically pressed up against her his shaft was against her crack, too high to penetrate her. He bent his knees feeling the slimy ribbed texture of her anus rubbing along the underside of his penis and he shivered in disgust. Suddenly, he felt his glans up against the rosy muscle and he felt her open to him.

"Stick it in me, Chester. Please. Before they hurt me. Please?" She tried to turn and see him, but her arms kept her facing forward.

He pushed forward softly, still not wanting to go through with it, but too terrified to back out and before he knew it, his head was inside her: warm, wet and unlike anything he'd felt. Not like Roxie's cheeks, or Corrine's tongue, or Yvette's hand, even when she had put lotion on. The memory of Yvette stroking him came back like a wave crashing -- the times she would make him watch as she spread the rose scented crème on her hands, taunting him, forcing him to beg her to give him relief. The anger he had felt, combined with humiliation, pushed him over some hidden threshold and he shoved harder into the slippery envelope of Catherine's rectum.

"OH GOD!!!" She screamed as he penetrating her, the sound of her pain slowing him briefly. "STOP. FUCK! Chester! STOPPPP!"

He knew that wasn't whatever the word was she needed to say to make him stop, and the cheering from John and Millard only confirmed it. He let go of her cheeks and put his hands up her ribs, pulling her down onto him, feeling his cock inching further into her. He had no idea what fucking a vagina would feel like, but he couldn't imagine it feeling better than this: her tunnel was so tight it grabbed him like nothing he'd ever felt. He looked down and saw he was only half-way in, but the feeling was incredible. He paused to catch his breath and feel the throbbing of her heartbeat against his penis. He pulsed his penis back, expanding his head inside her bowels and was pleased to hear her mewl in response.

"She likes whatever you're doing Chester. Keep it up and she'll be cumming in no time."

He moved his hands to her breasts -- he wanted to feel them, to crush them as he pushed deeper against her. She protested, begged him to not touch her nipples; he could feel tears, or snot, dripping from her face as he purposefully ignored her, much to the entertainment of the other two.

He avoided touching both wire clamps on her nipples at the same time, not wishing to get electrocuted, but with each touch she yelped in pain and pushed against him. He didn't understand her, what she was doing here, or how she could possibly enjoy this, but he had stopped caring, only wishing to pursue some animal emotion that he'd never felt before.

He started to pull out, slowly, listening to her beg him to fuck her hard in the ass again. It was indescribable the feeling of her rectum stroking his cock so softly and so tightly. He could feel the ring up against the bottom of his glans and he stopped.

"What...do...you...need...Catherine?" He could barely get the words out, his heart was pounding. He was confused by her shouts for more and for him to stop. He still couldn't believe how amazing this felt.

The other two stopped and listened, waiting for her to answer.

"You're hard, hot cock, Chester. In my tight ass. Hard. Hot. Fuck me, Chester, I'm so close. I'm so close." She was panting, her head moving from side to side, her body trying to push against him to take him into her.

He bent his knees, telegraphing what he was going to do and waited.

"Please! Chester. Fuck. Me. HARD! OOOOOHHHHHHFUCCKKKKK!"

He pushed up into her as hard as he could, shoving with his legs, lifting her feet off the floor momentarily, forcing her to hang on his cock as it slowly pushed past her defenses, his girth stretching her sphincter further than she'd ever felt.. He couldn't take it much longer, the sounds of her begging him, the feeling of her nipples against his fingers and then, the squeezing of her tunnel on his shaft. He was still only half-way into her, her rectum began rippling against him, milking his seed out of him until he erupted in a burst unlike anything he'd ever felt.

"YESSSS, CHESTER, YESSS, ooohhhh FUCCKKKKK MEEEEE, CHESTERRRR! FUCK MEEE!!!" Catherine went stiff, pressed against the table, her head arched back, Chester's cock buried as deep inside her as he could go.

Millard shut off the box as she climaxed and she squeezed Chester's cock even harder, a second orgasm crashing over the first.

He could hear her crying now, crying in relief and abandon, her body beneath his, her breasts in his hands. He put his fingers over the clamps and pulled them off and he felt her squeeze him again, this time so hard he thought she would tear his penis off his body.

"GODDDDFUCCKKDAMMITGODDFUCKKFUCKKFUCKK" She screamed as the pain of the clamps being removed pushed a third wave through her and he held onto her nipples, hoping to massage the pain away. She pulsed against him, thick strings of drool coming down onto his hands. "GODDDDCHESTERDAMMITFUCKYESSYESS YESS!"

He slowed down, trying to not get hurt as his penis deflated and started to pull out. He had lost track of the others -- it almost felt as if he had passed out -- until finally his hands dropped to the table and he pulled out completely. He looked down to see specks of shit on his cock and he almost gagged, the smell of her rising up along with his shame.

He stepped back and went to get his clothes.

"Not so fast, Chester, old boy." Millard stopped him. "You're not off the hook yet. Not by a long shot."

He felt bile in his throat and wondered what would happen if he vomited all over Millard. He saw John lowering her arms off the hooks, bending her at the waist to let her rest her cheek against the table.

"What?" He barely whispered.

"You came back here. Against the deal. You broke the deal. We'll need a new deal, right?"

He stood naked, stinking of shit and close to getting sick. "What do you want?" He had to get out of there, get to the bathroom and get cleaned up immediately.

"You. And Catherine. You understand, first of all, that this never happened, right?"

He nodded. He'd never admit to it even if they brought it up.

"Secondly. You understand she's looking out for us over there and you're not going to fuck that up, right?"

He nodded again. Who gave a shit? Shit. All he could smell was shit. The bile bubbled against his throat.

"Okay. So here's the new deal: you're going to look out for us too, got it? You'll both be watching over there. We'll interview you separately, so your stories better be straight. You got that, Chester? You'll be back here in a couple of days and if you don't want to be in her position, you'll tell us what you know."

He nodded, reaching for his clothes and ready to run.

"Oh, and one other thing you should know. Catherine will be given a little task to do for us that we'll expect you to report on. You'll know it when you see her next. Now get the fuck out of here you little faggot and don't come back until we call you."

He rushed into the hall, up the stairs to his floor and into the bathroom. Dumping his clothes on the floor, he started the hot water in the shower and stood under it, crying for what seemed like an hour before he found his way to his room, collected his stuff and walked back to the women's house.