Changing Sides Pt. 04

Charlie walked down the street, shifting his backpack on his back, glancing at every mailbox to make sure that didn't walk past her house. He checked the time on his phone and started feeling nervous. It was only fifteen minutes until he had to meet Janice, and he wasn't sure how far he had left to go. Finally, he saw the number she had given him, and he eagerly jogged up the driveway.

This was his first time meeting Janice at her house instead of playing at his apartment, so he wanted to make a good impression on her. Though, her house had already made an impression on him. Her house was a small mansion, at least three stories tall with a three-car garage attached to the side. It also had a sweeping porch out front, and the porch alone was larger than his bedroom.

Charlie had no idea how Janice could afford such a place while she was in college. Was her family rich? Did she have a rich boyfriend or some high paying side job? He would have to ask her if he could get her into a good enough mood tonight.

Charlie walked up the front porch and rang the doorbell, waiting patiently for Janice to come let him in. After a few minutes, the front door opened, and there stood Janice. She was wearing a tight-fitting blue dress, showing off her cleavage, with the skirt stopping just above her knees, showing off her toned legs.

As soon as Janice saw him, though, her face soured, and she crossed her arms. "You came here dressed as a boy?" She asked, waving her hand up and down, from his hoodie to his jeans.

"I-i'm sorry, Janice. I didn't know that you wanted me-" Charlie started to stutter but Janice cut him off.

"No, you don't blame this on me. This is about you, Charlie, this whole thing is about you. You're a girl, and it's time for you to stop forgetting this. Well, I won't let you get away with it anymore. You can't come in like this," she said.

"Are you sending me home?" Charlie asked, dejected.

"No. Here is what I want. Strip down, right here on the porch," she ordered.

Charlie hesitated for just a second, but then he slipped his backpack off his back. He started to pull off his hoodie, tossing it down on the porch. He kicked off his shoes and socks, then unbuckled his pants, pulling down his pants and boxers in one move. He stood in front of Janice in the brisk air, completely naked.

"At least your obedience is improving," Janice smiled. "Now, hold out your backpack."

Charlie bent over and picked up his backpack, holding it out for her. She opened it and dug around inside, before pulling out a pair of bright pink panties.

"God, you're such a girly girl," Janice laughed. She handed him the panties. "Put these on and I'll let you inside."

Charlie took the panties and slowly slid them over one leg, and then the other. As he pulled them up, he heard a car coming down the street. Janice watched as Charlie tried to decide what to do. In the end, all he did was pull up the panties and let whoever was driving by get a good look at his panty-clad ass. He did blush, wondering who may have seen him and what they may think of him.

"You can come in now, Charlie," Janice said, moving aside for him.

As he walked in, Janice reared her hand back and slapped him on the ass, which caused him to let out a little gasp of pain and pleasure. Janice then took his hand and gave him a little tour.

The first floor was mostly for entertainment. There was a living room, a long room with a pair of long gray couches lining either side, with coffee tables placed before them. There was a dining room with seats for at least ten people at a time. There was a small media room as well, a screen taking up an entire wall and with comfortable plush seats for eight. The media room also had a pair of small doors at one end of the room, though Janice didn't explain what those were for.

Janice then started him up the stairs to the second floor. As they climbed the stairs, she told Charlie that the master bedroom was on the third floor, but that he was not allowed up there, not yet, anyway.

The second floor held Janice's private office, a boring room of a desk, printer, and a port for her laptop. There were a few guest rooms as well, and a large bathroom with an open shower that fed into a small drain in the center of the room. There was also a massive bathtub that was almost a small pool.

Here, Janice ordered him to remove the panties again. She had his bath before her and ordered him to ensure he was shaved smooth. Once he'd dried off, she gave him lotions to spread over his pale skin, then started to apply makeup for him. With the makeup, she was slow and gentle, applying it before a mirror, talking through her actions, explaining each step for him, so he could learn how to do this himself.

After his makeup was on, she ordered him to get his outfit on. He had selected an outfit for today, a simple pink bra to match his panties, with a pink button-up blouse and a knee-length black skirt. Once it was all on, Janice had him pose and twirl for her, while she clapped her hand in appreciation.

Janice's phone buzzed. She picked it up and read a message, smiling to herself. "Almost time," she said. "Do you know what we are doing tonight?"

"No, Janice," Charlie admitted.

"Mmm, well, I'm having guests over tonight. Two lovely women will be joining us. One of them is a friend of mine. The other is someone who is...like you, in a way. My friend's pet, essentially."

Charlie was confused. Was he Janice's pet?

"What do I need to do, Janice?" Charlie asked.

Janice smiled at him and patted him on the head. "You just do everything that I tell you to do. And, if you're a good girl tonight, there's going to be a special reward for you at the end. But only if you behave, okay? So be on your best behavior."

Charlie nodded his head profusely.

"Good," Janice said, as her phone buzzed again. "Our guests are here, let's go meet them."

Janice took him by the hand and brought them back to the first floor. She pulled open the door and in walked the two women.

The first woman was just as tall as Janice but she was a thicker, curvier woman. She larger breasts than Janice, which she put out on display with a low cup black top. She wore a black skirt that was tight around her hips, accenting her hour glass figure, but loose and flowing around her knees. Her face seemed soft and kind, with just a touch of chubbiness to it, but Charlie could see a look in her eyes that scared him. Those baby blue eyes were hiding some wickedness that made him feel weak.

The other woman was about as tall as Charlie, and she was simply beautiful. She was slender and graceful, with small but perky breasts. She had dark hair but pale skin. She was dressed like a normal girl, wearing a yellow sundress that showed off her cleavage and her shapely legs, but it seemed clear to Charlie that she had no bra on, and probably no panties either.

"Ah, Laura, so glad you could make it," Janice said, pulling her friend in for a hug.

"Oh, of course, Janice, it's been far too long," Laura said, returning the hug and giving Janice a kiss on the cheek. "And I think that you remember Cameron?"

"Hello, Mistress Janice," Cameron said, bowing before Janice.

"Oh, just Janice is fine," Janice started, but Laura quickly interrupted.

"No, please, let her call you Mistress if you don't mind. This one has been rather rough to train, always forgetting her place, isn't that right, slut?" Laura said, lifting up Cameron's skirt and giving Cameron a hard smack on her bare ass."

"Yes, Mistress, I'm sorry," Cameron said

"Very well, you may call me Mistress as well," Janice told Cameron. She pulled Charlie forward, tugging on Charlie's hand roughly, so he stepped out in front of Laura, almost falling over in the process. "And this is my latest project. Her name is Charlie, and I'm trying to help her get over this delusion she has about being a boy."

"Oh, thinks she's a boy, huh? I can help with that. Let me get a good look at you, girl," Laura said. She grabbed Charlie by the face, turning her head this way and that. "What a pretty little thing, I'm jealous, Janice. But what's with these clothes? I thought you didn't like them this femme."

"She dressed herself that way," Janice said with pride.

"Really? And you've only had a few weeks, right? Well, with you training her, no wonder she's getting into the lifestyle so quickly. Any chance I can take this one off your hands?"

"Not a chance," Janice laughed. "But for tonight, do you think she'll do?"

"Hmm," Laura said. Laura's hand fell from Charlie's face and snaked down his backside. Her hand went under his skirt, and she cupped his ass before squeezing him, hard. Charlie blushed as she groped him, but did nothing. "Oh yes. This one will do. Our deal is still on."

"Very well. Come here, let's get to know one another," Janice said, running her hand across Cameron's face.

Janice led them to the living room, where Janice and Laura sat on one of the couches. Rather than sit on the couch, Cameron sat on the floor at Laura's legs, so Charlie copied him, gently sitting on his rear at Janice's legs. As he sat, he felt Janice's hands in his hair, petting him gently.

"So, do you want to tell them what's happening tonight, so shall I?" Janice asked.

"Please, this is your home, after all," Laura said.

"Very well," Janice turned to look down at Cameron and Charlie, putting a hand on each one's head. "Tonight, we're going to trade you off. Cameron, you'll be with me, and Charlie, you'll be with Laura. And Charlie, just to make this clear for you, since this is your first time in this situation, anything Laura tells you to do? You do as if I asked you. No hesitation, no questions. Understood?"

Charlie swallowed, hard, at the order. He had a feeling this would be unpleasant, but he wanted to look good for Janice in front of her friend.

"Good. And, both of you, if you do well, you'll each get a special treat at the end of the night, okay?"

Charlie perked up at the sound of the treat. What would it be? Would Janice use her hand on him again? He needed to find out, and that meant giving Laura whatever she asked for.

"Okay, then. Cameron, come over here, and Charlie, you're with Laura now," Janice said.

Cameron crawled over to Janice, and she directed him right between her legs. Laura, on the other hand, grabbed Charlie by the hair and dragged him over to her.

"Mmm, well, you know how to pretty yourself up, slut, that's for sure," Laura said, leaning back in her seat as she looked down at Charlie. "Want to know what I have in store for you?"

Charlie just nodded his head, and Laura frowned.

"I asked you a question, slut," she growled.

"Yes, please show me, Laura, er, Mistress Laura!" Charlie quickly corrected himself.

Laura laughed down at him. "My, what a good learner you are. Too bad Janice got her hands on you first. But since you asked so nicely, here."

Laura pulled up her skirt to reveal the strapon she had apparently been wearing since she walked in the door. The dildo was hooked to something on her thigh, she pulled it free and it immediately sprung straight up, almost like a real cock.

This one was massive. Janice's strapon usually had the seven-inch dildo, above average, but Charlie could take it. Laura's was at least ten inches long and almost as thick as Charlie's wrist.

"Let me guess, a little different than what Janice uses?" Laura smirked down at him.

"Y-yes, Mistress," Charlie whimpered.

"Too bad for you. Get over here and start sucking," Laura ordered.

Charlie obeyed. He crawled between her legs on his hands and knees, taking hold of her massive cock in his small hands. He gave the cock a kiss and started to lick it up and down, running his tongue along the fake cock's shaft.

Charlie heard a moan. His eye's glance to the side, where he could see Janice with her top off, her wonderful breasts bouncing free. Cameron was between her legs, eagerly lapping at Janice's tight pussy.

"Okay, enough foreplay," Laura said. She grabbed Charlie's head and shoved her cock inside him, making him gag as four inches of silicon cock roughly penetrated his mouth, already pressing against his throat.

She gave Charlie no time to relax. She grabbed his head and dragged it along the cock, making him worship her strapon cock. She laughed at him whenever he gagged or sputtered. He tried to say something, to ask her to slow down, but the words were muffled on her cock, and it only seemed to spur her on.

"Honestly, Janice, this one is seriously lacking in training. I mean, you've done well for as long as you've had her, but she can't even deepthroat yet?" Laura complained.

"You just need to...oh god, that's so good," Janice said, interrupting her train of thought to moan on Cameron's tongue, her breathing starting to get ragged, her face turning red. "Just shove it in her! Make her take it!" She cried.

"Very well," Laura said, grabbing Charlie's head with both hands.

Charlie looked up at her with pleading eyes, but Laura just shoved him down onto her cock. This time, the cock shoved right into his throat. Laura kept pressing until Charlie was balls deep on her cock.

"Oh, look at that, you're right. What a talented mouth," Laura said.

"With cock, yes, with pussy, not so much. Not like this one, who is, oh, god, it's so good!" Janice moaned. She let out a shriek and came on Cameron's tongue, twisted and moaning on the couch as Cameron lapped at her obediently.

After she came, Cameron started to pull away, but Janice pushed her back down onto her pussy. "I didn't say stop," Janice said with a satisfied sigh.

Laura pulled Charlie off her cock. She let him take a deep breath, then impaled him on her cock again. She did this over and over again, and Charlie's face became a mess of smeared makeup, as tears leaked from his eyes and spit leaked from his lips.

Laura stopped fucking his face, letting her cock fall from his lips, and she handed him a small bottle she pulled from her pocket.

"I assume you know what's coming next?" Laura teased.

"Yes, Mistress, you are going to fuck my ass," Charlie whimpered, meekly.

"Good girl. Now, lube up my cock, slut," Laura said.

Charlie popped the bottle open and started to vigorously lather the dildo with lube. Laura laughed as she watched him pour lube over every inch of the dildo.

"She taught you this part well, it seems. Lube it up good. Do you know why I have my slave lube me, slut?" Laura asked.

"No, Mistress," Charlie responded.

"It's because if they don't use enough of it, it's their problem, not mine. Now bend over and present that ass, slut."

Charlie's face turned deep red, but he did as he was told. He bent over for her, pulling up his skirt and pulling down his pink panties. He even reached back and pulled his ass cheeks open for her, exposing his tight, hairless hole.

"Oh, she doesn't have you caged up?" Charlie felt Laura's hands squeeze his small cock, which was rock hard. "Might not be her fault. She might not be able to find a cage small enough. Still, if you belonged to me, I wouldn't let this little thing be free."

Laura gave his cock and balls a gentle slap, just hard enough to send a small shock through Charlie, but not enough to seriously hurt him. He let out a little whimper, then he felt it, the head of Laura's massive cock pressing against the entrance to his tight little hole.

Laura leaned over him, her lips just an inch from Charlie's ears, and she whispered to him. "You know, I'm not as nice as Janice," She said, and she pressed the tip of her cock into Charlie.

Just the tip was enough to spread him open, far more than any toy Janice had used so far. It was stretching his tight ass so far open, Charlie thought it would split him open. He grunted and moaned in pain and pleasure as she penetrated him.

"See, I don't care how you identify. Guy, girl, I know what you really are. Just another sissy bitch, ready to take some cock. And do you know why you're a bitch?" Laura teased, sliding a few more inches of cock into his ass.

Charlie squeezed his hands together, his eyes closed, grunting as he tried to just lay back and take the massive cock that was working its way deeper inside him.

"I-its because I serve cock, M-mistress," Charlie groaned.

"Good answer! That's right, you serve cock. Be it a dildo like mine or the real thing, you live to serve cock. That's all a sissy bitch is good for," Laura taunted him.

She grabbed his hips and pulled him down as she pushed in, and in that thrust, she fully impaled him on the dildo. All ten inches were inside his tight ass.

"Now, show me what a good bitch you are. Fuck yourself with my cock," Laura ordered.

Charlie leaned forward, moaning as her cock slid out him, leaving him feeling empty. Then he slowly started pressing back, taking her cock balls deep again. As he kept fucking back onto her cock, the pain vanished, and all he felt was the pleasure of riding her big thick cock.

"Come on, faster, slut!" Laura said, slapping his ass.

Charlie started to fuck himself back harder, his butt slamming back against her hips over and over, impaling himself on her thick dick again and again. He started to whimper and cry in his girly voice.

"Oh, Mistress Laura, your cock feels so good inside me, it's so big and thick, god I can feel it so deep inside," he moaned.

As he thrust back onto her cock, he heard little moans escaping Laura's lips as well. He figured it must be double-ended, part of the dildo must be inside her too, pleasuring her as he rode her cock. That only emboldened him, and he started to slam himself back onto her wildly.

"Oh fuck, yeah, you little slut, you little sissy slut. That's it!" Laura shouted.

She grabbed him by the waist and started to thrust into him wildly, pounding him senseless. She threw the whole weight of her body into it, slamming into him as hard as she could.

Charlie moaned with pleasure as she railed him. "Yes, Mistress Laura, fuck me, fuck me with that big cock!"

"Damn straight, slut," Laura said. She used one hand to reach up and grab Charlie's hair, grabbing it and pulling it back roughly, forcing him to arch his back

Charlie glanced to the side to see Janice on her knees on the couch, ass in Cameron's face. Cameron was licking at Janice's asshole while furiously fingering her tight pussy. Janice let out another scream of pleasure as Cameron made her cum yet again.

Meanwhile, Laura's thrusting was getting hard and frantic, almost animalist in her need to be inside him. She was also groaning with pleasure with each thrust into him.

"That's it, take it, take it, YOU! DUMB! BITCH!" Laura screamed, thrusting into him hard. These last few thrusts sent Charlie over the edge. He whimpered with pleasure, trembling underneath the powerful woman, and his small cock blasted out its meager load into the carpet.

Laura let out a few more thrusts as well, and she started to spasm overtop him. "Fuck, fuck, fuck!" She cried as she came, hard, burying her cock into Charlie's ass one more time.

With that, the room started to get quiet, short of the sound of heavy breathing. Laura was gently stroking Charlie's hair, then she pulled out of his ass slowly. Charlie whimpered as she withdrew, leaving him feeling used and empty. Once she was out, he turned back to face Laura, crawling over to her legs.

Sitting next to Laura, Janice had sat back down on the couch, draping one leg over Cameron, also gently playing with Cameron's hair.

"God, your little slut can come from anal? Any chance I can change your mind, take her off your hands?" Laura asked Janice.

Janice just laughed. "No, this one is mine, at least, until I'm sure she's where she needs to be. Then, you can hound her all you want. I take it she did well?"