Changing Sides Pt. 03

Charlie's hair was still wet from his bath as he walked out of the bathroom, pulling his bathrobe tight across his slender frame. He turned down the hallway and pushed open the door to his bedroom. Sitting on his bed, waiting for him, was Janice.

Janice was wearing a tight fitting t-shirt that showed off her bountiful breasts, as well as her toned, athletic body. Her jeans hugged her waist, showing off her curves and her perfect ass. As Charlie entered the room, she had been staring at her phone with a bored expression on her face.

"Finally, you're done," Janice said. "But what's with the robe? Drop it," she ordered.

Charlie's face turned a shade red, but he untied the robe, dropping it as ordered. It fell around his feet, and now he was standing naked before her.

"Mm, looks like you did a good job for your first try. Here, sit on my lap and let me feel you up," Janice teased.

Charlie walked over to her and sat on her lap, and she started to run his hands all over his legs, chest and arms. An hour before, she had ordered him to do two things: He had to shave himself like a girl, so he would be smooth, and he had to treat himself with some lotions she had provided, so his skin would feel soft and silky.

"Oh wow, you did a great job for your first try," Janice said, her hands tracing up and down his arms. She reached across his chest, enjoying the feeling of his smooth skin, and she teasingly squeezed one of his nipples as she did.

Charlie let out a soft moan in his girl voice, and that made Janice smile even more. "Oh, you are learning so fast," Janice giggled. She ran her hands down to Charlie's legs and her smile turned into a frown. "Well, you aren't perfect. You missed a small sliver of hair here, on the back of your leg."

Charlie's heart sank as he reached down, following her hand to the thin strip of hair. "Oh Janice, I'm so sorry, please, I'll go fix it, right now," he said, hoping not to see her bad side.

Janice sighed and grabbed his hand with hers, squeezing tightly. "It's fine, don't worry, you won't be punished. Just make sure this is fixed when you shower tomorrow. If I see it again, we might need to have a more... complicated discussion."

Charlie told himself he would just shave the hair off the moment she left, so he wouldn't have to find out what that means. But for her threats, Janice seemed especially tender today. She grabbed him and cradled his naked body against her, his head resting on her breasts.

"I want you to be relaxed today, Charlie. If you aren't, then today may be an uncomfortable day for you," Janice said as they cuddled.

"Uncomfortable how?" Charlie asked.

"Let's just say that you'll be taking a few different tests today, and you'll be doing some things that you've never done before, though I can guess that you've fantasized about it. We'll be starting with your mouth, since that will be the primary way you make love from now. I need to make sure that you can please any man or woman I have you kneel down in front of. After that...well, you'll see what the last test is when we get there."

"How do these tests work?" Charlie asked.

"Mmm, well, let's start with the first one, since I know it's the one you'll love the most. Today, Charlie, you're going to get on your knees and eat me out."

Charlie gasped. "I get to taste your pussy?" he asked, excitedly.

"I knew you'd like that. Now, on your knees," Janice ordered.

Charlie threw himself on the ground, getting on all fours, looking up at her eagerly. Janice giggled at him, at his excitement. She unbuttoned her pants and started to slide her jeans and panties down. Charlie helped her, tugging her jeans down so she could easily step out of them, but he did so without touching her bare skin, since she hadn't told him he could yet.

With her pants off, Janice sat back down on the bed and spread her legs wide, showing her pussy to Charlie for the first time. It was perfect, smooth and sleek slit, and mostly hairless, save for a small tuft of hair right above her clit.

Charlie crawled between Janice's leg and started to move his lips to Janice's pussy, but Janice grabbed his hair roughly and held his head in place.

"Charlie, we need to be clear about this. I am not doing this because I want to be your lover. This is something that I am allowing you to do, mostly for your sake. And the moment your tongue touches my pussy, you lose the choice to say no to anything else I try to do today. Do you understand me?"

Her words stung his slightly, but still, this might be the only chance Charlie had to go down on a girl this beautiful. He had to take his chance.

"I understand, Janice," he said.

"Good, then, you can get started," Janice smiled, and she guided his head to her pussy.

Charlie gently licked at her slit, running his tongue up and down her pussy, then gently sliding it in. Janice started to make little moans of pleasure, and she let him continue for a bit, but she seemed to get bored of his efforts, and she started to give him orders.

"No, no, use your tongue on my clit," Janice instructed, pulling his hair to get him to raise his mouth to her sensitive clit. "Use your hand to finger me, one finger at first, then when you feel it getting wet, ohh, yes, Charlie, like that, that's how you should be using your tongue," Janice said.

She started to grind her crotch against his face as he licked at her clit. He slipped a finger into her pussy as she told him, and was rewarded with a loud groan of pleasure from Janice's lips. He slowly started to fuck her with his finger.

While he fingered her, he decided to try new things with his tongue. He started trying to lick at her in different ways, and found that, while no one way seemed better than the others, she was much louder when he kept changing his pattern, so he started wildly flickering his tongue across her clit in as many different ways as he could.

"Oh fuck, that actually feels good, oh yes, like that," Janice moaned. "Another finger, give me more."

Charlier slipped a second finger inside her, thrusting his fingers in and out of her faster. As he did, Janice lifted one of her legs up and over his shoulder, using it to press against his back and pull him in closer.

"Oh yeah, like that, I'm getting close. Curl your fingers upwards," Janice told him.

Charlie curled his two fingers like she said, and as he fingered her, he felt his finger tips brush past some odd texture inside of her. The second his fingers brushed that spot, Janice let out a scream.

"Oh Ben, Ben, I'm cumming, I'm cumming for you!" Janice screamed. She fell back onto the bed and she roughly grabbed Charlie's hair and pressed him down against her clit. Her leg draped across his back quivered, the rest of her body seemed to shake and convulse as she came on Charlie's tongue.

Charlie kept lapping away, feeling such a mixture of emotions. On one hand, he just made this beautiful woman cum with his mouth. On the other hand, she was clearly thinking of someone else, whoever this Ben was whose name she had screamed. Someone she probably thought of as a real man.

Janice took a few deep breaths and relaxed her grasp on Charlie's hair. "Oh, that was good. On your own, you don't know what you're doing, but you follow instructions so well. I'll have you being a champion pussy eater in no time," she said, smiling down at him.

"T-thank you," Charlie said, as her juices ran down his chin.

Janice took a second to breathe, then she sat back up. "So, we know that you can take care of the ladies, or you will soon be able to, anyway. So that just leaves the men. Charlie, go over to my bag over there and bring me the three items in it."

Janice pointed over by the doorway, where she had left her book bag propped against the wall next to his bedroom door. Charlie crawled over and opened the bag. The first item was a set of leather and plastic straps, Charlie wasn't sure what purpose they served. The next time was a bottle of what was probably another lotion. The last item, however, was a little different.

"Is that what I think it is?" Charlie asked.

"Don't talk, fetch," Janice ordered.

Charlie brought the items over to her and laid them on the bed. The straps, the bottle, and the seven inch long, realistic dildo that Janice had brought with her.

Janice grabbed the straps and looked at Charlie. "This is going to be very helpful for you to know, so I'll show you how this works. First, we need to put the dildo into the strapon, like this," Janice said, sliding the plastic cock into a ring in the middle of the staps.

"Next,I need to put them on like this," Janice slipped her legs through the straps one at a time, until the straps rested around her crotch.

"Finally, I need to tighten the straps. Here, you can help," Janice said, taking his hands and showing him where he needed to tighten the straps so they stayed tightly secured to Janice, while not hurting her.

Janice stood up, towering over Charlie, who was still on his knees. She grabbed the base of the dildo and waggled it in Charlie's face. "Now, it's almost like there's a man in this bedroom," Janice laughed.

"W-what do we need that for?" Charlie said.

"Well, you just ate pussy. It's time to see how good you are at sucking dick," Janice said.

Charlie swallowed, hard, while he looked at the dildo strapped to Janice's waist. "I don't know if I can fit all that in my mouth," Charlie stuttered.

"There's only one way that we'll find out, Charlie. And remember, it's too late to back out now," Janice said.

Janice grabbed the back of Charlie's head with her hand again, and pulled him forward. She started by gently slapping the dildo against his face. "This can help get a man hard if he isn't fully there yet. It can take the big ones a little time to get fully stiffy you see. Now, a man has you like this, how do you react?"

Part of Charlie wanted to just run out of the room, but something else in him was eager and willing to play along. His cock certainly was, as it was rock hard and dripping small drops of precum underneath him.

Slowly, Charlie reached up and wrapped one of his hands around the dildo. He stroked the plastic cock gently, before bringing his lips up to kiss it on the head.

"Mmm, yes, they'd like that, a nice teasing kiss to get things started. What next?"

Charlie licked his lips as he looked up at her, at her patient eyes, and he opened his mouth and slid the dildo into his wet, warm mouth.

"Oooh yes, good, move past teasing and start pleasuring him, good girl," Janice praised him.

Charlie blushed and started to take a little more of the dildo into his mouth. The plastic cock slid over his tongue, leaving an odd taste in his mouth, though it wasn't unpleasant. His hand was stoking the base of the cock while he sucked the head and top of the shaft.

"Mmm, you'd have any man moaning and melting in your hands with this approach. Honestly, your instincts for pleasing men is spot on. Odd that you didn't have those instincts for women...but it's okay to like one more than the other," Janice said as she watched the cock slid in and out of Charlie's mouth.

Charlie started to take the cock deeper, moving his head harder and faster on the dildo. Before he could take the last few inches though, the cock head pressed against the head of his cock, and he gagged, pulling the cock from his lips and coughing.

"A little too eager, it seems. You need to go slow for deepthroating. Try again, and I'll help you," Janice said.

Charlie nodded his head and started to suck on her cock again. She grabbed his hands and pulled them off the cock, and with a firm grasp on his head, she started to press the cock into him. Slowly, surely, the cock was pushing deeper into his mouth.

It started to press against his throat again and once again he gagged, but Janice just shushed him and kept forcing him down on the cock. Charlie felt like he was going to be ill, but then the cock head pressed down into his throat, and the feeling vanished.

Janice kept pushing until the plastic balls of the dildo were pressed against Charlie's chin. The cock was firmly lodged in Charlie's throat, so thick it blocked his throat entirely, and he couldn't breathe.

"Oh my god, your first time with a cock in your mouth, even if it's a fake one, and you deepthroated! Charlie, you're a natural born cock sucker. I don't think I have anything left to teach you here. You may be able to give me lessons someday!"

Janice laughed as she pulled the cock from Charlie's throat. He fell down onto his hands and knees and took several deep breaths. A small string of spit still connected Janice's cock to Charlie's lips as he looked back up at her.

"I-is that it for today?" He asked, his breathing still ragged.

"Oh, no, one last thing. We might as well try this out, since I'm all set up and you're naked. Now, do me a favor and bend over the bed,"

Charlie looked up at her with shocked eyes.

"Don't give me that look. You had to know this was coming. Of course, the men are going to want to fuck your ass. You need to be ready to take them. Now, do as you're told."

Charlie sat on the floor for a few seconds, just looking at Janice's cock. He should say no, he should stop here, this was too much...but he didn't. What he did was stand up and bend over the bed, displaying his soft ass to Janice.

"That's right. This is how a girl gets fucked. Now, let me lube up," Janice said, grabbing the bottle Charlie had brought her. Charlie heard her pop open the bottle, heard a wet, squishing sound as she lubed up the dildo. There was a second of silence, before Charlie felt a cold liquid drop onto his asshole.

He shivered and squirmed, reflexively moving his hips to the side to get away from it, but one of Janice's strong hands grabbed his waist and held him still.

"Listen, you need to trust me on this," Janice said as she pressed a finger against his asshole. With the lube, her finger slipped right into Charlie with ease. "There's no such thing as too much lube when a cock is going in your ass. Lube the cock, lube your ass, lube everything. Okay?"

"O-okay" Charlie whimpered as she fingered him.

"Good. Now, reach back with your hands and spread your ass open for me," Janice said.

Charlie reached back and grabbed an ass cheek with each hand, spreading them wide, exposing his helpless, heavily lubed asshole to Janice.

"There it is. Now, this may hurt a little at first, but just relax and take it," Janice instructed.

She pressed the top of her cock against Charlie's asshole, and at first all he could feel was the weird pressure of the head against his incredibly tight asshole. Then, the head pushed into him.

"Uuuuuhhhhh," Charlie grunted, as her cock pushed inside him, it's thickness spreading him open. It did hurt, not incredibly bad, but Charlie just grit his teeth and took it. It kept hurting as she pushed further in, but it stopped once her entire cock was inside him.

She held her cock there, keeping him impaled on her full length for several seconds. The pain was gone and in its place was a new feeling, a fix of discomfort and pleasure.

Janice grabbed both of Charlie's hands and twisted his arms, pinning both arms behind his back with just one of her strong arms.

"Tell me, where is my cock, Charlie?" Janice taunted him.

"It's...in my ass," Charlie whimpered.

"Where is it?" She asked again.

"It's in my..." As he started to speak, she pulled most of the cock out of Charlie, leaving him with an odd sensation of being empty, then, she roughly thrust the entire length back inside him, "..ass!" he screamed the last word as she impaled him.

"That's right, you're taking it in the ass," Janice laughed at him as she pulled out and thrust back into him again. She moved her hand from his waist to his head, grabbing a fistful of hair and pulling his head back. "My god, you're ass was designed to take cock, to take it this deep and this well on the first try, you're body was built to be the perfect play toy for cock."

Janice started to fuck him harder, with Charlie's well lubed ass easily taking the cock again and again. Each time she thrust in, the head of the cock slammed against that spot Janice had fingered yesterday, and sent sparks shooting through Charlie's body.

"Oh god, Janice, it feels so good, your cock feels so good inside me," Charlie whimpered.

"I bet it does, Charlie. See, you were so hesitant before, look at you now, taking cock and loving it. Accept this, Charlie, accept that this is you, that you were built to please others with your mouth and ass," Janice whispered in his ear as she slammed into him again.

"Oh Janice, I might...I think...I think I'm going to cum!" Charlie cried pathetically.

"You can cum, cum like a good girl, cum all over my dick," Janice said as she put her hand back on his hips, so she could slam into him harder.

Charlie let out a moan of pleasure and his small cock twitched underneath him, shooting its load between him and the bedsheets, soaking the sheets and his stomach with his cum.

Janice gave him a few more hard thrusts as he came, then she stopped. She held her cock inside him for a few seconds, then slowly pulled out, leaving Charlie feeling used and empty.

Janice pulled him down off the bed and back onto his knees, then pressed his head against the bed, just an inch or two from where he came.

"Clean it up, Charlie," she ordered.

Without any fight whatsoever, Charlie started licking his own cum up from the bed, swallowing the salty, bitter seed. Janice calmly ran her fingers through his hair as he worked.

"That's it, such a good job. You need to get used to the taste, most men are going to want to cum in your mouth, so you need to be ready for cum at any time," Janice told him.

Instead of leaving right away, this time, Janice cuddled with Charlie and held him close, her the big spoon, him the little spoon. He felt so warm and safe with her arms wrapped around him. He thought they might fall asleep like this until she finally got up to leave.

"You made such amazing progress today, Charlie. And I want you to know something. If you keep up this good work for the rest of the week, I have a special surprise in store for you. You'll get to something that you've never done with me in the room before," Janice promised.

"What is it?" Charlie asked.

"Just be a good girl, and you'll find out. Have a good night, Charlie," Janice said, gathering her things and leaving.

Charlie laid in his bed looking up at the ceiling. He knew he should feel ashamed of what he let her do to him, but, in reality, he could still feel the effects of that amazing orgasm she'd given him, and he couldn't wait to see what came next.