Changing Sides 1

By DickDerkley.

Charlie sighed and flung his backpack onto his bed. He walked over to his computer desk and fell into his computer chair, drained after another day of college. His brain felt overloaded, but somehow, he was just barely able to keep a handle on it.

It was the late afternoon right now. Classes were done, and by some sheer luck, he had no homework to do tonight. He was completely free. Should he read a book? Call a friend? Watch a movie? As he pondered his choices, he came to the same conclusion he always reached when he was alone: He should tug one out. And so, he quickly dropped his pants around his ankles.

He had loaded up some vanilla porn, watching some man with a monster cock slamming his manhood into some ninety-pound barbie while she wailed her fake moans, but that just wasn’t doing it for him today. He even watched a few of the old favorites, videos that had never let him down before, but even those videos failed him, his cock going limp in his hands as he watched.

With a sigh, he loaded up that site, the one he told himself that he was going to stop using. As soon as the site loaded, his computer screen was bombarded with images of men and women in all kinds of sex acts, with text written across each image.





Charlie’s cock twitched back to life, and he started stroking in earnest. He could feel himself approach orgasm almost immediately, so he slowed and stopped, waited a few seconds, and started to jerk himself again to a new set of images.

He didn’t know why, but these pictures always did it for him. He didn’t think he was gay, he never checked out guys at the gym or anything, but when he looked at these pictures, he couldn’t help but think about how much fun it would be to be a girl, to play with a man’s cock, tease it, feel it tremble in his hands…

It didn’t matter, though. This was just a jerk-off fantasy. He would never act on it. Even if he knew how to put together an outfit and how to paint his face with makeup, he knew he’d die of embarrassment the moment he stepped foot outside his apartment looking like a girl. He wouldn’t be able to make it far enough to talk to a cute guy, let alone flirt enough for it to lead anywhere.

He scrolled through, grabbing a fresh set of images, and started stroking his cock faster. He was getting so close, about to let go, when he felt a strange pressure on his head. His headphones had turned just a little, moving enough so that they didn’t cover one ear.

“This is pretty hot,” A voice whispered in his ear.

Charlie nearly jumped out of his skin as he turned around. Standing behind his computer chair was a woman, a friend of his from his college Econ class named Janice.

Janice was taller than Charlie by over two inches. Her body was tight and toned from years of playing competitive sports, like tennis and track. Despite her athletic body, she had a pair of magnificent breasts, each a handful with plenty to spare. She was wearing one of the fairly conservative outfits she liked to wear, a tight-fitting sweater matched with a long, flowing skirt.

“Janice! W-what are you doing here?” Charlie said, mortified, still holding his cock in his hand.

“You told me to come over to study for the quiz this Friday, remember? The front door wasn’t locked, so I let myself in. Though, it seems you’re studying something much more fun,” Janice said, smiling and staring at him. “I didn’t know your tastes were so…unconventional.”

He and Janice had been cordial but cool since they met. They often met to share notes and study for their class, and Janice was always polite, but she always seemed to look through him. Not in a disdainful way, but like he just didn’t register to her at all. But now, she was looking at Charlie like she was seeing him for the first time.

“I’m so sorry, and it must have slipped my mind. I never meant to let you see me like this,” Charlie said in a panicked voice, his face turning a deep red. Charlie moved to tuck his cock into his pants, but Janice slapped his hands.

“No, don’t move yet,” She ordered

“Janice?” Charlie asked, shocked, but he stopped, just as she ordered.

Janice leaned over him, her face just a few inches from his. She grabbed his jaw and moved his head from one side to the other. “Hmmm, yes, such delicate features, such tender skin,” she muttered. She slid a hand up to his shirt and explored his chest with her hands. “Almost hairless, not pudgy, but soft, and warm…”. Her hand lowered to his cock, where the tips of her fingers brushed against his cock. “Small and thin…almost like it’s not a cock at all…”

Charlie blushed as she ran her hands all over him, but did nothing to stop her. “What do you mean, so small?” he asked.

“Oh, Charlie, I’m not trying to be mean. It’s just a little small is all, please, don’t be offended. In fact, it’s one of the reasons this is all making sense,” Janice said, smiling.

“I don’t understand, Janice. What is making sense?” Charlie asked.

“The fact that you want to be a girl, silly,” Janice said.

“W-what? I don’t want to be a girl. I’m a guy,” Charlie said.

Janice laughed. “Oh, Charlie, please. Explain that, then,” Janice said, pointing to an image on his monitor.

The image showed a blonde woman on her stomach. A man was mounting her from behind, his hands on her waist, his thick cock in the process of sliding into her ass. At the bottom was a string of text:


Charlie could feel his face turning an even darker shade of red as she pointed at the image. “I-I can explain, that’s just, just a fantasy, I would never do it, I couldn’t, I wouldn’t know how even if I wanted to,” he babbled.

“‘I’ll show you,” Janice said.

“Show me? Show me what?”

“I’ll show you how to be a girl. I’ll show you how to dress, how you should walk, how to talk like a girl. I’ll show you how to do your makeup, how to make yourself look cute, and how to make yourself look sexy. And when you’re ready, I could even show you how to please a man,” Janice said.

“Janice, no, that’s crazy. I can’t do that. I’m a boy,” Charlie meekly fought.

She grabbed his head in her hands and pulled him to face her. She locked eyes with him. Her gaze was so intense that Charlie wanted to look away but was worried about how she would react if he did.

“Charlie. Tell me the truth now. Tell me that there isn’t even some small sliver of yourself that wants to be a girl. Do it now, and I’ll leave, and we’ll never talk about this again,” she said.

Charlie’s lips moved, but no sound came out. “I…I don’t…” he tried to say, but the words caught on his tongue. He lowered his eyes without ever denying it.

Janice smiled and patted his face. “Good girl,” she said. “Now, I’ll give you a choice. I can walk out of here and tell everyone at school what I saw. That would be embarrassing, but eventually, things would go back to some form of normal for you. That would tell me that you’re a boy who is just a little confused.

“Or, I could start helping you. Day by day, you’ll learn more about being a girl, starting tomorrow. I’ll even help you finish up, here and now, to get you excited about it. That would tell me that there is a girl inside you, Charlie, and we can start letting her out.”

Charlie considered his options. If word of this got out, he would be ruined. He’d probably need to move, and that meant changing schools, which meant delaying graduation. On the other hand, he didn’t know what Janice meant by ‘helping.’ She had mentioned learning to please a man. Did he want that? He masturbated to the fantasy, but would he enjoy the reality?

And then there was the promise of help…maybe he could just pretend to be into this, to see what Janice would do to him? He would give anything for even a glance under that sweater. What if this was his chance?

“Make a choice!” Janice said in a forceful voice, just a few shades quieter than a shout.

“Help me, I want you to help me,” Charlie said, squirming underneath her.

Janice smiled at him. “See, I knew that’s what you wanted. And I’ll be here to guide you. But that can wait. Right now, I want to see you start to play with yourself again.”

Charlie grimaced. “I thought you were going to, ah, help me out?”

“Oh, I will, but I won’t be touching you there today. No, here, I’m just going to motivate you,” she teased.

Janice walked across the room, grabbing a spare folding chair Charlie had, and she set it up next to his computer chair. She sat down next to him. One of her hands gently cupped his face, pointing him back to the monitor, while the other hand grabbed his mouse. She started to scroll through the images, finding some that seemed to please her.

The first was an image of a perky girl down on her knees, with a massive cock being pushed into her mouth. Janice brought her lips to Charlie’s ears and read to him, in a low and sultry voice, the text on that image.

“You know, deep down, that you belong on your knees,” she whispered in his ear.

Charlie’s cock was rock hard, and he started to play with himself, wrapping his wrist around his small cock. He took slow, teasing strokes as Janice selected another image, this one of a girl laying on her stomach. She’s dressed in black lingerie, sheer and lacy. A thick cock is gently nestled between her ass cheeks.

“Accept every inch of his hard cock. However, he chooses to give it,” Janice says.

Charlie’s hands started to work faster now. He was desperate for release. He had teased himself a few times before Janice interrupted him. Janice herself raised the whole thing to another level, one that Charlie could barely stand. Her warm hands against his face, her sexy voice singing temptations into his ear.

“Oh, Janice,” Charlie whimpered.

This one had a woman bent over a table, her eyes closed, a huge, blissful smile across her face. A man was behind her, grabbing her by her hair, clearly railing her from behind.

“Just submit, and give your body up to a real man,” Janice said.

Charlie let out a groan. “I’m so close, Janice,” he moaned.

Janice grabbed his face and, and she stared into his soul once again.

“Tell me you’re my good girl,” Janice ordered.

“I’m a good….girl,” Charlie muttered, still playing with himself.

“Louder,” she said.

“I’m a good girl,” he said, louder this time.

“Louder!” She shouted.

“I’m a good girl!” Charlie cried. As soon as he said the words, Janice leaned in and pressed her lips against his, kissing him wildly.

Charlie was completely caught off guard by the taste of her lips on his, and it drove him over the edge. He came all over his hands. Thin ropes of watery cum splashed down his fingers. His stroking slowed, his breathing was heavy and labored as he came down from his orgasm.

“Mmm, you are a good girl,” Janice said. She lowered her hand and dipped two of her fingers in his cum. She started to raise them, hesitated, and ultimately decided to rub the cum into Charlie’s sleeve.

“W-what are you doing?” Charlie asked.

“Oh, that’s something you’re not ready for, not yet anyway,” Janice got up from her chair and stood over him, smiling down at him as he sat before her, still covered with his own seed. “This was a nice introduction, you’ve done well so far, but tomorrow, you’ll be taking your first real steps towards being a girl.”

Janice patted Charlie gently on the head. “I’ll see you tomorrow, then. Oh, but before I leave, I need you to make a promise to me,” Jance said.

“Oh, what promise?”

Janice gave Charlie’s softening cock a quick squeeze. “When I’m coming over, you don’t play with yourself. Maybe after I leave, you can play with this, but never before. You understand me?”

Charlie gasped as her soft but strong hand pressed against his sensitive cock. “Y-yes Janice, I promise!” he muttered.

“Good girl,” She said. “Now, goodnight, Charlie,”

Charlie waved to her with his cum stained hand as she left his room. He heard her pull the front door open and slam it shut behind her. After she left, he started pulling out tissues to clean himself up with. As he did, his mind turned to thoughts of Janice, the feel of her hand, the sound of her voice in his ear. He couldn’t wait to see more of her.

At the same time, he couldn’t help but wonder what he’d gotten himself wrapped into.


Charlie sat in his computer chair, watching as Janice started laying out piles of clothes onto his bed. “Do I really have to try on all of that?” he asked, anxiously.

Janice let out a laugh. “No, silly. I’m just going to use these to throw together a few simple outfits for you. We’ll need to see what looks good on you.” she said, pulling out a small pile of shirts, placing them on the bed, then neatly flattening out their wrinkles.

Janice had come over right after their classes, just as she had promised. She actually arrived at his apartment just a few minutes after Charlie himself, wheeling in a large suitcase behind her. The moment she arrived, she ordered him to sit and wait in his chair while she got things organized.

Janice peered into the suitcase and saw she had finally emptied it. Stacks of shirts, shorts, skirts, stockings, and socks sat upon the bed, along with other clothes. Her task done, she turned to Charlie with a smile on her face.

“Now, get up,” She ordered. He leaped to his feet, standing before him. She was only a few inches taller than him, but she seemed to tower over him.

“So obedient, I like that. It’s going to make this whole process so much easier. Now, we’re going to get you dressed up like a girl, but first, I need you to strip down,” she said.

“Y-you mean, you mean, you want me to take off everything? Charlie protested.

Janice sighed. “So much for being obedient. Yes, strip down. What are you even worried about? I caught you red-handed yesterday, and it’s not like I’ll see anything new.”

Charlie blushed as he remembered. She was right; of course, she had seen pretty much everything there was to see the other day. There wasn’t much harm in letting her see the rest of him.

“Okay, I’ll do it,” he said. Janice simply gestured with her hand for him to hurry up.

He started by pulling his shirt over his head and tossing it on the ground, revealing his pale, mostly hairless chest. He unbuckled his belt and let his pants fall to the ground, revealing his boxers and his scrawny legs. He put his hands on his boxers, and he hesitated for just a moment.

“Now!” Janice snapped, and he quickly dropped his boxers, exposing his small cock to her.

“Ok, so, let me see what it is we have to work with here,” Janice said. She walked around him, running her hands around his body. “Mmm, this is nice. I like your body.”

“Y-yeah?” Charlies asked.

“Oh yeah. So slender, so pale, your skin is so soft. You’re mostly hairless, and there’s still a little fuzz. We’ll need to deal with that. We won’t need much work to make you into the pretty girl that you know you are. Do me a favor, though? Can you bend over the bed?”

Charlie was confused by the request, but he did as he was told, bending over the bed for her, pushing out his ass. Janice’s strong hands cupped Charlie’s ass, squeezing it gently. She used her hands to spread his ass. Charlie shivered as the movement exposed his asshole to her.

“Oh yeah, this is good. I know a lot of people who would love to have your ass bent over like this,” Janice teased. She put her hands on his waist and gently thrust her hips against his ass, giggling as Charlie squirmed underneath her. She slapped his ass hard, then told him, “Ok, now get back up. It’s time for your fashion show.”

Charlie rubbed his ass as he straightened his back. He wasn’t used to being slapped like that, and Janice had slapped him hard enough to leave a pink mark on his pale skin.

“So, how do we start…this,” Charlie asked sheepishly.

“You’re going to get dressed that way that you normally get dressed, Charlie. You start with your underwear, right? Here, I think these three are a good choice for you. Which do you like?”

Janice placed three panties on the bed in front of Charlie. The first was a simple set of white cotton panties with a small red rose on the front. The next set of panties were jet black but outlined in dark purple. The last set of panties were bright pink.

Charlie looked at each one, then, slowly, he reached down and grabbed one. He held his chosen panties, the bright pink ones, up before Janice.

“These seem cute,”

“Pink, huh? It is a classic. What are you waiting for? Put them on,” Janice said.

Charlie blushed his hands still. He felt like he wanted to put them on, but he just couldn’t. Something, some sense of shame or peer pressure, weighed down on him. Even if no one found out, he would always know that he’d worn panties, and worse, panties he’d chosen himself.

“What’s the matter?” Janice said frowning.

“I…Janice, I can’t, this is too much,” Charlie protested, handing her back the pink panties.

Janice put her hand on her face. “And things were going so well. I should have seen this coming,” she muttered to herself.

“I’m sorry, I didn’t mean to lie to you,” Charlie said.

“It’s not me you’re lying to,” Janice said. She put her hands on his waist and pulled him in close, her lips just an inch away from his own. “I know I’m right about you. I know you want to be a girl.”

“But-” Charlie started to protest, but Janice quickly shushed him.

“No, listen. I know this is a big change, and I know change is scary. But trust me, this is the right thing to do. And I know how to help. If you put on the panties and the rest of your girly clothes, I’ll make you cum. Not by whispering in your ear, no, you’ll get to feel what my hand feels like tonight.”

As she said that, Charlie’s cock started to twitch, pressing against her shirt eagerly. Janice smiled down at him, “Looks like someone’s excited. So, will you try them on? For me?” Janice asked.

Charlie nodded his head, and Janice giggled at how quickly he’d changed his mind.

“Then put them on,” she said, pressing the pink panties into Charlie’s chest. She took a step back to watch.

Charlie meekly took the panties. He raised one leg, slid it into the panties, then the other, and pulled the panties up around his waist. They fit rather well, clinging to his body, and they easily contained his small cock.

Janice clapped her hands together. “Such a good girl,” Janice cooed. “Now, let’s get you a full outfit. Here, I have a few ideas.”

Janice put her hand on his ass and directed him back to the bed. “Now for shirts, here are a few choices. Notice it’s light colors. We don’t want to clash with your pale skin. Well, unless you want to go through a goth phase.”

Charlie looked down at the shirts. There was a black tank top, a pink button-down blouse, and a babydoll tee showing the name of some band Charlie had never heard of. Charlie felt the blouse was too much work, and since he didn’t know the band name, he figured the tank top was the safest choice. He grabbed it and pulled it over his head.

“Look at you? No hesitation now, I see,” Janice laughed. “I like it. Simple and casual. Hmm, I was worried my clothes would be too tight on you, but it looks like they’re too loose! We’ll need to get you some clothes of your own before you go out in public, You can’t look like a mess when you’re looking for a guy, but these will do for now. Time for your next choice!”

Janice lays out a set of bottoms for him. There was a pair of hot pink booty shorts, a knee-length blonde skirt, and a set of light brown capri pants. Charlie almost grabbed the skirt, but instead, he grabbed the pink booty shorts. He slipped them with ease.

“Pink again, huh? It sounds like you’re a really girly girl. I’ll have to keep that in mind,” Janice teased him. “Come here, take a look at the new you.”

Janice pulled him over to his dresser, where he had a small mirror set on top. Charlie never put much thought into his clothes before. The mirror was mostly used to make sure he hadn’t missed anything when shaving. But now, he could see himself.

“Oh, wow,” he muttered.

His face still looked like a boy’s face, with the fuzzy stubble along his jaw, and his hair wasn’t long enough to be girly. But moving down his body, his masculinity became less obvious. His thin arms and legs looked naturally girly. Janice’s clothes were indeed hanging loose on his body, but, in his case, it worked to his advantage, making it look like he may be hiding a pair of small breasts underneath his shirt.

He looked more like a girl in one day than he ever thought he would.

“I know, right? You were built for this, Charlie. A little makeup, maybe a wig, and I could take you out today to pass as a girl. But we both know you’re not ready for that. Well, what do you think? Janice asked.

“I like it,” he said quietly.

“Oh? And why do you like it?” Janice pressed.

“I like it because…because I look pretty,” Charlie confessed.

“Mmm, that’s right, you do. And trust me, you’re only going to get prettier from her. Soon enough, no one would ever be able to guess that you once pretended to be a man.” Janice said.

Her words confused him, both stinging him and stirring something inside him that he often tried to bury.

“Now, are you ready for your reward?” Janice asked.

Charlie eagerly nodded his head, “Yes, please, Janice,” Charlie said, his cock still rock hard, precum starting to leak into his panties.

Janice walked over to the bed and sat down, then she patted her thighs. “Come on, sit down here and let me take care of you,” She said, smiling at him.

Charlie walked over and sat down on her lap as a woman would sit on a man’s lap. He uncomfortably squirmed underneath her. Janice reached down, unwrapping him like a present as she pulled his booty shorts and panties down around his knees. His small cock was rock hard and ready for attention.

“Are you ready for this?” Janice asked.

“Yes, Janice, oh god, I can’t wait to feel your hand around my cock,” Charlie whimpered.

Janice slapped his cock, and Charlie whimpered in pain.

“No, no, no! And you were doing so good,” Janice said, displeased. “Remember, you don’t have a cock.”

“But I-” Charlie replied, but Janice cut him off.

“No, you don’t. If you had a cock, I’d need my full hand for this. But I only need a finger or two for a clit,” Janice said as she lowered her hand. She used two fingers and started to rub them against Charlie’s cock.

Janice started to move her fingers along Charlie’s shaft, easily rubbing up and down his entire shaft in quick, circular movements while pressing his cock down against his crotch. The sensation was so bizarre, but Charlie couldn’t help but groan as she rubbed against him.

“That’s not right, either,” Janice said, slowing her fingers. “Girls’ moans are higher pitched than that. Give me a good, girly moan.”

Charlie blushed but did as he was told. “Ohh Janice, your fingers feel so good,” he moaned in a high pitched voice.

“Mmm, my fingers feel so good where?” Janice asked.

“On my…on my clit,” Charlie said in his girl’s voice.

“That’s right, good girl,” Janice said. She started to move her fingers faster, bringing Charlie to the edge, but she sensed him approaching his limit and slowed down yet again.

“Open your mouth,” Janice commanded.

Charlie immediately opened his lips, and Janice raised her other hands to his mouth, sliding two fingers between his lips.

“Suck and lick my fingers, get them nice and wet,” she told him.

Charlie started to wiggle his tongue over her fingers, moaning onto them as she kept going with her cycle of teasing him, then letting him cool down.

Eventually, Janice pulled her fingers from his lips and brought them down and around Charlie, out of his sight. She stopped touching him altogether, and she leaned in close, talking directly into his ear.

“Something is about to happen. You are going to relax and take it. It might be uncomfortable, but it needs to happen before I let you cum. Do you understand?” Janice asked.

Charlie nodded his head. His small cock was swollen and leaking precum, and he was so eager for release, he would let her do anything to him to get it.

“Good girl,” Janice said. She started rubbing his cock again, but her other fingers started to slide between his ass cheeks as she did. A finger started pressing against his asshole, and it was pressing hard.

Charlie’s eyes go wide, but before he could react, Janice’s voice filled his ear.

“Remember, just take it,” she said, and one of her fingers slid inside him. “There we go, what a good girl. That’s what a good girl does, let’s others inside her body.”

The finger in his ass felt uncomfortable at first. It was slowly wriggling its way deeper inside him, violating him in a way no other person had before, but the fingers on his cock just felt so good. He needed this. He had no choice but to take it.

Janice’s second finger slipped in as well, and together, the two fingers started pushing deeper inside her. Charlie’s tight ass clenched down hard on her fingers, making her progress slow, but she found what she was looking for.

Charlie’s eyes went wide, and a loud moan escaped his lips. “What is that feeling?” he whimpered.

“That’s your g-spot,” Janice said. “Doesn’t it feel good? It’s okay if it does. You’ve been such a good girl. You can cum whenever you want to.”

The fingers inside him kept brushing against that special spot inside his ass, and the fingers on his cock started rubbing furiously. It was too much.

“Oh Janice, Janice, I’m cumming!” Charlie screamed, and his cock started to twitch, and he came. Not only did he cum, Charlie came harder than he ever had before, his cock exploding out thick ropes of cum, some of which splattered against his new clothes. The rest landed on Janice’s fingers.

Charlie’s breathing was deep and ragged as he rested himself against Janice, exhausted. Janice stopped moving her fingers, but the two fingers in his ass stayed where they were.

Janice raised her hand to his lips. It was the hand that she’d rubbed his cock with, and they were covered in drops of his seed.

“You did so well today, Charlie, but there’s one more thing. I need you to taste this,” Janice said.

Charlie looked her in the eye. “Do I really need to?” he asked, almost pleaded with her.

“You need to get used to the taste. Just give it a lick. That’s all you need to do,” Janice said.

Charlie lowered his mouth to her hands and opened his lips. He used his tongue to lap up a small droplet of cum, and his mouth was full of the salty, bitter taste of his own semen. He didn’t hate it but couldn’t help but be embarrassed at being forced to taste his own cum.

“What a good girl. You’ll thank me, trust me, you want to be used to the taste before a man explodes in your mouth. I almost threw up when I first had to taste it,” Janice laughed. As she did, she slowly pulled her fingers out of his tight ass.

Janice gently rolled Charlie over onto the bed and off of her lap. She went through the remaining piles of clothes and picked out a few different outfits for Charlie while he took the time to compose himself.

“I’m going away for a few days,” Janice told him. “We’ll take the next step when I come back. In the meanwhile, Charlie, I want you to keep dressing like a girl around the apartment. I put these together for you, but feel free to dress. You did a good enough job the first time around. But you will send me a picture of you dressed up every day.”

“What happens if I don’t?” Charlie asked.

Janice looked down at him, contempt in her eyes. She stood over him on the bed, raised her shoe, and placed it down on his now flaccid cock.

“You don’t want to know what happens when you disobey me,” she said.

“No, I got it, pictures every day,” Charlie said, panicked.

“Good girl. Now, don’t get up. I’ll show myself out. And trust me, Charlie, you’re going to love what we’re doing next.”

With that, Janice flashed him a vicious smile and left his bedroom. As she left, Charlie didn’t know if he was more excited or afraid of what comes next.


To be continued…?


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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