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 like it was 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.
SEE HOW GOOD IT FEELS TO GET ON YOUR KNEES AND SUCK COCK.
SATISFY YOUR NEED TO EAT CUM
WEAR HIS SEED WITH PRIDE
DON'T WORRY, IT'LL START TO FEEL GOOD WHEN HE GOES FASTER
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, 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 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:
IT FEELS GOOD TO BE FUCKED LIKE A WOMAN
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 make up, 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, Charlie wanted to look away, but was worried 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 masterbated 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 quick 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 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 Charlies 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, then 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, he 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.