So he leaned forward and typed a message. “Send a picture of your cock,” he wrote. Though he wasn’t sure why he wrote it. It was only ten seconds later when a picture of a thick, throbbing erection appeared on his screen. And strangely, the image made a tingle grow in his cock. Was he gay? Did dressing up like a sissy suddenly turn him into a queer?
He looked down and saw that his bulge was truly expanding. But he wasn’t attracted to the cock. The thought of a juicy pussy was still far more enticing than any cock. It was the idea of the man’s erection—knowing that he was sexy enough to make it happen. He closed his eyes and continued to plunge that cock in and out of his butt. He was getting hard now, more than hard enough that he could grab on and jerk himself off. He made sure he had lots of lubricant in the palm of his hand, so that the sound would be satisfying: squish, squish, squish!
He gripped his cock tight and beat hard, still with that dildo moving up and down inside of his asshole. It felt good—very good. He could feel that orgasm approaching. Now he just had to figure out how to come into his mouth. He knew he wasn’t flexible enough to lean forward and catch his goo with his mouth. He was going to have to ejaculate upside-down. So he rolled over and got up onto his shoulder blades. It was uncomfortable, but now his cock was pointing directly down into his mouth. Gravity would do all the work for him. He closed his eyes and kept beating his cock, breathing heavily as he felt that euphoria growing stronger and stronger.
“Shit,” he muttered. He opened his eyes and saw that his tip was dark red and his cock was bloating thick. “Oh God.” He strained and felt all of his muscles contract—and then his cock began to blast and unload. He opened his mouth, but only a little bit made it through his lips. The rest coated his face with long white streaks. It didn’t taste great: like uncooked pancake batter. But he didn’t mind. It was definitely worth making a hundred extra bucks on top of all the money he was already making. He sat up slowly, a little bit dazed, and saw that his customer had left him an additional fifty-dollar tip.
“Thanks,” he said in his best female voice. And it didn’t sound so bad, though he knew it needed work. He went back to his regular chat room, which still had hundreds of people waiting in it. Comments immediately started to pour in regarding the white mess all over his face. People loved it. “Is that really her cum? Fuck, she’s so hot!” said one man. “That’s so much cum! It can’t be real!” said another. “It’s real. And it was worth every dollar,” said Charlie’s paying customer.
And then Charlie looked down and realized his cock was still hanging out the side of his teddy. He reached down and slipped it back into the safety of his outfit, and then he smiled for the camera. Tips were rolling in fast. “Wipe it up and eat it!” said one man. So Charlie wiped the cum off of his cheek into his mouth. More tips came in. Charlie broke his previous record that morning, making nearly twenty-five hundred bucks in just a couple of hours. He was reluctant to stop his stream, but he knew that he needed to get himself and his set cleaned up, and he needed to give his audience something to be excited for. He couldn’t just make himself available twenty-four-seven.
He got himself cleaned up in the shower. He dragged all of Susie’s soiled outfits down to the laundry room, started a load, and then he made his way back up to his apartment to make some lunch. While his lunch was cooking, he tuned into Susie’s show, which had just begun. Susie was with another female friend now. Her friend was completely naked, and her fans were voting on what Susie would do to the woman. It only took five minutes for the group to decide that Susie should peg the girl with a strap-on, so Susie got a strap-on fastened around her hips and then she went to town, making the girl moan and scream and squirt. It was a good show. Susie knew how to please her fans, and she knew how to make a whole lot of money.
CHAPTER VII
After just two weeks, Charlie had enough money in his bank account to live for a year. He couldn’t believe the number he was staring at on his bank statement. Even if he had managed to get a job working as an art director, he wouldn’t have been making nearly this much—even after a decade of career building.
And his show was quickly becoming popular. There would be dozens of men already in the chat room on his channel before he even clicked that ‘GO LIVE’ button. And once that button was pressed, it only took five minutes before hundreds of people swarmed over to his channel, ready to toss tips his way. He even found to be fun, teasing his audience, and then doing whatever they wanted for the odd private show. It was always exciting to find out what depraved act someone was willing to pay for. It usually involved coming into his own mouth, though he got some more original requests from time to time as well. One fellow had him come on a dildo and then press it up his ass. It seemed weird at first, until that fake cock was in his ass—then it felt strangely nice. Another man paid Charlie a lot of money to come right on the lens of the webcam. And then there was the guy who wanted Charlie to come on his own feet and then squish the cum between his toes.
He didn’t mind the weird requests. He didn’t even mind the especially weird requests, as long as people were willing to pay. The hardest challenge he received was from a man willing to pay three hundred bucks if Charlie could get two dildos into his ass at the same time. He managed to do it, though his ass was sore for the rest of the day. In the time it took him to wriggle those fake cocks into his ass, he probably could have done three whole private shows, netting him more than three hundred bucks—but it was fun to do something different, and it was interesting to see how far he could go.
Charlie got most of his inspiration from his Europe-bound roommate. He tuned into her show every day and watched with surprise as she raised the bar. She was always raising the bar, always shocking Charlie and the rest of her audience with exciting new surprises. It was no surprise that she was one of the top webcam performers on that popular website. She was in Amsterdam when she got four other webcam girls to stand above her and squirt on her while she had a vibrator in her pussy, which was literally controlled by the audience. She had it set up so that the more they tipped, the harder it would vibrate. She made a lot of money during that show—probably as much as Charlie was making in a week. But he wasn’t jealous. She deserved it for putting on such a fantastic show.
It was a Thursday afternoon when Charlie tuned into her show—not to watch, but just to make sure that she was still on her trip. Her stream went live at its usual time. She was doing a solo show in her fancy hotel room, with a view of the Eifel Tower out her window. She had a series of suction-cup dildos lined up on the floor and she was going to make sure they all entered her body at some point during her broadcast. Charlie didn’t stick around to watch. He had his own show to put on, and he wasn’t ready yet.
Though his makeup was still done from his morning broadcast, and he hadn’t taken off his wig. Most days he just left everything on. It was easier that way, and he kind of liked the way he felt in the female garb. He liked catching the odd glimpse of himself in the mirror when he was cooking his lunch, and he liked seeing the reflection of a sexy woman whenever his TV went black for a second or two between commercials. So for his afternoon show, he didn’t need much to get ready: just a few makeup touch-ups and a new outfit.
He had a few of his own outfits now, which he’d purchased online shortly after starting this crazy endeavour. He had a few more on the way. But Susie still had way more—an almost infinite selection of lingerie that she must have accumulated over many years. Charlie liked going through her racks of sexy outfits. It was fun, discovering new things he never noticed before. And it was always fun trying the outfits on. He would still find himself in states of shock whenever he looked at himself in the mirror, in a new outfit, still surprised by how feminine he was able to look, and how perfect his curves were. He was really starting to think that he was born to play a woman on camera—even though that seemed so pathetic.
Over the past few days, he had even started to think of a career plan. He knew he wouldn’t be a
ble to do this forever. He knew he would look too old for the part in just ten years—maybe a little bit longer if he took good care of his body. But he knew that ten years was lots of time. He could accumulate quite a bit of cash in ten years—maybe even enough to retire early. Or maybe he could invest it carefully.
That afternoon, he decided he would do a sort of nod to Susie—to MissyBunny69. He found one of her classic bunny outfits in her closet, complete with ears and a white cotton tail. He found a high-resolution picture of her on the Internet and he used it as a reference for his makeup. Then he decided to move his computer and webcam over to Susie’s room. His plan was to tell his fans that he’d just spent the day making a replica of her room, and that it wasn’t actually the real MissyBunny69 bedroom. He dragged a few lights over and moved a few things around, just so that it would look slightly different in case some fan got the idea to run over to Susie’s stream to rat Charlie out.
He looked at himself in the mirror, smiled, and took a deep breath. It was time to press that ‘GO LIVE’ button. He reached out for it and then he clicked. He took a few steps back and then hopped up onto Susie’s bed. He already had twenty viewers. He smiled and waved at them before beginning to sway to the music. And then he heard a thump. He froze. That thump sounded like a door closing, but it was too loud to be some other door across the apartment hallway. It sounded like it was his front door, but the only other person who had a key was Susie—and his building manager.
Charlie looked at his screen and saw that there were fifty people now watching, waiting for him to break free from his state of frozen terror. Was it really his building manager, letting himself into Charlie’s apartment? He couldn’t do that! He needed to give at least two weeks’ notice! Charlie sprang to his feet. And then he heard footsteps approaching the bedroom door. And he heard something else: a pattering, like wheels on his hardwood floor, as if his building manager was dragging a suitcase. But why would his building manager be dragging a suitcase.
Charlie watched as the brass door handle suddenly jiggled and he heard that spring tightening as that handle was turned. He was about to be caught wearing women’s clothing and makeup—but who was about to catch him?
CHAPTER VIII
The door opened and Charlie stumbled back. His lips parted but he couldn’t muster up any words. His skin was suddenly cold and all of his joints and muscles were frozen and locked. He was staring at Susie, who was supposed to be in Paris, doing a show for her thousands of fans. He’d just seen her on his computer screen, not even thirty minutes ago. How could she be in two places at once?
Susie was frozen for only a moment before shouting, “Who the fuck are you and what are you doing in my bedroom?” She quickly pulled out her phone. “I’m calling the police.”
“Don’t!” Charlie managed to say, having to strain to push that single word past the lump in his throat. It didn’t help that the word came out in the female voice that he’d been practising for weeks now.
Charlie also managed to take a step closer to Susie. She threw her hand up and said, “Stop! Don’t come any closer, you psychopath!”
Charlie tried to swallow that lump in his throat, but it refused to go down. So he bit down hard on his tongue and said, “It’s me. It’s Charlie.” But the words still came out in his female voice. They were enough to make Susie pause. She still had her phone in her hand, and that phone was still dialling the police.
“911, what’s your emergency?” said the quiet voice inside of her phone.
She hesitated, and then she brought the phone to her ear. “Sorry, there was a mistake. My roommate came home early from work and I thought he was a burglar.” She hung up the phone and continued to stare at Charlie. Her gaze burrowed into his bones, tingling his nerves, making him feel weak and pathetic. He was humiliated, standing half-naked in her lingerie and makeup and wig. He felt even more humiliated when he remembered his webcam was still broadcasting this embarrassing incident to all of the fans he’d accumulated over the past couple of weeks.
“What are you doing here?” she said, looking around.
Charlie’s legs trembled. He closed his eyes and wished the nightmare would end. He wished he would wake up in his bed and his life would be back to normal, with his crappy job and the roommate he hardly knew existed. Why couldn’t he have that life back? So what if he hardly made any money? So what if the bills were stacking up? At least he was sane. At least with his old life, he never found himself standing in front of his roommate while wearing her lingerie. “I—I can explain,” he said. His throat was dry and scratchy.
“You started your own show?” she said.
“I—um—yes, sort of. I mean, yes.” He didn’t know what to say. He really couldn’t explain. He couldn’t even remember how all of this nonsense started in the first place.
“Why?” she said.
Charlie shrugged his shoulders. “I did the math,” he said. And it was the only answer he could come up with.
The room became silent, probably just for five seconds, but it felt like a gruelling hour. “And why are you in my room?” she said.
“It was supposed to be an homage. I thought you were in Paris. Your stream—you were in Paris just a few minutes ago.”
“I recorded that yesterday so I wouldn’t miss a show while I was travelling.” Charlie’s gut turned. He had no idea that was even possible. That gruelling silence returned. She stared at him, up and down, looking like she was trying not to laugh. His computer dinged as someone left him a tip—probably a joke tip, just to make the situation more awkward. And until that moment, Charlie had forgotten that he was live. “Are you live right now?” she asked.
He nodded his head slowly.
“Well go ahead. Don’t let me ruin your show,” she said. She put her suitcase down by the door and then she leaned against the doorway with a big smirk on her face. “Go on. Just think of me as one of your regular viewers.” She leaned over and peeked at his screen. “Almost two hundred—not bad,” she said. “Just think of me as one of them.”
But it wasn’t so easy—and not just because she was his roommate, and she knew him personally. It was awkward because she was in the room. He could see all of her reactions. He could see her smirk and he knew she was judging him. At least he could imagine that all of his other viewers were doing nothing but drooling at the sight of him, wishing they could ravage his body—with no judgement whatsoever.
Charlie slowly got himself back up on the bed. The music was still playing, so he started to sway. His body was stiff. He probably looked ridiculous. He felt like he was being punished—Susie’s punishment was utter humiliation, even though he was just doing exactly what he would have been doing had she not shown up.
He wasn’t able to get into the zone. Even when he turned around to shake his butt for the camera, he could feel Susie’s tongue-biting gaze looking his way. He could even hear the occasionally little release of air from her nostrils, as if she was subtly scoffing at him, mocking his routine, which was just a bastardized version of her own routine. He could feel that his face was turning dark red. He just wanted the torture to end. He wanted the nightmare to be over with.
“Loosen up a bit. Are you normally this tense, or is it because of me?” Susie asked.
“You’re not helping,” Charlie said as butterflies fluttered in his gut.
“Now you’re making me feel guilty,” she said.
Charlie turned and looked at her. “Let me just get your room cleaned up, so we can start forgetting this ever happened.”
He stood up, and then she said, “No—I want you to finish your show. You’ve come this far—just go on. Look, you’ve even made a few tips. I bet if you ask your audience nicely, you can get a private show.” She was still smirking, as if she was trying not to laugh. And she probably was trying not to laugh. Since she came in, Charlie had only made about fifteen bucks in tips. She was used to making hundreds of dollars in minutes, with tons of private show requests sprinkled in.
“I really think I’m done,” said Charlie.
“Nonsense. Stay up on my bed.” She peeked over at the screen. “Look—you do have a private show request! How much do you charge for a private show?”
“Usually just fifty dollars,” he said, feeling more awkward than ever. At least in a private show, only one person would be watching his humiliation—unless you count Susie.
Susie didn’t wait for Charlie’s reply. She went ahead and accepted the stranger’s request for a private show. She got Charlie into a private chat room and then she took Charlie’s keyboard and typed, “What kind of show are you looking for, sweetie?”
It was only five seconds later when the man replied. “I want to watch her stroke her shaft until she comes on herself.”
Susie turned and looked at Charlie with a big grin. “So they know you’re a boy?” she said.
Charlie nodded his head slowly, feeling more tiny and pathetic than ever.
“Well? Go ahead. Give the man what he wants,” she said, stepping back from the computer.
And then another message popped up. “Wait! Is that the real MissyBunny69?” said the customer.
Susie smiled and went back in front of the camera. “It’s me!” she said, waiving at Charlie’s webcam.
“I’m a big fan,” the customer wrote. “I watch your show every day. Well—I watch it most days. Sometimes I watch this show. I didn’t know you two were friends. Do you do lots of shows together?”
Susie looked back at Charlie. “Do we do lots of shows together?” she said, repeating the question as if Charlie couldn’t see it on the screen. “No, this is our first.”
Then the customer typed out a new message. “Can I change my request? Can you suck her off until she comes in your mouth? And then I want to see you swallowing it on camera.” And then Susie looked back at Charlie again. She had a big smile on her face, as if she was still trying her hardest not to laugh. “Well? Can I suck you off?”
Big Hard Girls Page 54