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Behind the Webcam (Xanatos & KnightCreep)

Xanatos

Xanatos

Lady in the Making
Joined
Jun 1, 2009
Location
Gender Limbo
Karen Harper had come along way in a few short years. Not only could she barely recognize her old self visually, but even mentally. From being shy and anti-social to being the outgoing and overtly confident woman she was today. She had misgivings about her webcam activities at first, but she needed a way to pay for college, and as long as you're pretty and entertaining, perverts will pay almost any amount to see you. In a few short weeks she had discovered that not only was it lucrative, but she loved it. Months later, she had a cult following online and she loved it. Her erotic comics, drawn and written by herself, were notably less popular than her show, but she drew them anyway. More for fun than money.

That evening, she stood in the bathroom of her hotel room. A large adult convention was scheduled and she was invited to sell her comics and meet fans and such. She was a little nervous about it, but only just. She finished blow drying her hair, and began applying makeup. She'd always preferred a more gothic look to match her black hair. Thick dark eyeliner and mascara, made her blue eyes pop. She dawned a pair of lace panties and matching bra before walking back out into the main room. She sat in silence for a few minutes, while thinking about how to spend her evening. Then an idea clicked in her head. Good timing too, she was too excited to sleep, and too aroused to relax. Opening her laptop she sent an email to her subscribers.

"Hey all! Kari here! Gonna do a live stream to celebrate Eroticon starting tomorrow! Join me in a half hour! Cheers loves!" She sent it off before setting up the camera and double checking the lighting in the room. Then she got comfy, just waiting for her viewers to start populating the live chat.
 
One of the first users to enter the chat was someone with the username "Sampea". "Hey, Kari! I'm a huge fan of yours. I'll be at Eroticon tomorrow. I can't wait to meet you or at least see you in person!."

Meanwhile, in a hotel room only two floors below Karen, a man named Sam Peterson was waiting for the show to start. He had begun to question himself when he first saw how confident Karen was about being transgender. He began noticing that he wanted to wear women's clothing more and more.
 
Kari smiled brightly as she saw the first fans begin to show up in the chat. She recognized a few of them, but there were a few new usernames. Among the normal greetings, she saw one fan's offering of adoration. "Sam-pe-a..." She said outloud, sounding it out. "Am I saying that correctly?" She giggled softly before waving at the camera. "I can't wait to meet you either! It'll be fun." She queued up some heavy ambient music, but turned it down to not drown out her voice.

Almost without thinking, she began stroking herself through her panties. "Anything you loves want to see tonight? Sort of popped on without a plan." She giggled a little. She didn't undo her bra or push away her panties just yet, enjoying building it up.
 
"That's right, Kari! And I would love to see you use your toy collection," Sam typed and sent. Many of the other viewers wanted the same thing.

Sam began rubbing his crotch through his pajamas pants. He then made up his mind about meeting Kari. He would ask her about how she is confident about being transgender.
 
Kari looked at the chat again, a smirk coming over her features. Her breathing was becoming slightly heavier as she continued stroking herself. "Good thing I remembered to pack some I guess." She giggled before turning away from the camera and crawling back to her bag. She unzipped it, fishing through her things. She returned with a vibrator from her bag, plopping back down in front of the camera again.

She leaned forward to make unclasping her bra easier, letting out a sigh of relief as her breasts were finally free. She tossed the bra aside before smiling at the camera again. "So, toys then?" She pushed her panties away, revealing her erection in full force, having lost some of its size from years of hormone therapy. She turned on the vibrator, smiling as it hummed to life. She gently began circling her nipples with it as her hand coiled around her member, stroking it slowly. She let out a gentle moan, closing her eyes as she enjoyed the sensations.
 
Sam grinned and stroked his shaft. He wasn't just looking at Kari's face and nipples. He was also looking at her erection.

The chat exploded with "So hot!", "Put it in your ass!", and "Keep that up!"
 
Kari smirked at the comments that began to fill the chat. "Straight to business, huh?" She moved back on the mattress a little to make it easier to prop up her legs and spread them so the viewers could see. She took the vibrator, turning it off before placing it between her legs. She took a deep breath before slowly pushing it inside of her ass. A more powerful moan escaped her lips as it sank inside.

She slowly began to pump the vibrator in and out, getting used to it again before turning it back on. She let out another cry as it began to vibrate inside of her. She leaned back, making it easier to move the vibrator. Her free hand gripped the sheets as her breasts heaved with her panting and moans.
 
The chat exploded with naughty comments. Sam kept pleasuring himself. He was imagining that he was in Kari's place, and it made him so horny!
 
Kari continued sliding the vibrator in and out moving faster and faster. Her shaft twitched and pulsed with need as she drew closer and closer to her orgasm. "Are you guys ready... I'm gonna cum..." She let out a loud cry of pleasure as she came hands-free. Thick ropes of her seed shot out landing on her thighs and breasts.

She rode out the last of her orgasm, her body quaking as she slumped back against the mattress. She closed her eyes for a moment, panting heavily, waiting for the room to stop spinning. She sat up slowly, smiling lazily as she looked back at the camera. "Hope it was fun for you guys too!" She slowly pulled the vibrator out from inside herself, gasping softly as it came free. She clicked off the vibrator before looking down at the mess she made. "Oh man... I just took a shower too..." She slid her finger over some of the cum on her leg, bringing it up to her lips. She licked her finger before grinning at the camera. "I guess, I'll see some of you tomorrow! Thanks for joining me tonight!"
 
Sam sighed, sad that it was over. However, he had an orgasm, so he couldn't really complain. He gave Kari a goodbye message in the chat before logging off.
 
Kari said her goodbyes, blowing a kiss to the camera before shutting it down. She sighed deeply as she looked down at herself. "Time for another shower, I guess." She got up from the bed, setting about cleaning herself off and getting ready for bed.

The next day, she had been let in to Eroticon early to get her booth set up. She had her various adult comics on display, and had a marker on hand to sign anything. She was aware most visitors would be coming to see her in relation to her cam show, but she didn't mind too much. She was set up next to another woman who sold toys and the like. The two had become fast friends, and spent most of the morning joking and laughing together. Before long the convention opened its doors and swarms of people entered. She took a deep breath before trying to relax into her seat, smiling softly and waving to people as the passed her by.
 
Sam walked up to Kari and smiled warmly. "Hello, Kari. I'm Sam, or Sampea. You probably don't remember, but I was watching your show last night." He had a small stack of Kari's adult comics in his hands.
 
Kari was in the middle of visiting with the woman next to her to notice Sam approach. She heard his voice and looked up a little startled. "Oh yeah! I remember seeing your username in the chat. I'm glad you could make it!" She looked down at the stack of comics in his hands. Her face immediately lit up. "I didn't know you read my comics! That's so cool!" She looked up at him again, smiling brightly. "Would you like me to sign them for you?" She asked, reaching for her pen.
 
"Yes please, and I would love to buy the ones I don't have," Sam smiled. He pulled out his wallet, ready to buy the comics. "May I ask you something?"
 
She smiled widely, when he asked to buy her other comics. "If I have them here, than you bet!" She looked through his stack, pulling the others from a box beneath her table. At his question, she looked up again. "Hmm? Of course, hon. What's on your mind?" She asked cheerfully, starting to sign each of the comics inside cover, so as to not mark the outside.
 
"I... Well... How are you so confident in yourself and who you are? I... I want to have that kind if confidence... And possibly do what you do..." Sam was blushing.
 
Kari's smile fell away some as he spoke. "Oh. Well... That's um..." She bit her lip for a moment as she tried to find a way to explain it. "That's an intense question. It took a long time to get here. I mean, obviously, I was born male. It made life pretty miserable for me. When I came out to my family, they kicked me out. I wound up staying with a friend. The confidence came with practice and experience. When I started the medication and started presenting, I felt better, but not great. When they started working though... Well, you can see for yourself. Honestly, I started the cam show because I was desperate for money. I didn't realize how much fun it would be."

She leaned forward on the table, motioning for him to get closer. "Now, when you say you want my confidence and to do what I do, are you talking about a cam show? Or is there a girl hiding in there that you haven't let out yet?" She asked in a hushed whisper to not draw attention.
 
"There's a girl in me," Sam said in a hushed whisper. "I was hoping that you could help me get her out. I want to be her and maybe, if you're willing, I could do cam shows with you... It would be a dream come true."
 
Kari blinked a few times before her lips spread into a smile. "Oh, honey." She got up from the chair and walked around to Sam. She wrapped her arms around him, no... her, in a tight embrace. As she pulled away she smiled. "I'm so flattered that you want me to help you. You are a girl, sweet heart. We just have to help the outside match the inside. It would be my dream come true too."

She smiled then, looking Sam over. "Fortunately it won't take too much work to help you like your reflection at least. Getting to where I am though... I've been on medication for a couple years, honey." She grabbed a pen and began making a list. "You should be able to buy most of these things here at the con. If you tell them that Karen Harper sent you, you might even get a discount." As she finished the list she handed it over to Sam.

The list was simple, but certainly had things on it that would be embarrassing to buy for sure. It listed breast forms, lingerie, clothing, a wig (unless Sam's hair was longer anyway) and the necessary makeup. At the bottom of the list was her hotel and room number.

"After the con settles down for today, how about you come up to my room and I'll help you get started, hmm? It'll be fun."
 
(It's a good length. He could pass without a wig.)
"Thank you, Karen," Sam smiled. "I'll be there. What time?" He looked at the list and read over it, his cheeks turning red. However, he steeled his courage and smiled wider.
 
Kari hugged Sam once again. "Oh, it's going to be so much fun. Come buy around eight, okay? That'll give me time to clean up and make myself presentable." She returned Sam's comics with a smile. "All signed and ready to go." She refused the payment for the comics Sam was missing, happy to provide them as a gift of congratulations. She was absolutely smitten by the fact that she would be the first person that Sam came out to. She turned her new friend around pushing them on gently. "Go on now. You've got shopping to do. I'll see you tonight."
 
"Thank you so much. I'll be sure to wear some of my favorite new clothes and lingerie for you." He walked off, ready to shop.
 
The day felt especially long. As fun as it was for Kari to meet other fans, and sign comics, she was excited about helping Sam start her transition. That night she had showered and cleaned the hotel room. She wore her lingerie and her bathrobe, neatly wrapped around herself. She waited for Sam to arrive, excited about the evening's events. She looked forward to each step they would be taking and couldn't wait to assist her. It felt empowering like she was getting to help others the way some people had helped her.
 
Sam knocked on the door. She was wearing a pink miniskirt, a pink tube top, a pair of pantyhose, a pink pair of high heels, and a sheer pink set of lingerie under the outfit. She was grinning from ear to ear.
 
Kari wasn't sure what to expect when she opened the door. Perhaps that Sam would have taken care of her shopping and shown up with everything in bags. She certainly wasn't expecting what she was greeted by when she opened the door. Her lips spread in a wide grin when she saw Sam on the other side. She quickly hugged her, taking her hand and guiding her into the room. "So, how did everything go? How was getting ready? Did you have fun?" She asked, smiling widely.

"Did you make sure to shave everywhere really good? How about the breast forms? Were you able to put them on alright?" She asked her questions a mile per minute but she was simply so excited.
 
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