Sammi Starts Camming

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Sam Meets Sammi for the first time.
1.5k words
4.6
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Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips.

He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with his figure could even come off as a girl from behind. His green eyes and small facial features were hardly boyish.

He considered himself straight, but most kids at school chose to think the opposite, often calling him names. The girls even seemed to think it, as by his second year of high school most of his friends were girls. And not in the good way, they all saw him like their gay guy friend, to the point of even treating him as if he were one of the girls.

But sam's thoughts on his sexuality changed one day. He was looking at porn on reddit, the closest he could get to having sex was with his hand, and he happened across a thread for something called "Sissies". Upon further inspection he found out to his shock that it was all guys.

He looked at the photos of these girly boys and thought that he should be absolutely turned off and click away. But he wasn't, and he didn't. He was almost mesmerized, fascinated by how some of these boys were so convincing and hot.

He looked at some comments on the photos and saw that there were around a hundred comments on any given photo, almost all giving gracious support or compliments. Reading some of the more sexual comments made him red and feel overheated.

He pulled down his pants and briefs to release his 4" rock hard prick. He spent the next twenty minutes looking at these photos and comments. And from that day on he was hooked.

He started to look at sissy porn much more often. And eventually it become the soul thing he looked at. He watched sissy hypnosis, sissy captions, sissy stories, sissy anything. For some reason it was all so enticing to him.

After months of this he was fully enthralled in this sissy world, when he saw a new post by someone he hadn't seen before that caught his eye. This "girl" had long brunette hair, and a very short, feminine shape. She wore a skimpy skirt, leggings, and a small white tee.

Sam recognized himself in her. And suddenly, a light went off in his head, and he had a new craving. He wanted to try to be one of them. At least try to be. And as he thought about it he soon realized how he could do it.

Sam lived with his mother and step father. His sister was moved out and in college but a lot of her stuff was still in her room. So he waited until his mother and step father went to sleep and snuck into his sisters room.

He didn't know exactly what he was doing or looking for, but he just grabbed an outfit that resembled that of the girl that inspired him. He grabbed some makeup and anything else he thought he might need. Once he had his hands full with stuff he was about to leave when he spotted a shoe box in the corner of his sisters closet.

He bent down and picked up the shoe box. Opening it he found several toys: a 2" diameter butt plug, a 5" long dildo, and a vibrator. His heart nearly jumped out of his chest as he shut the box quickly. His face was bright red. But despite every sense in him that said to put it back, he threw it on his pile of clothes and went back to his room.

Some time later, he finished his outfit by tying his hair into a pony-tail and standing up. The clothes felt right, the makeup felt right even though he was laughably bad at it, and the butt plug filled him in a way he had never felt before. He looked to his mirror on the closet door and was greeted by someone new. He was greeted by Sammi.

Her heart was racing, her little dick was hard as diamonds pressing at her panties. She curtsied to herself in the mirror and did a little spin. She grabbed her phone and took a photo of herself. She looked at the photo and thought better than to use it. Instead, she went back to the camera, puckered her lips as if to blow a kiss, winked, and then took a photo.

She posted it to the same thread she had been watching for months along with a little comment, "Hi, I'm Sammi. This is my first time posting so go easy on me ;)." Almost immediately she felt some kind of regret sink in. She worried people wouldn't like her, or would insult her. She began to think about deleting it.

But then a comment came through. It read, "Damn girl, where have you been? You're a perfect cutie!" And Sammi didn't know what to think. She read it over several times, but before she thought of anything another comment was posted, "Very sexy. Keep it up."

And so Sammi was born. It became a common thing for her to do. She would wait till late at night, dress up, take photos and post them. She began to get the hang of doing her makeup, and she even started to take her dildo. She was truly loving it.

She got so many loving comments, and quite a few helpful tips too. She shaved her whole body, began to lotion it, do squats every night, and practiced talking girly. All of this made Sammi feel like a real girl just with a little cock. She became a common face and name on the thread, people knew who she was and she loved that.

Then one night, while practicing riding her dildo, she received a comment with a link, "You're a grade A slut, aren't you? You should start camming, I know I would watch." And the link was to a cam site. She checked it out, and found the rules to starting to cam. And a few days later she went to the store and bought a web cam.

Her first cam show went slowly, only a few people watched. But those who did made very sweet comments, and had some fun conversations with Sammi. Soon she began to pick up speed, however. By two weeks she had amassed a bit of a following, and she actually began to get donations and requests. She felt like a professional.

She would do shows where she started in her boy form and showed the whole process of her transforming into Sammi. She did shows where she stuck her dildo to the wall and practiced blowjobs for an hour and a half. And during her shows she would try to do requests from donators, writing things on her butt in sharpie like: "Daddies cum slut," and, "Insert cock," with an arrow pointing to her sissy hole.

She got a lot of donations. Most of the money got saved, then the rest went to buying more sissy clothes and toys. She even opened a P.O. box and put it on her show so people could send her things. Many of her fans sent her things, so many she had to close it or else she would have no where to hide it all.

Her favorite two things she received she unboxed on her show. They were a pink chastity cage and an 8" black, realistic dildo. She immediately put the cage on and snapped it locked. It hurt her sissy cock but it was a good hurt. And she then spent the rest of the breaking in her new dildo.

She started by trying to deep throat it. She had gotten the ability to deep throat her 5" dildo so she could only go about 6" down on the new one. Then she put it down and put it between her ass cheeks. Due to the squats her butt had gotten quite perky and bubbly, a nice size for a sissy. She teased her audience with it for a few minutes, then finally positioned herself for the main course.

She felt the head of the rubber pressing against her sissy hole. She took a deep breath and tried to go all the way down in one go. She impaled herself on it, almost making it down. She probably got 7" down, and it forced out a scream of ecstasy and pain. She held it there for a minute, then began to ride.

She put all of her skills into it. She would go all the way up to the tip, then slam it back down, each time getting closer to the bottom. She worked it for half an hour, sweat and tears ruining her makeup. And finally, she felt it. She felt the fake rubber balls press against her cheeks as she sat her whole weight down on the entire shaft.

She turned to look at the chat of her show, to see that there had been over one hundred dollars in donations, and a record high of viewers. All of which were cheering her on. She had never felt so loved, nor had she ever felt so fulfilled as she did with an 8" black dildo up her sissy ass.

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AnonymousAnonymousabout 4 years ago
More...PLEASE???

OMGosh, please add more chapters about Sammi...and hur continued camming. Luvly💕....arousing start in this Pantyboi's humble opinion.

SissyCrissy6245............xoxoxo

AnonymousAnonymousover 6 years ago
So where does this go?

Great start, well written, leaves the reader wanting more.

AnonymousAnonymousover 6 years ago
Love it

Love it & it's my dream to be like her

AnonymousAnonymousover 6 years ago
Hot story!

Can't wait to hear more

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