Sammi Meets Teddy

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted the same way it had been going, relatively well for Sam. And now that he knew where he was going to school, it became hard for him to hold back all of his excitement and girlish glee.

His parents, still somehow oblivious to their new daughters existence, were very happy for him. They had always worried he'd never find his footing and would end up in a dead beat life after high school, so to find out he was going to a nice school a state over really made them happy. And as his graduation rolled around the decided to throw a party for him and invite all of his family. Sam had no problem with this, and liked most of his family, but he was a little disappointed as there would be several people staying in their house which would make it hard to be Sammi.

But he wasn't about to tell his parents this, so he just ran with it. Only a few days before the party and his graduation and the plans were settled and things were beginning to happen. Sams parents told him that there would be two people staying at their house: His Grandmother, who would be coming the day of his graduation and party, and his uncle who would be there three days before. Sam knew his Uncle Teddy pretty well, they had seen each other at many family events. Sam didn't mind his Uncle Teddy, but he certainly wasn't his favorite relative.

Teddy was a larger guy, about six feet two inches and rather muscular. He had slightly more tanned skin and short black hair. He liked football, going to bars, and giving women a hard time (All in the name of fun, of course.) All of which Sam was very much the opposite of, making it hard for them to connect. Teddy had no wife, but he had gone through several girlfriends over Sam's life, most of which were the sort of ditsy girls that it was obvious they were both in it just for the sex and not much else.

Sam was even less happy to find out that Teddy would be sleeping in "The guest room" which was really his sisters room, cutting off Sammis access to his sisters stuff. But again, Sam wasn't about to protest. Instead Sam just tried to prepare the day before Teddy got there. He grabbed whatever he thought he might need from his sisters room and moved it to his. He didn't have much space or any more boxes to hide it in, so he just made a pile in his closet next to his box and covered it in a blanket. Sam doubted anyone would go looking in his closet in the first place so he figured it was well enough hidden.

Then, as he would be sharing his bathroom with his uncle, he cleaned and hid all of the girly makeup and cosmetics that he had in there and put them in his sock drawer. He also grabbed a hand mirror too just to make sure he could apply the makeup in his room. And lastly he hid whatever recording things he had also, and decided only to bring them out when in use as to not give anything away. He decided that this was good enough, and that he was in the clear.

The day that Teddy got there went as one could expect, he arrived at around 4 in the afternoon and Sam's family decided to go get dinner. Sam and Teddy tried to make small talk about his graduation and his future but it was obvious to both of them that neither cared all too much. After dinner they went back home and Teddy moved his stuff into the guest room. Sam's parents and Teddy then spent the rest of the night downstairs drinking wine while Sam stayed in his room on his phone.

The next day was Friday, Sam's last day of school, while his graduation was on Sunday. He dealt with all the goodbye bullshit at school, signing yearbooks and such, wishing each other luck in college. The day was a minimum day as it ended at one, so Sam got out and raced him with excitement. Once he got there he went to check out his stuff in his closet, to mysteriously find that the blanket was gone from the pile of stuff.

Sam just pushed it out of his mind and went about the rest of his day. Things happened slowly as he wasted time while his parents and Teddy were out getting things for the party. Sammi told her followers that he would be doing a show tonight decently late, and apologized for the lack of shows due to family matters. The rest of the day came to close and the family began to go to sleep. At midnight or so, Sammi began to get ready. By one she was fully dressed and on show.

Some time in, Sammi decided to run to the bathroom and paused her show. She got up and only then realized that she had left her door open slightly, a bad habit while trying to stay undiscovered. She went into the hall and into the bathroom, did her business and went back. She went back into her room to see Teddy sitting on her bed, waiting for her.

"So you're a faggot now, then eh?" He said matter-of-factly, "Dressing up like a little naughty girl and recording yourself doing naughty things. I guess I could always tell you weren't very manly but I would've never guessed you bend like this until I found your stash in the closet."

Sammi just stood there in shock, mouth slightly agape.

"I needed an extra blanket, and when I couldn't find one your parents said you might've had it. Indeed you did, along with many other things." He went on, a wicked smile on his face. "But don't worry, your secrets safe with me. Come sit next to me." He ordered. Sammi Obeyed, not wanting to test the man. Once sat, he leaned over and whispered into her ear, "I won't tell as long as you agree to be MY slut whenever I'm around. What do you say?"

After a moment of thought, Sammi didn't want to do anything with Teddy, but figured she had to at this point. She nodded slowly in agreement, and let out a weak, "Yes."

"Great. But first, it's 'Yes, Sir.' From now on. Understood?" He breathed harshly.

"Yes, s-sir." Sammi said with terror in her eyes. She had seen this scenario far too many times online. Far too many sissy stories started like this, and she knew where they lead. She couldn't tell if she was excited or horrified. If you judged by her sissy clitty that was beginning to leak pre cum and fight the cage confiding it, you could assume she was turned on by the thought.

"For right now, go turn on that camera of yours. It's late and I'm tired so we'll keep it brief, but tomorrow we'll have so much fun!" He said with a grin. So Sammi went on and restarted her stream. The comments started to flood in asking who the man was, but she kept silent. Teddy obviously didn't know he was on stream and so she figured to keep it that way.

"Get on all fours on the bed, slut!" He barked. Once she did as told she faced him, with him now standing. He unzipped his pants and revealed his monster of a cock. It was about 9" and girthier than anything she had played with. He lightly grabbed her soft chin and tilted her head up so that he could rest the snake on her. He laughed at the sight of his sissy nephew dressed like a slut, with a cock on his face.

He then grabbed his hairy balls and put them on her mouth and ordered that she start servicing them. She did as told and began to massage the man's balls with her mouth. The musky stench began to overwhelm her and she shook a little, all the way down to her bones. A minute or two in and she felt his hand grab one of her ass cheeks and spread it. He laughed as he saw that she was both plugged and caged.

"A real bitch, aren't you? At least you know that, and locked away that pathetic dick of yours! You'll never be using that thing, I can tell you're a dirty girl who loves it up the butt, isn't that right?" He hissed at her. She moaned a response to him from under his balls and he loved the feeling. He began to lay some firm slaps on her round butt, light red marks beginning to take shape. With every blow she braced and closed her eyes, releasing a little yelp from beneath the man's rod.

But once the slapping stopped, she opened her eyes to see that he moved his dick off of her face. Her eyes met his, and for a moment she felt something. Not joy, nor hate. She hadn't felt this yet before in her life. It was a weird feeling, one that came from the depths of her soul, but at the same time seemed to radiate from his caged dick and sissy hole. It was a feeling of submission. True love for being used like a true sissy bitch overtook her for a moment and she gave him puppy dog eyes, yearning for more.

He picked up on that, and was seemingly empowered by it. He was a rough man, that's a fact. But for a moment he was gentle, as he lightly grabbed her chin again and leaned down to plant a kiss in her mouth. He probed her mouth with his tongue, and invaded every inch in a ravenous rampage to claim what was his. She was completely shocked by this, but the feeling she had felt grew larger. She was ashamed but she began to reciprocate the affection, and she moaned into his mouth with true bliss. She felt hungry, hungry for something. Hungry for dick.

And as if he knew that, he back off, leaving her mouth open and empty, longing for something to fill it. And he lined up his massive cock on her lips. Without resistance, she licked the head of it, and as if it were the red light turning green he was off to the races. He rammed his cock into her throat, she felt it slam into the back of her mouth and begin to push into her throat. She was good with her toys, but they were far less girthy and even still a challenge to get al eight inches down. But Teddy's dick was a new beast all together.

He pressed, getting about seven inches deep, her throat screaming in pain and her eyes beginning to well up in tears. He held it there for a moment, then pulled it back to the head. She took some breaths rapidly, but soon he began to ram back in. Teddy's rod of meat rested on her tongue as it came in and out, and she tried to keep her breath. She licked it when she had the chance, and tasted the precum.

She loved the throbbing member in her mouth. Every inch in her made her feel more complete. And with every thrust he seemed to get a little deeper. Eventually though, he bottomed out. She was surprised when she felt the hair of his crotch press against her face, and she could taste the musk that she had smelled earlier. She felt her own saliva on his balls pressed against her face. He held her there for a moment or two, and as she was running out of here he pulled completely out. She gasped for breath, but through a smile she heaved.

Her makeup was ruined, and her throat was soar, but she knew that the ride wasn't over. And to his surprised, she grabbed his dick and began to work it with both hands as she put the tip between her lips. She was trying to milk him for his sweet cum. He loved it. He loved it so much, as he'd never seen a woman before so hypnotized by his cock, so hungry for cum. So with every bit of strength he had he pulled back out and prepared. She opened her mouth wide, knowing what was coming.

He thrust with his whole force into her mouth, reaching the depths of her neck in no time, and his balls slapped her chin. And he let out heavy moans as he began to spray his cum down her throat. She let out moans on his dick at the feeling of her stomach being filled. She was running out of breath as he was unloading his cum down her throat, but she could have held it the whole. But she chose not to, she pulled off his dick and held it to her face. She let him cover her face with his cum.

Once they were both done, she turned to the camera and give it her trademark kiss and smile. Then she crawled over to it to turn it off, as he grabbed her ass and delivered on final smack to it. She looked back at him and smiled, cum still staining her face. He grinned back, a toothy grin with zero energy left. That night they both went to sleep happy, especially knowing that it wasn't over.

The next day Sam's parents left to get final preparations for the party. They would be gone for several hours, and invited Teddy but he decided to stay back. Once they left Teddy went up to his room, and Sam went up to his. Sammi began to get dressed when Teddy peaked his head into the room and spoke, "We're going to get this on recording too, slut. And I don't want to hear any arguing. Finish getting ready, get your stuff and set it up in your parents room by the bed. I'm going to ruin your faggot ass on your own parents bed!" And with that he pulled his head back out and closed the door.

This scared Sammi, as she didn't want to risk leaving any evidence in her parents room, but she also didn't want to try to argue it. So she did as told and finished getting ready. She grabbed her things and set it up on her parents bed, a comfy well made king sized bed. She checked out her show page and found out that she had earned more money last night than any night before. She read some of the comments, all saying how they wanted more of her getting dominated by real men. And sadly, she couldn't agree more.

So she laid down on her parents bed and waited. A few minutes later Teddy came in with a box of condoms, a tube of lube, and a pen. He put them down on the night stand beside the bed and ordered her to start recording. She started the show and then moved to do the same thing as last night, but this time he grabbed her. He moved her to point her ass to the camera, and pulled down her slutty skirt and stockings. Her bare ass now pointed to the camera, and he grabbed the pen. He wrote, "Sam is a faggot." On one cheek and, "Worthless cock slut." On the other.

Then he went back and started to do as they had last night. Started with her licking his balls as he rested his dick on her face. Then he moved her off all fours and sat her in front of the camera. He sat next to her and began to make out. They made out as violently as they had last night as his hands explored her body. He found his hand between her thighs and grabbed her caged dick. He stopped making out for a second and told her to spread her legs. She did as told and he grabbed the pen once more.

On one inner thigh he wrote, "Worthless faggot cock." With an arrow pointing to it and, "Not a man." On the other thigh. Then he pushed her on her back and held her legs up. He reached over for the lube and took her Sammi's plug. He rubbed some lube onto the perfect little sissy hole and began to finger fuck her. She moaned slightly, but was obviously eager for more. He fingered her for several minutes then grabbed both legs and put them on his shoulders.

He put on a condom and positioned his beast of a cock in front of her sissy hole. She breathed in and closed her eyes in anticipation. He then spoke to the camera, "This is my bitch. And I claim her asshole as mine!" Then rammed his cock in. She let out a scream as the walls of her ass were spread. She was split on Teddy's massive cock. He kept pressing in, moaning at the feeling. He practically growled, "This bitch is tight! My god!" And pulled back a bit only to then ram back in.

He started to pump at a rhythm, getting slightly deeper into her ass with every thrust. She could hardly breath, moaning in between every breath. Her moans filled the room alongside his grunting noises, it was almost like a symphony of sex. He was beginning to sweat and turn red as he picked up pace, his hands gripping her legs began to squeeze leaving red marks on her thighs. She grabbed the sheets and tried to quiet her screams but it was impossible.

They fucked like this for a while, fifteen minutes or so. They had sunk into a rhythm and Teddy could get maybe seven and a half inches into Sammi. Then Teddy pulled out completely and picked Sammi up off the couch. She was part brain dead at this point, in coherent as her moans silenced to a low pleasurable purring. And he began to make out with her again. He cupped her ass in his hand and violently molested it. But she didn't mind at all, she was lost in the feeling.

He then grabs her with both hands and stands up while carrying her. She knew he was strong but how effortlessly he had picked her up seemed shocking. As if they were connected she somehow knew what he had planned and wrapped her legs around his waist and back. She then wrapped her hands around his neck and looked at the camera as he lined her up. She gave her trademark kiss and smile as he then dropped her onto his dick, letting gravity pull her all the way down.

Her whole weight, all 124 pounds of it came down on his shaft. She screamed as she felt his dick reach new depths in her asshole until he bottomed out. He grabbed her head and silenced her screams by invading her mouth again. Then he began to lift her up slightly and drop her down again, fucking her while standing. She felt completely helpless, but not in a bad way. She was completely and one hundred percent at Teddy's mercy and it was beautiful. That feeling she had felt last night came back to her like a tidal wave, washing her in this feeling of complete submission.

They fucked like this for another ten minutes, but Teddy couldn't keep this up forever so he eventually pulled his mouth off of hers. He then began to pick up his pace with every ounce of energy he had left. She felt like she was on a roller coaster, being pulled up and down by a force she had no control of. And just like a roller coaster, they came to the big drop and they both let out huge moans as he began to come. At first she disappointed, knowing he had put on a condom and she wouldn't get the feeling of his seed inside him, but then the warm liquid filled her insides anyway.

The condom must have broke somewhere in that violent fucking. He knew this too and looked at her with a look that said, "I'm sorry but I can't stop." And she responded with a smile and kissed him on the cheek. He smiled back and rode the wave as he filled her asshole with his come. After a minute of standing there they were both content, there was come dripping out of her asshole and his dick began to lose size in her sissy hole.

He then fully lifted her off of his dick again and lowered her back onto the bed. At this point they were both wildly out of breath and covered in sweat. Her makeup was running madly and making her face look like rivers of color streaming down. Her red fuck-me lipstick had smeared. He took a minute to regain his breath as she took a minute to come back to reality. She felt more than full, she felt stuffed like she had just eaten thanksgiving dinner.

Once the world stopped spinning for them, he picked her up and pointed her ass in the direction of the camera again. He put his cum covered dick back in her mouth, which she accepted without a doubt, and spread her ass cheeks. She gave her show a full view of her cum oozing sissy hole. The writing on her butt and thighs had smeared wildly, and some had been slightly covered in cum. But none of that mattered, as it had been one hell of a show.

After it was done, his dick was thoroughly cleaned off in her mouth, she pulled it out with a *pop* and turned to face the camera one more time. She grabbed her plug and plugged the last of the cum back in her asshole, then gave a weak and tired kiss and smile to the show. Then she turned it off and lay down on the bed. Teddy pulled up his boxers and laid next to her, and they cuddled. They didn't talk for a few minutes, maybe it was weird for them.

But Teddy broke the silence with an honest question, "How long have you been a slut?"

"I guess a few years now." She replied.

"Hm. Have you been fucked before?"

"No."

"Well you were great. And I have to admit, you're one smoking hot faggot!"

"Well I'm not just any faggot. Now I'm your faggot."

"Yeah you are. Whenever I see you, this'll be a regular thing."