Brianna Finds a Father Figure

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Brianna is caught crossdressing and finds a new daddy.
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Brian was an eighteen year old nobody with short blonde hair, pale white skin, and soft blue eyes. He stood at five feet eight inches and lived with his mother. He liked his old school, but when his mother got a transfer he was forced away from his home town. They moved into a small town in Colorado, into a small two bedroom home in a nice suburb. Brian was new to the town, now had no friends, and was going into his senior year of high school at a new school. But he managed to keep his attitude positive.

That because he didn't care for any of those things very much. He had a lot of online friends, and he only cared about his future and going to college. His mother worked for most of the day, most days and left him alone quite often in their home. Brian, being young and horny had gotten into porn quite a while ago, though a more recent endeavor was his dive into sissy porn and cross dressing. His freshman year is when he ran across it, and by the middle of sophomore year he had tried on his first pair of panties out of his mother's drawers.

In a way, the move almost helped him. Giving him more time to dress up, less people to possibly be exposed to, and no expectations of him. Ever since he started dressing like a girl, he steadily improved at transforming into one. He got better at choosing clothes, doing his makeup, speaking like a girl, and acting like one. His persona was Brianna, the slutty sissy girl that made friends online and occasionally sent photos of herself. She had no problem with this, and neither did all the boys she had met who received those photos.

Brianna had never done anything with anyone in real life, but as a sissy usual does she practiced with toys. She managed to buy a six inch dildo and a chastity cage for her three inch cock from a sex shop near her old house. Her mother was none the wiser, and that's the way Brianna wanted to keep it. She also kept herself well shaven and moisturized, her skin would be indecipherable from that of a real girls. She even found a blonde wig in her mothers closet, the color was slightly off of her own hair but the wig was large enough to hide her real hair.

Once fully moved in and settled, Brian and his mother began to sink back into their routines. Brian's mother leaving the house at eight in the morning and coming back by seven. Brian going to school from eight to four, coming home, and playing dress up until his mothers return. The two would then eat, and the rest of the night would continue with no suspicion to be had. Brian's mother was hardly a bad one, just being a single parent meant she couldn't spend as much time with her son as she'd like. And Brian would never blame her for anything, his father had left them when he was young and his mother was his only family.

And so things went on as normal as ever until one fateful day, when Brianna decided to go into their back yard. She got all dressed up, in a nice flowing dress and had her makeup light and inconspicuous. She went out back to frolic in the yard and enjoy the fresh air, thinking she wouldn't have to worry about being spotted due to the large fence surrounding her yard. And she would have been right to assume that, except for the hole about the size of one's out stretched hand on one of the fences.

She frolicked, relaxed, and did some semi-real yoga in her back yard making no effort to be quiet. She wasn't loud, but she made enough noise for her neighbor to wonder why his new neighbor was out back and what she was doing. Rick looked through the hole in the fence, expecting to see the woman who had just moved in next door, the one with only a single son. And instead, he saw a young girl enjoying her youth in the yard. He didn't know what to think, as he was fairly sure his new neighbor had no daughter.

A few days passed, and on the following Saturday, one of the only days Brian's mom had off work, Brian and his mother were sitting down for breakfast when a knock came to the door. Brian's mother answered the door, and it was her neighbor, Rick. They made small talk, but Rick had come to give her some mail that was put in the wrong box. Brian overheard their conversation, and some hairs stood on his neck when he heard Rick mention a daughter. Brian's mother reassured him she had no daughter, only a son, and instead of prying Rick just smiled and accepted it. This made Brian a little worried, but as Rick hadn't stuck around to push the point he assumed he had nothing to worry about.

Two days later, and Brian was once again fully dressed and running about the house. Another knock came to the door, but as usual Brianna didn't answer the door as she was dressed up. But she did see as a note was pushed through under the door. She got up from the couch and slowly approached the note, tiptoeing so whoever was outside couldn't hear her. She picked up the note and saw the message written on it, "I know your secret. Let me in, or I'll have to tell your mother."

As though He knew she had read it, another knock beat through the door. Brianna was stunned, and stood there not knowing what to do. But she thought about the threat on the note, and decided to open the door. Rick stood there with a that same devilish grin. He walked in and closed the door behind him, Brianna taking a step back. He looked her up and down and said, "Dang. Brian, right? Well, I assume not, that's not a girls name. What's YOUR name?"

And after a few seconds of hesitation, Brianna practically whispered, "Brianna."

"Hehehe." He bellowed, "So what, then? You're some kind of faggot Brianna? You like to dress up like a girl and go around strutting your stuff?" To which Brianna did not respond. She only looked to her feet with a shameful look on her face. Rick then began to walk to a chair, and lightly grabbing Brianna's shoulder said, "Take a seat, Brianna. We should talk." And Brianna sat back down on the couch.

After they had both settled, Rick looked Brianna in the eyes and asked, "So, do you like men? Do you want to be a real girl?"

"I. I guess. To wanting to be a real girl, that is. I almost feel as though I wasn't supposed to be a boy. I just feel right while dressed up." Was Brianna's response.

"Well, Brianna, I understand you never really had a father?"

"Yeah. He left before I can remember. Mom never found someone to replace him, so I've never had one."

"Sounds like you need a father figure. I mean, look at yourself. Dressed up like a slut and hidding in the closet."

"What are you sayi-" Brianna started but was quickly interrupted.

"Brianna, now is my time to talk. You'll talk when I say you can. I know your secret, and I can see you don't want your mother to know. So here's my one and only offer, take it or leave it. I'll be your dad, you'll be my little girl. You do as I say, when I say it, and you'll like it. If not, your mother finds out that you're a faggot. Decide quickly."

And to this, Brianna said nothing. She only hung her head once more, her hands held in her lap. Rick laughed once more and said, "I'll take that as a yes. Now, Brianna, get up and come over here." Doing as she was told, though having no pride in it, Brianna got up and walked over to Rick sitting in his chair. He then reached behind and grabbed her butt, not too hard but firmly. This caused her to jump a bit, and as she did he spread his legs and moved her in between them.

Rick then ordered her to get on her knees as he unbuckled his pants. She hesitated, and before she could reconsider, Rick pulled her down with great force. She nearly fell onto her knees, and she winced in the pain. She looked up to his face, to see the face of the devil looking back at her. But soon, she lost sight of his face and instead she saw the great mass that was Rick's penis. It was huge, nine inches and girthier than anything Brianna could've ever imagined. She gawked at it, her eyes going wide and her jaw hanging open.

Rick, always being the type to take his chances, took her open mouth as an invitation to stuff the head of his cock. She was surprised to find the throbbing member invading her mouth and sliding down her tongue. The salty, musky taste hit her and she winced once more. Rick was trying to push to find the limits, so he kept pressing on, digging deeper down her mouth. She tried to pull back off of it, but his hand found itself on her head and holding her still. His other hand exploring her body.

He eventually pulled up her dress and saw a caged clitty under her panties. He reached down and grabbed it, which gained a little jump out of his daughter. He laughed and mocked her, "Look at this pathetic thing. You were meant to be a girl, that's for sure. You could never please women with this, you were only ever meant to please men. And with some time, that's exactly what you'll be doing." She tried to keep her mind off what he was saying, but he eventually started hitting her breaking point as he pushed too deep, causing her to choke and gag.

Brianna, in her fit of coughing and gagging, tried to fight the hand holding her down the warm shaft but couldn't find the strength to beat her new master. She had only gotten about six inches down by the time she started to gag, and after holding her there for maybe thirty seconds Rick decided to release her. She pulled off and caught her breath, saliva covering her mouth and her lipstick smeared. With tears beginning to well, and pain in her eyes she looked back up to Rick. Rick returned a gaze that could only be described as loving punishment, the kind of look a father would give as he watches his kid learn a lesson the hard way.

But her moment of freedom didn't last, and soon his hand forced her head back onto his cock. He once again pushed her down as far as she could go, held her, then released her. He began to quicken his pace, forcing and releasing with less time for her to breath. Soon, she learned to start breathing through her nose, as he stopped fully releasing her, and merely used her head to bob up and down on his length. He worked her good, her makeup completely trashed and saliva getting everywhere. She had drooled onto her dress, and her eyes were tiring.

They sat there, Rick using Brianna's head for fun for forty minutes. This was where Brianna learned the first thing about her new daddy, he could last a while. But all good things come to an end, and eventually Rick began to moan loudly. He used both hands to grab Brianna's head and used more force as he rammed in and out of her head. She begun to get seven inches down, pressing and on the brink of going down her neck. But he knew that she wasn't ready to swallow his lead, yet, so he pulled out the last second.

He shot a massive load, at least three times larger than any that Brian had ever produced, all over her face and chest. She was completely caught off guard by it, and the smell was overpowering her. The musk of Rick's come was too much for her to handle, she reached up and plugged her nose. But Rick grabbed her hand and removed it, he wanted her used to the smell, and he then scooped a little up with his finger and forced it into her mouth. The taste made her gag a bit, but she dutifully licked it off his finger and was about to swallow.

"Swirl it around in your mouth, whore. You're going to need to get used to that taste so I don't want you downing it and forgetting." Rick ordered. To which, she sadly obeyed. She swirled it around on her tongue, the taste slowly taking over every inch of her mouth. She began to get used to it, she tasted the saltiness and hearkened back to some fond memory that she couldn't fully grasp. But she then swallowed it, and looked back up to her daddy.

He had leaned back in his chair, but ordered Brianna to lean in a bit, where he then rested his dick on her face. She smelled that smell again, but this time she didn't wince. She only took it in as she stared at the cock on her face, she felt it's warmth. And after a few minutes like that, Rick tucked his cock back into his pants and was redoing his buckle as Brianna stood up.

"How come you never actually answered me. I expect my daughter to answer my questions, so why did you say nothing when I asked if you wanted to be my girl?" Rick posed, shooting a deadly look at her.

"Because you never said I could speak." She responded softly, returning a soft gaze.

His expression changed, changing from questioning force to pride in his work. He stood up and grabbed his daughters ass with both hands and smiled. He said, "Good girl. That'll be what keeps you out of trouble. I'll be back at the same time tomorrow, be ready because we're going to start your training. In the mean time, wash off that come, possibly into that dirty mouth of yours, because next time I'll be coming in you." And with that, he let go of her ass and walked back to the door.

He opened it, turned to look at his come covered daughter, still standing where she had been, and gave her a nod. He left and closed the door with a slam behind him, leaving Brianna to her thoughts. She slowly cleaned up the mess they had made, and walked back up stairs. She looked into the mirror and saw the come covering her. She scooped some onto her finger and into her mouth, tasted her new father, swallowed, and repeated until most of the come was clean off her face. She saw her messy makeup and thought about how she might dress tomorrow.

Then she looked at her dress, the come covering it, and remembered that it was her mothers. So she stripped naked, cleaned her makeup, and took the clothes down to the washing machine. She threw them in and looked at her caged dicklette. She laughed as she thought about it compared to Rick's, and as the thought of Rick's cock came into her mind she saw her dicklette try to get hard. She was almost impressed that she was getting hard off thinking of her daddy's cock, but that's when she accepted what she was: A sissy slut.

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4 Comments
Kerrysub4uKerrysub4ualmost 6 years ago
I Wish

I secretly dressed when I was young. I had fantasies of an older man catching me and turning me into his gurl. Dressing me, using me like a slut. I love the story . I wish it had happened to me. Love to chat about it . I'm kerry8866@hotmail.com

cdCindy1cdCindy1about 6 years ago
loved this story

I too am a sissy CD cocksucker and I loved this story. I wish my neighbour knew my secret and forced me to be his cum slut. I can't wait to read more of your stories.

AnonymousAnonymousover 6 years ago
Brilliant line

"Because you never said I could speak." She responded softly, returning a soft gaze.

Loved that

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