tagTransgender & CrossdressersJames' Story Ch. 01

James' Story Ch. 01


James was an average 23 year old loser; short, scrawny and wholly unremarkable. He often found himself scouring all the bars and clubs in the city he lived in looking for even one woman that would give him the time of day. One night, or rather early morning, James had lost all hope and decided to make his way back to his single room apartment. He checked his phone and saw that it was 2:00AM, he cut his losses and began the long walk home.

He was close to halfway home when he was met with the bright lights of 'CANDY', a new club he'd tried earlier in the night and had no success in. Something was different this time, at the front of the door was the most beautiful woman he had ever seen. She had flowing black hair, a tiny waist with huge curvy hips but most importantly the small black skirt she was wearing emphasised the huge ass he carried behind her. It was basically instinct that forced him to follow her into the club and through the sea of people he hadn't noticed only to be staring at the back of this woman's head as she took a seat at the bar.

"Is there anything I can do for you, hun?" She asked, turning her head slightly.

"Umm, s...sorry. I didn't mean to bother you" He spluttered out in panic.

"I was just passing through" He added as he went to turn away.

"Now hold on just a minute," She said as she grabbed him by the arm. "You don't have to leave on my account."

She motioned to the seat next to hers and James reluctantly sat down. He sat and stared at the wall in front of him, unable to muster the confidence to talk to this goddess.

"So, what's your name?" She said after eyeing James up and down.

"J...James." He responded quietly.

"James, I've always liked that name," she smirked. "I'm Victoria, but you can call me Vicky."

She spun James' stool to face towards hers. His eyes met hers for just a second before he looked down at his feet. He couldn't believe how beautiful this woman was and that she would choose to speak to him.

"So, James. What does a guy like you do for fun?" Vicky asked.

"erm, I don't really do much outside from sitting at home watching Netflix" He said.

"Don't you have a job or maybe a girlfriend?" Vicky inquired.

James couldn't help but blush. His mind began to race, could this woman really be flirting with him especially in such an obvious manner.

"N...no, nothing of the sort," He eventually responded "I've been unemployed for around a month now and I've n...never had a g...girlfriend before."

"Oh, well that comes as quite a shock to me," Vicky said with a surprised inflection. "Well, you've clearly been running around the wrong women."

James' heart began to beat faster than it ever had before, his cheeks reddened but he felt a strange wave of confidence wash over him.

"Haha, something like that." He chuckled.

"There's the James I wanted to see," Vicky smiled. "I like my men full of confidence."

"So what do you do for fun?" James asked as a smirk slowly appeared across his face.

"I have a small job, just something to keep me going but its client based so sometimes I go without work for weeks," she responded. "But my favourite thing to do is find a cute guy at a club and fuck his brains out."

Any confidence James' had mustered suddenly left him. His mouth hung open unable to form even the smallest noise. He wanted to smile and cry at the same time, a woman this attractive has just invited him to her house for what is sure to be one hell of a way to lose your virginity.

"What do you say we get out of here?" Vicky said as she grabbed James by the hand and led him outside.

They made their way to Vicky's car and all James could do was stare at her arse as it swung with her walk.

"Don't worry, you'll see it soon enough" Vicky chuckled as she opened the door to her car and sat inside.

James Climbed into the front passenger seat and Vicky grabbed him by the front of the jeans. On the drive home she only had one hand on the wheel as the other played with the front of James' pants.

The drive to hers was less than ten minutes but it seemed only seconds had passed for James between leaving the club and being sat on the end of Vicky's bed making out with her. Things began to get heavy very quickly as Vicky pulled her top off and buried James' head into her chest. She began to unbutton his pants and pull his trousers off then she started rubbing his balls as he sucked on her nipples. James went to remove Vicky's skirt but she slapped his hand away. She stood in front of him and pushed him onto the bed properly, James climbed his way to the pillows as Vicky stepped onto the bed and hovered her crotch over James's face. He could see she wasn't wearing panties, as he opened his mouth to speak she slammed her pussy over his lips and forced him to orally pleasure her. He could hear her moans despite her thighs covering his ears and squeezing his head.

As she was riding his face James heard a very alarming noise that sounded like the front door to Vicky's house being opened and closed. He tried to sit up and listen but the weight of Vicky kept him pinned down as she grabbed his forehead and pushed him down with all of her weight.

James heard footsteps make their way to the room he was in, the door opened and the footsteps continued to the end of the bed. James tried to look but couldn't see other Vicky's thighs as she continued to moan in pleasure and ride his face. All of a sudden she stopped and moved her thighs away from James' ears just enough so that his full hearing came back.

"Oh, did I forget to mention my boyfriend?" She giggled and she stepped away from the bed. James looked up and saw a tall muscular black man standing at the foot of the bed, was probably around 6'5" and his arms were the size of James's entire body.

"James, meet Tyson. He's your new master," Vicky said as she quickly strapped a collar around James's neck.

"And from now, I'm Miss Victoria to you" She added.

"You've outdone yourself this time baby," Tyson said with a deep and commanding voice "he's exactly what I want out of a sissy fucktoy".

James began to panic and tried to sit up but was quickly held down by Victoria who held him down by his shoulders.

"What is all this?" James cried.

"Well, the horrible truth is that I'm not enough for someone with the libido of Tyson. He needs two people to satisfy his needs but I'm just not a fan of him fucking another woman so we came to the arrangement that he could have a little fucktoy as long as it was a man of my choosing," Vicky responded. "Although I don't think we'll be using the word man to describe you from now on."

Tyson quickly grabbed James by the hips and pulled himself in between James' legs. Victoria sat at James' head and grabbed him by the ankles and pulled them into the air as Tyson pulled out his already erect 10" penis. Victoria leaned forward, placing her soaking pussy over James' mouth and sucked Tyson's huge member in order to lube it up for what came next. After a couple minutes James felt Victoria lean back and Tyson lean forward pressing his huge penis against James' tight butthole. After just a few seconds he pushed himself in and started pounding away at James' now burning arse. James began to cry out but was quickly smothered by Vicky's pussy.

Tyson fucked James for what felt like hours until finally they both came, Tyson inside James and James all over his stomach.

"He is gonna do just nicely," Tyson panted "especially after you work your magic on him."

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byBesissyb© 6 comments/ 29425 views/ 16 favorites

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by Anonymous

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by Anonymous06/15/18

Awesome story! Sure hope you continue soon!

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