Digimon Fan Fiction ❯ Just One Night ❯ Chapter 1

Warnings: Explicit sex and cross dressing. I'm not sure why the second one is a warning.

This story is so AU and not very realistic but I had to write it. Koushiro never gets to have any fun, so I let him ^_^

Disclaimer: So I don't own Digimon, but I do own Digiman. . . . Okay, I don't own that either.



"Fine!" Taichi Yagami yelled as he slammed the door shut and climbed into his black Porsche roadster. He didn't bother putting on his seat belt, and he pulled out of the driveway so fast the tires left black streaks on the cool gray cement.

His head was absolutely spinning from the fight he'd just had, and he turned the corners at random, not really knowing where he was going.

"God damn it!" He cursed as he looked around at the unfamiliar buildings surrounding him. "The stupid bitch," he muttered, "had to have one of her mood swings in a city I don't know."

After driving around for a a little longer and talking to himself Taichi had to admit it. He was lost.

When he looked out of the window he saw seedy buildings and dark alleys. He was definitely not on the right side of town. Not that he was overly worried for his safety, but his car could be in danger since it was very expensive and unique.

Finally, Taichi spotted a group of women, or more correctly girls, standing on the street corner huddled together. He didn't have to look twice to realize what these girls did. It was written all over them from the way they stood to the clothes they wore. But apparently these providers of the worlds oldest profession were having a slow night because they all stared at the black Porsche as it slowly drove by.

Or maybe they've never seen a Porsche before, Taichi thought as he watched them. Then he was struck by an idea and turned around to drive back to the waiting prostitutes.

As he rolled down the window he was greeted with stunned silence. So, they obviously haven't seen a Porsche before, Taichi smiled to himself and then spoke. "Does anyone know how to get to the Four Seasons from here?"

One of the whores smiled brightly and said, "only if I get to stay with you."

"Maybe," Taichi responded before he thought about it. "Let me see all of you."

With that request the whores lined themselves up so he could get a good look at them. Upon closer inspection he realized that a few of them were drag queens and he laughed to himself for the mistake. Then he noticed one. She was a bit taller than the rest of the girls and had shoulder length blonde hair. She looked a bit wiry and she didn't have a particularly pretty face for a girl. But her eyes were like black diamonds. Coal black and shiny. And the way they looked at Taichi sent shivers down his spin.

"You," he said pointing at the blonde, "what's your name?"

She shifted her feet and stood up a little straighter. "Izzy," she said. Her voice was deep, but strangely alluring and Taichi leaned over and opened the passenger door.

"Do you know how to get to the Four Seasons?"

Izzy nodded and reached for the door. Her eyes still firmly locked on Taichi's.

"Then get in so you can show me," Taichi said and Izzy climbed in. Then Taichi put the car in drive and raced down the deserted street.

"You need to get on the freeway heading north," Izzy said without looking at Taichi.

"Right," he said and glanced at the girl next to him. She couldn't be more than 19 and it made him wonder exactly how many laws he would be breaking tonight. Well, at least getting directions isn't a crime, he thought, even if they are from an underaged hooker.

"Are you going to pay me for this ride or am I invited up?" the young girl asked and finally looked at the john. Her voice was deep and smooth almost like a purring cat.

Taichi smiled playfully. "I'm not sure yet," he admitted, "I haven't done this before."

Izzy merely nodded. "Take a left at the next exit and it will take you to the hotel," Izzy explained. "And I will be requiring some type of compensation for this transaction, even if you don't invite me up."

Taichi rose and eyebrow and looked at his passenger. She was looking out of the window so all he saw was the back of her blonde head. His eyes then traveled down to her legs. They were slender but strong, like the rest of her. And with a vocabulary like that she was obviously smart to boot.

"I'll give you $100 for the ride and cab fare to where ever you want to go," he said. "Of course that is if I don't invite you up. If I do you'll get a lot more."

Taichi knew she would turn and look at him, and she did. Her black eyes silently questioned his last statement, but she said nothing.

After a moment of staring her voice broke the silence. "Well, it is $50 for a hand job and $100 for a blow job. Everything else is priced upon request."

Taichi smiled at her business like tone. "No offense but isn't that a bit expensive?"

"I figured you could afford it," Izzy said and pointed. "There on the right."

Taichi followed her finger and saw the hotel. He quickly drove over and pulled up to the valet.

"I think if would be best if we further discussed our business arrangement in my room."

Izzy nodded and waited for Taichi to climb out before following him into the hotel and up to his penthouse suite. Fortunately, it was rather late at night and there were no patrons in the hotel so only the staff saw the beginning of Taichi Yagami's indiscretion. But of course they would keep it in the strictest of confidence.

When they arrived at the top floor Taichi slide the card and walked into the room. He had only been there once since his arrival the day before and that was to drop off his luggage. The rest of the time he had spent with his girlfriend. But now here he was again and with a hooker no less. He shook off that thought and flipped on the light switch before collapsing on the couch.

He looked over at Izzy who was slowly removing her jacket and draping it over a chair. Her movements were deliberate and smooth but not very feminine. In the light Taichi could also make out how boyish her body was. She didn't have any hips and her shoulders were wide. Her arms had the same slim but strong build as her legs and as she turned around to face him Taichi realized the reason for all this. Izzy wasn't a girl.

"You're a boy?" Taichi said before he could stop himself from sounding too shocked.

Izzy stood there for a moment watching him and took a step back. "You didn't know? I'm sorry but I thought it was pretty obvious."

In the light Taichi saw that she, or rather he, had a point. It was obvious that he was a boy in women's clothing. A women's miniskirt and tank top to be exact.

"It was the light," Taichi said and chuckled to himself. "I can't believe I thought you were a girl. You aren't even a very pretty girl."

"Well," Izzy said and reached for his jacket, "since you won't be needing me I'll be taking my money and going. $40 should be fine for the cab."

Taichi watched Izzy pull the coat on and turn toward him. His eyes, those unbelievable black depths were searching him again for an answer. Boy or not Taichi was very drawn to him.

"Wait, let me see you without the wig for $30," he said and pulled out his billfold.

Izzy nodded and slowly pulled the blond wig off of his head. Underneath his hair was short and deep red. Then the boy ran his fingers through it to give it some life after being trapped under the wig for so long.

Taichi couldn't help but smile. "You look a lot better as a boy, you know."

"I hope so," Izzy replied.

"So why do you dress up like a girl? Aren't most of your clients men anyway?"

"Well, I get more business as a girl because some guys don't care what's under the skirt as long as I have hands and a mouth," Izzy explained.

Taichi was slightly disturbed at Izzy's explanation but he figured he wasn't one to judge. Then without thinking he said, "what's under the skirt?"

"That'll be $50," Izzy said without any idea how strange this was for the man in front of him.

"For what?"

"To see what's under my skirt. $50 more if you want to touch anything."

"Fine," Taichi said and pulled out a one hundred dollar bill.

As soon as he did Izzy began to unzip the black mini skirt at the hip and gently nudge it down his thin hips. When it was right above his member he stopped taking off the skirt and removed his jacket once again. Then he slowly pulled the tank top over his head. After he had tossed them both aside Izzy returned his attention to the skirt.

Taichi watched him with rapt attention. He could see a peek at the boys red pubic hair and for whatever reason it excited him. He wanted nothing more in the world at that moment than to see Izzy au natural. And he wasn't disappointed.

Once the skirt dropped Taichi started to drink in the young man's body. It was slender but he could see the taut muscles under the surface that gave a nice amount of definition to his chest and arms. Then Taichi's eyes wandered down to the nest of hair between Izzy's legs. His cock hung limp but even so was quite large despite. Just at the vision of it Taichi felt his own pants tighten.

Izzy noticed his predicament and walked over. "It's $150 for me to relive that with my mouth."

"I thought it was only $100," Taichi said and smiled at the young man's proximity to himself.

"Well, I don't think you are in any position for negotiation," Izzy said and smiled slightly.

Taichi noted that it was a very warm smile and that the boy had slightly pouty lips. As he watched Izzy's lips he began to imagine them around his expanding shaft and breathed heavily. "Yes," he said without hesitation and got up to remove his pants.

As he was doing that Izzy walked over to his jacket and retrieved a condom. When he returned Taichi was standing with his pants down and his own large member standing at full attention. He smiled as Izzy lowered himself to his knees.

"My name is Taichi," he said as Izzy unwrapped the condom. For some reason he felt Izzy had a right to know the name the man whose dick he was about to swallow.

"All right Taichi," Izzy said as he rolled the condom on the other man before wrapping his lips around the tip of Taichi's cock.

Reflexively Taichi thrust his hips slightly and moaned loudly as Izzy worked with his mouth and tongue. Taichi felt like he was drowning in pleasure as he watched the red head swallow him whole. Izzy was making him feel like he'd never felt with anyone before. He didn't want the feeling of the warm wet mouth around him to ever end. Izzy tongue was doing things no girl had ever done to him and it was pushing him closer to the edge with every lick.

Finally Taichi succumbed to the pleasure and let out something between a scream and a moan. Then he whispered, "Izzy," as he collapsed back on the couch.

Izzy sat back on the floor to let the older man recover and watched him intently. It didn't take long for Taichi's to get over the rush and he sat up and looked at the boy on the floor in front of him.

"How old are you, Izzy?" he asked as he pulled off the soaked condom and disposed of it.

"18. Why? How old are you?"

Taichi smiled at his brashness. "I'm 29, and I just thought you looked a little young."

"That's because I am," Izzy said as he got up off ot the floor. "Now, with that be all for this evening or were you planning to experiment in other areas of homosexual sex?"

"Umm, like bu. . . ."

"Anal sex?" Izzy said as Taichi hesitated. "Yes, there is that. It will be $500 for one session or $1000 if you want me to stay all night."

Taichi just smiled and set his billfold on the table. "I might as well splurge."

"All right then," Izzy said and pulled out a bottle of ky jelly and some condoms from his jacket. Then he sat on the bed and looked at Taichi.

"Listen very carefully. You have to loosen me up first so put some ky on your fingers and stick them in gently one at a time. Got it? Then you can insert your penis."

"Wait a minute," Taichi said, "I'm supposed to do that to you? What if I wanted it the other way around?"

Izzy studied him for a moment. It was one of the only times he'd been stunned into silence.
"No one ever wants it that way," he finally said.

Taichi smiled as he pulled off his shirt and sat next to Izzy on the bed. "I do," he said and laid back.

"All right," Izzy said and turned to face Taichi. He was a very good looking man with golden skin and a bush of brown messy hair on his head. He was well toned and Izzy had to admit this was probably the best job he'd ever done.

"You need to either lay on your stomach or put a pillow under you lower back to give me better access," Izzy said as he spread the gel on his fingers.

Taichi complied and grabbed a pillow off of the bed and propped up his backside with it. He wanted to be facing Izzy when they had sex.

"Are you ready?" Izzy asked and Taichi nodded. He body was trembling with the excitement of a new pleasure and he didn't trust himself to speak.

Slowly Izzy inserted one gentle finger and Taichi's body reacted immediately trying to push it out. But he kept his hand steady and expertly moved it around until Taichi gasped with pleasure.

"Found it," Izzy said and smiled to himself.

Next, he inserted a second finger to join the first. Taichi wriggled with excitement. He couldn't get enough of Izzy being inside of him.

"Put in another one," he whispered.

Izzy nodded and inserted the third finger. He moved them around gently and Taichi moaned.

"I think you're ready," he said and pulled out his fingers to put on a condom.

All Taichi could manage was a nod.

Izzy had felt himself stiffen as he loosed up Taichi, which was odd. He never got off on johns, but now he had. He refused to think about it though as he lubricated his enlarged member. Taichi was good looking and that was all!

When he was ready he positioned himself and lifted up Taichi ass to give himself better access. It was firm like the rest of him. Izzy slowly inserted his cock and started moving it in and out. Taichi was responding by pushing himself into Izzy every time the young man thrust forward. He couldn't get enough of the mixture of pleasure and pain that was pounding into him and he moaned loudly with every thrust.

Izzy was also becoming lost in the motion. He knew Taichi was enjoying it from his movements and he looked forward to every thrust when his balls would smack against Taichi's ass. He tried to hold back but he found himself moaning loudly as he pounded into the older man.

After a few more passionate thrusts Taichi exploded shortly followed by Izzy. Both of the men collapsed together on the bed, too tired to say much of anything but both with very big smiles on their faces.

Taichi didn't remember falling asleep but when he woke he saw Izzy putting on his black boats. The windows were pale blue and as far as Taichi was concerned it was far too early in the morning.

"Going so soon?" he asked as he pulled himself out of bed and walked to the table with his billfold.

"It is morning," Izzy said and finished tying up his boots.

Taichi walked over and handed him $1500 in $100 bills. After Izzy counted it he looked up at Taichi with his burning eyes.

"This is $1500, you only owe me $1340."

Taichi smiled and nodded. "I added a bonus because I want you to do something for me."

"What?" Izzy asked.

"Tell me you real name."

Izzy was silent for a moment as he looked at the money, then he said, "Koushiro Izumi."

Taichi nodded, "Then have a nice day Koushiro, I'm going back to bed."

Izzy only nodded in response and quietly let himself out, but Taichi had once again been claimed by sleep.

Later that morning at a decent hour Taichi woke for a second time. He scanned the hotel room, but Koushiro was long gone. He got up slowly and went to the bathroom for a morning shower. He knew he had a lot of explaining to do. She would cry and scream but it was for the best, their relationship wouldn't have worked out anyway.

Plus, now Taichi Yagami had a new plan on what to do while in this city. He had to find one Koushiro Izumi.