Hello. This story contains strong content many will not find comfortable reading. Those things are boyxboy lemon scenes, rape, crossdressing, multiple partners, humiliation, and other things I can't think of right now. If they offend you it is best not to read. It should also go without saying that I do not own Digimon.
Takeru always hated when they invited him to these restaurants. Looking at the two lovebirds, Hikari and Daisuke, he always pictured himself in Daisuke's shoes being on the receiving end of Hikari's kisses. Yet here he was as a third wheel on one of their dates. He really hated him.
"Daisuke," Hikari said, "you need to quit taking those protein shakes or else you'll get too muscular."
"Well better too muscular than really skinny, Hikari," he replied as he sipped his water.
"What do you think, Takeru?" Hikari said as she finally acknowledged the blond boy. "Do guys look better skinny or muscular?"
"Why are you asking me?" he was really surprised by her question directed at him that he almost spat out his water.
She giggled. "No reason. Anyway, have you been hearing anything from your brother on how his first year of college is going?"
"Yeah, he said he finds it pretty boring. The music teachers are really making him hate music. He's thinking about switching over to aerospace engineering."
"Interesting." Hikari replied. "Taichi said he's really enjoying France. He's already got a girlfriend out there."
"A girlfriend?"
"Her name in Catherine, I believe. She's really beautiful."
Damn it, Takeru thought. I was thinking about asking her out soon. I'm 15, never been kissed, never had a girlfriend. At this rate I'll go to college a virgin. Speaking off…I wonder if those two…Nah, Hikari is only dating him because she felt bad for him. When I finally have sex both me and Hikari are going to lose our virginities to each other.
"Man," Daisuke interrupted Takeru's train of thought, "He's gone through more girlfriends than all of us Chosen put together. Granted, that's not much since all of us have only had one. Well except for…" he stopped before he finished his sentence.
He knew he was talking about him. All the other chosen have had one partner before. All except for him, that is. He figured that's why they always invited him, because they felt bad for him. However, Takeru still held out hope that it was because Hikari preferred his company as opposed to Daisuke's. Just as he was trying to gather his thoughts he noticed a purple-haired girl walk in. It was Miyako.
"What's Miyako doing here?" Takeru asked, waiving at her.
"Miyako?" Hikari looked back, seeing her friend.
What can Miyako be doing here? Takeru thought as she approached them. Wait, could they be trying to set us up? I know she recently broke up with Ken so she is available. Well, she's really pretty and I'm in no place to say no…
"How are you doing Takeru?" Miyako said as she put one arm on his shoulder.
They are setting us up. This is great!
"What are you doing here Miyako?" Hikari said as Takeru sipped his water.
"Today is supposed to be the day," she said while smiling. "Don't tell me you two forgot. I know Daisuke wouldn't forget such a big day like this." She continued giggling.
Then Daisuke's face lit up. "It is? This is great. Hikari we should go."
"No," Hikari interrupted him. "It would be rude to ditch Takeru after we invited him."
"Come one, Hikari," Miyako interrupted. "I know Daisuke isn't the only one excited for tonight." She put one hand on Hikari's hair and the other on her shoulder. "I know I am."
"Well, it was my idea." Hikari said.
Takeru had no idea what was going on between the three of them but it did not feel like they were setting him up with Miyako. What are those three so excited about?
"I'm really sorry, Takeru." Hikari told the blond. "But I forgot about a prior engagement with these two." She got up. "I promise I'll visit you tomorrow. Once again I'm really sorry."
And once again Takeru found himself alone on a Friday night. Well at least they paid the bill. He thought as he finished his water and walked out the restaurant. This isn't fair. My friends ditched me for God knows why. What am I supposed to do know?
"What do you look so down about?"
Takeru turned around and instantly recognized that person who called out to him as Ken.
"Ken? What are you doing here?"
"I'm just walking by, Takeru."
Takeru could tell that he was keeping something from him but he could not tell what. He also felt that Ken was studying him. Yet he was also feeling tired.
"Wait a minute, you live on the other side of town. I doubt you'd just be walking by."
Ken shrugged off his accusation. "Well you got me. I'm actually here for some business with Miyako."
"Miyako? I thought you two broke up?"
"Well people who've broken up can still be friends, Takeru. Especially when they've fought side-by-side to protect the world."
"Well I supposed you're right," Takeru responded
Ken walked closer to the blond. "And I mean, you and Hikari are still friends even though you still like her even though she's with Daisuke now."
Where did that come from? Takeru was shocked by Ken's sudden outburst. "I don't know what you're talking about, Ken." He was feeling really light headed right now.
"No need to hide anything from me, Takeru. Practically anyone can figure it out if they put two-and-two together.."
"Like I said, I have no idea what you're talking about." He was not only getting flustered, but felt he needed a nap real bad. "Either way, you'd be better off going back home. Miyako went with Hikari and Daisuke earlier for some reason."
"Figures she would," Ken seemed to know all about Miyako's whereabouts. "But my business doesn't directly involve her. She just did me a favor."
And at that point Takeru almost fainted. He was feeling light headed and knew that he had seconds before he fell on his face. But just as he was falling he felt himself being caught by Ken just before he hit the ground.
"You should be more careful, Takeru" Ken said as he held up the blond boy. "It'd be a shame if you were to scratch that face of yours."
"Ken!" the dark-haired boy had picked him bridal style. "What do you think you're doing? Put me down right now."
He had no energy to resist. He barely had any energy to stay up. But looking around he saw that no one was around. Try as he might, the blond boy feel asleep in Ken's arms, with his only thoughts being hoping that no one would see him in his predicament.
He did not recognize the room he was in. Looking around where he had just woken up he noticed that the room he was in was very elegant. It was also very pink. Everything in there was pink from the curtains to the bed sheets to the carpet. However, all that pink would not prepare him for what was underneath those sheets. Upon removing the sheets he could not believe what he was wearing. Getting up from the bed he realized that he was not wearing what he had been wearing when he was last conscious.
Instead of trousers and a shirt he was wearing a pink, frilly, Lolita-looking dress. The straps around his shoulders were white, just like the bow in the back of his waste. His skirt was about two-inches above his knees. And underneath that skirt he noticed that he was wearing a white petticoat that stuck out about half an inch over his skirt. Yet what surprised the blond boy the most came when he lifted his skirt. Instead of the pair of briefs he was wearing before he found out that instead he was wearing a pair of frilly white panties.
What is the meaning of this? Thought the blond dropping his skirt. Who would do such a thing?
"I see that you're up," said a voice that he instantly recognized as Ken's. But instead of seeing the Ken that he was used to seeing for the last five years he instead saw a figure that he had not seen since his defeat five years ago.
"Digimon Kaiser?" Said a surprised Takeru. "Ken, what is the meaning of this? Were you the one that put me in a dress? And what's the deal with the panties?"
"You sure ask a lot of questions for a slave, Takeru." Ken said as he walked closer to the crossdressing boy.
"I'm not a slave. Where are we, Ken?"
"Well if you must know we're in the digital world."
"The Digital World?" Takeru was surprised.
"Yes, the digital world. You did not have your D-3 on you when I searched you so you'll find that escape will be quite impossible. Now I suggest you present yourself to me so this can go smoothly for the both of us."
"Present myself? What are you talking about?"
"It means to get on your hands and knees and to relax your asshole."
Takeru was surprised by his words. Was Ken really talking about screwing him up the butt? He was not just going to let him have his way with him. "You're sick, Ken. I don't know what's gotten into you but you better give me back all my clothes and let me out."
"I burned those clothes." Ken said. "Those were boy clothes. What you're wearing now is suitable to who you really are."
"I have no idea what you're talking about. Now let me out of here."
"Make me," Ken smirked.
Angry, Takeru rushed the Kaiser hoping to take him out. But Ken saw it coming. Tripping the blond boy, Ken managed to catch him using his knees so that Takeru's stomach was on top Ken's right leg. Kneeling down and holding down Takeru with his left hand, Ken lifted Takeru's skirt and began spanking him.
"That's a bad girl" Ken mocked him as he spanked him. "If you ever do anything like that again it will be much worst for you."
Letting him go, Takeru rose back and grabbed his bottom.
"You bastard!" Takeru began forming tears in his eyes. "Hikari and the rest will know what you did. They'll come and rescue me."
"Please." Ken began laughing in his face. "They're all too busy with their lives to care about you, some dateless freak."
"That's not true. Hikari…"
"…thinks you're gay which is why she likes hanging out with you."
Takeru blushed. "She doesn't think I'm…"
"Everyone does."
"You're lying."
"Am I? Think about it, you'd think she'd still be close to you while dating someone else? Face it, kid, you'll never be with a girl now."
Takeru could not believe it. "Even if what you said was true they'll still find me and…"
"You still don't get it, do you? While you're stuck here rubbing your bottom Hikari is having… let's just say some fun with Miyako and Daisuke. You are the last thing on anyone's mind."
It then hit Takeru. Everything made sense now. So that's what those three were up to. That bastard Daisuke! How is it that he is doing that while I'm stuck wearing a dress.
"This isn't happening." Takeru said. "This is like some twisted nightmare.
"I'm afraid it is happening, Takeru. Now, prepare your anus."
Grabbing the petite blonde by the wrist Ken twisted Takeru's arm and now held him with his arms behind his back.
"My god, that took no effort at all. No wonder Hikari never saw you as a potential partner: she saw how wimpy you are." Grabbing the young feminine boy's long hair Ken dropped him on his stomach.
"Wah!" Takeru whimpered. Kneeling down over him Ken lifted Takeru's hip while leaving his head on the floor. Lifting up his dress and petticoat Ken was enjoying the sight of the blonde's ass covered in frilly panties.
"With your ass up in the air presenting yourself to me you look so rapeable right, Miss Takaishi."
Rapeable? Then it hit him: here he was, facedown down ass up, with his panty-covered ass in full view. Being forced to crossdress it hit him that he was set to be Ken's new girlfriend. Worst off all he was about to have his virgin anus forcible penetrated.
"Please, no," the blonde cried out as he failed to escape from his captors grip. "I don't want to take it up the ass! I'm straight," tears began coming out of his eyes.
Ken began stroking his new slave's hair. "What you want is of no concern to me." Grabbing the panties by the waist band Ken slid them down to his knees.
Takeru started bawling his eyes out. "Please my first time can't be with another guy while I'm dressed like a girl!"
"Dressed like a girl?" Ken said as he grabbed Takeru's member. "It can't be more than 2 inches. With a dick as small as that you practically were a girl. And like a naughty girl you're going to take it up your bum."
Girl? Takeru thought as he felt his butt cheeks spread. He's trying to turn me into a girl. Any minute now Ken is going to stick his penis up my asshole. And with little warning Ken's large 10 inch penis penetrated the blonde's virgin bottom bareback, breaking his behymen.
"Ahh!" Takeru let out a high pitch scream. "No, please." Takeru could feel Ken's 10 inch penis fill the insides of his anus as Ken's every thrust caused the blonde exponentially more pain. And yet, much to Takeru's chagrin, every time Ken pulled his penis back and forcibly shoved it back in, he felt a bit of pleasure from the pain it was causing him. He was still in pain from his asshole being stretched out due to having another man's penis inside of him, but that pain was causing a small sensation every time his prostate was rammed. Still, the small pleasure he was receiving from being sodomized wasn't enough to make the uncomfortable feeling of being drilled up the ass and the humiliation of all that happening while wearing very effeminate clothes to go away. Crying more than he'd ever cried before, he tried to plea with his rapist. "Ken, please, take it out already. You made your point."
"Call me Kaiser, bitch." Ken said giving the submissive boy a hard thrust. Feeling the lustful drive of his new master, the slave knew it was best to comply. Plus, resist as he might-with the clothes he was wearing, his butt impaled, and what had happened earlier with Hikari, Miyako, and Daisuke-he knew that whatever relationship he was now in with the Kaiser he would always be the recipient of Ken's libido, and should just accept it. Takeru would accept being the uke to Ken's seme.
"Please, Kaiser…" Takeru could not even finish his sentence as the pain kept causing him to cry.
"Please, what, bitch," Ken mocked his bitch as he kept humping the blonde. "I want to hear you denounce your manhood. I want to hear whose little bitch you are."
Damn you, Ken, Takeru thought as he tried to muster up the ability to form coherent sentences. God his massive penis in my ass is the most uncomfortable thing ever. And to think that Daisuke is having a threesome with both Miyako and Hikari right now while I'm in a dress. I guess it's only fitting that the worst night of my life ends with me getting raped and taking it up the ass like this. I wonder if he'll ever let me wear pants again, or at least no more wearing panties. God this is so degrading.
"I'm your little bitch, Kaiser. Please, Kai…" but the pain was too much for the sissy. Not being able to control himself he just began crying, accepting his newfound fate as a gay sex slave. The Kaiser, not being done with his fuckboy, knew he had to humiliate him some more. Pulling out a ball gag Ken, still in the process of deflowering Takeru, reached towards Takeru's head and stuck the ball gag in his mouth.
"Mmm," With the ball gag in his mouth and a dick up his ass that was all Takeru could say, still tearing up.
"Yes," Ken screamed, "take it like a bitch, Miss Takaishi."
Why me? Takeru thought realizing he was about to spend his life never once being on the giving side of sex, only the receiving. I was supposed to be the one doing the penetration with Hikari, now instead I'm the one being penetrated. Damn that Daisuke. This isn't fair and his dick so damn big! I'm so going to feel this in the morning. He could not scream. He could not escape. And he knew that after this sex session it would be a while before he would be able to walk since he could feel his asshole sore. Eventually, due to Ken's large penis stressing out his asshole, Takeru began feeling light headed and knew that he was about to pass out soon. And within a minute, after giving in to getting his butt plugged, Takeru passed out just as Ken finished playing with his new boy toy, releasing his load into his asshole. Pulling out his non-erect penis from Takeru's asshole, the Kaiser admired his work and what it did to the petite blonde.
He could barely handle that. Ken studied Takeru's unconscious body, which was still positioned ass-up with the panties now around his ankles and semen coming out of his asshole. He's going to need a lot more conditioning if he's going to have the honor of being my girlfriend. Walking away from the passed out boy Ken walked towards one of the bookshelves, revealing a camcorder. She kept her end of the bargain, and now I'll keep mine.
Walking over to the blonde Ken whipped off the excess cum from Takeru's bum, slid the frilly panties back on, lowered his dress, and picked him up in the bridal carry. With the unconscious boy safely cradled in his arms he walked away towards his knew room.
AN: well there it is, the first chapter. Poor Takeru, having to be humiliated by Ken like that knowing that his rival is off enjoying himself. I'll try to update as soon as I can but with school taking up most of my time I'm not sure how often it will be. Please read and review, thank you.