Shinji Okazaki vs. Teddy Roosevelt

Match Type: Hentai
Winning Condition: The wrestler must make their opponent cum from the front and the back. Whoever accomplishes this first will be declared the winner

Shinji sat on the bench and thought about where he came from to get here. He was in another hentai match in Tension. The boy was really into the first one, loathe admit it, but here he was again. The winning conditions were different this time- in order to win, he had to make his opponent cum vaginally and through her ass. The joys of anal were unknown to him, both giving and receiving. A shudder ran down his spine. Would a woman really embarass him by taking him in the ring?

The manager had informed him that his next opponent would be a rookie so that was some consolation. It wasn't much of a consolation as he was a rookie as well. At least he could hope for a woman who was as skinny and frail as he was. He stood up and straightened out his dress. It was a very pretty shade of blue he thought and he looked wonderfully feminine. His stockings were straight and clean and one of the worker's gave him an assist with his makeup so he was looking stunning. Shinji made his way to the staging area and peeked out from the curtain into the arena. It was packed and the crowd was bustling with excitement. Hopefully at the end of the night they would be chanting his name.

Shinji closed the curtain and took a deep deep breath. Showtime. Time to triumph, fuck a beautiful woman, and win. His music started up and he walked out into the arena. The crowd cheered and Shinji waved and smiled as he strutted down to the ring. He had a good feeling about tonight. One way or another he was going to come out on top. He hopped into the ring and waited for his opponent.

If nothing else, let her be pretty, he thought.

Teddy was mildly confused by the fact that she was to be in a Tension match, but she didn't particularly mind. both the male and female body were meant to be wrestled down and played with, Teddy often told herself, especially during her time wrestling back home. A match against this so called Shinji would be just like a match against another girl, hell, it'd even end with one of the two getting a dildo in their mouth.

Thus, she walked down towards the ring with pride, her hips and body in general made some very sensual movements, as her entrance music blared throughout the arena Teddy was wearing nothing more than her standard attire (which wasn't much to begin with), with the minor addition of a good, long, thick vibrating dildo she chose specifically for having fun with her opponent's ass.

As she finally entered the ring, she was confused once again by the 'girl' in front of her. "Well, it appears either the definition of man is a bit different here in Japan, I've just been fooled fighting a lady, or you're in the wrong place, lass." She said, unaware of the fact that the 'girl' in front of her was Shinji.

Oh dear lord. The woman striding down the ramp looked like a titaness of combat. Her outfit was lewd in the extreme and the dildo she had was...there were no words for it. The woman towered over poor Shinji and was easily half a hundred pounds heavier than him. The girl was certainly embonpoint and quite muscular to boot. Shinji visibly gulped and stared at the ground. He felt he didn't have a snowball's chance in hell tonight.

"I am Sh-sh-Shinji." Shinji stuttered. He couldn't even look at this boisterous, proud woman. "I am to be your..." Shinji adjusted the collar of his dress, "opponent this evening." His voice was like a little flute, dipping and weaving in and out. He hopped from one foot to the next.

He looked at the ref girl and prayed she wouldn't start the match, like this whole thing was one big mistake. Shinji tried to make eye contact with Teddy as best he could.

It took him opening his mouth to reveal to Teddy that her opponent was in fact, a boy. "Oh, I see, well, I'm not one to judge." She said, realizing that he was also terrified out of his wits. It made sense, they probably hadn't told him that he would be fighting a plump, well built woman of war, just like they didn't tell her she would be fighting a crossdresser.

"Well, you certainly don't look so proud of yourself, you know what, I think I'll let you have the first strike, c'mon, don't be shy, I want to see what you've got." She said, pointing at herself as the bell rang behin them, hoping to encourage him to 'man up', so to speak, and at least try his best. And while she didn't make it outright obvious, she also wanted him to try his hardest, as the only thing she liked more than defeating someone was to defeat someone after a hard fought battle.

Two things happened both of which confused Shinji. First of all, his opponent for the night offered to let him have the first hit. It seemed like some sort of trap or something, but the woman seemed strangely...earnest? That was something new in the ring. And then the bell rang. Which meant that the match was officially on. Point of no return.

Shinji took a tentative step forward and then another. Soon he was right upon Teddy and looking up at her the way a pious man looked up at a stained glass window. "Are you s-sure?" Shinji reared back and launched the strongest punch he could muster. It wasn't much considering his nodle arms and awful technique, but it was all the boy could manage. The blow was aimed at her shoulder- something stopped him from aiming it at her face. Shinji wasn't quite sure what it was.

Teddy was admittedly mildly impressed by Shinji's strike. It had certainly been strong enough to hurt and make her upper body move slightly backwards, even if it was let down by his weak strength and technique. "Well, that's not too bad, I've seen worse." She told him. Suddenly, she took a wrestling stance, her knees bending down a little and arms seemed to be ready for some sort of armlock.

"Well, I hope your ready for this next part." She said, as she prepared to lunge at him. She wasn't sure what she expected him to do, but she did expect him to at least do something to stop her massive force from coming down on him like the fury of a god.

Well she had seen worse. So that, at the bare minimum, was good news. And it even looked like it hurt a little bit which was also lovely. Considerably less lovely was Teddy who looked like a bear about to eat a deer. Her arms were at the ready and her legs were cocked like a rocket on its launchpad. And poor Shinji stood there with a gormless look on his face.

And then he tried to leap into action. Shinji was not a particularly strong man but he had a little bit of speed to him. The problem was trying to get his sort stubbly legs pumping as quickly as he could to try and get out from under Teddy. He dashed to the side in a bid to not get crushed.

Teddy found herself launching herself at a greater speed than she usually manages towards her opponent, albeit still not particularly fast. However, it was fast enough to grab one of his legs as he tried to dash, finding herself falling belly first onto the mat just as she grabbed it. "Oomph," She grunted as she hit the floor, only to realize she had managed to at least grab onto her prey. "You're mine, darling." She said, as she tried to grab onto him as she proceeded to get up.

Shinji was so close to a clean break. The vast expanse of the mat called to him as it would mean his freedom from Teddy and sexual humiliation. But just like so many things that were dangled before him the rough hand on his leg informed him that the dream wasn't to be his. He collapsed to the mat with a rather unimpressive "Gah!" and clawed at the mat to try and squirm his way out of Teddy's grasp.

But it was all to no avail. The arm was still on his leg and Shinji was a mouse in a trap. He rolled over to try and least figure out some way to defend himself from Teddy. He knew that the woman would have her way with him if she was giving it her all, but Shinji was going to at least put up a fight. The crossdresser threw his arms out in front of him to try and throw up some semblance of defense.

Teddy found herself having to stop herself from chuckling as she saw Shinji attempt to fight back, His arms practically bouncing off of her. Teddy was respectful, but she couldn't resist the idea of playing with her food. Without any warning, Teddy decided to let go of Shinji, instead standing over him like a towering behemoth. "You might need to work on your defense a bit Shinji." She replied, more naughty thoughts brewing in her mind. She would then begin to slowly walk towards him, determined to up the ante a little.