Shinji Okazaki vs. Teddy Roosevelt

Shinji's head rolled back as Teddy began toying with his erect cock. That's all she was doing, toying with him- as she gracefully moved her hand up and down his member he knew that there was more pleasure, and almost certainly more pain, to come. The crossdresser moaned and closed his eyes as he was being played with.

He opened them again as he felt himself being pulled towards her. She kissed him, passionately. The crossdresser kissed back, introducing his tongue into the mix and the crowd went bonkers. They were cheering and Shinji was feeling good until he felt the plastic of the strap-on against his skin. It was a callous reminder of what her intentions were and those were intentions Shinji didn't want to see carried through. He pushed back, weakly, trying to escape her clutches.

Teddy moaned gently as she continued to kiss the smaller Shinji, still stroking his cock through his panties. She could begin to sense that Shinji was still aware of the match at hand, feeling him try to push away from her. In response, she moved her arms, now trying to wrap them around his waist, and begun to bearhug him, now carrying him towards the center of the ring.

Poor Shinji. He just wanted to wrestle a little bit and have some fun. The fun part was plain to see and it was pretty exciting to be kissed by a powerful and dominant woman. Being crushed by a bear hug and carried like he was nothing was considerably less fun. Shinji flailed against the clutches of the bear hug to no avail.

He was hers and he knew it. They were both in the center of the ring, far from any rope breaks or anything else. Whatever was coming next, Shinji just had to take.

Teddy, now having Shinji in a nice, good spot, begun to try and flip him upside down, wanting his head to be next to her strapon for what was about to ensue. "Shinji, would you kindly put your lovely little mouth on my cock? Don't worry, I'll be gentle." She told him in a eerily motherly voice, seemingly growing kinder now that he was at her mercy.

At the same time, she took a nice look at his panties, now right in front of them, she begun to lick his member through them, slowly kissing, licking, and nibbling on it to further arouse him. "Teddy wants to make sure you have fun while you lose, lovely little boy." She added, now attempting to press the strapon gently against his lips.

This was new. Standing 69, in the middle of the ring. Shinji did as he was told like the obsequious little slut he was. He inched his lips forward onto Teddy's massive strap-on. The toy was probably going to be inserted into him later, so hopefully this would make that ordeal a little bit...easier. Plus, Teddy was giving him a little pleasure.

Shinji squirmed in the hold. Not really to try and get free, but because of the pleasure he was receiving and the pleasure he was about to get. His little legs kicked playfully and he closed his eyes.

Teddy, now feeling Shinji's mouth tug gently on the strapon, begun to thrust her hips. She started out slowly, not wanting to choke him or anything, simply to rub in the fact that his mouth was about to get fucked. She kept going until she could feel Shinji's head press against her groin, then slowly beginning to thrust back, each time slowly increasing her speed.

Of course, it wouldn't be a standing 69 if she wasn't playing with his member. After playing with his cock, she finally used her free hand to try and yank the panties right off, feeling the stretching panties press against his wiggling legs. Once that was done with, she began to lick the tip of his cock, deciding to service him as well.

Shinji was beginning to slobber all over Teddy's toy. Long spindles of his drool fell down to the mat as he lapped up Teddy's strap-on. It was being forced into him- Shinji no longer had control over his body. Teddy proved it by grabbing his panties and ripping them off! And then she rubbed it in by lipping the tip of his cock sensually.

The crossdresser moaned. It felt good. Beyond good. The boy moaned, or moaned as much as he could with his mouth full.His toes began to curl as Teddy played with him...

Teddy slowly sped up her thrusts, feeling his drool hit parts of her foot. She liked the feeling, still continuing to face fuck him as she begun to start on his cock. She slowly began to take it in her mouth, making sure to pleasure him as much as possible. She took a look at his toes, nearly wanting to play with them, only stopped by the lack of reach on her free arm.

Shinji's arms that once hung loosely were now clawing at the mat. His moans became louder, more primal. Wave after wave of pleasure was crashing into him and his body was responding in kind. All of his thoughts circled around Teddy and the sexual euphoria she was giving him. The crossdresser squealed as Teddy pleasured him with her skilled mouth.

He knew that he would soon be reduced to a cumming, sucked to death mess. But that was in the back of his mind right now. At the forefront was the intense ecstasy of Teddy, which made his eyes roll around in his head. This was all just so much.