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Inaugural Crossdress Sexfight Ch. 03.5

After losses to Tommi, Jaimie and Dani, it didn't take a genius to realize that I had become the defacto jobber of the Crossdressing Sexfight League (CXSFL). There wasn't a cock among them that hadn't been in my mouth or ass at some point and if we had kept standings, I would have been in dead last place. Unless I wanted to accept my jobber role within the league (which did have its benefits...), I needed to do something.

After giving some thought to each of my matches: dominated completely by Tommi, a nearly even match with Jamie and completely thorough domination by Dani, the logical choice would have been Jaime. But I didn't just want to win, I wanted to make a statement win -- a choice that would either be the best or worst decision I had made in some time.

I decided that a re-match with Dani -- who had the biggest cock of the trio I had faced -- would be the best choice since he was essentially the top gurl of the league at this point. A win against him would give me some serious credibility with the other gurls where a loss wouldn't come as any type of surprise. It seemed like I would have everything to gain and nothing to lose - outside of 8 long inches of hard cock filling my ass and mouth once again.

Unsurprisingly, Dani was more than receptive to my request to a re-match and said I must have enjoyed being his bottom like the sissy bitch that I was. Clearly, if overconfidence was something to be used against him, there was plenty of opportunity to exploit that. The twist for this match is the that loser would have to have the winner's name written on his ass in large letters in permanent ink which, while not necessarily permanent, would linger long enough to make any public exposure quite humiliating.

For this event, there would be no referees -- just a few cameras on tripods to record all the action. Dani arrived in his newest outfit which was a pink halter tops, white bikini bottom with pink polka dots and blue ties on the side, and 4" pink pumps. I counted with a short pink tip, tight black boy shorts with an aqua thong and 6" open toed platform sandals. Clearly it would seem I had chosen style over functionality but this time I wanted to leave as much material between my cock and ass and him.

The permanent marker was on prominent display on a nearby table as a reminder of the price of losing this match and I had already been a bit worried about how long it might be before I could go to the gym and shower again if things didn't go my way.

We both moved to the center of the circle and I could see the confidence in Dani's eyes as he approached. Just the outline of his massive cock bulging in his panties forced me to take a deep breath to try and calm myself a bit.

"You must really love my cock slut" he said as he approached me. "Our last match wasn't even close, so I can only assume you missed being my bottom bitch so much you need a re-match. Don't worry, after I'm done with you, I'll leave you with more than just my cum all over your sissy ass." He laughed as he nodded toward the marker on the table.

Rather than letting my nerves (and cock) continue to grow, I took advantage of his temporary distraction to quickly slip past and behind him. Before he could react, I had him in a full nelson with my hard cock pressed up against his bikini covered ass. "Oh shit!" I heard him whisper as his hands were pinned up helplessly over his head. I took a few seconds to enjoy this moment as I had no idea how long it would last, but it felt so good to control him for even a few brief moments.

I could feel and hear him struggling and trying to get himself free, but I just held on until I could develop a plan. He was trying to work his legs between mine to trip us hoping the break the hold, so I took advantage of one of the attempts to get us down to our knees and then rolled onto my back so that he was on top of me. While he attempted to roll us over, I worked my ankles in between his legs and slowly stretched them wide which gave me more stability and also left him more exposed.

I was intoxicated by the feeling of control, but wasn't in any position to make him cum. I knew that I needed to come up with something, but for now this felt pretty good. In actuality it began to feel too good as he had decided that if he was in this position, he was going to have to use any advantage he could. I could feel him slowly gyrating his hips which had his ass rubbing up against my cock. Between that and the high I was getting from having control, I could feel my excitement begin to grow more quickly.

I couldn't allow myself to lose this match after appearing to have such an early advantage, so I needed to think of something quick. I quickly moved my legs from between his and used my own leverage to roll us over so that he was face down and I was on top of him. I knew his arms would be starting to get tired, so I took a chance and replaced my two arm hold with a single arm holding both of his in place. I then used my free hand to reach down and untie his bikini bottoms. In just a few seconds they were free and it took all of my will not to just enjoy having my bulge rub up between his sexy ass.

I could almost begin to sense a change in him as if he was started to realize that things were not going as he had planned. At the same time, I could feel my confidence growing as my plan was starting to come together. With his arms tired from the hold, I took the opportunity to quickly release the hold and before he could regain his strength, I brought his wrists down behind him and quickly used his bikini bottom to bind them together.

"Nooo..." he cried as he was helpless to stop me. I now had him bound and without any bottoms! Not only was I going to win, but I now had the luxury of how I was going to finish this match. I decided to enjoy things a bit, so I removed my boy shorts and thong and then stuffed my thong into his mouth.

"That's to muffle the inevitable moans and give you a little taste." I said as he did his best to protest in vain. I knelt between his legs and spread them out with my knees. His sexy ass was not fully exposed in front of me and I quickly applied a few sharp smacks onto each cheek to add a little color. I enjoyed hearing the light gasps with each smack and I could only imagine the thoughts running through his head as he contemplated how this could have happened.

I wet my finger and slowly ran it down between his cheeks and stopped when I reached his ass pussy.

"Hmmm...what do we have here?" I said in my most teasing tone. "Looks like a cock hungry sissy ass."

Without a need to hear his response, I slowly began working it into his ass. I could feel his squirm but he was in no position to stop me. I could feel his ass pussy resist my finger, but with every cycle, it became less and less until I was working it in and out pretty quickly.

"Don't worry," I said, "the real thing will feel so much better!"

Having enjoyed that preliminary fun, I rolled him over and sat him up. Slipping in behind him, I looked over his shoulder as I grabbed onto his large cock which was hard as a rock.

"It looks like somebody enjoys having something in their ass." I said as I slowly began stroking it. I was enjoying every second of this as we both watch me work his pretty cock -- me in control and him helplessly. It didn't take long before I could feel his cock begin to tighten, so I quickly leaned onto my back and pulled him onto me. I pulled my panties from his mouth and resumed stroking his cock. I wanted him to spray it all over himself as an added humiliation. With just a few more strokes, he unleashed stream after stream of warm cum as his moans matched each stream. He was covered in his own cum and I could feel his breathing still heavy as I slowly lowered him back to a sitting position.

"Didn't expect that, did you Dani?" I asked victoriously.

He sat cum covered with no bottom and his hands bound. I would definitely have to get a pic from the video of that to add to what would be my new trophy case.

Even with the match over, I didn't feel a pressing urge to untie him. I actually kind of liked having him helpless like this and I didn't want him changing his mind about the loser's penalty either, so I walked over to the table and grabbed the marker.

"This will be a nice reminder of whose bitch you are now Dani." I said as I rolled him onto his stomach again.

"This is so humiliating." he said helplessly as I straddled his legs and looked down onto his exposed ass. In large letters, I wrote Dani's Bitch -- one word on each check and took a moment to admire my handy work.

"The words certainly tell a nice story, but let's be sure you have a good idea of what that means." I said to him as I stood up.

Lifting him up to his knees, I walked around in front of him and pulled his mouth down onto my cock. He didn't protest as he hungrily accepted it and began working me like a pro. There's no way he hasn't done this before I thought to myself as I quickly began getting lost in the sensation. He was working the full length of my 6" cock making full use of his tongue and sucking so hard it was better than any pussy I had ever had. Wanting to save my cum for his sexy ass, I had to step back and catch my breath and he seemed to look at me as if he still had power over me.

"How did that feel Dani?" he asked wickedly. "I bet that was the best head you've ever had."

Not wanting to give him the satisfaction, I simply collected myself and helped him to his feet.

"I think it's time to untie you now." I said as I freed his hands.

"Are you sure you don't want to ride my big cock instead?" he mocked. "I know deep down you really want me back inside you again and it will be such a shame to have your smaller cock try to do what mine was more than capable of."

"Not this time slut." I replied giving him a quick smack on his freshly labeled ass. "It's your turn to be the bitch and you've got the markings to match. I'm going to make you sissygasm like the bitch you are and all the gurls will enjoy watching the replay."

Guiding him down onto all fours, I applied some lube to his ass and my cock and with him already having had my finger in him, began to work my cock into his ass. I could hear him moan slightly as my head disappeared into his ass pussy, but to this credit, he remained tight and didn't allow me to loosen him up very quickly. I don't know how he was so tight, but it was the best piece of ass I'd ever had I though as I grabbed his waist and watched his cheeks jiggle with every thrust of my hips. The sensation was amazing and while he was gasping in rhythm and letting out some moans, I did not think he was anywhere close to sissygasm as I was to cumming.

He must have sensed the same and, pulling off of me, he quickly turned around pushed me down and re-mounted my cock in cowgirl position. I was speechless, but didn't resist as I so desperately wanted to get my cock back into his ass. Before I knew it, he was riding me like a pro -- gyrating his hips and bouncing up and down on my cock. Just like when he was giving me head, I felt he was somehow in control and I could only lie there helplessly as he rode me hard. If the feeling of his ass wasn't enough, the view of his massive 8" cock bouncing in front of me made me think there wasn't anything about him that was better than me.

"Cum for me baby" he said. "My ass is going to milk every drop off cum out of you and be the best fuck you've ever had."

I was in no position to argue and grabbed onto his ass as I felt that familiar sensation growing in me.

"Oh fuck, I'm going to cum!" I shouted as he continued to ride me. I pulled him down onto me and thrust upward with wave after wave of the best orgasm I'd ever had in my life. I could have sworn I saw nothing but stars for the next 10-15 seconds as my body spasmed uncontrollably.

He slowly slid off of my cock as I regained my senses. As he walked away, I enjoyed the irony of the markings on his ass. In theory I had just recorded my first win and he was my bitch, but as I watched his sexy ass walk away, he left with both of us realizing that deep down, there was only one bitch in the room...and it wasn't him.
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