Lilly was one of the most athletic people Jack knew. He loved sex with her and was always willing to try something new with her. When she told him about an underground female wrestling ring he was intrigued. The five hundred dollar entry fee concerned him at first. She told him about the stakes of how each of the women would have a male backer. Whichever woman lost was the sex slave of the other backer for twenty minutes. He didn't like the idea of Lilly being taken by someone else, but she was a good wrestler and felt she could win. The idea of her winning another woman for him really turned them both on so they decided it was worth the risk. The winner also got their entry fee back and five percent of the gate for the match. So, they could make some money too.
Lilly trained hard for the month until the match was scheduled. They abstained for a week before the match. Lilly told Jack that she wanted to keep her stamina up and that when he got his reward for her win he would be able to cover the bimbo she beat.
There was a bigger crowd than Jack expected when they got to the ring. Lilly was in the second of five matches. They went together to the locker room. Lilly getting ready for her match stretching and warming up. Then she changed into the bikini she would be wrestling in. Jack was half watching the match. He was confident that Lilly could have beat either of the girls.
Then it was time for Lilly's match. Jack went out to the ring with Lilly. He was going to work the corner for her. Jack listened as the referee went through the rules.
"This will be a three-round match between Angie the Annihilator and newcomer Lilly. Each round will be three minutes. The loser will service the winner's stud for twenty minutes while we all watch. The winner will be determined by the wrestler who has the most points at the end of the three rounds. Points will be awarded for successful wrestling moves as well as stripping the other wrestler of clothing. Points can also be earned while controlling the opponent by pleasuring or humiliating your opponent. If one of the wrestlers cums during the match they immediately lose. In the case of a loss this way any time left in the match is added to the time the loser must perform services. If a wrestler hasn't lost their top at the end of the first round they will take it off before the beginning the second round. Likewise, if not already naked at the end of the second round a wrestler will strip naked before the beginning of the third round. Are there any questions?" Both girls shook their heads. "Then let's wrestle." He dropped his hand signaling the beginning of the match.
Lilly was excited and nervous as she moved toward the other girl. They grabbed each other arms and twisted trying to get an advantage. Lilly was able to sweep Angie's legs and land on top of her. Angie struggled as Lilly pulled Angie's arm into a lock. Wrapping her legs around Angie's waist Lilly started applying pressure. Angie quickly tapped out. The ref blew his whistle.
Angie's stud, Paul watched shaking his head slightly. He thought Angie would have been able to get out of the hold. This newcomer didn't seem that tough, but maybe Angie was baiting her trying to make her overconfident.
"Angie down and Lilly takes the dominate position." As they took their positions Lilly glanced at the scoreboard and saw she was up four to nothing. With another whistle the ref said, "Wrestle."
Angie quickly reversed their positions flipping Lilly onto her back and sat on her hips. Reaching down she caressed Lilly's breasts rather than going for a wrestling hold or pin. Lilly suddenly realized that the wrestling match was more focused on the sexual side then she thought. Angie's palms rubbed Lilly's nipples through the fabric of her bikini and Lilly felt them getting hard. How she loved having her breasts played with, but she had to get Angie to stop before she got too aroused. Lilly rolled her hips and grabbed Angie's wrists. Angie used the leverage being on top to pin Lilly's arms to the floor and leaned over her. She whispered into Lilly's ear, "You enjoyed that didn't you. Just submit and I will make sure you enjoy the rest of the match and your services afterwards."
Paul nodded yes it looked like Angie was going to dominate the new girl like he had expected. Was it his imagination or was she breathing hard already?
Lilly bucked her hips and lifted her legs hooking Angie's left shoulder with her right leg. In seconds she had Angie off her and reached down pulling off Angie's bikini top. The large areola on her small tits looked so inviting. Lilly swung around so she was laying on top of Angie chest to chest. She pinned her arms down then locked her legs into Angie's, so she was at Lilly's mercy. Lilly kissed Angie's neck and then down her breast until she was sucking on her left nipple. Angie wiggled and squirmed but couldn't get free. Lilly felt the nipple getting harder between her lips as she licked and sucked on it. Then a low moan escaped Angie's lips.
Lilly finished removing Angie's bikini top and asked, "Who is enjoying it now?"
Angie bucked Lilly free and she rolled away to make sure their positions wouldn't just reverse again. The roar of the crowd filled the air as Lilly tossed the removed top aside. The two women on their knees faced each other hand sparing trying to get an advantage. Angie lunged at Lilly and Lilly ducked slightly moving to hook a leg as she grabbed Angie around the shoulder. With a twist of her hips Lilly put Angie on her back. Lilly's left knee pinning Angie's left arm. Lilly reached back and pulled aside Angie's bikini bottom. Angie's pussy was shaved smooth. Lilly dropped her hand on top of it and started rubbing Angie's slit. Using her weight and leverage Lilly stretched Angie out taking away her ability to struggle free.
Lilly's fingers started getting wet with Angie's juices. Then she slid two fingers into Angie's pussy. Just as she started sliding them in and out the buzzer announced the end of the first round. People in the crowd shouted their approval and encouragement to both girls.
Lilly walked back over to her corner and Jack gave her some water. He said, "You are doing well sweetie. I knew you could do this."
Taking a drink, she thanked him. As she caught her breath the ref came over and said, "Your top please."
Lilly looked at the ref confused for a second and then remembered that she had to start the second round without her top. She untied the top and handed it over. One man yelled, "Nice tits beautiful." Lilly looked at the scoreboard and saw that she was ahead by fifty points so far.
Lilly took another sip quickly as the ref told them it was time for the second round. Jack gave her a thumbs up as he took the water bottle. Lilly watched Angie's tits sway as she advanced. They weren't huge, but they made Lilly's small pert tits seem tiny by comparison. With a sudden rush Angie tried to bull Lilly over. Lilly ducked her shoulder and flipped Angie over her. The crowd yelled its approval. As Angie landed the air puffed out of her lungs and Lilly rolled on top of her. A knee on each shoulder she ground her crotch into Angie's face.
Angie tried to catch her breath, but Lilly on top of her was making it difficult. Angie kicked up her legs trying to get a leg around Lilly's neck. Lilly pushed the leg aside and hooked an arm behind her knee. With a couple of quick tugs the bikini bottoms fell to the ground. Lilly started rubbing Angie's pussy again which was already wet with her juices. As Lilly rubbed Angie got wetter until she slipped a finger in the wet pussy and started sliding it in and out.
Angie started bucking her hips and flopping side to side underneath Lilly trying to throw her off. Lilly pulled Angie's leg back to her hip to help keep her under control. Her fingers middle two fingers sliding all the way in and out of Angie's pussy. Angie's moan vibrated Lilly's pussy through her bikini and the pleasure broke her concentration for a second. Angie was able to buck her off finally.
Jack watched Angie's breasts sway as she rolled free of Lilly. On her knees she sucked in deep breathes and her boobs slowly rose and fell. Jack had gotten hard as Lilly came close to making Angie cum. He thought about how good it would feel to slide deep into her soaking wet pussy and pound her. Her boobs would sway with each stroke.
Angie lunged at Lilly to try and catch her off guard. Lilly pushed her to the side and hooked Angie's left arm in a half nelson hold as Lilly moved behind Angie. Lilly quickly wrapped her legs around Angie and started bending her backwards. Angie squirmed trying to get free, but Lilly arched her back taking away all of Angie's leverage. With her free hand Lilly started messaging Angie's tits. First one then the other. Each time she started Angie used her free hand to bat it away. Then sliding her feet down Lilly hooked Angie's legs and spread them apart. Angie grabbed Lilly's wrist as Lilly tried to start stroking her again. Lilly licked Angie's ear and sucked gently on the lobe.
Angie moaned softly and could feel her resolve weakening. Lilly had her back stretched out and turned on. Letting go of Lilly's free hand Angie tapped the matt signaling her surrender in the current position. She knew at this point the only chance she had to win was to make Lilly cum.
Paul gave her the water bottle. "You are in a hole honey. She looks sweet and I would really like to teach her what a real man feels like. Make her cum for me."
The ref separated the two wrestlers and faced them to each other on their knees. As they grasped each other Angie was determined not to let Lilly get behind her again and was surprised when Lilly instead pushed her straight back. When Lilly straddled her chest with a knee on each arm Angie knew she was in trouble. She tried to kick a leg up for leverage she found it pinned against Lilly's body instead. Lilly's fingers quickly found Angie's wet pussy and started fingering her again. Angie bucked trying to minimize the stimulation and was starting to pant as the whistle signaled the end of the second round.
Jack gave Lilly the water bottle as Lilly took off her bikini bottoms. He said, "The only way you lose now is if she makes you cum. Just keep her wrapped up and you will win."
"No, I want to make her cum. I almost had her twice last round. I will get her this round."
The whistle signaled it was time to start the third round. Angie and Lilly faced each other, and Angie said, "You have a nice pussy. I can't wait to slide my finger into it."
Lilly said, "My fingers feel so good in your wet pussy. After you cum I will let you lick them clean."
The ref signaled them to start and Angie attacked trying to push Lilly back. Lilly used her momentum to turn her slightly and pushed her to the ground. With a quick move she had her legs around Angie's torso pinning both her arms to her sides. Lilly hooked her ankles locking the leg hold, and then reached down pulling Angie's legs apart. Lilly slide two fingers into Angie and started sliding them in and out. Angie struggled, but with each stroke they became weaker. Soon Angie was moaning and only her hips were moving. No longer to escape but trying to push against Lilly's fingers.
Lilly's thumb started rubbing Angie's clit and this drove her over as she came shaking with pleasure.
The ref tapped Jack on the shoulder and said, "She came. Take your prize."
Jack stripped and walked over watching Angie writhe with pleasure. The women in the crowd catcalled seeing Jack's size. He knelt between Angie's legs and pulled Lilly's fingers out. With a long stroke he buried his cock all the way into Angie. Lilly let go and got up as Jack started sliding in and out of Angie. Lilly stood there for a minute watching Jack lean over Angie and match his stroke to the claps of the crowd. Angie's tits swayed back and forth as she moaned and thrust up to meet Jack. Then Lilly knelt down and put her fingers into Angie's mouth. "Lick them clean."
Angie started licking then sucking on Lilly's fingers and then felt Jacks fingers on her clit as he continued pounding her with his large cock. With a muffled scream she came again shuttering. The crowd roared its approval.
Jack pulled out and told Angie to get on her knees. Jack got behind her and pushed into her from behind. He reached around and cupped her breasts. As he started going in and out he played with her nipples. In a minute she came again, and her legs gave out as she collapsed on her stomach. Jack kept going laying on her back grinding into her. Angie's hips started jerking as she came yet again. The crowd chanting make her cum. Jack slides a hand under Angie and starts rubbing her clit as he picks up the pace his cock as hard as a rock. His fingers were soaking wet with Angie's cum and he leaned over her saying, "You are such a slut. You are so turned on by being fucked hard by me in front of all these people. The only thing that would make it better for you is if they got to do you too."
As Angie started cumming again she moaned, "Yes. Oh God yes." Her pussy contracting on his cock drove him over the edge. Jack thrust deep one last time and then pumped Angie full of cum.
As Jack went soft he pulled out and stood up. His cum started leaking out of Angie. She just moaned as she rolled over and felt it running down her leg. Paul helped her to her feet as the cum continued running down her leg. He whispered, "You threw the match."
With a nod Angie said, "I could have tried harder, but she is a good wrestler. She got her thumb rubbing my clit and I couldn't stop the wave. She will be back and you will get your chance to fuck her."