Leo Vs Katherine: Earning Another Shot

By MaskedBunny

I should probably mention that this story is pretty explicit with sexual themes between a male and female.  Thus, if this bothers you, I would recommend looking at one of the other AMAZING writers on this site.  If not, then continue on and let me know what you think

Leo felt the warm itchy feeling build up in his dick as he opened the door and began walking down the familiar staircase. About a week ago, he had been down the same stairway to wrestle one of the most gorgeous women he knew before fucking her. Afterwards she had requested a rematch, which Leo hoped was now.
Pulling out his phone again, he smiled and reread the text. ‘Cum over ;)’
It was only two words long, but it had set his heart racing anyway. Immediately, he had pulled on a pair of boxer briefs, a pair of jeans, and a t-shirt before heading over to her house.
Reaching the bottom of the stairs, he stepped through a doorway to his left into the same room from last time to see Katherine standing on the mat, already stripped down to a small sexy thong bikini. However, instead of the black one she wore last time, it was white with little red medical crosses on the triangles covering her breasts.
Smiling, Leo began unbuckling his belt when he noticed another woman standing next to her and froze. Standing two inches shorter than Katherine, she was just as beautiful with ear length brunette hair that was spiked backwards. The woman was slim with a 36C bust size and an amazing ass. She wore a metallic baby blue bikini top with white trim and a matching thong that seemed perfect for her.
Noticing Leo’s eyes looking her over, the woman smiled.
‘I don’t understand,’ Leo said confused.
Smiling, Katherine walked across the mat and wrapped her arms loosely around his waist, ‘You beat me fair and square last time, right?’
Leo nodded uncertainly.
‘Well, I told Brittany here about our little match and she wants a piece of you, too. And since I lost, I figure I should have to earn a rematch. So we were talking and think we should rassle to see who gets to take you on first.’
‘Oh trust me; you earn it just by looking like that.’
Katherine grabbed his dick through his jeans, ‘Don’t worry cutie, the stakes are the same as last time where the winner gets to fuck the loser. And you get to join in, so I hope you can handle us both. But until then, why don’t you strip down and go take a seat over there?’
Obediently, Leo walked to a chair sitting at the side of the mat and stripped down to a pair of gray boxers. Turning his attention back to the mat, his dick began pulsing with excitement.
A few feet away from him, Brittany was straddling Katherine’s lap and squirting oil all over her tits. When she was satisfied with the amount, she slowly began rubbing it in, causing Katherine’s nipples to grow hard.
Brittany then slid herself backwards down Katherine’s legs and squirted some more oil on the front of Katherine’s thong. As soon as her hands began massaging it around, Leo watched Katherine’s body arch a bit while a few moans escaped her mouth.
‘You like that bitch?’ Brittany asked with a giggle.
Katherine moaned in reply.
Smiling, Brittany got off Katherine and watched her roll onto her stomach. Looking at Leo, Brittany winked and climbed on Katherine’s perfect ass. Squirting a generous amount of oil onto it, Brittany slowly started bucking her hips back and forth like she was humping her.
‘This is what I’m going to do to you when I’m done,’ Brittany said while she played with Katherine’s thong strap.
‘Yeah, because after I fuck you, I’ll want you to make me happy,’ Katherine replied.
Smacking Katherine’s ass, Brittany got off of her and lay on her back with both arms extended to the side, ‘Your turn bitch.’
Smiling, Katherine pushed herself to her knees and took the bottle of oil. She then began squirting it all over Brittany’s body and rubbing it in every inch. When she reached Brittany’s thong, Katherine returned the favor of rubbing it in sensuously, causing Brittany to begin squirming with excitement.
‘Who likes it now?’
‘I’ll like it even more when I’m fucking you silly later on,’ Brittany moaned softly.
‘Oh really?’
Tossing the oil aside, Katherine suddenly slid her hand inside Brittany’s thong and began fingering her, causing her eyes to open up.
‘No…fair bitch!’ Brittany groaned.
‘All’s fair,’ Katherine replied with a smile.
Angrily, Brittany placed both feet against Katherine’s thighs and pushed, sliding a few feet away. She then rolled over and got to her knees.
Leo watched as the two of them stared silently at each other for a few minutes before diving forward. Meeting in the center, they wrapped their arms around each other in mutual headlocks and began straining to take the other down.
‘All’s fair, huh bitch?’ Brittany asked.
She quickly snaked her left hand under Katherine’s top and began squeezing her left tit catching her of guard. Immediately, Katherine pulled away, releasing her headlock. Seeing this as her opportunity, Brittany pushed her over.
Pressing Katherine’s hands against the mat, Brittany smiled and straddled her waist, ‘Ready to give in and let me fuck you yet?’
‘Not until I make you squirm like a little slut,’ Katherine replied.
Without saying anything else, Brittany slid her body up the slippery body beneath her until she was perched on Katherine’s shoulders. Flashing a quick smile at Leo, Brittany leaned her hips forward, pressing her crotch into Katherine’s face and began shaking her ass back and forth.
‘Hope you like it down there.’
However, the only reply came in the form of muffled groans from beneath Brittany’s pussy.
‘Can’t hear you too well. Did you just say you want me to grab your titties? Well, don’t mind if I do then.’
Reaching behind her, Brittany pulled Katherine’s top up, revealing a pair of perky round tits. Then, with great satisfaction, she began squeezing them both with her hands, causing Katherine to begin kicking the mat and screaming with pain. Smiling, Brittany relaxed her grip for a few seconds, before squeezing them again when Katherine calmed down.
Leo watched intently as Brittany repeated the cycle a few more times, his dick growing harder with each squeeze. Something about listening to Katherine groaning with pain was a turn on.
Despite having just met the new girl, Leo was really taking a liking to her. She seemed to know what she was doing. Not too mention that she was extremely hot while dominating Katherine. He was really looking forward to fucking her.
Giving them one last squeeze, Brittany eased her crotch off of Katherine’s face and looked down at her, ‘Give up yet?’
‘No thanks,’ Katherine panted.
With a sudden burst of energy, she bucked her shoulders up, sending Brittany toppling off of her. Katherine then rolled over and dove after her, straddling her back. Acting quickly, Katherine grabbed Brittany under the chin with both hands and leaned back.
‘Not so smug now, are you bitch?’ Katherine cooed over Brittany’s groans of pain.
Releasing her grip, she shoved Brittany forward onto the mat, untied her top, and pulled it off of her. Holding it firmly in both hands, Katherine wrapped it around Brittany’s neck and tugged on it hard enough to choke her without danger.
‘Knock it off you crazy bitch!’ Brittany yelled, frantically pulling at the top.
Laughing, Katherine released her grip, pulled her own top off revealing her amazing firm breasts, and tossed it aside. With a devilish smile, she slid her arms under Brittany’s, placing both hands on her tits. Pulling Brittany back again, Katherine squeezed hard.
‘Give up?’ Katherine asked.
‘No!’
‘Are you sure?’
‘Yes!’
‘Good, because I’m having fun.’
In one fluid motion, Katherine let go of her opponent and rolled her over. Moving to Brittany’s legs, she slowly lifted her Brittany’s leg up into the air and placed her own left on the other side of Brittany’s right so they were crotch to crotch.
‘What are you doing?’ Brittany asked softly.
Wordlessly, Katherine flashed a smile at Leo that almost caused him to orgasm on sight and began pounding her pussy into Brittany’s like a jackhammer.
At first, Brittany seemed to be caught off guard by the change in tactic, but after a few seconds her body began responding in kind.
Moans of pleasure filled the basement while their hands began exploring each other’s bodies, leaving Leo to wonder how this was going to end. However, after a few seconds, Katherine unexpectedly reached out and tweaked one of Brittany’s nipples, eliciting a squeal.
‘Give up?’ Katherine panted.
Brittany nodded eagerly.
Silently, Katherine stopped slamming her crotch against Brittany’s and pushed her back onto the mat. In an instant she had her oil soaked thong off, tossing it to Leo, ‘In a second big boy, I promise.’
Leaning forward on all fours, Katherine placed her tongue right above Brittany’s pussy and slowly worked her way up. When she reached Brittany’s tits, Katherine hungrily began sucking her tits.
‘Do you like this?’ Katherine panted while she worked.
‘Yes,’ Brittany moaned.
‘Do you want more?’ Katherine asked.
‘Yeeeeeees.’
Smiling, Katherine gave Brittany a deep kiss on the lips before sitting up and placing her pussy over Brittany’s face. Motioning for Leo to join, Katherine gently began sliding her hips back and forth into Brittany’s tongue.
Anxiously Leo leapt off the chair, kicked off his boxer briefs, and made his way over to them. Kneeling at Brittany’s legs, he pulled her thong off and tossed it aside. Responsively, she arched her hips slightly into the air and spread her legs for him.
As he slid his throbbing dick inside her, she shuttered.
Then, mimicking Katherine’s intensity, he began pumping his hips rapidly. He could hear her moaning beneath Katherine’s body.
‘So when…do you…want…to have…our…our…our rematch!’ Katherine asked while her body shuttered with orgasm.
Leo watched her climb off Brittany and lay down, smiling.
‘Next week?’ Leo asked, his loins burning.
‘Definitely.’
‘Iiiiiii wanna watch,’ Brittany said as her body shook with an orgasm too, ‘And I want another match.’
‘I think that could be arranged,’ Katherine replied, ‘I know some other women who want in on this.’
Exploding, Leo collapsed between the two of them, ‘I’m game.’
Softly patting Leo’s dick, Katherine smiled, ‘good.’