"Better Than Broadway" with Madison Iseman and Olivia Holt

[MiamiLyfe]

Better Than Broadway
Starring Madison Iseman and Olivia Holt
Codes: MF, MFF, Oral, Creampie
Written by MiamiLyfe
Disclaimer: The following is completely fictional and it is nothing but pure fantasy

"Oh god! Oh yes! Keep going!" Madison Iseman moaned.

"Almost there," Jack told Madison as he repeatedly impaled the blonde actress with his cock.

"Little bit longer…almost there," she said between breaths. "Do it…at the same time."

The two of them were both naked and having sex in the New York bedroom. Jack had his arms on either side of Madison as he was on top of her doing her in the missionary position. She had one of her legs wrapped around him and as her third orgasm of the afternoon approached, she reached up and grabbed onto his biceps.

"Now, Jack. Now! AAHHHHHH!," She let out a loud moan as she came, and watching her o-face and feeling her already incredibly tight pussy clamp on his cock drove him to fill the concom he was wearing with his second load with her that day. After he finished cumming, he lowered himself to kiss her before rolling off of her. She let out a pleasurable sigh, and then said, "I love vacation sex."

"You happy to be out of LA for a bit, or are you happy to be on vacation from your boyfriend?"

"Watch it," she said giving him a playful slap. She didn't like him talking about her boyfriend, especially not while they were both naked together. Jack and her boyfriend had never warmed up to one another. Jack wasn't sure what the deal was between Madison and her boyfriend ​​Spencer Sutherland. They had been dating for several years, but that didn't stop her from hooking up with some other people from time to time, Jack being one of those lucky guys.

"Sorry," he apologized.

"I need to take a shower," she said, getting up from the bed and walking naked to the bathroom.

"Want some help?" he asked as he followed her.

"No, we need to get ready," she told him.

"We have time," he said as he plopped the used condom into the trash bin.

"Not really, and we both know what will happen if we get in the shower together."

"I'm not sure if you can, but I can control myself," He said in a confident butt joking tone. She did not give an audible answer, she rolled her eyes at him and then looked down. She gave his cock a little bit of a slap and his erection simply bobbed up and down for a moment.

"Alright, fair point," he conceded, "but you know what we could be doing is better than seeing anything on Broadway."

"Yeah, sure," she laughed. "Look, I promised Liv I'd take Roger for a walk before leaving, so you can go do that while I shower. This way I don't need to worry about you sneaking in with me."

"So you're kicking me out?"

"Temporarily," she answered and lightly pushed him back until he was outside the bathroom. Jack didn't put up a fight and just redressed. He then went to take Roger for a walk. Roger was Olivia Holt's dog. The room he was just having sex with was the guest bedroom of Olivia's New York City apartment that she was renting while she was performing Chicago on Broadway. Madison was staying with her while she was visiting. Jack too was visiting New York, but he was there for work and was staying at a hotel room that his employer was paying for. He was happy that his trip lined up with Olivia performing so he could see his friend perform on stage. It was Jacck talking on the phone with Madison about how glad he'd get to see her, that spurred Madison to take the trip when she did. She figured that they could go together to support their friend.

Though it appears as though Madison might have had some other ideas for the trip as well. The two went to lunch together, and then she invited him back to Oliva's place to hang out before the show. And from there, things quickly progressed into them having two rounds of sex on the guest bed.

After about thirty minutes, Jack took Roger back to the apartment and gave him a treat for doing his business. As Madison got dressed, he took a quick shower to wash the sex stank off himself. Once they were both dressed, they got a quick bite to eat since they were planning on having a very late dinner with Olivia after the show.

Olivia had left them tickets at Will Call, and they were in their seats at the Ambassador Theater with five minutes to spare before the curtain opened. Both had seen the play Chicago before, as well as the Catherine Zeta-Jones film adaptation, but it was different seeing their friend play one of the leads. Oliva was great on stage, though Jack could not help but notice how good Oliva looked. Dressed in black with her legs exposed in black tights. He was still a little turned on from being with Madison that afternoon and watching Olivia was not subduing those feelings. And Maison notices. She saw how locked on the stage he was, and it was after the intermission that she thought she noticed a lump in his pants. Carefully so no one around them would notice, and nor would Jack stop her, Madison slowly moved her hand until it was just over the lump. She then lowered her hand on top. He jumped but did not make a sound when he felt her on his inner thigh. She then pressed her hand down and squeezed it. She then removed her hand as she tried to stifle a giggle as she had confirmed that Jack was hard in his pants. Jack was embarrassed, but she let him be for the remainder of the play. It was not until they left the theater and were outside waiting for Olivia.

"I can't believe you had an erection," she laughed.

"Quiet," he tried to hush her.

"Was that just from watching Liv, or were you thinking about something else?"

"Hoping I was thinking about this afternoon?" he quipped while waving at Olivia as she came out the door. She waved back but had to sign some fan autographs and take selfies before she could go with them.

"Want me to stand in front of you? Hide any boners you might get."

"Is that the reason you want to stand in front of me? In case I get an erection, I'll have someplace to hide it." Her teasing him had somehow morphed into some high-level flirting. As Olivia got closer, bringing more people closer to them, they quit talking. Though even when they went to go have dinner with Olivia, Madison dropped a number of euphemisms and double-entendres during their meal. She told Liv she had Jack's "full attention" during the play, and then asked him if he found any parts of the play "especially hard" to follow. Jack was not entertained by this, but he did his best not to show it and have Olivia catch on.

After they ate they all went back to Olivia's apartment. Olivia went right to her room to change into sweatpants and a t-shirt, and then she took Roger outside for a quick walk. Jack thought it was time for him to leave, but Olivia told him to stay and they could hang out for a bit when she got back. Once she was out of the apartment, Jack turned to Madison and snapped at her, "What the hell was all that?"

"All what?" she played coy,

"All that stuff at dinner. All the erection inuendos."

"I don't know what you're talking about."

Jack paused and thought a moment. "You know, I thought you were just making fun of me, but now I'm thinking that you're jealous that I might have gotten hard looking at Olivia."

"There was no might about it," she snidely replied.

"See I knew it."

"Look, Jack, I'm sorry you had a HARD time at dinner, but you're crazy if you think I was jealous of anything."

"I'll show you a hard time," Jack snapped back and lowered the fly on his jeans. Madison excitedly bit her lip as she saw him reaching into his pants.

When Olivia got back to her apartment, heard some strange sounds and noticed that neither of her friends were anywhere in sight. She took off Roger's leash and gave him a treat before she went to investigate. She followed the sound to the hallway and before she rounded the corner she heard a loud moan from a woman. Turning the corner, she found her friends in the hall.

"What's going on here!" Olivia exclaimed. "I can't believe you two." Of course, it was extremely obvious what was happening. Madison was braced against the wall in the hallway with her pants down just above her knees, and Jack was right behind her with his pants below his ass, and his cock pumping in and out of Madison.

"Oh God, Olivia, this isn't…ummm…" Madison tried to think of something to say.

"This is exactly what it looks like," Jack said and then withdrew his cock. Exposing his condom-wrapped hard dick to Olivia, with it glistening in the hallway light from the American Horror Stories actress's pussy juices.

"Wow, she was pretty wet, huh?" Olivia said as she looked at his cock and took a few steps forward.

"Yeah, she is," he agreed.

"Let me ask, are you hard because of her, or because you are still thinking about me on stage?" Liv asked, and Madison laughed. Jack's head quickly snapped and looked at Madison.

"You told her? When?" He wanted to know.

"I texted her about it as soon as the show was over."

"So the whole time you were making subtle jokes during dinner?" he asked Madison.

"I knew what she was doing," Olivia answered. When Jack looked back towards Olivia he realized that she moved even closer. "Don't worry, I found it flattering."

Olivia then took hold of his hard dick. "Maybe we should take this to the bedroom," she suggested. The three of them quickly moved into the guest room. Olivia had Jack sit on the edge of the bed and she dropped down to her knees. She yanked off the condom and began sucking his cock. While Holt hungrily sicked his dick, Iseman stood nearby and began stripping out of her clothes. Once naked she got onto the bed with Jack. She and Jack began kissing, and he reached out and began fingering the actress's mostly waxed snatch, except for a narrow landing strip. She moaned into his mouth when she felt him slide a second finger into her. Madison eventually reached down for his cock that Olivia was still sucking on. Iseman's hand replaced Holt's on his shaft and she began stroking him while Olivia's lips and tongue focused on the tip. Eventually, it was all too much for Jack. He could no longer even concentrate on trying to kiss Maison, he was just lost in the feeling of pleasure he was getting on his dick.

"So how is she?" Madison asked.

"Soooo good," Jack moaned.

"Is she better at it than me?"

"No chance I am answering that," he said smartly.

"And you really don't want to play that game," Oliviia teased her friend, before going back to giving a blow job.

"Well, you do look good with a dick in your mouth," Madison teased her back. Olivia responded by flipping her off.

"She is right, you do," he told her honestly. "Liv, I'm going to…"

"Then do it already," she told him. Like with Madison, Jack and Olivia had hooked up dozens of times over the years. Also just like Madison, Olivia was currently dating a guy that Jack didn't like. While Jack never got along well with Madison's boyfriend, it was Olivia's that he really didn't much care for. He could not understand how they ever got together or why they are still together. However, unlike Madison, Liv was in a defined open relationship so Jack never felt the slightest bit of guilt when they hooked up, only pleasure. And that pleasure almost always included him finishing at least one load in her mouth, and today was no different. So when she told him to do it, he blasted the back of her throat with as much cum as he could fire.

Normally he could feel her swallowing as he came into her mouth, this time he could not. He found out the reason for that after he finished cumming. Olivia dragged her lips off his cock with a pop and then opened her lips to show him all the jizz she'd collected in her mouth. Olivia then got up off the floor and moved to Madison. She grabbed her friend by the back of her head and pulled her in for a kiss. Jack watched as the two blondes kissed, and saw Liv push some of his cum from her mouth to Madison's, with some trickling down the side of each of their lips as they kissed and snowballed his cum.

Even after they had swallowed all the cum, continued to kiss. Olivia was the aggressor, even to the point that Madison fell backward. Olivia did not let her get away and crawled onto the bed, so her knees were right on the edge with her feet hanging off of it, and her hand propped her up as she leaned over her friend before bending back down to kiss her some more. Jack, just like any other guy in his position, could not help but get aroused by the sight next to him. If his dick deflated at all after the blow job, it was now back to full mass. He took off his shirt and kicked off his pants and boxers, which had pooled around his ankles while Olivia sucked him off.

With Jack now nude, there was only one person in the room who still had their clothes on. Olivia except for having no shoes, was still dressed as she was when she took her dog out for a walk. That did not last long. Jack got off the bed and yanked down Olivia's sweatpants. She had a pair of white panties that were soaking. He could clearly see how wet they were, and when he removed them he could feel the added weight from how wet they were. He put his hands on her ass and bent down. Her completely hairless pussy was literally dripping wet, and he ran his tongue along her slit, licking up all her excess juices. Liv sat up and moaned as she felt his tongue. She then turned around to face Jack when she felt his tongue pull away.

"Don't tease me," she pleaded.

"Trust me, I'm not," he told her and then slid his dick inside of her. She was so wet that despite being crazy tight, he had no issue sliding his dick into her. Olivia moaned and smiled back at Jack as he entered her.

"God I missed this," he told her. "You feel so good, so tight."

"Damn right," she said with pride about how tight she was. "Ummm, I've missed this too," Olvia told him as he slowly began working his dick in and out of her.

As he built up speed she got more and more excited. Despite Olivia laying on top of her, Madison was feeling left out of the action. She reached up and gave Oliva's hard dark reddish nipples a tweak. Liv let out a bit of a yelp when she felt her nipples suddenly being played with.

"Oh, oh, wow, already, ugghhh," Olivia moaned. It'd only been a few minutes, but Olivia was so aroused even before Jack had his cock in her that it did not take much for her to get to the point of near orgasm. She let out a grunt and then her pussy gushed as she came. Dripping down onto the bed she soaked the bedsheets beneath her. Jack pulled out of her and Olivia rolled over onto her back. "That was a good one," she said with a smile and light laugh.

"Sure seemed," Jack said with some pride.

"You know, I was on the verge of something close to that before you interrupted us earlier," Maison said, reminding the other two that she two was still on the bed.

"I can help you out with that," Jack replied.

"You, better," she told him. She had him lie down on the bed and was quick to get on top of him. She was quick to sink down on his dick and began riding him. While she was on top of him, Oliivia slid next to him.

"Doesn't she have the cutest nipples," Olivia whispered to Jack as she watched her friend methodically grind on her snatch on top of him.

"Yeah, she does," he agreed, as he reached up and cupped her tit and ran his thumb back and forth over her small dark nipple. She moaned as she felt her tits being played with. Jack let out his own groan as Olivia began kissing the side of his neck. Having one actress ride him while the other one kissed and rubbed his chest was getting Jack excited. He then took hold of Iseman's hips and began thrusting his cock up into her. Madison's moans were getting louder as he fucked her hard and fast. After a few minutes, he flipped her over. Once again Madison was on her back with Jack between her legs. She raised her legs and spread them wide as he pushed back into her. Just like the afternoon, Jack and Madison were doing it missionary. However this time, Olivia was right there with them.

After stripping off her shirt and removing her pants completely, Holt went back and forth kissing both of them. Now with Madison on her back, Holt's hands roamed over her friend's chest, playing with her tits. Looking over at Liv, Jack could not help himself from reaching over and pushing two fingers into her tight box. He fingered her for a minute before pulling his fingers out and sucking them clean. Jack remembers the first time he ever went down on Liv, and he couldn't believe how good she tasted and still tastes just as good now as she did then. He then pushed his fingers right back into her, which caused Holt to moan right into Madisoon's mouth as they made out.

After several more minutes, Madison got the orgasm she desired, but Jack still continued to pound her pussy. He thought for a minute, about pulling out and driving back into Olivia, but she whispered something in his ear that made him change his mind.

"Are you close," Olivia asked between neck kisses she was giving Jack.

"Kind of," he grunted.

Olivia then moved right up beside his ear, "Cum in her," she whispered. She then pulled away and Jack looked towards her, and she gave him a devilish smile. Unlike Olivia, Madison almost always made Jack use a condom when they hooked up. He was so lost in the moment that when he switched from Olivia to Madiisoon that he never even thought about a condom. Now that he did notice it, he was becoming even more aware with every second of how her pussy felt around his cock. He started moving his hips even faster after that.

"Oh god! Yeah!" Madison called out in response to him taking things up a notch.

"That's it, Jack," Olivia encouraged. "Fuck her good, and fill her."

"Fill me?" Madison asked."Wait, condom. You don't have a condom on, do you?"

"No," He informed her.

"Shit," she said.

"Just let it happen. You know you want it," Olivia advised Madison. She thought for a moment, as Jack continued to rail her.

"Fuck it, fine. Why not?" she gave in.

"Slut," Olivia giggled at her.

Jack's response was to grab Maison's legs from out on the side and move her legs up over the blonde actress's head. He drilled the Clouds actress as he had her folded in half. As she watched her friends have sex, Oliva repositioned herself behind Jack. Like a devil on his shoulder, she encouraged him, "Stop holding back and do it, she wants it." He could feel her tits pushing into his back and her hands moving around his body, and her lips working on his neck and shoulder between whispers into his ear.

With all the going down while he looked down at Madison's face as he thrust into her. He could feel the build-up rising in his balls, and the look on her face said that she was closing in on another orgasm as well.

"Can't hold back anymore, gotta cum," he announced, giving Madison one last chance to back out. She just gave him a simple acknowledgment nod as she moaned. He gave three more pumps and then buried his cock to the root inside of Madison and then let it rip. He blasted her over and over again.

"Jesus, Jack," Madison moaned as she felt the steady steam of cum filling her quivering womanhood.

When he did finally stop and did pull out, Olivia was right there to polish his dick clean of the mix of his and Madison's cum. Though Olivia did have ulterior motives as well. Even after she had given his cock a spit shine, she still kept blowing him for a bit longer, not giving his dick any chance to go down at all. Once she felt his cock twitching in her mouth she knew he was ready to go.

She had Madison move up on the bed and then she laid down herself between Madison's legs. Olivia then went to town on her friend's snatch. Freshly full and leaking with Jack's cum, Liv at Madison's pussy and cleaned it of Jack's jizz. Jack took this all in and watched Olivia lay on her stomach in front of him. He knew she loved to do it prone, and he had an open opportunity to do that, but he was going to put that on hold for a minute. He had already creampied Madison Iseman, there was no chance he was not about to do that to Olivia Holt as well, but first, he was going to eat that pussy. He got down low and spread Olvia's legs. Feeling him moving her, she gave up little resistance and let him move her body around how he wanted. With legs open he also used his hands to spread her ass so he could get deep into Liv and bury his tongue into her.

For the next several minutes, the three of them were laying in a straight line. Jack laying on his stomach eating out Olivia, who was laying on her stomach eating out Madison, who was on her back. Madison was the first to cum, as she cried out while grabbing onto the bedding which between sweat and cum was becoming wetter and wetter.

Before Olivia could have one of her own, Jack pulled away from her. She let out a disappointing groan. That groan was soon replaced by a sudden squeal from the current Broadway actress as she felt Jack wedge his cock into her tight box. Olivia was still licking her friend after Madison orgasmed, but she soon was too distracted to continue. The orgasm she almost had from his tongue was now impending as he took her prone on the bed.

"Yes, Jack, keep going," Olivia moaned. She was now holding onto the bed tightly. She was so close that she began rocking her body back into him. It was only a matter of time, Jack could feel the buildup happening, and then suddenly she popped. Olivia cried out and once again she drenched the bed below her as her body twitched in orgasm bliss. Jack pulled out as soon as he felt her cumming. God knows he loved that feeling from her, but he loved it a little too much and was not ready to be done with her.

While Olivia was cumming, and then coming down from her high, Madison moved in and she repeated what Olivia had done and sucked his cock clean of the other's juiced. Once she had sucked him clean, both Jack and Olivia were ready to take things to the next step.

Neither were usually much for reverse cowgirl, but there was a full-length mirror across from the bed and on the wall far wall. He sat down on the edge of the bed and pulled Olivia on top of him. She sat right on his cock and began to bounce on it. The two of you are looking at each other in the mirror. She has a bright smile on her face and her tits are shaking as she bounces up and down on his dick. For the first 2 minutes or so, Jack is just happy to observe Olivia. Putting aside the feel of her tight pussy gripping his dick as it goes up and down the shaft, getting to see a naked Olivia Holt bouncing like this was something Jack felt incredibly lucky t see.

Eventually, he did get into the action, brushing her hair over to one side, and then moving his hands around her body. One hand when north to cup her breast and the other traveled south between her legs. As she had done to, him, he began kissing the side of her neck as he rubbed her clit and tweaked her nipple.

"You know this was what I was thinking about when you were on stage, right?" he said into her ear. "As good as looked on stage in your costume, I couldn't help but think about your sexy body and how you'd look doing all that without anything on."

"That's why you got hard?"

"Um-hm," he said as he kissed her neck. "And then my mind went to how much missed the feeling of cumming in the tight pretty pussy of yours."

"Maybe you should stop thinking about it and do it already," she told Jack.

"You want that?" He asked her.

"You know I do," she moaned. Jack had her spin around. She was now sitting on his lap, facing him, with her legs wrapped around his back. With their faces just inches apart now, they began making out as they fucked. Olivia rolled her hips while on top of him. He did not give Oliva any warning before cumming. He just moaned into her mouth as they kissed and let it go. Exploding his load into her. When she felt him cumming, she moaned right back to him and her nails dug into his shoulder. Even as he was cumming she continued to move her hips until she got off once again as well. After they finished, they moved back and lay on the bed next to Madison, who had been fingering herself as she watched Jack and Liv fuck.

The three of them all lay in a pile in the guest bed for a few minutes, catching their breaths and coming down from the sexual high. Olivia suggested that if they were going to go to sleep, they should all go to her bedroom. She didn't say why, but they all knew the why. Between sweat, cum, and vaginal fluids, the sheets on the guest bed were at a minimum moist, and in spots were just flat-out soaked. So they got out of the guest bed and headed to the master bedroom, but before getting back into bed it was suggested that they should all take a quick shower first.

While the three of them washed the sex off of each other, there was a significant amount of bumping, grinding, and touching between the three as they shared the shower. Some of it was accidental, some of it not so much. The bumping increased as Jack's shaft swelled to its full size. Madison and Olivia enjoyed teasing Jack's hardon. Although the teasing from the two short blonde actresses was becoming a little too much for him. He finally snapped when Madison dropped the loofa and bent down with her straight legs and her ass pointed right at Jack as she went to pick it up. He couldn't help himself and quickly moved right up behind her and thrust half his cock into her.

"Ahh! Fucker!" Maison yelped in surprise.

"Tell me to stop, and I will," he told her as he pushed the rest of his rod inside of her. She said nothing, so he started fucking her. Maison raised back up a bit and put her arms out to brace herself against the shower wall. Olivia was not going to be left out of the action. She moved to the side of both Madison and Jack. With one hand she pulled his face down to kiss her, and with her other hand, she moved it between Madison's legs and teased her clit.

"Oh god, seriously Liv?" Madison moaned and questioned her friend as she felt her love button being played with. Not to leave her out, Jack moved a hand between Olivia's legs and fingered her while the two of them made out and he fucked Madison. With the two of them working on her, the Jumanji actress did not last long. She let out a moan and her leg buckled as she came. Jack grabbed her around her waist to make sure she did not fall. Once she was steady on her feet, Jack pulled out of her and turned to Olivia. The Cruel Summer actress wrapped her arms around his neck and lept up. Jack caught her body and in no time she had his cock fully embedded in her. As they fucked, Madison gave herself one more long rinse under the shower spray before leaving the stall.

"You two have fun," she said and then had Jack turn his head towards her and she gave him a long loving kiss. "Thanks for today," she told him before stepping out of the shower and wrapping herself in a towel. Meanwhile, Olivia and he were lost in their own lust-filled world, aggressively fucking against the glass of the shower stall. Olivia had her back agast the glass, her hands holding on to the top of the shower above her, and had her legs over Jack's shoulders. The two were going at it, until Jack tried to readjust his stance and almost slipped on the shower floor, nearly bringing them both tumbling to the floor. After that, momentarily stopped what they are doing and turned off the water, and got out of the shower. They did not move far as they set up right on the large bathroom countertop. Olivia stood in front of the counter and bent down at the waist pushing her ass back at Jack. He quickly got behind her and lifted her leg onto the counter before sliding his manhood right back into Liv's snug wet box. As they had sex on the counter Oliva maintained eye contact with Jack nearly the entire time through the mirror.

"God, Liv. You feel so good," he groaned.

"I know what you mean, I love how you feel inside of me. I don't want it to stop."

"Yeah, but I can't hold out much longer."

"Just do it, fill me. I want it."

"Turn around!" he said loudly. He pulled out, and Olivia had barely got her foot to the floor before Jack had his hands on her, hips, Spinning her around and lifting her onto the counter. He quickly buried his cock back into her. After two more pumps, Olivia reiterated her desire for him to unload inside of her.

"Now Jack, do it now!" She demanded him and his cock busted, and that feeling got Olivia to hit her climax as well. They both came hard. He moved in to kiss her, and they exchanged a series of kisses, as euphoria from their orgasms died down. They cleaned up a bit and went into the bedroom and saw Madison sleeping in the bed. Jack had to work the next morning and debated heading to his hotel at that point in the night. Olivia asked him to stay and when he was still on the fence, she promised him a morning blowjob before he left. That made his decision an easy one. He set his alarm for a few hours and got into bed with his two actress friends. Olivia slept on her side in the middle of the bed facing Maidson, and Jack slept on the other side of her spooning with her.

Olivia was true to her word and sucked Jack's cock when his alarm went off the next morning, and Jack got a great start to the day before heading to his hotel room for a quick shower and change of clothes before heading out to work. The next day Madison flew back to LA, while Jack still had a few more days left in New York. He got a call from Olivia later that night.

"Hey, do you mind coming over on Friday and taking Roger for a walk after you're done with work? I can leave a key for you at the front desk."

"On Friday? Liv you know that's my last night here. I was planning on going out with people after work."

"I know, but I thought you could help me out and then we can do something after the show."

"So you want me to take your dog out and then just hang out at your place by myself for a few hours?"

"Yes, but I would put it as more as I want to be at my place when I get home with my costume in my bag. And I was hoping you'd be waiting in my bed… preferably with your pants on the floor."

[MacDennis]

10 outta 10

[TPG]

Grrr that was hot as fuck!!
I think this finally turned me into a fully fledged Madison fan now.