Lucky Bastard 30: Gifted
Starring Natalie Alyn Lind and Skyler Samuels

Code: MF, FF, MFF, Oral, Creampie, Anal
Written by MiamiLyfe
Disclaimer: The following is completely fiction and it is nothing but pure fantasy.

I was sitting in my office doing the same work I had been doing the past several days, basically putting everything I had done for my next movie on hold. It was still in the early stages of everything, but I had most of my major acting roles and important crew positions filled. What had caused the shakeup was that Hailee Steinfeld, who was set to star in the film, was approached by Marvel to potentially be one of the leads in their upcoming Disney+ series, Hawkeye. Hailee and I had both been looking forward to doing this movie since this would be the first project we actually worked together on, but I knew the Marvel opportunity would be huge for her, so I was not going to let her pass on it. So, for now, everything on my movie was stalled until Marvel and Disney decided and released a shooting schedule. With some good fortune, we'd be able to set it up so Hailee could do both the movie and the tv series and keep the rest of the people I had hoped to hire. I was writing an email to my would-be cinematographer when my phone chirped with a text notification.

"You cheating bastard," the text message read.

"You this?" I texted back, knowing full well that Katherine McNamara was texting me. It'd been several weeks since we first met at an after-party, and we'd texted back and forth several times since.

"You know who this is, you cheater!" she replied

"How am I a cheater?"

"Olivia told me all about you and Hailee. I know you two were a thing even before our bet."

"The bet was that I could take anyone women home that we agreed to be the target. You never said it couldn't be someone I was dating or had slept with before."

"Bullshit. You cheated, so you lose."

"You saw that video. Trust me, in no way, did I lose that night."

"Whatever. You cheated, so I'm not paying for dinner," Kat replied. We went back and forth for a bit before I finally agreed that while I did not lose the bet, I did hustle her into a bet I knew I was going to win. I also told her that I would be up in Vancouver in two weeks, where she was shooting some stuff for Arrow. I was going there to look at a few locations for my movie, and since we'd both be there, I agreed I would buy her dinner then. Once we had our plans, I put down my phone and tried to get back to work, but it wasn't long before I was interrupted again.

"Knock knock," I heard a woman say as the door to my office opened up. Looking up from my computer, I saw Natalie Alyn Lind standing in my doorway. Nat was dressed in a white button-up shirt, short black shorts, and black boots while holding several shopping bags.

"Oh, hey Nat. What's going on? How have you been?" I asked, trying to mask some of the discomfort in my voice. I had not seen Natalie since Hailee and I had become a couple.

"I've been good. I was just shopping with Sky and thought I should stop by," she said as she entered my office and closed the door behind her. "Eddie, I just wanted to apologize for how I acted after I found out about Hailee."

Natalie talked about how she acted when she found out that Hailee and I had started dating. While we were in an open relationship, the fact that I was in a relationship at all bothered her. I knew Natalie had a crush on me, but I didn't expect her to care or take the news the way she did. At first, I did not hear from her for about three weeks, and then came the first of many texts. Natalie repeatedly texted me that I should be with her, and she'd also send nude photos 3-4 times a week. Some were of her at home, others from her hotel rooms, and some were of her at gym showers. Also, some were some pretty basic nude mirror selfies, while others were a bit more graphic. The most explicit thing she sent was the night after her birthday. It was an hour-long video of her on the floor masturbating in front of a full-length mirror. She used several vibrators and dildos, sometimes more than one at a time. The most shocking thing was when she used a suction cup to mount one of the dildos on the mirror and fucked herself doggy style. The entire time she moaned and called out my name. Hailee knew about most of the text, but I kept that one video a secret. I tried to explain to Natalie early on that I liked her as a friend and stuff, but she didn't want to hear it. The truth was I really did like hanging out with Nat, and the sex was great. Excluding Hailee, Natalie was right there with Victoria and Olivia as my favorite hookups. But just like VJ and Liv, I never saw her as anything more than a friend with benefits.

"I know I was a little over the top, and I am sorry about that. You and Hailee are great together, and if we were together, I wouldn't have met Jordan."

"That's great. I'm glad things worked out," I sincerely told her. "I gotta tell you, some of those pics you sent were very tempting. If I was with anyone other than Hailee, I don't know what I would have done."

"Really?" Natalie said while smiling brightly.

Skyler Samuels sat in the food court of the Glendale Galleria. She was picking at her french fries and looked at her phone again. Skyler had come to the mall to hang out and shop with Natalie, but after doing some shopping, Natalie had left her saying that she wanted to say hi to her producer friend that she hadn't seen in a few months. Nat told Skyler that she'd meet her back in the food court in 20 minutes. That was 35 minutes ago. Skyler knew letting Natalie go alone was a mistake. Nat had a severe crush on him and took it hard when he started dating someone else. Natalie said she was over him, and while it seemed like it, Skyler doubted that more and more as each minute passed. Finally, Skyler got tired of waiting and decided to track down her friend.

Skyler knew where Ed's office was, so she had no problem walking over to his office just a block away from the mall. No one was in the main lobby area, but she could hear noises coming from the one closed door in front of her. Walking right up to the door, not even bothering to knock or give any warning, she pushed open the door and stepped right in. Skyler had an idea of what she might see behind the door, but the sight still took her breath away.

"Oh my God...oh my God, Skyler!" Natalie called out. "I'm cumming! I'm cumming all over Eddie's big dick! aahhhhh!" she screamed as she orgasmed. What Skyler had walked in was Natalie naked except for her boots was standing up and bent over the desk facing the door. Her large breast wobbled wildly due to Eddie shaking her body as he fucked her from behind.

"Natalie! What are you doing!?!" Skyler yelled while stepping into my office and closing the door behind her. "What about Jordan?"

"Skyler, it's fine. I just needed this," Natalie tried to explain. I stopped fucking Natalie, and I backed away from her and moved to the side. Skyler let out a gasp when she saw my hard wet dick with her eyes. "I needed one last fuck to get out of my system. You know how much I was craving his dick." Natalie walked back from around the desk, still only dressed in her boots, as she talked to Skyler.

"This is exactly why I didn't think you should come here alone," she said in hushed tones.

"And this is exactly why I did come here alone," Natalie explained. Nat then noticed how Skyler's eyes darted back and forth between her and my dick. She then reached out and took her former Gifted co-stars hand. "Why don't you join us. It can be just like that night in the hotel after the Preakness."

Skyler was hesitant, "I don't know."

"Sky, you had me tell you all those stories about Eddie and me, you've looked at all those pictures I've taken, and now it's right here. Look at it." Both of them turned and looked at me as I continued to stand naked behind the desk. Natalie then leaned in and whispered into Skyler's ear, "It feels even better than it looks."

"Okay," Skyler gave in.

"YAY! You're gonna love it!" Natalie said with a big smile. Skyler had been dressed in jeans, a tight black shirt, and black heels, but Nat helped to quickly strip her out of all of her clothes. Skyler was only about an inch taller than Natalie, but the two had completely different bodies. Natalie was curvy, to say the least, while Skyler was more leggy and lithe. I'd seen Nat nude a bunch of times. Her large breasts, dark reddish nipples, squeezable ass, thick thighs, and clean-shaven pussy. Sky, on the other hand, was paler, with light pink colored nipples capped off her upturned b cup breasts, had slender legs, and a trimmed blond bush. As the two women walked towards me, I sat down in my chair. Skyler got down on her knees while Natalie sat on the arm of my desk chair.

"God, it looks even big than it did in the pictures," Skyler said. Natalie reached down and pulled the condom I had been wearing off my cock and then took hold of my poll and aimed it at Skyler. She looked up at Natalie and me before wrapping a hand around my dick. She opened her mouth and began licking the tip of my dick. As Skyler started sucking on my dick, Natalie pulled my head to her chest, and I began kissing and sucking on her big beautiful tits. I put a hand on her thigh and slid it up her higher and higher as I alternated my mouth between her tits. I began fingering her twat as I continued to suck on her breasts, and Skyler blew me. We kept going, and as I could feel the pressure starting to build in me as Sky sucked on my balls, I could feel Natalie getting wetter and wetter as I fingered.

"Ugghhh, God. I need more," Natalie groaned in frustration. "Ready to get fucked, Sky?"

"Yes! Yes, I needed it," Skyler replied. While she may have been hesitant before, she seemed to have built up some enthusiasm as she was on her knees sucking my cock. Skyler stood up, and Natalie jumped off the chair and onto my desk. Nat laid back and spread her legs wide.

"Eat my pussy," Natalie ordered Sklyer, "while Eddie shows you what his big dick is capable of." Skyler bent over the desk and gave her friend's pussy a few long teasing licks along her folds. I got in behind Skyler and began to push forward. Skyler gasped as she felt my tip spread her open, but my dick was met with some resistance. While she was wet, she was not as wet as I would have liked her. So I pulled my dick back out, bent down, and began licking and sucking on her pussy. It's incredible how every woman has their own distinct taste and smell. While I worked to get Skyler wetter, I could hear moans coming from the desk that let me know that Sky was working on Natalie's pussy as I worked on hers. When I believed her to be wet enough, I stood back up and tried to thrust into her once more.

"FFFUUUUCCKKKK," Skyler groaned as she felt me stretch her pussy as I worked more and more of my cock into her.

"I told you it felt amazing," Natalie reminded.

"So good, Yeesssss!" Skyler said as I started slowly thrusting in and out of her. She tried to say something else, but her voice got muffled as Natalie pushed her crotch into her friend's face. As I slowly started to build up speed, Skyler became more and more animated in her reactions to my fucking. Natalie, meanwhile, went back and forth between moaning in response to her friend's tongue being inside her and egging me on as I fucked Skyler. Telling me to 'fuck her hard,' 'give it to her good,' 'she'll never admit it, but she's been desperate to fuck you, 'give her that dick she's been obsessing over. All of the encouragement from Natalie was really doing the trick as I was now giving it to Skyler as hard as I'd ever drilled any woman before. On more than one occasion, my thrust into Skyler, who was holding onto the desk, actually caused the desk to move. At this point, my desk was off by about 30 degrees off from where it had started. It was also then that Sklyer came and screamed loudly as she did so. Both her legs buckled, and I had to support her from falling down the floor. As her orgasm still flowed through her body, I picked up Skyler and placed her on the desk next to Natalie, who I then pulled closer to the edge of the desk. Natalie was excited as she knew what was about to come.

"I want you to fuck me until I scream and then fill my pussy to the brim with your cum," She told me.

"Yes, Ma'am," I said before slamming my dick into the Tell Me A Story actress. Natalie quickly wrapped her legs around my waist as we had sex on my desk. We kept on going at it hard as Sklyer began to come out of her orgasmic haze.

"Fuck, that was amazing," Syler said to no one in particular.

"I know, fuck, I love his dick. I love how he fucks me, and I love how he makes me cum!" Natalie told her friend. If this really was one of the last times Natalie and I would hook up in the foreseeable future, we were both making the most of it. As we went at it, Skyler turned to her side and began to watch us. She was still within arm's length, so I let go of Natalie's hip, moved it over, and began strumming Skylar's clit with my thumb. When my eyes moved from Natalie to Sklyer, Natalie also turned and looked at her friend, who was staring back at her. Skyler moaned as I teased her clit, and Natalie reached over and pulled the former Scream Queens actress's face towards her, and the two women kissed. They made out while I fucked Nat. The three of us mingled in a passionate lust-filled trio on my desk until both Natalie's and my orgasms began nearing points of no return. I had stopped playing with Skyler and had a hard grip on Nat's hips as I gave it to her as hard as did the other blond earlier. Meanwhile, Skyler was now draped over Natalie's body and was sucking on her big gorgeous breasts.

"HMMMM I gonna cum, don't stop, don't stop, don't stop so close," Natalie kept saying over and over again.

"Fuck I'm gonna cum" I warned her as I slowed down the pace of my thrusting but was now pumping my rod as deep and hard into her as I could.

"Do it! Fill me! Do it now! YESSSSS!" Natalie's eyes rolled back, and she arched her back up towards the ceiling as she came, and I shot my load as deep into her as possible. Her body trembled as I shot rope after rope of cum into her. When it was over, I collapsed into my chair, and Natalie lay on the desk, barely able to move. The only one who could move around was Skyler, who used her finger to scoop up and taste some of the cum leaking out of Natalie.

"Umm, tastes pretty good," She said after sucking her finger clean. "So Natalie, did you everything out of your system?"

"No," Natalie said breathlessly.


"No. There is one more thing I need. I, I just need a minute." We just stayed in place for a few minutes until Skyler started to play with Natalie's pussy a bit, causing more cum to leak out of her. Skyler could not help herself from leaning down and licking up the semen as more came out. Next thing you know, she is all the way in on going down on Natalie, eating my cum out of her. As she did that, it seemed to give Natalie her second wind, and she got more and more energized as she had her pussy eaten. And watching them go at it also caused my dick to stir a bit.

"Okay, okay, Sklyer, stop, please," Natalie pleaded. As Skyler sat up, Natalie rolled off my desk and quickly walked over to the shopping bags she had brought in with her. Riffling through a few bags, I wondered if she knew the view she was giving me. Nat had her legs straight and her ass pointed towards me as she bent over at the waist. After going through two or three bags, she finally pulled out a bottle of something and then walked back towards Skyler and me.

"Is that lube? When did you get that?" Skyler asked

"Yes, and don't worry about it," Natalie told Sky and then turned her attention to me. "So, um, I've been thinking about this for a while. And Eddie, I was kinda hoping you'd do me in the butt. I've never done anal before, and I want you to be my first," Natalie said sweetly and nervously.

"What, what? I thought you told me you had done it before?" I asked.

"I like to talk a big game, and technically I don't think I ever actually said that I had done it."

"So you want me to take your anal virginity?"

"Yes. I thought about this, and I trust you, and I just want you to be the one to do it."

"I mean, I'm flattered, sure," I told her, and that caused Natalie to give a big smile.

"You're gonna try and fit that thing in your ass? Seriously? How?" Skyler asked.

"I've been practicing," Natalie said confidently.

"With what? An actual eggplant?"

"No. Just some toys I have. It'll be fine...I think."

"Alright, if we are going to do this, let's do it on the couch." I took a condom out of my desk drawer, and the three of us went over to the couch in my office. I took the lube from Natalie and instructed her to get on her knees on the sofa, face the wall, and stick her ass out. I then squirted some lube into my hand. As I began to finger and lube up Natalie Alyn Lind's asshole, Skyler Samuels dropped back down to her knees and began to suck on my cock. I'm not sure if she was trying to get me nice and hard for Natalie or if she had just enjoyed the taste of mine and Nat's juices and cum mixed together so much that she was now cleaning my cock of any of that mixture. Either way, she was doing a fabulous job. I was hard as a rock, and Natalie was starting to press back onto my hand as I used two fingers now to finger her virgin butt hole. When she was ready, I had Natalie rotate, so she was bent over the arm of the couch and had her ass high up in the air. Skyler rolled the condom down my dick and then took a glob of lube and spread it on my dick and gave it several good pumps.

I then got in place behind Natalie. I rubbed my dick along her juicy pussy lips and told Natalie to relax. When she said she was ready, I took my cock and positioned it against her back entrance. I slowly pushed forward, and Natalie tightly gripped the couch. At the same time, she grunted and grimaced as she felt her anal ring being stretched like never before.

"Natalie, are you okay?" I asked, concerned. I only had the head of my cock in her at this point.

"Yes, keep going," she replied

"You sure?"

"Yes! I want it all inside me," She said, even thrusting her ass back a bit against me as if to prove her point. I reached around and began stroking her clit as I began to push forward once again. I was hoping that flicking her clit would get her to relax. Skyler just sat back on the floor and watched. It took a while, but I eventually did get my whole dick inside her, and I just sat there for a full minute with my entire rod fully inside her, letting her get used to the size. When she said she was ready, I slowly began to move again. I gave her some slow and shallow thrusts and started working my way up. It took a while, but she slowly began to relax.

"Oh my god, Natalie? Are you actually enjoying it?" Skyler said from the floor.

"Kind of," she replied with a smirk as we picked up the pace a bit, and Natalie began pushing her ass back into me to meet my thrust. We began to find our rhythm, and Natalie began to grunt as I started to really fuck her ass. As I increased my speed, Natalie would loosen up and seem to enjoy herself more, and as she enjoyed it more, I increased the speed of my fucking more. Apparently, watching Natalie lose her anal virginity was pretty hot as Skyler began fingering herself as she watched me fuck her friend in the ass.

"Oh my god! Oh my god!" Natalie said in disbelief as I spanked her ass while continuing to pound. "I'm I'm I'm…..cummmmminnnnggggg," Natalie then blurted out as she came. I kept on going as she came, utterly undeterred by her latest orgasm. I gave her ass a few more spanks as I pummeled her asshole with my cock. I then stopped.

"Wait, why did stop? What? What are you...oh fuck!' Natale was confused as I grabbed her legs and pulled her off the couch, and I stood up. I tried my best to keep my dick in her tight hole. When I had her how I wanted, we were in a standing reverse position, both of us looking out in the same direction as I held her up by her thighs (I later googled to find that it was named the butterfly position). I began to bounce her ass up and down on my dick. It was not an easy position to keep up, but it didn't matter because I knew I would cum soon anyways. I kept bouncing her until I felt that my balls were about to burst. I then purposely fell back on the couch and let gravity do the work of literally slamming Natalie's ass down as hard and as far as possible onto my dick. As soon as she slammed down, I began emptying my balls right into her rectum. Natalie was so surprised by everything that she didn't react. She didn't make a sound. However, it must have looked pretty hot because I could hear Skyler bring herself to orgasm.

"Wow," That was all Natalie had to say when she finally regained the ability to talk. By that point, she had a full load in her ass, my cock, while still inside her, was starting to go flaccid, and Skyler was laying on the floor enjoying the afterglow of her orgasm. We all just stayed there for a while before Natalie got up to go to the bathroom and clean up, and then we all got redressed. The ladies took up their shopping bags, and we walked out to the lobby of my office.

"That was fun. Ed, you lived up to Natalie's stories," Skyler said before giving me a kiss and opening the door to leave the office.

"Thank you for everything, even though I might not be able to sit comfortably for a week," Natalie said. She then pulled me down for a kiss, slipping in a little bit of tongue, before leaving the office with Skyler. After they left, I shut the door, turned around, and saw Ryan standing in the doorway to his private office.

"I love you, man," he said. "But we need to soundproof your office. While you three were doing what you were doing, I had to take a conference call. Not easy to explain away those noises."

"I'm sorry," I apologized.

"No, you're not," Ryan said.

"You're right. I'm really not."