Lucky Bastard 25: Pre Valentine’s Day Fun
Starring Bailee Madison and Hailee Steinfeld
Codes: MF, MFF, Oral, Anal, 69,
Written by MiamiLyfe
Disclaimer: The following is completely fiction and it is nothing but pure fantasy.

It was Friday night the week after screenings in Scottsdale and I was relaxing at home. After two busy weeks, I just wanted chill on the couch and catch up on some TV. It was now 11:30 PM and I had just watched 3 episodes of The Gifted and was now starting on the latest episode. As I watched, I was also playing on my phone and a few times I opened up my messages and considered texting Natalie Alyn Lind. I generally like the show, but watching Nat’s tits bounce as she ran around in heeled boots and skin-tight jeans, I could not help but be tempted to see if she wanted to come over for some fun. I also thought about pulling out the air-gapped laptop I had which contained all the naughty and sexual photos I had taken or had been sent by female friends over the years, including several explicit photos Natalie had sent me from her trailer just a few weeks ago.

As I contemplated this, my phone suddenly began ringing. I looked at the number on the screen, and while I didn’t recognize the number I knew from the area code that it was an LA number. Figuring it wasn’t a telemarketer or scammer based on the time of night, so I decided to answer.


“Eddie! Yay! You answered,” I heard a voice say but there was a ton of background noise that almost drowned her out.

“Who is this? I can barely hear you.”

“It’s Bailee.”

“Who?” I asked. I could not really tell if she said Bailee or Hailey.

“It’s Bailee!”


“Yes, Bailee. The girl you ate out at the gym last month.”

“Yeah, Bailee I know who you are. Why are you calling?”

“Where are you? What are you doing?”

“I’m home. Watching TV. Why are you calling?”

“Can I come over?”


“What? Why do you think? So Can I?”

“I guess so. Do you need me to text you my address?”

“No, I have it.”

“What? How? How do you have my address, and for that matter how do you have my number?”

“Hailee gave it to me,” She then hung up. I looked at the clock, I paused the show and decided to take a shower before Baillee arrived, making sure to give my cock and balls a good scrubbing before throwing on a clean t-shirt and loose sweatpants (sans underwear). I then went downstairs and finished watching the episode of the Gifted I had paused. It was not until an hour later I heard a car pull into my driveway and then had my doorbell ring. I open up the door to find Bailee Madison standing there dressed in all black; a black spaghetti strap tank top, tight black pants, and black boots.

“Heeeeyyy” Bailee said before wrapping her arms around me and kissing me on the lips. I could taste the alcohol on her breath. From the car, I could hear two female voices yelling out. One just yelled out a ‘whoo’ and the other yelled out “Get it, girl”. Bailee then entered my house and I shut the door behind her.

“Nice place,” she said as she dropped her clutch on the floor and walked through my house. I followed her into my living room where she had settled onto my couch. I took a seat on the opposite end of the couch.

“So, Bailee, what are you doing here?”

“I thought that is pretty obvious, isn’t it?” She said as she ran her hands up and down her body.

“Yeah, but why me and why tonight?”

“I broke up with my boyfriend a few weeks ago, asshole cheated on me, and my friends think I need to get back at him and get past him by hooking up with another guy.”

“Were those the friends in the car?”

“Yeah. Tessa Brooks and Peyton List. Do you know them?”

“I’ve heard of Peyton, but no I haven’t met either of them.”

“Well, Tessa thought I should hook up with some guy at the club we were at, and Peyton was saying how she would set me up with her brother. And I was like, been there done that. And I told them that if I was going to hook up with anyone, I knew a guy who ate me out better than Alex ever did and is super hung. By the way, I promised them a picture of your penis.” Bailee had now moved up next to me and was pressing up against me.

“Been there done that? You hooked up with Peyton’s brother.”

“Ugghhh yeah, twice. Asshole. Both times he lasted maybe five minutes and came inside me with no warning. That why I make sure guys wear condoms now. Though the worst part is I’m up on his stupid wall.”

“His wall?”

“In his closet, he has a wall with all the girls he’s ever gotten a BJ or had sex with,” she explained. She then got really excited, “Oh! You’ll never guess whose picture is in the center of the wall”


Bailee then leaned close and drunkenly whispered into my ear, “his sister.”


“Yup he hooked up with his sister. I was there. There was a mixup a few years ago when we were playing 7 minutes in heaven. Someone set it up so they would be put in there at the same, but they didn’t know it. Debby Ryan then opened the door and flipped on the light a minute early, and there she was, on her knees, cum on her face, licking the tip of her brother’s cock. It was so funny.”

“That’s pretty messed up.”

“I know, but wanna hear something else? I heard Spencer telling my ex that he and Peyton had sex. And they do it regularly whenever one of them is in the mood. Peyton denies it, but I’m not sure I believe her.” I was not one who was really into incest porn or stuff like that, but with Bailee pressing her tits up against my arm and her hand stroking my dick through my sweatpants, I could not help but get aroused as Bailee told her story.

“No offense Bailee, I don’t really care about Peyton and who she is fucking. Now, can I tell you a secret?” Bailee smiled an eagerly nodded her head. I mimicked her and whispered into her ear, “You’re way hotter than Peyton. Given the choice between you over her, I’d pick you every time and I have the hard cock to prove it.” I pressed her hand firmly against my hard rod.

After I told her that Bailee was all over me. She moved onto my lap and as we made out, my hands explored her body. Groping her tits and her ass.

“Take off your pants,” she told me.

“Take off your clothes,” I responded. Bailee quickly got up off the couch and stripped off her clothes, while I pushed my sweatpants off and ripped off my shirt. Once my shirt was off I got my first clear view of Bailee’s naked breasts. They were a large b-cup, close to a c-cup with dark quarter-sized nipples. As she pushed her pants and lace thong to the ground, I could see that she still had a neatly trimmed dark haired bush.

“Whoa. It’s even bigger than I remember,” Bailee said as she got down on her knees between my legs. She grasped and played with my pole as if trying to measure it in her hands.

“I can’t believe I am finally going to do this,” She smiled before giving me the first lick of her tongue.

“Been thinking about this much?” I asked.

“Hailee told me a couple of stories about the two of you, and then after I saw it at the gym..” she spoke excitedly, “I mean, there has been more than one night where I was pretending my toy was you.”

“Then what are you waiting for?” With that Bailee spat in her hand and opened her mouth to take my cock into her mouth. She sucked on my mushroom head as her hands worked the shaft. After a minute or two she tried to take more into her mouth but struggled to get past 3.5 inches before she began coughing and gagging. She tried multiple times and just ended up with saliva dripping down her chin.

“Oh wow,” she said as she wiped her chin.

“Bigger than your ex?”

“For sure. I mean his was fine, but you’re just...” she went right back to suck my dick. Bailee was doing her best but it was fair to say she not the best cocksucker, especially when compared to several other women I know who were extremely gifted. I let her go a little while longer but I knew despite her best efforts and how good she looked naked with my love stick in her mouth, she was not going to get me off this way any time soon. When I had enough, I had her sit back while I laid on my back on the couch. I then had her get on top of me. While her legs straddled my face her mouth went back down to my dick. I pulled her waist down hard on top of me and drove my tongue into her pussy. She tasted just as sweet as she did at the gym.

Bailee’s pussy was wet before she even sat down on my face, but after a few minutes of eating her out, she began dripping down my face like a fresh peach. She continued to suck on my cock the best that she could while I ate her out, but once I began fingering her while sucking her clit, she lost her concentration, and just moaned while focusing on the pleasure. I kept attacking her pussy with my mouth and fingers until I finally got her to pop.

“Oh fuck,” the Good Witch star said as she came while sitting on top of me. When she calmed down a bit Bailee flipped around. She now sat on my stomach with my dick pointing straight up and resting between the crack of her ass.

“That was so good,” she said.

“We haven’t even gotten started,” I said before reaching around and smacking her butt with my cock. Bailee then put her hands on my chest and lifted her hips. She moved back a bit and had herself hovering just over my dick.

“Shit, condom! We need a condom,” she said. Bailee moved back a bit and sat back down, though we both let out a desperate moan because when she sat down my shaft rubbed up against her wet outer lips.

“In that drawer over there, there should be some,” I said pointing to an end table in the corner next to the couch. She crawled to the end of the couch, opened the drawer, and pulled out a condom.

“You keep condoms in your living room?” she asked as she opened the wrapper.

“You think this is the first time I’ve had sex on this couch?” Bailee just laughed as she tossed the wrapper to the ground and slid the large condom on me. Once it was on she once again rose up and had her wet pussy hovering just over my dick, this time however she did lower herself onto my dick. She grunted and bit her lip as her pussy stretched like it never had before.

“Fuck, it feels like you’re cock is splitting me in two,” She said when was halfway down my rod.

“You okay?”

“Yes, I’m good. Really good.” She said while she paused. Slowly but surely she began rocking her hips. Her pussy was so tight it felt like it was trying to strangle my dick. I let her go at her own pace to start. “Jesus” she moaned as moved her hips. While she focused on how my dick felt inside her, my hands roamed her body. Her tits were both perfectly perky, and soft and pillowy to the touch. Her ass was much the same way. Her body reminded me quite a bit of Victoria Justice. She was both very toned and fit, while at the same time had very soft curves. As Bailee continued to ride me she was starting to really pick up a pace more to my liking and yet had still not gone all the way down on my dick. Using my thumb to rub her clit as she rode me while I groped her tit with my other hand until I got her to have another smaller orgasm. Bailee then laid down on top of me, her breast pressed against my chest as she kissed me.

“That was good, but now I want you to fuck me like you do Hailee.”

“Oh yeah,”

“Um-hm,” Bailee nodded.

“Get up and bend over the arm of the couch.” Bailee climbed off me and moved to the edge of the couch. She spread her legs and bent over at the waist onto the couch. I got in behind her and rubbed my dick along her pussy.

“What do you want me to do again?”

“I want you to fuck me like you do Hailee.”

“Oh yeah?” I asked as I continued to tease her.


“Do you want me to really fuck you like Hailee?” I jokingly asked as I spread her ass cheek and tapped he butthole with my dick.

“NO! Not that. I haven’t done that and there is no way I am letting you shoved that beast into my ass.”

“Alright, no problem,” I said, lowering my dick and pressing back into her tight warm pussy.

“Oh god! You’re fucking huge.” she moaned as I pushed my full length into her. I left it in there for a few seconds to let her get readjusted to my size. I then slowly pulled out a couple of inches before slamming back into her. She let out a bit of a shout as a jammed my full cock into her. I then did it again, and again. Soon I had picked up speed and was jackhammering the 19-year-old actress with the biggest dick her pussy had ever taken. Her whole body shook as I pounded her.

“Yes! Fuck me like Hailee! Fuck me like Hailee! Gawd yes!” She repeatedly called out as we had sex over the arm of the couch. As much I had been trying not to think about Hailee Steinfeld over the last few weeks, hearing her name get called out while I was fucking only made me go harder. She climaxed at least two more times before I felt my jizz start to churn in my balls. When I couldn’t hold out any longer I gave her ass a slap, pulled out and spun her around. Bailee sat on the arm of the couch as I ripped off the condom and shot my load over her tits and face. Her cute face looked great smiling with cum dripping down it. Bailee fell back onto the couch when it was over. Laying on the couch, she still felt like she was in bliss.

“Fuck me, now I know why Hailee always has such a big smile on her face when she talks about you. That was great” she said while catching her breath, her face covered in cum.

“Yeah, that was fun, but we’re not done yet.”


“Not even close. You go clean up, I’ll grab some more condoms and we’ll meet upstairs in my bedroom.”


Next Saturday morning, Bailee was back over at my place once again naked on my bed. Just like the previous week, Bailee gave me a booty call on Friday night, and now we were just enjoying some Saturday morning delight. Thankfully unlike last time, she was not telling me to fuck her like Hailee. Bailee was lying nude on her stomach while I was prone boning her. The Good Witch star was moaning and holding on tightly to the sheets. I had used one hand for support as I angled my cock into her as I thrust in and out of her, and with the other, I played with her ass cheeks. I had already gotten her to cum once this morning and was building closer and closer to my own orgasm when my phone started ringing on my nightstand. I was not planning on answering it until I saw the word “Haiz” light up on my screen. The two of us had only spoken very infrequently by text the last 2 months, so for her to actually be calling me was highly unusual. I stopped playing with Bailee’s butt and grabbed my phone off of the table.

“Hello?” I answered

“Hey Eddie, how you been?” I heard Hailee say through the phone.

“Fine. What’s wrong?”

“Did you just take a phone call?” Bailee turned her head and looked back at me. Rather than answer her I just smacked her ass and continued to fuck her, though a little more slowly than before.

“Who was that?” Hailee asked.

“Your friend Bailee.”

“Are you two having sex right now?”

“Little bit.” I heard Hailee muttering something, but I could not make out what it was.

“I’ll make this quick then. I was wondering if we could meet up on Wednesday, I wanna talk to you about something.”

“Sure, sounds good.”

“Cool. Also, do me a favor, give Bailee a massive facial and take a pic of it for me. She’ll understand why.”

“No problem,” I then hung up the phone and tossed it onto a pillow.

“Who was that?” Bailee asked.

“Don’t worry about it,” I told her before pulling out and flipping her over onto her back. I spat between her breast and straddled her chest. Pressing her tits together, I began fucking her tits with my cock which was still slick with her pussy juices. While she was not stacked like Natalie, Bailee’s soft tits were still able to do a decent enough job. As I held onto and fucked Bailee’s tits my mind drifted to thinking about Hailee. It didn’t help that looking down at Bailee’s face, she happened to have the same hair and eye color as Hailee. I kept fucking her tits for another minute, Bailee would occasionally lick my tip as my dick slid between her tits. When I was ready to cum, I gave Bailee no warning before grabbing my dick and aiming it right at he face. Her eyes went wide as I gave my dick a few strokes before erupting.

“OH MY GOD!” Bailee called out as I covered her face with my load. When I finished I quickly grabbed my phone and snapped a picture of her. “Did you just take a picture?” she asked a little upset.

“I couldn't help myself. You looked incredibly sexy.” I wasn’t lying. Her cute innocent face being covered in cum was pretty hot. She still wasn’t happy about it, but I got her to pose for a couple more pictures before she went to take a shower. After she showered and left, I texted one of the pictures of Bailee’s facial to Hailee, then me and Hailee made more defined plans for Wednesday.


It was 11:00 AM on Wednesday and I was getting out of the shower after working out when I heard my phone chirp. I picked it up and saw that it was a text from Hailee. Apparently, she was outside in her car. I texted her back saying that I was running late and still had to get dressed. I let her know the door was open and she could come in and wait. She agreed but said she wasn’t going to tricked into coming upstairs. I laughed it off and got dressed.

10 minutes later I walked down the stairs and looked around for her, eventually finding her in the kitchen. She was dressed casually in a t-shirt, loose jeans, and sneakers. She also had a box of cereal from my pantry in her hand, which she was snacking on as she paced around waiting for me. Seeing Hailee walking around with her back to me I was filled with serval emotions. I had not seen her in person in a few months and what limited time we’d talked neither of us even mentioned the fact that she was single once again.

“You do realize that plan was to go eat lunch at a restaurant right?” I asked cheekily.

“Oh hey!” She said with a big smile as she spun around and saw me. She put the box down on the counter as she walked towards me. “I was hungry and just couldn’t help myself.”

“It’s good to see you,” I told her as we embraced in a big hug.

“You too, I’ve missed you,” She said as we hugged. What started off as a hello hug lingered longer than a normal hug would. I started to lighten my hold of her but she kept her arms tightly around me before she started to loosen her hug. As we pulled away from one another, our eyes locked on to one another. We were still very close to one another, looking into each other's eyes when she lightly licked her lips.

It’s uncertain who made the first move, but the next thing I know is that we were upstairs entering my bedroom. Hailee had her arms and legs wrapped around me, and I had my arms wrapped around her as we made out passionately. I was slowly walking us both into my bedroom and towards my bed. Neither of us said a word as I dropped us onto my bed. Nor did we say anything as the two of us stripped each other of our clothes. We’ve had sex many times before, but this time was unlike any of the previous times. There was no foreplay or anything at all. Instead, Hailee laid on her back her arms wrapped around my neck while she looked up into my eyes. Her mouth formed an “O” and she moaned as I slowly slid my dick into her. As we started to have sex in the missionary position Hailee once again pulled my face towards hers and push her tongue into my mouth. As I continued to methodically work her pussy with my large pole, Hailee wrapped her legs around me. As we broke off our kiss, in part so that we both could catch our breaths, Hailee kept her hand on the back of my head and made sure we kept eye contact the entire time.

“Roll over, let me be on top,” Hailee said. It was the first thing either of us had said outside of grunts and moans since we hugged in my kitchen. She unlatched her legs from around my back and I rolled us over. My cock never leaving her hot tight box as we spun over. With her now on top, Hailee sat up and worked her hips grinding herself on my dick. I grabbed firmly onto her ass as she rode me. As I played with her ass, Hailee moved one of her hands up and played with her nipples as she rode me. Hailee let out a loud moan and shuttered as she had a mini orgasm on top of me. After that, she leaned forward and began to really bounce herself faster on my pole. I was matching her bouncing with my hip thrusts. Within minutes we were both breathing extremely hard.

“Hailee,” I pleaded.

“Do it,” she said knowing what I was going to say. She gave me a quick kiss and then moaned, “I want it, I want to feel you fill me.” Hearing her say that was enough for me. I fired off my load deep into the Bumblebee star. Feeling my dick erupt and completely fill her pussy with my seed made her climax as well. When it was over Hailee just collapsed on top of me. We laid there on the bed, sweaty, breathing heavily and happy.

“So, no offense, but I don’t think we can be friends,” I told Hailee as we laid there.

“What?” she asked with concern and suddenly looked up at me.

“We couldn’t be in the same room for 5 minutes without ripping each other's clothes off and having sex,” I said in a light-hearted tone.

“Yeah, I guess that is an issue. Plus your dick is still inside me and I don’t feel like moving off of you any time soon.” She then moved up and we made out a bit more. Eventually, though we got out of bed, showered and went to go get something to eat in Larchmont. As we ate a Village Pizza we both confessed that we had real feelings for one another and that we should officially start dating, but since our schedules were still insane and could take us all over we agreed it should be an open relationship with a few rules. Some of the rules included, no sleeping with each others relatives, separately we could come up with a list of up to 15 people the other can’t sleep with, condoms have to be worn when with other people, we wouldn’t go two weeks without seeing each other in person (which meant I’d fly and meet her when she toured or was shooting a movie), and finally her ass was mine alone. After we ate we walked around Larchmont a bit, even holding hands at times. As we did our lap and we were nearing where we parked I got a text message.

“Who is it?”

“Bailee,” I told her.

“I can’t believe you hooked up with her.”

“What do you mean? You gave her my number and address, I kinda thought you were throwing her my way.”

“I gave her that info on Olivia’s birthday. She wanted to go, so when the party got moved to your place I gave her your info.”

“I never saw her there.”

“She didn’t stay long. She said she got there late and was only there for like five minutes. Apparently seeing almost everyone totally loaded and Debby Ryan getting split roasted right out in the open kind of freaked her out.”

“Huh, she told me you just gave it to her three weeks ago.”

“That bitch.”


“She had told me how she had run into you at the gym and how it was totally obvious that you obviously had feelings for me.”

“Which I told her specifically not to say.”

“Yeah well, she knew that I was trying to figure out my feelings for you and that’s when she decides to jump your bones. God, I can’t believe her. Let me see your phone.” I unlocked my phone and handed it over.

“What does she want?”

“She wants to come over tonight. I guess with tomorrow being Valentine’s Day and now being single she is feeling a little lonely.”

“And what are you writing to her?”

“To come over to your place tonight.”

“Huh? What are you up to?”

“You’ll see,” she said very playfully before giving me a kiss and walking us hand in hand to her car.


Several hours later, back at my home I happily invited Bailee into my place. Despite the coolness of the mid-February air, Bailee was dressed in little more than a white summer dress.

“I was surprised to get a text from you today.”

“I just couldn’t deal with listening to my friends talk about their Valentine’s Day plans anymore. It’s been a while since I’ve been single on Valentine’s, and I just...I just need something,” She then leaned into me and cupped my crotch, “I need this.” She then leaned in and kissed me.

“If that’s the case, you might as well leave your clothes here.”

“Okay,” She said. Even though she had called me for a booty call the past two weekends, her forwardness tonight surprised even me. She grabbed the bottom of her short dress and pulled it over her head. It was clear she had been braless when she came in and that was confirmed when she dropped her dress to the floor, and then she pushed her white lpanties to the floor as well.

“That’s new,” I said referring to the fact that she was totally clean shaven.

“I thought I’d do something special tonight.” I picked her up and carried her off to my bedroom, her shoes falling off along the way. I threw her down on the bed and spread her legs wide as I went down onto my knees on the floor and proceeded to eat her out. She literally must have shaved just before coming over because her pussy was silky smooth. She was also already extremely wet before I even started. I toyed with her briefly with my tongue before switching to rapidly fingering her with two fingers. It did not take long to get her to cum. After she came, I wiped my face as I stood up and stripped out of my clothes. Bailee turned around and laid on her stomach facing me, or more importantly, facing my hard dick. As I stepped up right to the edge of my bed, sticking my cock into Bailee’s face, I saw my closet door slowly open out of the corner of my eye. Bailee played with my rock hard rod in the hands before she finally opened her mouth, sticking out her tongue and running it up and down the sides of my dick.

“You taste different,” she said as her lips wrapped around the head.

“Does it taste better or worse?”

“I don’t know, it’s just different, she said as she continued to use her mouth on me.

“Well I hope it tastes good,” A naked Hailee Steinfeld said as she finally let her presence be known. She now stood next to me with her arm wrapped around my waist. “I had him soak his hard cock inside me before you got here.”

‘Hailee!” Bailee yelled as she spat out my dick, “Wha...what are you doing here.”

“Well, Eddie and I got together today and we both admitted our feelings for one another, and now we’re dating” Hailee answered happily, then pulled me in for a kiss.

“But, so...wait if you’re dating now then why did you let me come over?” she asked me.

“She was the one who texted you, ask her?” I told Bailee.

“Because I wanted you to know that I knew you were fucking him behind my back. But also because if it were not for you, who knows when we would have confronted our feelings, plus we’ve agreed to have an open relationship.”

“I’m so confused.”

“All you need to know is that you’re going to get exactly what you came here for,” Hailee then took hold of my dick, “but after tonight if you ever want this dick, you're going to need to ask me for permission first,” Hailee told her while repeatedly slapping her cheek with my hard tool. Hailee then let me go, and Bailee stared at us dumbstruck. “Well, what are you waiting for? Suck my boyfriend’s dick already.”

Bailee slowly slid me back into her mouth, though her eyes were on Hailee as she was still unsure of what was happening. Soon though Bailee was sucking me like normal, her mouth working the first three inches while her hand worked the rest. Hailee stood next to me, rubbing her nude body against mine and watching on as I had my dick sucked.

“Come on, is that as far as down as you can go?” Hailee said before putting her hand on the back of her friends head and pushing her to take more of my cock than before, but after another inch and a half, Bailee began coughing and gagging until Hailee let her pull back. “Here, let me show you how it’s done.”

Hailee got onto the bed and laid down next to Bailee. Pulling my cock towards herself, Hailee opened her mouth and swallowed my sword. She took a few inches at first but in a minute Bailee watched wide-eyed as she took my whole length down her throat. Hailee blew me for a little while before passing me back to Bailee. While she did the best she could, Hailee added her mouth as well. Using her tongue and lips to play with my balls and the side of my shaft that Bailee’s mouth could not reach. Hailee eventually pulled my dick back over into her mouth and had Bailee take over what she was doing. The two women passed my cock back and forth between one another until I could not take it anymore. I pulled away from the two of them and Bailee moved to the middle of the bed. I got up on the bed and sat on my knees. Spreading her legs and pushing her knees to her chest I moved my cock into position, while Hailee moved behind me.

“Wait, wait, condom,” Bailee said as my rod pressed up against her entrance.

“Not tonight,” Hailee said before pushing me forward so my head pierced her folds. I paused a moment waiting to see if Bailee was going to say anything, when she didn’t I slid further into her. She moaned loudly as I filled her pussy with my oversized cock.

“Got I’ll never get used to this. I can practically feel the thing in my stomach,” Bailee said as I started fucking her. Leaning forward I pressed her legs to her chest as I continued pounding her. Meanwhile, Hailee pressed herself into my back, whispering for me to fuck her friend hard. Hearing her encourage me just drove me harder. I soon had her cumming hard.

“So Bailes, do you like getting it raw dogged by my man?”

“Ugghh! I love it!”

“Good.” Hailee then moved out from around me allowing me to sit up straight. I moved Bailee’s legs off my shoulders, and she quickly wrapped them around my waist.

“Time for you to make it up to me,” Hailee said as she straddled her friend's face and dropped her pussy on her friend's mouth. As Haiz started grinding herself, she pulled me in and jammed her tongue into my mouth. We made out hard while I continued to fuck Bailee and Hailee rode her face. When we finally broke off our kiss Hailee kept her my head close to hers. “I want you to cum inside her. I want you to empty everything you have in those big balls yours into her pussy,” she whispered into my ear. She kissed me along my jawline before looking into my eyes and saying, “Do it.”

I grabbed Bailee’s hips and really started to drive my cock into her. I could hear muffled moans coming from out her cover mouth. My eyes bounced up and down between Hailee’s eyes and Bailee’s jiggling tits until my cock erupted. Bailee started squealing as I shot off, again and again, filling her completely. I kept my cock inside her even after I finished cumming. Giving her a signal, Hailee got off her friends face.

“OH MY GOD! You came in me!” Bailee yelled out when her mouth was finally uncovered.

“She told me to.” Was my response as I pointed at Hailee.

“SO!?!” Bailee breathed heavily. “And you came so much. When Peyton’s brother did it to me it was like a few squirts, and...and that felt like a hose was going off in my vagina.”

“Didn’t it feel amazing?” Hailee asked.

“Kind of, yeah.”

“Sit up, and watch this,” Haiz told her. Bailee sat up and Hailee pressed her hand against my chest signaling for me to back up. I scooted back and pulled my dick out.

“Holy shit,” Bailee said as she watched cum start to pour out of her. It was pretty hot to watch happen, and it got even hotter when Hailee dove down and began licking that cum that had leaked out. Using two fingers to scoop up some of my jizz she then offered it to Bailee. She was hesitant but Bailee eventually did lick Hailee’s fingers clean. Hailee then went right back down and stuck her tongue into Bailee’s twat. I just sat back and watched for a little while. Watching as the woman who just hours ago agreed to be my girlfriend ate my cum out of the woman who had been my booty call the last two weeks. My cock had hardly gone down after I came, and watching the two women go at it, it took little time for me to get back to full strength.

I continued to watch a little while longer, but at a certain point watching Hailee wiggle her butt a bit while she was on her knees and elbows became to much for me. Getting off the bed I stood at the side. I reached out, grabbed Hailee’s ankle and pulled her towards me. She looked back at me and knew exactly what was coming. When I stopped pulling, Hailee got into position, head down, ass up, and her knees spread wide right at the edge of the bed. Neither of said anything as I held her hips and pushed into her. Unlike with Bailee who needed me to ease her in, or with Hailee hours ago where we made tender love, this time Hailee and I just went from 0-60. Me slamming into her and her pushing back into me at the same time. The loud clap of our skin smacking into each other as we fucked hard. Bailee just sat back and watched with her legs tucked under her. I looked at her watching us fuck.

“So Bailee, remember when you were calling for me to fuck you like Hailee?” I asked.

“Yes,” Bailee replied sheepishly.

“You didn’t tell me about that,” Haile said as she looked back at me. “Jealous bitch,” Hailee said through gritted teeth, and I gave her ass a slap.

“Well, if you really want to get fucked like Hailee come here next to her.” Bailee didn’t move at first, but she eventually did move to the edge of the bed and got in the same position right next to Hailee. With her ass up and her pussy at easy access, I reached over and began fingering her pussy while I continued to bang Hailee. After a bit of time, I pulled out of Hailee and slid over behind Bailee. I proceeded to then bang Bailee just as hard and aggressively as I had with Hailee just minutes before, with the occasional ass slaps and all. Bailee let out hard grunts and moans and gripped the bed sheets tightly as I plowed her from behind. Meanwhile, as I did that I also was fingering Hailee as well. After a few minutes, I switched back over to screwing Hailee while fingering Bailee. I went back and forth between the two ladies.

I was back to doing Bailee when Hailee crawled away for a few minutes. I was too focused on the former Fosters actress to see what my favorite actress/singer was doing. However once she had moved back into position it was very obvious what she was done, as her butt hole was now shinnying with lube. Hailee looked back at me and simply gave me a smile and a wink as she wiggled her butt. I pulled out of Bailee’s twat and plugged Hailee’s ass with my dick. Hailee let out a high pitched squeak and her eyes rolled to the back of her head as I penetrated her butt.

“Fuck I love this,” Hailee groaned as took her ass. I have completely focused one Hailee’s backside, that I got a surprise when I looked up at one point and saw that Hailee had turned Bailee’s head and now the two women were kissing. I kept going as long as I could but time was no longer on my side.

“I can’t hold out much longer,” I warned the Hailee.

“Please just a bit longer,” Hailee begged. Meanwhile hearing that I was getting to cum once again made Bailee sit up and spin around. It was then Bailee fully realized what Hailee and I had been doing the last five minutes.

“Holy shit Hailee. You actually let him do anal with that thing.”

“Of course.”

“How does it fit?”

“Fantastically,” Hailee said as she was now rubbing her clit with her hand while I continued to pump in and out of her ass. Bailee watched dumbfounded as me and Hailee enjoyed ourselves. It took another minute for Hailee to get herself to cum. Once I heard her let out a familiar sound of her orgasm, I pulled out of her ass. Unfortunately, by the time I had pulled out, I was beyond the point of no return and my cock immediately began to shoot off. The first two shot hit Hailee's ass and when I turned a little bit I fired the rest upon Bailee’s breast and stomach, with one hard shot hitting her on the chin.

Hailee had collapsed onto her stomach after she came and after I finished exploding all over Bailee I got on the bed and laid next to Hailee. Bailee rested by laying on her back on the other side of Hailee, her fingers playing a bit with the man seed that covered her torso.

“So Bailee, did you enjoy yourself?” Hailee asked after a couple of minutes.

“Oh yeah,” she responded

“Did my boyfriend give you the fucking you came here for?”


“Good. Now, get dressed and get out.”


“Huh?” I was even taken off guard by Hailee’s rudeness.

“Tomorrow is Valentine’s Day and I don’t want to wake up with another woman in my man’s bed,” Hailee told her as she wrapped her arms around me. Hailee apologizes for coming off as rude but still made sure Bailee left before we went to sleep.

The next day was a cool rainy day in Pasadena and since we had no real plans, Hailee and I spent most of Valentine’s Day in bed with one another. We talked, watched Netflix, got some Postmates, and of course, had some really really good sex. We spent a lot of time together over the next month. During that time we went at it like horny teenagers on Viagra. We made our first public appearance together at the Vanity Fair Oscar party, though I had her walk down the carpet in front of the photographers by herself. It wasn’t until mid-March that we spent any real prolong time apart.

I went to the South by Southwest in Austin to put on a screening for my film. It also turned out that at the same time I was scheduled to come back to LA, Hailee was flying off to Japan for a premiere of Bumblebee. It was while I was at SXSW that the openness of our relationship was first acted on. Becky G ended up not making the trip so she was not there to give me the “proper thanking” she had promised, and I did not hook up with VJ or Jane while there either. It was not until one of my last days in Austin than anything happened. At one of the parties, I ran into both Kelli Berglund and Olivia Holt who were both there to promote their shows. It was while we were all hanging out and talking that we decided to Skype Hailee. The Skype session started innocent enough, but I am not even sure how it ended the way it did, with Hailee masturbating while she watches Liv & Kelli giving me a duel blowjob in a bathroom stall.