Turning Fantasy Into Reality
Starring Bailee MadisonCodes: MF, Oral, Facial,
Written by MiamiLyfe
Disclaimer: The following is completely fiction, and it is nothing but pure fantasy.
I had been fucking Peyton for over a year. There was nothing serious going on between us, we were just friends who after drunkenly hooking up one night after a friend's birthday party, ended up becoming fuck buddies. She is a bit of a butterface, truth be told, especially compared to some of her friends. However, she did have a really nice body and was a good fuck. All that said, this is not a story about Peyton. This is a story about how I finally hooked up with one of her friends, Bailee Madison.
The story starts a few months into our fuckbuddy relationship. We were laying in bed having hooked up last night and just had a morning quickly. She was scrolling through her phone looking at her morning notifications on her phone. When she switched over to Instagram she started asking me what I thought about some of her friends. Being a nice guy, I was not about to tell the woman lying nude next to me that I think her friends were hot and possibly hotter than her. So I just said things like ‘she’s alright’, ‘she’s pretty’, and ‘she’s cute’. Eventually, Peyton got tired of my noncommittal answers, so her way of finding out the truth was to scroll through her friends’ or other women’s Instagram feed in one hand while stroking my dick in her other hand. This became a regular thing for us. She jerked me hard while having me look at her friends’ pictures before we would fuck again.
“You have a big thing for Bailee,” Peyton eventually said one day, employing a little double entendre as she stroked my cock. And she was right. While other celebrities like Hailee Steinfeld or Emma Watson really got me going, of Peyton’s friends, Bailee was the one who turned me on the most. She liked how quick I got rock hard as she went through Bailee’s pictures, or how sometimes my dick jumped in her hand when going through some of her dancing TikTok videos.
After several months of this, things began to escalate. One day after making the transition from stroking my dick while showing me pictures of Bailee to the two of us having sex, she had me get on top of her and she said, “Fuck me like I’m Bailee.” I questioned her and she told me again that she wanted me to fuck her like she was her friend. So I did. And then this became a regular thing. Occasionally she’d change it up to a different friend, but Bailee was the one she brought up most often.
Things got taken up another notch when one night after a preliminary round of sex, Peyton went to her bag, pulled something out, and went to the bathroom. When she came back to the bedroom she had on a wavy brunette wig that had hair that reached down to her shoulder blades.
“Peyton, what are you doing?” I questioned her.
“Peyton isn’t here, I’m Bailee,” she replied. It was at that moment that I realized that the wig did match her friend’s natural hair.
“Peyton, I…”
“Call me Bailee,” she insisted. I told her that while I could see her face and could see she wasn’t Bailee I couldn’t call her someone else's name. Her solution to that was to lay down on her stomach on the bed and have me take her prone bone. While her ass was a bit thicker and her shoulders a little broader than what I expected Bailee would look like, with her hair the way it was, I had less issue pretending she was her friend and calling her Bailee as I slid my dick into her. Soon I had blocked from my mind who I was actually fucking and started to act like it was Bailee I was fucking. I ended up pumping two loads into Peyton’s womb and delivering her three orgasms including out that caused her pussy to gush so much it soaked through the sheets and down into the mattress. After that night, I came away with one thought and one goal, I need to sick my dick into the real Bailee Madison.
While I knew it would not be something easy to do. Bailee was not one to just jump into bed with anyone, it was also not impossible. I was not just some random guy in Iowa pinning for a celebrity I’d never meet. Bailee and I did already know each other, I even had her phone number already saved to my phone. Through Peyton, we’d hung out several times at different parties and events. We got along well and enjoyed talking with one another. We also occasionally saw each other without Peyton around since we both went to the same gym. I also had more things going for me, and that was her being close friends with someone I was fucking and who seemed to enjoy having sex with me, so no doubt Peyton had told Bailee several stories about our sexual encounters in the past. After I made the decision that I needed to bed Bailee, I found myself becoming more flirtatious with her whenever we talked, and I also started to adjust my schedule so that my gym schedule started to overlap with Bailee’s gym time.
After a few weeks, Peyton noticed the change in how I acted and spoke to Bailee. When she asked me directly if I was trying to sleep with her friend, I told her yes. Peyton gave it her blessing (though had she not, I was not going to stop my pursuit), and just made me promise her that if I did succeed that I would have to tell her all the details. I agreed to that. Peyton and I continued to bang from time to time, while I continued to flirt with her friend. My sudden flirtation caught Bailee off guard at first, but after about six weeks Bailee began to flirt back at me.
We flirted back and forth for a few weeks before I finally decided to make a move on her. It was Saturday morning, and I was at the gym at the same time as Bailee. I was working out on my own while she was working with a personal trainer. We waved when we saw each other from across the gym, but could not talk. I did my best to act like I was not paying attention to her while also adjusting my workout so that I tried to stay in her peripheral vision. I tried not to look over at her too much, but it’s not the easiest thing to not check out a woman you like when she is stretching and bending over dressed nothing in spandex and a sports bra.
When I knew her workout was getting close to wrapping up, I finished what was left in my water bottle and went over to the water fountain by the locker room entrances. I took a long slow drink from the fountain and then began to fill up my bottle. Thankfully, just as my bottle was close to full was when Bailee was finally making her way to the locker room. She stopped and we made some brief small talk before I asked her what she was doing after she left the gym.
“I don’t know. Probably stop somewhere and get something to eat. I didn’t have time for breakfast before coming here.”
“I could eat too, wanna get something together?”
“Umm, yeah, sure. That’d be fun.”
“Cool. I kind of stink though, so maybe we should just stop off at my place and shower before we go eat.”
“Are you asking me to shower with you?” she said with a little bit of a laugh.
“I was thinking we would go to my place since I live just a few blocks away, and we’d take turns showering, but if you want to shower together I’d be good with that.” She blushed at that comment, and I also saw her eyes give me a quick once over.
“Maybe we can just take tuns today.”
“Okay. Let me just grab my stuff out of the locker and I can meet you outside in like five minutes?”
“Sounds good,” she agreed before heading into the Women’s locker room.
Bailee met me in the parking lot and she followed me in her car over to my apartment complex. After taking a visitor’s pass out of my glovebox and putting it under her windshield, the A Week Away actress walked with me up to my place. I asked her if she minded if I showered first, but she didn’t. I told her that if she was really hungry there was some fruit in my fridge she could snack on while I showered.
Once I made sure she was settled I headed toward the bathroom. The bathroom in my one-bedroom apartment had two doors to it. One entrance by the kitchen, and the other through the master bedroom. I entered the bathroom through my bedroom. I could see the door by the kitchen mostly shut, but still open by about 2 or 3 inches. Rather than shut it, I purposely ignored it and stripped off my clothes. Once naked, I took my time before getting in the shower. I shaved my face and brushed my teeth before turning on the shower. While in the glass shower stall, I angled my body so that if hypothetically someone were to look into the bathroom through the opening in the door, they could get a clear view of my dick. I even worked extra time scrubbing my dick and balls, and also gave my shaft a few extra tugs. I tied to keep my eye on the door, but I did not see any movement by it.
After showering, I turned off the water and toweled myself down. I looked to the door to see if it had opened up any or closed, but the best I could tell it was still open as much as I left it. Once I had dried off, I took my cock and stroked it. I did not want to get fully hard, but I wanted to plump my cock enough to have a noticeable bulge once I wrapped my towel around my waist. Walking out of the bathroom, I went looking for Bailee. It did not take long for me to find her. She was casually standing outside on my balcony by my bedroom widow tapping away on her phone. It could have just been a coincidence she was standing there, or it could have been she was hoping for a peek of me getting changed.
“The shower is all yours, and I left a spare towel out for you,” I told her as I stepped out onto the balcony.
“Okay, thanks,” she said as she looked up at me from her phone. At first, her eyes looked up to my face when she heard my voice. Then I watched as her eyes traveled down my body as she realized that I was dressed in just a towel, with them stopping when they got down to the purposeful bulge at the front of my towel.
“Oh, umm, wow. Aren’t you afraid of someone seeing you like that?”
“Like what?” I asked as she tried to look away from the towel, but her eyes kept drifting back.
“Dressed only in a towel while out in the open.”
“Why should I? We’re on the 7th floor and there is not another high rise for a few blocks, so not like anyone can look down on us. And with the balcony wall being stucco instead of glass, no one can see what’s going on below my waist. Heck, I can take this off,” I said as I pulled off my towel, exposing my half-hard dick to Bailee, “and no matter who is looking up here the only people who know that I am naked are you and me.”
“Yeah, you are naked. Wow. I, uh, I should take that shower now,” she said as she walked by me. I had her flustered for sure. But not in a way where she was bothered by my actions. No, if she was bothered by me dropping off my towel in front of her, she would have gotten her stuff and left my place. She would not have told me that she was going to go to another room in my apartment to strip out of her clothes. She also would not have turned her head back around and gotten one more long good look at my cock which had become fully erect as we talked and I watched her eyes keep looking down at it. Though she was not above a little leasing of her own. She pulled off her sports bra just before stepping into my bathroom, giving me a view of her fully exposed back for about a second.
I picked up my towel off the ground, but rather than wrapping it around my waist I just slung it over my shoulder. I went to my bedroom and picked up my phone and did a little bit of scrolling through my notifications. As I did that I heard the water begin to run. Looking up to the bathroom, I noticed something. The door was not fully shut. While not as brazen as when I did it, leaving it open by a few inches, the door was not only open by a small crack. Not even really enough to look through, but enough that I barely had to put any pressure on the door to open it up. Pushing the door open and stepping in, I could see Bailee through the glass door. Her back was to me. Pulling the towel off my shoulder and putting it down on the counter, I then opened the shower door and stepped in behind her.
“What? What do you think you’re doing?” Bailee asked as she looked over her shoulder at me. While she wrapped an arm around her chest to hide her breasts from me, the slight smile on her face when she asked what I was doing let me know I wasn’t upset by my joining her.
“You left the door open and it looked like you could use some help washing your back. Besides you were the one who suggested us showering together back at the gym,” I told her. I then reached around Bailee and grabbed the loofa, and held it out in front of her.
“That wasn’t a suggestion, and the door was not opened enough for you to have seen me,” she said admitting that she knew she left the door partly open. As she spoke, she took the body wash bottle and squeezed some onto the loofa.
“I never said it was,” I replied. I then began washing her back. Starting by rubbing her shoulders. As I scrubbed her back up and down with the loofa, I also made sure to poke and bump her with my hard-on, before eventually rubbing it up and down along her ass crack. I scrubbed her back using the loofa for several minutes, though I did also include my off-hand when washing her ass, making sure the soap was extra sudsy by the time I was done with that. All the while, Bailee never verbally said whether she was enjoying me being there with her, but her body’s response let me know she did. From the way she bit her lip each time she looked back over her shoulder at me, the way she would occasionally push her ass back into my dick while I pushed it against her, to also how now and then I could hear a soft barley audible moan escape pass her lips.
“Alright,” I said stepping away from her, “time to turn around and rinse off.” She hesitated to move at first, which worked perfectly for me, as once she finally did turn around I had gotten a chance to drop to my knees. When she was facing me, I did not give her any time to react. I gave myself no time to take in the view of her womanhood with her saved lips and a patch of brunette hair on top before I lunged my face forward and buried my tongue into her snatch.
“Brian! What the heck!” Bailee shouted with surprise. By I didn’t respond, other than continuing to eat her out like I was a death row inmate and her pussy was my final meal. It didn’t take her long to change her tune from surprise to pleasure. “Oh! Oh, yes. Give me your tongue. Peyton said you were good at this.”
She moved backward and leaned against the wall while pushing her hips out to my face. She put one hand on the back of my head, and when I looked up I could see her other hand was squeezing her breast. “Mmmmm… yes, right there!” she moaned loudly. I worked my tongue the best that I could and sucked on her clit. I was motivated to get her off. I was not trying to tease her or edge her or all, I wanted to get her pussy to pop as soon as I could. And it did not take that much longer.
“Oh! Oh wow, I’m almost there! Keep going,” Bailee pleaded. It’d been only a few minutes since she put her hand on my head and now she gripping the hair on my head while she let out a trembling moan as she came. One of her legs buckled, but I had my arms wrapped around her thighs and that helped keep her upright.
Once she had regained the strength in her legs and found her balance, I got up off the floor but I did not step away from her. Once I was standing, our faces were just inches from one another the shaft of my hard dick rested up against her the hot leaking folds of her pussy.
“So, how was that?”
“Peyton said you had a nice tongue, I guess she was not lying.”
“Nope, and I didn’t even give you the treatment I give her. Normally, I like to tease and edge to the point where Peyton is pleading with me to make her orgasm.”
“That sounds really good, but I’m not sure we should do anything more. I mean, Peyton is my friend, and…”
“And she doesn’t care if we fool around or not. Trust me.”
“I don’t think I can trust you when I can literally feel your penis pulsating between my legs. You’d probably say anything for a chance to stick that thing in me.”
“You might not be wrong about that, but I’m not lying. We can even call her and you can ask her yourself.”
“Seriously?” Bailee questioned me.
“Yeah. Let’s dry off and then you can call her.” Bailee turned off the water and we stepped out of the shower. I grabbed the towel I had left out for her and began rubbing and patting dry just about every square inch of her body. Once she was dry, I toweled myself off quickly before we headed into my bedroom. I told the PLL Original Sin actress to lay down on my bed as I got my phone. All I could think was, ‘This bitch better answer’ as I tapped on Peyton’s name in my contacts and handed my phone over to Bailee.
“Hi! No, it’s Bailee… he gave me his phone,” I listened in to her conversation with Peyton, but as they spoke, I got on the bed down by her legs.
“I’m at his place, and I have to ask you something… I, yes. How did you know?” Bailee continued to converse as I picked up one of her long legs and starting at her calf muscle, began kissing my way up the inside of her leg.
“What do you mean you two have talked about this? Did you plan this?” After that, Bailee went silent for a while, listening in as Peyton spoke. As she did that, I worked my way all the way up her legs so my face was right back between her thighs. Rather than diving right back into he pussy, I instead blew on her clit and then moved my body up hers. I went to her breasts and quickly took one tit into one hand and began kissing the other one.
“Uggghhh…” Bailee moaned. I was not close enough that hear exactly what Peyton was saying, but I could hear her muffled voice. She asked some kind of question after Bailee’s moaned. “That was nothing. I’m fine,” Bailee said trying to brush off the fact that she accidentally moaned into the phone. Again I could hear Peyton’s voice. “He’s playing with my boobs….yes it feels good, “ Peyton began talking again.
“She wants to talk to you,” Bailee said. This time she was addressing me and handing me back my phone. I took it from her and sat up.
“Hello,” I spoke into the phone.
“I don’t know how you got her into bed, but you better make the most of it because I’m not sure she’ll let you do it again.”
“You never know,” I replied, once again purposely being vague.
“Whatever. Just saying, if I were you, I’d fuck her raw.”
“That’s the plan,” I said and then hung up on her. Maybe she had more to say, but I didn’t care. I had Bailee laying naked on my bed, and that was the only thing I wanted to focus on.
“So did Peyton give you the answer you were looking for?” I asked Bailee.
“Yes,” she replied with a big smile.
“So what now?”
“Put it in me. I want you inside me.” I was very excited to hear her say that. I moved on top of Bailee, and for the first time, I kissed her lips. Bailee eagerly kissed me back. She was quick to push her tongue into my mouth. As we kissed, I reached between our bodies and began positioning my dick. I rubbed the tip against her leaking wet folds several times. I then pulled away from her kiss, so I could look down at her face as I pushed my dick inside of her.
I watched as Bailee gasped when she felt my dick separating her lower lips and begin to push inside of her. I moved slowly, sliding my dick inside of her. “You’re thick,” she said when I was just about halfway in.
“Not too thick I hope,” I said.
“No, just the right amount, you feel so good,” she said. With that, I continued to push inside of her, until I was fully in. I then paused when I was buried to the root inside of her. Once I was sure she was feeling good and acclimated to my dick size, we slowly began fucking. She felt amazing. Both wet and tight, and listening to her soft moans as I began sliding in and out of her.
“Oh wow, I can’t believe we’re doing this. I can’t believe we're, actually having sex,” Bailee said, practically taking the words out of my mouth.
“You sound as though you might have thought about this before.”
“Maybe,” the former Fosters actress answered.
“Hope I can make those fantasies come true.”
“We still have a long way to go to do that, but so far so good,” she said. She then wrapped her hand behind my head and brought my face down to her’s so I could kiss her once again as we continued to have sex in the missionary position. I did my best to keep up the tempo to try to please her while not over-exciting myself. When I did feel things in balls start churning, I suggested that Bailee get on top and ride me. She did so happily, and it gave me enough time as we moved around the bed to settle my cock back down.
Bailee once on top rode me like a mad woman. She rode my dick like she had somewhere she needed to be and she needed to get there fast. As she rocked her hips, her soft pillowy tits shook and wobbled all over the place. Even causing her to use an arm to keep them from bouncing so much. I quickly volunteered to help her out and replace her arm with my two hands on her breasts. She was only riding me for a matter of minutes before she came on my dick. I felt her pussy squeeze down on my dick and her juices begin dripping down onto my balls. Even after she came, she still continued riding me, though at a reduced speed and more methodical tempo.
“Did you ever think about me?” Bailee asked as she slowly rocked her body.
“What?” I asked with her question catching me off guard.
“Did you ever think or fantasize about me?”
“Of, course I did.”
“Just in general or while you were with Peyton?”
“Both,” I told her the truth. Though I did not tell her about the part where her friend wanted me to pretend that she was Bailee while he had sex.
“Really?” Bailee seemed excited by my answer.
“Last time I jerked off thinking about you was Monday. We were at the gym, I was on the elliptical and I had a clear view of you doing squats in the mirror. You were facing away from me, so I just kept watching you bend down and stick your ass out in the yoga pants. I came home that morning and splattered the side of my shower with cum after jerking off while replaying that vision in my head.”
“I didn’t know I had that kind of effect on you,”
“Don’t know what to tell you, you’re a very cute and sexy woman Bails.”
“So in the vision in your head while you were touching yourself, was I still in my yoga pants, or did it look something like this.” Bailee then got up on her feet, turned around, and squatted right down on my dick. She even put her arms out and leaned forward so that she could really pop her ass out at me as she began riding me reverse cowgirl. This time it was not so much a grind as before, but Bailee was actually bouncing up and down on my cock. After a minute or two, she looked back at me over her shoulder, and asked “So, which was it?”
“In the shower, it was just you in your yoga pants, but this is way better,” I told her. I held on to her hips as she bounced on my cock. She rode me like this until once again, I was getting close to the edge, but again I was not willing to bust my nut just yet. Instead, I had her turn around, get on her knees and put her arms up on the headboard. I got on my knees behind her, and after teasing her womanhood with my cock for a bit I reentered her and took her doggystyle on the bed. As we fucked I again put one hand on her tit, while I used the other to rub her clit while my dick pistoned in and out of her.
Bailee was the first of us to climax. She came hard on my dick and after feeling her clamp down on my dick and watching her body shudder in ecstasy, I could feel myself closing in on my own finish. I kept humping the 22-year-old actress until I was at the point I knew I could not hold out much longer. “Shit Bailee, I am going to cum,” I warned her.
“Do it, give it to me,” she moaned
“Where? Where do you want it?”
“Anywhere. Where ever you want. I don’t care.”
“Let me give you a facial,”
“Yeah? You want to shoot your cum onto my face?”
“More than anything.”
“Okay, you can do it,” Bailee agreed. I pulled out of her and jumped off the bed. I had Bailee lie on her back with her head hanging off the bed. I began stroking my dick, and she just looked at me with a big smile on her face. My dick was just inches in front of her and her eyes bounced back and forth between my face and the tip of my cock. It was while I made eye contact with her and she decided to slowly and seductively licking her lips with her tongue that I lost control. My cock began to erupt and shot jizz over the face of the beautiful woman in front of me. All the edging I had done up to this point paid off as I delivered one of the largest loads I had in quite a long time. Bailee could only laugh as she felt my dick continue to fire off.
“Oh my god, that was so much,” Bailee laughed when I finally finished. “I feel like it’s covering my face.”
“You want to see how much there is?”
“Sure,” she said as she rolled over onto her stomach and sat up. I picked up my discarded phone off of the bed and snapped a picture of her face glazed with my cum. I then showed her the picture. “Oh my gosh, I look like a Krispy Kreme donut,” she joked.
“Mind if I take one more?” I asked, referring to taking another picture.
“Yeah I guess so,” she replied. This time she posed for the picture with a big broad smile, and I took a step back, making sure this time I had her breasts framed in the picture. I wanted to make sure I could revisit the sight of them whenever I wanted in the future. After two more pictures, Bailee ran to the bathroom to clean her face and I got back onto the bed. I took a look at all the pictures I had just taken while I waited for her to finish up in the bathroom.
“Oh wow. You’re still hard?” Bailee said as she bounded back into the room, face freshly washed, and looked at me on the be lightly touching my awaiting erection. Her voice made it seem like she was generally surprised I could still be hard
“That surprises you?” I replied, perplexed by her surprise.
“It usually takes Blake a while to recover on his own or I need to suck on it for a bit to get him hard again.”
“That’s disappointing to hear, I feel kind of bad for you. But if you felt the need to blow me a bit just to make sure I am fully hard, you’re more than welcome to.”
“Well, I guess it can’t hurt to be absolutely sure you are completely hard,” she said cheekily as she climbed back up on the bed. I sat up and put another pillow behind my head as Bailee got on her knees between my spread legs. She took hold of my shaft in one of her hands and, with a light touch, twisted her grip while also slowly stroking me up and down. She looked me straight in the eye as she did so, and a smile crept across her face as she began to bend down. She even gave me a wink before she puckered up and kissed the tip of my dick. She gave it a few more kisses, before snaking her tongue out and swiveling it around my cock head. She maintained eye contact with me the entire time, up until she finally opened her mouth wide and took half my dick into her mouth.
At first, she focused mostly on using her mouth around the tip and continuing to jack my shaft with her hand. After another minute, she pulled her hand away and only used her mouth on my manhood. She bobbed her head up and down my dick while her eyes looked up into mine. This was all mostly for show than it was to really get me to cum, and I was fine with that. I did not want to finish in her mouth, and she looked damn good with the way she was going down on me.
“Bailee, that’s…” I was going to tell her that what she was doing felt good and I was ready for more, but she interrupted me.
“You want to fuck some more?”
“Hell, yes.”
“How do you want me?” she asked, and then began slowly and seductively kissing along the side of my shaft.
“Do you what probe bone is?” I asked but she shook her head no. “I just want you to lie flat on your stomach.”
“Oh, okay, I think I know what you mean now.”
I rolled away from the center of the bed and she replaced me in that spot, laying down on her stomach. I took a pillow and placed it under her to lift up her hips a bit. I then when to my bottom nightstand drawer and pulled out a surprise for her.
“Whose’s that?” she asked when she saw the small vibrator in my hand.
“Peyton left it here one night. Don’t worry, I washed it,” I lied. Not about having washed it, I lied about who it belonged to. The truth was the vibrator was mine. I did not have it to use on myself, I bought it to have and use on women when they stayed over. I found that it can take foreplay to the next level, and at a time can be great to incorporate while having sex.
“Okay,” she said, unsure of what I was planning.
“Trust me, you’ll enjoy this.” Moving back behind Bailee, I turned on the vibrator to a medium setting and had her raise her hips. I think she was expecting me to put it inside of her. Instead, I placed it on the pillow and had Bailee lay back down.
“OH!” she exclaimed, as now she was laying on top of the vibrator with it pressing right up against her clit. I then took hold of her hips and moved my body until I was at the perfect angle and sank my manhood into her. For a split second, I had the wrong angle, and my dick slipped upward and my cock head pressed up against her backdoor. I quickly felt her cheeks clench up when that happened. But she relaxed once again when I adjusted and my dick found its correct target.
With my member sheath inside of her and the vibrator pressing against her love button, it did not even take a minute before Bailee was moaning as loudly as ever, and she had a death grip on the bed sheets. For me, this was the moment I was making my fantasy come true. While normally I might prefer to look at someone as pretty as Bailee in the face as we had sex, and while she currently had her hair dyed blonde instead of her natural brunette, this was the moment I had been waiting for ever since Peyton had laid on my bed in that wig. And once I heard her moaning and knew she was comfortable doing the position we were doing, that was it for me. My rational brain switched off and my animalistic brain kicked in. I began thrusting as harder and faster than I had at any point thus far. Her ass clapped each time I thrust down into her, and Bailee let out a pleasured grunt each time I bottom out into her.
“Wow, that is something,” I said looking at my load streaking across her butt and lower back.
“I’m starting to think you have a thing for seeing you cum on me,” she said as she looked back over her shoulder at me.
“I’d question the heterosexuality of any guy who doesn’t like the view that I am seeing. Once again, I picked up my phone off the bed and snapped some quick photos. These had Bailee laying on her stomach with her feet kicked up in the air, her looking back at me with a big smile, and of course, my jizz clearly painted on her ass.
I then laid back down on the bed next to Bailee, and she rolled over onto her back. I handed her the phone and showed her the picture that I took. “You’re right, I do look nice in these. You know you can’t show them to anyone else, right?”
“Of course not. Those are just for me, and you if you want copies,” I told her. She did ask for copies of the pictures, and we continued to lay in bed making small talk for a little longer.
“I think we missed lunch,” Bailee said as she looked at the clock while laying next to me in bed. She was right, it was now late afternoon, and probably closer to early dinner than lunchtime. “Maybe I should get going,” she said shyly.
“You don’t have to. Do you have anything going on tonight that you have to leave for?”
“I mean, no, but…”
“Okay, well, I promised you lunch, and since neither of us has any plans for tight, why don’t I just order us a pizza and we can just hang out a little bit longer.”
“Okay,” she said with a smile spreading across her face, not able to hide the fact that she was happy that I wanted her to stay longer. I then picked up my phone and began to place an order, but rather than have the order set to come ASAP, I took a risk. Unbeknownst to her, I set a delivery time for a little over an hour from when it was placed.
“How long?” She asked as I put my phone down.
“Not too long, but we have some time to kill,” I informed her, purposely being intentionally vague. I then rolled over onto my side and faced her. “So I want to make a bet.”
“What kind of bet?” she asked excitedly.
“Since neither of us has anything going on tonight, the bet is that I am about to go down on you again. If I get you off twice before the pizza arrives, you stay here this evening. If I fail to get you off twice you can leave whenever you want. You can even take the whole pizza box right from the delivery person’s hands and walk out the door.”
“Seriously?” she asked, giggling at my proposal.
“I’m completely serious.”
“Okay, sure,” she said still kind of giggling. “Sounds like I win no matter what.” I too believed this to be a nearly no-lose situation, though I had stacked the deck in my own favor.
It took just over 90 minutes for the pizza to arrive, and I ate her pussy out for three orgasms and she sucked a load out of my dick in that time. Having won the bet, she did stay once the food arrived. We ended up watching the latest big movie on Netflix as we ate, and once it was over the two of us went back to my bedroom and we ended up fucking some more. This time there was no stopping me from finishing off inside her velvety pussy. And then we did it again. And again, until we ended up both passing out in blissful exhaustion. And then we picked it back up in the early morning. When we finally stopped fucking, I had done exactly what Peyton had said and fucked her raw. Bailee said her pussy was feeling kind of sore, and my balls were so drained that on my final orgasm though I felt the sensation of cumming, nothing came out.
“Do you think we can do this again?” she asked as she got dressed and ready to leave. “
“I sure as fuck hope so, but that’s up to you.”
“What about Peyton?”
“What about her?” I asked.
“Do you think she’d mind?”
“I don’t know what she’s told you about us, but there’s nothing really between us. We’re friends and we have sex, but it’s just about having fun and convenience. That’s it.”
“That’s it?”
“Yeah. And don’t tell her this, but while she has a good body, you are so so much prettier than she is. And I much rather do this again with you than her. ”
“Thanks,” Bailee said with a blushing smile. “So if I were to text you, some time…”
“I’d happily hang out as just friends, but if you text me about doing something like what we did last night, I could be in the middle of fucking Peyton and I would stop, get dressed, and head out to meet up with you.”
“Really? Hmm.., I just might need to test that statement at some point,” Bailee said, assuming I was exaggerating in my answer.
“Can’t wait,” I told her, just hoping she would try and call my bluff.
Topic: Turning Fantasy Into Reality with Bailee Madison (Read 3340 times)