Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/12282777. Rating: Explicit Archive Warning: Underage Category: F/F Fandom: Hannah_Montana_(TV) Relationship: Miley_Stewart/Lilly_Truscott Character: Miley_Stewart, Lilly_Truscott, Oliver_Oken Additional Tags: Futanari, Shemale, Girl_Peen, G!P Stats: Published: 2013-10-13 Updated: 2014-05-18 Chapters: 5/? Words: 5129 ****** A Revisited Dilema ****** by UnsungDude4 Summary Another story from my Fanfiction.net account. Probably gonna finish it too. It's a reworking of a story from Yeah-baby91 on there, who started the story, but didn't continue it after the first 3 chapters, so I did. ***** Ch. 1 ***** 'Oh God! Yes! Mm! Just a little more….. Oh! God!' I kept stroking myself. Oh, hey I'm Lilly Truscott and… Umm yeah I'm masturbating in my best friend's restroom. Hey, no, I'm not a pervert… okay maybe just a little, but let me tell you why I'm here right now with this strong, hard 10 inch problem first. What? Oh. Yeah I have a dick, got a problem with that!? Yeah, that's what I thought. Okay let's start with this story. Everything start yesterday. If I'm not wrong, around 6:29 pm when this beautiful gorgeous brunette, my best friend Miley, called me. I was at the beach with Oliver … well not exactly with Oliver, more like just watching that he doesn't end up with a girl's foot on his face. Well, right now I was with this pretty blonde girl, *wink*, chatting and I got her number, email, and Facebook too. Oh I'm so good. Oliver should learn something. "So tell me do you have…." My phone rang in that moment, so I took it out of one of the bags of my board shorts and answered it at the same time. I gave the blonde girl a signal for her to wait a moment. "Hello?" "Lils, it's Miley. Can you come over please?" she was crying and I was starting to get worried. "Where are you? I'm on my way," I got up and start heading to my car almost running , but I remembered the blonde chick, the one whom I don't remember the name of. I looked to her direction, made a phone signal with my hand, lipped her a 'call you later,' and winked. "I'm at the Tipton Hotel," she told me in a little whisper. What is she doing at the Tipton? "What are you doing there?" "I'll tell you when you're here, please Lilly don't take too long." "Okay, I'll be there as soon as possible," I got in my car and drove to the Tipton at maximum speed. I got there in about 6 minutes. Miley was out by the door with tears all over her face and red puffy eyes. I parked my car, got out, and headed over to her. Oh I'm going to kill the bastard who did this to her. I hugged her and she hid her face in my neck and cried again. "Do you want to go to a place a little more private, Miles?" she didn't answer, just a nod. I took her hand and lead her to my car (the one she totally loves, my black 911 turbo Porsche). We went directly to her place, a really nice condo with a nice view to the ocean. I parked my baby next to her car and got out, then I opened the door for her. Yup, I'm a gentleman. When we were at her room, she was crying so hard that I almost start crying with her, but no. I have to be strong for her. "Miley, what happened?" she looks at me with her big blue eyes, filled with so much hurt and fear. I took a gulp for what she was going to say to me. "Jake… invited me to the movies… and we didn't make it" "What do you mean?" "He took me to his hotel room because he forgot his wallet, or something like that and tried to take advantage of me." By this time, she was bursting in tears, and I was boiling in anger. Jake is a dead actor. I hugged Miley, as we lay on her bed. In less than an hour, Miley was sleeping peacefully with her head on my shoulder. After a little more time, I went to sleep too. Actually, in the morning, was the real problem. Miley had her leg on my cock, unconsciously rubbing it and making Lilly-bear a little excited. "Mmm… Lilly…" I started to hyperventilate. Miley doesn't know about Lilly-bear. "Yeah… Mm…. Lilly…please." She's having a wet dream? Or am I having a wet dream about Miley having a wet dream? At that moment, my dick started to get really, really hard. I got very nervous and tried to get out of Miley's grip, but her leg brushed the tip of my dick and it felt to damn good, that I almost came, but give me credit. I didn't. After getting out of Miley's arms, I made my way to Miley's restroom. I took off my clothes and started the water, a hot shower will make me good. When the water was perfect, I took off my boxers and got down under the spraying water. It felt good, then I looked down to my standing, proud member and with my right arm took hold of 'him.' Up and down, up and down, up rub the head down. I went into a complete trance and started imagining Miley, naked in the rain. "Yeah baby," I whispered and moaned with my hand still doing its job. I felt my orgasm starting to form. Oh God! Yes! Mm! Just a little more….. Oh! God! ... PEACE ... ***** Ch. 2 ***** Ring… ring…  A cellphone started ringing. Miley Stewart started to wake up, groaning and frustrated, she had a headache. She was really confused. She just had the weirdest dream. She had never had a sex dream, much less with her best friend. Ring… ring… She start looking for her phone, damn thing. Finally, she found it on the table next to the bed. "Hey Ollie, What's up?" she answered while getting up off the bed and headed toward her closet to see what's she going to wear. "No, I don't know where she is," she took off her clothes until she was just in her underwear, got a towel, and made her way to the bathroom. "Did you already call her phone? No mine?" she laughed and uncliped her bra then she threw it to the floor. "Of course you haven't. Yes she was with me yesterday, but I don't know where she is right now," she entered the bathroom and stopped abruptly. The bathroom slide doors were crystal clear, so she saw everything. Lilly felt like someone's eyes were on her, so she opened her eyes and looked to the direction of the presence. There it was, Miley Stewart, looking at her with surprise and her mouth hanging open. Lilly tried to make a move, but that was a bad idea. She moved her arm and, in effect, she moved her hand, making her orgasm. She had been really close to the edge when Miley entered the bathroom. "Oh, shit" Lilly whisper. Miley looked like a fish out of the water, with her mouth open, but not making any sound. She started moving back to the door without moving her eyes from Lilly. "Miley. I… Me… Oh God Miles," Lilly took the towel she had on the top of the toilet seat and wrapped it around her mid-section, so her member wasn't exposed. "Oh, God," she said, getting ready to run after Miley, who ran out of the bathroom, leaving Lilly feeling hopeless. 'She's going to hate me or…. castrate me.' After the last thought, Lilly shuddered in fear. 'Okay Truscott, she was going to find out one way or another, grow some balls… he he, I already have so… and explain to her everything.' After a moment, she got a brave. She went out to go to talk to Miley and tell her about Lilly-bear, and hoped Miley would not kick her out of the condo, and of her life. Outside the bathroom door, Miley was seated on the edge of the bed, her face as red as a tomato. Miley heard the bathroom door open and immediately looked toward it. "Miles… can I talk to you?" Lilly asked, a little shy. Miley got up off the bed and walked over to Lilly. "PLEASE DON'T CASTRATE ME!" "Paranoid best friend, say 'what?'" Miley looked at Lilly with a confuse face. "If I haven't castrated you in what 11 years, why would I do it now?" "What?" Lilly's mouth dropped. She didn't expect that answer. "What, 'what?'" "You knew that I had penis?" "Well, yeah. I knew you had one of those." Miley said, it as if it was the most normal thing in the world to say. "First of all, how did you…umm…. know that I have one?" Lilly asked really confused. "Ah come on Lilly. We've been friends for 11 years, how could I not know? We were teenagers and had sleepovers…" Lilly still looked confused. "Okay, one morning when we were fourteen, something was poking me in my sleep. It was your cock," Lilly's jaw dropped. "I saw it, when I pulled down your sleep pants and saw it for myself. And do you remember that night that we suppose to make peace with Joanie? I kind of saw you with her making 'peace,' I guess." -Flashback Miley's POV- "I was sleeping peacefully, well as peacefully as someone could sleep when they have one of their enemies sleeping at their home. I felt like something was missing, like my personal warmer wasn't there and actually, it wasn't. I started looking for you, 'Maybe she's in the bathroom, or in the kitchen,' I thought. "Oh! Shit! Oh!" 'Okay what was that? Sounds like someone was in pain, or something. Oh God! What if it's Lilly?' I got up off my bed and walked out of my room, looking for my you. When I got to one of the guest rooms, I heard strange noises again. It sounded like some kind of animal. I also heard something hit the wall repeatedly. "Fuck, Lilly!" I heard Joanie half-groan, half-scream. I started to get a little curious. 'What are they doing?' I thought. The door was a little open so I took a look inside and damn what I saw was something else. Joanie was sitting on someone else, totally naked and moving up and down, moaning and groaning. I didn't see who the other person was, but I believed that it was you. That would explain why Joanie kept calling out your name. I think your dominant instinct kicked in, because you flipped Joanie until you were on top and start thrusting, fast and hard. I saw how you tensed and Joanie arched her back, making a weird noise. When everything was finished, you guys were breathing hard." - End of flashback- Lilly was in total shock. Miley never asked anything or said anything about it. And the Joanie thing was just too much. The blonde thought Miley had just been sleeping. "Why didn't you tell me anything?" Or fucking punch me! I was fucking my best boyfriend's girlfriend! "I didn't know. I thought you knew I knew." "Well, I didn't." (Silence) "You know Lilly, I remember your cock being a little smaller," Lilly felt her blood start to rise in her face. "Hey, it's no big deal. I think it's pretty cool you have one." "Really?" Lilly asked in surprise. "Yeah." That turned Lilly on a bit, which made her lower part stiffen a little. It was enough for Miley to see it. Miley went into the bathroom to shower. Lilly finally noticed her hard on, then took off the towel, took herself in her hand again, & started to jerk herself off. 'Man, her boobs were as big as mine & her nipples were at full extent,' Lilly thought, remembering seeing Miley's naked boobs & nipples. Miley was busy herself. You know what I mean. ... PEACE ... ***** Ch. 3 ***** It has been three days since the awkward bathroom moment and everything has gone normally. Miley has been doing her concerts and Lilly working at her dad's company, Truscott Corp. Which has grown a lot since Lilly started working there as co-president. This morning Miley thought that it was going to be a good idea to go and make breakfast at Lilly's house. It was 11 a.m. when Miley arrived at Lilly's, having a key, so she didn't need to call Lilly to open the door. When Miley opened the door, she was met with loud rock music and then she remembered seeing Oliver's car parked at the driveway. She made her way to the game room and was met with a so normal picture for her; two friends shooting death stares at each other playing Guitar Hero. She saw Lilly in her white boxers with a Spider-Man print on the butt with a black wife beater and her cute bed head. Miley thought Lilly looked so cute like that. And on the other side, she saw Oliver in just his Winnie the Pooh boxers and weird head that was not cute at all. "Hey, you two! Want some toast or eggs or something? I'm in the mood to cook," she said making both friends jump. "Oh! Not for me I have to go to work. My boss is about to fire me, so got to go," he left his guitar on the sofa and walked to the room that he usually uses when he stays at Lilly's. "Miley, I think I want some eggs with sausage and some toasts too. Mmm… and maybe some waffles too," Lilly started salivating. Miley just smiled and made her way to the kitchen. Miley just loves to cook in Lilly's kitchen. Lilly turned off the TV and her PS3 and made her way to the kitchen too. Lilly sat on one of the stools and stared at Miley. She really liked to look at Miley when she cooked. It made her feel like she was watching her wife cooking and that made her feel funny on the inside. She has had a crush on her friend since many moons ago and Lilly thought that maybe her crush had transformed into love. Lilly was watching Miley cook and her imagination started working. Miley's in the kitchen using just an apron, and cutting some sausage. Lilly was staring at Miley's every move until Miley looked to her with her blue-gray eyes that Lilly could swear that she saw them change to dark blue in just a second. Lilly gulped. The brunette took one of the sausages and guided it to her mouth, slowly and sensually. When the sausage touched her lips, she opened them and took the tip in her mouth, then slowly bit it, making a small moan when she tasted it. Lilly's jaws clenched in reaction to the action. Miley smiled at Lilly and repeated the bit again and again, until she was finished with the sausage. Lilly could feel that, with just that simple act, she was already hard. Miley looked at the blond again and with her index finger 'told' her to come closer, Lilly just got up off the stool and, like a little puppy, made her way to her seductress. When Lilly was close enough, Miley took her by the neck and pecked her lips once, twice, at the third time Miley took Lilly's lower lip between her teeth and pull it, making Lilly moan in response. Miley tugged hard at Lilly's lip, then released it, then she started kissing and biting the long neck of the surfer. Miley found the point that made Lilly tremble in pleasure, while her hand started going to the end of the wife beater and pulled it up until it was just below the surfer's breasts and then with her long manicured nails, scratched the blonde's strong abdomen until her nails reached the start of the boxers and then moved up again. Lilly could feel herself hardening more and twitched at anything Miley did to her. Miley stopped kissing Lilly's neck and slowly knelt in front of her. Miley hooked her finger into Lilly's boxers and dragged them down, releasing Lilly's long, hard, thick member from its prison. The singer got hold of the member and started playing with it, with her middle finger feeling along the vain that was popping from the base to the tip. She wet her thumb with her tongue and slid it on the tip of Lilly's cock. Lilly's breath coughed in her throat. Lilly was completely in a trance at seeing what Miley was doing to her. She couldn't believe that Miley Stewart was on her knees in front of her giving her a hand job. Lilly hissed in pleasure when she felt the singer's lips kissing the head of her penis, while stroking it with her hand. The brunette slid her tongue out of her mouth slowly and to a little lick on Lilly's tip, making the surfer thrust and hit her mouth with her growing member. Miley opened her mouth, took in the tip and sucked. Lilly shook her head back and made a roaring noise that Miley could swear was animal-like. Miley started to push Lilly's erection all the way into her throat and gagged in reaction to having Lilly's full length in her mouth… well a little less than her full length. Lilly felt like she was coming, but at that moment, Miley stopped everything and got on her feet. "No please Miley, don't leave me like this, please!" "Who told you I was going to?" The blond got a little confused at this, while Miley start walking to the kitchen counter. "Come here and fuck me, tiger," Lilly's mouth dropped but she still went over to Miley. She took off her clothes, Lilly did the same, then she bent backwards on the counter. "Ready love?" Miley nodded and Lilly took Miley's left leg and put it on her shoulder. Lilly loved flexible girls and she has seen Miley do yoga. Just thinking of it, made Lilly more horny. Miley waited in her position on the counter and waited for Lilly to thrust. Lilly situated her head parallel to Miley's entrance and start sliding in, slowly. Feeling Miley's heat surrounding her was something else. Lilly growled and pushed all of herself into Miley. Miley moaned and started moving her hips. "God! Please Lilly, move! Ah! Do something!" At this, Lilly start trusting, a little faster. "Faster, Harder! Lilly please!" Lilly smirked at this, but continued at the same rhythm. In out, in out, a soft mantra of skin hitting skin was heard. Miley started feeling her leg getting weaker, but she didn't care all she wanted is for Lilly to fuck her senseless. "God Lilly please go faster… make me sore I don't care just… ah!" Miley moaned when she felt Lilly hit a spot within her. Lilly too started to feel a little desperate and took Miley's leg from her shoulder and put it on the floor again. Lilly took hold of Miley's butt and put her more on the counter, making Miley's wrap her legs around Lilly's waist and she started thrusting faster and harder, totally desperate for the release. "Ah! Lilly I'm… Aah!" Miley came, riding out her orgasm, but after, she still felt Lilly thrusting into her still, hard. Miley moaned, still turned on by Lilly and still really sensitive. Lilly trusted harder and faster into Miley's core and started feeling like she was going to come. "LILLY!" "Lilly!" "Lilly!" "Ah! What!?" she got out of her trance by an annoying voice… Oliver. He was already changed and ready to leave, but he notice his friend, with her dreamy expression, starring at Miley. "I think you got hard. Hurry I'll distract Miley," Lilly nodded, then got off her stool and hurried to the restroom to take care of this problem…. She had to do something with this thing she had for Miley. This was the third time this week she found herself hard just by imagining fucking Miley. ... PEACE ... ***** Ch. 4 ***** A day later... 'Man, I can't keep this thing down!" Lilly thought, stroking herself. She was in her room. It was late at night & she was in her room, trying to relieve her self, so to speak. 'It's been going up every few minutes, for the last day & I can't catch a break,' she says, still stroking herself. She had been struggling to keep her extra part down, around her friend, Miley, who she's been having sex dreams about lately. The second Miley entered the room, she thought back to her dreams & then immediately got hard, so she's had to go into other rooms to relieve herself. Lilly kept thinking of that hot dream she had had a day ago. Miley sucking on her, let her fuck her, blew her, & then a new thought came to her mind. She pictured Miley coming in the room, catching her jerking off, batting her hand out of the way, then jerked her off, sucked her, & played with her balls. She then got up on Lilly, took her into her pussy, then started bouncing up & down on Lilly, fast. They both moaned loudly, as Lilly put her hands on Miley's ass & Miley leaned down to kiss Lilly, as they moaned into & had their tongues invade each other's mouths. In reality, Lilly started jerking faster. When she got close, she backed her back up against the wall, then bended forward, upside down, to take herself into her mouth. She did that by putting her legs behind her head, then bobbing her head, fast. She deep throated herself, then came in her mouth. She came so much, that she spit herself out & swallowed what she could. She then uncurled herself & layed spread out on her bed, as her part softened. She didn't mind the taste of herself, since she's gotten used to it. She's blown herself a number of times over the years, since she figured out how to do it. She's perfected the art of it, seeing what felt good and what didn't. She even tasted her cum & thought it was good. She was laying down on her bed, spread out all over it. She sighed in contentment. There was a knock on the door. "Lilly. It's Miley. Can I come in?" "Just a second," Lilly said, getting under her blanket. "All right," she covered everything up to her breasts. Miley came in. She walked over to Lilly & then sat on the bed. She was wearing just her bath robe. "You naked?" "I've decided to sleep naked from now on." "Lilly. I wanna tell you that I want you to be comfortable around me now that I know your secret." "What?" "You heard me. I want you to be more comfortable, so all day tomorrow, since we've got nothing going on, I'm gonna be naked all day & I want you to be too." "You want me to be naked with you at the same time?" "Yeah." "I've noticed that you bolt right out of the room. I thought it was because you didn't want to make things more awkward by us possibly discussing what happened a few days ago." "Oh yeah. That's why I've been running out of the room when you came in," Lilly said, with a slight chuckle. "Anyways, I wanted us to be naked, so there's no longer a lot of tension between us," she said getting up, then started to untie her robe's belt. "You can wear some clothes, if you want," she takes the robe off, then held it in her hand, as she put her hands on her hands, completely stark naked. That got Lily's attention. "But I won't be wearing anything," she said, dropping her robe, then walking towards the doorway. When she was in the doorway, Lilly got up, then started running, but Miley got to the doorway, she closed the door. Lilly was still running, dick & balls flapping between her legs, hard. When Miley closed the door, Lilly stopped at the door & then lightly hit her fist on the wall. She turned around, then said, "Her boobs get bigger?" she wondered, then walked back toward her bed, remembering what she saw. She then picked up Miley's robe off the floor & smelled it. It smelled good, which turned her on more. She then got back on her bed & started jerking off to the mental image Miley just gave her. Miley, however, was in her room, using a big dildo to fuck herself. "Lilly!" Miley yelled, cumming. "Miley!" Lilly yelled, cumming. ... PEACE ... ***** Ch. 5 ***** Lilly woke up that morning. It was about 8:00 & she immediately smelled bacon. She was hungry, from burning off all that energy she did last night. She got up, then went to here bathroom, which was connected to her room. She lifted the toilet seat & let it rip, peeing into the toilet. Once she was done, she flushed, then got into the shower, turned it on, then started washing herself. She thought back to the night before & Miley's offer. She wasn't sure if that really happened, or not. After she was done showering, she put on her long bath robe & went to the kitchen for some cereal. When she got downstairs, she got a bowl, some cereal, milk, & a spoon. She poured the cereal & just as she was just about to pour the milk... "Hey, Lilly," Miley says, entering the kitchen, in a yawning voice. Lilly turned around & saw Miley...naked. She gasped, almost spilling the milk when jerking the container upward. "What? I told you I was going to be naked & I'd want you to be too." "I am." "A towel around your waste isn't naked. Just topless. Come on, take the towel off." Lilly didn't know what to say. Miley already was causing her to battle the urge to bend her over & take her there, as rough & fast as possible. "Lilly," Miley said, as Lilly was brought out of her day dream. "Lilly," Miley said, jerking her back. Lilly inhaled sharply, shaking her head. "I'm sorry, what?" she said, finally getting some words out . "You know what I said. Drop the towel." Lilly was fighting a lot of naughty thoughts. Pretty much, the towel was the only thing, barely, keeping her little friend at bay, to a degree. "Umm... I'm not sure I should." "Why?" "I don't mean to be inappropriate, but the towel's the only thing from making this moment awkward." "How would that...Oh. It's ok. It's perfectly normal for someone in your condition." "Really? You're not as embarrassed as I am?" "If anything, I consider it a compliment. Besides, we've been best friends for several years now. It shouldn't be too bad." "Oh, you have no idea how wrong you are," Lilly said in a whispery voice. "What?" "Nothing, nothing. You sure about this?" "Yeah. Drop your towel." Lilly was still hesitant, but decided there was no fighting Miley on this, so she undid the knot & let the towel drop, her cock springing free from its prison. It pointed straight at Miley. She gasped at the surprise at how big it was. "You mean, you had a cock that big hidden away all these years?" "Yeah," Lilly said, cock-y. "How? I mean, you wear all those jeans & skirts. How could you keep that snake under wraps like you have!?" "I have a system." "I'll say," Miley said, turning around, getting a cup of coffee from the pot then taking the mug & sitting at the table. Lilly sat down at the table too, after pouring the rest of the milk. After a minute, "How big is that thing?" "8 & 1/2 inches last time I checked." "My god. So, it works like a guy's?" "Yep in just about every way." "Wow." "So, you saw me fuck Joanie years ago?" "Yeah. How'd you manage that?" "She told me she was a lesbian. She also had a crush on you, hence why she always competed with you. I told her you weren't like that & she was disappointed. Anyways, before I knew it, she kissed me & we were seriously making out. One thing led to another & we eventually found ourselves having sex in your guest room." "She wasn't freaked out when she found out your secret?" "If anything, she was turned on even more, seeing it as 'icing on the cake,' as she said." "Wow." "Yeah, we went at it for hours, only stopping when we got worn out & fell asleep in your living room." "Ugh. TMI, Lil." "Sorry. I've just never had the chance to talk about this, let alone brag before." "Yeah, well, keep it to yourself." "K." They both sat in silence, as Lilly ate her cereal & Miley drank her coffee. "You ever wanna have sex with me?" "What?" "You know, have you ever wanted to fuck me?" "Truthfully, I've had urges, but I've never acted on them," Lilly said, surprised she did. "Really?" "Well, yeah. Everyone with a dick has urges that they don't act upon because of the society we're apart of. I thought it was the same for the people with vaginas." "It is, but I just wanted to know. By the way, what do I call you? Girl? Boy? Shemale?" "The proper term, is 'futa,' a full girl born with a penis. Everywhere else, I'm female, it's just I have male reproductive organs instead of female ones." "Hmm..." "Yep, no periods for me," She laughed slightly, then stopped. Miley got up & walked to the sink, then put her mug away. Lilly was finishing her cereal, as she felt something on her little friend. She looked down, to see a female hand, then looked to her side to see Miley staring intently down at her part. Lilly moaned, as she felt herself grow steadily harder. "What are you doing?" she asked Miley. "Seeing what it was Joanie liked about you." "By jerking me off?" she asked, breathing slightly deeper. "Not just that," Miley said, kneeling down in from of Lilly. She then started licking Lilly's head. This made her moan loudly. Miley then stepped it up a notch & lowered her head onto the hard part. Lilly practically screeched at the feeling of Miley's mouth. She felt Miley try to go down further. She thought she'd help, so she forced Miley's head down with her hands, to the point that she entered the back of Miley's throat. Miley let her, holding her breath until her face met the skin of Lilly's front. She held there until she couldn't bear it any more, then got off. Her tongue rolled on the underside of Lilly's dick, causing Lilly to cum, spewing all over Miley's face, as Miley gasped for air. Lilly moaned very loudly, as she came hard. She panted, as Miley do also, but also picked up Lilly's towel beside her chair & whipped the cum off her face. "Man, that was good," Lilly said. "Maybe for you, but I haven't had my fill yet," Miley said, standing up, positioning Lilly's tip at her entrance, and forced herself down on her. ... PEACE ... 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