Story Details

Hannah Montana

hotchick2724 on Incest Stories

Jackson laid on the couch engrossed by what was on tv. He was a huge Steven Seagal fan and this time the late morning movie on the action channel was Under Siege. "Why can't I meet a girl like that?" He asked himself out loud as the stripper jumped out of the cake. "I've got the guns to impress the ladies," Jackson said flexing his arms, "and I'm just as smooth too." As Jackson watched the female dance naked on the screen someone knocked at the door. He was anxiously waiting for the next bad ass fight scene and death scene to come and didn't seem to notice the person at the door. The knocking became much louder and the doorbell started ringing too. Coming out of his temporary trancelike state brought by the movie Jackson quickly changed the channel to Sports Center and got up to answer the door. "Yo, Fermine my man what's up?" Jackson greeted Miley's dress designer with his hand down low waiting for a low five. "I wish I had time to stay and chat with you Jackson, but my day is full. Where's Miley? I have half a dozen new outfits I need her to try on so I can see how they fit and make alterations." "She's out with our dad. They were having car problems and called to tell me to ask you if you could come back later today." "I can't my day's full. Have your dad call me later today." "But, Miley needs those outfits for her concert in three days." "I know that, but I'm on a very tight schedule and don't have a lot of room for delays. I've got really nasty impatient clients all over the city and Mandy Moore paid me a bundle to spend as much time as needed with her this afternoon to get her outfits designed and ready for her upcoming tour. Just have your father call me and we'll work something out." As Fermine started to leave Jackson stopped him with an odd question. "What if I model the clothes again? Could you get them done then?" "That's certainly a strange question. The last time you did this for me I had to pay you twenty bucks to do it." "I know that, but I'm gonna do this for Miley. She is my sister and I support her." "Personally I think you're full of baloney, but fine. Help me get my stuff out of my van." Jackson went with Fermine to his van and both took three of the outfits that were on hangers. Fermine then went back one more time to get his supplies to make minor alterations and make notes of what needed to be done. All of the outfits were dresses or two piece outfits with skirts that Jackson found himself enjoying as he tried each of them on. It took almost an hour for Fermine to make decisions about the colors and design for each piece. As Jackson took each outfit off his reluctance to do so started to increase with each piece. He was happy again when he was handed the next outfit until there were none left to try on. As he helped carry the outfits back to Fermine's van Jackson asked him another odd question. "Hey listen, I want to ask you a question, but I don't want it to get out. It could ruin my rep you know?" "What is it Jackson? I have two clients I must get to, before this afternoon. If I'm lately Mandy gets so cranky." "Do you have any of the old outfits you designed for Miley that weren't used?" "Some of them. Why?" "Well when I tried the outfits on for you they felt really comfortable and are cooler than the clothes I got. Except for the blue sequin piece. I didn't like that one." "If I did where would you wear them hmm? Your friends at school would laugh at you and Miley and your dad would think you're weird." "I know that and they already think I'm weird. I'd only wear them around the house when I'm alone. Please do this for me and you'll be my homey for life." "Please do not call me a homey. You sound ridiculous saying that, but the next time I come over I'll bring what I can find." "Aaaah yeeaaah! Gimme five!" Jackson whooped holding out his hand. "Stop that too," Fermine replied taking the last of his things to the van. * * * Just as he said he would Fermine brought over two outfits Miley never used a month after Jackson's request. One was a black dress similar to the one Jackson had modeled before except that the design on the front was different. The second outfit was a red skirt and matching halter-top. "Here you go," Fermine said handing Jackson a plastic bag with the clothes neatly folded inside. "I made some alterations to them of course so they would fit you. Don't get caught, but if you do say you stole them from me." "Trust me, I won't get caught," Jackson reassured him. "Somehow I don't believe that," Fermine replied as he got into his van. With the clothes in hand Jackson went back inside the house carefully sneaking into his room with the bag. Miley was hanging out at Lilly's house and his dad was busy laying on the couch watching tv. Upstairs in his room Jackson kept himself busy looking at his new clothes wondering what they'd look like on him. Not able to resist the urge Jackson locked his bedroom door and quickly changed clothes putting on the halter top/skirt combination. "Oh yeah! I looked good don't I?" Jackson said talking to himself in the mirror. "Steven Seagal definitely has nothing on me now." Jackson flexed for several minutes impressed with himself when he noticed something. He bent over slightly to watch the skirt ride up on him. When it did his tighty whities looked out of place. "Hmm... While these are comfortable they just don't go with this outfit, but Miley's underwear would go with this." Jackson quickly changed back into his regular clothing and stepped out of his room. Downstairs his dad was busy cleaning up the kitchen. Jackson quietly tiptoed across the hall to Miley's room and sneaked inside. Being as quiet as he could he went to his sister's dresser drawers and opened her underwear drawer. Inside Jackson found panties with all different designs and colors and rooted through them for a minute before settling on a white pair with a smiley face on the back. Jackson stuffed the panties into his pocket and carefully stepped outside. As he made his way to his room he was suddenly startled. "Hey Jackson!" His father yelled. "Wha-What?" Jackson stammered thinking he had been caught. "I've got a meeting tonight about the commercial your sister will be doing for the upcoming Hannah Montana clothing line," Robbie Stewart said from the bottom of the stairs. "It's going to be finalizing a lot of minor details and signing the paperwork so I'll be gone a few hours. Miley is spending the night at Lilly's and I left you money for dinner on the counter. Do not wreck your car." "Sure dad," Jackson stuttered. "I probably won't even leave the house. Yeah in fact just keep the money and I'll get something out of the fridge." "Are you all right son?" "Yeah, I'm fine. Why?" "It's just this is the first time you've given me money instead of taking it." "Yeah well I'm just trying to be supportive of you and Miley and everything. No problems here." "All right then I'll see you later." Jackson quickly dashed back into his room breathing a heavy sight of relief as his dad messed around the house for a few more minutes before leaving. "That was a little too close," Jackson said to himself as he took Miley's panties out of his pocket, "but were all alone now. Time to get comfortable." Once again Jackson took his own clothing off and began putting the top and skirt back on. As Jackson then began putting on the panties he began to realize that they were quite a bit too small for him. He kept pulling though, stretching and in some cases tearing the underwear, and eventually got them on. Finally hapy with his look he went downstairs to microwave some corndogs and watch some basketball. Jackson ate his dinner and as halftime of the game began he decided it was time for a bathroom break. A few minutes later after he relieved himself and washed his hands he emerged from the bathroom. Jackson walked into the kitchen to get himself something to drink and was met by two stares. "What are you doing?" Miley asked as she and Lilly gawked at him. "I'm trying some stuff on for Fermine... You know since you weren't here and all..." "Fermine's gone," Miley replied, "and you got paid for that last time." "You two aren't even supposed to be here. You're supposed to be spending the night at Lilly's." "We are," Lilly replied. "We just came by to get some movies. I would say let's get To Wong Foo, but I don't think we need to watch it ever again. This is really weird." "Yes it is," Miley replied. "A little too weird for me. I'm going back home. I'll see you in a little while." "Okay," Miley replied. "I'll be there in a bit. I need to talk to my brother for a moment." Miley waited until Lilly was gone before talking. "Aren't these Fermine's old outfits that I didn't use?" "Sort of." "Then why are you wearing them?" "Because they're comfortable and pretty and I like them." "You're not wearing my underwear too are you?" "Sort of." "I was just kidding Jackson!" Miley said lifting up Jackson's skirt. "Oh my god, you're wearing my smiley face panties! Those were my favorite!" "You're not going to tell dad are you? It's not like I'm gay or anything. It's just that I like these clothes better than mine and I'm still going to totally impress girls with my massive guns," Jackson said flexing his arms. "You've got to impress a girl, before you can impress many girls," Miley said grinning. "I'm not going to tell dad anything, because I love Fermine's clothes and I don't want him to get in trouble because he gave you girl clothes to wear. I'll make sure Lilly doesn't say anything to anyone either, though I don't think she'll take much convincing. There is one thing I want to do first," Miley smiled at Jackson as she flipped open her camera phone and took a picture of him. "What are going to do with that picture? Delete it before you get us both in trouble," Jackson said. "I will, but first you are going to owe me big time. After you've made up for this horrific incident I'll delete the photo and call it even." * * * "So what did Jackson say?" Lilly asked as she put ketchup on her hamburger in the school cafeteria. "About what?" Miley asked as she and Lilly sat down at a table not far from one occupied by Johnny Collins. "About the clothes he was wearing the other night." "He said they were comfortable and cooler than his clothes and that's about it. But don't say anything to anyone about it. If my dad finds out Jackson wears girl clothes he got from Fermine then he might fire him and I really like Fermine's designs." "But didn't your dad have Fermine pay Jackson try model your clothes?" "Yeah, but that to teach Jackson a lesson about money and responsibility. We were goofing on him because it was funny and a one time thing." "Well don't worry about a thing. I'm not going to tell anyone. In fact I kind of wish I hadn't seen it. Although it'd be weird if one of the tabloids found out that Hannah Montana's brother was a cross-dresser." "Lilly I'm serious! Don't say a word!" "I'm just messing with you. I won't tell anyone... Well, not as long as you go over there and ask out Johnny." "We've been through this before. I act like a total idiot when I'm around him." "What's the problem Miley? He said you're funny, the whole ketchup incident didn't turn him off, and he's a huge fan of Hannah Montana." "You know what Lilly you're right! I'm going to go over there and talk to him," Miley said confidentially as she stood up, but before she could move Amber sat down at the table next to Johnny. "But not today," She said defeated and sat back down. "God, Amber and Ashley sure have a way of ruining things. Where is Ashley anyway?" "I heard she had a zit on her forehead and her parents are calling her in sick until it goes away." "Oh man that's not cool," Lilly remarked as Amber and Johnny started kissing at the table. "I'm going outside," Miley mumbled getting up from the table. "What? Why?" Just then Amber and Johnny broke their kiss and Amber turned to look at the girls. She gave them a cute smile and a wave and turned her attention back to Johnny. "God, I want to strangle her so bad and if I stay I just might try and do it," Miley grumbled leaving the cafeteria. "Miley! Hey Miley wait!" Lilly shouted chasing after her into the hallway. "You've got to do something Miley. You can't just stand around let Amber and Ashley walk all over you whenever they feel like it." "What should I do? I'm not going to get into a fight over a boy." "You don't have to fight them, but do something. They've treated us both like crap since the day we first met them." "I don't know. Maybe I'll think of something." As Miley spoke those words an idea started to form in her head about how to make Johnny hers. * * * "Hey Jackson is dad home?" Miley said entering the house with a towel wrapped around her body. "Not yet," Jackson replied glued to the tv. "Do you know when he's going to be back?" Miley asked removing the towel and revealing a solid red bikini top and bottom. "Nope. He hasn't called yet." "Good we need to talk," Miley said walking across the living into the kitchen to get a bottle of water from the fridge. "You know he's gonna kill you when he finds out you have that swimsuit." "I wonder what he'll do when he finds out you like wearing girls clothes." "Hey now," Jackson started sitting up on the couch. "You get me in trouble you also get Fermine in trouble." "Nah, I'll just say you stole the clothes and a pair of my panties." "That's not cool Miley. I thought we said everything was fine." "No we said neither of us would say a thing about your dressing up to anybody." "So what are you dissin' me for? Why you playing me like this?" "Don't talk like that Jackson. You sound stupid." "What do you want?" "Amber is trying to start a relationship with a guy at school that I really like. She's already got a head start too." "So what do you want me to do about it?" "You know how dad doesn't let me go on dates unless it's in a group or it's with Oliver." "That's the one thing that makes me glad I'm not you," Jackson snickered. "Just shut up and listen. I've got an idea on how to make Johnny mine, but I need your help." "Johnny eh? He's the one with the big fuzzy hair right?" "God, you are making this so difficult." "What do you want? I'm missing Marked For Death." "Didn't dad say he didn't want you to watch those kinds of movies," Miley asked turning the tv off. "They make your mind stupid." "But I ain't his fourteen-year-old daughter flaunting her body at the beach." "Can you please shut up for five minutes and let me talk?" "Nobody's stopping you." "All right fine look. If I have sex with Johnny he'll become my boyfriend and forget all about Amber, but I need someone to practice with. Although in your case you need to practice as much as I do." "Hey, hey, hey. I impress girls all the time with my guns," Jackson retorted flexing his arms. "Are you going to help me or not?" "Um, no." "Why not?" "I have three reasons. One dad will kill you. Two dad will kill me. And three after he's done killing us he's probably going to say what a bad influence California has been and move us back to Tennessee. I know you miss home sometimes, but I can't go back. Not after seeing all the gorgeous girls out here." "Fine, we'll just have to be discreet about this then. Nobody's home so nobody can catch us. Besides, what happens if one of the so-called impressed girls really starts to like you and you end up looking like a fool in bed? You're reputation will be ruined forever." "Hmm... Well you do have a point." "I know, so can we do it?" "There were always the rumors about Cousin Sally and Cousin Bob." "Well?" "Okay I'm in, but you better delete that picture of me after we're done." "It's a deal, but we're going to do this in your room. I don't want you near my underwear anymore." "I'm not stealing your underwear. Mine didn't go with the skirt so I took one of yours," Jackson replied as he and Miley headed towards his room. When they got there Miley quickly removed her two piece suit and Jackson looked her up and down a bit. "There a problem?" She asked waiting for him to undress. "No, not at all. I've never thought about it, but you are kind of cute. Your chest is kind of small though for a girl your age," Jackson replied wiggling his shirt off before starting on his pants. "Yeah well, everyone here has fake boobs okay? And I don't think you have too much room to taaa- oh my god," Miley stuttered as Jackson's pants and underwear fell to the floor. "What?" Jackson asked seeing his sister stare at his crotch. "How big is that thing?" "How big is what?" "You're penis you idiot!" "Oh, I think it it's like seven inches. Some girl measured it last year at a party when we were playing truth or dare and I had to flash everyone." "I must say I am impressed. You're not the brightest person in the world, but you make up for it in other ways." "Why thank you. Once I impress the ladies with my big guns," Jackson said flexing his arms. "I can impress them with my big gun," He said gyrating his hips. "Okay that was really really corny," Miley said sitting down on his bed. "Now come here." "This was your idea so what do you want to do?" Jackson asked sitting down next to his sister. Without saying a word Miley leaned in and kissed him on the lips. Both had their eyes shut as their lips pressed together for at least half a minute. When the kiss broke they opened their eyes, Jackson first then Miley, and they smiled near simultaneously. "That was pretty good Jackson," Miley smiled. "You were pretty good too little sister." They kissed each other again, but this time their tongues slipped into each other's mouth. The appendages intertwined with each other swapping saliva. When Miley and Jackson broke their kiss again their smiles seemed to had gotten even bigger. "Lay back Miley," Jackson said standing to reposition himself on the bed as she did as he asked. "Now spread your legs for me." "Oooh Jackson!" Miley moaned as she felt her brother's tongue start to pressed up and down her slit. His nose was nuzzled in the small patch of hair of she had growing around her pussy and occasionally his tongue would press into her clit as he slid it up her opening. Jackson continued eating out Miley slipping his tongue into her pussy to taste her juices. Having her brother lick her cunt inside and out instead of having to use her fingers to get off was bliss for Miley. After only a few minutes her body was already burning up. Miley felt her body working itself ever closer to orgasm as Jackson kept pushing his tongue inside her to lick up her cum. Then suddenly it stopped. "Oh god!" Miley cried as her brother slipped his index finger in-between her pussy lips. "Finger me hard!" Jackson was momentarily caught off guard by Miley's forwardness, but still managed to happily oblige his sister. He slowly worked his finger in and out of Miley's cunt trying his best to work it all the way around inside her. His sister's pussy felt warm to his touch and as he kept sliding his finger in and out of her it started to moisten rather quickly. Soon Jackson's finger became a little too loose and slippery so he slipped his middle finger in as well. He began fingering Miley's cunt with a faster pace and her moans began to flow freer and louder. "Oh my god Jackson! This feels so good!" His sister moaned as he worked his fingers deep and hard into her pussy. It was only a couple of minutes after the second finger was added that Miley lost control of herself and began to come. "Fuck me Jackson! I'm coming!" Jackson was pleasantly surprised as Miley's pussy clamped down hard on his fingers. He watched as his sister's body shook with her orgasm. He felt her young teen pussy squirt her cum all over his fingers and when she finally relaxed Jackson slipped his fingers out and began licking them. A few minutes later with a huge smile on her face she sat up. "That felt great Jackson!" She grinned. "Where did you learn how to do that so good?" "Well Miley, let's just say there's more to me than my dumb redneck act. There's so much to me that you and dad don't know," Jackson smiled back at his sister. "If you didn't need the practice then why are you helping me? You didn't have to." "I don't know. Because I want to I guess, and you are kinda cute. Now get up. I do believe it's your turn now." Jackson and Miley traded places while grinning at each other and Jackson laid back on the bed with his semi-hard seven-inch cock pointing up. "In order to keep a guy interested all you need to do is know how to work his cock right with a good mix of hands on pleasure and teasing, but don't do too much of either. You'll develop a reputation as either being easy or being a complete tease and a waste of time. You're reputation will be with you until you graduate high school." "How should I do this?" "Let's see what you've got first. Then I'll tell you what to do." Miley tentatively reached out taking hold of Jackson's shaft and began sliding her hand up and down his length. "Mmm... Loosen your grip a bit, but other wise you've got a good touch," Jackson said as his cock began to harden in his sister's hand as she stroked it. Taking his advice she loosened her grip a small bit. "Perfect Miley. You have a tight enough grip to really work the blood up into my cock and get it nice and hard. You have a nice gentle stroke too," Jackson complimented his sister as her hand continued to slide up and down his shaft keeping him hard and excited. "Now if it was just a handjob you were giving you would slowly increase your pace before working your guy into a frenzy, but that's not what we're here for." Before Jackson could say another word Miley wrapped her lips around tip of his cock and slowly slid her his shaft between her lips. Jackson was impressed that his sister could take all seven inches of him into her mouth the first time without any problems. What he didn't know was she had masturbated with and practiced oral sex on various vegetables that she later washed put back into the fridge before they were eaten for dinner. "Damn Miley... You are good..." Jackson moaned as his cock continued to slide back and forth between her lips and push into her throat all the while her tongue slithered along his fleshy member wrapping itself around it at the same time. Miley continued to move her head up and down tantalizing Jackson. He didn't know how she was so good at giving blowjobs, but she was. After several minutes of the best oral sex any girl had ever given him Jackson's throbbing dick started to reach the point where he knew orgasm wasn't far off. He could feel it in the ache of his groin and his precum was already dripping onto Miley's tongue. "Hold on Miley," Jackson panted. "I'm close to busting my nut and I don't want to yet." "Me neither," Miley smiled coyly at him. She let go of his cock and climbed on top of him straddling his groin. "Oh yeah... That feels good..." She moaned as she lowered herself onto her brother's dick splitting her pussy apart as it pushed inside. Though she was able to deepthroat Jackson without a problem taking him all the way into her pussy was different. Miley was able to get about five inches of Jackson inside her before he started to fill her up. She leaned over onto his body and propped herself up with the bed. She then began to ride her hips up and down on Jackson's dick slowly lubing it up with her cum. After several minutes of working her fluids all over her brother's shaft Miley was able to take his last two inches inside her. Smiling she sat straight up with her pussy pressed against the base of his groin. "Doesn't seem like you need too much practice either," Jackson smiled placing his hands on Miley's hips. "I appreciate your help anyway. This is fun." "You treat Johnny this well and I guarantee he will be yours," Jackson grunted as Miley started to ride his cock up and down. Brother and sister smiled at each other as their pace slowly started to increase. With his hands on Miley's hips Jackson started slamming his sister down on his cock. With each thrust of his dick into her cunt Miley's moans became louder and more frequent. "Mmm... So big Jackson..." Miley groaned as she bounced up and down on her brother's cock with force. Jackson's shaft rubbed back and forth against Miley's innerwalls as he thrust himself into her while pulling her down onto him. "Oh yeah Jackson... Feels so good..." Jackson was feeling his cock starting to really hurt. His groin begged him for release as his sister's tightened pussy continued to squeeze his dick harder and harder. As her brother's cock continued to rapidly plunge into her Miley began to feel her body tingle and her pussy started burning. "Oh god! I'm fixing to come again!" Miley groaned as her body began shaking again. She collapsed forward onto her brother as she started to come a second time. Jackson tried to continue thrusting, but the rush of Miley's cum onto his dick and her quivering tight pussy became to much for him. "I'm coming too!" He moaned as his cock exploded. Shot after shot of Jackson's semen emptied into Miley's womb. When brother and sister both calmed down Miley laid on top of Jackson and they both panted heavily. "That was great," Miley said almost giggling. "Yeah, you were pretty okay," Jackson teased. "Gee thanks." "Not a problem." "I don't mean to ruin the fun here, but what are we going to do if I become pregnant?" "Don't worry about it Miley. I know someone I can get morning after pills from when I get off work tomorrow." "So do you think I'm ready?" "You're more than ready. When and if you do have sex with Johnny don't be too good too often or you could make him feel inadequate." "Who knows about this side of you Jackson?" "About the same number of people who know you're Hannah Montana. You have your other side I have mine. We better get cleaned up and dressed though just in case this is one of those times dad just shows up late without calling." "Miley! Jackson! Are either of you here?" Someone shouted from downstairs. "Uh oh! We've got problems other than dad!" Miley exclaimed as she and Jackson quickly got out of bed and started dressing "Is anyone home?" Lilly shouted.

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