hannah montana cheerleading tryouts

Disclaimer: don’t own Disney or any Disney shows. As far as I know nothing similar to this has ever happened. If so then cool, send me a video or at least a detailed description. If you want to post this somewhere else then cool, please tell me and leave my name. Any created characters are up for grabs but I didn’t put a lot of effort into them so there is no real reason to take them.

Obviously I am taking some liberties. Lily’s family history and Lily’s sexual experience. Miley’s sexual experience. And of course any physical descriptions of places. I want to thank the people that reviewed and the ones that emailed me. But please give me some criticism. I love hearing that people liked it but if there is something you didn’t like please tell me. This will only be my second story. I know I have a lot of work to do. Also I have had the flu for 3 weeks so please blame any errors in the story like grammar on the flu. Tell me what I screwed up on and I will fix it as soon as possible.

Hannah Montana Cheerleading Tryouts Part 2 Miley’s Turn

By Dest

M/f, oral, first, bribery


Lily was feeling pretty good about herself about making the team. The fact that she had a few orgasms was adding to that a little bit. So after the tryout and a quick shower she went to pick up Miley before heading out to the mall. Miley did not know what Lily had done so she was pretty confident she would be given the last spot. They were best friends and Miley thought Lily could use some cheering up “Don’t feel bad Lil. You did your best. Maybe he liked your routine better anyway.” Lily decided to explain why cheerleading meant so much to her, just in case Miley found out how she “earned” the spot. “Well I guess we won’t know who did the best until Monday. I really need the spot though. My family has a history with cheerleading. Every living female relative was on the cheerleading squad and only one was not the captain. Mom has been putting a lot of pressure on me to make it.” Lily also figured this would prevent Miley from being sad when Lily won. “Wow, I didn’t know that. Now I think I would rather you got the spot then me.” Miley thought “Shit! There is no way he will choose Lily. She made so many mistakes during her routine. Unless she dazzled him in the final competition when I wasn’t there she is sunk.” After a few hours of shopping and general gossip the girls parted and went home. All Miley could think about when she was lying in bed was the look on Lily’s face when she found out Miley had won the last spot. Miley decided to go to the school tomorrow and talk to Mr. Fineberg. He had mentioned being there if she had any questions.


The Next Day…


‘Hi Mr. Fineberg.” “Miley? What are you doing here?” With one look at her face I realized I would have to take away the spot she rightfully earned and give it to her best friend because I had sex with her. I felt like shit. “I need to talk to you about that cheerleading spot” Miley said bringing me out of my own thoughts. “What about it? You know I won’t be making my final decision until Monday. And I can’t tell you in advance who will get the spot.” “I know sir. But I decided to back out. Lily wants this much more then I do. She should be on the squad instead of me.” To say I was floored would be an understatement. I could now give Lily the spot and not feel guilty at all, aside from the fact that I slept with a minor half my age. But I sensed something from Miley and decided to toy with her a little bit.


“Well I wish I could help you. But you signed a contract saying you were trying out and that you would stick with it.” “Can’t you let me slide on that?” “Well I could, but if I make an exception for you and break a contract the school would have grounds to fire me. And since this is only my first year I don’t have the clout needed to preserve my job.” Miley looked pretty dejected at that. “Well what if there was a way I could convince you to give Lily the spot?” This was sounding pretty interesting but I played dumb. “What could you do? I have already seen how talented you are and I have compared it to how talented Lily is. It seems like my choice is clear.”


Miley walked up close to me and whispered in my ear, “what if I convinced you with something other then my dancing skills?” Well by now I was very erect and pretty sure we were on the same page. “What are you going to convince me with?” “Oh you’ll see” she said with a smirk. That was when I felt her hands on my chest. She started unbuttoning my shirt and kissing my neck. I tried comparing Lily’s and Miley’s kissing and Miley was definitely more timid. Lily had admitted to having sex before and said Miley was a virgin. I was having a little trouble believing it now though. “Oh Miley, what are you doing?” “Just using what God gave me to help a friend out. With my shirt completely unbuttoned Miley tried taking it off but I had to help her a little. Now I could see how nervous she truly was. There was no way she had as much experience as Lily. “Before we do anything I need to know how many you have done this to before me.” “Well actually I am a virgin. I was going to have sex with this boy Jake. He had already stripped me naked and gotten me ready. But when I touched his dick through his pants he came. Then he moved away and I haven’t found anyone else I want to have sex with.” Then she leaned right next to my ear, “Until now.” I swear I was way too close to cumming in my pants after that. I knew I needed to stall her a bit so I could regain some control. “Are you sure you want me to be your first then? I don’t want to make you do something you will regret later.” “Oh don’t worry. Me and Lily both have the hots for you. We were checking you out the entire time we were trying out yesterday. And I know we affected you. We could see your erection all day long. What did you do with that hard-on? I thought I heard you jacking off during my personal dance routine. It made me so hot. Did you get off then or wait until Lily’s routine?” Damn I was not as sly as I had hoped. But on the other hand because of it I had already fucked Lily, and unless this was a dream I was about to take Miley’s virginity. “Oh I came during Lily’s routine. And with the tension I gathered up watching your two fine asses all day it was quite an ejaculation.” “Oh God you don’t know how hot that makes me. It makes me want to touch myself.” “Why do that when you have me here?”


With that I quickly stripped her shirt and skirt off of her teenage body and gave her a quick once-over. Damn was she fine! Two of the finest teenage girls I had ever seen were naked in my office in the last two days. I love this school! When I looked her over I noticed something that I couldn’t believe I had missed. She was not wearing any underwear! “Dirty girl. You knew what we were going to do all along, didn’t you?” “Well I figured either I would have to convince you to give Lily the spot, or I would reward you for giving Lily the spot. Either way I knew we would be fucking and this would make you hot.” She was definitely right about that. To think that she was walking around in a short skirt and no panties made me hornier then I had been in a very long time.


I grabbed her neck with both hands and leaned in for a kiss. While she definitely had less experience then Lily it was better in some ways. I got to be the dominant one this time. Yesterday Lily was the one really in charge. It was exciting knowing that I had lost control but at the same time I had never been the submissive one before. Kissing Miley felt a lot more normal. Leaving one hand on her neck I used the other one to explore her body. She was definitely a couple cup sizes below Lily in the breast department. But they felt so perfect for her body. Any bigger or smaller and she would have looked unnatural. After tweaking her nipples a bit and feeling her moan a bit into my mouth I let my hand continue its trek down her body. Finally I stopped kissing her lips and kissed her entire face. I kissed each individual lip and her nose. I sucked on her earlobe. Then I brought my mouth down to her neck. I moved the hand on her neck down to her ass. I learned my lesson with Lily. Grab the ass early. I did not spend as much time with Lily’s ass as I would have liked. I gave Miley’s neck short hard kisses.


Meanwhile my hand finally reached its destination between Miley’s legs. I really wanted to tease her, so I brought one finger to her inner folds. Damn I couldn’t believe how wet she was. She was more turned on by this then I thought. Not even Lily was this wet. “Oh God that feels so good. I can’t wait to feel your dick in me.” Well she really knows how to get a guys attention. After slipping my finger up the knuckle into her I withdrew. I could hear her whimpering. I moved my mouth down to her breasts to increase the torture. “Please keep fingering me. I need to release!” I knew that if I continued to tease her it would make her eventual climax even better so I didn’t give in. I brought my lips away from the valley in-between her breasts to say, “Remember patience is a virtue. This will just make your climax feel even better.” “You are evil! Just get me off! I am burning up!” That brought a huge smile to my lips. I couldn’t wait to sink my dick into her. But I knew it would have to wait so kept up the teasing. I put my finger back into her pussy and let another finger nuzzle her clit. “Oh God! Keep it up!” I knew I had to be careful or she would be brought to orgasm a lot sooner then I wanted but I loved hearing her moan. I finally let my mouth clasp her nipple. Miley’s moaning was really getting loud now. I took my hand away from her ass and squeezed her other tit. I knew that with how tight Miley was I would have a hard time squeezing my dick into her. I couldn’t even fit my other finger in. I was pumping it slowly in and out of her pussy but I couldn’t get much more in. “Relax Miley, I won’t be able to fuck you if you stay this tense. My dick won’t fit inside you.” “Okay I’ll try.” After a few more pumps I knew she needed some oral action. I reluctantly took my mouth away from her nipple and started kissing my way down her body again. I took my finger out of her cunt which clearly pissed Miley off. “WHAT ARE YOU FUCKING DOING! I AM SO CLOSE. DON’T STOP!”


With that I brought my tongue down and teased her clit. “OOH OOH YES! PLEASE KEEP GOING!” Then I put my tongue back into my mouth and scraped her clit with my teeth. Miley was panting now and I knew it was only a matter of seconds til she hit sweet release. I finally brought my tongue down to her pussy and entered her. “YES YES YES OH GOD YESSS!” I took that as a good sign. I used my nose to hit her clit and my mouth was flooded with her cum. With that her knees collapsed and she fell to the floor. “That was the best orgasm of my life! You are a GOD!” Well that keeps my self-esteem really high. Unfortunately my dick was burning a hole through my pants. Somehow I was still fully dressed from the waist down. I unzipped my pants and took them the rest of the way off. My dick was pointing straight out with the material of my boxers barely holding it in. “Oh wow! That is what you are packing. I was expecting something much smaller.” Well that hurt a lot. “Are you saying you don’t want to continue?” All that was running through my head was please god no, have a heart! “I didn’t say that. But I am going to have to lube you up.” Jackpot! I lowered my boxers off my painfully erect dick and sat back into my chair.


Miley got up onto her knees and looked at my dick for a while. Finally I had to ask her if there was something wrong. “Well this is the first time I have seen a real dick. I just can’t believe how big it is.” Again my ego was feeling pretty good but I needed to release quickly. Finally Miley brought her hand up and gave it a few quick pumps. I couldn’t help groaning. Miley seemed to like that and brought her head down to my dick. She opened her mouth and gave my dick a tentative lick. “Well that is better then I expected. A little salty but not at all bad.” She lowered her head and took the tip into her mouth. I sighed at the warm feeling her mouth gave off. I knew her pussy would feel even better and that thought almost made me shoot off right there. With one hand on the bottom of my shaft she brought the other hand up and started playing with my balls. She kept massaging and kneading them. I knew I would bust soon. She kept lowering her head down on my dick but she was definitely lacking in experience. She couldn’t get a good rhythm and she scraped her teeth hard on it a few times. Eventually I had to stop her.


“Was it really that bad?” “No of course not. I just want to move on so we can both be pleasured.” No reason to hurt the girl’s feelings. She was clearly doing her best. But she clearly needed practice. I would of course be willing to be her practice dummy but that would have to be another time. Her cunt was calling for me. I was ready. In case Lily wanted another go I had grabbed some condoms yesterday and put them in my wallet. I dug one out and put it on. “So Miley, how do you want to do this?” “Any way is good for me. I just want to feel your dick in my vagina.” I decided to let her dictate the pace then. I knew that with how tight she is I would have trouble holding back from hurting her. “Okay, I will stay in my chair and you will mount me. Sound good?” “Great!”


She got on her knees on top of me and let her legs go to either side of me. I positioned her right above my cock. “Now you will have to do most of the work. Okay?” She nodded and lowered herself until my dick was entering her. It had been so long since I had sex with a virgin. The only virgin I had sex with was the one I lost my virginity to. That was at least 10 years ago. I had no idea what to expect from her. Miley was biting her lip because she was so nervous. I bent her down and kissed her. “Relax. You are in control. If you stay tense then you won’t enjoy it.” That seemed to calm her down. She finally let gravity start its work. She lowered onto my dick and the first 2 inches went in. OH MY GOD! She is tight! Miley let out a pained moan. “Don’t worry. Take your time. Get used to it before you go any farther. It will feel a lot better.” “Thanks Mr. Fineberg. I am glad I am doing this with you.” With that I moved both of my hands to her sweet derrière. I gave it a big squeeze which had the unexpected effect of making her drop down onto my dick. Now four inches were in and I could feel her hymen.


“This will be the hardest part. After this the rest will be easy.” Not exactly true but I had to say something. Plus maybe it is true. It’s not like I ever had a hymen break. With tears in her eyes she dropped down hard and let my dick break on through her hymen. “Oh my god this hurts!” Don’t think about it. Think about how good it felt when I was eating you out. Once you get used to my dick in you it will feel even better then that. She trusted me and waited. After 2-3 minutes she raised her body up and slowly lowered it back down and went back up. My dick felt on fire. I knew I would cum soon and I wanted her to cum with me. I took one hand away from her ass and started playing with her clit. “Oh Wow! That feels incredible!” With my other hand I started playing around with her asshole. Not entering it but just toying with hit. Letting my nail nudge its way in a little bit. She had forgotten all about the pain of my dick in her. She dropped all the way down hard onto my dick and my entire dick sank in. I was expecting her to scream in pain but apparently the pleasure had kicked in. Miley started bouncing up and down on my dick slowly. Her mouth open in frozen screams. I bent my head down and captured a nipple in my mouth and lightly bit down on it. At the same time I finally thrust my finger into her asshole and thrusted my body upward hard. My dick entered her fast and she gave out a scream. All the added stimulus was too much for her and she had a huge orgasm which set me off as well. I didn’t even have enough time to pull her off my dick. I just shot right into the condom. With that we both fell asleep, my dick still buried in her.


About two hours later I woke up. “Figures I was dreaming. What a dream though.” My dick felt incredible but there as some kind of added weight on me. I opened my eyes and saw a girl resting on my chest. I realized it actually happened. I took the cherry of one of the finest girls at this school. I gently shook her awake. “Miley, wake up.” “Huh? What’s going on? Oh Mr. Fineberg! I hope this convinced you to give Lily the spot.” “I can tell you without a doubt that Lily will be the recipient of that spot. But this was a long way to go just to give your friend a spot. You’d think if you were going to fuck someone just for a spot that it would be for you?” “Well Lily is my best friend. And she would do the same for me.” I knew differently but didn’t feel like telling her that. “So you think Lily would be willing to sleep with someone for a spot?” “Definitely. We had a plan to lose our virginities at our prom. But she lost hers a long time ago. It kind of makes me jealous.” I saw my window. “Jealous huh? So do you have sexual feelings for Lily?” “Well I have had dreams about her before. In fact if I were to have sex with a woman it would definitely be Lily.” Interesting. I remembered Lily telling me that if I could convince Miley to have sex with her I would be able to do whatever I wanted to Lily. Now that I knew Miley was interested I knew I would find a way to make this happen.


“Mr. Fineberg? Are you okay?” “Yeah I am fine. I guess you should be heading off. You can clean up in my bathroom. And remember that I choose cheerleading captain in a few months. If you want Lily to be the captain you will probably have to help with the decision making process.” “I will definitely do that. Thanks for the best experience of my life. Bye.” Now I could focus on how to get those two together for some wild fun. Plus how I convince them both to fuck me again. A plan was forming in my mind but it was pretty risky. Oh well, there was no way I could stop now. I had already put my career on the line by fucking underage girls. Why not try for more?