My Date With Emily

by LOAnnie2

Copyright© 2013 by LOAnnie2

Erotica Sex Story: Emily Osment gives a dying boy more than he wished for.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Celebrity   First   Oral Sex   .

Let me tell you, getting diagnosed with an inoperable brain tumor three weeks before my eighteenth birthday was one of the worst things that could have ever happened to me. Tonight though would be one of the best nights, if not the last night I had a chance to go out and enjoy myself. I was given around nine months to live, and already three of those had passed. My body starting to feel the effects of the drugs they put me on just to try and keep me from suffering, doctors said I didn't have long until I'd be confined to a hospital bed for the rest of my very short existence.

But tonight the Wishes for the Sick foundation was coming through, one last reprieve before one room became my home. I was always the shy, nerdy type. While others my age had gotten into sports, babes, and cars, I stayed true to my ways and stuck to my computer games, sci-fi books, and my one guilty pleasure, Disney.

Even though it was something reserved for pre-teen girls, I absolutely fell in love with "Hannah Montana." And surprisingly it wasn't like most people, I couldn't actually stand Miley Cyrus, I thought she was an appalling actress. No, my sights were set on her on-screen sidekick, Emily Osment. I'd watched her go from perky and cute sidekick to babe as she grew up on the show, and now Wishes for the Sick was going to give me the chance to meet her.

As you can probably imagine, I've never had a girlfriend and only made it on a few dates in my life, so the chance to meet and hang out with a celebrity, especially my celeb crush was a rather fitting end to things. Due to some of my limitations the plan was rather simple. I'd get picked up in a limo and taken to a hotel suite where I'd finally get to meet Emily and we'd be served dinner. We'd then just sit back on the couch for a few hours and watch a few movies or TV (I actually picked out a bunch of things she was in so we could at least talk about it), then she'd get picked up and taken home by the Limo and I'd get to spend the rest of the night in the suite.

I became more anxious as the limo took me through the city. I wasn't quite sure what to wear so I wore my best dress clothes. Even though it wasn't a real date I brought a flower with me (though perhaps bringing a lily was a little too cheesy, but I didn't have time to turn back now). I just sat back and waited to arrive at the hotel. I must have fallen asleep for a moment as I awoke with a little startle when I heard the door being open. "We've arrived sir," the limo driver said. I climbed out of the limo, grabbed my flower and was mobbed by several camera flashes.

A few cameramen and some people also in fancy suits came up to me. "You must be Daniel," the guy said. He went on to say how he was from Wishes for the Sick, and something about being glad to be able to provide this for me, blah, blah, blah. I have to admit, I wasn't really paying attention, I was a really just nervous at this point. Some smiling and nodding though, a little posing for the camera seemed to placate them though. Pretty soon I was being ushered to an elevator and upstairs. I was about to see if they were able to pull off the last little part of my request. If they couldn't, I wouldn't be worried but it'd be sweet if it happened.

We got out at one of the higher floors and started to proceed down the hall. She wasn't in sight yet, was she in the room already? My question was soon answered as the hotel room door was opened by one of the suits and there stood Emily, and they got the last part of my request. I always thought Emily looked the hottest when she was dressed up as Lola, an alter-ego on the show best described as an anime character come to life.

Emily couldn't be dressed hotter, especially since she was in one of my favorite Lola outfits: little purple heels, tight bright indigo pants that showed off her great legs, a white blouse with purple accents, red plaid jacket, green scarf and of course topped off by a shoulder length light shiny purple wig. Of course to top this off she wore a bright smile on her face as she came and gave me a hug.

"It's so nice to meet you Daniel."

She was hugging me, I was in heaven–Emily Osment was hugging me, and dressed as Lola. Already from her voice I could tell she was just as sweet in person as she seemed on TV. Pictures were also being taken while she was hugging me in greeting. She finally pulled back and we were asked to turn and face the camera, several more pictures being taken. I guess this is the price for something like this, publicity after all.

I'll have to admit, dinner was rather awkward. It wasn't like going out to a restaurant to grab a bite to eat, we were surrounded by camera people and the suits the entire time–it didn't really allow us a chance to talk at all. As dinner wore on I was starting to get a little disappointed, this was nothing like what I imagined it would be like. Only a few words were spoken by either of us, most of the talking being between the suits and the photographers.

After dinner started out the same way, we moved to the couch and they took staged pictures of us "talking." This lasted for about 20 minutes, more tuning out on my part, smiling, posing, looking like I was enjoying myself but I was getting bored out of my mind at this point. Finally after probably the three hundredth picture was taken Emily turned to them and said, "I thought this was supposed to be about me spending time with a sick kid, not all these pictures. Now shoo, and pick me up at 10:30."

Three hours, I was actually going to get three hours just to lazily hang out with Emily. Season 1 of Hannah Montana had been playing in the background for a bit now, it was apparently turned on when they started shooting pictures of us hanging out but in my boredom I hadn't noticed it. I just kinda concentrated on the screen while the suits and the photographers left. Once the hotel room door finally shut she got up and latched the door to prevent them from coming back.

"Finally," she said as she came back over and plopped onto the couch again, just sprawling out. Man, even as she just lays where she falls she's hot. "I'm sorry about that," she said while rolling her eyes. "I've never worked with them before, they're trying a little too hard to catch up with Make-A-Wish."

I laughed a little, it was nice to see her a lot more relaxed now. "Yeah," was all I could say in response, still just amazed that I was alone in a room with Lola–er Emily.

"So Daniel, may I ask what's wrong? They didn't really say, just that you were sick and your wish was to go on a date with me," she asked, starting to sit up.

I smiled a little–couldn't help it, she was showing interest. "Well," I started, "About three months ago, right before I turned eighteen I was diagnosed with an inoperable brain tumor. Doctors gave me nine months or so. Based on their projections I only have a few more weeks at best before it will reach a point that I'll be hospitalized permanently."

Emily opened her mouth in shock, and quickly slapped a hand up to cover it. I had to admit, this amused me greatly since I'd seen her do it so many times on TV, now here she was doing it in person. "Don't worry about it," I added hastily, "I've actually come to terms with it already."

It was another long moment before her hand came off her mouth. "I'm so sorry Daniel," she said. Now she started to look nervous and said, "Do you mind if I ask another question."

Another smile from me, "Of course Emily, ask anything."

"Well," she said, looking up and away for a moment in another adorable way, "I was wondering why when you could have asked to do anything you asked to hang out with me? I'm not that famous, I'm actually pretty normal. And won't your girlfriend get jealous?"

A laughed much more loudly this time and looked over to the TV, another one of the scenes she stole in Hannah Montana was on. I looked back to her and said, "Because I fell in love with you watching the show. I think you're a terrific actress and you just looked like someone who would be fun to be around." I'm sure I blushed as I also quickly said, "Plus I think you're totally hot." I reached up to scratch the back of my neck and said, "I also don't have a girlfriend, I've never had one."

"You've never had one? You seem nice though."

"Well," it was my turn to look away from her, "I've always been kind of a nerdy guy, so girls were never interested."

"Ah, high school," she said, "say no more." She smiled very genuinely at me. She went back to watching herself on TV for a moment before she finally turned back and looked at me more earnestly. "Wait, so you've never had a girlfriend?"

"No," I said to her. This was a lot more awkward for me to talk about then my own impending death was.

She now sat up a bit more, edging a little closer. "Is this your first date?"

"Yeah," I responded to her, feeling my cheeks burn a little bit in embarrassment.

"That is SO sweet," she said to me. "You could have done almost anything for your wish and you chose to go on a date, and chose me. That's adorable." She blushed a little and bit her lower lip, looking up at the ceiling as if she was thinking.

This was a bit weird, I didn't really know what to say, but even as she sat there it was still so hot to me, I couldn't have wished for anything more.

"Close your eyes," she barked at me. I don't think I followed through fast enough due to utter shock and she said, "Close your eyes," a little more kindly.

I closed my eyes wondering what she had in mind. I heard shuffling on the couch and waited, the actress was up to something but–"OH MY GAWD" I thought suddenly, I felt something soft touch my lips and I realized that Emily was giving me a kiss. I didn't move, completely frozen from shock. After what felt like a very good eternity she withdrew and I opened my eyes. As I pressed my lips together and looked at her as she stood over me, I noticed that she was wearing strawberry lip gloss. I also noticed that she had taken off the plaid jacket and green scarf, only in the white blouse now, I'm sure it was more comfortable for her. She had also taken off the purple wig, her long blonde hair looking absolutely luxurious without the wig covering it.

"There, now you can't say that you haven't had something special happen to you," she said as she sat down next to me. "I also hope you don't mind I lost the jacket, it's rather warm in here."

There was no complaint here, it just made it easier to look at Emily's body. Instead of sitting on the opposite side of the couch she was next to me now. We didn't talk for the next little while, instead watching two more episodes of Hannah Montana.

It was about 9 o'clock when she grabbed the remote and hit pause on the DVD. "I can't believe I'm doing this," she said. I was rather confused by her behavior–what was she going for now? "Alright Daniel, I know all the guys see me and like my body, I'm not an idiot."

I just stared at her, I didn't really know what to respond, especially since it was more of a statement then a question. She finally got to the question and said, "Which would you rather see, my tits or my ass?"

I was speechless, feeling my jaw fall open and she laughed. When I finally regained my composure I shook my head at her. "Emily, I didn't ask for this wish cause I hoped to see you naked, I just thought it would be nice to spend a few hours hanging out with you." I got up off the couch and she watched me, I went to where I left the flower I hadn't had the chance to give her and grabbed it. I brought it back and said, "I don't want you to think that's all I'm hoping for, I just think you're a really cool chick." I handed her the lily.

She smiled with what looked like genuine affection toward me. I just said, "I hope you don't think it's silly that I got you a lily, it just seemed kind of fitting Emily."

I sat back down and grabbed the remote, hitting play. What can I say, I was being genuine, just being here with Emily was great, even if all we were doing was watching TV. I glanced over at her occasionally and she still looked as though she were trying to think. She had her arms and legs crossed very tightly, I worried that it would take her a while to untangle.

The current episode ended and she again grabbed the remote and stopped the show. "You know, I know you respect me way too much to take advantage of my trying to do something nice for you, but I wonder..."

"Wonder what," I asked, an eyebrow raised at her.

She came closer and whispered in my ear, "What about Lola?"

"What do you mean?"

"Well," she said, and out of the corner of my eye I could see the starlet was smiling. "Since you're a fan, you know that Lola can be very forceful in her personality right?"

"Um, yeah," was all I could muster, trying to figure out if she was going where I thought she was.

She got up off the couch for a moment and grabbed her wig, moving to a mirror to put it back on and straighten it out properly. "Well, Lola here has decided that since you don't have too many good nights left anyway, she wants to make sure this date is amazing. Now I'm not promising anything here, but just let Lola take charge, okay?"

At the okay she turned her head a little bit and smiled widely, doing a Cheshire Cat impression. I gulped and could not believe it. "Okay," was my response–what else do you say to Lola Luftnagle anyway?

"Okay then," she replied, her voice rather chipper. "First things first, can you help me move the couch?"

I was confused again but got up and joined her on the side of the couch and she counted to three and we pushed. Being that she was still in heels she slipped, but I managed to reach out to keep her from falling too hard onto the floor.

"Okay, so I didn't stick that landing," she said with a laugh that was joined in by me–it was a modified Lilly quote. She slipped off her heels and once again we pushed the couch, moving it out of the way this time. We took the oversized fluffy recliner that was sitting in one corner of the suite and moved it in front of the TV. She threw me the remote and told me to sit down in the chair–who was I to refuse at this point?

I reached down to my arm to check my pulse, for this surely had to be a dream. Emily stood between the TV and me and reached down to the bottom of the white blouse. I couldn't believe it when she actually started to pull it up, revealing her stomach. Being such a big fan I'd be lying if I said I hadn't seen some of the bikini pictures of her that had been posted, but they were nothing compared to this. Her stomach wasn't perfectly flat and sculpted, just that nice little layer of babyfat that you'd expect on a nineteen-year-old girl. I just stared at her as more of her midriff was exposed, and higher and higher the shirt went until a different color, blue came into view. I was seeing Emily Osment's bra and it was blue, and a bit bigger than I thought getting the chance to see this in person. Soon the blouse was up and over her head–I missed that part. I also missed that she stopped for a moment and was just smiling.

"Kid in a candy shop," she said with a little bit of a laugh, drawing my attention. She reached down to her pants and turned around–I was going to get to see her best feature in the flesh. I heard the zipper go down and Emily moved her hands around to the sides of her pants to start pulling them down. I could tell they were tight as she really had to wiggle to get it started. More blue, matching panties, thong panties even as it quickly became apparent. It took her a moment–she had said some of the Lola pants were really tight in interviews but now I was seeing it in person–but finally she got the pants loose and down enough that her ass came into view, and it was glorious. Soft looking, and very, very tight, nothing being missed thanks to the thong. She continued to wiggle her ass in front of me as she slid the pants down her legs and eventually managed to step out of them.

"So everyone talks about my ass, any comments now that you have the chance?"

I was speechless, all I could say to her was, "Wow!"

"Very descriptive," she dead panned. I looked back up, afraid she was upset but she started to laugh once my eyes met hers. She turned around and said, "Well, Lola doesn't feel comfortable removing her panties, but," and she reached back behind her, unhooking the clasps to her bra. Once it came loose she brought her hands around and slid the straps down her arms and off, holding the bra in place for a moment before finally slowly lowering it, teasing me as more of her breasts came into view.

"Oh what the heck," she finally said and tossed the bra over to the couch. Her c-cup tits were great, a perfect handful topped with perfect light pink areolae and light pink nipples. Her best feature was still definitely that perfect apple-bottom ass of hers, but her breasts were simply breathtaking as well. She shook her head and laughed, "I see you like Lola."

I could only nod as she approached me, her perfect breasts jiggling a little with each step until she reached the chair and turned around, her ass only feet from my face. She reached her hands back as she crawled on top of me into the chair, sitting in my lap. As stunned as I was before, I didn't expect to have Emily sitting in my lap in only a thong and a wig.

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