5 comments/ 73282 views/ 23 favorites Britney Story By: britneyfan Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in this section appear to get a lot more readers and a lot more feedback than in the celebs bit, for another it gives me a chance to put the stories together as one whole story as I had first thought of it. Most importantly, the feedback that I did get for the story when it was first posted was decidedly mixed, mostly based around the first part's twist (which won't come as much of a shock any more given the section I've put it into now) of a shemale Britney. The readers of this section appear to be much more open minded and so you may be better equipped to view this story in that light. In my defence, I would say that before writing this story I read the plenty of excellent Britney stories that already appear on literotica (some of the best are listed under my favourites) and knew that I couldn't hope to compete with them. However, I did notice that many of the stories combined Britney fantasies with the author's other fantasies, giving us the likes of lesbian Britney or bondage Britney, so why not transsexual Britney I thought? Hopefully you new readers may be more forgiving of the idea. One final reason for this reappearance of the story is that a sequel is in the works, time permitting, and I wanted to see if it was worth doing, if there were people out there who would want to know what happened next. So there we are, that's all I've got to say to you except that I hope you enjoy the story and all feedback is appreciated (sometimes even the bad stuff). Britneyfan ;) * 1. You Drive Me Crazy Any man who tells you that he hasn't ever fantasised about sex with the world's greatest and sexiest pop star Britney Spears is probably lying. After all, who wouldn't give anything they could just for one night with the lithe, hot All-American goddess? Frankly, when it came to Britney, I was no different from any other man, when one of her videos came on MTV I have to confess I felt a little stir of arousal and excitement, and when I closed my eyes and jerked off my cock in my lonely bedroom it was her beautiful, perfect celebrity body that I saw, writhing naked before me. Britney knew exactly what a man looked for to utterly turn him on and used this knowledge to great advantage in her skimpy, sexy costumes and suggestive dance moves that had me drooling at my TV set. Sure, there are a lot of other sexy pop stars out there, no doubt about that, but Britney has that little extra something that makes her especially appealing. Some people claim Christina Aguilera is sexier, she certainly wears more revealing clothing but she doesn't quite have the same understanding as Britney as to what men want to see. You see Britney does wear sexy revealing clothes but she mixes he in your face sexuality with a certain girl next door homely innocence that is the perfect mix to snare any guy's attention. I'd been a fan of Britney's beautiful body ever since she burst on to the scene dancing down her school hallway dressed in a midriff bearing schoolgirl's outfit, however I had later become a fan of her music as well. I was still at school when Baby One More Time came out. At the time I liked, or at least claimed to like, all the kinds of serious guitar bands that all my friends were in to, that was the kind of music we listened to together, Radiohead, Oasis, Nirvana, that kind of thing. However, as teenage boys tend to do, we also watched pop videos on MTV hoping to get the chance to ogle the beautiful pop babes. It was in this situation that I first encountered the teenage Britney, already masterful at the sexiness-innocence combination, in her Baby One More Time video. Of course this sent all us guys into a wave of excitement to discover a hot new star to drool over. While the other guys only saw this as the same as any of the Spice Girls type videos we'd already seen, there was something about the video beyond Britney's sexy body that made me want to go back and watch it again and again. Of course, I couldn't actually enjoy this cheesy pop music song, I assured myself, I was a serious guitar music lover. It wasn't until a couple of years later, by that time I was quite obsessed with Britney's gorgeous look realised I was almost as keen on her music and that Baby One More Time was much more my kind of thing than what I'd been listening to before. For once, my thirteen year-old sister Becky had been smarter than I was. She'd been into Britney's music from day one and had bought most of her singles and albums. One day, not long after I had graduated from High School and was taking some time off between school and college, Becky came home with a copy of Britney's new album, Oops, I Did It Again. As I created reasons to hang around in the living room where Becky was playing the album, I realised how much I was enjoying it without even having Britney herself to look at. The album was great fun catchy pop and I realised what I'd been missing all this time of not getting into the music that really appealed to me and instead liking what I was supposed to. In college, the fact that I owned and regularly listened to all of Britney's albums excited some comment, a lot more than the huge Britney poster I had on my wall, and people liked to mock me for it but I was more comfortable in my taste now. Each evening, I would look up at the life size poster on the wall to see Britney looking down on me, dressed in just a black halter-top and tiny shining gold hot-pants. As I became aroused even looking at the poster, I began to wonder what it would be like to be with the real Britney, to feel my body pressed against her perfect one, to feel her soft lips against mine or feel her running her hands through my hair or down my body. I imagined what it would be like to feel the real Britney, the world's most beautiful superstar, unzipping my jeans and taking out my hard cock. I imagined her slipping out of those tiny, tight gold hot-pants to reveal her pussy beneath, I imagined it totally hairless. I imagined the real Britney sitting astride me with her thighs about my waist, slowly sliding my member deeper inside her. I imagined reaching up to touch her perfect round breasts, to caress them. Then, I came, I blew my load all across my hands and my chest and I came back to realising I was just a college student, lying in bed masturbating over a poster of Britney while the real life Britney, the sexy yet virginal idol I lusted over was far away probably doing nothing like this. Probably she never had. After I graduated from University in England a couple of years ago, I decided to travel, eventually ending up in America. I took a dull, menial job in a luxury hotel in San Diego and settled down to work there for the year. I liked America and, in general, I liked Americans, it made a refreshing change from England. Maybe it was the way the beautiful California blondes reminded me of Britney or maybe the reason I was so into Britney was that the blonde all-American babe had always been my type. Whatever the reason, life in America was good to me and the hot blonde Americans were won over by my English accent far more easily then I'd ever managed to charm any much less attractive girls back home. Anyway, it was while I was working in that hotel in San Diego that I finally got to learn the answers to all my fantasies of the past five years and discovered truly what it's like to be with the world's most desired woman. Much as I had always wanted to, I'd never been to an actual Britney Spears concert, I could never really afford the prices and anyway, on the rare occasions Britney played in England tickets sold out in hours. However, in March of 2004 I discovered Britney would be coming to San Diego. I quickly decided this was my chance to see a Britney show and enthusiastically bought myself a ticked. I knew that much of the rest of the audience would probably be up to as little as half my age and certainly closer to my sister's age than mine. Still, I couldn't exactly turn down the opportunity to actually see my goddess in the flesh when she was so close to where I lived. I'd recently bought Britney's latest album, In The Zone, and I loved it, the single Toxic was her catchiest, sexiest yet and I couldn't wait to see her perform it in person. Well, I was feeling rather smug about getting the ticket and looking forward with eager anticipation to seeing Britney performing live, when I heard another piece of news, even more exciting. Britney Spears would be staying in the very hotel where I worked the night after the concert. The hotel was a very expensive luxury one and its clientele was mostly made up of the very wealthy, however this usually meant rather staid, dull business people. The occasional B-list celebrity would stay there, but the arrival of Britney was a major event that had all the hotel staff talking, even those who'd seemed never to care about the beautiful star before now. Of course, my colleagues all knew of my love of Britney, I'd only spent the past few weeks going on about seeing her in concert almost all the time, so their enthusiasm for her upcoming arrival was often directed to me. What if I ran into her coming down the corridor? Just a few days earlier, I was thrilled and excited by the possibility of simply seeing her from a distant at her concert and now there was the possibility, however slim, of actually meeting her. Well, I don't need to tell you that I practically creamed my pants (as I had done many times before in Britney's honour) at the thought of this. And as I thought about the possibility of seeing Britney so close up another idea began to form in my mind. If I could find some way of sneaking myself into her hotel room, which after all I could probably manage, I did work at the hotel, then I would have the opportunity of seeing Britney really close up and intimately. Like all the millions of other men who fantasised about Britney, I'd spent many hours trawling the internet for good quality Britney nude pictures to put a real life image to all the fantasies that had enlivened my nights. However, I had always discovered, as I'm sure is the case for many other people, that these promised Britney nude shots were always either unconvincing fakes with Britney's smiling face stuck on someone else's body, or shots of the real Britney sunbathing topless taken with a blurry telephoto lens. Wouldn't it be wonderful to have a chance to see the real thing, to see the real Britney's beautiful breasts totally exposed, to see whether her cunt really was the perfectly smooth, shaved thing I had always dreamed of? And if I could smuggle a camera in as well, just think what I could get for real pictures of the real Britney nude, it would be an internet porn story to match the Paris Hilton sex video. After all, Paris Hilton was just some heiress, but with Britney you had the most searched for woman on the whole internet. Needless to say, I was coming up with a plan to conceal myself in Britney's suite, I knew the one that she would have, the luxuriously huge top floor penthouse suite, and watch her as she undressed. To do this I would have to leave the concert early in order to get back to the hotel to sneak into her room while all her security people were still guarding her at her concert. However, missing a half hour or so of Britney performing would be a small price to pay for the full on experience of seeing her totally naked. Even in anticipation of the event my cock was rock hard. 2. Lucky All the rooms in the hotel had keys that the service people would use to go clean the rooms and stuff and I knew exactly where the relevant key was to the penthouse suite. On the afternoon of the concert, Britney checked in to the hotel and all the staff that were then on duty rushed off in a slightly unprofessional manner to see her arrive. I was with Lydia, the chambermaid who I knew had the keys that would open Britney's suite. Lydia had never shown any particular interest in pop music or Britney Spears before but now seemed eager to go with the others and see this superstar arrive. I can't say I blamed her, nothing would have pleased me more than to get that close to seeing a sexy celebrity, especially so if it was Britney, however I had bigger things in my sights. "Go and see Britney arrive," I said Lydia, "I'm happy to stay here with your stuff." "But you're her biggest fan here," said Lydia, confused and possibly a little suspicious, "Don't you want to see your idol in the flesh?" "I'm going to the concert tonight, don't you think that might be enough Britney for one day, even for me?" Fortunately, she seemed to accept this as an answer and, without any further suspicion, hurried off herself to see the arrival of Britney. As I had hoped, Lydia had left all of her things behind and that included her room keys. Quickly, I searched through them until I found the one to Britney's suite which I pocketed. They'd have already cleaned Britney's room and prepared it to all her demands before she checked in so I knew that they would probably not be needing this key again until the following day at least. That gave me a chance to carry out my plan and get the key back without anybody noticing, hopefully at least. I knew full well that an action like this could well cost me my job but that was something that I was willing to face if I head any chance of seeing this plan through and getting a glimpse of Britney's naked breasts. The Britney concert that evening was everything that I had hoped it would be. Britney appeared, dressed from the neck down in shiny vinyl and from then on I found myself slightly embarrasedly trying to prevent myself from getting an obvious erection at a public event with so many families. She wore a sexy figure hugging catsuit that clung to every curve of her body and covered everything except for a neckline that plunged to her ample cleavage. The performances were all stunning as Britney worked through a repertoire of classic hits from her early albums along with lots of the exciting, sexy new material. Now, I'm know she was lipsynching the songs, I might be a huge fan but I'm not naïve enough to not think that, but that didn't detract at all from the enjoyment of Britney's grand full on stage show which featured dazzling light shows and many more dancers, also dressed in vinyl. I have to say that it was one of the most thrilling events of my life, but hopefully better was yet to come. I took a costume change as my cue to get going and head back to the hotel, although when I saw what Britney was wearing I regretted this decision and almost changed my mind to stay and give up the rest of my plan. Where before, her black vinyl catsuit had covered almost every inch of Britney's body, now plenty of flesh was on display with what she was wearing being no more than what anyone else would consider underwear. Britney was dressed in a bright pink bra that was trimmed with a little black lace and a matching pair of bright pink hot-pants. Aside from that it was just a pair of black fishnet stockings held up by a black lace suspender belt. A few years ago people would have been shocked by this kind of stage costume from Britney but now it was just viewed as a part of her sexy image. As I left the concert venue, I was practically walking backwards trying to keep my eyes on the stage and not miss a second more of the sensual performance than I had to. Hopefully it would be worth it for the hope of an even more sensual performance back at the hotel. I sneaked in the back entrance at the hotel. I'd taken the evening off to go to the Britney concert so nobody expected to see me here. Hoping not to run into anyone, I took the lift up to the penthouse suite, so far so good. I was carrying my camera that I had already snapped some pictures of Britney in concert with, I now hoped to use it for some even more candid shots. The top floor corridor was completely deserted, to be honest I was a little surprised how easily I could pull this off, I'd have thought that the world's biggest star would have had a little more security at her hotel room even when she wasn't there. Oh well, I didn't have time to ponder over the ease of it, in case I got caught just standing out there in the corridor, I wouldn't have had much of an explanation as to what I was doing on my evening off outside Britney Spears' room with her stolen door key. I put the key in the lock and tried to open the door, my hands were sweaty and shaking with excitement so it took a couple of attempts. Finally, here I was inside Britney Spears' luxury penthouse suite, I couldn't believe my luck. The room was huge with a massive double bedroom, en suite bathroom and a large living area. I didn't have time to admire the life of celebrity luxury, however, as I had to be sure that I was comfortably in my hiding place. I walked into the bedroom leading off from the living area where I was now standing. There was a huge wardrobe in the bedroom which was where I hoped to conceal myself, provided Britney didn't look directly at me then I should be able to get a good look at her. There was a bag of Britney's in the wardrobe but most of her things were in a suitcase on the bed. Looking around anxiously although I knew that there was nobody here, I unzipped Britney's suitcase. She was kind of a slob, I could tell that instantly, none of her clothes were at all neatly folded rather just stuffed into the bag. Despite her sexy image most of the clothes were casual stuff like t-shirts and sweatpants but it didn't take me a great deal of rummaging to find what I was really looking for, some Britney underwear. What I now had in my hand were a pair of red lace panties that belonged to the gorgeous star herself. I was thrilled, even if I never got to see her naked, I had held her panties in my hand. I lifted them up to my nose, hoping to get a chance to catch a little of her scent. At that exact moment, I heard the sound that I had been dreading, the sound of another key turning in the lock of the door to the suite. Grabbing my camera that I had left lying on Britney's bed, I quickly jumped into her wardrobe and closed the door so that only a narrow gap allowed me to see out into the bedroom. By a strange stroke of good luck, in my carelessness I had left the door unlocked when I came in which meant the last turning of the key had left it locked. This extra few seconds was just the time I needed as I had barely settled into place when I heard footsteps in the bedroom door and then saw through the gap in the wardrobe the sight that I had been dying to see. Barely a couple of feet away from me, so close I could touch her if I opened the wardrobe door, stood the world's sexiest woman. She wasn't dressed in an expressively sexy way right now, unlike the look she had at the concert earlier on. Now, Britney was dressed in some of the more casual clothes I had seen in her suitcase, pale blue sweatpants tied with a yellow tie and a blue top over a yellow t-shirt. Her beautiful golden blonde hair was mostly covered by a matching blue and yellow LA Lakers baseball cap with the brim pulled low to cover about half of her face. Dressed like this, she could almost be just any old member of the public, almost. There remained a certain confident sexiness about her that could only belong to a star. Frankly, if my evening had ended with just this closeness to my favourite celebrity this would have been enough to make it endlessly memorable. However, I got more because now things began to live up to my wildest hopes for what this evening could achieve. Britney took off the blue and yellow baseball cap and threw it onto the bed, shaking her blonde hair free so I could now see all of her beautiful face. She pulled the blue and yellow top over her head to reveal beneath that toned midriff that so many people had written about and, above that, those beautiful round breasts. Best of all, her breasts were still covered by the extremely sexy pink bra she had worn to perform the concert earlier on. She must have just thrown on the sweats over the top of her costume, my mind was now working a mile a minute, this meant that she wouldn't have showered back at the concert venue so may be about to now, in which I case I would get to see her strip. Carefully, I pulled out my camera from where it lay beside me and began snapping pictures, desperate for the clicking of the camera not to be heard by Britney. She kicked off her trainers, tossing them over to the other side of the room, I was right, she was no neat freak, before pulling off her sweat pants to reveal, how delightful it was, the pink hotpants and stockings from earlier. Britney Story At this point, I realised that I was still holding in my hand Britney's red lace panties that I had stolen from her suitcase. I raised them for another sniff, still snapping photographs as Britney turned her back away from me. She reached behind her for the ties of her pink bra. I had to restrain myself from reaching out myself to help her out of it. Britney let the bra fall as she turned back to face me and I was given a sight few people have seen quite this close up, the stunning, pert breasts of a pop superstar. I have to admit, at the sight of this stunning moment I let out a little gasp of surprise and pleasure. In a split second, Britney was alert and aware that something was not quite right. She stepped right towards the wardrobe, right towards where I was hiding, and flung it open. Now it was Britney's turn to give a gasp of shock. I don't blame her, after all what must she have seen? A crazed fan, sitting in her wardrobe watching her undress as he snapped photos with one hand and smelt her panties with the other, all the time with a growing hard-on visible under his jeans. "Who the hell are you, and what are you doing in my wardrobe?" said Britney, partly angry, partly a little scared and confused, "Hurry up or I'll call security." "I'm Rich," I told her, "I'm a fan, I was at your show this evening." This didn't seem to reassure her. "Listen Rich," Britney said, trying to sound reasonable, which in the situation was pretty impressive on her part, "I appreciate you dedication as a fan but you know I can't have you taking those photos of me." "Why not?" I found myself saying almost against my will, "There's loads of nude photos of you on the internet." Britney seemed momentarily taken back by my forwardness, I know I was. "None of them very accurate, I can assure you," she said, "Anyway, you know this is different, seedy photos of me stripping in a hotel room, there'd be a riot of scandal." I began to realise now that despite her confident façade, Britney did not really have the upper hand here, she was desperate for those photos not to be revealed and, although it was cruel, I was beginning to wonder just how far she'd go to get them. "I'm sorry Britney, but these pictures are something I'll always treasure, a little something of you." As I had thought, Britney now dropped her confident, reasonable exterior and put on a pleading face so beautiful it was all I could do to not melt right there. "Please Rich," she begged, "You must realise, as a fan, the damage those pictures could do to me," with some difficulty I remained unmoved, "Please, if you give them to me I'll do anything for you." This was now my opportunity, "Well, there is something you could do for me," I said, indicating the bulging erection that remained in my trousers throughout this conversation, Britney's pleading had done nothing to diminish it. Britney frowned at the sight of it, "Don't be disgusting," she said angrily. However there wasn't much conviction in her voice, and a little twinkle in her eye told me that maybe she didn't really find this such an objectionable thing to do to get her photos back. "Come on Britney," I said, knowing she probably just needed a tiny bit more persuading, "All you need do is suck me off and then we're even, I'll give you the photos." I could see a moment's doubt and hesitation in Britney's eyes, that same moment's doubt my sister used to get when you were trying to persuade her into something, it meant she was about to give way to you. "Well, as long as you know I'm only doing it for the photos," Britney said, and I knew she'd cracked, "I don't even find you remotely attractive so don't get any other ideas." A little lick of her lips suggested that the truth might be otherwise. Britney dropped to her knees before me and unzipped my jeans, dropping them to the floor and releasing my cock, which stood proud and erect in her face. She licked her lips again in a way that was making me ever more horny, before running her tongue around the tip of my cock where some pre-cum was already emerging. As her tongue flicked over the tip of my member I felt a thrill of excitement, a couple of months earlier all I had wanted was to see her in concert, now the world's sexiest pop star was on her knees in front of me, taking my dick in her mouth. Rather unenthusiastically at first, Britney began to suck on the head of my cock like it was a lollipop. However, before long some baser, more sexual feelings, began to override her earlier reasoning and she began to suck me off with gusto, using her hand to jerk off the base of my cock while her tongue ran eagerly around the head. As I looked down into her beautiful, sparkling blue eyes, I could see that Britney Spears was now loving getting my cock inside her throat, she even let out a moan of pleasure. All those nights of fantasy and this is finally coming true I thought, amazed, the woman of my dreams is actually sucking me off. That thought was enough to finish off what Britney's skilled and eager cocksucking had begun and I cried out loudly, forgetting the security people no doubt waiting outside, "I'm cumming, Britney! I'M CUMMING." Britney swallowed a couple of mouthfuls of my creamy juices, before pulling my dick out of her mouth and jerking it off some more as I continued to spunk onto her face and her beautiful breasts. It was quite something of an orgasm, I can tell you, just like all those I had had when I fantasised about her except a thousand times better. By the end of it, Britney was slightly drenched in my juices. She licked her lips once more, this time tasting some of my cum with it in a way that had such relish to it that I was already getting horny again. Britney stood up and pulled me close to her, not worrying that her sticky body was getting my cum all over my clothes. She opened her pretty pink lips and I leant over to kiss them, pushing my tongue into her mouth in the way I dreamed of pushing my cock into her pussy. I could taste my salty cum on her mouth but I didn't care. After all, why would I, I was passionately french kissing Britney Spears. After what was an age but seemed to me regrettably short we broke from the kiss. "Now don't say you didn't enjoy that, Britney," I said to her, the silly grin on her face telling me enough about her feelings on the matter. "Well worth a couple of photos though, Rich," she grinned at me. Now I knew how sexually suggestible the beautiful star was I decided to try and push my luck further, after all this kind of thing is a once in a lifetime opportunity (or never in most people's lifetime). If she'd give head for some photos, I reasoned, what would she do for videotape. Now, I didn't have a video camera, although right now I'd have loved one, but Britney didn't have to know that. "I'm sure that video will make a great hit on the net," I said. Britney, who had been wiping my cum off her breasts, looked up at me surprised with a moment's fear flashing across her eyes. "What video?" she said. "The one I set up in here earlier on, the one that just filmed you giving me head," I said, thinking on my feet, "Since you were such a good girl with the photos, how about a similar thing with this. I'll let you have the videotape if you let me fuck you." I had expected the former surprise and slight anger followed by either me persuading her as before or her angry dismissal of me. What I didn't expect was tears, but that's what I got. Tears began to roll down Britney's smooth cheeks, mixing the salt of her tears with my salty juices. "I...I can't," she stammered, unhappily, "You don't know how much you're asking of me." I was now beginning to feel sorry for her quite a lot but still I said, "But it can't be that old nonsense about you being a virgin, nobody believes that. A virgin doesn't give head that good," I smiled hoping the compliment might merit at least a further smile back. I didn't get one, the tears continued to flow heavily. Britney sat down on her bed, still beautiful but now in a tragic, pathetic way. Her breasts exposed, dressed just in pink hotpants and fishnet stockings, tears streaming down her face. Now I felt really guilty, this was the woman I had always loved and worshipped from afar and I had made her cry rather than bringing pleasure to her. I sat down on the bed beside her and put my arm around her bare shoulder, giving her my shoulder to cry on, my shirt was already ruined by my cum stains anyway. Quite a pair we made, her topless and me with my cock out. "I'm so sorry Britney," I said, utterly sincerely, in fact tears were almost welling up in my eyes, tears of sympathy for her, "I didn't mean for you to cry. I just thought...I just thought that we had hit it off quite well and you enjoyed sucking me off, I thought you'd like the feel of me more inside you." "I'm sorry Rich," she said between sobs, "It's not your fault, it's just something I can't do." I patted her on the back, further trying to comfort her. "Listen Britney," I said, "We don't have to do anything if you don't want, I'll destroy the tape," my one little lie, I thought she'd be further upset to know of my deception on that count, "I just wanted to make you happy, make you have fun. I'm your fan Britney, I love you and I only want to have sex with you if you'll enjoy it. I can always go back to jerking off over your picture." Britney looked up from crying on my shoulder, the tears had stopped, she even smiled at this last reference to my pathetic fan lust for her. There was a moment when she looked into my eyes and seemed to be deep in thought before coming to a decision. "I've something I need to show you, Rich," said Britney, getting up from her place beside me on the bed, "If you still want to, once you've seen it, I'd love for you to fuck me." With that, Britney Spears, every man's fantasy began to strip off her bright pink hot-pants. I leant forward, eager to see her pussy beneath, and then reeled back in shock, silent and open mouthed as between the shapely thighs of the world's sexiest star was not the smooth shaved pussy I had dreamed of but a throbbing, manly cock. 3. I'm Not a Girl, Not Yet a Woman As you can imagine, the sight came as quite a shock to me. My eyes practically popped out of their sockets and my mouth dropped open at the sight before me. Britney Spears, America's sweetheart, the world's sexiest superstar, the woman I had spent the last five years lusting after, was no woman at all. Sure, she had those fine round breasts, long legs, curvy feminine body, but between her legs, as she had just revealed to me, was a very masculine penis. Let me assure you, my mind was spinning with a million thoughts all of a sudden the moment Britney dropped her tight bright pink hot-pants to reveal her little secret beneath. This was not just the woman of my dreams, this was the woman who, in real life, had just got down on her knees and sucked off that part of me that I now discovered we shared. The first thing that flashed through my mind was severe doubts about my sexuality. I'd always been a red blooded male, and I'd felt my obsession with Britney Spears was one thing that proved that above everything else, and here I was, having been sucked off by a chick with a dick, never mind that she happened to be Britney Spears, and having enjoyed it immensely. Now, having enjoyed sexual contact with someone who isn't all woman is enough to make anyone doubt their own sexuality, but remaining really turned on by the situation even after discovering this fact made me even more so. On the other hand, here I was with a chance to fuck Britney Spears, something any man would kill for, I couldn't turn it down. I mean, it was Britney Spears standing there in front of me, dressed in nothing but a pair of fishnet stockings, her hair dishevelled and make-up smudged from sucking on my cock, her beautiful breasts sticky with my cum. There were still tears in her eyes and her head was hung so she was no longer looking at me, but she was still undeniably more hot and sexy than any woman I had ever been with before. I'd be an absolute idiot to pass up my chance to get my cock inside Britney Spears, the part of me that wasn't so worried about my sexuality was thinking, even if she does have a cock herself. Certainly this was the part of me that was ruling my dick, as it had already grown fairly firm despite my having came all over Britney just a few minutes earlier. Gradually, this part of me began to take over and I knew that what I really wanted was to consummate my lust with the beautiful star, consummate that desire that wouldn't go away no matter what was between her legs. I stood up and walked over to where Britney was standing, naked, waiting. She looked up into my eyes, there was a look of hope and anticipation on her face, willing me to overlook any lingering doubts and to fuck her right there. Well, that beautiful, pleading look in her tearful eyes sealed it, I was going to fuck her, not just for my own pleasure but for hers as well. I took Britney's head in my hands and pulled her lips to mine, repeating once more the passionate kiss of earlier. I invaded her mouth with my tongue and caressed her tongue with it. My hands moved around to the back of her head as I pulled her closer to me. Once more there was a lingering salty taste of my juices on her beautiful pink lips, but I didn't care, in fact this time I savoured the taste and how it combined with the delightful taste of her mouth. As I pulled her close, I could feel Britney's cock rubbing against mine and, I'm slightly embarrassed to admit, this contact caused an eager twitch of pleasure and anticipation in my own member. When she had taken her pink hot-pants down to show me what was beneath, Britney's cock had been quite soft and flaccid, barely semi-erect, but now this close embrace and the contact with my cock had made hers grow pretty stiff as well. Breaking from this embrace, I began to kiss and lick down her elegant neck towards those two perfect round breasts, I don't mind telling you by now I was in total heaven and the surprise package between Britney's legs was bothering me less and less. I tasted my cum once more as I proceeded to lick Britney's breasts clean. This was, of course, simply an excuse to run my tongue over every inch of Britney's most prized asset, but as I did so, I was further able to savour and enjoy the taste of my own juices on her soft skin. By now, Britney too was beginning to abandon her reserve and her worries and starting to simply enjoy herself, letting out girlish little groans as my tongue flicked her erect nipple on and off like a light switch. Britney's cock was now standing erect and proud, thrust forward incongruously from her soft feminine body, she was obviously very excited. Britney pushed me back from sucking her nipples and gave me a wicked grin. "Are you going to keep sucking on my nipples like a little boy?" she said, "Or do you want to fuck me like a real man?" Well, as you may guess, I needed no more invitation than this to get my dick inside the world's most desirable woman. I kissed her once more on the lips and ran my hands down her back until they were clutching her fine pert arse. I picked her up, still holding her arse, I was never very strong but Britney was pretty light, and carried her over to her sumptuous, king-sized double bed, sweeping her open suitcase out of the way. I threw Britney down onto her bed and she looked up at me with an eager twinkle in her eye. She opened her stockinged legs to show me a little of her arse and smiled up at me. "Come on then, fuck me Rich, fuck my arse like I've never been fucked before." I took her long legs in their fishnet stockings and pushed them further apart to allow me better access into her arse. I put her feet up on my shoulders, lifting her arse up to allow me entry, and placed my hands on her wide hips. Slowly, I pushed my now totally firm, hard cock inside her arse-hole. It was pretty tight, a lot tighter than any of the girls' pussies I had fucked in the past and I was a little worried, as I forced my cock up inside her, that Britney was in pain. When she let out a little moan, I stopped thrusting my cock inside her but she looked up at me and said: "Don't stop now, Rich, I'm really hot and excited and I need to feel all of you inside me, NOW." At this I held her hips and thrust the whole of the rest of the length of my cock up inside her in one fast, hard thrust that had Britney crying out "Oh yes! That's it!" Taking this as my cue, I withdrew my cock part way from inside her before thrusting it back in even harder than before as she pushed her arse to meet it. "Oh God yes, Rich, don't stop!" Britney moaned. So I didn't, in fact I started to fuck her arse hard and violently in a way that caused Britney to scream out so loud that I was momentarily worried that her cries might bring in her security people. While I was fucking her arse, Britney began to stroke and caress her beautiful round breasts, before she began to stifle her cries into moans by stuffing her breast into her mouth and sucking on it as I had done just a little earlier. Tears were now streaming down her face once more, but this time I was sure that she was crying tears of exquisite pleasure. Her free hand that wasn't massaging her own breast reached down her body to her rock hard cock. As I thrust hard and deep into her tight arse, my body slapped against her throbbing member and, if anything, this was even more of a turn on, she now began to stroke her hard cock in time with the thrusts of mine deep up inside her. My head was spinning with the joy and excitement of the moment, the fulfilment of all my fantasies of previous years combined with the thrill of new discovered joys. Here I was, fucking the gorgeous Britney Spears in her tight arse and it was everything I'd dreamt fucking her would be like and better. I'd never fucked any girl up the arse before and I knew now that I would struggle to do anything but in the future, the tightness of her little arse-hole constricting on my cock felt amazingly stimulating. Added to all that was the even newer joy of her own hard cock, which had made me, hesitant before but now fascinated and excited me. It won't surprise you to know that with all these pleasures and stimulants going on, it didn't take me long to blow my load, even though I had cum bucketloads all over the pop superstar not much earlier. "I'm gonna cum," I yelled out to Britney, feeling it boiling up inside me. "Don't stop now," she moaned, taking her breast from her mouth, "I want to feel you explode inside me, I want you to fill me with your juices." And that was it, with a grunt I thrust back into her one more time and my cock began to spew out its creamy white juices up inside her. As I continued to cum deep up into Britney's arse, she stroked off her own cock with increasing vigour and enthusiasm and, sure enough, a few seconds later I saw her cock shoot forth a similar load, spraying her juices across my chest and hers. By this time I had withdrawn my cock from her arse, that was now leaking my translucent cum, and continued to wank off over her, as she did over herself. Not long afterwards, I lay beside Britney on her large bed, both of us now totally naked except for the fishnet stockings that she continued to wear, and both of us soaked and sticky in both our own and each other's cum. Britney ran a finger over my glistening, sticky chest, coming off it with her finger dripping with the mixture of our juices. Slowly and languidly, she inserted the wet finger into her mouth and began to lick it clean like a lollipop, savouring every moment of it. Finally, she finished licking her finger clean and removed it from her mouth. She smiled a pearly white grin at me and said: Britney Story "That was delicious, how would you like to try some?" Put like that, and coming from that gorgeous face, how could I refuse? Seeming to take my acceptance as given, Britney ran the same finger across her own hot glistening body, scooping up another load of our mixed cum. She held the finger out to me and I bent my head towards her and began to lick her finger clean, at first just lightly licking, before taking her whole finger in my mouth. I was beginning to understand why Britney enjoyed this so much, every time I tasted cum, it seemed to taste better and better and I savoured it more and more. Was I turning into a sissy? Well, one look at the gorgeous, desirable, if surprisingly well hung, woman lying beside me would confirm me in my masculinity. However, it had been going through my mind that Britney must have once been entirely a man, how and why had the transformation into the hot, and frankly very femininely so, woman that the whole male world lusted over happened? I decided the only thing to do was to ask her. "Britney, can I ask you something personal?" I said, turning to her as we lay naked together on her bed. "Sure, Rich, go ahead," she smiled, now the friendly, charming, Southern girl we all knew from her TV interviews, miles away from the hot, horny shemale I had just fucked. "How did you become, you know, the way you are? Britney smiled again, this time slightly wearily. "It's a long and quite personal story," she said, "But since you're the best fuck I've ever had, I'll treat you to it." And she did, telling me all about how she went from being a small, confused young boy in Louisiana, all the through to being Britney Spears, international superstar and sex symbol. 4. Boys "As a child I only ever had two ambitions," Britney said, beginning her story, "One was to be a successful singer and the other, to be a beautiful girl. Now, for most traditional southern families, to come out with a wish like that would have been met with anger and disbelief. After all, all the families that lived around me wanted to raise red blooded American sporty men and so to have your four year-old son wanting to be your daughter would not be tolerated. At best I could probably have hoped for my desire to dress and act and become like a girl to be treated as a childish phase for my parents not to take seriously. But it was different for me, thankfully in this, as in so many other things in my life, I had the total support of my mum who did everything in her power to make things easy on me as a confused little boy wanting to be a little girl. I know now how hard this must have been for her, but she cared so much about me that all she wanted was for me to be happy. 'I always wanted a daughter anyway,' she would say, this was, you must remember, before the birth of my baby sister. So it was that, thanks to my mum's tireless efforts, I started at school with a wholly new identity, little Britney Spears, the cute all-American girl. I don't know what strings my mum pulled, but she made sure that all my teachers and, particularly, my classmates never knew that I was anything other than I seemed, a nice little girl. Because of this, it wasn't difficult for me to adapt easily to the life I had now chosen for myself, the life of a girl. After all, if everybody treated me as one and I felt like one then I could easily ignore the evidence of my body. "With my ambition to be a singer, my mum was equally supportive and helpful. As soon as I was old enough to belt out classic songs, she entered me into all kinds of talent contests, most of which I won. As you probably know, the result of all this desire and ambition was to get me into the Mickey Mouse Club. The years that I spent doing that were possibly the best years of my life so far. I was able to fulfil my dream and be a singer and performer, and do it all on TV, and I was with lots of other kids who shared at least half of my dreams and desires. Nobody ever wondered if I was ever anything but what I seemed and so I never worried about fitting in. At school, I felt a little excluded more because of my precocious talent and ambition than because I was a boy masquerading as a girl. So, in the Mickey Mouse Club, surrounded by kids just as talented, I felt like I was among my own sort of people. "I was devastated when it all ended with the Mickey Mouse Club, not just because I had achieved my dream of being a singer only to have it snatched away from me, but also because this marked the end of a time in my life when I was totally comfortable in myself, probably the only time that was true. As the show ended, I was entering adolescence and with it came the realisation that I wasn't really like the other girls who began to fill out with curves while I remained skinny and flat chested. I'd been taking female hormones to make me more feminine and anyway I still made a very pretty girl, one of the most desired by my high school's boys, but I didn't have the round breasts that I saw on other girls and this made me constantly aware of my difference. Not that I let this insecurity show, on the outside I was still one of the most popular, prettiest girls around. I wanted desperately to have surgery to make me more of a young woman but here my mum couldn't help me, my family were kind of poor and we didn't have anything like the money needed to pay for surgery. "Then, out of the blue, came the answer to all my prayers. Ever since the end of the Mickey Mouse Club, I had been trying to get myself a record contract to carry on my dream of singing, either as part of a girl group or on my own, and now I had an offer. From there on, everything was a crazy whirlwind of activity as I got on planes and flew to New York to record my debut single and, hopefully, to become the singing star I always dreamed of being. The song was a brilliantly written piece of danceable pop called Hit Me Baby One More Time. I loved it even then, I began to sense that this could be it, this could be the answer to both my ambitions. Of course, you know what a huge hit the song was all around the world. A massive hit boosted by the sexy video. I came up with the schoolgirl video idea myself. At the time, I was growing accustomed to the further uncomfortable confusion of my growing sex drive, as a girl I thought I should be attracted to hunky men but it turns out I was finding myself attracted to almost everyone. But I knew that I couldn't give in to my sexual urges, not without revealing too much of myself. So, I wanted to do a really sexy video, kind of a fantasy, with me as a sexy schoolgirl. After all, if I still was all man in my body, I could at least flaunt myself as a girl, that would make me more confident in my femininity and would release some of those pent up sexual urges. Because I was still, in essence, a man, I had no breasts to show off so you can see how the schoolgirl outfit doesn't really show any of that, it's more concerned with showing off my bare midriff which has always looked this good." At this point in Britney's story, I couldn't help but think back to all those days I had spent watching this sexy schoolgirl video and lusting and fantasising over the singer, all that time I had been desiring a man. "So was this desire not to reveal the secrets of the real you the reason why you didn't want to give up your virginity for so long?" I asked her. "I didn't want to keep my virginity for so long," Britney continued, "But I did feel it was necessary to do so. If I had given in to all my urges and desires and just had sex with the first person I felt attracted to, then I was sure that person would go straight to the press and sell their story and then my secret would be aired across the world. So I felt I had to wait, wait for someone that I felt loved and wanted me enough to want to fuck me no matter what was beneath my skirt. That's why I decided to make very public my belief in not having sex before marriage. It wasn't any kind of moral choice, as you probably can tell I'm a very sexual person, more a pragmatic one, and when I decided to go against my no sex before marriage promise, things only went badly. But that's getting a little ahead of myself. "The huge success of Baby One More Time not only established me as a pop singer with a bright future but also gave me the money to fulfil my other ambition truly and pay for the surgery I so desired. So, I faked an ankle injury to get some time out to have the surgery done. Aided once more by my ever-helpful mum, I found a surgeon who could be trusted and heavily paid not to reveal anything personal. I finally had breasts, and what perfect breasts they had given me, just the size I had always wanted. I had lots of other more minor surgery, trying to make me look more like a woman but stopped short of full-scale gender re-alignment. My cock was the source of all my sexuality, all my desires. Although it could prove embarrassing or uncomfortable, I couldn't do without it, it was a part of who I am. Anyway, the surgery I had eventually resulted in the beautiful creature you see now lying beside you." I had to compliment her surgeon. I knew from the Baby One More Time video how great she looked as a woman with just make-up and styling, but still her surgeon had made her even more perfectly so. In particular, those pert, round breasts were better than any that I had ever before seen on a natural woman. "When my next video came out, for Sometimes," Britney went on, "a lot of the press noticed something different. The fact that I now had breasts didn't pass them by and there was lots of speculation and discussion over whether I had had breast enhancement surgery or whether I had just grown into them naturally. As if you could get tits like this naturally! Anyway, in all that speculation, not one person hit on any broader implication of this. Of course, I denied having any kind of surgery, but secretly I was pleased that the press should think themselves so clever to have spotted that but were totally missing the bigger picture. "When I had first been starting out, I had got to go on tour as a support act for Nsync. It was here that I met up again with Justin Timberlake who had been one of my best friends in the Mickey Mouse Club days and had now grown into a fine, attractive young man. It surprised nobody when, soon after this, we started dating. Of course, Justin was no different from your average man in his early twenties; most of what he talked and thought about seemed to be sex. Of course, I was a beautiful woman in my early twenties so sex was on my mind quite a lot too, but I was still too worried about what Justin might think if he knew the real me. So I maintained the pretence that I wanted to remain a virgin, which was pretty tough when pitched against the constant pressure that the horny Justin put on me to do it and my own strong desires and urges. "Another incident around this time also put a strain on my attempts to remain a virgin. I got a call from another former Mouseketeer who had just got a singing contract and a record about to come out, Christina Aguilera. She had seen and admired the success that Baby One More Time had given me and called up asking to come over to my place and wondering if I had any advice to offer her. I was always happy to help a fellow Mouseketeer and the company of a beautiful young woman just helped matters further. Anyway, Christina came round and I told her everything I knew and felt about the music industry from my brief success that far as a pop star. Christina was very grateful for all my advice. So grateful in fact that she felt vocal thanks weren't enough and had to express herself physically. This was before the outlandish hair and make-up that she has adopted these days, all she was then was a very pretty blonde girl with piercing blue eyes. Christina took me in her arms and kissed me on the lips. I had expected a brief thank you kiss, her lips brushing against mine for a fleeting moment, but this was nothing like that. She pulled me close to her and locked lips with me, slowly inserting her tongue in to explore my mouth. My eyes registered first surprise, then pleasure at the delight of kissing another girl. Christina began to pull the top that I was wearing over my head and that's when I realised that if I didn't do something there and then, she would want to go all the way and so would discover more about me than I wanted her to know. So, standing there in my bra and skirt, I had to tell her no, that wasn't the kind of thing I wanted, even though in my heart, and in my groin, I knew that it was. Christina's face fell with disappointment, I could read in those bright blue eyes that she had been really into it and had been able to feel that I was too, that why she was so hurt by my rejection. Things haven't been the same with us since, ever since then we've been massive rivals rather than friends, although whenever we meet there's just this huge sexual tension between us. "Anyway, after the Christina incident, I felt that I couldn't go on doing nothing to satisfy my incredible sexual urges. So, I began by giving Justin head, soon becoming pretty expert at sucking off his cock so that, for a while, Justin didn't mind that I had promised to go no further with him. But, after this had gone on for a year or two, he started pressuring me once more to do it for real with him, and I began to wonder if I would lose him if I didn't. Besides, me and Justin had been together for a long time and we were so in love, I felt like I could probably trust him by now, that he would understand me and my secret. So, one night like any other, I revealed myself to him. He was shocked, which didn't come as much of a surprise to me, probably even more shocked than you were earlier on, after all, he thought he knew everything about me. Anyway, he seemed to understand, and that night we had such a wonderful night of passion as Justin took my long desired cherry, fucking my arse in a way that sent me to heaven. This was way better than anything I had ever dreamed it would be, and I'd had some pretty hot dreams. "Unfortunately, this night was the end rather than the beginning of my magnificent sex life with Justin. It wasn't long after this that he came to me to say that it was over between us. That night when he had fucked me, he seemed to be really into it, really enjoying it, but now he seemed to worry about his masculinity. He told me that he had found himself a real woman who would see to his needs in a way that I never could, I later found out that this was Cameron Diaz and that Justin had gone running to her after our night together. "After my break up with Justin, I was devastated. He was the only man that I had ever loved and I had felt sure that if anyone were to understand me then it would be him. I don't think I will or can ever love anyone so unconditionally as I did him. For a long time after that, I felt depressed and sexually repressed, I couldn't share my secret with anyone and I had no serious relationships until Kevin now. Kevin knows the truth about me and he stays with me. I don't know how keen he is on the idea, he doesn't fuck my arse, but he does enjoy me giving him head, and he loves the attention and envy he draws being Britney Spears' boyfriend. So I guess I'll have to settle for that, it's been so hard to find a man who understands and who wants a serious relationship." She was referring here to Kevin Federline, her former dancer who she had recently started dating when I had my encounter with her and who has since become her husband. I have to say, I felt for Britney's pain and loneliness. She was one of the biggest, most popular and most successful stars in the world, millions of men desired her, and it seemed that all her dreams had come true. Yet, at heart, she was just a lost little girl who had been trapped in a man's body and she yearned for someone to understand and love her. I've got to admit, having heard this much of Britney's life story, I was curious about some things and had to ask her some more. "So what about all the other men you've been linked with?" I asked Britney, "What about your marriage in Vegas?" Britney sighed and said, "Jason had been a friend of mine from back home, we had known each other for years. I was still depressed at the thought that I would never find anyone to understand the real me and I began to feel that maybe someone I was that close to, someone I had grown up with, might just be the one. One drunken night in Vegas, I managed to convince myself that this was true and demanded that we get married that very night. Of course, Jason jumped at the chance, but when it came to the wedding night and he saw fully what he had married into, he ran a mile and the marriage was effectively over from there." "What about the other guys?" I said, "What about Fred Durst or Colin Farrell?" "Fred Durst?" she laughed for almost the first time all evening, "I may be lonely but I do have some standards. Anyway, I don't think he'd be that keen on getting to know the real me. As for Colin, he was keen, definitely. And he was great, up until this evening, I'd have said that the night I spent with Colin was the best fuck I have ever had. But Colin isn't the kind of guy that you can tie down to anything, he isn't ever going to settle for a serious relationship with one woman, especially one who isn't all woman," here she smiled again as if fondly remembering that night. I felt absolutely flattered and delighted to hear Britney add the words "up until this evening" to that last sentence, could it possibly be that the best evening of my life was also one of the best of hers? Whether or not this was the case, I had never felt closer to Britney than I did now having heard her tragic story. I really felt for her and I knew now that there was something I had done to her, something that I now felt particularly guilty about and had to get it off my chest. "Britney," I said, "There's something I need to confess to you," I paused for a moment as she looked at me with confusion, wondering what I could be about to say, "There never was any videocamera filming you sucking me off. It was a lie to try and get to fuck you. I'm so sorry, I didn't ever guess any of this when I did it. I didn't know you like I do know. I'll do anything to make it up to you." I had been worried that Britney might burst into tears once more, or, worse, throw me out of her room or report me to the hotel and lose me my job, or even to the police. What she did, however, was smile, a smile not unlike the one she had given me when I first suggested she suck my cock, a smile that suggested wickedly kinky thoughts were running through that beautiful blonde heard of hers. "Well, I'm sure we can find some way of you making it up to me," she said. 5. Born To Make You Happy Britney smiled at me in a wickedly seductive way, I wondered what was going through her mind as she told me that she was thinking of some way for me to make it up to her. I had done something pretty serious in blackmailing her into sex with made up video footage of her sucking me off, she'd be well within her rights to do anything to me. However, she appeared to be thinking of something pretty sexy, we'd hit it off pretty well and I kind of felt Britney's forfeit for me would involve something more fun and sexy. I had thought that I was really in love with Britney before this evening, with the Britney I had seen in videos and interviews. However, I was now far more in love with the real Britney, the Britney who had let me fuck her in the arse, the Britney who had poured out her tragic and emotional life story to me and had made me pity her as much as I wanted her. She had made me feel that I would like to do anything for her, do anything to make it better, to make her happy. So, whatever it was that Britney was thinking of that I could do for her, I was more than happy to do it. She'd made me experience greater pleasure than I thought possible and now there was nothing I wanted more than to do the same for her.