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Oops, I Did It With Britney

By: 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.

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.


Oops, I Did It With Britney Pt. 02



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:

"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.




Oops, I Did It With Britney Pt. 02



"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.

To be continued…



Oops, I Did It With Britney Pt. 03



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.

Britney was still naked, her beautiful, curvaceous body stretched out on her bed in front of me all through telling her story, wearing nothing but fishnet stockings. There were moments of her story that were really hot and had me getting turned on a little. Even despite two orgasms already this evening, my naked cock was already becoming quite firm again. Obviously, the arousing recollections of her past experiences with Justin and Christina were having a similar effect on Britney and her own member stuck out from her smooth body, hard and erect and crying out for relief. Britney reached her hand down to her cock and licked her lips, before speaking to me:

"You used your pretend camera to get sexual favours from me," Britney said, "It's only fair I to make it up to me you service me a little. You know, despite my abilities at cocksucking, I've never had somebody else give me head."

I was, I'll admit, a little surprised and taken aback by this, what should I have expected though, really? I had after all offered to do anything for her and, let's face it, when I said that, sexual favours weren't exactly the furthest thing from my mind. So this request shouldn't have come as a shock, particularly after her story, but I hadn't quite yet managed to square my fantasy feminine Britney with that part of her anatomy that I was now staring at and that was decidedly masculine. Still, that didn't mean that I wasn't attracted by the proposition. Britney said that this was something that she'd never done before and she wasn't alone in that, if nobody had ever given her head before then you'd better remember that I'd never given it either. I have to say, the prospect of doing something sexual, whatever it was, to Britney Spears for the first time filled me with excitement and arousal. Just think of all those people, and I was definitely one of them, who'd fantasised about deflowering her when there was all that publicity about Britney being a virgin and then you'll know how I felt right then at the prospect. I'd said that I would do anything for her and I would, right at that moment making her happy was my main concern, although I wouldn't be averse to something that would make me happy at the same time.

As her story progressed, I'd found myself putting myself in her shoes, wondering what it would be like to have been Britney, to have lived through all those experiences. The way she looked when she talked about her first sexual experiences, when she talked about sucking Justin's cock, there was a twinkle in her eyes and a twitch of arousal in her cock that made me wonder what it would be like to be her, what it would be like to be there on my knees, taking a hard cock into my mouth and sucking on it. I have to confess that for a fleeting moment the thought was a real turn-on and now those thoughts came flooding back into my head and I was becoming pretty excited by the possibility of trying out what it would feel like. I smiled at Britney and in tat smile she could obviously sense my acceptance of what she asked me to do. Her face was filled with a sparkling white smile and she leapt up off the bed and clapped her hands together like an over-enthusiastic child, bouncing up and down in a way that made her pert breasts and hardening cock bounce around with her.

"You'll do it," she said excitedly, "I can't believe this is actually happening" (believe me, Britney, neither can I, I thought) "You're the greatest guy ever."

With this, she threw her arms happily around my neck and covered my face with kisses. Any doubts or worries that I had about doing this evaporated in that moment when I saw how thrilled even the thought of it made her. Her enthusiasm was rubbing off on me, meanwhile her cock was rubbing against mine and stirring some fierce longings in me. Slightly reluctantly, I unwrapped Britney from around my shoulders and gave her a quick kiss on the lips.

"Lie back down and open your legs," I said to her, "And I'll try and give you all the pleasure you give me."

Smiling obediently, Britney lay back down on the bed, stretching the whole of her beautiful body out in front of me, her breasts and cock protruding up enticingly from her flat waist. With her legs dangling over the edge of the bed, and her feet resting on the floor, Britney opened up her stockinged legs and allowed me to kneel down on the floor, my head between her smooth thighs, my lips inches from her cock.

"Bear with me Britney," I said to her, "I haven't done this before so I might not be very good at it."

"Less talk," she replied, "Just suck me off."

Although I'd never done this before, I had some idea of what I liked when girls sucked my dick and I think I'd been given some insight into what Britney liked and, in having Britney suck me off earlier that evening, I'd had the privilege of a masterclass from a true expert cocksucker. So, I kind of felt like maybe I could know a little what I was doing. I didn't want to go straight for her cock, enticing as it increasingly was. For one, I wanted to tease her a little, draw out the pleasure for her, but I also just didn't feel confident enough in my cocksucking skills to go straight for it. So, I put my lips to her thighs and began to give her little kisses, soon extending my tongue to give little flicks of it around her thigh, moving ever closer to her cock and balls. Meanwhile, I felt with my hand to find her ever more firm cock and began to stroke it. I knew this would be easier than moving straight to having it in my mouth, it wasn't after all that different from stroking my own member. As I slowly stroked my hand up and down Britney's cock she gave a moan of appreciation which told me that I must have been doing something right.

This appreciation stirred me on to wanting to do more for her, wanting not just to hear her moan for me but to scream and yell with orgasmic pleasure. So now, I moved my mouth towards her awaiting cock. I continued to stroke Britney's shaft as I extended my tongue to touch lightly against the base of her cock, just where it joined her smooth, shaved balls. I felt a momentary thrill and stirring of excitement at this, my first taste of Britney's, or any, cock. My own was now growing almost as hard and erect as hers. Languidly, I ran my tongue up the length of her shaft towards the head, as if licking delicious ice cream from a spoon. I got a great taste like that now, as my tongue flicked over the swollen purple head of the pop superstar's erect cock. I put my lips to it and kissed, opening my mouth to take in some of the salty taste of her pre-cum. Britney moaned again with pleasure and, possibly, a little impatience, willing me to get on with sucking her cock.

Here goes nothing, I thought, and opened my lips further to allow the head of Britney's cock inside me. "Oh yeah, that's it," came her moan, encouraging me to go further. I'd had girls take all my cock into their mouths without any seeming effort, hell Britney earlier was one of them, and, in watching porn, I'd seen them swallow cocks twice the size of mine, but for me this first time it wasn't as easy as all that. I opened my mouth and took in the first couple of inches but that was all, my mouth was completely full. For the first time the thought "how do those girls do that?" occurred to me. Even being able to take less than half of Britney's member in at first, I continued to pleasure her as best I could. Caressing the head of her cock with my tongue, I tried to relax my throat to allow me to draw more of her cock inside my mouth without gagging, all the while continuing to further stimulate her by stroking my hand up the rest of her exposed shaft.

"Fuck yes," Britney moaned, impassioned, her head thrown back on the bed, "God, this is amazing."

With some persistence, I had managed to get most of the length of Britney's cock inside me and, let me tell you, even though my own cock wasn't even being touched, it was one of the best, sexiest moments of my life. I mean, here I was, feeling closer to my ultimate fantasy girl than I had ever thought possible, even to being joined with her, to feel a part of her inside me. Her cock felt warm, throbbing, excited, alive against my tongue. I didn't want this exquisite moment to end but I longed to feel Britney squirt her juices into me, down my throat.

"Come on Rich," Britney encouraged, "Suck me like a cum hungry slut."

Hearing these filthy words come from the beautiful mouth of the not that innocent superstar was even more of a turn-on. Spurred on by this, I began to withdraw my lips up the length of her cock before taking it all back in again, fucking my face with her hard cock as if my wet lips were the swollen pussy lips of some slut groupie, which is what I realised I was rapidly becoming through this evening of passion with a pop superstar. Meanwhile, as I sucked pleasurably on her cock, my hand that had previously been stroking her shaft was able to move down to massage her shaved balls, as if willing and encouraging her salty, warm juices to come flying from there down my throat.

From there, my wandering fingers moved on, straying further between her beautiful legs. A couple of years earlier, I'd had an ex-girlfriend, Carly, who had liked, when sucking my cock, to insert a finger up my arse. Carly had been a very kinky girl and I hadn't, at the time, felt entirely comfortable with some of the things she liked to do, and this was one of them. Right now, however, I could just sense that this would be the kind of thing that would get Britney off and, as for me, well, given how much my dick had liked being up inside her pert arse, I thought my finger would probably enjoy a go. So, still sucking on her warm, hard cock, I lifted her balls to allow my fingers access to her little arse-hole. I thrust my index finger deep inside her just as I took even more of the length of her cock down my throat. At this, Britney gave a delightful, girlish squeal of pleasure.

"Oh yes," she was screaming her pleasure louder now as she got ever closer to her climax, "Oh yes, yes! Oh fuck yes, that's it!"

I took my finger out of her arse and let her dick slip from between my lips, the pleasure my finger had given her arse had made me wonder what more kind of stimulation my tongue, growing in confidence, could give. The hand that I had been using up her arse, I now went back to wanking her off with, as I put my head deeper between her thighs and ran my tongue gently and tentatively around the rim of her puckered tight arse-hole. I could feel through my tongue a shiver of pleasure running through Britney's body at this as she gave another little scream. I inserted my exploratory tongue a little deeper into her arse, savouring her musky taste and smell as I began to thrust my eager, lapping tongue in and out of her warm arse-hole just like my cock had done not that much earlier. I could still taste some of my cum in her arse and that enticed me further. By now, Britney's screams and moans of pleasure were getting so frequent as to have her spend more time screaming out than silent. I knew she wasn't far away from her climax and, sure enough, as I plunged my tongue deep into her and vigorously stroked her cock, she cried out.

"I'm gonna cum, Rich! Oh god, I'M GONNA CUM!"

And cum she did, her cock exploding and shooting her sticky juices all over the place. As soon as I heard her scream this, I quickly tried to withdraw my head from between her thighs so I could catch her cum spewing forth into my mouth. I wasn't quick enough, however, and I found myself stroking her off as she shot a couple of spurts into my hair and across my face before I could get my lips around the head of her trembling dick. I continued to stroke her cock as her cum hit the back of my throat and I eagerly swallowed, savouring every taste I could have of her. However eagerly I swallowed her cum, I couldn't swallow it quick enough and soon my mouth was so full of it that there was no room in me for her cock to remain and I had to let it slip from my mouth, all the while with Britney still spurting across my lips, face and chest.

When her incredible orgasm had finally finished, I stood up, my face dripping with cum which I tried to catch in licking around my lips. Britney, seeming exhausted from the effort of spewing her juices into me, sat up a little. I knelt over her and kissed her on the lips, using my tongue to push her cum that was still in my mouth down her throat so she could taste the pleasure that her ejaculation had given me. Britney reached down my sticky chest and squeezed on my erect cock, standing proud from my body and crying out for relief.

"How selfish I've been," she said, pushing me back off her and lying back down on the bed, "Having you pleasure me with no relief for yourself," I'd enjoyed the experience of sucking her off and eating out her arse-hole almost as much as she had but never mind, she was offering me something more here and I wasn't going to turn it down, "How about you fuck my beautiful tits?"

Well, I don't need to tell you what I thought of this idea, so eagerly I sat myself astride her chest, with my erect cock nestling in her cleavage. Britney reached her hands and pushed together her perfect round, surgically enhanced breasts so my cock was as snug between them as it had been up her arse. Then, I proceeded to thrust three or four times between them, while Britney bent her head down and stuck out her tongue to brush across the head of my cock every time I thrust up closest to her mouth. These three or four thrusts were all it took, however, before the arousal that I'd already had from giving Britney oral relief combined with the current tit fucking sent me over the edge and I came bucketloads across Britney's tits and face.

A few minutes later we lay back on her massive bed, cradled in each other's arms, I had licked Britney's body clean of my juices once more and we had passionately French kissed to share them out between us. I felt a warm glow of happiness inside, I'd set out to do anything I could to please Britney and I'd done that very well if the force of her orgasm was anything to go by. But, at the same time, I'd discovered a fantastic new pleasure that I now regretted missing out on all those years of fucking just girls, the pleasure of a warm, stimulated cock thrusting down my throat.

"That was amazing," Britney said to me with a cum sticky smile, "Where on earth did you learn to do that?"

"I told you that was my first time," I said, "But I learn from the very best."

I kissed her again showing my appreciation of how her example had made me do so well when it came to my turn sucking her.

"Well, you're a natural," Britney said, "I bet you're now thinking you've really missed out on one of life's great pleasures up to now."

She practically read my mind. However, there were other thoughts going on in there, deeper, stranger thoughts. Seeing the pleasure both Britney and I got from cocksucking and how much she took pleasure in being a woman, my curiosity had been sparked off. Thoughts now ran through my mind that included a desire to know now how it was to be a woman like Britney, how it felt to dress and act and fuck like a woman, like her. I could barely admit the force of this desire to myself, I'd learnt a lot of new things about myself tonight but was I ready for this?

Britney looked deep into my eyes and seemed to read my thoughts once more, "And now you want to take it further, you're not content with sucking cock like a slutty girl, you want to know what it's like to be one." I couldn't lie to Britney, not now, not after everything we'd done to and with each other this evening so I had to admit to her that that was indeed the thought flooding my head right then. Britney flashed a white smile at this, "That's great," she said, "We can have a go right now at seeing how you'd look and feel if you were a woman."

To be continued... 



Oops, I Did It With Britney Pt. 04



6. I'm A Slave 4 U

We were both still a little sticky from the sweat and cum of our hot, passionate sex together, so Britney led me through to the massive en-suite bathroom that led through from her bedroom. The bathroom was decorated with the same height of expense and taste as the rest of Britney's suite and the huge shower was easily big enough to fit the two of us beneath it and I very much enjoyed the closeness of Britney's hot, naked body as the warm water ran over the two of us, cleansing and freshening us up again. In fact, the closeness of Britney's pert, sexy body would almost certainly have stirred up further arousal and erection in me were it not for two things. For one, I had already came over her three times this evening and that, to a certain extent, took a little bit out of my ability to become quite so easily excited again. The second reason was that my head was swimming with more nerves than I'd had when I'd first broken into Britney's hotel suite and hidden to try and see her naked.

So much had happened since then. I'd discovered that the world's most beautiful woman was not, in fact, all woman and now she had suggested to me that I might like to try to become a bit like her, to get a window on the world as it is seen and felt by a woman. That was what was causing my stomach to churn with conflicting feeling. On the one hand, I did find myself filled with a desire to have Britney transform me, even temporarily, into a woman, but on the other I felt ashamed to even be thinking about this let alone wanting it so much. The whole thing was more than a little embarrassing for me but I decided to place myself entirely in Britney's hands, she knew what she was doing when it came to this and I'd do anything for her. Still, there was a part of me that hoped Britney would just forget her suggestion, she hadn't mentioned it again as we had showered and I thought perhaps she would decide that it was too odd and not want to go through with it. Another part of me was dying to have her bring it up again and it probably won't surprise you to know that this was the part that was to be satisfied and excited.

"You won't be able to make a very convincing woman with all that body hair," Britney told me, "That'll have to go, I'm afraid."

Like all good hotels, we supplied all kinds of toiletries and things that guests might need or have forgotten, and, in the case of stars like Britney, lots of other free stuff as well. Anyway, in amongst these things, Britney had pulled out a woman's razor and now proceeded, while the shower was still running, to shave my body of all its hair. Now, I've never been a particularly hairy kind of guy but it still took a while for Britney to take off every hair on my body from the neck down. I won't bore you with the details of this process, suffice to say, a while later, as the warm shower washed away the last of my body hair down the drain, I felt like a new man, or rather part way to becoming a new woman. I was already becoming increasingly keen on this transformation. I was loving the smooth, slinky, feminine feel of my hairless body as I stepped out of the flowing water of the shower and Britney wrapped me in a thick, plush white towel.

"Now then," Britney said as we, both wearing just towels to cover our smooth dripping bodies, padded back into the bedroom, "We need to pick you out something to wear."

As you might expect from a star like her, Britney had brought quite a lot of luggage with her. There was a bag in the wardrobe beside where I had concealed myself earlier and the suitcase I had rifled through that had been on the bed and was now upturned on the floor having been swept away in a moment of passion between us. This suitcase, as I had already seen, contained most of Britney's casual, not especially sexy, day to day wear, T-shirts, sweatpants, that kind of thing. Out in the main living area of her suite, however, there were a couple of other large cases that I had not yet seen the contents of. It was to these that we now went, still wrapped in fluffy white towels.

"These are where I keep all my sexier outfits," Britney said to me, indicating these cases, "All the clothes that I wear if I need something quickly to go out to a bar or a club or if I have to make some public appearance or promotional stuff and I don't have a stylist, it helps to have all these sexy clothes."

Britney opened the nearest case and, sure enough, it was filled with all the clothes that I had hoped to find on opening the case on her bed, tight little mini-skirts and revealing tops. Britney began to throw some of the clothes from this case until the floor was covered with a collage of some of the sexiest clothing you have ever seen. Some of it I recognised from Britney's various public appearances, but some of it was stuff that I had never seen before.

"What would my sexy little girlfriend like to wear?" Britney asked smiling, as she opened a second case to reveal a great array of wigs, mostly blonde but some black and red, of different lengths and styles.

I looked over the clothes strewn across the floor, my eyes assaulted by all the styles and colours available to a woman, particularly one of wealth and fame like Britney. I was like a kid in a candy store, completely incapable of narrowing down all the feminine fashions I was drooling over to one single outfit choice. My eyes were finding themselves drawn more and more to a tiny little cream coloured suede mini-skirt that I seemed to recall Britney wearing on a TV show two or three years earlier along with matching boots and a sky-blue vest top. It was just the kind of the skirt that I loved to see women in, I loved to see there long legs exposed, I loved to think of what little it would take to lift up that skirt and see the joys beneath. However, even though I would have loved to see it on Britney, I balked a little at wearing something so tight, short and revealing myself. After all, I had never even thought about dressing as a woman until today, I didn't think that I was confident enough in my femininity to wear something like that. Instead, I picked up a pair of denim capri pants that, although tight and feminine in their cut, were at least closer to my normal attire than wearing a skirt.

Britney saw what I was holding up and shook her head with that naughty smile on her face once more. "Oh no," she said, "Wouldn't you much rather wear a little skirt. It's much more appropriate for your first girlie experience." She walked over to the pile of clothes and picked out the exact cream coloured mini that I had been after, "This is much more you, I think, you don't want to cover up those lovely, sexy legs. Any woman would die for those legs, and they'll send any man crazy in a skirt like this" she said, holding it out to me.

I couldn't deny that she was right, I decided to conquer my nerves and wear it, searching through the clothes pile until I found the sky-blue vest top that I remembered her wearing with the skirt on TV. The case with the wig contained all of Britney's shoes and I looked through them too until I could find what I was after, a pair of knee high suede boots in the same cream colour that matched the skirt.

Britney looked approvingly at the outfit that I had just picked out, "That'll look great on you honey," she said with a smile, "Now all you need to wear with it is some really sexy underwear. You never know when you're a hot girl like you just when some guy's gonna want to see under your skirt so you need to be prepared with the hottest panties. I think I've got just the thing for you."

As she was saying this, Britney hurried into the bedroom next door and emerged, a little later, now dressed, if you can call it dressed, in some very sexy lingerie, a white silk night-dress that was so thin that it left nothing to the imagination. The lines and curves of her body were perfectly visible beneath it, as was the curve of her pert breasts and her nipples. Beneath this thin material, all she wore was a matching pair of white panties in order to cover up the one part of her that wasn't a totally perfect example of femininity. In her hands, she was carrying, to my surprise and pleasure, the red lace panties of hers that I had been sniffing when first she saw me in her wardrobe, and a matching red lace bra. Those panties represented the start of this wonderful night with the pop princess and nothing would turn me on more right now than wearing them. After all, I had always wanted to get into Britney's panties, this wasn't necessarily the way that I had meant it, but it was certainly an exciting and arousing new development.

I slipped the red lace panties up my smooth, shaved legs until my cock and arse were encased in their sensual feeling delight. I'd never got this kind of feeling wearing guy's underwear, Britney's panties made me feel sexy and aroused, even just putting them on was provoking a little stirring in my groin. I didn't really know what to do with the bra; I'd had plenty of experience taking them off but not so much when it came to putting them on. Britney, however, helped me into it and filled out the cups with tissue from the bathroom, expanding my flat chest to impressive, round Britney breasts.

I wanted to look in the mirror to see how if I looked anything like as sexy as Britney's underwear was making me feel, but as I turned to do so Britney stopped me, telling me the surprise and pleasure would be much greater if I didn't admire myself until the transformation was complete. I agreed to this, but I couldn't help but look down at my smooth, sexy body in the red lace lingerie and see how feminine and sexy it looked. 

Next, I slipped the blue vest top over my head and then slid the tight suede skirt up my thighs. Fortunately, I'm not a tall guy and very slight of build, but still the couple of inches I had on Britney meant that the clothes, normally tight and revealing even on Britney, were even more so on me. I loved the feel that I got from wearing the tiny skirt, showing off my long sexy legs, my cock and arse in just red lace panties feeling excitingly exposed. 

My feet were probably not much bigger than Britney's, anyway I fitted into her cream coloured suede boots without too much effort on my part and they weren't tight or constricting. A problem came when I stood up after having put the boots on, I was unused to heels and even though these were not that high, only about three inches, as soon as I took a step, I could feel myself falling. I tripped forwards and for a moment felt a rush of panic that I would hit my head on the floor and that when the paramedics came they would find me dressed like this and all would be revealed. Fortunately, it never had to come to that as I found myself falling into the arms of my gorgeous lover.

As my stuffed red bra pressed against Britney's breasts, I looked up into her beautiful face. She smiled down at me and laughed at my misfortune,

"I think you might need to get a little practice in those heels," she said.

So, I spent the next few minutes simply pacing, or rather tottering, back and forth across the room. Initially I was pretty shaky but, with Britney's tuition, I soon got the hang of it, taking smaller steps, walking heel-toe, and swinging my hips in a sassy sensual way.

"You're almost there," said Britney, seeing how I could now walk, at least passably well, in the heeled boots, "With hair and make-up, you'll be the complete sexy girl." She looked through the various wigs that she had, searching for one that would suit my new feminine persona and outfit. "Here we are, this is perfect for you," picking out a platinum blonde coloured wig cut into a bob.

I sat in one of the comfortable leather chairs that the living area of the hotel suite provided as Britney put the wig on my head and adjusted it until it fell right into place as if it were my natural hair. Finally, Britney got out her vast make-up kit and made up my face to look much more womanly. Britney herself preferred dramatic eye make-up against the rest of her face being more natural, and that's exactly what she gave me. She matched the sky-blue colour of my vest-top with some funky blue eye shadow, which really picked out my eyes and their already naturally long and fluttery lashes, and a more natural pink lipgloss that shimmered and sparkled like the glittering mascara she had given me.

My transformation from skinny, rather ordinary English guy into hot girl was complete, now all I had to do was to check myself out and see how it looked. Again, I could feel butterflies in my stomach as I was filled with nerves, I could sense that any transformation could never meet my expectations but, at the same time, I was tingling with anticipation. Finally, Britney stepped aside and allowed me access to the mirror. I almost rubbed my eyes in disbelief at the sight, only I knew that it would smudge Britney's carefully applied eye make-up. There, standing in the mirror, was one of the hottest girls I had ever seen. I looked like her! Well, maybe not quite as stunning as Britney, but I looked like all those totally hot blonde American girls that followed Britney's looks and style. If I met this girl in a bar or something, I would definitely want to fuck her.

The suede boots and their three inch heels accentuated the length and curve of my sexy smooth legs, all the way up to my thighs were the tiny suede mini-skirt barely covered anything. Turning around and bending over, I could see my red lace panties sexily revealed beneath the skirt that barely covered my arse. My false breasts protruded forward from my body, stretching out my top across them and revealing my midriff and narrow waist, not quite as gorgeous as Britney's but still looking pretty good. Britney had worked her magic best of all on my face, and I moved in extremely close to the mirror to examine it, looking for flaws that might give away that my perfect feminine complexion wasn't quite what it seemed but could find none. Along with the very tight revealing clothes, the platinum blonde wig and sparkling eye make-up made me look like a cheap slut but I wasn't complaining, the slutty look had worked for Britney in her videos and it was really turning me on now. Thanks to Britney's dramatic eye shadow, I was drawn to my eyes like never before, and fluttered my eyelashes and pouted my lips at my reflection. Christ, this was hot, I didn't even need anyone else there to turn me on. I couldn't help myself as I leant into the mirror and gave my reflection a quick kiss, leaving a smudge of pink lipgloss on the shiny reflective surface.

As I struck some flirty, revealing, girlie poses in front of the mirror, enjoying my new femininity as much as I could, I hadn't noticed that Britney was no longer beside me, so absorbed was I in what I had become. In fact, the first I noticed of Britney's disappearance was when I heard her voice behind me as I posed again, imagining I was a superstar like Britney and the mirror was a camera giving me a sexy photoshoot, only now she wasn't alone.

"Still admiring yourself, she's always doing that," came the sound of Britney's voice that caused me to spin around in shock and embarrassment, barely able to keep upright in the heels.

I didn't know what to do, standing beside Britney was a very big, muscular black guy that I recognised from earlier as her security guard. I doubt if her recognised me, I looked quite different now from when I had seen him earlier on, but I was struck by fear that he might at least see the real me beneath the disguise. I suddenly realised that I had let Britney dress me up like this without keeping track of anything else that was going on, I had no idea where my clothes were and now I was struck by an even greater fear that Britney had finally decided to throw out her intruder and all this dressing me up was just to humiliate me on the street.

I shouldn't really have worried so much about that; Britney was having too much fun with me to want to throw me out. Instead, she decided to introduce us.

"This is Jake, my security guard," Britney said, "And Jake, this is my friend Rachel." Rachel, is that what my name is now? I tried it round a few times in my head. Rachel, I liked it, it sounded good, it sounded sexy, it sounded me. I was beginning to think I might rather like being Rachel and some of my nerves abated a little but I was still worried about why Britney had brought her security in. "Rachel, naughty little girl that she is, sneaked into my hotel room to surprise me. Well, it's always nice to see you Rachel," she continued, coming over to me and caressing my false breasts as if to show how really nice it was, "But maybe this wasn't quite the way to do it."

"I thought I heard some screams," said Jake the security guard, speaking for the first time, "That must have been it," I blushed red with the knowledge of what those screams had really been, looking in the mirror I could see that maybe I should blush more often, it looked good on me, or at least on Rachel.

"Well, you can trust a kinky little friend like Rachel to turn up with her voracious sexual appetite unsatisfied," Britney went on, if I'd been embarrassed before at just being seen like this by a guy, and such a strong and imposing one too, now I was mortified to hear Britney discuss my sexual desires with him. "I'm afraid there's nothing I can do to totally satisfy her. You see, Rachel likes to be made to feel totally feminine, to be fucked just like a woman, and I can't do that for her. She just loves cock, so I thought you could help her out a little."

"I can see that we're going to get along just great," Jake grinned in a dirty manner that didn't make me feel any safer or more confident. 

He didn't seem particularly surprised at Britney introducing him to a friend's sexual desires like this and I began to think that maybe this wasn't the first friend Britney had introduced to him. After all, I knew that with all their touring and moving around, celebrities were often pretty close to their security people. Not that that made me feel any better.

"Britney, can I talk to you alone for a moment," I said, talking as Rachel for the first time. 

I hadn't really thought about how I would speak as Rachel, but without my intending it, this sexy purring American accent just came out. Now, I'd never been particularly good with accents, but this just seemed right, it seemed to fit the person that Rachel appeared to be. As I said those words, Britney gave me a little grin at my choice of accent before taking me by the arm into the next room, while Jake patiently waited.

"What's wrong Rachel," Britney said, as soon as we were alone in the room, "You wanted me to help you feel what it's like to be a woman, being with a guy is a pretty important part of that."

"Yeah, but..." I said, still talking in Rachel's cute American accent, I didn't really know what to respond, "I just...I don't know about this."

"Look, you know you love the feel of sucking on a hard cock, and Jake's is particularly good, or so the other girls have told me," Britney said, her hand placed on my arm reassuringly, "That's all you have to do, trust me, you'll love it. And did you see the way he looked at you, you're really hot, he wants you so bad, don't you think it would be cruel not to let him."

I sashayed back out of the bedroom in my skirt and heels with a new-found confidence and walked over to Jake, stopping in front of him and just standing there for a few moments, not really sure of what to do now. I'd never thought about, never wanted sex with guys ever before, hell until not much earlier this evening these thoughts of sucking a girl's cock or what it would feel like to be a woman would have disgusted my mind. But now Britney had turned me on to so many new things, I didn't know what to think. Part of me didn't want to go here at all, but, as Britney had reminded me, I had wanted to know the feel of being a woman, and the Rachel part of me was kind of excited at doing more new things. I must have been standing still like this for a while because Britney intervened, seeing that I wasn't going to take the initiative.




Oops, I Did It With Britney Pt. 04



"She might seem shy now, but soon you'll see she's a sexual animal," said Britney to Jake, "Maybe you should get things started, kiss her."

Well, I was about to lose any choice or control that I had in the situation, if there was any time to pull out and leave, to decide that I wasn't going to go through with this experiencing things like a woman thing, then now was it. That I didn't pull away, I just stood there waiting, probably says something about the way that maybe my confused thoughts and desires were turning.

Jake took a step towards me, he must have been over 6'5" and he towered above me even in my heels. He encircled my shoulders in his muscular arms, there was no way I was escaping that grip even if I wanted to, and pulled my face towards his, leaning down towards me at the same time. Initially a little reluctant, I tried to pull against his embrace and closed my lips as he pressed his lips against them, but I was powerless to stop his desires and those that were springing up from inside my body.

Jake pressed my body against his, my little, curvy frame and soft fake breasts pressed against his hard muscular chest. Maybe it was being Rachel giving me new desires and feelings, but I was beginning to enjoy the experience of being totally in another man's power. As I let myself give in to him, as I opened my lips and began to kiss him properly, sensually, I felt a stirring in my groin where the shock of first seeing Jake had destroyed the arousal of my first sight of Rachel. Kissing a guy was certainly different to kissing a girl, I was used to taking some initiative but here I just fell into his arms and allowed his tongue to invade my mouth. He smelled musky and masculine, not at all like he soft perfume of Britney's that I was wearing. My fluttering eyes were closed, I'd told myself this was because I wasn't into kissing a guy and so I didn't want to see him, but I now realised it was because I was totally getting into it. Where one of his hands held the back of my head by my blonde wigged hair, the other was around my narrow waist, pushing my hips against his. Even through my suede skirt and his jeans, I could feel as I pressed against him his cock becoming hard beneath, just like mine.

Breaking away from the kiss, Jake's hand that encircled my waist now pulled at my vest top. I raised my arms, allowing him to pull the top over my head to reveal my stuffed crimson bra. My stomach fluttered with a moment's worry at discovery if he dislodged my wig but I was fine, Britney had fixed it well in place. Having removed my top, Jake did the same to himself, stripping out of his tight black T-shirt to reveal the dark, taught, toned muscular chest beneath. He grabbed me by the hair again and pushed my face into his chest. His masculine scent was now overpoweringly alluring as, almost unwillingly as if Rachel had a separate mind to mine, I found myself kissing and licking his hard chest. I didn't even realise that I was progressing down his chest towards his jeans and what lay beneath, I didn't realise how keen I was becoming to suck a real man's cock, to feel like a real woman.

Jake reached to unclasp my bra as I moved down towards his cock. He was on the verge of revealing how my chest wasn't quite as impressive as it seemed, but Britney was fortunately there to help me out whenever anything went wrong. She placed her hand on Jake's and guided it away from my bra strap towards his own jeans, getting him instead to unbutton them. He did so and, as Britney pulled his jeans down around his ankles, Jake grabbed my shoulders and pushed me to my knees so when that when his semi-erect cock was released, it was right in my face.

It was massive, even not fully erect it was eight inches long and very thick and it was only going to get bigger. The only cock I had ever eaten before was Britney's and that was only just over half the size of this one. My eyes widened and I wondered what the hell I was going to do with it.

"So big..." came the sound of Rachel's American accent from my mouth, Jake smiled with pride and lust at this comment.

"Poor little Rachel," Britney said, as she knelt down beside me, "She's never taken such a big black cock before. Don't worry Rachel, I'll help you out."

Britney pulled me into a passionate kiss, both of us kneeling before this ever stiffening cock of her security guard. She took my hand in hers and guided it to Jake's cock, I could feel it hard and throbbing, it was so thick that my hand could hardly reach all the way around it. Guided by Britney's hand, I began to jerk Jake's cock off, much as I had hers earlier, and, as we broke from kissing, she used her other hand to push my head towards his cock. Britney's head was right beside mine and, as she stuck out her tongue and ran it around the dark head of Jake's black cock, so did I. Soon, both Britney and me were kissing and licking all up and around Jake's cock which was now totally firm and erect. Clearly from the expression on his face, he was totally aroused at the sight of two such gorgeous blonde girls paying such attention to his massive member.

Thanks to Britney's assistance, I was growing in confidence and desire when it came to giving Jake head. As soon as I'd built up enough confidence, I moved my lips round to the head of his cock and tasted his pre-cum. Using his cock, I painted my lips with this glistening juice to make them glitter even more, before opening them up and taking the first inch or so of his cock into my mouth.

Seeing that I was now getting into it, Britney moved away and sat back to watch, leaving me to it. I took as much of Jake into me as I could, massaging his cock with my tongue in the hope of drawing it further inside me. Fortunately, my earlier experience with Britney's cock stood me in good stead here and I was much more able to take a much longer length in here. Gagging the first time, I overcame my gag reflex and opened my throat until I was deep throating almost the whole length of his monster black cock.

But if I thought that I was going to be taking control to pleasure him, as I had with Britney, then I was sorely mistaken. No sooner was I flush with pride at how much of Jake's cock I could fit in my mouth, than he was withdrawing it. I didn't want this and tried to bring my mouth up to meet his cock. Jake was having none of this and firmly took control himself. Pulling at my blonde bob, he began to thrust his cock in and out of my mouth. All I could do was kneel there, open up my throat, and enjoy the face fucking for all it was worth.

So this is what it feels like to be a horny little slut having her mouth violated by a hung stud, I thought, this is amazing, I was really, really turned on by Jake's utter dominance and control as I just let him take over, my cock was getting fairly hard in my red lace panties by now. I began to moan with pleasure as his cock filled my throat and then withdrew.

"You weren't kidding Britney," said Jake, grunting and groaning, "This little bitch sure is hungry for cock." 

And he was right, there was nothing that I wanted more in the world right then than to swallow his black beast and have him shoot his load down the back of my throat. However, Jake and Britney weren't quite done with me yet.

"Don't just fuck her face Jake," Britney said, "Rachel needs more than that from a stud like you."

Oh God, I thought, I know what's coming now and I'm not all liking the thought of it. Sure enough, Jake eagerly withdrew his cock from his mouth, excited by the prospect of fucking this sexy blonde cum-slut. And he was about to get even more excited by what Britney said next.

"Rachel's on her period so you can't fuck her pussy," thank God for that, Britney came up with the perfect excuse that was sure to turn him off, "But I'm sure she'd love you to take her in the arse." Just as I'd feared, given how much Britney loved this and given my desire to be used like a woman, I kind of really wanted this, but how Jake's massive black cock would ever fit into my tight white arse was something of a major worry. "Now Rachel's a virgin back there, so go easy on her at first," Britney concluded, getting Jake ever more excited.

I remained on my hands and knees, more glued in the same position through nerves than eager to have this happen. Jake moved behind me where my arse now stuck in the air, my suede skirt riding up to reveal sexy scarlet panties. Britney knelt in front of me and kissed me on the lips.

"Trust me," she whispered in my ears, "You're going to love this. Just try to relax as much as possible."

My sucking on Jake's cock had made it pretty wet and lubricated but this clearly wasn't enough to fit him inside me. Jake pulled my skirt further up around my waist and pushed my panties aside to reveal my small arse hole. He licked a finger and shoved it up my arse, my body trembled as I clenched down on it, trying to remember to relax. Jake fingered my arse with first one, then two wet fingers, trying to get it ready to receive his monster cock. I was feeling totally aroused by the feeling of these two fingers as they stimulated me, pushing up inside me and when he removed them, my arse felt empty and desperate for more.

Never fear, I was soon going to get it as filled as I could ever handle. I felt Jake's hands on my waist and the head of his cock brushing against the entrance to my arse, my body was tingling and shivering even at this slightest touch. I closed my eyes and prayed this wouldn't hurt too much, now I know what must have been going through all those girls' minds when I wanted to arse fuck them, except I really wanted this, despite the pain I yearned to feel Jake inside me, feel it like only a woman could.

I tried to relax as much as I could, but it really wasn't good enough to prevent the searing pain as he thrust his thick cock up inside me. I felt tears welling up in my eyes and let out a girlish yelp of pain but Jake, taking this for the delight of a sluttish girl like Rachel, was only encouraged by this and thrust further and deeper inside me.

"Fuck Rachel, you really are tight," he said as he pushed deeper in before slowly withdrawing and pushing his cock back inside me.

For a while I couldn't help but feel the intense pain of it as tears ran down my cheeks and I bit down on my lip to try and stop myself crying out any more. Jake held my waist with a firm grasp that told me I wasn't going anywhere as he had his way with my arse. I looked up and looked around for Britney and was shocked to see her standing holding the camera I had brought with me to the hotel suite so long ago to try and snap pictures of her naked. As Jake thrust painfully in and out of my arse, Britney snapped away taking photos. I knew I'd never be able to get these developed, what would they think at the photo shop to see me dressed as a woman being fucked up the arse.

"Now we're even Rachel for your videocamera stunt," she said, snapping away as I realised that she was getting back at me for tricking her into an arse fucking earlier on.

Still, I was starting not to care about that as my arse became stretched and numb and generally more used to being filled by Jake's cock. I was beginning to enjoy his slow, rhythmical riding, once more my own cock was becoming hard and straining against my lace panties. I knew what Britney's photos would show as I could see it in the mirror in front of me and it was turning me on even more. What I saw was the sight of a massive black cock violating the tight virgin arse of a thin, sexy white blonde girl, this was the kind of thing I'd have paid good money to see on the Internet and here I was seeing it for free, hell I was having it done to me for free.

As the stimulation of Jake's cock against my prostate began to heighten, I began to let out cries and moans not of pain but of joy at this, just the latest in a long line of arousing new experiences I had had that night. I could no longer be satisfied with Jake's slow, gentle action, I wanted more.

"Come on Jake, fuck me," I began to cry, still using Rachel's American accent despite my heightened sense of arousal, it just seemed right for the hot porn movie sex I was engaging in, "Use me like your little whore, fuck me, fuck me harder you stud, I wanna feel you cumming deep inside me."

I could see Britney smile at me as she saw how much I was enjoying this, the final step on my experiences of what it could be to be a woman. Jake didn't need much encouragement to speed up and soon he was thrusting with ever increasing vigour. My little white virgin arse was impaled on his monster black cock and still I was screaming out for more, screaming for him to fuck me harder.

I could tell that Jake was loving using my arse almost as much as I was loving him doing it to me. It didn't take long of Jake's more violent and vigorous fucking for the stimulation of my tight arse to be too much on his thick cock. I could feel his cock growing with his cum shooting up from inside him as he cried out with one final hard thrust and filled my arse with cum, shafting me three or four more times while his sticky juices filled my arse and began to ran down my legs.

Finally, Jake was able to pull his limp cock out of my sticky arse hole. I remained on all fours, knowing that if I got up then Jake would see the huge tent in my skirt caused by my aroused cock straining against it. So I stayed still as Jake pulled his clothes back on. He looked down at me as I scooped up some of his cum that was running down my legs and licked it from my fingers and smiled, "Britney was right," he said, "You sure are one hot cum hungry slut." And with that he left.

With Jake gone, I picked myself up and put my top back on, I don't know why, I guess that after having my cherry popped I felt more like a woman, more like Rachel than ever, and I wanted to remain in her clothes as much as possible. Britney led me back through to the bedroom and dropped herself onto the bed.

"So, how do you like being a woman, Rachel?" she asked.

"It was great," I said, "I never knew how fucking amazing it would feel to be fucked by a girl, I'm so turned on right now."

"I can see that," Britney smiled, indicating the tent in my cum stained suede skirt, "So am I, I can't tell you how arousing it was to watch you. You should be a porn star, Rachel."

With this revealing of her own arousal, she pulled up her silk night-dress and slipped her white panties down around her ankles to reveal a cock as hard and erect as mine.

"Come on over," she said, beckoning me with that come hither smirk that we've seen in her videos, "Come here and use those talented, cum hungry lips on me."

Britney sat up and opened her legs, I got up on the bed too and lay down, my face between her thighs. Opening my mouth, I took all of Britney's cock inside without great difficulty after the size of Jake's and began to use my tongue and lips in a way that I had learnt quickly throughout the evening. As I quickly brought the gorgeous pop superstar to a screaming climax, I found myself dry humping the bed where I lay through my skirt and panties. So, given how stimulated I still was from Jake's vigorous arse fucking, as soon as Britney shot her juices against the back of my throat, I too had my final orgasm of the evening, creaming into my, or rather Britney's, panties until they were now completely cum soaked on both sides while my mouth filled up with Britney's juices.

I was exhausted, no surprise given how late it was and how much hot sex I'd had that evening, how many fantasies had come true and how much in my life had changed. I lay beside Britney and kissed her lips, using my tongue to push her cum into her mouth so we shared a cummy kiss before each swallowing part of it. I lay back on the bed with Britney in my arms, satisfied in my feminine form in a way that I never had been before.

7. Baby One More Time

The next thing that I knew, it was some hours later and I was waking up in a massive king sized bed that certainly wasn't my own. My arse felt sore and my head was spinning, it took me a few minutes to remember where I was. As I sat up on the bed and my eyes re-accustomed themselves to seeing in their awake state, I looked down beside me on the bed and there, stretched out before me, was the world's most beautiful woman, peacefully sleeping. She was still dressed in her little white silk night-dress through which I could see her nipples, her long legs were bare all the way up to where I knew her little extra something was hidden by her little white panties. Her perfect round breasts rose and fell gently with her breathing. As I looked down at her beautiful sleeping form, all the events of the previous night came flooding back to my mind, how I had discovered Britney's little secret, how my fantasies had all come true as I fucked her arse, how she had helped me see what it might be like to be a woman like her and how my virgin arse had been deflowered by her well hung security guard. I smiled to myself at the happy remembrance of the radical new pleasures of the night before.

Looking at my watch, I saw that it was already 4 AM and I needed to hurry home, as I knew I couldn't be discovered here in Britney's bed, certainly not dressed like this. I was still wearing my feminine clothes from the night before, although they had become further dishevelled from my sleeping in them. I sat on the edge of the bed and took off the suede boots before standing up in my bare feet and unzipping the cream coloured skirt, letting that fall to the bedroom floor as well. I slipped the tight top over my head, dislodging further the blonde bobbed wig that had slipped a little from my head as I had slept on it. Looking down at the pillow, I saw my make-up smudged across it and, looking into the wardrobe mirror, I could see it smudged across my face. I was now dressed once more in just the stuffed red lace bra and panties. Looking at my reflection again, I couldn't help but once more feel a swell of pride at what a gorgeous woman I made. I straightened the wig on my head so the illusion of my sexy womanhood was more complete. It was going to be regretful to strip from this, to bid farewell to this side of myself, the Rachel side of me, and return to being simply plain old Rich. I blew my reflection a little kiss and then turned my back on it to face back towards the bed and the beautiful sleeping beauty that I would soon be turning my back on as well.

I walked over to Britney's side of the bed and looked down at her, she looked so peacefully happy in her sleep that I didn't want to wake her before I left. I bent over her to brush a little goodbye kiss against her soft lips before turning away and reaching back to unclasp my bra. I was just about to do this when I heard a quiet, sweet voice behind me.

"Rachel," I heard Britney say, "You weren't going to leave without saying goodbye," I turned back to see her sitting up on the bed, woken up, like the original sleeping beauty, by my gentle kiss. She frowned playfully at me and gave me a pouty look, "Give me one last goodbye fuck before you leave Rich, something to remember you by."

Well, how could I say no to that? Even if I had the chance to spend every night from now until the rest of time fucking Britney's pert arse, I would never tire of it, never be able to resist if I saw that sparkling desire in her eyes. So, given that I had just the one night with the most desirable woman imaginable, I couldn't leave without such a way of saying goodbye.

Britney had now stood up off the bed and pulled me into a kiss with one hand on the back of my blonde wigged hair. With the other hand, she stroked down my back to my red lace panties, all the time while still pressing our lips together and entering my mouth with her tongue. She slipped her hand inside the back of my panties and felt with her fingers towards my slightly sore arse hole. My cock, which had been soft after my few hours of sleep, now began to spring to attention as Britney thrust two fingers into my arse. My hands had been wrapped around her shoulders as we kissed, but now I reached down beneath her white silk night-dress and pulled her cock out from the white panties beneath. Her cock, like mine, was beginning to become excited once more as our bodies pressed together, my stuffed bra pressing against the very real, perfect breasts beneath the thin silk of her night-dress.




Oops, I Did It With Britney Pt. 04



As I grabbed her cock and began to stroke it off a little, Britney broke us from the kiss and pushed me back down onto her bed. I lay back, my cock sticking proudly upwards from my red lace panties, which had been pushed aside to let stand out. Britney got up onto the bed and sat astride my chest, facing away from me. She first began to stroke my cock with her hands, but soon bent further over to get her lips around it. As she began to suck my cock in the sensual way that only she could, Britney's arse stuck out in my face invitingly. What could I do but reach my hands up to pull her night-dress to around her waist? I didn't really have a choice about pulling her white panties aside to reveal her tight little arse hole. You can't exactly blame me for opening up her arse cheeks with my hand and sticking my tongue up inside her. I felt a shudder that ran right through Britney's body, from her arse where I was stimulating her, right through to her tongue, which ran over the head of my cock. After a couple of thrusts into her arse with my tongue, I diverted my attention to Britney's cock, slipping her panties down to her knees and putting my lips around the ever swelling head of her hard member.

We remained like this, sucking each other's cocks in the 69 position for only a few minutes. I could already feel my cock becoming more and more eager to shoot my load into Britney's mouth, but she wasn't content with that. She got up from sitting on my face and turned around so now she was facing me.

"I want you up inside me one last time," she smiled and licked her lips.

I smiled too, even despite our night of passion there was a still a thrill of pleasure at the highly unusual sight of the world's most gorgeous superstar as she opened her legs and sat astride me, positioning her arse hole at the tip of my cock before slowly sliding down onto it, her face entranced with an intense moan of pleasure. This was to be the last time that Britney Spears rode my cock, and she was riding it for all she was worth, throwing back her head and moaning and screaming wildly as she rocked vigorously on my throbbing dick. Meanwhile, she slid the straps of her night-dress down her arms so her pert, round breasts were now freed from that thin silk covering. As she bucked around on my dick, I reached my hands up to get one last caress of her sweet breasts, tweaking her nipples in a way that made her squeal and giggle with joy. Britney, meanwhile, took her own hands and began to wank off her own hard dick, stroking it in time the rhythm of her riding me.

Disappointingly, I tried to last as long as possible, but that's a hard thing to achieve with a super sexy shemale pop star writhing on your cock while stroking her own right in front of you, and how ever long they last, experiences like this, those that you wish would go on for ever, never last as long as they should. Britney began to breath more and more heavily and I knew that her orgasm was upon her as she rode my cock faster and faster before the stimulation of me inside her tight arse hole was too much for her and she threw her head back, tightened her thighs around me, and began to spurt her white juices over my chest. As she came, Britney continued to sit on my cock, rocking her body back and forth as she jerked herself off, her spunk shooting up my chest, covering my red lace bra with sticky white cum. As her cum finally shot up onto my face and into my mouth and, for the last time, I tasted her on my lips, my cock too exploded and filled up her arse with all the creamy juices I had inside me, a little something for the world's most famous singer to remember me by.

Having emptied my seed deep into my dream girl for one last time, I now stripped from my crimson bra and panties, leaving them on the bed as I wandered into Britney's bathroom to clean up. I took of the blonde wig and cleaned the smudged make-up from where it remained on my face, each moment making myself less and less Rachel and more and more Rich. Coming back into the bedroom, I found where I had discarded my ordinary, masculine clothes the night before and, regretful at all I was now leaving behind, put them back on, now totally transformed into the man I had been this time the day before, before all the wonderful things of this night, when fucking Britney Spears was just a wild fantasy of mine.

I was walking out of the bedroom, back to my own life, and I turned back to say one final goodbye to my adored superstar lover of the previous night. That stunning blonde scantily dressed creature came over to me, holding out the dark red panties that I had worn before, the panties of hers that I had been holding to my nose when she first discovered me spying from her wardrobe. How much had changed between us since then. Then I was a slightly scary, creepy intruder, but now I had become her passionate girlie lover. The panties that I had once sniffed and then worn as I was femininely deflowered represented how much I'd changed that night and how much Britney had experienced with me.

"Keep these," she said, pressing the lacy panties, both stiff with my cum and soft, into my hands, "Keep them as a memento of me...and Rachel."

I smiled gratefully at her, this was the last time that I would ever be this close to the world's sexiest star.

"I'll never forget this as long as I live," I said, pressing my lips to hers, tasting her taste for one last time.

"Neither will I," were her last words to me as I turned my back and walked out of her hotel suite and out of her life.

It was just becoming light as I crept down the stairs of the hotel and, stopping off only to return the hotel keys that I had stolen from Lydia, the chambermaid, out onto the street. There were a few people out and about but nobody recognised me or even looked very hard at me, quite fortunately I thought, as I hurried back home to my apartment to get a few hours sleep before I would have to go back to the hotel later in the day. I was working the afternoon-evening shift and Britney and her people had already checked out and headed off for the next date of the tour when I got in. My colleagues, naturally, noticed the glow of happiness that I was radiating but were convinced that this stemmed purely from the pleasure of seeing Britney in concert. Nobody even slightly suspected the truth of the matter and, quite frankly, why would they? It was so ridiculously unusual that even I had to reassure myself that it had really happened to me.

A month or so later and my year in America was up and I returned to England to settle into a somewhat more mundane life. I got a reasonable paying office job which I still work and met a new girlfriend, Shelley, who I moved in with after three months. Not long after returning to England, I, along with the rest of the world, read in fascination about Britney's marriage to Kevin Federline, and just as I write this I've recently heard that she's pregnant, I wonder how she'll manage to pull that one off! At first I felt a natural pang of jealousy against the man I perceived Britney had chosen over me, I even hoped that the rumours of their marriage problems were true, but after a while I came to except that a relationship between Britney and me would never have worked out, after all she was the world's greatest pop star and I was a nobody, still am actually. So, I wish her every happiness and success in her marriage and, if it doesn't work out, she knows where to find me. Well, actually she doesn't but I'm sure she could find out.

As you may have guessed, I never heard from Britney again. Shelley doesn't really understand my continued obsession with Britney, she prefers old-fashioned soul and r 'n' b music, and, at her request, the gold hot-pants poster is gone. But I still listen to her albums; they offer me a constant reminder of that wonderful night we spent together. Shelley tolerates this, she realises Britney is a part of me, although she doesn't know just how much of a part. She doesn't know the truth; I don't know how she would react to it so she doesn't need to know. My sex life with Shelley is regular and fairly enjoyable, I can't really complain. Since my night of passion in San Diego, I have never again had the chance to enjoy the pleasures of sucking a firm hard cock or having one thrust deep between my arse cheeks. I like to lap up my cum from Shelley's pussy after sex which she thinks is a little odd, so I can't imagine what she'd think if she knew all my thoughts and fantasies.

As for Rachel, well she does manage to make the occasional appearance. On the nights when Shelley is away from home, anybody looking into my house would see a gorgeous woman who looks just a little bit like me, dressed in one of Shelley's tight mini-skirts with one of her bras stuffed to fill out like breasts. They would see this Rachel load up a store of pictures on her computer of shemales and Britney Spears downloaded from the Internet. They would see her pull up the mini-skirt to reveal a bulging erection inside a very sexy, very special pair of crimson lace panties that may once have belonged to the world's biggest pop star. They would see Rachel stroke her cock through the red panties until she creamed inside them. Then she would take them off and lick the panties clean of her creamy juices and you might see a grin spread across her lips, painted with Shelley's lipstick, and a glow of inner happiness not seen in sex with Shelley.

These stolen moments are the moments when I feel closest to the memories of my wonderful night with a sexy superstar. It was in the trawl through Internet porn sites for some of these pictures to get me off that I came across literotica. I read, and was very turned on by, all the fictional fantasies of Britney sex and suddenly I had an idea. I had to keep Britney's secret to myself, I could never tell anybody and this was killing me. But I could get the story out of my head here. Most people will just dismiss it as erotic fan fiction, never knowing the truth, so Britney's secret is safe. Even if people suspect the truth, if you've read this far in the story you're probably pretty open-minded and so I ask you to keep the sexy secret with me. People may think it's all fiction but for me, reading over my account will always remind me that just for once, for a few hours, all my fantasies of sex with an iconic beauty were fulfilled and well surpassed and that's a memory I will treasure forever even if I never here anything of the name Britney Spears again.

THE END

Thank you.



Oops, I Did It With Britney



"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.

To be continued...