Britney Story

"That was delicious, how would you like to try some?"

Put like that, and coming from that gorgeous face, how could I refuse? Seeming to take my acceptance as given, Britney ran the same finger across her own hot glistening body, scooping up another load of our mixed cum. She held the finger out to me and I bent my head towards her and began to lick her finger clean, at first just lightly licking, before taking her whole finger in my mouth. I was beginning to understand why Britney enjoyed this so much, every time I tasted cum, it seemed to taste better and better and I savoured it more and more. Was I turning into a sissy? Well, one look at the gorgeous, desirable, if surprisingly well hung, woman lying beside me would confirm me in my masculinity. However, it had been going through my mind that Britney must have once been entirely a man, how and why had the transformation into the hot, and frankly very femininely so, woman that the whole male world lusted over happened? I decided the only thing to do was to ask her.

"Britney, can I ask you something personal?" I said, turning to her as we lay naked together on her bed.

"Sure, Rich, go ahead," she smiled, now the friendly, charming, Southern girl we all knew from her TV interviews, miles away from the hot, horny shemale I had just fucked.

"How did you become, you know, the way you are?

Britney smiled again, this time slightly wearily.

"It's a long and quite personal story," she said, "But since you're the best fuck I've ever had, I'll treat you to it."

And she did, telling me all about how she went from being a small, confused young boy in Louisiana, all the through to being Britney Spears, international superstar and sex symbol.

4. Boys

"As a child I only ever had two ambitions," Britney said, beginning her story, "One was to be a successful singer and the other, to be a beautiful girl. Now, for most traditional southern families, to come out with a wish like that would have been met with anger and disbelief. After all, all the families that lived around me wanted to raise red blooded American sporty men and so to have your four year-old son wanting to be your daughter would not be tolerated. At best I could probably have hoped for my desire to dress and act and become like a girl to be treated as a childish phase for my parents not to take seriously. But it was different for me, thankfully in this, as in so many other things in my life, I had the total support of my mum who did everything in her power to make things easy on me as a confused little boy wanting to be a little girl. I know now how hard this must have been for her, but she cared so much about me that all she wanted was for me to be happy. 'I always wanted a daughter anyway,' she would say, this was, you must remember, before the birth of my baby sister. So it was that, thanks to my mum's tireless efforts, I started at school with a wholly new identity, little Britney Spears, the cute all-American girl. I don't know what strings my mum pulled, but she made sure that all my teachers and, particularly, my classmates never knew that I was anything other than I seemed, a nice little girl. Because of this, it wasn't difficult for me to adapt easily to the life I had now chosen for myself, the life of a girl. After all, if everybody treated me as one and I felt like one then I could easily ignore the evidence of my body.

"With my ambition to be a singer, my mum was equally supportive and helpful. As soon as I was old enough to belt out classic songs, she entered me into all kinds of talent contests, most of which I won. As you probably know, the result of all this desire and ambition was to get me into the Mickey Mouse Club. The years that I spent doing that were possibly the best years of my life so far. I was able to fulfil my dream and be a singer and performer, and do it all on TV, and I was with lots of other kids who shared at least half of my dreams and desires. Nobody ever wondered if I was ever anything but what I seemed and so I never worried about fitting in. At school, I felt a little excluded more because of my precocious talent and ambition than because I was a boy masquerading as a girl. So, in the Mickey Mouse Club, surrounded by kids just as talented, I felt like I was among my own sort of people.

"I was devastated when it all ended with the Mickey Mouse Club, not just because I had achieved my dream of being a singer only to have it snatched away from me, but also because this marked the end of a time in my life when I was totally comfortable in myself, probably the only time that was true. As the show ended, I was entering adolescence and with it came the realisation that I wasn't really like the other girls who began to fill out with curves while I remained skinny and flat chested. I'd been taking female hormones to make me more feminine and anyway I still made a very pretty girl, one of the most desired by my high school's boys, but I didn't have the round breasts that I saw on other girls and this made me constantly aware of my difference. Not that I let this insecurity show, on the outside I was still one of the most popular, prettiest girls around. I wanted desperately to have surgery to make me more of a young woman but here my mum couldn't help me, my family were kind of poor and we didn't have anything like the money needed to pay for surgery.

"Then, out of the blue, came the answer to all my prayers. Ever since the end of the Mickey Mouse Club, I had been trying to get myself a record contract to carry on my dream of singing, either as part of a girl group or on my own, and now I had an offer. From there on, everything was a crazy whirlwind of activity as I got on planes and flew to New York to record my debut single and, hopefully, to become the singing star I always dreamed of being. The song was a brilliantly written piece of danceable pop called Hit Me Baby One More Time. I loved it even then, I began to sense that this could be it, this could be the answer to both my ambitions. Of course, you know what a huge hit the song was all around the world. A massive hit boosted by the sexy video. I came up with the schoolgirl video idea myself. At the time, I was growing accustomed to the further uncomfortable confusion of my growing sex drive, as a girl I thought I should be attracted to hunky men but it turns out I was finding myself attracted to almost everyone. But I knew that I couldn't give in to my sexual urges, not without revealing too much of myself. So, I wanted to do a really sexy video, kind of a fantasy, with me as a sexy schoolgirl. After all, if I still was all man in my body, I could at least flaunt myself as a girl, that would make me more confident in my femininity and would release some of those pent up sexual urges. Because I was still, in essence, a man, I had no breasts to show off so you can see how the schoolgirl outfit doesn't really show any of that, it's more concerned with showing off my bare midriff which has always looked this good."

At this point in Britney's story, I couldn't help but think back to all those days I had spent watching this sexy schoolgirl video and lusting and fantasising over the singer, all that time I had been desiring a man.

"So was this desire not to reveal the secrets of the real you the reason why you didn't want to give up your virginity for so long?" I asked her.

"I didn't want to keep my virginity for so long," Britney continued, "But I did feel it was necessary to do so. If I had given in to all my urges and desires and just had sex with the first person I felt attracted to, then I was sure that person would go straight to the press and sell their story and then my secret would be aired across the world. So I felt I had to wait, wait for someone that I felt loved and wanted me enough to want to fuck me no matter what was beneath my skirt. That's why I decided to make very public my belief in not having sex before marriage. It wasn't any kind of moral choice, as you probably can tell I'm a very sexual person, more a pragmatic one, and when I decided to go against my no sex before marriage promise, things only went badly. But that's getting a little ahead of myself.

"The huge success of Baby One More Time not only established me as a pop singer with a bright future but also gave me the money to fulfil my other ambition truly and pay for the surgery I so desired. So, I faked an ankle injury to get some time out to have the surgery done. Aided once more by my ever-helpful mum, I found a surgeon who could be trusted and heavily paid not to reveal anything personal. I finally had breasts, and what perfect breasts they had given me, just the size I had always wanted. I had lots of other more minor surgery, trying to make me look more like a woman but stopped short of full-scale gender re-alignment. My cock was the source of all my sexuality, all my desires. Although it could prove embarrassing or uncomfortable, I couldn't do without it, it was a part of who I am. Anyway, the surgery I had eventually resulted in the beautiful creature you see now lying beside you."

I had to compliment her surgeon. I knew from the Baby One More Time video how great she looked as a woman with just make-up and styling, but still her surgeon had made her even more perfectly so. In particular, those pert, round breasts were better than any that I had ever before seen on a natural woman.

"When my next video came out, for Sometimes," Britney went on, "a lot of the press noticed something different. The fact that I now had breasts didn't pass them by and there was lots of speculation and discussion over whether I had had breast enhancement surgery or whether I had just grown into them naturally. As if you could get tits like this naturally! Anyway, in all that speculation, not one person hit on any broader implication of this. Of course, I denied having any kind of surgery, but secretly I was pleased that the press should think themselves so clever to have spotted that but were totally missing the bigger picture.

"When I had first been starting out, I had got to go on tour as a support act for Nsync. It was here that I met up again with Justin Timberlake who had been one of my best friends in the Mickey Mouse Club days and had now grown into a fine, attractive young man. It surprised nobody when, soon after this, we started dating. Of course, Justin was no different from your average man in his early twenties; most of what he talked and thought about seemed to be sex. Of course, I was a beautiful woman in my early twenties so sex was on my mind quite a lot too, but I was still too worried about what Justin might think if he knew the real me. So I maintained the pretence that I wanted to remain a virgin, which was pretty tough when pitched against the constant pressure that the horny Justin put on me to do it and my own strong desires and urges.

"Another incident around this time also put a strain on my attempts to remain a virgin. I got a call from another former Mouseketeer who had just got a singing contract and a record about to come out, Christina Aguilera. She had seen and admired the success that Baby One More Time had given me and called up asking to come over to my place and wondering if I had any advice to offer her. I was always happy to help a fellow Mouseketeer and the company of a beautiful young woman just helped matters further. Anyway, Christina came round and I told her everything I knew and felt about the music industry from my brief success that far as a pop star. Christina was very grateful for all my advice. So grateful in fact that she felt vocal thanks weren't enough and had to express herself physically. This was before the outlandish hair and make-up that she has adopted these days, all she was then was a very pretty blonde girl with piercing blue eyes. Christina took me in her arms and kissed me on the lips. I had expected a brief thank you kiss, her lips brushing against mine for a fleeting moment, but this was nothing like that. She pulled me close to her and locked lips with me, slowly inserting her tongue in to explore my mouth. My eyes registered first surprise, then pleasure at the delight of kissing another girl. Christina began to pull the top that I was wearing over my head and that's when I realised that if I didn't do something there and then, she would want to go all the way and so would discover more about me than I wanted her to know. So, standing there in my bra and skirt, I had to tell her no, that wasn't the kind of thing I wanted, even though in my heart, and in my groin, I knew that it was. Christina's face fell with disappointment, I could read in those bright blue eyes that she had been really into it and had been able to feel that I was too, that why she was so hurt by my rejection. Things haven't been the same with us since, ever since then we've been massive rivals rather than friends, although whenever we meet there's just this huge sexual tension between us.

"Anyway, after the Christina incident, I felt that I couldn't go on doing nothing to satisfy my incredible sexual urges. So, I began by giving Justin head, soon becoming pretty expert at sucking off his cock so that, for a while, Justin didn't mind that I had promised to go no further with him. But, after this had gone on for a year or two, he started pressuring me once more to do it for real with him, and I began to wonder if I would lose him if I didn't. Besides, me and Justin had been together for a long time and we were so in love, I felt like I could probably trust him by now, that he would understand me and my secret. So, one night like any other, I revealed myself to him. He was shocked, which didn't come as much of a surprise to me, probably even more shocked than you were earlier on, after all, he thought he knew everything about me. Anyway, he seemed to understand, and that night we had such a wonderful night of passion as Justin took my long desired cherry, fucking my arse in a way that sent me to heaven. This was way better than anything I had ever dreamed it would be, and I'd had some pretty hot dreams.

"Unfortunately, this night was the end rather than the beginning of my magnificent sex life with Justin. It wasn't long after this that he came to me to say that it was over between us. That night when he had fucked me, he seemed to be really into it, really enjoying it, but now he seemed to worry about his masculinity. He told me that he had found himself a real woman who would see to his needs in a way that I never could, I later found out that this was Cameron Diaz and that Justin had gone running to her after our night together.

"After my break up with Justin, I was devastated. He was the only man that I had ever loved and I had felt sure that if anyone were to understand me then it would be him. I don't think I will or can ever love anyone so unconditionally as I did him. For a long time after that, I felt depressed and sexually repressed, I couldn't share my secret with anyone and I had no serious relationships until Kevin now. Kevin knows the truth about me and he stays with me. I don't know how keen he is on the idea, he doesn't fuck my arse, but he does enjoy me giving him head, and he loves the attention and envy he draws being Britney Spears' boyfriend. So I guess I'll have to settle for that, it's been so hard to find a man who understands and who wants a serious relationship."

She was referring here to Kevin Federline, her former dancer who she had recently started dating when I had my encounter with her and who has since become her husband.

I have to say, I felt for Britney's pain and loneliness. She was one of the biggest, most popular and most successful stars in the world, millions of men desired her, and it seemed that all her dreams had come true. Yet, at heart, she was just a lost little girl who had been trapped in a man's body and she yearned for someone to understand and love her. I've got to admit, having heard this much of Britney's life story, I was curious about some things and had to ask her some more.

"So what about all the other men you've been linked with?" I asked Britney, "What about your marriage in Vegas?"

Britney sighed and said, "Jason had been a friend of mine from back home, we had known each other for years. I was still depressed at the thought that I would never find anyone to understand the real me and I began to feel that maybe someone I was that close to, someone I had grown up with, might just be the one. One drunken night in Vegas, I managed to convince myself that this was true and demanded that we get married that very night. Of course, Jason jumped at the chance, but when it came to the wedding night and he saw fully what he had married into, he ran a mile and the marriage was effectively over from there."

"What about the other guys?" I said, "What about Fred Durst or Colin Farrell?"

"Fred Durst?" she laughed for almost the first time all evening, "I may be lonely but I do have some standards. Anyway, I don't think he'd be that keen on getting to know the real me. As for Colin, he was keen, definitely. And he was great, up until this evening, I'd have said that the night I spent with Colin was the best fuck I have ever had. But Colin isn't the kind of guy that you can tie down to anything, he isn't ever going to settle for a serious relationship with one woman, especially one who isn't all woman," here she smiled again as if fondly remembering that night.

I felt absolutely flattered and delighted to hear Britney add the words "up until this evening" to that last sentence, could it possibly be that the best evening of my life was also one of the best of hers? Whether or not this was the case, I had never felt closer to Britney than I did now having heard her tragic story. I really felt for her and I knew now that there was something I had done to her, something that I now felt particularly guilty about and had to get it off my chest.

"Britney," I said, "There's something I need to confess to you," I paused for a moment as she looked at me with confusion, wondering what I could be about to say, "There never was any videocamera filming you sucking me off. It was a lie to try and get to fuck you. I'm so sorry, I didn't ever guess any of this when I did it. I didn't know you like I do know. I'll do anything to make it up to you."

I had been worried that Britney might burst into tears once more, or, worse, throw me out of her room or report me to the hotel and lose me my job, or even to the police. What she did, however, was smile, a smile not unlike the one she had given me when I first suggested she suck my cock, a smile that suggested wickedly kinky thoughts were running through that beautiful blonde heard of hers.

"Well, I'm sure we can find some way of you making it up to me," she said.

5. Born To Make You Happy

Britney smiled at me in a wickedly seductive way, I wondered what was going through her mind as she told me that she was thinking of some way for me to make it up to her. I had done something pretty serious in blackmailing her into sex with made up video footage of her sucking me off, she'd be well within her rights to do anything to me. However, she appeared to be thinking of something pretty sexy, we'd hit it off pretty well and I kind of felt Britney's forfeit for me would involve something more fun and sexy.

I had thought that I was really in love with Britney before this evening, with the Britney I had seen in videos and interviews. However, I was now far more in love with the real Britney, the Britney who had let me fuck her in the arse, the Britney who had poured out her tragic and emotional life story to me and had made me pity her as much as I wanted her. She had made me feel that I would like to do anything for her, do anything to make it better, to make her happy. So, whatever it was that Britney was thinking of that I could do for her, I was more than happy to do it. She'd made me experience greater pleasure than I thought possible and now there was nothing I wanted more than to do the same for her.