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  • Oops, I Did It With Britney Pt. 02

Oops, I Did It With Britney Pt. 02

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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.

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