Britney Story

"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.

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.