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…