My First Threesome

He had a book, that's what everyone said anyway. Justin Bradshaw's book of names and ratings of the women he'd conquered, had become the talk of the small town where I used to live. Newly single, I was intrigued. The knowing that someone as sexy as him wanted me, would pen my name in this infamous book, I wanted that validation.

I guess it was also because I wanted to be like him, that I never wanted to love someone again but to use men like my ex had used me, like Justin seemed to do with women too. To live in the moment, enjoy the act of sex and move on to the next, no strings. In a way, it was less about the sex and more about idolising what he was doing, aspiring to become the female version of him, someone the polar opposite of what and who I was.

It would be a bonus though, that someone like him could teach me a thing or two, if I was going to willingly go down the path of whoredom. I needed someone experienced to show me the basics at least, I'd never even gone on top before. I had lost my virginity at eighteen to my first proper boyfriend and had only had sex with him for the eight years that followed.

My ex had made me come to view sex as overrated, something that was only to be enjoyed by men, almost chore-like. I wanted to find out if there was more to it, I wanted to experience the type of sex that my childhood best friend Poppy had told me about. I had reasoned with myself back then that I was lucky to have a man committed to me, even if the pleasure of our sex was painstakingly one-sided.

Fast forward a year after our break up and I was ready to make up for lost time, I was fed up with dry-humping a pillow and watching lesbian porn to get myself off. I was still young and beautiful and I could feel a sense of urgency that my time was running out. I wanted to explore my sexuality, I wanted to know what it felt like for a man to make me orgasm, to see if it was even possible. Most of all, I wanted to know what it felt like to be wanted, desired, chased after instead of being invisible.

Most of my friends had a body count that exceeded the tally of the years of my life I'd wasted on my ex. Meanwhile, I had been a glorified sex toy for years to only one man, all the while quietly accepting that it was normal that I had never had an orgasm from being intimate with him. I mean, I never even pretended because he just didn't seem to care. He'd pumped away into me, night after night in the dark, his veiny dick making my pussy lips chafe where he'd go in hard and fast, dry. Then he'd cum and roll off of me, fall straight to sleep without so much of a thanks or I love you.

But Justin Bradshaw... he was always dressed head to toe in designer clothes, had a nice car and shit loads of money. He was a drug dealer and had been in and out of juvenile detention centres and more recently, prison. It was a combination that seemed to draw women to him like moths to a flame, myself included. It went against all rhyme and reason, really he was a walking red flag but nobody seemed to care.

It helped that he had a trophy girlfriend, it seemed to make him even more desirable. We are such bitches to each other when it comes down to it, I don't care what anyone says, girl code doesn't exist when it comes to men like Justin Bradshaw. If he wanted you, he was choosing you over (hands down) the hottest woman in our town at the time and that was undoubtedly a huge turn-on. Even other women who swore they were straight either wanted to be her or wanted to have her.

Lara was twenty-two back then, with a tiny waist and long bleached, blonde hair. She had a stunning face, a peachy bum, big green eyes and huge fake tits. Everyone said she was a filthy bitch too, which I guess was a bonus. If they'd have wanted a threesome with me I would have done it, if just she would have asked me to come over for wine, a takeaway with some scissoring after, I'd have done it. Even back then, when I didn't realise I was bisexual.

I wanted to be in his book. I'd been trapped in a relationship for the best part of my twenties when I'd been in my prime. I thought if I stood a chance with someone who was still pulling nineteen-year-olds and B-list celebrities, it needed to happen now-ish. I knew I wasn't ugly, men still did a double take when they passed me in the street. I'd lost two stone last year from heartbreak, so my figure was the best it had been in years. I'd gone back blonde which coincidentally was Justin's type and I had naturally huge tits, which I also knew was Justin's weakness.

All in all, it would be the biggest and best rebound I could have hoped to have. It would be the biggest 'fuck you' to my ex who had told me that nobody would want me, that he'd had the best of me. Well, I wanted to prove him wrong and prove to myself that I still had 'it' too.

Just thinking about being in Justin's bed, being in his and Lara's bed, where he fucked her, it made me have a tingling sensation between my legs. It was thrilling. Rather than feeling heartbroken, for the first time I felt excited about all that lay ahead. I realised how much I was free now to do and I was going to do it all and so much more.

I'd called Poppy one evening and told her my plan and she'd laughed, "You'll catch something!" She'd said, "He's a man whore!"

In truth though, Poppy had been historically more obsessed with Justin than I was as she'd lost her virginity to him. I hadn't been close to Poppy for years, my ex didn't approve of our friendship so I didn't think it was a big deal that I was interested in Justin. I wasn't going to let her gatekeep him, that was for sure. Surely she was over him by now? My ex had said that Poppy was a bad influence on me, that she was a slag and I'd end up like her if I wasn't careful. Looking back, I just don't think he wanted her to make me realise how much I was wasting myself with him.

I'd thought to myself though, would it be such a bad thing, to be a 'slag?' I kind of wanted to be. Justin slept around and that was celebrated, why the fuck couldn't I? I'd been loyal, chaste and where had that got me? Never again. It was nice to have Poppy back in my life and I needed her guidance with men, I needed her connections anyway. She was a socialite, a party girl and I needed to hang on her coattails if my plan to fuck the hottest guys around was going to succeed.

"He'd never cheat on Lara with you babe, as pretty as you are, no offence." She'd said gently, almost a little condescendingly.

"You're in the book though, right?" I'd asked her, trying to conceal the hurt from my voice.

"Yes and more than once, he showed me the book and he's never shown anyone else, not ever." Poppy purred.

"So you think I'm not as pretty as you are?" I asked her, "Is that what you're saying?"

"What I'm saying," she said, "is that it's not just looks that he goes for babe."

"What do you mean?"

"Lara pegs him and eats his arse like a fucking cupcake. He's into freaky shit and you're more ... girl next door if you know what I mean." I could almost hear the satisfaction in her voice. She always wanted me to do well, and to be happy but never more so than her.

"She does what?" I asked, thrown off for a moment, having no fucking clue what pegging meant and horrified that anyone would put their tongue inside someone else's arsehole.

"Pegs him. Puts on a strap-on and fucks his arse with it. He loves it."

"Right..." I said quietly, my voice catching in my throat, "So you've done things like that with him too?"

"I'm not about that!" She'd laughed, "But he loves my nipples, that's for sure. He told me they're the best nipples out of all the women he's slept with."

I thought about my nipples and wondered what he'd think about them.

"I'm sending you a picture, so you can see what I mean." She'd said, as she sang along to the radio in the background.

I opened up iMessage and was confronted with an image of Poppy sitting topless in her dressing table mirror, brushing her long, mermaid-like, black hair. She was right, she did have beautiful nipples, they poked through the strands of her loosely hanging hair. In fact, she had beautiful tits, I guessed she was about a C cup but they were round, full and perky.

I couldn't stop looking at her areoles, they were so small, a shade darker than her smooth, coffee-coloured skin. Not for the first time, I felt my pussy responding to the form of a naked woman. I loved the soft curves of her breasts, the hardness of her nipples and, closing my eyes I imagined what it would be like to suck on them, to have them in my mouth.

"You have lovely tits." I sighed, registering that I would have to get myself off when I got off the phone from her. I'm sure she sent me shit like that on purpose, after all, she knew I was curious about my sexuality. Mixed race women seemed to turn me on the most too, really pretty and feminine ones, women like Poppy. Sometimes, I indulged in that fantasy knowing that it could never happen, that it would ruin our friendship. I doubt she saw me in that way anyway.

I was beginning to think this wasn't going to work out after all, with Justin. I thought of my huge areoles on my slightly drooping breasts, with my long, permanently stiff nipples that looked like they might poke someone's eye out. I'd thought my tits were nice for natural ones but perhaps them just being big wasn't good enough for someone like him. He'd probably seen some amazing ones and I suddenly felt insecure about my body.

"Thanks, babes. Just send him some naughty pics and see what happens. You never know. Just see where it goes?" Poppy said in a distracted way, which meant she was starting to lose interest. If we weren't talking about Poppy or something that could benefit her, there was always a time cap on the conversation.

"I'll think about it." I'd said and we'd said our goodbyes. Rather than feeling empowered and encouraged to hook up with the infamous Justin Bradshaw, I felt deflated and substandard.

As it so happens, I didn't have to send him anything because he messaged me first. It must have been about a week after that conversation with Poppy that he'd slid into my DMs on Instagram. I couldn't bring myself to send him naughty pics like Poppy had suggested, I'd never sent a nude to anyone before and I'd lacked the confidence. I'd followed him on Instagram though, so at least he would know I existed and I had uploaded a selfie to my story. My camera roll was full of rejected selfies I'd taken in a bid to take one that stood the best chance of garnering his attention and it seemed like it was worth it.

He'd wanted to come over, right then, ten minutes after he'd first messaged, he certainly wasn't one for chit-chat. I was in bed at the time, aimlessly scrolling through my feed and I'd already taken my makeup off. I'd asked him if he could give me an hour to have a bath and get ready at least. He was straight to the point and so persistent that it was heady, I felt on top of the World, like nothing else mattered. Justin Bradshaw wanted me!

Had Poppy messaged him? Put in a good word for me? I didn't feel like a woman nearing thirty, I felt like a teenager. What was the saying? 'You're only as old as the woman you're feeling' Except for in this case, it was the other way round, Justin was twenty-two and I was twenty-eight. There was something so juvenile about the way I was carrying on but I'd missed out on all of this stuff. I just felt like I was late to the 'party' and age seemed irrelevant to me at the time.

Expecting me to be 'fuck ready' in ten minutes though, that was crazy! Maybe fresh faced younger women could but I'd need a little more prepping time.

"Send me a picture of you." He'd messaged, ignoring my pleas for longer to get ready.

I pinged him over a selfie from my attempts at a sexy photo shoot the day before of me licking my lips suggestively, which he'd viewed immediately. That was the only one send worthy, I'd tried out numerous poses but they were all cringe-worthy, I'd looked painfully amateur, stiff and awkward.

"No. Your tits." He'd replied straight back.

Fuck. I couldn't send him that. His girlfriend likely had perfectly augmented tits and probably to his specifications. Judging by Poppy's too, there's no way mine would meet his expectations. I quickly searched and screenshotted some Google images and sent them to him.

"They're not yours" He'd replied, "I can be at yours in ten minutes???"

How did he know? I didn't want to turn him down, he'd told me it was that night or never. Likely he had a whole roster of women waiting in the wings for an impromptu booty call, so that was seemingly my one opportunity.

I made a quick decision that I'd have to chance it that he'd be back another time. I'd rather risk never getting to sleep with him than him seeing me essentially look like my younger brother. I had no makeup on and my hair was shoved up and all over the place.

"Another time?" I'd semi-pleaded, hating myself for coming across so desperate.

I got no response. I think I cried myself to sleep, which looking back seems pathetic. I was determined though, one setback wasn't going to get me to change my mind. I wanted to be seen, if not by Justin, then by the circle of friends he moved in. It seemed like that was the only way to get his attention back to me, it had to work.

I'd have to do something wild, I'd have to become like Lara, a filthy bitch. He liked filthy, didn't he? Isn't that what Poppy had said? Then I'd have to become somebody else, I'd have to take off this girl-next-door 'suit' and put on another one altogether. This was the time when my alter ego, 'December Gray' was born, although I didn't name her until many years later.

I don't do anything by halves, that's for sure. I hadn't been 'out-out' since I was at college, which had been nearly ten years ago at that point. I decided it was high time to get back out into the arena of life. I'd found out the club where Justin and his friends frequented and convinced Poppy to come along. Long story short, I ended up going home with two of Justin's friends, Jake and Louis. It was too easy, surprisingly easy.

I'd invited Poppy home with us too, secretly hoping that we may end up drunkenly hooking up but she'd been too coked up. She'd ended up going on to another club, with some friends she'd bumped into. I'd watched her leaving the club, partly in awe of her confidence in wearing lingerie and Loubs to the club but also with disappointment that she didn't want to come with me.

In the cab on the way home, sandwiched between two very sexy twenty-something-year-olds and despite being intoxicated, doubt began to creep in. When I'd told Poppy what I was planning on doing, almost shouting to be heard over the loud drum and bass, she'd just raised one perfectly arched eyebrow and laughed. I wanted to slap her in her face, she had no idea what I was capable of. I hated that I cared what she thought, that I wanted her approval. I could feel the inward struggle of my alter ego trying to take over but Poppy was always right there, pouring cold water on her.

December Gray didn't take shit from anyone though and she was getting stronger. December was more than Poppy's and more than Lara's equal in every way. The 'girl next door' me, the one who had always let people walk all over her, the one who had laid on her back in the dark night after night and let a man taint the beauty of what sex was all about, yes, she was dying, I could feel it.

Likely, Poppy found it amusing that someone like me would do such a thing and she probably didn't believe I would follow through. I decided to call her the next day and give her all the details, that night though, I put Poppy and her perfect tits out of my mind. All I wanted was to have sex, outrageously naughty sex. A threesome was a good starting point and definitely out of my comfort zone.

"Look at those fucking legs!" Jake wolf whistled drunkenly as I jumped out of the taxi, Louis fumbling for his bank card to pay.

"Thanks..." I mumbled, feeling the heat rising to my face. This was all so new to me, men noticing me, complimenting me.

Once we were inside and I'd closed the front door, I panicked a little as I could feel the booze wearing off. 'What the fuck was I doing?' I'd thought, 'That isn't me, this it is madness that I thought I could do this...' I'd never brought a man home, not ever, let alone two friends expecting a threesome. I mean, it had been my idea, I had suggested it at the bar as the sexual tension between each of us was electric. Louis had practically been fingering my freshly shaved pussy on the dance floor as Jake was behind me, lifting my mini dress, pushing his shaft in between my arse cheeks.

Now though, as Jake was kissing the nape of my neck (we were barely inside the front door) and Louis had made himself comfortable on my sofa, rolling a cigarette, I felt frigid, anxious I'd fall short, that I'd disappoint them. After all, as Jake ran his hands over the front of my low-cut black dress and caressed my left breast, I thought of how I'd only slept with one man. I was practically still a 'virgin' in many ways.

"Relax." He'd whispered in my ear, nibbling my lobe and sending a wave of static throughout my body.

I realised I had been tensing every muscle in my body and so I let out a deep breath and began to enjoy Jake exploring my body. Louis lit up his cigarette and started to watch us, rubbing his hardening dick through his khaki-coloured jeans.

"That's better," Jake said, pressing his lips against mine, slowly at first, carefully pulling the straps of my dress down over my shoulders.

I wriggled my body so that the dress fell to the floor, leaving me standing there in my carefully selected, matching black underwear. I'd gone to Victoria's Secret in the week and bought myself some nice new underwear, after having worn the same bra for the past five years or so, not exactly one-night stand-worthy.

Louis had pulled his jeans and boxers down around his ankles, his cigarette now extinguished in an empty wine bottle on my coffee table. I pulled away a little from Jake's now frantic kisses, to watch in amazement at how hard Louis was. I marvelled at the difference in his dick from my ex's. I'd never really seen another in the flesh before. Louis was small in comparison and I didn't know that I would be able to feel it when he put it inside me. A rush of adrenaline pumped through my body nonetheless, as I realised he was hard because of me. ME. He was stroking his dick up and down slowly, licking his lips, his eyes hungry.

"Take it all off," Jake said, taking me by my chin and pulling my face back toward him, the alcohol hot on his breath.

I froze. I couldn't get my tits out. Looking between these two men watching me expectantly, I realised I had no choice. 'Fuck it.' I'd thought, we were all completely wasted, they wouldn't even care, and they wouldn't remember that my tits weren't perfect. I'd hoped, anyway.

I pulled my black, lacy French knickers down first and pushed them out of the way with my toes. I reasoned that if I got my pussy out first, it would soften the blow of my disappointing tits. I knew that my pussy was pretty, that other than my face and apparently my legs, it was my redeeming feature. I had a tiny slit that started quite far down my pelvis and my clit was all tucked in nice and neatly. I had also made sure I was freshly shaven and had moisturised it with my expensive vanilla body lotion for tonight.

"Fuck." Jake said, kneeling in front of me just to look at it, "Fuck."

He kissed the top of my slit slowly, breathing in the scent of me as he did. I let out a moan, feeling his breath, his lips just there, just before where the dull throbbing had started. No man had ever put his face so close to my pussy, it was something I'd only ever seen in the porn I had watched over the years when I pleasured myself in secret.