Five Times: First Time - Cover

Five Times: First Time

by MrBrightside

Copyright© 2020 by MrBrightside

True Sex Story: Mutual masturbation with my best friend's girlfriend.

Caution: This True Sex Story contains strong sexual content, including Teenagers   Consensual   Heterosexual   True Story   Masturbation   .

This is the first of five accounts I’d like to share with you about my experiences between 2008 and 2016. The first couple of stories are fairly tame, but they are true stories and they occurred when I was a lot younger and less outgoing than I am now.

October 2008. I was sixteen years old, newly enrolled at college, a bit of a geek, and I hadn’t yet had a serious girlfriend. Look, there I am, sat on the bus beside my best friend, Martin, sharing a pair of headphones and listening to Nine in the Afternoon by Panic! At the Disco on my iPod. People who didn’t know us thought we were brothers: we had the same wavy brown hair and cleft chin and weedy build; we finished each other’s sentences and shared our packed lunches and had similar interests – old-school Doctor Who, Hellboy comics, Call of Duty, and girls. Always the same girls.

(Even when we’d first met in the school playground several years before, our first words to one another had been about a blonde fifth-year student who had just walked past us on her way to the canteen – her skirt was caught up beneath her backpack, revealing her underwear and cute butt. Martin and I had grinned at one another. ‘Hungry?’ I asked him, and with that we’d hoisted our bags on our shoulders and trailed after her. From then on, we were inseparable. We sat together in all our classes, trailed after the same pretty girls during breaktimes, spent evenings at one another’s houses discussing the girls we fancied and sharing our fantasies about them.)

So, in October 2008, on the bus home from college, Panic! At the Disco was singing at us, Martin had his sketch pad open on his lap and was staring out the window for inspiration, and I was thinking about Kathy. Let’s picture her for a moment:

She has incredible eyelashes. (Whenever I thought of her, that was where I started, always.) With such pale skin, her dark eyelashes are vivid, almost severe. Her hair is brown, shoulder-length, loosely curled; she might laugh, or tilt her head, or reach down for her schoolbag, and her hair tumbles in front of her eyes, but it can never hide those eyelashes. She’ll reach up and, with the back of her forefinger, push the escaping curl to one side; and in that moment the severity of her eyelashes is diminished because all attention is on her eyes: wide soft brown eyes, keen, thoughtful, warm.

Martin was suddenly jabbing me in the arm with his pencil. ‘Who are you thinking of?’ he asked. He knew me well; he could tell I was thinking of a girl and he wanted to know more.

‘You don’t want to know,’ I told him, but he jabbed me in the arm again, albeit playfully, so I sighed heavily as though relenting and said, ‘Esme’.

Martin smirked, then looked back out the window. ‘Yep, you’re right. I don’t want to know that you’re fantasising about my little sister, thank you very much.’ And he left me to my thoughts.

Without doubt, he knew me well – but I knew him well too, and I knew this wasn’t the right time to mention Kathy. We had always liked the same girls and we’d always been open in sharing our fantasies, but this time things were different: Martin didn’t need to fantasise because he had the real thing – he had been dating Kathy since the start of term.


When I got home, Mum told me that she and Dad were going out for dinner, so Martin and I would have the house to ourselves. ‘Martin’s not coming over tonight,’ I said. Mum frowned but she didn’t push it, and once she and Dad had left, I went straight up to my bedroom and took all my clothes off and masturbated to Kathy’s Facebook profile picture.

I was in no rush. I glanced at myself in the mirror. I was slim – lanky, really, certainly not toned – average height, with dark wavy hair which was unmanageable and always out of style. I reached down and fondled my cock. I wandered around my room for a couple of minutes, idly staring out the window or scanning the titles on the spines of the books stacked beside my bed, stroking myself until I had a full erection. Then I found Kathy’s picture on my phone – it had been taken about three months before, during the summer, and she was wearing a thin white shirt which was unbuttoned, showing a sliver of her bikini top beneath. She had a wide smile, her head was tilted to one side, and she had her hand across her forehead, holding her hair out of her eyes.

I led on my back in my bed, on top of the covers, with my phone in my left hand, and the fingers of my right hand cradling my cock; I used my forefinger to gently caress the underside of the head through my foreskin. If I relaxed the muscles in the tops of my legs and in my butt, I could masturbate like that for hours without coming and, when I would finally reach orgasm, it would be incredible and would leave me shuddering and breathless.

Twenty-five minutes in, Martin knocked on my bedroom door. I knew it was him straight away – he had once inadvertently interrupted one of my epic masturbation sessions, and ever since then we’d always knock the drumbeat from We Will Rock You and wait for a reply before entering one another’s bedrooms: twice with your fingers, then once with your palm, and repeat: KNOCK-KNOCK SMACK, KNOCK-KNOCK SMACK.

‘Hang on a moment,’ I shouted, and I rolled under the bed covers before telling him he could come in. (The proper response we used to indicate that it was safe to enter was meant to be ‘It’s fun to smoke marijuana’, but I wasn’t in the mood this evening.)

Martin raised an eyebrow at the bulge in the bedsheets and asked me if I was still fapping to his little sister, Esme. ‘Yeah,’ I said. And then, ‘Actually, no.’ He picked up my phone from where I had left it on the pillow, then sat down next to me on the bed beside me.

‘I know who you’re thinking of,’ he said. The phone screen was still on, still showing Kathy’s profile picture.

Martin shrugged.

Martin shrugged, and he smiled, and he told me that it was okay. He liked Kathy so it was no surprise that I would like her too. We’d always liked the same girls. And this girl, she was amazing – mind-blowing, he said – and having spent the last few weeks with her, well ... his mind was totally blown. He didn’t apologise, but I didn’t expect him to because he had done nothing wrong. I had been the one who had been in a bad mood. All the same, I didn’t apologise either.

‘You want me to tell you about her?’ he asked me with a mischievous grin. And just like that, things were back to normal again.


When flaccid, my cock was four-and-a-half inches long, a good inch bigger than Martin’s; however, although mine only grew another inch when erect, Martin’s would almost double in size; whereas Martin’s foreskin would retract by itself as he stiffened, mine was tighter and needed encouragement to reveal the glans. We’d never been ashamed of being nude in front of one another, and we’d often masturbated together when fantasising about girls.

Martin stripped naked, and we streaked down the stairs and out into the back garden. It was getting dark, and cold, and the decking felt icy underfoot. We manhandled the cover off of the hot tub and plunged gratefully into the warm water. We didn’t bother switching the bubble jets on because they would be too noisy and I wanted to hear everything Martin had to say about Kathy.

‘She’s, what, five foot four? Brunette, brown eyes, usual number of limbs.’

(That was how it always started, no matter what girl we talked about, no matter that we knew exactly what she looked like: Always ‘usual number of limbs’ – it was traditional, part of the ritual, part of the build-up to the fantasy. And this time, when Martin said it, I was wide-eyed, shivering despite the warmth of the water, holding my breath in anticipation; because this time, he wasn’t sharing some fantasy with me; this time, he was describing his actual girlfriend.)

Five-four, brunette, brown eyes, usual number of limbs. Sweet sixteen. Slim: it makes her look taller than she is, and she’s small enough that we can wrap just one arm around her waist to pull her close to kiss her. She’s wearing skinny black jeans with grey suede boots. A tight, wine-red vest-top beneath a vintage velvet frock coat, closely fitted. The colour of the coat changes depending on the light – sometimes dark brown or dark red, other times so dark it’s almost black – and it’s unbuttoned, and it flows around her as she dances.

(‘Her hair falls in front of her eyes,’ I added, ‘and she sweeps it out of the way with the back of her finger.’ ‘Exactly,’ said Martin, ‘exactly like that.’)

The song ends and another one starts, one she doesn’t know. She looks slightly uncertain, unsure whether to keep dancing or not, but then we lean forward to kiss her again and she smiles, and her tongue touches ours, just for a split second. She tastes sweet, like apples. Then we’re helping her to remove her coat (‘We’re in my bedroom now,’ Martin said as an aside) and she sits in front of us, cross-legged on the floor, her back to us so we can give her a shoulder massage. The straps of her vest top are getting in the way, so she lowers them, and yet they’re still in the way; she turns her head, glances at us, unsure for a moment; and then in one quick movement she hoists her top up over her head and flings it on the floor beside us, revealing a black bra.

(‘We totally have a hard-on by this point,’ Martin said, ‘and Kathy clearly knows because it’s pressed against the small of her back.’)

We carry on massaging her shoulders and upper arms, reaching further forward and pressing harder against her. She starts to shift slightly, gently rocking from side to side, rubbing against our cock. Then she suddenly stops – pulls away, shuffles around to face us, and then reaches behind her back to unclip her bra.

(By this point my flag had returned to full mast – it was literally pulsing, begging for attention – and it took all my will-power not to attend to it. I was longing to hear Martin describe Kathy’s breasts. I closed my eyes, took a deep breath, held it for as long as I could, then exhaled. Hold on, hold on, I told myself.)

Kathy looks away, suddenly shy, and she pauses – then she glances at us out of the corner of her eye, smiles shyly, and removes her bra. Her bra is padded to make her bust appear bigger than it is. But, oh man, she doesn’t need to worry, we’ve always loved small breasts.

‘They’re slender,’ Martin said, ‘the perfect size to cup in our hands. Her nipples are the softest, palest pink; delicate and puffy, but they quickly harden when we lean forward and gently kiss them. We reach up, touch her chin, gently tilt her face towards us so we’re looking directly into her eyes. You’re beautiful, we tell her.’

The back door suddenly opened and Mum poked her head out to announce that she and Dad were home. ‘We didn’t bother with dinner,’ she said, ‘just a few drinks, so I’ve brought pizza home if you want some?’ I glanced down and noticed that Martin was sporting an erection even bigger than mine. I quickly reached over to the controls and switched the water jets on so that our enjoyment was hidden in the bubbles.

‘Uh, yeah, thanks Mum,’ I said. ‘We’ll be in shortly.’ She nodded and went back inside.

‘Dammit,’ said Martin, as frustrated I was. ‘And I was just getting to the best bit, too.’

‘Quickly tell me,’ I said, ‘have you seen her pussy?’ (I had never really liked that word, ‘pussy’, but my cock was fit to explode and I just wanted Martin to tell me as quickly as possible.) ‘What does she look like?’

Martin gave a massive grin and nodded, but all he would say was, ‘Oh, yeah... ‘


We dressed, ate pizza, and played a couple games of Call of Duty. Then, as he was ready to leave, Martin asked me if I wanted to see Kathy naked. ‘What, she let you take a picture of her?’ I asked.

Martin shook his head. ‘No. Well, yes, I’ve got nude photos of her. But what I mean is, would you like to see her naked? For real?’

My mouth had gone dry. ‘What, what do you mean? I mean, yeah. Yeah, I do.’

Martin grinned mischievously. ‘Come over to mine tomorrow night,’ he said. ‘Don’t ask questions. About six o’clock, alright?’

‘Yeah. Wow.’ I didn’t know what else to say.

Martin laughed. ‘Wow, oh yeah. Are you looking forward to seeing what my girl has to offer? She’ll be totally nude for you. Full-frontal, dude. You’ll see everything. I’m so excited for you.’

‘Wow,’ I said again. And then: ‘But won’t she mind? Don’t you mind?’

Martin laughed again. ‘We share everything, buddy. You know, we tell each other what girls we’re fantasising over, that sort of thing. We don’t have secrets.’ He punched my arm, playfully. ‘You’re gonna see everything. Kathy’s going to show you her beauty.’

After Martin left, I lay back on the bed. I didn’t need a picture this time. I imagined Kathy’s small breasts and her soft pink nipples and my lips on her skin, kissing her body, kissing her beauty. I didn’t bother taking my time, didn’t even try to relax – I just tugged on my cock, hard and fast, and I came, violently and voluminously, all over my bedsheets.


When we first started sharing our fantasies about girls, Martin and I set some rules. Well, not actual ‘rules’, but we started some traditions that would continue throughout our friendship, even to this day. For example, we’d always start by describing the girl (height, hair and eye colour, ‘number of limbs’); our stories were always told in first-person-plural (for example, ‘we did this to her’ and ‘she did that to us’) not because we were describing a threesome, but because in the fantasy we were a single unit; and during these sessions, we would usually masturbate together (though we would never touch one another).

One thing we spent some time deciding upon were the best words to describe anatomy. We were comfortable with cocks and dicks and penises, but the female counterparts were more troubling. ‘Vagina sounds so clinical,’ I remember saying once. ‘The word just doesn’t excite me.’

Martin agreed. ‘It’s not actually correct, anyway. The vadge is just the main entrance, where you stick your cock in. The whole thing, the lips and clit and everything, that’s called the vulva.’

I liked that even less. ‘And I don’t like the word pussy.’

Martin disagreed. ‘I dunno. I quite like pussy. Maybe not to start with, not when we’re first describing a girl, not when we’re setting the scene and explaining exactly what she looks like. But, towards the end, when things are hotting up – you know, when you just want to get down to business – the word pussy sounds good to me.’

So, what to call that particular area of a girl? Minge was too nasty-sounding, cunt did nothing for us, and all of the other terms we could think off were either too obscene or colloquial. ‘It needs to be something pretty-sounding,’ Martin said. ‘It’s our favourite part of a girl so it has to sound inviting, has to sound beautiful.’

‘That’s it, then,’ I told him. ‘Beauty. That’s what we’ll call it.’

 
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