Five Times: Second Time - Cover

Five Times: Second Time

by MrBrightside

Copyright© 2020 by MrBrightside

True Sex Story: She shaves for me.

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   True Story   Workplace   Masturbation   .

This is the second of five accounts I’d like to share with you about my experiences between 2008 and 2016. Most of this took place in December 2010 when I was 18. As with my previous account, this is a true story; however, in this one I’ve made the decision to change the nature of the place that I did my apprenticeship at, and changed the name of the girl, because both of us still work there.


About a week after I masturbated with his girlfriend, Martin told me that he and Kathy had split up. It was early on a Saturday morning when he texted me. WE’VE FINISHED, the message said. ALL OK, MUTUAL DECISION. Then he’d sent me a picture message with the caption, SO WE DON’T FORGET ;)

I wish I still had that picture. I lost it or inadvertently deleted it years ago, but I remember it perfectly: it was a photo Kathy had taken of herself and Martin, reflected in a mirror. Kathy was in the foreground, with Martin stood behind her. Kathy was holding her camera phone in one hand and holding up the hem of her skirt with the other, and she wasn’t wearing any underwear. Martin was reaching forward and down, his hand pressed against her mound, spreading her lips open with his fingers. The picture was dark, but it was clear enough to see the glistening inner pink of her beauty.

A few days later, during the autumn half-term holiday, Martin and I were in his room, sat next to one another, he in his gaming chair and me on the floor beside him, watching YouTube videos on his laptop and masturbating.

‘Don’t you mind that Kathy showed herself off to me?’ I asked him.

Martin shook his head. ‘Nah,’ he said. ‘We’re friends, so it doesn’t matter.’

‘But I saw her totally naked. She spread her legs and touched herself, right in front of me. Aren’t you, like, jealous that I got to see that?’

Martin turned to look at me, and he stopped stroking his cock. ‘Look man, I knew you liked Kathy. We’d fantasised about her for so long. Finally, when I got the chance, I wanted you to see her.’ He started jacking again. ‘Anyway, it was hot. I got her to tell me all about it after you left.’

‘Did you ever have sex with her?’ I asked him.

‘No,’ he replied. ‘Obviously I wanted to, and we did other stuff, but we never had actual sex.’ I asked him what ‘other stuff’ they’d gotten up to. ‘Oh, you know,’ he said, ‘we masturbated together, and masturbated one another. She never let me put my fingers inside her though, I was only allowed to touch her lips and diddle her clit.’

I was getting close to coming. ‘I wish I’d been able to touch her,’ I said. ‘I wish I’d been able to rub my dick against her. Fuck, I’m so close.’

Martin reached for his laptop and opened the picture of him spreading Kathy’s pussy lips apart. We stared at the picture, at Kathy, at the pink between her legs, and we came within a few seconds of each other.


Over the next eighteen months, Martin had a couple of girlfriends, but none of them lasted long and he wasn’t able to organise another evening like the one I’d spent with Kathy. We met up regularly to masturbate together, sometimes at his house, sometimes at mine.

Once, his sister caught us: Martin and I were both naked, jacking off like there was no tomorrow, when the door opened and his sister, Esme, walked in; she had just got out of the bath and was wrapped in a towel. Martin had bellowed at her – something like ‘GET OUT, WE’RE GETTING DRESSED!’ – and Esme had squealed, dropped her towel, and ran out of the room. I had carried on masturbating, savouring that fleeting glimpse of her naked body.

Another time, when Martin and I were spending the summer holidays at my uncle’s farm in Wales, my cousin and her friend took us down to the wide river at the bottom of their garden. My cousin was a freckled redhead, tall and slightly plump, and Martin took an instant shine to her. I was more interested in her friend, a goth girl with short spiky black hair and a nose piercing. They were both a couple of years older than Martin and me – maybe eighteen or nineteen. It was a hot, humid day, so we stripped down to our underwear and swam in the cool water. Martin and my cousin swam across to the other side of the river and started to make out on the bank. Feigning embarrassment, the goth girl and I swam a little further downstream and sat in the shallows. She took her bra off and showed me her perky, conical breasts and pierced nipples. She let me fondle her breasts for a few minutes, but before I could get any further, she decided it was time to re-join my cousin and Martin.

College ended. Martin went to university in Bristol, and I got an apprenticeship at a local law firm. Bristol was only an hour’s drive away, but neither of us had our own transport so we rarely met up. We texted one another, and chatted online when playing Call of Duty, but I missed him a lot. Sometimes we didn’t speak for several weeks at a time, and when he visited me during the summer break of 2010 – the first time we’d actually met face-to-face since he’d started uni – things were a little awkward between us. He told me about some of his adventures with the girls in his class, but we never quite settled back into our relaxed discussions, and neither of us brought up the topic of masturbating together.

A week after he had returned to uni, he phoned me. He said he was sorry things had been weird when he visited me, and he wanted us to be friends like we used to. I told him that it would be easier if we kept in touch more. We decided to book a holiday together for the following summer. ‘Amsterdam,’ he suggested. ‘We can stay in a cheap hostel. We can drink and visit the coffee-shops and red-light-zone, catch a sex show, that sort of thing.’ I agreed; it would give us something to look forward to and encourage us to keep in touch.

From that point on, everything was about saving money for our trip. I focussed on my study, hoping to finish my apprenticeship early and start full-time work for the law firm. My hard work was acknowledged and in September I became a junior probate solicitor. By the end of November I had saved enough money to cover the deposit for the Amsterdam trip. And in December I met Violet.


Last Saturday, following the easing of the Covid-19 lockdown, I visited Martin. His wife was out – she works for the NHS – so we sat together in his back garden at a social distance and spoke about old times and old girlfriends. I told him that I’d written about Kathy.

‘You got her age wrong,’ he told me after he’d read the story. ‘She was in the school year below us, so she was fifteen, not sixteen. Otherwise, it’s really good. Really hot.’ He asked me if I was planning to write about our holiday in Wales. ‘I lost my virginity to your cousin on that riverbank,’ he told me with a wistful look. ‘Crap sex, but wow, she taught me stuff.’

I pointed out that he’d only been alone with her on the riverbank for five minutes. ‘Well,’ he said, ‘I’m a fast learner.’

Later, just before I left, Martin told me that he was looking forward to reading the next story. ‘When are you going to mention the hotel incident? And are you going to write about Esme?’

‘The next one is about Violet,’ I said. ‘Amsterdam and the hostel incident and the brothel, that will probably be the third one.’

‘And Esme?’

‘That’ll be the last one, I guess.’

‘I don’t think I’ll read that one,’ Martin said.


I met Violet on 6 December 2010. It was a Monday. I remember it vividly. Here is how I might have described her to Martin:

She’s twenty-four, six years older than us. Five foot seven. Blonde hair, grey-blue eyes, the usual number of limbs. But not just blonde hair – it’s really, really fair, almost white; and it’s straight and long, almost waist-length; and when she’s intensely involved in something or deep in concentration, she pushes her hair back and tucks it behind her ears. She has a thin smile and high cheekbones and brilliantly white teeth. Her body is lithe, athletic, toned. She has full round breasts which look bigger than they are because of her slim build.

‘She’s obviously looked after her body,’ I would have said to Martin, if he hadn’t been at university. ‘Really worked to get back into shape. You’d never have guessed.’

‘What?’ Martin would have said, frowning. ‘Guessed what?’

‘That Monday, the sixth of December, was her first day back in the office after twelve months’ maternity leave.’

Martin would have grinned and slapped me on the back. ‘Ah, brother,’ he’d have said, ‘you’ve gone and fallen for a MILF.’


Violet wasn’t married, but she had been with her boyfriend, Luke, since college, and they had one child. She worked part-time as a receptionist for the law firm whilst her son was at nursery, and then worked part-time as a waitress at a local restaurant in the evenings when Luke got home from work. She was down-to-earth, easy to chat to, and laughed at everything. Everyone found her fun to be around – and I was no exception.

Within the first couple of weeks of December, she took me under her wing. She had worked in the probate department for several years before she took maternity leave, and although I was a junior probate solicitor and she was just a receptionist, she knew more about the legislation and administration than I did, and she assisted me with difficult cases.

‘I did all the same training as you,’ she told me at breaktime on that first day. We were stood in the alley at the back of the building, sharing a cigarette. I never used to smoke much back then, but she had offered me a ciggie and I had accepted, mostly as an excuse to stand and chat with her. ‘They offered me a junior solicitor role two years ago, but they wanted me to go full-time and that wasn’t going to work for me because Luke and I were trying for a baby, and I knew I’d want to take a year off.’

She was always really open, and she could talk for ages about anything. And when she wasn’t talking, she genuinely listened. She remembered things that I said in passing – for instance, one day I mentioned something about Doctor Who, and the next day she brought me in a stash of old Doctor Who DVDs that Luke no longer wanted.

I used to start work before her, so I’d have a cup of tea waiting for her when she got in. We’d take a ciggie break together at around 11am, then I’d take a late lunchbreak at 2pm (when Violet finished work) and we’d walk into town and grab a coffee or a sandwich before she collected her son from nursery.

Within a week, I was hopelessly infatuated with her. But there was nothing I could do; Violet had a boyfriend, not to mention a year-old-son; there was no way she’d throw that away for an inexperienced virgin who was six years younger than her.


During the third week in December, there were two developments:

First, Violet booked one of the function rooms at the restaurant she worked at, on the Friday night, as the venue for our office’s Christmas party. I was excited – it was for staff only, no partners, and when I jokingly asked Violet whether she’d go as my date, she had laughed and agreed.

The second development was something of a mixed bag. When Violet came into work on the day before the Christmas party, she wasn’t her usual chirpy self. She barely spoke to anyone, and when it was time for our cigarette break, she made her excuses and said she need to make a personal phone call. She didn’t return after that, and when I asked my colleagues where she’d gone, they told me that she and Luke had broken up, and she had taken annual leave. She wouldn’t be back to work until the new year.

My initial response – I’m somewhat embarrassed to admit – was one of joy. Violet was single! I could make my move! But I quickly had a sobering thought – it dawned on me that if she was taking time off work, she was unlikely to be at the Christmas party the following evening.

I spent the rest of the day in the doldrums. I couldn’t focus on my work. At lunchtime I wandered aimlessly around town on my own. I had never felt so pissed off or morose in my entire life. In the course of just a couple of days I had been given the opportunity to spend the evening with Violet as her date at the Christmas party, and then had the rug pulled from under my feet.

That night, I couldn’t sleep. I wasn’t even in the mood to masturbate. Eventually I texted Martin, asked if he was awake. He phoned me straight away.

‘Thanks for sending me the money for the deposit,’ he said. ‘I’ve booked the trip! Man, in six months’ time we’ll be in Amsterdam!’

I told him that was cool, I was excited, that sort of thing. He could tell straight away that something was wrong. I explained about Violet (twenty-four, five foot seven, usual number of limbs) and the party, and her breakup with her boyfriend, and that she wouldn’t be going to the Christmas party tomorrow.

‘You know that for a fact, do you?’

‘Well.’ I faltered. ‘Well, no, actually I don’t. But she’s had to take time off work because of the breakup. I can’t see her going to a party after that.’

‘But she took annual leave, right?’ asked Martin. ‘If she took sick leave to deal with that shit, it would be different; it probably wouldn’t be right for her to go to the party. But if she’s taken the time off as annual leave, that means she’s being sensible about the whole thing, and maybe that means she’ll be at the party.’

I wasn’t sure I entirely followed Martin’s logic, but it gave me a glimmer of hope.

‘Trust me, man,’ Martin said. ‘Dress to impress. She’ll be there.’


And the son of a bitch was right.

Seven o’clock, Friday night: I’m sitting with my colleagues in the function room at the restaurant, wearing a paper crown from a Christmas cracker and sipping a pint of Carlsberg, and suddenly I feel a hand on my shoulder.

‘Sorry I’m late,’ Violet said. ‘I hope you didn’t think I’d stood you up.’ She laughed, and I bought her a glass of wine, and we spent the whole evening talking.

We sat together in one corner of the room, avoiding our work colleagues. Violet was wearing a little red dress with a wide black belt. It looked like very thin material, and I couldn’t see any bra lines or straps, and I wondered if she was wearing anything under it.

‘Luke and I have had our ups and downs over the last eighteen months,’ she explained. ‘I was pretty hard work throughout the pregnancy, really hormonal. Luke was really good the whole way through, and we both thought it would be easier when Jed was born. But boy, were we wrong!’

‘Not easier?’

‘Not a bit.’ She smiled, took a sip of her wine. ‘I mean, we both love Jed to bits, and it’s so rewarding, but bringing up a child is difficult. And although Luke had been brilliant throughout the pregnancy, he’s struggled since. Things haven’t been good between us for quite a while.’

‘Do you think you’ll get back together?’ I asked her.

Violet shrugged. ‘Maybe. I mean, probably, eventually. We just need some space from one another for a bit, learn to appreciate one another. But space is difficult, especially when you’re bringing up a one-year-old.’

I finished my beer. ‘Yeah,’ I told her, ‘you definitely need some space, some downtime. Want another drink?’

 
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